nervousken | Jun 16, 2025
For $200, they'll let you watch

wanker-Jim | Jun 16, 2025
I get my pension check on Monday. Will you be around here then?

nervousken | Jun 16, 2025
Now or never, honey!

wanker-Jim | Jun 16, 2025
mon Holy shit, you mean you’d really do it? I don’t have the ey right now, but can we work something out?

nervousken | Jun 16, 2025
"How can we be sure you'll pay us?"

wanker-Jim | Jun 17, 2025
I I’ll pay you, Sweetie. I promise. Umm I cangive you my name and addres and phone nymber. Will that be enough for now? Please

nervousken | Jun 17, 2025
What, exactly, are you wanting to pay them to do?

wanker-Jim | Jun 17, 2025
I’d love to watch you two play with each other, or play with me. Do eyou want, I/d be happy just watching you.
Just please stay naked.

nervousken | Jun 17, 2025
"Whatever we want? Are you sure?"

wanker-Jim | Jun 17, 2025
I think so. Yes. As long as I get to watch you.

nervousken | Jun 17, 2025
Well, we have a way to make certain you pay us.

wanker-Jim | Jun 17, 2025
I smile, “Really, sweetie? How do yotoy4

nervousken | Jun 17, 2025
"We'll just lock you in a chasyity cage and then put on a show. You'll have to paybus to unlock you"

nervousken | Jun 14, 2025
Even if 28 minutes are post orgasm pleasure torture?

wanker-Jim | Jun 16, 2025
28 minutes? Yikes.

nervousken | Jun 16, 2025
Well, a woman like that can make guys like us pop in no time!

wanker-Jim | Jun 16, 2025
Yes, I imagine she could … but she is so damn sexy, I’m still tempted to accept that challenge with her.

nervousken | Jun 14, 2025
Then you need to practice!

nervousken | May 19, 2025
You know, you are absolutely right. It's disrespectful. From now on, I'd like you to SHOW my friends why we call you Little Jimmy. Any time I ask.

wanker-Jim | May 19, 2025
“ANNE … NO That’s not what P meant. I mean … I’m sure that many of them have heard umm stories. And, I’m sure that all the others will find out … one way or another. I just .. I just don’t need everyone calling me ”Little jimmy.”

nervousken | May 19, 2025
What would you like to be called?

wanker-Jim | May 19, 2025
* Well, uc ould just call me Jim. That’s what everybody else calls me except You … and Tara. *blush*

nervousken | May 19, 2025
I'll make you a deal. Tara and I will each invite five friends to come over. You do what I ask in front of them for an hour two, and then all thirteen of us will come up with nick name ideas and vote on one. You can make ypur case to everyone then.

wanker-Jim | May 19, 2025
“But Anne tt hat’s not fair. I mean, I I didn’t say my wienie wasn’t little umm smaller than some of the guys … okay, it’s littler than MANY of the guys.” *I squirm and blush harder* “But I don’t need you advertising about the size of my wienie. And Anne … PLEASE don’t make me show the other girls my penis.” *Blush9ng, I look down at the front of my pants.*

nervousken | May 20, 2025
Anne smiles "Did I say I was going to have you show your weenie to my friends?" Anne pauses for a moment. "But, now that you mention it, that is a really great idea. I am so glad you thought of it" She takes a step back. "OK, pull it out. You look nervous, might as well get used to being comfortable showing your weenie to me"

wanker-Jim | May 20, 2025
?ANNE? … Really? I exclaim in surprise as I blush hard, and I place my hands over my growing bulge in my pants. “You said you’d make me show your fiends why you call me lilojimmy, so I thought that’s what you meant.” … I think about storming out of the room, but I pause, and Iask her, “What … WhaT do You mean, Anne ???”

nervousken | May 21, 2025
"Little Jimmy, did I ever say WHY I call you LITTLE JIMMY? Did you assume it was because you have a little dick??"

wanker-Jim | May 21, 2025
I look at my sister, confused andembarressed, “Well, since you told me that you heard that I have a little penis, you started calling me “Little jimmy”, so yes, I assumed that was why. And when you and Tara call me little jimmy, you seem to be refering that I have a little dick. … So, iif that isn’t why … why don’t you tell me why you call me that?”

nervousken | May 22, 2025
"Do you have a little dick, Little Jimmy?"

wanker-Jim | May 22, 2025
Upon hearugf my sister’s question, I nearly panic.Feeling myself blushing, I look into my sister’s eyes, and this calms me down. As I collect my thoughts, I finally answer her,” “Yes Anne,I guess I do have a little dick … smaller men … I’m sorry Anne, I hope that you a’re not ashamed ofme.” After telling my sister this, my eyes lower and I look to the ground.

nervousken | May 22, 2025
Anne smiles. "It can't be that bad, Little Jimmy." she says, trying to comfort you. "Why don't you take a moment and collect yourself. When you are ready, I would like for you to undress completely, then walk down the hall to my room. Make sure you tug at it a few times at the door before you come in to make sure it is as big and hard as you can make it" Seeing your discomfort, she squeezes your hand. "Relax, Little Jimmy. It can't be as big of a deal as you make it" and she walks to her room, leaving you to your thoughts.

wanker-Jim | May 22, 2025
Seeing my sister staying calm and comforting helps me relax a little. Having to walk to her bedroom naked scares me a little, but nobody else is home, so going to Anne’s room naked seems kind of exciting. I get undressed ahd tug on my little dick, as I think about Anne wanting me to do this. Onc e Ihave my courage up, I walk to my sister’s bedroom, keeping my erection as hard as I can. I tug my dick a little more,and then go into Anne’s room.

nervousken | May 22, 2025
You open the door and walk in, naked and hard, holding yiur cock in your hand. Anne is holding her phone and videoing the whole thing. You freeze and she stops recorded and puts her phone down. "Little Jimmy, that is just some insurance in case you get any crazy ideas. Anyone that sees that video will think you are a sex pervert that walked into my room whole jerking off" you look nervous and beg her to delete the video. "Relax, LittleJimmy. I have no desore to get you in trouble or anything like that. I just want you to remember who is in control here." Anne lays on her bed, leaning back against the headboard "Do you know who is in charge here?"

wanker-Jim | May 22, 2025
Nearly trembling from embarrassment, anger, d intimidation … I just star eat my sister for a moment .With both of us knowing that I would never physically harm her, I realized I that had I had no other options. “Yes, You are in charge, Anne” ,I softly reply. Then I hang my head, as I now stare down at my little erection. “What… What do you want me to do now, Anne?” I ask my sister, quietly in a defeated voice.

nervousken | May 22, 2025
Anne smiles warmly. "Little Jimmy, please don't be mad at me" she looks at you for a few moments. "Honestly? I hadn't thought about what I'd like to see you do. I know you sneak in to steal my panties and I know you jerk off thinking about me. Why don't you tell me a little about that?" Anne seems to be completely relaxed and there is no hint of meanness or anything in her eyes

wanker-Jim | May 22, 2025
My eyes grow wider at Anne’s request, but She also helps me relax and I manage to get he ra little smile. “Well, they ae convent,, they make it more fun and sexy. They feel nice, too. … Anne , I don’t know what to tell you about jerking off in them … They make me cum hard. And I always make sure that they are washed before you get them back. Oh, with the soft, slick material, I don’t have to use lubricant to jerk pff.” Realizing how much I told my sister, I blush. “I umm, I don’t know what else you want to know”. … Then I add, “Anne, how long have you known that I umm use your panties that way?”

nervousken | May 23, 2025
"I've known long enough... which panties are your favorite? Describe them to me"

wanker-Jim | May 23, 2025
Oh. MY favorite? Don’t laugh but really like your light pink satin thong, the one with the red flowers on it. They llok great on you, and umm I always have fun u=with them, too.” J blush as I describe the panties to my sister.

nervousken | May 23, 2025
"They look great... on me? When did you see me in a thong?"

wanker-Jim | May 23, 2025
Well, you have a thong bikini , Anne. And umm there have been a f ew times that I umm … happened to be walking oast your bedroom, and I looked in the window and saw you. There have also been a couple times, you walked down the hall to the bathroom at night, without a robe or anything. But don’t worry, you look good in a thong, Anne.” As I blush, I manage to smile a little.

nervousken | May 24, 2025
"You dirty little pervert" Anne laughs. Not a mean laugh, her eyes sparkle with delight at your hinest answer despite your discomfort. "Sonyou spy on your sister. Tell me, have you ever seen me naked?"

wanker-Jim | May 24, 2025
Relieved that Anne seems amused, rather than angy, I relax. Then glancing up her body, I look at my sister as I answer, “No, Anne, I haven’t seen you naked. I HAVE seen you topless at times, but never completely naked.
Then give my suster a happy smile

nervousken | May 24, 2025
"Would you like to see me naked? Not as a sneaked peek through my window blinds or through an open door... Completely naked, for several minutes, talking to you just like we are now. Would you like that?" You can't believe the offer and stammer out a yes. Anne smiles. "OK, Little Jimmy. Here is the deal. Today is Wednesday. Our parents leave for a trip tomorrow morning and come back Monday afternoon. If you obey me until Sunday at 6PM, I will give you a strip tease and a lap dance. If you arr REALLY well behaved, I will obey you from 6PM until Midnight Sunday and we will bpth be completely naked until out parents get home. Are you willing to do this?"

wanker-Jim | May 24, 2025
My heart races as I listen to my sister’s offer. Suddenly aware of how HARD my little erection is from Anne’s description; I quickly cover my boner with my hands. I am so excited, I quickly answer, “Yes Anne, I agee” , without really thinking it over.

nervousken | May 24, 2025
"Don't cover up, LittleJimmy" Anne smiles. She gets up and gets something from her desk, then walks to you. "Turn and face the wall" and she positions you carefully. Then, she places two playing cards on the wall. One held up by your nose, one being held against the wall by the tip of your cock. Your head spun as she positioned the second one. ANNE WAS HOLDING YOUR COCK!!! She stepped back and admired her handy work. "Thisnis to make sure you don't move away from the wall" she explained. She gently pulled yiur hands behind your back and handcuffed you. You seemed a little nervous, so she put something on a string in your right hand "That's a key, in case you din't trust me... now stay put" You stayed there, facing away from the bed, your nose and your cock pinning a pairnof playing cards to the wall. After a few minutes, you felt Anne standing close behind you and she held something up for you to smell... and the for you to see. "Recognize these? You should, they are your favorite panties. Feel how warm they are? They have been on me this entire time." She gently puts the crotch intonyour mouth and leaves you there on the wall for a long time. You begin to worry, but Anne eventually comesnup to you and unlocks the cuffs. "Mom and Dad will be here in a few minutes. Go get dressed. No underwear and no masturbating."

wanker-Jim | May 25, 2025
Still a bit confused, and very aroused, I look at my sister then takes her panties from my mouth. “I … Yes Anne … but Mom and Dad will see that I have an erection. Can’t I please at least wear underwear, Anne? Please?” AsI plead to be allowed to wear underwear, I am very aware that our parents will be home soon and that I am naked in my little sister’s room. As I hurry toward her door, I give one last plead before going to my room, “Can I please wear some underwear, Anne?”

nervousken | May 25, 2025
Anne smiles. "I'm not wearing underwear, either" You head down the hall, naked and hard, and get to your room just as the backdoor opens and yournparents come in. Safe behind your closed bedroom door, you try to make sense of the last few minutes. You had become your sister's slave and that made you nervous, but also turned you on. She didn't seem to want to ruin yournlife or hurt you. She was clearly turned on, her panties, your favorite pair, were so aromatic with her arousal. Your phone buzzes. It's a text from Anne. "SlaveJimmy, you have three choices. First, no underwear and you get a reward. Second, you wear your underwear and you earn a punishment. Third, you wear the bra and panties you stole from mynlaundry yesterday, red hipsternpanties and black bra. Don't take too long, Mom and Dad brought dinner and Mom will come tell you soon! Hurry up!"

wanker-Jim | May 25, 2025
1. Oh shit, I don’t know w what to do. I don’t want to be punished, and I want to be good for Aanne ,so MY underwear a rare out. I can’t go without underwear or Mom and Dad will see that I have an erection. Umm Anne’s panties? which one? Thjis pink flowery pair is weT ,and smells wonderful … these will keep me TOO damn hard. The red panties and black BRA? Shit I wish Anne didn’t know I took the bra, too. I take a deep breath and put on Anne’s red hipster panties and her black bra. They both fit tightly on me, but at least Anne’s panties keep my erection contained. I quickly put on a black tee shirt and a pair of jeans over them. I get dressed just intime, as I hear Mom knock on my door, for dinner.

nervousken | May 25, 2025
Anne is already at the table and smiles at you as you sit down. Halfway through the meal, she gets up for another drink and touches yoir back. You can tell she felt the bra strap. When she sat down, her eyes held yours and she shifted alittle, showing her hard nipples through the t shirt. She wasn't wearing a bra!

wanker-Jim | May 25, 2025
Anne showing me that she is braless really turns me on, and my boner makes my panties uncomfortably tight. … Was Anne still not wearing panties too? I shift, and pick at the panties creeping between my butt cheeks, then I pull the back of my shirt down, to make sure that my red panties don’t show. I can’t help but to blush and squirm a little, and look at my sister’s breasts, as we eat dinner, with me wearing my sister’s panties and bra, while she isn’r wearing any, sitting there with our parents. I realize that even now, Anne really is in control.

nervousken | May 25, 2025
After dinner, Anne sticks her head in your room. "Bra and panties? I had no idea what a thrill I would get knowing you were wearing that for me." She smiled. "Keepbthe bra and panties on and come to my room after our parents go to bed. I want to talk about this weekend and I want to make sure you are OK withbwhat I have in mind. By the way, I am not weating panties OR a bra" nd she goes to her room.

wanker-Jim | May 25, 2025
I am glad that Anne is having so much fun, and that she expressed it to me. Anne going without a bra or oanties gives me a thrill too. I was kind of dreading this weekend, but now I ‘m kind of looking forward To it. … Still very aroused, I adjust my pamties and br., I feel felief that Mom or Dad didn’t notice I was wearing them. That would have been hard to explain to them try tostay busy in my room, away from our parents, until they go to bed, and then go to Anne’s bedroom.

nervousken | May 26, 2025
You get a text from Anne "Don't play with your cock!"

wanker-Jim | May 26, 2025
,Yes Anne. I’m not playing with it, but Tt is still very excited. I’m just sitting in my room waiting for Mom and Dad to go to bed. I’m kind of bored. What are You doing?” … Then I send another text, “Your bra and panties are Tight. I’m glad that Mom amd Dad didn’t notice me wearing them. lol”

nervousken | May 26, 2025
"I am masturbating thinking about how much fun we will have this weekend"

wanker-Jim | May 26, 2025
I text her back, “DAMN, ANNE. I want to masturbate so badly too … but I won’t. I can’t promise that I won’t later tonight. Lol You making me wear your panties and bra like this makes me so fucking horny. … You not wearing panties or a bra at dinner was so damn hot, too.”

nervousken | May 26, 2025
"Promise me you won't mastutbate without my permission, SlaveJimmy"

wanker-Jim | May 26, 2025
“Anne, I promise that I won’t masturbate before going to your room tonight. And I promise that I’ll try my absolute best not to masturbate unless I have your permission after that. I’ve been so turned on today and tonight. You’ve go m e so turned on.”

nervousken | May 26, 2025
"You will be a good boy. I know you will."

wanker-Jim | May 26, 2025
My cock twitches and it stiffens harder when I read Anne’s text. Then reply to my sister, “Thank you Anne, you make me happy when you say that. Now I have more confidence that I can keep from masturbating. I’ll be coming to your room soon.”

nervousken | May 26, 2025
"Do you want me to still be doing this when you come in?"

wanker-Jim | May 27, 2025
I squirm much harder, thinking about seeing my sister masturbating. I eagerly text, “Fuck, Anne, that would be so fucking hot. i don’t know when Mom And Dad wi ll go to bed, but I’ll be there as fast as I can.”

nervousken | May 27, 2025
"Don't wait too long.. and don't forget to knock"

wanker-Jim | May 27, 2025
“Okay, I’ll change into a pair of shorts now, so I’m ready as soon as they go to bed.”

nervousken | May 27, 2025
"Oh no, SlaveJimmy. My bra and panties ONLY. You don't want to disappointnme, do you?"

wanker-Jim | May 27, 2025
Anne’s text scares the shit out of me, bot, I can’t argue … So, I text back,”Oh… Yes Anne. You make this had, you know. Mom and Dad are getting ready for bed now, I’ll see you soon Anne.” … Seeing Anne naked and masturbating is the only thing that makes me agree.

nervousken | May 27, 2025
Anne texts back a fireworks emoji

wanker-Jim | May 28, 2025
I laugh at Anne’s emoji. Just then I hear our parents getting up to go to bed.n Itext Anne, “Your emoji mad eme laugh, you make me happy . Mom and dad are going to bed now. I’ll be there soon.” I take off y tee shirt and drop my shorts at the foot of my bed, I go to my door, very nervous, and I poke my head out to make sure nobody is in the hallway. I take a deep breathe te ocalm my fears AND excitement.I go out into thehall, to see my sister. I hurry to geT to Anne’s room, then I gently knock on her door. I hope I knocked hard enough for Anne to hear it. although extremely nervous, I am also VERY aroused as I stand in frint of my sister’s bedroom, wearing nothing but her panties and bra.

