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The lost bet
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We had been dating for a while and now school is finished and we are lazing around one afternoon on a warm summers evening. We are at your house as nobody is going to be home until tomorrow. You mention that you are getting bored and I suggest a game. You shrug and tell me that you are bored with all the games. I sigh and ask you what do you want to do then?
It is almost comical as I see you get an idea and you tell me to wait a few seconds. You leave your room and do indeed come back in a few seconds carrying a dice. You show it to me and I can see that it is either “truth” or “dare”.
“Alright” I say, “but it has to be interesting and worth it. If you back out of any of the truths or dares then you have to do something!”
“Ok” you reply “but so do you. What do you want from me if I chicken out?”
I think about this for a moment, “How about you take jewellery shopping and I can buy whatever I like as long as you don’t need to take out a loan!”
You mull this over for a little while, “sure but if you back out then I get to fuck you in your ass”
I am a little surprised but guessed something like that was bound to be what you wanted. You had been trying to get me to do anal for as long as we have been having sex but I keep declining. I think about it and decide jewellery shopping might be worth the risk. I already had my mind on an expensive ring.
“Fine I said, but I get to go first”
You nod so I roll the dice onto your desk, it lands on truth. I think about this for a long time and I can se you starting to get bored.
“How many girlfriends have you had?” I didn’t like the question but I wanted to keep it moving.
“You’re my third one”
I knew of one other, so I look at you inquisitively.
“I had a girlfriend for a bit in primary school” you add freely. I am thinking that I was going to ask you about that for the next question and don’t know now what next to ask, but it is your turn now. You quickly take up the dice and roll Dare.
With an almost evil grin you say:
“I dare you to take off your clothes with the windows”
I am not surprised about this as it is often about sex with you. I make a motion towards the windows to close the blinds.
“you have to leave the blinds open!”
“That was not part of the dare”
“It was implied, and anyway, what sort of dare would it be if you closed the blinds?”
I knew I could not win so I sit back down on your bed. We have been naked together plenty of times and since your window faces the back yard I don’t fight anymore. It is a hot day so I already do not have much on; first I remove my denim mini skirt and then my singlet. I quickly remove my bra and panties and sit cross legged and my hands crossed in front of my chest, depriving you of a full view.
It is my turn to roll now so with my hands still crossed I awkwardly roll the dice, again it lands on Truth and I still haven’t thought of a question for you. I ask the first thing that comes to mind.
“How many girls have you had sex with?” I am expecting it to be 2, me and another girl, but I really struggled to think of a question.
“Three, including you”
I am very surprised by this and am shocked. Again you freely add more information.
“I had a three way with my ex before we broke up, she got all jealous afterwards so I ended it”
I didn’t know this about you and was still very shocked. You had been my only partner and you knew it.
You roll again and I get nervous when it comes up as Dare.
You look at me for a while and think about it. Ok, I dare you to go get us some drinks from the kitchen, the way you are, you can’t close any of the curtains or blinds or cover yourself with anything. You can’t touch anything that doesn’t involve making drinks!”
I knew it was going to be something like that. The kitchen is on the other side of your house and there are many windows facing every direction to walk past.
“what do you want to drink” I try to say as bitterly as possible but you are just smiling away
“Vodka and coke”
We are both underage but drink at parties when we can. You quickly tell me where everything is kept and I decide to do this properly. I get up and slowly walk out of your room giving you a nice show of me walking away. Once I am out of your room I run to the kitchen and don’t look out any of the windows as I quickly make the drinks and bring them back. We each take a sip and realise I had made them very strong. You don’t seem to mind though.
Now I roll the dice and this time it lands on dare. I take my time and think carefully about this. We drink our drinks while I am thinking and as you sit up to put your glass on the desk I see your erection and I get the idea.
“I dare you to take a cold shower, I want to see a proper soap up and wash!”
You look daggers at me but get up and head for the bathroom. I follow quickly and close the door. The windows are frosted in here so I don’t mind. I take a seat and watch you undress.
“Are you sure” you say to me looking down at your erect cock. I just nod and point to the shower. I realise I am a little turned on by this but don’t care as it might calm you down a little bit. I see you turn the cold water on full and get under it. Lucky it is a warm day otherwise I am sure you would have been screaming. None the less by the time you have washed and rinsed your erection is gone and I pass you a towel. You are shivering as you dry off and head back to your room wearing the towel.