nervousken | May 28, 2025
Anne calls out softly for you to come in. She is on the bed, covered by only a sheet. You can see the shape of her hand taking the vibrator from her pussy under the sheet. She smiles at you with a flushed face. "Damn, you are sexy in my undies" She looks at you hungrily, almost like she is trying to control herself. "OK, first, I have to cum while looking at you. Come closer" she beckons you to stand beside her bed and you can smell her lust sweat and arousal "Now, reach down and massage your cock over the panties" Her hand guides yours so you are gropping and rubbing your cock throighbher panties the way she wants "Now, take your left hand, putnit behind mybhead and grab my hair." you comply and she smiles "No, SlaveJimmy, grab a FISTFUL and hold my head down" You do and she inhales sharply and smiles hugely at you. Her hand and vibe move back to her pussy and she begins to masturbate fornyou. Her eyes alternwtely looking up at you in raw lust and down at your hand massaging your cock. Her hips buck under the sheet as pleasure builds, she pulls against your hand, but you grip herbhair tighter. Her leftnhand is massaging her breasts over the sheet, leaving damp wrinkles where she grabs them "Take the panties off" she says hungrily. You slide them down withnyournrightbhand and step out her eyes are locked onyonyour cock. "Rub itnon my face. Slap mybface with it." You pull her head closer and begin slappingbher face. You are shocked at the meaty impact and how she reacts. Her legs thrash and she tries to turn her face from your cock butnyou hold her hair and keepbher facong the slapping dick. Soon, she is cumming, her hand clmampedntightlynover her mouth to stay quiet. "Jesus, SlaveJimmy, that was amazing! Thank you so much. That was so sexy" She breathes deeply for a minute "Give me the bra and panties you wore." She puts them on under the sheet and smiles at your naked body and confused face. "It isn't Sunday, silly. Remember that you don't get to see me naked until Sunday" You start to protest, but she pulls the covers back to show herself in the bra and panties youbhad just been wearing. She holds the vibrator up "Want to taste?"

wanker-Jim | May 29, 2025
With my cock so hard that it hurts, I stare at her vibrator and I tell my sister, “Fuck, Anne, YOU are the sexiest woman in the wolrd. … Of course I want totaste you.” I Without touching It, my cock starts throbbing harder, as I look into my amazing sister’s eyes. Never in m life haveIwanted to masturbate and cum so badly, than I do right now. Because of my little sister, I MUST NOT touch my aching cock. … As I stand naked In front of my sister, I feel precum trickle down my erection, as I ask her, “How, umm how do you want to do this, Anne?” … I have never felt so desperately horny for anybody in my life. Yet, here I am, naked with my throbbing erection, standing naked before my little sister, waiting for her to tell me what to do … with my parents just a couple of rooms away.

nervousken | May 29, 2025
Anne reaches up and gently presses two fingers to your lips. Your mouthbopens slightly and they enter your mouth. Your tongue swirls around them and you taste her. Seeing your rraction, she smiles. "I was nervous you might not likebthe taste... or the smell. If you want more, the vibrator was deeper inside me" Do you want that?

wanker-Jim | May 29, 2025
Tasting my sister’s pussy makes me crave it even more. Yes Anne, Imay I PLEASE taste your pussy more?” I keep fighting my urges to masturbate. tasting her pussy juices as I see my sister’s smile. “I umm, you want me to lick t toff your vibrator?” I ask as I blush.

nervousken | May 29, 2025
"You don't have to, I just thought you might like to... " Anne blushed and looked away nervously "Plus it would be super sexy to watch" She lowers the toy to the bed "I'm sorry I made you uncomfortable"

wanker-Jim | May 29, 2025
Anne has me blushing too, bu tI give her a bug, genuine smile. “Anne, that was the sexyest thing that I have ever done, or seen. Fuck, ;d about anything to make you happy like th, Annet. I .. I think that it’s hot that my beautiful little sister is kinky like that, and that you included ME.” I go to Anne’s bed and pick up and pick up he vibrator and I lick it. “Fick Anne, J’ve always wanted to taste your hot little puusy. Maybe not quite like this, but I’ll take it,for now.” I then lixk her vibrator a couple more times, as my erection still throbs.

nervousken | May 29, 2025
Anne reaches over towards your cock "May I?" she asks looking up at you. You nod and she traces her finger through your precum and then tastes it. "I hope you let me suck hour cock this weekend" she teases "Oh, wait, you have to do whatever I ask... even if it's cumming in your sister's mouth" She motions for you to take a step back. "Are you ready to talk about this weekend?" She points at a stack of business cards she printed on the desk. "Those are yours. Each one is good for half an hour of owning me as your sex slave, there is twelve there for the six hours I promised you" She pauses as you read them. "Every time you are less than obedient, you have to give me one card" you look up in disappointment and confusion "Calm down, SlaveJimmy. However, anytime I ask for something challenging, I will give you more cards. The more challenging, the more cards I give you for doing it. Also, each of my friends that joins us will give you four cards, that's two hours, and you can earn or lose cards the same way. Does this seem fair?" she looks at you as you think for a second. "Tara is definitely joining and she has agreed to give you four cards eaxh day she joins us"

wanker-Jim | May 29, 2025
After listening to Anne, think for a moment, and then I smile at her. I am really excited that Tara will join us, at least part of this weekend. Tara being here might make it more difficult, but the only girl that I hat I have a bigger crush on than Tara, is Anne. With my heart beating fast, U try to answer my sister calmly , ”Yes Anne, that sounds fair. I especially like being able to earn cards back if I screw up, or disappoint you or Tara.” … J am so excited thinking about this weekend, I start to reach for my erection, even in front of my sister, before I stop myself. “ Umm Anne,” I say meakly, “Not masturbating tonight will be VERY difficult, especially after today, and tonight. So umm I still ptonise to try my best not to, but do you have any suggestions? You seem very sexual, and I always give in to my urges to jerk off.” I blush asking my younger sister about this.

nervousken | May 29, 2025
"I know that it may be difficult to play in front of other ladies, but remember that each one has offered to obey you for a few hours..." Anne looks up at you nervously. She gets out of bed and looks into your eyes. "I have an idea to keep you from playing withbyourself. It's really kinky... Do you want to try?"

wanker-Jim | May 29, 2025
. “I umm, Yes I’m willing to try your idea, Anne. I mean, it’s not just about collecting the cards, I want you to be proud of me, what’’s your idea, Anne? And how kinky is your help, Anne.? Before she can explain heer idea, I ask, “How many ladies, Anne? I mean, you and … and Tara are okay, I trust you both a lot.?” … As my erection gets even harder, I, myself, wonder if it is just because of playing with just Tara and my sister …or playing with other less familiar ladies, too

nervousken | May 29, 2025
Anne smiles. I invited my other close friends, the ones that I trust and that you can trust, too. And each one has agreed the rules I have. After this weekend, you will have the opportunity to have each and every one of the ladies as a slave. We can talk about the list tomorrow, OK?" Anne reaches into her desk and pulls out a card. "OK, if you agree to what I am going to suggest, you get another card... so you will have me as your sex slave for another half hour" She uts the card on the desk and then pulls out a box. "This is a chastity cage. It locks onto your cock and keeps you from gettingnhard or jerking off" She unpackages the cage and holds it for younto see. "The key will be on my necklace and you can ask for the key anytime after tomorrow when we get up. If I don't give you the key when you ask, I will give you two more cards and you will own me for another hour. May I put the cage on you?"

wanker-Jim | May 29, 2025
I look at Anne kind of fearful, I had heard of these things, butdidn’t know much about them. Looking into my sister’s eyes, and seeing her smile, I couldn’t say no. Besides I REALLY did want to keep my promise to her. “Okay,” I say, and I take a deep breathe. “You can lock that on my cock. I wan t to be a good slave for you,” I yell my sister.” Where did you get something like that anyway, Anne? And WHY?” J try to relax, and wait gor her to tell me who will put the chastity cage on my cock.

nervousken | May 29, 2025
"Before I lock this up, there is something I want to do first" and without warning, Anne takes your full length into her mouth, her nose ptessed into your pubic hair and her tongue on youe balls. She stays like that for a few seconds before sliding her mouth off of your cock. "Now you know that I can deep throat your cock" she says smiling as she quickly puts the cage on your cock, locking it and then standing up. "Thank you, SlaveJimmy. Now, do you have any more questions about this weekend?"

wanker-Jim | May 29, 2025
My sister has me so turned on and horny, I’m nearly shaking. I am so amazed, MORE amazed at how fucking sexy Anne is. Finally, I trammer, “Umm, when do we start playigin the morning? As soon as Mom and Dand leave? Umm, and Tara will be here in the morning? Will I be able to masturbate begore Sunday nigh? And will you have to put thus on me sggain?” … My mind is spinning from being so excited. Then I ask,”Anne?So9ld I go back to my bedroom now? And Ane? … Thank you for hekping me keep from masturbating. I want to be good for you.

nervousken | May 29, 2025
Anne stands up and kisses your cheek. "shhhh... relax" She gently rests her hand on your face. "Everything will be OK" she says reassuringly. She guides you to kneel in front of her and she sits on the bed, her long, slender legs filling your vision. "Please, massage my feet" she commands. As you begin, she starts explaining. "Tomorrow, everything will be normal. The only thing that will change is you aren't allowed any underwear. With the cage on, you won't have a boner for Mom and Dad to notice. Tara will come over early, before our parents leave. Once they leave, you will undress completely in the living room. Our game will begin at that point." Anne shifts to give youbher other foot to massage. "You ask about jerking off, but you need to stop thinking like that. If you focus on cumming in your hand, that's all that will happen. You will have me, you will have Tara... I have invited Eve, Beth and Amy, too. Every one of us has agreed to be your sex slave. Think about that. You can order each and everybone of us to have sex with you. Do you really think that pulling your cock for a minute or two is better than laying Tara down inyour bed, climbing on top of her and feeling her tight, wet pussy wrapped around your cock? Would you rather lay back on a bench in the park while Eve kneels down and sucks your cock until you cum in her mouth... or hide in the dark and jerk off into a kleenex" Anne smiles down at you. "I set this up so that you could relqx and enjoy serving us, knowing that we can't go too far because we all have to be your slaves after." Anne lifts your chin up wothbher toe so you looknher in the eye. "Are you excited?"

wanker-Jim | May 30, 2025
After hearing this, I am stunned. Looking into my sister’s eyes, I squirm noticeably as I smile enthusiastically up at her. “Fuck YES, I’m excited, Anne. You’re not only the sexyist woman in the woeld, you are the BEST sister on earth. I’m sorry that I was fearing the worst about being yourslave, and the other girls too. It’s just, umm having a little dick has always been a negative thing, so I thought that YOU … and Tara were making fun of me. You are so wonderful … both of you … AND your g[ri ffriends, too. I’m … I’m not just excited about you ladies being my slaves … but I’m really excited about being YOUR slave, and doing what I can to make you all happy. Thank you Anne … Umm You and Tara can call me “Little Jimmy” any time that you want to.”

nervousken | May 30, 2025
"Is there anything else before you go to bed, SlaveJimmy? Remember, no underwear tomorrow... in fact, why don't you take my t shirt with you and sleep in only that?"

wanker-Jim | May 30, 2025
Still looking up at my little sister, l lushh a little as I smile, “Yes, Anne, I’ll do that. Umm I don’t have to wear it in front of Mom and ad, ro I?”

nervousken | May 31, 2025
Anne laughs as you hold up her pink t shirt that says "BRAT" across the chest. "I thibk that woukd be hard to explain. If you want bottoms... you have my dark blue pantoes to wear, but you don't have to. Before you come out of your room in the morning, please put on something appropriate"

wanker-Jim | May 31, 2025
having fun . “Should I put it on here, or do I wait until I get in my room, Anne?” … I guess id I get caught in the hall, it would be better to be caught in the shirt, maybe they woulfn’t notice the chsdtity cagen if the shirt is long enough.wet2

nervousken | May 31, 2025
"I'll let you decide, SlaveJimmy" Anne watches and giggles when you realize the shirt barely comes to your belly button. "We are going to have so much fun this weekend." She smiles and climbs back in bed. "Oh, one last thing... Before you go to sleep, send me a text telling me anything that you want to have as off limits. Like us peeing on you or something" With the covers pulled up, Anne drops the bra and panties she had been wearing to the floor to tease you

wanker-Jim | May 31, 2025
I -accidentally let out a little moan as Anne drops her panties and bra on the floor. I have been so close to seeing my sister completely naked so much tonight. Lusti ng for her, I tell her,t. “Good night Anne, I love you” Then to show my sister that I am her willing slave, I slip her pink t shirt on before leaving for my bedroom. I put on Anne’s blue thong, to at least have something covering my chastity cage, though it still shows through it, abbvously. … Being unfamiluar with listing my l iliits, struggle with my text to my sister. “Anne here are my limits that you asked for. Peeing on my face, skat, public ex displaying, receiving anal sex, physical abuse, there may brothers that I’m not aware of.
… After texringmy sister, I have trouble getting to sleep, with my mind filled with the xement of tonight, and the anticipation of the next few days.

nervousken | May 31, 2025
Anne quickly responds "Scat, EEW NO!!! You being fucked in the ass... only from guys? What if a lady wants to peg you? Can we define 'public display'? You know we'll want to show you off some, but definitely within reason." As you thought about your response, another text came in. "Peeing on your face and physical abuse... I want to negotiate on. Are you willing to remain open to tryinh pee play if we are in a fun and respectful environment and we have a reward system in place? Physical abuse - I hope you trust I won't injure you or case actual pain. But I sooooo want to spank you and get a little rough. Can we negotiate for this? I love spanking but I've only spanked women... I am really looking forward to spabking a man and seeing what his cock does!"

wanker-Jim | May 31, 2025
“I don’t know what I mean by a lot of this either, Anne. I’ve never really done master/slave stuff. By abuse, yes I meant harmful. Spanking and stuff like that will be okay, I guess. N ot REAL pain though. I Kknow that part of this is to challenmge me and to test me, but I much about this, I’m a” virgin” at this sort of thing. By public difplay, I meant showing my chastity cage, or budity to others outside of us. Just keep everything legal, please. Lol I know that setting limits are important, but I don’t know what YOUR limits of doing things are either. I don’t even know what rhythm peeing is?? Thinking about YOU spanking me makes me blush, but is still basically harmless … I think. LOL I trust you and your friendsm Anne, and I will TRY to make you all happy, and proud of me. I assume that I may find some of my limits this weekemd? Please try to just stay “within reason”, although I know that that means different things to different people. I lofap9

nervousken | May 31, 2025
"OK. How is this? Any lady that wants to pee on you needs my permission. If I give her permission, she gives you another hour of being your sex slave, I give you half an hour AND you have the option of peeing on her in the same way she did you later. This will keep them from being too free with it and it will make me think twice before saying yes. As for showing you off... Let's take this on a case by case basis. If a lady asks you to display in a way you don't like, bring it up. Eachnof you will pick someone to decide. Those two will talk it over and make a decision and everyone will stick to that decision. Does this address your concerns?"

wanker-Jim | May 31, 2025
Yes, your ideas seem more than fair, thank you for being so understanding, Anne. You know, I’m still kind of nervous, but I guess that is part of the fun. I trust you, and your friends. In a way, I’m kind of looking forward to being your slave. Thank you, Anne.

nervousken | May 31, 2025
"Sweet dreams, SlaveJimmy!!! By the way, I will DEFINITELY peg you at some point. I will see you, ALL OF YOU, every inch of your body, tomorrow. I look forwarding to learning everything about you and your body" a few minutes later, she texts several fireworks emojis "Those were thinking about your face between my thighs"

wanker-Jim | May 31, 2025
I shift around uncomfortably, from my cock trying to expand in my chastity cage. Anne has me much more excited, than Nervous about this weekend with her. TARA, and ALL of Anne’s friends are all VERY sexy and fub, so I am excited about being their slave too. Thinking about beeng between Anne’s thighs and bringing fireworks dominate my thoughts now, though. Almost overwhelmed with desire, I text my sister a simple heart emoji with “Sweet Dreams, Anne” … This could be a hard night for me to sleep.

nervousken | Jun 1, 2025
You wake up, aware of a woman in your room. You jolt awake, think it might be your mother. You relax a little when you see it is Tara. Your mind freezes. "HOLY SHIT! TARA IS IN MY ROOM" your mind screams. Your body freezes as you see she is in bra and panties. This must be a dream. The beautiful woman turns to face you and smiles "Good Morning, SlaveJimmy" she says, smilng. God, that smile could melt an iceberg! She kisses you on the cheek and sots on the bed. "Your parents are still asleep, but I couldn't wait another second to start our game" she says softly. "Do you mind if I climb under the covers?" it's a command, not a question and the beauty of your dreams slips under the sheets and presses her firm ass to your chastity cage. She pulls your arms around her and you inhale her intoxicating perfume. She nuzzles against you and your head spins. "Anne and I have wanted to do this for weeks, but we had to wait for your parents to go on vacation. I hope you don't mind us surprising you with this" You can't speak, you are afraid of dping anything that might break this magical spell that has your dream girl in your bed. Tara turns and smiles at you "Before we get started, can you do something? I have to know that you are doing this completely willingly. I can't imagine doing this if you aren't completely on board." She pauses and takes a deep breath "I mean, I know you are nervous, but so am I! I mean... I've never had a man as a slave before... and I've never promised to be a sex slave before to anyone. Please... tell me that we are actually doing this and that you WANT to do it. Can you reassure me of that?"

wanker-Jim | Jun 1, 2025
I fight to control my squirming as I gently give Tara a hug. Being so nervous that my mouth is dry, I answer my dream girl, “Yes Tara, I am willingly offering to be your slave. I want to be Your slave, Anne’s slave, and your lady friends’’ slave this weekend. I look forward to serving as your slave to Anne, You, and the other ladies.” Nearly trimbling, and feeling a bit overwhelmed with nervousness, excitement, antu9upation, and PASSION … I gently kiss Tara on her bare shoulder.

nervousken | Jun 1, 2025
"Thank you, SlaveJimmy, that means a lot" Tara turns and kisses you on the lips. "Have you ever touched a pussy before?"

wanker-Jim | Jun 1, 2025
“Oh … umm … no, Tara” I blush hard and squirm, as I stammer, “How umm How did you know, Tara?” I am so embarrassed that I feel like I might explode … Yet I still feel closer and more turned on by Tarara than I ever have.

nervousken | Jun 1, 2025
"Don't be embarassed, SlaveJimmy" Tara takes your hand and guides it into her panties. She shifts a little to give you easier access. "Do you want the first orgasm you give to be to me... or another lady... or Anne? Be honest"

wanker-Jim | Jun 1, 2025
“I … I’d love it to be you or Anne, Yara,? “ I tell her awkwardly. “I … I guess that you know how I feel about Anne? And about You, too? … I umm helped Anne have an orgasm last night.” I tell Tara meekly, but also with some pride. I realize that I am genyly rubbing Tara’s possy as I am telling her this. “I have always thought of you or Anne most when I unn … you know. ”I realize what I just told this beautiful woman, and I blush harder and stop rubbing her pussy. So, I try to conyinue to answer Tara’s question, “ I think, uh … Idon’t know, do you think Anne would be disappointed if I gave you an orgasm first, Tara?” I become very aware how hard I am squirming, with my chastity cage rubbing against Tara.

nervousken | Jun 1, 2025
Tara takes your hand and pulls it up from her pussy and places it on her breast. "SlaveJimmy, I think it is cute and sweet that even now, with me throwing my body at you, that you care more for MistressAnne" She pauses for a moment "You should save your first given orgasm for her. She will like that." You realize and Tara's hand is down at her pussy. "SlaveJimmy, you jerk off thinking of me a lot. I want to hear you talk about what you fantasize about while I masturbate"

wanker-Jim | Jun 1, 2025
“God, Tara you weren’t vcev suppose to know that I masturbated because of you.” I laugh and about doing about everything with you. Kissinf,making out, caressing your body … eespecially your tits I love your sexy blush a little. As I alternate looking a tTara’s h and, and at her eyes, I quickly continue, “Okay, I’’ve masturbated MANY times thinking about you. I’ve fantasized little tits, Tara. veryTHing about you is so sexy. Umm I’ve fantasized about fucking you, fingeringyout pussy, licking your pussy … about everything. You …Imean, with you and Anne around me so much, I’m always honey, Tara.

nervousken | Jun 2, 2025
"Hold me tight, play with my breasts and tell me a fantasy while I masturbate and cum..." Tara pushes her butt back agaisnt your cage and you nuzzle your mouth to kiss her neck

wanker-Jim | Jun 2, 2025
Laying in my bed, a nd holding Tara like this is practically a fantasy come true. As I love fondig ttra’s sexy little tits, I get so horny watching my fantasy girlfriend, , masturbating beside me. , begin my masturbation n fantasy. “I fantasize about being naked with you, Tara. We kiss abd make out as I fondle your hot tits, passionately kissing and caressing each others bodies. After making ou f or a while, I kiss your cheek, and then your jaw, and doen to your tender neck. Kissing and sucking on your neck, I give you a Hickie. Nxt I kiss down your chest, to your hoT little tits. Oh god, I think your tits are so sexy. I suckleone tit while fondling the other. I get so hard pressing my lips on yzour breast as I fently nibble your nipples. Mmm I could suck on your tiTs for hours. As a continue kissinf down your body, across your sexy toned tummy. Kissing down toyour waist, then to your wonderful pussy. As I liss your pusssy, you grab the back of my head, and press my face against your pussy. Instintively, I start licking and tonguing your wet pussy. I hear you moan loudly as you grab my hair, keeping my mouth against you pussy slit.I passionately lickand penetrate your pussy with my tongue. My cock is throbbing hard as I grope your ass, wanting you so badly. Looking up at your eyes and seeing your smile, makes meknow that I belong here. I tongue your sweet pussy and gently suck on your pussy lips, bringing you to several orgasms. My cock is rock hard and throbbing the whole time I am pleasuring yout amazing pussy. Still holding my hair, you slowly raise my head, and bring me up your body. You tell me that your tits need more attention. I suck and fondle your titsm until you are moaning in pleasure again. Again, you slowly pull me up your body, then you reach down and hold my stillthrobbing cock,and slide it into yourpussy.” … Iwhimper as I begin kissinf Tara’s neck and shoulder agai, with my cock cage pressing against her. “Oh god, Tara, I love you, I want you so much. I’vealwayswanted you, Tara.” I whimper as I passionately kiss Tara/z shoulder and neck.

nervousken | Jun 2, 2025
You feel Tara's body tremble against yours as she cums in your arms. As her tight ass pressed and shakes against your cock, you feel it. And so does Tara. You orgasm, while soft and in the cage, on Tara's perfect ass. "That was perfect. I really enjoyed that" she whispers. You are completely speechless. "You need to clean up your mess" and she rolls onto her stomach. You realize now that she had pushed her panties to her knees and you had cum on her bare ass. On the firm, round cheeks... and between them. "Clean me with your tongue, SlaveJimmy. And din't dare taste my pussy." and with that, she lifts her hips a little to present her naked ass to you and she reaches back to spread her cheeks a little.

wanker-Jim | Jun 2, 2025
Holy shit, that was amazing … But now she wants me To lick my cum off her ass? t first I want to resist, but this is TARA. Being aware that my parents are home, andmight wake up at any time hastens my decision. I’m still FULLY horny as I look ay Yara’s assand asshole. It feels likeI amshakingas I get to my kneesbehindTara. I close my eyes and lick my cum off her right butt cheek. After the firslick, I know that Tara won’t let me stop mow. Xtremely embarrassed, I finish licking off her butt cheeks, and I see there is still a mess between her butt cheeks. I place my hands on Tara’s hips, and push my nose and mouth jnto her butt crack. Something … somehow I find this very erotic and kinky. With cum smeared on my face, I lickthe cum from Tara’s butt crack and butt hole more eagerly than I had intended. Upon finishing licking my cum from Tara’s ass, feeling shameful, I sask “I hope that is good enough, Tara?”

nervousken | Jun 2, 2025
Tara pulls up her panties and climbs out of bed. "I need to get back to Anne's room, I don't want your parents to catch me in here.." Tara pulls on one of your t-shirts, it comes down long enough to cover her, but short enough to be sexy as hell. "SlaveJimmy, that is MORE than good enough. Your tongue on my asshole shocked me... not just that you did it or that youndid it so eagerly... it's how amazing it felt. I've never felt that before and I never imagined how incredible it could be" Tara pauses and sees your shame. "Here, these are yours" and she slips her panties off from under the shirt. She hangs them on the headboard abive your pillow "Please don't be ashamed. What you did was so sexy and felt so good and was so unexpected. You are a wonderful slave and you should be proud." To drive the ppintnhome, she also slips thw bra off and hands it to you. "One thing, though. You need to tell Anne that you came. Tell her why you came, what you were doing and what you did to makeup for it. You should text her now" Tara steps a little closer and pulls your hand to her pussy, guiding two fingers into her. She bites her.lower lip and then backs away. "Be proud of your willingness to serve, SlaveJimmy" abd she steps out, closing the door behind her. You lay in bed for a few minutes, your mind trying to process what happened. If it weren't for the panties in your headboard... the bra in your hands... the taste in your mouth... the glaze of her arousal on your fingers... the perfume in the air... Younwould have sworn this was all a dream. But it was real. Tara mastuebated and orgasmed in your bed. She had, unintentionally, made you cum on her perfect ass. And you had given hour very first rimjob while cleaning her. Your cock ached. You quickly picked up your phone to text Anne.

wanker-Jim | Jun 2, 2025
Knowing that Anne and Tara WOULD talk, I tried to give ny sister as much hentail about what just happened as I could. Asr, I found myself getting really turned on, again. As I type the tect to m y sister, I even take Tara’s panties off the headboard and put them on my upper chest, so I could smell them while I text Anne. Somehow, weirdly, it felt right to share with my little s all of the details about what we just experienced. As Isend Anne the text Ieel both excitement and sham,and a little bit of pride. … Ilick my fingers clean, and wipe my sperm off my face, and then I send my sister a second text, “I REALLY want YOU to be the first girl That I make orgasm, Anne.”

wanker-Jim | Jun 2, 2025
… After thinking about it, I text my sister again, Anne, I am sorry for cumming this morning without your permission. I didn’t even know that I COULD cum with my chastity cage un, bot I did, I am very sorry, Anne.”

nervousken | Jun 2, 2025
"Bad Boy!" is all she replies with

nervousken | Jun 2, 2025
After a restless night, you are woken up by a text from Anne. "Get up! Mom and Dad are up and getting ready. Put on your cargo shorts and a clean t shirt. Don't tuck the shirt in like a dork. Put Tara's panties in your front right pocket.
Come out as soon as you can."

wanker-Jim | Jun 2, 2025
I quickly get dressed as my sister instructed. I know Anne doesn’t want me to wear underwear, so I slip on my shorts and t shirt. I smell Tara’s lovely smelling panties before I put them in my pocket. Thrn I hurry out of my room, to tell our parents.

nervousken | Jun 3, 2025
You get to the kitchen and you are surprised to see Anne's friends in the kitchen eating breakfast with your parents. Anne, Tara, Eve, Beth, Amy and Chrissy are all there. You get a little lightheaded at the reality that this is all real and soon, very soon, you would be humiliating yourself in front of six of the most beautiful ladies at school. Mom notices your look, but mistakes it. "Now, Jimmy, don't be mean to your sister and her friends. I told Anne that they could all stay over all weekend, but no wild parties." You nod, your mouth is dry and you can't speak. "Hey, I have an idea, why don't you invite your friend, Jeff, over?" Mom suggests. Chrissy gets a huge smile on her face and Anne quickly agrees. "Yes, LittleJimmy, invite Jeff over! We will order pizza and have a pool party" At that, your dad hands you some money "For the pizza." and then quietly so only you can hear "And, it w
might not be a bad idea to try flirting with some of these ladies. The practice will be good for you" At Anne's continued insisting, you text Jeff, inviting him over and tellhim him who all is there. Before Jeff gets to the house, your parents leave and the tone changes completely. "Ladies, let's all go to the living room" Eve says. "SlaveJimmy, please put the dishes in the dishwasher, wipe the table and then join us in the living room. You have six minutes."

wanker-Jim | Jun 3, 2025
Wow, Eve doesn’t waste any y time telling me what to do and taking charge, and somehow, that really turns me on.. … I wonder, do all of if Anne’s fruends always call me “little jimm, ,even inf ront of my parents? Even Mom is calling me Jimmy, now. … I text Jeff and told him the girls that are here, and he said he’d be as soon as posiuble. … As i rinse off the dishes, and clean the table, I get even more nervous. ALL of these ladies are so fucking hot, and w’lll lbe so humiliated all weekend for all of Them. … Nervous energy helps me get all of the cleaning done quickly, and I enter the living room to join the ladies, in just under five minutes.

nervousken | Jun 3, 2025
Eve looks at her watch in mock irritation. "You are seventy five seconds early SlaveJimmy" Eve walks to get a chair and sets it in front of the couch. "Please come here. You will get 75 spanks on your bare butt. Eve sits down and you stand in front of her. She reaches into your pocket, making sure to gently massage your balls before firmly gripping your cage. She smiles up at you, those beautiful green eyes framed bybthat jet blacknhair melt you. She pulls Tara's pantoes from your pocket. You blush as Eve unzips your shorts. You swear you saw her lick her lips when she caught a glimpse of your cage. Without displaying your cage, she positions yoi actoss her lap and then gently lowers your shorts to expose your ass before puttinf Tara's panties in your mouth. She quickly administers 20 swats before Beth says she wants to spank you. Eve stands you up, your butt to the other ladies and adjusts your shorts so the cage is covered. She smiles up at you "Let's keep that covered for now, OK? By the way, that is sexy as hell..." Beth takes Eve's place. Eve takes one last playful swat at your backside and whispers "You have a very nice butt, Jim" Beth pulls you into her lap without the same teasing and flirting Eve had and lays on thirty spankings before Amy takes over and finishes. "Now that is over..." Anne says "... I am sure that SlaveJimmy will be more precise when following instructions" Anne zips your shorts back up, after pulling them back up. "Before things get too intense, I want to make sure that everyone kmows the rules." Anne goes over the plan for the weekend and the reward / punishment system. "Now, a few last minute changes I am making. First, under no circumstance will another man fuck SlaveJimmy's ass. If any lady asks for it to happen, she will get a caning in front of all of us AND she has to be SlaveJimmy's sex slave for twenty four hours" The ladies looked at each other in shock at this, apparently, theybhad previoisly talked about SlaveJimmy being fucked and this was a surprise.. the punishment for asking for it was shockingly brutal. Anne smiled "Hey, he's my brother and I have decided he's not getting fucked in the ass. That is final." Suddenly, you realize just how much you can trust Anne. She not only took your request seriously, but she made it a hard limit and made it seem likenit was completely her idea. "Also, peeing on him is not allowed. As for corporal punishment, soft implements only. Canes, paddles, brushes and you need to have my permission. Nobody is leaving bruises on my brother." With everyone in agreement, Anne sits down woth the ladies and asks "SlaveJimmy, please give us a sexy strip tease... but first, take those panties out of your mouth."

wanker-Jim | Jun 3, 2025
I an so grateful and proud of my little sister for respecting my limits and protecting me. My admiration for Anneaways keep growing, and SHE gives me motivation to always tRy my best this weekend.Although I will be put in compromising situations, I want her to be proud of me. I take Tara;s panties fron my mouth, I don’t know what to do with her panTies, I keep them in my hand. SinceI don’t have many clothes on to start with, I realize that this will be a lot more teasing than stripping. I start by swinging Tara’s panTies avove my head, and shaking my rear at the ladies. Soon, I Take my shirt off and swing my shirt in one hand, and Tara’s panties in the oyher, until I throw each into the crowd of cheering ladies. Unzipping my shorts, I pull them down in back, and wiggle my red ass at my new fans. I make sure to wiggle my ass in front of ve, since she said I had a nice butt. While blushing from embarrassment, I am glad To see the ladies having fun. Before I drop my shorts completely to the ground I make eye contact with Eve, since she kept my chastity cage covered instead of exposing it earlier. WhenI drop my shorts the ladies all laugh and cheer seeing me in just my chastity cage. I am so embarrassed by now i just stand there blushing, naked except for the chastity cage my sister put on me.

nervousken | Jun 3, 2025
Now it is Chrissy's turn to take charge. She stands up and walks to you and hugs you, her large breasts press into you and are surprisingly firm. "What was are going to do first might be pretty humiliating, but it's really important because it will let all of us get to know you a little better." You look nervous and Chrissy smiles. "Each woman here needs to know how you fantasize about her. So, we will undress to our bikini and sit in a chair. You will then kneel down in front of her and tell us a few things. First, the most recent time you jerked off while thinking of her, what you thought about when you did. Then you will tell us one thing you hope that woman won't have you do and something you hope she does.... Who knows, maybe you will get lucky and she'll do it!" You get really nervous but realize that this cpuld be very fun, too. Chrissy slips off her shirt and shorts, revealling a body far more toned and muscular than you had imagined. Her blonde hair and blue eyes complimented her dark purple bikini. Her breasts were easily the largest of any of the ladies, but their shape was incredible and they had almost no sag. She sat down and let her legs spread a little more than normal. "Please, SlaveJimmy. Tell me the last time you masturbated thinking about me... and what you thought about... and what you hope I do and don't do to you this weekend..."