You go straight for the dice but this time comes up with truth.
“Tell me about the first time you masturbated and your age”
I think about this but it was really only one question.
“I was twelve and in the shower. I had just started to get breasts and realised my nipples were a bit sensitive. After a little poking and tweaking I realised that warmth was radiating from between my legs. I explored the area with my hands and realised I was aroused. I knew what was going on so I quickly found my clit and started to rub it. It was over very quick without any real sexual thought. It was a small orgasm that just satisfied the urge.”
Seeing you are happy with the story I roll again. I see that you already have your erection back and I am hoping that it comes up dare, but it doesn’t, it lands on Truth.
I see you look almost relived so I ask you the same question you just ask me. You tell me a quick story involving some porn magazines you found in you dads garage when you were eleven. I am sure that you would have told me that story anyway without the dice. By now I am really starting to think that this game was not such a good idea and that I really have to try and think of better things.
You roll and Dare comes up.
“I don’t know about you but I am getting hungry, shall we get dinner?” you ask instead of a dare.
“Yeah, but what about your dare?”
“Ok” you begin and I know it is going to be bad “I dare you to dress how I tell you to as we go up the street to get take away”
I bite my bottom lip as you direct me to put on my denim mini skirt and then my singlet.
“That’s it?”
“Hang on your right” and you pull my skirt a little higher and roll the waist band under once so now the hem of the skirt is barely below my ass.
“There!”
I look in your mirror and can see that when I walk I will be showing some cheek and even though I am only a b-cup it is clear from the way the singlet sits tight around my chest I have no bra on, and to make matters worse almost like it is on cue, my nipples suddenly get hard and start to poke out. Meanwhile you dress yourself properly with a huge smile on your face and an erection bursting out of your shorts
I decide it is still better then anal sex and decide to go with it, thinking that I am really going to have to think of something embarrassing for you to do.
So we go out the house and walk the block and a half to the shops. The entire time your hand is on my ass and I am sure you are lifting the skirt. In the fish and chip shop we place our order and I can feel all the guys behind the counter staring at me as I try to avoid their faces. You direct me to sit on the only chairs that face the counter. I try to do it so as to preserve my modesty but even with my legs crossed I am sure everyone is getting a view.
We quickly get our dinner and I leave the shop before you do and hurry you home. I think you just liked walking behind me on the way back. As soon as we get in I go straight to the dice and roll.
“Fuck!” I say
“Too bad it landed on Truth” you reply with a smile on your face. “Let’s eat first”
I agree and we sit down to eat as I think of something to ask you
Finally I ask
“What is your most embarrassing moment” hoping that this will start to make you feel uncomfortable. You give me some story about wetting the bed on a school camp. I half think it is made up but have no way to prove it.
You roll again and I can’t believe it is Dare once more. You take some time to think about this one and then dare me to take a shot of vodka. I am surprised it is not something else sexual so I gladly do it. You pour a shot and I take it. It burns on the way down and by the time I get to your room to roll the dice again I can feel it having an effect on me.
I roll anyway and it comes up Dare. Having already thought of something that I am hoping you won’t do but do not break any of the unspoken universal rules (Nothing that will get us arrested, hurt or is impossible and is inside our means)
“I dare you to lick the toilet seat!”
“Gross”
“then tomorrow we are going shopping!!!”
“Fine if you want to play it that way, follow me”
And you did it too. I wished I made it more complicated but the alcohol was making my judgment a little impaired. I realised it was a mistake and that I should next try to get you to take shots as well.
You roll and again it is Dare. You stare at me for a while before ginning
“I dare you to let me tie you up”
I almost laughed, you started out on a high and I was thinking that you were losing your touch. All I needed was a couple more dares and I might even win this silly game. I give you my hand and you tell me to wait as you get scarves and neck ties ready. You tell me to lie across the bed and kneel so my feet are on the floor. I bend over the bed like you ask and you quickly tie my hands together and then tie them to the leg of the bed, my head is almost hanging off the other side of the single bed. As you walk around behind me I realise that I still have no panties on and try to protest but you quickly tie my legs together at the knees and ankles, the alcohol is really affecting me.