wanker-Jim | Jun 3, 2025
I hesitate and I look at hristy, when I am getting to my knees before, I admit, “You know, you’re right. Thus us hard … or at least hard to admit.” As I settle myself at her knees, I say,”Okay, I hope you don’t think this is weird, but when I fantasize about you, it usually has todo with sports. My last fantasy about you, we played on a softball team together. After the game, you and I went into The same lockerroom and took a shower together. I don’t know where the rest of the teamwas. * I laugh a little* So, we are both in the shower, soaped up, and we start playing a little grab-ass and grab-tits. We areboth so slick from the dosp that we keep slipping awat from each other. We wind up wrestling a litttle and we wind up on the shower floor … the nI I tit fuck you in yhe shower. I umm, I hope it doesn’t disturb you, but my fantasies about you al,ost always involves some sports, Christy.” “Okay, what would I like you to b=not do>Itake a breathe,”Okay, what would I like you to notdo? Umm I guess to physically dominate me. I mean, I don’t think you’d want To hurt me or anything, but physically restrain me,and physical challenging me, I’m not sure that you wouldn’t win. … What would I ;ike you to do?HMmm maybe just kuss or make out. Explore each other’s bodies … or us treally talk, and get to know each other. I guess what I mean is to discover you as a sexy young woman , not just as an ate. I realize that this is just a “ME” Thing, but I am usually ttracted to slinder, or smaller women.” I pause and take a breathe agaun, and still looking up into Christy’s eyes, I ask, “Is that what you were thinking of, Chrust?"

nervousken | Jun 4, 2025
Christy stands up and squats down in front of you. She kisses you deeply and then smiles at you. "You did great, SlaveJimmy. How do you feel having shared that?"

wanker-Jim | Jun 4, 2025
“Wow, that was a WONDERFUL kiss.” Then I softy smile at Chi0sty and tell her, ”. … I feel good, Cristy. It came out better than I thoughTit would. I … Sometimes it is hard to share things That I feel guilty o rashamed of.” My smile grows as I continue to look at Christy, ‘hank you for trusting me, and for pushing me to trust yzou and the other ladies here, Crhisty.”

nervousken | Jun 4, 2025
Eve steps forward. She has always seemed like the boss of Anne' and her friends. She is slightly shorter than the others, but her demeanor and posture make her seem for taller than she is. Her dark brown hair is straight ad silky, long enough to easily cover her breasts. Her eyes are a dark green, with a ring of gols on the outsode edge. Her smile and laugh are amazing. She slips out of her clothing to reveal a dark green strapless bikini. She stares into your eyes as she intentionally and purposefully adjusts her bikini, giving you a glimpse at more of her breasts and you swear she flashed her pussy for half a second. Her legs are perfectly muscular, not as powerful or defined as Christy's, but definitely shapely. Her whole body screams "gymnast" with the no fat, petite size and effortless grace. She sits in front of you and leans back confidently. She smiles casually as you nervously take in her body as if for the first time. "OK, SlaveJimmy, nw thatbyou have had a good, long look" she says with a hint of tease in her voice, let's hear it about me. Inwant to hear about the last time you held your hard cock and dreamed of me. I want to be impressed."

wanker-Jim | Jun 4, 2025
Just watching Eve has me squirming, as I kneel down in front of her. Eve has always intimidsted me a little, not physically, but because of her demeanors and her popiliarity. My eyes track up her sexy body, ro her lovely face, and I immediately get lost in her beauztiful eyes. After taking a moment to try To compose myself, I finally speak, "Umm ve, I know we haven't daTed or anything, but I fantasized That we were at a party together. During the party, you took my hand, and you led me to a bedroom. We undress each other while making out. Then when we get to the bed, you push me backward onto the bed, on my back. Afer kissing and playing with each other some more ... umm you get umm you start riding my cock. You umm your body bouncing on me, while I fondle your tits." ... I stophere. Squirming and blushing, I look at the floor. I feel nearly paralized from embarrassmentand shame.

nervousken | Jun 4, 2025
Eve has an almost sad look onnher face. "Why haven't you ever asked me out?" You look up in shock and she realizes her mistake. She smiles warmly at you "Thank you, SlaveJimmy. Now, I believe you need to tell me what you hope I do to you and what you hope I don't do..." She adjusts her position a little and you just stare at her thighs and the way they move.

wanker-Jim | Jun 4, 2025
Still struggling from embarrassment, I softly answer her, " I was afraid That you'd say no”." d say no" Realizing that they had teared up, I wipe my eyes. Still feeling encouragement from Eve’s encouragement I continue. "Okay, what I hope you won't do? ,,, I guess tha t I really have a fear of rejection from yo,u, Eve. I ... I hope yoou won't give up pn me??? And what I hope you will do ... umm I really felt special when you played with my balls and my chastity cage earlier. I hope that you enjoy doing that more this weekend?" I kind of laugh.

wanker-Jim | Jun 4, 2025
… Before I get off my knees from in front of Eve, I think … SHE asked why I never asked her out ? HOLY SHIT , she Wasn’t offended about my fantasy. … MAYBE she even wanted something like that ??

nervousken | Jun 4, 2025
Eve smiled. "I promise you that I will be handling your balls a LOT this weekend" Amy gets up and begins to strip to her bikini. She is the youngest person in the room, having turned 18 two months ago. She is also probably the lest interesting. Sure, she is cute, but she never has anything intereating to say. She usually just agrees with Anne or Eve and doesn't do too much to challenge the status quo. Looking at her, even her body is unmemorable. She's got just a little flab, but not enough to be unattractive, but nine of the muscle tone or strength of the others. He breasts are larger, but not as large as Christy's and certianly not as firm or shapely. Her brown hair and brown eyes do nothing to set her apart from the crowd. Her bikini is a hawaiian print in red with white flpwers. Just as she is about to sit in front of you, the doorbell rings. Eve and Christy get up. "That must be Jeff. Please, comtinue. We'll make sure everything is OK before letting him see you." and they head off. Anne asks directly "SlaveJimmy, if you would like to pause for a few mimutes, we can. If you want to pause until you kmow for certain Jeff is OK with this, please cover with a towel and we'll figure it out. Or, if you trust Chrosty and Eve... please continue.

wanker-Jim | Jun 4, 2025
Hearing Anne’s offer comes as a big relief to me, my sister comes to my rescue again . This is very stressful. I get a towel and wrap it around my waist, at least I don’t have to greet Jeff mostly naked. “Yes, I could use a glass od water, too,” I say. As I go to the kitchen, I signal to Anne, hoping that she will follow me so we can quickly talk. … Also since I rarely fantasize about Amy, this gives me a little time to come up with a fantasy about her.

nervousken | Jun 4, 2025
Anne comes in and hugs you. "You are doing great. This is serioisly hot!" She playfully pulls the tpwel away, leaving you naked. "Don't worry about Jeff. Eve and Christy will have everythibg under control." Anne looks a little mischevious.. so, you gave Tara a rimjob last night? How was that? She has an amazing ass, doesn't she?"

wanker-Jim | Jun 4, 2025
I blush and smile a little, “Yes, Tara does have an amazing ass. AND Anne, last night I told Tara, umm that I’m a virgin and I want YOU to be the first girl that I give an orgasm, can we make that happen? Please? … ALSO Anne… you forgot to take my chastity cage off this morning. You promised that you’d take it off right after our parents left. … Oh, and one more thing. What does Amy like? Blowjobs, or what? I haven’t fantasized about her much.” I take a long drink of water while I wait for Anne to reply

nervousken | Jun 4, 2025
"Hey! I didn't forget to take it off. I just thought this would be more fun with itnon!" Anne holds up the key "Besides, I promised to take it off when uou asked and you haven't asked." She lets the key drop back down on the necklace she is wearing it on. "Jim, seriously, though. Inwill take it off if you ask. But can you not ask until after lunch? Please? Trust me, you want to wait..." Anne bites her lower lip. "OK, until after lunch, that's about five hours. Inwill give you another hour of me being your slave. And Tara will, too. I think the other four will do the same, but for every ladybthat doesn't, I will give youbtwo more hours. Will you please not ask me to take itnoff until after lunch?" You pause "And you can choose how to lose your virginity tonight"

wanker-Jim | Jun 4, 2025
I look at Anne, and I am stunned by her offer. Then I smile at my sister, “Anne, I wan’t trying to get more out of you, besides, all those girls know that I let my sister lock my cock in a chastity cage, already. So, I’ll keep the cage on until after lunch jf … IF you promise to try to make sure that YOU are the first woman that Igive an orgasm to . I guess I can stand to keep it on for a while longer. Besides, umm some of the other women seem to like the cage too.” I blush, and smile at my sister again, “Do we have a deal?”

nervousken | Jun 5, 2025
Eve comes in. "Jeff is cool to play. Jim, are you OK? I will ask him to leave if you aren't..." She takes your hand and squeezes it. Anne nods "It's up to you, Jim"

wanker-Jim | Jun 5, 2025
I swallow hard as fear ushes through me. I know the women think that Jeff being here is a good iea. They have been right about Today so far…and I assume that Eve squeezing my hand is a sign of encouuragement. My heart is racing as I look into ve’s eyes, then into my sister’s eyes. “Okay” Isay with a dry mouth, even after I just drank some water. “I’m okay Anne and ve. Can I keep the towel on until we get out there.” Can I gently sqeeze ve’s hand for support before starting back to the living room.

nervousken | Jun 5, 2025
You get out to the living room and Jeff is sitting on the couch with Christy. He smiles and says hello. Christy speaks up "I got Jeff up to speed on what we are doing and he's promised to follow all of our rules." Jeff nods and smiles "Thank you for letting me stay, Jimmy" Amy takes your hand and leads you to the chair and sits down, and motions fornyou to remove the towel and then kneel. "Where were we, SlaveJimmy?"

wanker-Jim | Jun 5, 2025
Nearly shaking, I think about running out, but then I look around at everybody and I convince myself that I trust them. Slowly I reach to my towel, and I let it dropto the floor. Without taking my eyes off Amy, I kneel in front ofher, blushing so hard it felt like it burnt."I... I am going to tell you my fantasy about you, Amy. " Still lookingonly ay Amy,I begin. "I have fantasized about going to the lake to go swimming. You look hot in your bikini, but we soon begin skinny dipping. Thid leads to us plkissing and playing with each other's bodies. Soon, a few other people ahow up and we decide to leave. While we'restill in the water we put our awimsui back on. Then Then we walk to the lake shore holding ha Afterwegetout of the lake, you pull down my pants andgive me a blow job evem though other peoplemight see us."... Still blushing hard, I pause before contueing, "Okay, today, I hope that you don't hit or squeeze my balls too hard today. And I hope thatifyou go swimming today, that you will goskinny dipping naked." Too afrais to look at jaff, or anybody, I keep my eyes on Amy as Iwait for her response.

nervousken | Jun 5, 2025
Amy leans forward with a smile "You know, I have never been skinny dipping or given a blowjob" she whispers quietly into your ear. You look up at her in shock at her admission. "I'm not opposed to trying..."

wanker-Jim | Jun 5, 2025
Amy’s confessiom was totally unexpected and actually came as a great relief to me. Smiling, I lean forwardher and I place my arm across her back. Whispering, I tell Amy, “They a

nervousken | Jun 5, 2025
With Amy feeling a little better, it's Beth's turn. The red head has very unusual blue eyes and a very shapely body. More curvaceous than Anne and Tara, but not as much as Eve. You had actually gone out withbher a few times last year and made out some and had gotten her topless once. She undressed to a very provocative black bikini and sat across from you. The reached over and cupped your balls. It wasn't a sensual grab, more outnof curiosity, as sge wanted to know what they felt like. She gently rolled them in your hand and a feeling of warmth spread across your body. "This will be a great weekend" she says, smiling and anxious to get started. "You look really good, SlaveJimmy. I likenyou naked." She releases your balls and leans back. "OK, SlaveJimmy. Tell me how you masturbate to me. And then what you hope I do and don't do this weekend. Ibhave a lot of ideas and hopefully they align"

wanker-Jim | Jun 5, 2025
Feeling Beth touch on my ballsmake me squirm, and I even whimper a little. I wanted sex with Beth so badly, but she wanted to take our relationshipslow. I kneeldown in front ofBeth. I am tenseatfirst, but seeing her so intimately again draws my feelings for her out again. “Beth, I’ve tried toavoidthinkingabout you when I umm when I masturbate, but sometimes, I can’t help myself. I know that you like camping, so I’ve fantasized about going to a remote cabin with you. We rubnaround naked, even outdoors.


I can’t keep myself from squirming a little the entire time Beth is touching my balls. I knffldown andlook up at her. As I look up into her eyes, feelings come rushing back intomy mind. “Beth, I’ve tried to keep from thinkingofyouwhenI umm when I masturbate, but sometimes I can’t help myself. Hen U masturbate over you, I often times think about the weekend trip that we talked about, but never went on. I imagine us getting naked as soon as we get in our hotel room. We remain naked all weekend. We are naked, rolling around in bed together, kissing and hugging and fondlingeach other. As we roll around you get on your hands and knees,and I fuck you doggy-style.As we lay in bed, exhausted fron the sex, you reach down and get my cum on your finger, and you suck the cum off, in front of me.” I look up at Beth, andgive her asmile, still wanting her. BEFORE I CONTINUE, u HAVE AN URGE TO CONFESS, “Umm Beth, umm when we were dating, umm, I umm borrowed a couple of your panties, too.” I blush, but I keekeep eye contact, looking up at Beth. … “Okay, what I hope that you don’t do? U hope that you don’t try to get too much revenge on me for our us breaking up? … And what I hope you do? Umm It felt good when you rubbed my balls, so I hope you like playing with them this weekend, too.” I laugh and then give a BIG smile at ve.

nervousken | Jun 5, 2025
Beth smiles "Oh, yes, I will be handling your balls a lot this weekend. As for revenge... please don't worry about that. This weekend will be fun and revenge is not fun at all." She stands up and Tara takes her place. Tara has already undressed to a pink string bikini. "I know the last time you came for me, but I think everyone else would like to hear..."

wanker-Jim | Jun 5, 2025
Tara’s instructions frighten me a lot. I had planned on telling about the last ime I masturbated for her, notlast night. Someof the lsdies may have heard, but Tara has ME telling themall. I look into Tara’s eyes to steady myself. “okay, umm well, earlier last night,Anne put a chastity cage on me,so I wouldn’t masturbate. Later in the night, Tara came in my room, and she got in bed with me.” I pause to collect my thoughts. ? Tara umm let my touch her pussy, by guiding my hand down her panties. It, it felt so amazing. Tara offered to be the first womanthat U made cu, but umm I told her that I umm wanted ANNE to be the first woman for me to make cum.Umm Tara let my caress her body and her tits, while I told her what I think about whenI masturbate to her. It was a very hot fantasy about kissing her body, eating her beautiful wonderful pussy, and suckling her sexy little tits. Umm at the end, U describes hot I wanted to fuck her. Umm My chastity cage and Tara’s beauTifuk ass werepressed together the entire time. When my story was about over, I was squirming so hard, and when Tara wiggled her ass, I shot cum all over her wonder butt … even though I was in my chastity cage. Umm After I made my mess, Tara had we lick it all clean. Umm I licked my cum off her butt cheeks first, and … and then I licked my cum from between her butt cheeks. … When I text Anne about it, my sister said I just performed my first rimjob.” I blush and squirm as I tell all the ladies, and Jeff about last night. “Umm is that good enough, Tara? I am so embarrassed that I nearly have tears in my eyes. … But I am extremely turned on, too.

nervousken | Jun 5, 2025
Tara smiles. "That was perfect. Youbleft out how much I loved thatbrimjob and how amazing you are as a slave" Tara pulled her top to show her breasts to you for a few seconds. "Now, what do you hope Inwill do and what are youbafraid of me dping tjis weekend?" before covering her tits back up

wanker-Jim | Jun 5, 2025
Seeing Tara’s breasts drive me crazy, and help me immediately get over my embarrassment of having to tell everyone about last night. “Hmm what I hope you won’t do . I hope you don’t umm use restraints or other kind of bondage on me too long? … And of course U DO hope that you let me see, and fondle, and suck your sexy tits a lot this weekend, Tara.

nervousken | Jun 5, 2025
Tara stands up and presses her breasts into your face "Like this?" After a few seconds, Tara pulls back. "OK, this will be really hard and you can say no. But... I hope you'll do it. For us." She beckons and Jeff pullsbhis shirt off and sits in the chair. Everyone is silent and hanging on your next words. "Anne smiles at you and nods. "If this is too much, you can say no" Tara getsboutnof the way so you can kneel in front of Jeff. If you say yes

wanker-Jim | Jun 5, 2025
stand there confused. I look aT Jeff, then at Tara, and then at my sister. I let out a nervous little laugh, and then I tell Anne, “What? No, I’ve never fantasized about JEFF, or any other guy, no.” I start walking toward the kitchen shaking my head no, in disbelief.

nervousken | Jun 6, 2025
Jeff hops up and Anne catches your arm "Don't run away, just say 'No'" she whispers to you. Anne strips to her bikini - itnis your favorite one. The bright red, sleek suit that just sets her hips off so well. She smiles and sits in the chair. "It's my turn, SlaveJimmy"

wanker-Jim | Jun 6, 2025
I look at my sister, andit feels soembarrassjng saying how much I she turned me on. But how hot she looks now, anybody can understand why. I kneel down in front of mt sister, and admire her for a second. I start off saying,
“I’m sorry for how I just acted, Anne. I was shocked and I didn’t react well. … Okay, a couple of nights ago, I fantasized about you, Anne. I umm actually fantasized about our parents going out of town, and you caught me spying on you when you when you were drying off from taking a shower. I TRIED TO RUN AWAY, BUT YOU CALLED ME BACK. You let me caress your tits, and then you let me suck them. After a short while, you pushed my head down, and I ended up on my knees. You had me lick your pussy until you cum. Then you took me into your bedroom, and played around. We thenfound ourselvesin the 69 position with you on top, so you were sucking my cock, and I was licking your pussy again.” …I am blushing so hard, and obviously squirming before my sister. Mymouth isdry as I try to continue. I umm I hope thatyou and the other ladies don’t think that I need too much. I hope that you have fun, and that you are proud of me this weekend, Anne. “

nervousken | Jun 6, 2025
Anne leans back, calm and relaxed. "You said you have never given a woman an orgasm... and you want me to receive the very first orgasm you give. Tell me how you want to make me cum"

wanker-Jim | Jun 6, 2025
The embarrassment rushing through, my whole body burns. I knowI am blushing so hard. NEVER have I even imagined that I would be kneeling at my sister’s feet, telling her … and all the most popular and sexiest women I know … how I want to give my SISTER an orgasm. It aked me a moment to recover before I try to explain. “I … Idon’t know, Anne. I’ve imagined a few different ways. I think umm my favorite way would be licking your pussy, umm I think that would be my favorite way for you and for me. Umm, I might need some instruction from you through, I have never done this before. “ … I feel so humiliated right now … my stomach hurts, my mind is melting, I want to run away … yet I remain kneel, at my sister’s feet, squirming in my chastity cage, more turned on that I have ever been in my life … waiting for my adorable little suster to reply.

nervousken | Jun 6, 2025
Sensing the humiliation is crushing you, Anne reaches down and gently cups your chin, lifting your face to look into your eyes. She is about to say something when she pauses and looks around at everyone watching. She abruptly stands up and hold her hand fornyou and helps you up. She sots you in the chair she was just in. Then, to everyone else, she says "SlaveJimmy has done an amazing job and confessed some deeply personal and humiliating things. He deserves a reward. Each of us will kneel in front of him and make a cinfession to him or admit something emvarassing or comment on his admissions to us. He can then ask one question and we can answer it ornlose our bikini top." With that... Anne lowers herself to her knees. Not a few wlfeet away like youbwere, but right between your knees as if she were going to blow you. She puts her hands on yourbthighs and looksnup at you. Then, after another pause... she leans forward and uses the keybon her necklace to unlock and remive your cage. Now, kneeling in her bikini between your legs, she smiles and takes your cock in herbhand... then leans forward to lick the tip once. Eve speaks up "SlaveJimmy, do NOT cum" she commands. Anne giggles and looks up. "My confession, SlaveJimmy, I want you to go down on me and make me cum. Last night, when I masturbated to so manyborgasms, I was thinking about your mouth on my pussy. I was thinking about this cock inside me" she pauses and looks up. "Younmay ask one question"

wanker-Jim | Jun 6, 2025
By JUST TOUCHING my cock Anne has my erection hard and aching, the gentle feel of her tongue has it throbbing, and Eve has ordered me NOT to cum! Howam I suppose to think … or think of any questions for my sister right now? U whimoer, holding back an enomous orgasm, then I ask my sister, “Will you please tell me when, and describe how you lost your virginity, Anne?”

nervousken | Jun 6, 2025
Anne smiles and is about to say something... then she gets a very mischecious smile on her face. She takes the head of your cock into her mouth and sucks gently while teasing the tip with your tongue. You moan loudly and Anne reqchea behind her back to unhook her bikini top. She stands up, topless and smiles. "I'd rather not answer that... so, I lose my top." You groan and everyone cheers at the beautiful topless woman. Anne bows for her fans and then beckons for Amy to take her place. Amy kneels between your legs and nervously holds your cock. "I guess my confession now is that I really hoped my first blowjob would be special, but I am so turned on and this is so tempting that I am having a really hard time not asking you if I can blow you this weekend. Looking down at her, especially after Anne's absolutely devilish tease, it's almost impossible for you to not reach down and pull her to your cock. But, you are a good man and don't want her to do anything ahe may regret later. She looks up nervously. "What wpuld you like to ask me?"

wanker-Jim | Jun 6, 2025
I look at this sweet young woman between my legs, as she holds my desperate erection. I hold my hands behind my back, to resist any temptations. I moan lightly again, as I try to speak. After a deep breath I ask her, “Okay Amy, unn Will you please tell me about YOUR kinkist fantasy?”

nervousken | Jun 6, 2025
Amy turns red and looks around at everyone. "You know, I am just not kinky, I guess. I mean, all of this is a lot kinkier than I could ever think of. Look at me! I am here holding a man's hard cock in front of all of my friends!" Amy starts to stand up and then stops and looks at you, then Chrissy, then Eve and back to you for approval. Not wanting to make her more uncomfortable, you nod and she let's go of your cock and atands up. Christy takes her place and hungrily sucks both of your balls into her mouth, massaging them withbher tongue as she gently teases your cock with the gentlest pressure. From your vantage point, looking down at the kneeling Goddess, she is still an impressive and intimidating woman. She smiles up at you. She thinks for a moment. "I think there js something that nobody knows about me. I'm not some dominant, ball busting bitch. I want to be gentle and soft and kind. But nobody sees that in me. Everyone sees me as a hard dominatrix." She pauses, examining your cock. "Don't get me wrong..." She slowly tightens her grip and it passes from pleasant to tight to painful to wonderful to almost painful and she stops there, holding firm at that perfect pressure that any toghter would be painful and any looser would be miserable... "Don't get me wrong. I do love making men squirm, but that's secondary to giving pleasure." As if to drive the point home, she tickles the head of your throbbing cock with her tongue, and then gently slides her teeth across the stretched and sensitive akin. "OK, dl you have anything to ask me?"

wanker-Jim | Jun 6, 2025
Holy fuck, this woman is amazing, U think, as I lean my head back and moan loudly, in an effort to not cum. “Fuck, Christy, That … I stop speaking in mid “ sentence. I take a moment to regroup myself, before asking her, “Okay, Christy, will you please tell me about the best sex you have ever had? You don’t need to give any names, but I’d like to hear the details.”

-

nervousken | Jun 6, 2025
Christy laughs. "That's all you want to kmow?" Christy lets go og your cock and presser her lips to the tip and kisses it. "About six months ago, I got stuck on a bus back with some guy. He was totally not my type. We started talking and, somehow, I wound up so attracted to him that when we got back to school and I was about to drive home in my car, I offered to give him a ride home and we had the most incredible sex in my car. We haven't told anyone that we are playing and fucking and dating this whole time." Christysmilesup at you. "Does that answer your queation?"

wanker-Jim | Jun 6, 2025
“Well, I guess so, I was just wondering what women like … you know … what they consider their best night of sex.”

nervousken | Jun 6, 2025
Christy smiles and stands up to kiss you. "God, that is so wonderful to hear. Most guys just want to get off... you... you really want to give pleasure don't you?"

wanker-Jim | Jun 6, 2025
“Yes, I hope to. Umm I’m kind of at a disadvantage to some guys, though.” P blush.

nervousken | Jun 6, 2025
Christy leans down and hugs you tight. "The number one thing to giving a woman pleasure is your desire to give it. Big dicks help, but the best dick I've ever had was one of the smaller ones." She sniles and strokes yours gently. "Smaller than yours" With this, she atands up straight. "Do you like my tits, SlaveJimmy?"

wanker-Jim | Jun 6, 2025
“Hell yes I like them, Christy “ I say with a smile.

nervousken | Jun 7, 2025
"Promise to keep being a good slave and I'll keep them out all weekend" With that, Christy slips her bikini top off and stands barechested for you. Jeff seems to be enjoying this a lot. Beth comes up and takes Chrosti's place "I don't know how I can follow THOSE" she says, laughing as she reaches over and gives Christi's tits a squeeze "Jesus, those things are firm" she says in disbelief. Looking back to you, Beth smiles and kneels. She doesn't hold your cock withbher hands or kiss it like the others did. She just looks at it for several seconds and sighs. "OK, I am not sure this is the right time, but you deserve the truth from me. The reason we stopped dating wasn't because you did anything wrong or I did't like you or I didn't want to keep fooling around. Hinestly, it was your obsession with Anne. I seriously thought you two were fooling around. I didn't want to be the third wheel." Beth keeps staring at your cock and then looksnup at you netvously, almost as if she were nearing tears. "So, I know you weten't fooling around withbher and I know I should have said something. I know, yiu are probably mad at me for just stopping our dating without explaining." She tries to smile "I think that you would have gotten to do a lot more than play with my tits...." She chuckles "But seeing what else you have available to you, I see how mybtits are dull" she laughs. Everyone chuckles and Christi shakes her tits for comic effect. "SlaveJim, what woukd you like to ask me?"

wanker-Jim | Jun 7, 2025
I take a breath and exhale slowly, then looking into her eyes, I reply, “Okay Beth, I’m gladthat you explained it. I never knew … you know … what happened between us. I was afraid that you were a size queen, ND THAT YOU HEARD I HAD A SMALL DICK.” I CHUCKLE A LITTLE. “I’M GLAD YOU’RE HERE, AND I HOPE YOU HAVE FUN THIS WEEKEND. … Well,thesequestions areso hard to think up. Okay, J’ll try this one again, Will you please tell me what your kinkiest fantasy is?”

nervousken | Jun 7, 2025
Beth turns red. "I want to sleep with Anne" she confesses

wanker-Jim | Jun 7, 2025
My eyes widen in complete surprise. I look at my sister, and then back at Beth. “WOW, I didn’t expect that! … úmm thank you Beth, for being so honest.” … Damn, I didn’t know what to say. I guess my sister is hot to men and women~ AAfter the shock, I look and smile at my sister.

nervousken | Jun 7, 2025
Beth gets up and Eve takes her place. Before she kneels down, she kisses you and whispers in your ear "I am OK taking my top off if you ask a hard enough quewtion" She kneels between your knees and slowly strokea your cock. "I would say that I really like your fantasy about me" She smiles up at you... "What is your question for me?"

wanker-Jim | Jun 7, 2025
Within a few seconds of stroking my erection, Eve has me on the edge of cumming again. I whimper as I look down at her beautiful face … and cleavage. I choke back a moan, and I ask her, “Okay Eve … umm… Will you please tell me about the kinkiest thing you have done … or night that You have had?” … then I let out a little moan.

nervousken | Jun 7, 2025
"I would have to say it was the time Christi dared me to go without panties while cheering at a football game." She smiles "Is that what you had in mind?"

wanker-Jim | Jun 7, 2025
“ I moan as my cock twitches in her hands, “Oh fuck, Eve, that’s pretty hot. I was probably at that game. I wish I had known you didn’t have panties on, I would have watched you all night instead of the game Next time you do something like that, let me know ahead of time.” I look down at Eve;’s breasts again thrn Iwhimper as I chuckle at my own stupid joke..
“ I moan as my cock twitches in her hands, “Oh fuck, Eve, that’s pretty hot. I was probably at that game. I wish I had known you didn’t have panties on, I would have watched you all night instead of the game Next time you do something like that, let me know ahead of time.” I look down at Eve;’s breasts again thrn Iwhimper as I chuckle at my own stupid joke..

nervousken | Jun 7, 2025
Tara is about to take Eve's place when Jeff stops her. "Jim, I have a confession to make. May I....?" he gestures to the floor Eve was just kneeling on. "I won't touch you likebthe ladies were..." he says nervously. Christi looks at hin "Jeff, are you sure? You don't have to tell anyone" Jeff nods and says "I have to be honest... like everyone one elsebhere is being" Christi hugs him and then Anne chimes in "I am not sure what's going on... but SlaveJimmy, I would likenyou to let him makebhis confession. If youbdon't want hin holding yourncock, you can say so, but Ibthink I speak for all of us ladies when Ibsaybitnwould be super hot if younlet him....."

wanker-Jim | Jun 7, 2025
WhenEve releases my cock Iand steps away,I am nearly trembling from my cock and balls aching so badly to cum. Now Jeff doing this has me totally confused. I look at my sister,then at the other ladies, I notice Amy watching wide-eyed. Tara waits behind Jeff,and she has a big smile and she mouths “Do it, do it,” to me. Now overwhelmed and wanting to please my sister and the other women I stammer,”I … I guess it’s okay.”

nervousken | Jun 7, 2025
Jeff kneels down "Do you remember the guy Christi talked aboit? 'Not her type' and 'the best she's had' and 'smaller than you' and 'secret'? That guy is me. Christi has wanted me to tell you the whole time, bit I have been ashamed to and I wasn't sure how you'd take it." Jeff stops and takes a deep breath. "You see, I opened up to Christi and told her things I've never told anyone and she and I are exploring this. Remember how she used to sxare us because of how intimidating she is? How she coukd humiliate the jock football players that hit on her? She is actually a warm, caring and loving woman." He looks down at the ground. "My secrets that I shared withbher.... You are brave and you take life by the horns. While you are here, comfortable in your own skin, proudly showing your naked body to all these beautiful women. Whilebyou have no shame in sharing your intimate thoights. While you are so secure in yoirself you let people see you in chastity. You admit to your inexperience and virginity. You are a proud and strong man. I am not. I keep my fantasoes hidden in shame." He stamds up and lowers his swim suit. His cock and balls are shaved smooth and he is locked in a chastoty cage. "I am Christi's sex slave. I have been for months." Everyone but Christi is shovked at this. "And there is more. I am bisexual. I have been begging Christi to bring another giy for me to please. And this is a huge fantasy forbher, too. She wants so muchnto watch. But she has insisted that I wait for something and someone special. And she is right." At this point, Christi gets up and comes over to Jeff. She helps him up and hugs him. She soothes him as he sobs from humiliation and shame. You see the tenderness in Chrosti for the first tine.

wanker-Jim | Jun 7, 2025
I am surprised about Christi andJeff, and I am happy for them too. I am Proud of Jeff ffor being so brave, too. After the emotions calm down some, I join t h em m kpnd of a group hug, though I keep my hips back, keeping my erection out, away from touching them. I have learned a lot abpit Christi today and I really like her,and shesure seems good gor Jeff. This has been a very interesting and insightful weekend … so far.

nervousken | Jun 7, 2025
Jeff smiles. "There is one more thing." He sits you back down and lowers his trunks. He, too, is in chastity. "Christi has the key and the only time I am.unlocked is when we have sex or she is giving me a blow job... I haven't masturbated in months, I don't look at porn anymore...." Jeff kneels between your legs "I'm not going to lie... I really want to stroke your cock, Jim... but I won't unless you want me to... or one of the ladies tells me to." He looks around hopefully and everyone geta a chuckle from his obvious request. "Do you have anything you want to ask?"

wanker-Jim | Jun 7, 2025
I sit there frozen for a moment,I don’t know what to say. Should I be offended that he thinks of me in gay ways … or flattered because he fantasizes about ME?? I ook up at Christi for a second, then back at Jeff.Trying to be sensitiveof him being sovonerable, I tell him, “”Umm I’m sorry, but no, Jeff. I don’t want you to stroke my cock. No offense but umm I ham m really attracted to women. “ Still comfused bt his offer I ask, :Why umm With all the huys out there, why would you fantasize about ME?”

nervousken | Jun 7, 2025
"It's not that I think you are gay or want to be with me. It's just like famtasizing about a beautiful woman who doesn't want to sleep with you. i hope you aren't offended." Jeff smiled. "I'm not attracted to men... but Injust want to experience cock. And you are a good guy to start with. We know each other well, I trust you... and we are both slaves for the weekend."

wanker-Jim | Jun 7, 2025
Jeff’s explanation seems sincere enough …and we are both slaves this weekend. Shit, I still don’ t know what ro do. Searching for help, or a signal. I look at my sister … then to Eve … then I look at Christy and our eyes meet for a couple seconds. When Christi breaks eye contact and she looks down, a I feel a wave of disappointment from her. … I take a deep breath, then I say, “Okay, you can stroke my cock, but you HAVE to stop when I say stop.”

nervousken | Jun 7, 2025
Jeff looks up in surprise and then looks at Christi. She pulls a chair over and sits next to him and all of the ladies gather around closely. Anne whispers in your ear "Thank you. All of us have some kind of fantasy involvomg two guys..." Jeff, suddenly self conscious, slowly reaches for your cock and gently wraps his hand around the shaft. Seeing you react with pleasure, he relaxes and begins to slowly, gently stroke. Christi whispers something to Eve who returns quickly with some lotion and Jeff takes a moment to lotion his hand. Your head leans back and you groan in pleasure at the magical feeling of another person's hands stroking your cock... and massaging your balls. Eve leans down and kisses you, only making the experience more confusing and erotic for you. "Are you enjpying this?" Tara asks, her eyes are glued to Jeff's hands on your cock and her face is flushed.

wanker-Jim | Jun 7, 2025
I can’t help but moan a little when I answer her ,”Ohhh Yes. It feels good, Tara. But we need to stop soon.” Even though he has proven to be a good cock stroker, Eve said that I must not cum, earlier. I do NOT want a goy to makeme cum, anyway.