Without warning you lightly slap my ass and stroke my pussy. I protest but you laugh
“What are you going to do about it”
“That is not part of the dare”
“So what? It should have been”
“But it is not and it is my roll now, untie me so I can roll”
You just hand me the dice and tell me to through it. I do through it and it lands on the carpet in front of me and again it is truth. I can’t believe my luck.
“So what’s it going to be my pet?” you ask with an evil grin. I think for a while before saying.
“What are you planning on doing with me?”
“I am planning on fucking you in your ass tonight”
“You can’t do that unless I back out and you can’t dare me to either”
“Says who, but I am sure you will back out before I do”
I realise now that you really had thought this through more than I did and had a good luck streak that seemed uncanny. Still I had no intention of backing down.
I watched as you picked up the dice and rolled it in front of me so I could see; lo and behold it was dare. You didn’t say anything as you slowly took off your clothes. I could see you had a raging hard on and I couldn’t help but get turned on.
“I dare you to deep throat my cock!”
Now this is something I had been trying to do for you for a while. You had shown me porn where this is done and I had read allot about it in magazines. I was getting better as you always insisted that I practice. I am sure it was the alcohol that made me think I could do it tonight. And besides, if I get you to cum then you can’t fuck me in the ass and I still have a chance to win.
So I opened my mouth, you had to stoop a little beaches of the way I was tied to the bed but I am sure you had this in mind from the beginning. I had no use of my hands which was difficult as straight away you pushed your cock hard into my throat.
“Give me a chance to get warmed up” I managed to say as you prepared for another thrust. This time you placed you dick into my mouth and let me suck on it. You started slow thrusting movements as I sucked and tried to get you off as quick as possible. Your thrusts start to get larger and I give you a
“umm hmm” to try and let you know that I am ready. I open my mouth wide and try to position my throat so it is open for your cock. With my single you grab me by my hair and pull on it as you push your cock into my mouth. I immediately start to gag so you ease up and let me catch a few breaths before plunging back in harder than before. I gag again but you just hold my head there pushing harder. I try to shake my head and you release me and let me catch my breath. I choke out:
“This isn’t a fair dare, I can’t do it!”
“You agreed to it. Are you giving up”
“No! Try again”
I barely catch a breath as you take hold of my head again and ram your cock into my mouth again, I choke and start to cough and gag. You let me catch more breath and try again. I have tears in my eyes but I can’t do it.
“Well if you can’t do it then I guess I win!”
“This isn’t fair. You can’t do this”
I struggle against my bonds but they are too tight and I am stuck. I watch you walk around behind and feel as you slide you dick into my wet pussy.
“See you like this and you are going to love it up the arse”
“No I won’t it is going to hurt me”
You spit in my ass hole as you thrust into my pussy.
“Do you want to try deep throating my cock one more time?”
My throat is already very saw
“yes” I barely say, I close my eyes and open my mouth. I don’t feel your cock in my mouth it is my panties that you are stuffing into my mouth, quickly followed by a scarf to complete the gag.
“You had plenty of chances and couldn’t do it, don’t worry and relax, you will enjoy it!”
I feel your hands rubbing my pussy juices around my anus. I try to make noises through the gag but its barely audible. I feel you position your cock at my opening. You grab my hips and I feel you begin to push. I try to relax as I know if i struggle it is only going to hurt. This time I am thankful for the alcohol dulling my senses as I feel you push into me. I am grateful that you are taking it slow. I can still feel the pain as you push into me and I feel the head of you cock go in. Again you spit on my ass and begin to push further into me. I feel it when you are all the way inside me and I can’t help but tense. This must have been enough for you as suddenly you let out a moan and I feel your cock inside me explode your cum deep inside.
As you pull out I realise that I am crying. You take the gag off of me and untie me. I curl up into a ball on your bed and you tap my ass
“See that wasn’t so bad, you will enjoy it next time”
I couldn’t say anything. It hurt but I enjoyed being dominated, my pussy ached and I couldn’t stop wishing that you could fuck me so i could get off. Still, I let you watch as i rubbed my clit, still with tears on my face as I orgasmed like never before.
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Posted on : Sep 9, 2010
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Add Comment
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Commented on Oct 3, 2010
wow amazing story really loved the way it was written loved the build up and of course loved the tied up anal sex lol really really good story
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