nervousken | Jun 7, 2025
Anne teases. "Yeah, your next orgasm belongs to me" Jeff lets go, but not before leaning forward to kiss the tip gently. He stands up and Tara takes his place. She leans in and licks your cock and balls. Looking up at youz she holds your cock. "That might have been the hottest thingnI have seen in my life" she laughs as the ladies all agree. She takes a deep breath. "OK, my confession is probably that I was really grossed oit by you perving on your sister. But after talking with Anne and everyone, I've come around. I get it, Anne is super sexy, she lives down the hall, she teases you mercilessly. How coild you NOT have the hots for her?" She strokes you a few times "Does that make sense?"

wanker-Jim | Jun 7, 2025
I whimper as Tara keeps me right on the edge of a fierce orasm. “Yes, I mean… I mean , she’s, she’s irrestible sometimes. And, and YOU hanging around withm just makes it even hotter. … I… Anne teased meon purpose?” I look at my sister and smile. … then I moan loudly, “Oh fucgagE cum now?”

nervousken | Jun 7, 2025
Tara stops stroking and Anne smiles "You can cum after I do later.... Do youbhave a question for Tara?"

wanker-Jim | Jun 7, 2025
I look at my sister then I look at her hot little tits. I moan a little in frustration, and I almost start to argue with he r, but then I stop myself, “But Anne … Yes, Anne, I’ll wait.” I feel a little defeated, nut turning my attention to Tara cheers me up. “Okay Tara, I told you, and everyone her my fantasy about you. Willyou please tell me your favorite fantasy about me, or what you want to do to me?”

nervousken | Jun 7, 2025
"I really don't want to share my deepest fantasy with you right now because I am afraid you will freak out and feel bad. But... for right now, my greatest hope for this weekend is that you learn to be comfortable making all of us orgasm." Tara slips her bikini top off and smiles "Hey, I didn't answer your question!" Anne stands up and takes control. "OK, we need a change of scenery here. SlaveJimmy, lock your cock back up in the cage and then join Jeff in the kitchen. Make some iced tea, lemonade, whatever, and bring it out to the pool. We have some fun games to play and lighten the mood, this confession part seemed to get super heavy." You look around and realize that the two women you are most attracted to in the world are wearing nothing but bikini bottoms! And Christi, the SexGoddess with her amazing tits is, too! And there are three other beautiful women also playing these games in bikinis. You smile at Jeff, not feeling any of the strangeness you thought you'd feel. In the kitchen, he is filling glasses with ice, completely naked except for his chastity cage. "This is crazy, huh? I wonder if we can have sex with all of the women" he says as you walk in.

wanker-Jim | Jun 7, 2025
“Yeah, they are all VERY sexy and wild.” I say as I smile at Jeff. Hey. congratulation on getting together with Christi, I’’m really getting to like her. Don’t worry, I won’t try to stral your girlfriend from you.” Ilaugh. “Damn ,. m so horny that all the ladies look aexier than they ever have, if that’s possible.” I laugh again. “Anne says I won’t be allowed to cum until later, though.” … don’t try to talk about what Jeff and I did, but Ihope it doesn’t effect friendxhip.Then as I pick up a tray of drinks, I ask Jeff, “SinceCgristi kept your relationship quiet, I guess you didn’t go through a slave party?”

nervousken | Jun 7, 2025
"Not really.... it's hard to explain. Somehow, we wpund up talking about it and she mentioned how everyone misunderatood her.... I admitted that my impression of her was...you know. The whole slave thing came up organically and we were both super nervous about it. Ot was actually Eve that helped us set upnour arrqngement. We had two 'slave weekends ' witj five days' of just a few hours contact per day. Rhen we had five days of no contact at all while Eve asked us all kinds of questions. The following Friday is when we sat down, talked and began what we are doing now. Crazy, huh? ME... with Christi! Who would have imagined that? And, yeah, I've also been with Eve. It's scary as hell. Bit also really rewarding. Not just thw sex either! The emotional connection. Chrosti has made me orgasm without cumming just from talking and making out. That is probably the greateatbthing ever!" He stops. "So, enough about me! So you and Tara! That is perfect!"

wanker-Jim | Jun 8, 2025
Well Anne, umm I’m actually my sister’s slave, but Tara helps her. Those two are together so much, I’m basically a slave to both ofthem. Anne [ut me in the chastity cage and took charge of me, and Tara has too since then. Anne keeps the key to my cock cage, so she really has the power. My sister even had the key to my chastity cage on her necklace, when we had breakfast with our parents.” U laugh. I am only suppose to be my sister’s slave for this weekend,though.”

wanker-Jim | Jun 8, 2025
… I add, “Does Christi make you wear her panties and bra and stuff?”

nervousken | Jun 8, 2025
"Oh, I'm sorry. I assumed you were Tara's slave. Christi told me Tara has had a crush on you for a while." Jeff pauses and then continues "Actually, Tara, Beth and Eve have all had crushes on you." Then he chuxkles "Women's underwear. Tell the truth. Wearing Anne or Tara's panties really makes you feel sexy as hell, right? I kmow I am supposed to be embarassed, but I love wearing Christi's panties. They are so soft and they hold my balls so well, but also so soft." He finishes filling the pitcher with iced tea "I don't like wearing bras. They are uncomfortable but she uses it as a punishment"

wanker-Jim | Jun 8, 2025
it’s for punishment? LAnne knows that I have been using her panties and bras and masturbating in them Last night, she even told me what color and bra that I had in my room. She had me wear them jnder my clothes at ginner, with our parents there. Tara AND Eve have a crush on me?” I smile and almost start squirming. “And Bethbroke up with me, and she said she wanted to sleep with Anne, today. Why umm why do somany people have crushes and fantasize about ME?” I laugh. “Umm I guess I should be flattered. … Fuck,ve has had me so turned in for her today. They all seem to like that I’m in a chastity cage as Anne’s slave. … Hey Jeff,do you know anything about Amy? I don’t remember seeing her with Anne before.” I helpJeff get everything ready to take out to the pool. :Fuck, Im nervous now, since those girls like me. Well Ihavenothing tohide fromthem,today.” I laugh.”

nervousken | Jun 8, 2025
"Amy? Jeez, all I know about her is she just follows Christi and Eve around. Christi asked if I wanted Amy to come play, but honestly Christi and Eve are way too much already." He starts getting ready to go out to yhe pool. "You are Anne's only forbthe weekend? Whatbhappens after?"

wanker-Jim | Jun 8, 2025
“What happensafter this weekend?Umm we’re done playing, I guess. We didn’t really talk about it, but our parents will be back Monday afternoon. Anne umm caught me in a compromising situation,and she saidI was her slave this weekend, or she would show people the video. … Tara did say that they’ve been planning this for weeks, though?? What do you think is going to happen SundayNight?”

nervousken | Jun 8, 2025
"Dude, I have no idea what they're planning. My advice? If you trust them, just relax and go with it. If you don't trust them, end the game here and now." And withbthat Jeff walks out naked and caged into the backyard. You watch, almost in awe of his comfort and confidence before following

wanker-Jim | Jun 8, 2025
I get up my courage and walk into the back yard. As I look at thuer tits, I notice both Anne and Tara lookingto make sure I have my cockcage on. After each woman has rgier drinks, I take a drinkfor myself and I sit down. I admire these sexy youngladies, beautifulyoung women, as I unwind from the stress from this morning. … My ballsstill achedeom being si aroused for solong, without being allowed to cum. … Isee Anne get up, and my eyes are locked on her beautiful little tits, as I see her walkingover to me.

nervousken | Jun 8, 2025
Anne sits on the lounge next to you, placing her hand on your thigh. "Hey, Jim, I just wanted to check in and see how you are doing. That was a lot of information this morning and it's a lot to process." She waited a bit and then continued "Is there anything you need to talk about?" Her use of 'JIM' isn't lost on you... you take it as a sign that this conversation isn't Mistress and slave.

wanker-Jim | Jun 8, 2025
“Yah, ir was a ljffle rough at times, but now that we/re through it, it/s good. I tell her and then smile. ?I really appreciate … and adure you for stabding up for me when things got the roughest, and I really appreciate that, Anne … And there have been some really fun and exciting times too. .” I break eye contact and look down at my chastity cage. :ooling vack up I look at my sister’s tits, and then up to her eyes. ?J/ve never been so horny … or been kept so horny in my life, Anne.” I chuckle and blush a little, “OR been so embarrassed. …Umm Anne umm you wereplanning tokeepme locked in this cagelonger than this morning or until after lunch, aren’t you? Tara saud that you two have been planning this for weeks.? Before Anneanswers, I add, “All the ladies a[ready know that you have my cock locked up, but howlong are You planning on keeping me locked?” I squirm a little.”I … I know that I am your slave … and all your fRiends slave all weekend, but I don’t know if I can stand it THAT lomg.” Again I xhuckle and blush, “YOU and all of your friends are so fuckingHOT. “

nervousken | Jun 8, 2025
"Jim, here are my plans for the evening. I had planned on keeping it a surprise, but I can see you are really stressed out by the cage. Tonight, you and I will sleep in the same bed, just the two of us. Nobody else joining or watching or anything. Just us. And we will both lose our viginities tonight. Together." You are stunned. "Honestly, I was going to have you lose your virginity with Tara, but after how incredible you were with that confession game, I have to have you." She moves her hand and caresses your caged cock. "Now, I fully intend on you making me cum this afternoon. And you will use your mouth. And I will let everyone who wants experience the same... but I will be the first pussy youbtaste, the first orgasm you taste, the first pussy yiu slide into, the first pussy you fill with cum.... and, if you are a good boy, the first ass your cock slides into." As for how long you wear the cage... Can we talk about the cage's future Sunday evening? I don't have any plans for any of this past when we change from SlaveJimmy to SlaveAnne"

wanker-Jim | Jun 9, 2025
I am shocked and am,ost breathless after hearing this from my sister, “Holy shit, Anne … are you serious? I mean, That sounds perfect, I mean really, really perfect. Damn, Anne,, I have dreame …, and masturbated … about having sex with you for so long, And YOU are still a virgin, too? Wow. “ I am squirming hard as I stare at my sister … I can’t take my eyes off my sister. “And umm, the other ladies? Do they know? I mean, I thought they were going to spend the night tonight and be here all weekend. … Holy shit, Anne, I can’t wait for tonight now. Oh fuck, I love you do much, Anne.” I am almost bursting from anticipation as I sytare at my beautiful sister, imagining what tonight will be like.

nervousken | Jun 9, 2025
"I am dead serious. Look, I know we can't have a real sexual relationship, so I want to have my fun with you before we accept reality and you begin dating someone like Eve or Beth or Tara or Christi, though I think Christi and Jeff are a thing" she laughs at that "Seriously, those two? Nothing against Jeff, but I just don't get those two" She takes a breath. "Can I be honest? I know you reallyblike Tara but that's just because you see her more because she is my best friend. I really think you and Eve will be better together." With that, she atands up. "OK, we are going to play Chicken! We'll pair up into four teams, The first team to fall will have to reward the last team standing, then we'll change teams. Jeff, SlaveJim, you pick your partners and the remaining four ladies will pair themselves." You look at Jeff and gesture to him tompick first. He picks Christi, of course and then all eyes are on you to pick your partner"

wanker-Jim | Jun 9, 2025
Since she seems pretty athletic, and a lot of fun, “I”ll pick Eve.” I say.

nervousken | Jun 9, 2025
Anne and Amy agree that Beth will be with Amy and Tara with Anne. You, Jeff, Tara and Amy hop in the pool and yournpartners climb on your shoulders before spreading out. All of a sudden, you realize that you are living out a fantasy... to have topless women playing chicken in the pool! You are staring at Christi and Anne's bare breasts. Tara and Jeff see your distraction, but it's Amy that slips in and Beth quickly topples Eve. You both sit on the edge of the pool and watch the game. Beth is knocked off when she tries to handle Christi. Now, it's three topless women and a naked Jeff. Anne doesn't stand a chamce against Christi. "Eve, SlaveJimmy... your punishment is to.... kiss the feet of your betters" Christi says. Her and Jeff hop out of the pool and stand at the edge near the others. You and Eve swim to the edge and begin kissing their feet... forst you kiss Christi's and Eve Jeff's... but after a littlw bit, Anne tells you to switch and you are kissing your best friend's feet while that beautiful woman kisses Christi's. "OK, next round!" Anne pairs herself with you, Christi pairs herself with Beth. Eve pairs up with Jeff and Tara with Amy. With your topless sister on your shoukders, you are keenly aware of her barely covered pussy rubbing on your neck. You move to Jeff and Anne tries to kmock over Eve while Beth tries to knock Tara over. Tara goes down first, then Eve leaving you facing Christi... Anne facing Beth. You quickly realize that Chrisi is serious. She topples you, bringing Anne down with you. Beth and Christi smile at Tara and Amy. Christi and Beth talk quietly, then announce that the punishment is for Tara and Amy to sit at the edge of the pool, pull their suits asode and masturbate in full view for two minutes. Amy is beet red as she complies, but Tara takes it in stride. The next round has you and Christi winning and Anne and Eve losing. Christi smiles at you and whispers innyour ear "What do you wqnt their punishment to be?"

wanker-Jim | Jun 9, 2025
with this one. I wouldn’y mind ME rewarding them both … I finally decide “Okay, you BOTH take off your swimsuit, then swim a full lap skinny dipping.’ … Then I bevome very aware that this is the first naked pussy I have seen… and oneofthem is my sister’s pussy, and the other is my new crush’s pussy.

with this one. I wouldn’y mind ME rewarding them both … I finally decide “Okay, you BOTH take off your swimsuit, then swim a full lap skinny dipping.’ … Then I bevome very aware that this is the first naked pussy I have seen… and oneofthem is my sister’s pussy, and the other is my new crush’s pussy.

nervousken | Jun 9, 2025
Christi laughs "I like the naked people" she says, pointedly looking at Anne. For the next round, Jeff and Amy lose and Beth and Eve win. The punishment is that Eve and Beth get to spank Jeff and Amy. A few more rounds are played and the punishments for losing is usually fun and silly. Finally, Anne announces "OK. We have time for two more rounds. Next round, the losers will french kiss EVERYONE'S assholes" She smiles at Tara, who laughs. "And the last round losers have to answer the door when the pizza gets here... naked!" You are paired up with Jeff. At first you feel strange getting on his shpulders, but then you realize that there is no way you'll have to kiss Jeff's asshole. However, it's Beth and Eve that lose. At first, it's crazy hot watching those beautiful women work their way through every one, you get super nervous when Eve smiles "Your turn" You bend over the edge of the pool and Eve playfully bites your butt cheeks before spreading them and moving in her hot tongue caressing and probing...

wanker-Jim | Jun 9, 2025
fAs I feel eel Eve’s tongue, I gasp and a moan slips out … this wom sis INCREDABLE .Each time Ifeel her tongue touch my butt hole, I feel my insides jump. My cock swells and I feelthe pressure against my chastity cage. It seems like Eve is licking my ass longer than the others, but I’m not complaining . IEve is so sexy, in every sense of the word. I let out another, gentler mosn … then all of the sudden, I am thinking to mysellf … Please don’t cum … Please don’t cum.

nervousken | Jun 9, 2025
As Eve pulls away, she spanks your butt firmly withbher hand and you motice EVERYONE is staring at you. "Did you enjoy that, SlaveJimmy?" Tara asks with a knowing smile. Amy soon moves in and gives three quick but unexciting licks. You admit to yourself that it felt very good, but it was nothing compared to Eve.

nervousken | Jun 9, 2025
Anne smiles "OK, SlaveJimmy, you pick all of the teams for the last game.... and who you would like to see lose and answer the door naked"

wanker-Jim | Jun 9, 2025
I resist answering Tara’s question, but I look at her as I blush hard, then I look at Eve in the corner of my eye and I can’t hide a little smile. Umm, lets go with Amy and Tara, Jeff and Anne, Christi and Beth, and then Eve and me. I think those are pretty fair teams. So who would I like toseeanswer the door? Probably Christi and TBeth.”

nervousken | Jun 9, 2025
Anne smiles "That sounds great! Now, for a little change.... this will be a backwards round. The top person will be sitting faving BACKWARDS. Eve quickly swims to you and smiles as she pushes you under and climbs on your shoulders, her pussy right atbyour face! As you stand up, you realize she had slipped her bottoms off and you were face to fave wothbher pussy!!! Youbtried, but couldn't get your mouth to kiss her because of the angle, but the temptation was incredible. Not even caring about the game, you walk to the edge of the pool and gently set Eve on the edge, then lower down to kiss her pussy. After a few seconds, Anne pulls you away. "Not yet, you little pervert" she teases. "Remember, I cum on that tongue before anybody else." At this point, you realize everyone is around you watching. Anne gets out of the pool and begins to dry her nakes body off with a towel. You soon rwalize that the only people wearing clothing are Christy and Beth with their bikini bottoms and Amy in both her top and bottom, and you and Jeff are mesmerized by the sight of these beautiful women drying themselves off. Anne asks you and Jeff to get out of the pool and dry eachother off while the ladies watch. They all recline back on their lounge chairs, barely covered bybtheir own towels and watxh as the two naked men climb out of the pool.

wanker-Jim | Jun 9, 2025
I’m still a little shook up and VERY horny after myclose encounter with Eve’s amazing shaved little puss7.l I start to get out of the pool. “Dry each other off?” I ask in disbelief. Anne smiles and nods a dwfinitive YES. Bbefore I can say or do anything Jeff is standing right in front of me with two towesl. He starts drying my back and sgoulders, then my chest. Nest, he gets down on his knees and reaches around to dry my burrocks, his face inches frpm my chastity cage. he even dries down my ass crack. Jeff takes his time drying mychastity cage, and even more time drying my aching balls. He dries down my legs while he looks up at me. … And then …he dries my balls again. Then Jeff hands me a dry towel, to dry him off. Reluctantly I take the towel. Then I ask Anne, or anybody that will answer me, “Who won, … and more importantly … who LOST that last games anyway?”

nervousken | Jun 9, 2025
"I had no idea watching two men dry eachnother off woukd be so fucking sexy" Tara says as the ladies watch you intently

wanker-Jim | Jun 9, 2025
Hearing Tara’s c0mments, I figure that I w9n]t get an aI Won]t getan answer about the game, until I finish drying off Jeff. I start on his Bck, like he did mine. Luckly I have plenty to distract me as I rub his body with the towel. I must have looked at Eve, and at Anne, and the other girls MUCH more than I looked at Jeff. I became very aware of what I was doing when I drued him just below his waist. I rubbed Heff’s balls, and between his legs, blushing, but I kept glancing up at the women. After I finished drying his legs and feet, I rubbed Jeff’s ballsonce more, for the ladies entertainment. … WhenI got done, Iasked again, , There, are you happy? … Now will somebody please tellme who won and who LOST the last game? I Umm I was destracted.” I look into Eve’s beautiful eyes as I blush.

nervousken | Jun 9, 2025
"SlaveJim, don't get an attitude. Come bend over my lap for a spanking" Anne says.

wanker-Jim | Jun 9, 2025
Anne’s orders and the tone of her voice stun me. and I feel myself blushing hard. Then I remember that Anne had said that she wanted to spank me, because she had never spanked a man. Even though I knw ew she wanted to do this, it was still highly embarrassing. Being … basically naked, and being spanked this way, in front of all these beautiful women. As I walk toreceive my punishment from my sister, I notice that Eve’s and Any’s interests are particularly peaked.

nervousken | Jun 9, 2025
Irritated that you had become too comfortable resisting being her slave, Anne chose to really drive the power dynamic home. Anne remained naked, but kept the towel draped across her lap as you laid naked across her lap. She positioned your legs so they were apread wide and your balls were fully exposed and on display. She begins spanking your bare bottom withbher bare hand, making aure thatbit doean't get too painful. She takea frequent breaks to pause and massage your balls. At one point, she takes a break, keeping you across her lap, she takes several minutes to playnwoth your butt crack, sliding her fingers up and down, teasing you. Christi hands her some lube and Anne begins to work her fingers in ans out of your asshole between spankings. She contonues massaging your balls, teasing and probing your ass and spanking yoi until you begin to moan for her. You are ashamed of yoir reaction, but you kmow it's natural and that the women want to see this. Finally, after a long while, Anne asks "OK, SlaveJimmy. What have you learned?" before you can answer, she teasingly works two fingers intonyour ass, eliciting a moan. She keepa those fingers teasing you while you try to put your answer into words

wanker-Jim | Jun 9, 2025
“I’m sorry, Anne. I’m sorry I tool advantage ofyou kindness, and that I didn’t give you my full attention, or give you full control As YOUR slave, and the slave of all these ladies, it is you happiness that matters. It is my duty as your slave to help bring that happiness to you … you ladieS.” Iamvery aware of my sister’s fingers inside of me, and how powerless I am to her. “ “ I’ve been selfish, and I’ve neglected to share my honest love with you … and all of you ladies.”

nervousken | Jun 9, 2025
"Have we been cruel or mean to you? Have we done anything extreme or excessive to you?"

wanker-Jim | Jun 9, 2025
J look ineo Anne’s eyes as she asks her question to me, “ Umm No, nyou All have been so been great. You’ve brought some of my feeling to the surface, and taught me sothing that I can complain about myself. But really nothing excessive … that I can complain about.” Then I lookwet6ile.

nervousken | Jun 9, 2025
"In fact.... we have made some of your fantasoes come true and we've done thjngs that you enjoyed.... so why are you being impatient with us?" Anne slowly works a third finger into you while her other hand massages your balls... not painfully, but more firmly than before - as if to remind you that she COULD cause you great pain if she chose.

wanker-Jim | Jun 9, 2025
me … sexually and emotionally. I’ve never been so humiliated on my life. My mind spins. “Ohhh Anne,” I moan as I almost collapse on her lap. “Anne, you are the perfect sister, and I want to be YOUR slave.””

nervousken | Jun 9, 2025
"So why are you so disreapectful and impatient?" Anne briefly tugs your balls to make a point.

wanker-Jim | Jun 9, 2025
Anne,I don’t mean to be disrespectful, really I don’t. I adore you Anne, I’ve … I’ve been in love with you … with you and Tara. I haven’t had sex wuth you, so I’ve hust been masturbating for .. for years. Anne, you, you and Tara are the only girls I’ve ever wanted. I want to make you happy … I want you to be happy with me.”… I thought this might be my only chance.”

nervousken | Jun 9, 2025
"SlaveJimmy, I want you to trust me and not be so hung up on your next pleasure. Focus on entertaining us and what we want to see and I promose yoh will get far more pleasure than you can imagine" Anne spanks you a few more times for fun "Remember how scared you were to be in my underwear last night? It turned into a really great night, didn't it? The more you please us, the more we please you."

wanker-Jim | Jun 9, 2025
I look imto my sister’s eyes, “Yes Anne, I beleuve you, and I want to please you.” I look at Tara, then at my sister, “Thank you Tara, it was an amazing night.And thank you Anne, for arranging it. … I know that I have a lot to learn to please you ladies, I promise that I will try my best.” I look over to the lasies, ashamed of myself … then I can’t take my eyes off Eve.

nervousken | Jun 10, 2025
Anne lets you stand up and then she says "I think we've been too nice to our slaves. For the next two hours, neither of you is allowed to speak unless you are asked a direct question and told to answer." Anne smiles and looks at Eve. Eve takes control "OK, boys. This is going to be a lot of fun. First, please go get us more lemonade while we all put our suits back on, then we'll get started. I think we'll play "Mistress Says""

wanker-Jim | Jun 10, 2025
I goto the kitchen to get the drinks. I want to ask Jeff what the fell I did wro=ong, but … we aren’t suppose to speak. The playing games was fun, but the ladies now takingcommand of things is also kind of interestjng. I wonder what is going to happen next. I wonder if Jeff has an idea of what we will have to do. … Ijust gon’t underdtand this slave stuff, or what I am suppose to do. … I also wonder if Eve really likes nem or if her flirting id just a oart if this game

nervousken | Jun 10, 2025
As you are about to walk out with the lomonade, Eve walks through, she has her bikini on and a colorful wrap to dress her swimsuit up a little. She stops and sends Jeff out "I know this is a lot to process. What you did wrong was act selfish and childish by demanding to know who won or lost. You were also hesotant to dry off Jeff. Look, we know you aren't gay. None of us are, not even Jeff. Look at it like this. Would you want to watch me make out withbTara? Would ot be exciting to wqtch Tara eat Anne's pussy? Of course you would. Christi and I have played together a lot while Jeff enjoyed the show. You will enjoy watching women play if it comes up. We expect the same respect. Now, I believe you have a decision to make. I know that the first woman you make cum will be Anne and this will be tonight. She has also asked that you both be each other's first. I want to spend tonight in bed with you. You need to decide who you sleep with tonight. Me or your sister." Youbstart to amswer, but stop yourself. "Good boy" Eve smiles, gently caressing your balls as a reward. "Don't answer... but I will let you ask me one question. You may speak and ask it"

wanker-Jim | Jun 10, 2025
I take a monebt trying to understand what

Eve just said. I raise ny eyes to look into Eve’s., and I feel my eyesfill with teaRs when I ask, “Anee … Anne didn’t umm abstain from sex because of ME, did she?”

nervousken | Jun 10, 2025
Eve laughs. "How on earth would I know that?" She smiles at you "OK, back to the game" and she walks put of the kitchen

wanker-Jim | Jun 10, 2025
My question wasn’t a joke. I know that it wasn’t a fair question to ask Eve,especially if Anne and her aren’t that close. Since Annehasentrustedthe ladies to know that she wasgoing to sleep with her brother she may have talked about it. … My mood hasdefinitely changed since getting out of the pool. I get the drinks,and head out to the back yard. In my mind, I keep debating what to do. Eve seems like a wonderful, fun woman. But I would never ever gurt Anne, not this way. … But, Annedid say Eve wou

nervousken | Jun 10, 2025
"OK, here is how the game will go. SlaveJimmy and SlaveJeff will stand up in front of us and for each round, only one lady will give the orders. If she says 'Mistress says' before an order, you have to do it immediately. If she doesn't, you din't do it. The first one to mess up loses the round and that round's Mistress picks the punishment. As for who gets to be Mistress, let's just go in an order and keepngoing until thw pizza gets here. When the call comes tellingnus the pizza is 5 minutes away, the current Mistreas and the previois Mistress will get the pizza, but they can only wear two articles of clothing combined" Anne made aure everyone understood and then asked the boys "Donyou have any questions about the game? Please ask if you do. Also, SlaveJimmy, you can pick the order"

wanker-Jim | Jun 10, 2025
I think I understabd the rules, and I know that I should NOT ask about the punisfments. I look at Heff, and he doesn’t ask anything either, So,” To make it simple, I think we should start on the left, qith Beth, and then Tara, and then go around in order like that, please.” Ater saying that, I HOPE that that wasn’t the first “Mistress says” order, from Anne.

nervousken | Jun 10, 2025
The game progresses and while it makes both you and Jeff very self conscious aboit being so on diaplay, it's fun and the ladies seem to enjoy the goofiness. The punishments start really mild but they begin to get more intense. The punishments are all quick, taking only a few seconds each and you are getting more into the spirit of serving and making the women happy. Finally, we get to Tara and you lose her round. "SlaveJimmy, get on your hands and kmees and kiss each of Jeff's feet five times - withntongue." You are not thenonly one stunned at this and the ladoea all pause to see what yoi'll do"

wanker-Jim | Jun 10, 2025
Shocked by Tara’s punishment ,my stomach chuensm and my heart begins racing in fear. I look at Tara for a second, and then glance around at the other ladies, hoping someone will save he. Alreay blushing, I kneely down, sideways to the ladies,sothey don’t needto look at my asshole. Knowing that Tara wouldn’t let me half-ass it, I kiss Jeff’s feet, my tongue visible for the ladies to see. Still, fully humiliated and blushing, Ikiss them eachfive times, without looking up at the ladues until I finished.

nervousken | Jun 10, 2025
The game continues and Jeff has to kiss your feet to. He spank each other. Finally, while Anne is Mistress, she pauses to annpunce "OK, the last round. Chrosti and I will greet the pizza guy... For the last punishment, we're going to make itnone we've wanted to see but were afraid to ask. And to make it more fun, you have to mess up three times in a row to lose." The competiton betqeen yiu and Jeff is intense and it took a while, but Jeff finally won. Anne smiled and pronounced him the winner. His reward was that every person there would kiss his balls. He seemed really excited and the ladies linednup. "SlaveJimmy, why aren't you in line?" Eve asks. "Why don't you get between me and Amy" Youbsolently get in line, clearly unhappy. Eve leans in "Remember what I told you... And I wanted you after Amy because I think she'll be really timid and not do a great job so you're kisses will look better." Each woman gives each ofbhis balls a kiss and then kisses him on the cheeks. Then, it's Amy's turn and she was so shy it was almost embarassingbhow quick and boring her kisses were... Eve squeezes yourbhand before gently puahingnyou to Jeff

wanker-Jim | Jun 11, 2025
I am so scared and embarrassed, WHY do these women make me do this? I do appreciate Eve’s suppor t though. I don’t even look at Jeff as I aporoach him. I look at his balls, then I look at Eve again. Not sure if I can do this, I force myself to lean my head forward and I kiss one ball and then the other. After the kisses, I quickly step away. I want to spit, but I know that would judt bring me more trouble. I am so humiliated, my head is spinning,as I stand there waiting for Eve.

nervousken | Jun 11, 2025
Anne comes up and grabs you, pullimg you to her room. She tears be bikini bottoms off as she lays on the bed and she pulls your head into her pussy. "That was so fucking sexy" she aays "Eat my pussy NOW, younslave!"

wanker-Jim | Jun 11, 2025
I get so excited with my sister’s hot, beautiful pussy right in front of my face. I immediately start licking her pussy, tjen quickly, I penetrate her with my tongue, ifeel her warm sweet pussy envelope my tonguee. I a m squirming and whimpering as want so badly to make her cum. This seems to happen so gast, though I’ve been fantasizing for this so long. I am so excited zi’mon the edge of losing control. As I lick adn d ongue her pussy, I hope I am d oing this right. Oh fuck,I want Anne’s pussy so mucm I could lick her for hours. I grab Anne’s hips and drive my tongue deep, deeper into her. I look up at my amazing sister as I tongue fuck her … hoping that she will teach me what pleasures her the most.

nervousken | Jun 11, 2025
Anne comes loudly and pushes you away. "You did very well for your first time, SlaveJimmy." Rather than another bikininto replace the bottoms she tore off in the heat of the moment, she asks you to pick out a bra and panties for her. After handing them to her, she dorects you back to the living room where you see Jeff has his face between Amy's thighs. Eve pulls you over and kisses you. She smiles and teases "Your sister is deliciois, but I am better" She leans back and guides you to her pussy. "See what happens when you don't complain?"

wanker-Jim | Jun 11, 2025
“Holy shit,” I thin k as I look at Eves pussy, and then I look and U e come lost in her captivating eyes. Almost instinctively start licking, a nd I feel her oussy responding to my tongue. I squim as Eve looks down at me and smiles, she gently holdsmy head between her thighs. I moan as I lick inside Eve’s pussy, aching to bring this incredible woman to orgasm. I am so excited and so infatuated wuth Eve, I don’t kno w if I even blink as I look up into her eyes.

nervousken | Jun 11, 2025
Eve comes quickly and then pulls you up to lay with her. She holds your head to her chest and gently strokes your hair. "SlaveJimmy, we all kmow you didnt want tonkiss his balls, and we love that you did itnto please us. I want you to know that tonight you will be going further. You need to kmow that you won't be acting out of being gay, but you will be actong as a slave who follows orders. I kmow what your limits are and I swear they will be reapected. Will youboney tonight?"

wanker-Jim | Jun 11, 2025
I kiss Eve’s I kiss Eve’s chest as she ositionb s m y head on her. I am still extreme;y excited, yet Eve also makes me very comfortable with her. As Eve is duscussin g thuer plans, I suddenly becomeVERYy unc omfortable. I want to get up and get the hell out of here, but for some reason I don’t. U want to prove my devotion to Anne and Eve as their slave, andas a slave to all the ladies here.. … ILOOKING UPINTO HER EYES, *

WANT TO PROVE MY DEVOTIONTO Anne and to Eve, as their slave, and as a slave to all of these ladies. . Looking up into Eve’s eyes, I stumble over my words,
… ‘I’ll try Eve … Umm I “want to try my best for you an d Anne, Eve.,

nervousken | Jun 11, 2025
"Don't do it for us or the promise of what may come later. Obey because you wqbt to be the best slaveboy you can be" Eve smiles down at you and then looks over at the rest of the ladies.

wanker-Jim | Jun 11, 2025
“I will Eve, “ I tel lher. Then I folow where Eve is looking to the ladies, and I give them a soft smile.

nervousken | Jun 11, 2025
Christi and Anne get everyone's attention. "OK, the pizza is almost here! Who wants to pick what we wear?' Wveryine unanimously agrees SlaveJimmy shoukd pick. Christi reminds you "Remember that the twonof us can only wear twonitems of clothing combined" and Anne follows up "Yes, and you wouldn't wqnt your dear, loving aister diaplayed obscenely to thw world" Everyone chuckles at that, but the ladies seem a littlw nervous about possibly bwing naked for strangers

wanker-Jim | Jun 11, 2025
“They can wear ANY pieces of clothing?” I ask, as I think. … “Okay ,Christi, you wear your bikini bottoms, so you can show off your big tit. And Anne, you go and get your short little red robe, but you have to leave it open in front.” I blush a little as I tell them what to wear.

nervousken | Jun 11, 2025
When Anne returns, she is clearly uncomfortable with how exposed she will be. Eve takes control. OK, SlaveJimmy, SlaveJeff, here are your leashes. The ladies will hold one end and the other end will be clipped to your chastity cages." You are stunned at this, but you know not to argue. "Anne, Christi, sit on the loveseat facing the door and make out with each other until the second time the doorbell rings. Then you both get up to answer. Slaves, hands and knees only, you'll be crawling" Anne and Christ clip their leashes onto the slaves and go to the loveaeat and begin making out while the slaves get a GREAT view. The doorbell rings and the ladies are clearly nervous. A minute or so later, it rings a second time...

wanker-Jim | Jun 11, 2025
Christi takes Jeff’s leash, and Anne takes mine, and they lead us to the front door. The delivery lady seems stunne d when Christu opens the door. I keep my head hung partially down, hoping to hide my face. When Anne sees this she orders, “SlaveJimmy, please take the pizza from the lady, and put two on slaveJeff’s back, then hand the other twoto me, and I’ll put them om your back. As I straightened up, of course the delivery lady saw my face … and the chastity cage with Anne’s leash attatched. The dflivery lady let out a loud gasp, and laughed. “well, you all seem to be having fun, have a good day.” Then Anne puts the pizza’s on my back. As Christi and Anne lead us back to to the other ladues, Ican see up the back ofmy sister’s robe. Then when we crawl to othe table with the pizza, Amy asks if she can hold my leash while we eat.

nervousken | Jun 11, 2025
Everyone is very pleased withbhow well the slaves displayed themselves and the ladies took turns finding new and fun ways to feed the slaves pizza. Setting some on the pizza on their belly and not netting the slave use his hands. It's all lihhtbhearted and funny. Eventually, while Beth is having you and Jeff eat pizza off thw bottomnof her feet that she had stepped on a slice, Tara brings up an interesting topic. "Amy, you mentioned you've never been skinny dipping, how is that possible" Soon, everyone is watching and waiting for an embarassed Amy to answer

wanker-Jim | Jun 11, 2025
I didn’t want Amy thinking that I told anybody what she had shared with me. So, after a period of silence, I felt for Amy, so I lookat Amy and offer, “I’ll go skinny dipping with you Amy, if I’m allowed to. Actually, I haven’t ever skinny dipped either. I’ve always been afraid of skinny dipping in our pool, because I didn’t want to get caught by my parents. That would be hard to explain.” I laugh a little. Then I look at each lady, “If you ladies will allow it … with or without my chastity cage.” I give a little smile at Amy, while I wait for the ladies to answer.

nervousken | Jun 12, 2025
Anne hands Amy the key. "Your call, Amy" she says smiling. "Once you're in the pool, we'll join you two.. ifnyou like"

wanker-Jim | Jun 12, 2025
I smile at Amy, and then I whisper to he,, “You’re okay with this aren’t you? It’s one thing we can check off both of on our bucket lists.”vv I take Amy’s hand to make sure she wants to go.

nervousken | Jun 12, 2025
Amy nods and then unlocks your cage. "Maybe later we can scratch the second thing ai've never done off, too" then she slips off her bikini aand jumps in the pool naked

wanker-Jim | Jun 12, 2025
I smile, and even blush a little, thinking about her second thing, then I jump into the pool tight after her. We swim a lap across the pool together. AfteR the lap, I ask her, “There, that wasn’t so bad, was it?”As her answer, Amy splashes water at me,and we have a little sp;ash fight. Soon, weare taking turns swimming underwater, between each other’s legs.

nervousken | Jun 12, 2025
Amy gently pushes you to the edge of the pool and has you get out. She talks to Beth a little and then climbs out herself. Beth and Amy sit in chaira and you stand in front of Amy. With Beth coaching, Amy timidly begins to suxk yiur cock. As Amy gets used to it, Anne calls out from the pool "SlaveJimmy, you don't have permission to cum.... if you do, our deal about tonight is cancelled" At that, Amy gets a little more enthusoactic withbher BJ and slowly works a finger intonyour asshole.

wanker-Jim | Jun 12, 2025
Immediately, my head snas oveto look at Anne, just when Amy’s mouth is feeling very good. I call back to my sister, May I please cum here, Anne, PLEASE? “ My sister doesn’t even look or even acknowledge my plea. I see Tara standing next to Anne, looking at me and laughing. I don’t want to keep yelling to my sister for permission to cum, fearing that neighbors might hear. llooking down I despirately ask, “AAmy, could you please stop? Cou;d we please do this tomorrow>” Feeling my orgasm building, I look to Beth for help, she is looking up at me, and trying not to laugh. Almost panicing, I almost beg, “Please stop Amy … I’m about to cum. … PLEASE stop?”

nervousken | Jun 12, 2025
Amy stops and looks up, still kissing and licking your cock "And why should I, Slave? Aren't you supposed to obey me?"

wanker-Jim | Jun 12, 2025
To my surprise, I don’t back away from Amy, as she continues teasing my aching cock. Looking down at this young woman, I see her differently. “I … I … Yes, I am, Amy, butbut” I stopand I turn my head toward Anne, “PLEASE Anne, may I PLEASE cum?” Then with my focus on Amy again I plead, “Please Amy … I’m not suppose to cum.” … Seeing Then to add to my humiliation, Beth looking up with a big snile, and I realize that all of the women are watchung me.

nervousken | Jun 12, 2025
Eve and Christy kneel down next to Amy, both if them naked as well, and they begin kissing and licking your cock with Amy. Youblooknover at Anne in a panic. You see Tara is now kmeeling, her face between Anne's thighs eating her. Anne smiles at you "You can cum, but you have to promise to do something forbus"

wanker-Jim | Jun 12, 2025
I am about going crazy, I want to cum so bad, so I quickly agree,”Yes Anne, You know I will … you know that I’ll do about anything for you and all these ladies. Please … May I Please cum now?” I am so desperate to cum, I almost yell, not worrying about the neighbors right now. As I struggle not to cum, I see Beth sitting there, enjpying the show.

nervousken | Jun 12, 2025
"Are you sure?" Anne asks. Beth and Jeff are making out while enjoying the show

wanker-Jim | Jun 12, 2025
My throbbing cock is aching so badas I fight from cumming so hard. I look down with Christi and Amy and EVE teasing me to get me to agree. “Yes Anne, Ye. s I promise to do what you want, PLEASE, May I have your permission to cum?” permission to cum.”

nervousken | Jun 12, 2025
Amy auxks your cock hard and fast as Christ kneels behind you to licknyoue ass. Eve leans back to enjoy the show and Anne announces "Yes, you may cum, Slave"

wanker-Jim | Jun 12, 2025
Amy’s blowjob has me almost coming immediately, and the sensation of Christi’s tongue on my ass makes it even hotter. Still I try to hold bsck from cumming. As soon asI hear my sister give me her permission to cum, my hips thrust forward, and I have the most awesome orgasm. I look at Eveand then back to Anne … stunned that I could cum so hard.

nervousken | Jun 12, 2025
Amy chokes on the huge load and it spills ontobher chest and all over her face. She is laughing "Why did I wait so long? That was amazing!"

wanker-Jim | Jun 12, 2025
I am so thrilled with the blowjob, and for Amy, I drop down on my knees and I start kissing her. “DAMN, Amy that WAS amazing, and you are too. Ohh, I’ve never cum like that, I don’t think, ever.” I kiss her some more. “That was even better than any fantasy.” With my eyes still wide open, almost in disbelief, I laugh and start kissing her again.

nervousken | Jun 12, 2025
Everyone is around and clearly enjoyed the show. "How do you feel, SlaveJimmy?" Anne asks

wanker-Jim | Jun 12, 2025
I smile as I answer her, “I feel wonderful, Anne. … And Amy was incredible
[Delete] [Edit] … and then I add, “Thank for giving me your permission to cum, Anne..”

nervousken | Jun 13, 2025
"Wonderful" Anne beams at you. "And you'll pay for it tonight." With that, the ladies all getbup and go inside. They handcuff you and Jeff so your hands are behind your backs and then proceed to ahower and get dressed, do their make up and hair, all while you and Jeff watch, naked and cuffed. When every ladie is dressed for a night on the town, they turn theor attention to theor slaves. The ladies split into two groups. Anne, Eve and Beth take you, Christi, Tara and Amy take Jeff and head to separate bathrooms. You are instructed to shower while they watch, then they proceed to dress you in lingerie, a party dress, hose and low heel shoes. They even do your makenup and have a wig for you. Fully feminized, you meet Jeff and his ladies in the living room. He has gotten a similar treatment and you are both nervous aboutbwhat may be next

wanker-Jim | Jun 13, 2025
Holy crap, they obviously have something planned, since they have wigs and everything for us. I look at Jeff to see if he has any idea of what is going on. I squirm a little, nervously, looking at Eve and Beth mostly, since they are who dressed me. … these ladies sure come up with some wild ideas. Oh god, I hope they aren’t taking us OUT, dressed like this. … I get even more nervous. … Eve explained how I want to obey these ladies, and I promised Anne I’d do what she wants… but NOT go out like THIS .. I hope.

nervousken | Jun 13, 2025
"OK, I called the party bus to pick us up. We're going to one night club, we'll be there for about an hour and then come back home. Slaves, from this moment until we get home, you need to embrace your feminine sidem The morebyou embrace, the less noticable you will be." Jeff laughs "Holy shit. This is crazy. Are you sure this is a good idea?" Chrosti answers "We're going to a club about an hour away... it's mainly a lesbian club so you will be fine." Eve looks at you "You ok, SlaveJommy?"

wanker-Jim | Jun 13, 2025
I am terrified, when I hear the ladies’s plan. But I am determined to live up to Anne’s expectations as well as to Eve’s. “I AM nervous,” ,” I admit. “But I think that I’ll be okay. If this is what you ladies want, then I want t Fear surges through me when I hear the ladies plan, and I want to quit this game. But I CAN’T quit on Anne or Eve. Then looking into Ev’;s eyes, and I can no longer resist. “I’m… I;m nervous o do it for you.” I look at Anne and give a nervous smile. Now I realize that I am nervously tugging at my dress, “Can umm, Can I please hold somebodies hand?”

nervousken | Jun 13, 2025
Anne takes your hand and leads you out to the waiting party bus. As far as the driver cpuld tell, it was just 8 hot chicks going out for drinks and dancing

wanker-Jim | Jun 13, 2025
My heart is racing as we go to the bus, I whisper to my sister, ““These heels are hard to walk in.” Trying not to stumble, we get seated on the bus I turn to the ladies, “Holy shit, I don’t think he even noticed that Jeff and I are guys. You ladies must be VERY good with make-up,” I say quietly so that the driver won’t hear. Then I smile at Beth and Eve. :I don’t know if we’ll get away with it, at the club,” I say with a little less enthusiasm. Then I run my fingers through my wig, to adjust my hair. “Do you really think that we can pull this off? And nobody will know that Jeff and I are guys?” I ask, finally relaxing a bit.

nervousken | Jun 14, 2025
"Act like a lesbian, Jasmine" Anne whispers sternly

wanker-Jim | Jun 15, 2025
I am surprised by Anne’s instructions, but my sister calling me a lesbian, and her calling me by a sirl’s name, oddly tuns meon. Not needing to be told trice, I lean toward Anne, and kiss her on her li[s I feel a tightening in my crotch as I move closer to my sister, so we can make out.

nervousken | Jun 15, 2025
Anne responds by kissing you back and making out with you, even going so far to caress the fake breasts in yoir bra. Tara sits next to anne and kisses Anne. You watch for a moment before Beth taps you on the shpukder. "Kiss me, Jasmine"

wanker-Jim | Jun 15, 2025
I glance at Anne again, but she is busy, and seems happy kissing Tara. I thought that Tara and Anne might play around, but thus makes it much more real. I blush when Beth calls me Jasmine, but I immediately turn to her and start kissing her. I fondle Beth’s breasts and she seems to enjoy it, and that turns me on even more. Soon we are nearly crawling on each other as our making out gets more passionate. As we kiss, I see lipstick on Beth]s cheek and neck where I kissed her, and I am very aware that I have make-up and a dress o. I pause for a second, but I decide that , butit doesn’t really matter to me right no, and I resume making out with Beth.

nervousken | Jun 16, 2025
Beth explains "Nobody will suspect you and Jeff are straight guys here as slaves unless you do something to draw attention to it ,OK?" About that time, the party bus parked and everyone went into the nightclub. In the club, the ladies relaxed and danced and drank and made out with eachbother, making no distinction between Jasmine and Alicia (the girl name they had given Jeff) and other women. After a while, Eve sat next to Jasmine. "I would like to see you dance with that woman over there" she says, pointing out a slightly older, yet still attractive blonde. You are shocked... you had successfully not spoken to anyone so far at the club...

wanker-Jim | Jun 16, 2025
Scared half to death, I look at the lady, and then I look at Eve. I reach over and I give Eve’s hand a soft little squeeze, hoping to get my courage up. Standing, I balance myself in my high heels, I;ve discovered that myself in my high heel shoes. I’ve learned that walking just on the balls of my feet, at least I could walk thus way. I manage to walk over to the lady, in my softest non-fake voice, I ask her to dance. With a slime she accepts my offer, and so we go to the dance floor. The lady notices that I am wabbly in these heels, and after Istill struggle, we wind up slow dancing. We have a couple brief conversations, but we don’t talk a lot, I think the kind lady was more afraid that I’d fall, or break my ankles.

nervousken | Jun 16, 2025
After dancing, she invites you to sit with her. You look nervously towards your group and see several smiles and you are reassured and agree to join her. The waitress brings another round of drinks. "So, what bet did you lose to come out dressed as a lady" she asks, the smile on her face showing an amusement

wanker-Jim | Jun 16, 2025
Oh,” I say blushing, and lowering my eyes to the floor, then I look back up quickly, so GLAD that she isn’t upset. “I umm I kind of owe something to my sister and her friends, andthis is what they came up with.EvVen the dancing.” I look over atour table, then back at her, “I’m so glad that You aren’t upset.” I tell her, the ask, “How umm How did you know I wsn’t a woman?”… “Ohby the way I’m Jim …but Umm they are calling me Jasnine today.” I blush harderm but I keep eye contact with the lady. “I’m so gladthat you’re not ipset

nervousken | Jun 16, 2025
"Why would I be upset?" she asks

wanker-Jim | Jun 16, 2025
Still feeling uncomfortable talkingtoherabout this, I answer, “Well, I’m a guy dressed like a woman in a lesbianbar, I don’t Wnt you to think I’m mocking you or anything like that. This was NOT my idea. Umm, sometimes people umm redicule lasbians or gay oeiole. I mean, it has to look pretty peculiar having a guy in a dress and make-up and … and everything in a lesbian bar” I start squirming harder telling this lady wy why I’m wearing a dress andmake-up like a and … and she seems to accept me this way.

nervousken | Jun 16, 2025
She smiles and takes a sip of her wine "Honey, nobody believed you are a woman"

wanker-Jim | Jun 17, 2025
My eyes widen in fear, “You meanthat evertbody here knows that I’m a guy> Dressed like this?” I blush hard, and look at the ladies at our table. But, you danced with me, and invited me to your table, anyway? … I thought Eve and Beth did a goof job with my make-up. I was umm suppose to be just anotherwomab here.” More frantically I look toward our table again.”Why? … You’ve beenvery kind, thank you. But Umm I should probably go back to my friends.” Feeling so humiliated, now I struggle to get my balance as I stand up. Before I leave her table I say, “Thank you … umm, I’m sorry, what Is your name?”

nervousken | Jun 17, 2025
"Please, don't run away scared, Jasmine. I would like you to stay..."

wanker-Jim | Jun 17, 2025
“But, I …” I point to Anne and her friends, “I …” Really??” I ask, very curiously. I’m still blushing hard, and then I sit back down, “I guess it’s okay, they know that I’m here with you. Umm, to be honest with you, Eve told me I should dance with you. Do you kmowthem?” I ask,and I point toward Eve…. After taking my seat again, I straighten adjust my breasts, and I consciencely try to stop squirming. Then I ask the lady, “You really want to be seen here with ME?”

nervousken | Jun 17, 2025
"Why wouldn't I want to sit and talk with you? Is there something wtong with you that makes talking to you a bad thing?"

wanker-Jim | Jun 17, 2025
“Well no, it’s just that I’m sitting here in a dress, and a wig, and make-up, and these damn high heels,” I chuckle. Ummm guys don’t usually dress up like women. My friends over there said everybody would just think I was a woman … I guess I blew that, huh? Umm I might as well tell you, I didn’t plan to be here like this, the ladies decidedIshpild do this. I umm I’m so embarrassed being out in public, dressed like this, you don’t mind being seen with me?” … Just so you know, I”ve never wore a dress or make-up before.” I chuckle and blush ad smile a little.

nervousken | Jun 17, 2025
She looks at you meaningfully. "The clothes and make up are great. What gives you away is how ypu away os how you move.... Do you mean thatbyou have never even tried on panties before?"

wanker-Jim | Jun 17, 2025
Well, yes,I have worn panties and bras, but neveroutside of my bedroom … until last night. Anne had me wearing her panties and bra under my clothes last night during dinner, with our parents there, too. I umm I;m wearing panties and a bra right now.” I blush and Squirm harder. Umm Anne said she and Tara have known that I’ve umm borrowed her panties and bras for a long time. I squirm even harder andI tellher, “That’s part of what got me here today.” I look at this lady, so embarrassed. Why am I telling HER all of this?

nervousken | Jun 17, 2025
"Let me guess... you stole her undies to do naughty things and she decided to have you do embarassing things to keep your secret" she smiles

nervousken | May 1, 2025
Thank you!

nervousken | May 1, 2025
You should consider locking yourself in chastity!