One weekend, I wanted to take a trip dressed. I would go to our cottage that I have been cleaning up. No one knows I'm a crossdresser, including my wife. But my daughter wanted to come along this time, and my wife stayed home so much for my dressing and driving. But my clothes were already hidden in my car trunk, and I always bring my computer, so all is not lost. I can cam at night dressed.
I do get to dress when I'm up there and go on cam. So that night, at around midnight, I got dressed in white lingerie with a blouse, skirt, heels, oh, and, of course, my wig. My room is just off the rec room in what would have been the basement, and the bedrooms are on the main floor. I was on cam with someone, and he was asking questions. These are the same dumb questions guys always ask a cd.
Usually, with most at some point, I have to say, you know I'm a guy in woman's clothes. That either sends them running, or they say. Yes, I know. Tonight I got a lot of runners. How stupid can you be if I list my id as Sandy crossdresser or sandycd?
Both let the person know what they are looking at. Oh well. I keep trying, and I'm getting bored and ready to give up when the room door opens, and my daughter pops in. We are both startled, and I see her looking at me dressed, her Dad dressed as a woman.
She was the first to speak. What the hell are you doing dressed like that? I say, don't you knock before entering? Why do I need to knock? I could tell a light was on. I thought one of us left it on, so I just came in. Why are you not in bed sleeping, I say? Can't sleep, she says. We argue back and forth—some swearing. My constant yelling is, get loud! I should have just turned the computer off and gone to bed.
Most to the point is why you're dressed like that. She is just standing there looking at me silently. Finally, I say. Well, I like the look, and it feels right. Is that ok with you?
Calmly she says, well, I guess it's ok if you like to do that. Here are the questions. I just know it. Just great, I think to myself! So how often do you dress? Does Mom know? Do your friends know? Stop with the third degree. First, I dress when I get a chance. Second and third, no one knows. But now you do. Can you keep it to yourself?
I guess I can do that. What are you doing on the computer? Well, nosy, if you must know, I'm trying to find someone to chat and cam with. And then what happens, she asks? Are you looking for a guy or a girl? I say it makes no difference, but a guy usually comes on. Then you just chat? Yeah. She is still standing, staring at me. Something more must happen since you could chat, not dressed as you are. So tell me, what else? The guy might ask to show some skin, which could get more involved.
More involved? Like what? Showing more, I say. Like more, do you mean you show your junk? If that's what the person on the other end tells me to show it. Tells? What, you're not only a crossdresser but a sub-crossdresser? Yes, I say. Dad!! Are you a show-off on cam? Yes, I say. Can I stay and see what happens? No, I respond. I did say it could get more involved. So she says, how bad can it be?
How embarrassing that she wants to stay and see me almost naked. I bet by then I'll have a hard clitty. Just leave, please. Nope, I'm waiting. Now I'm stuck. Not what I had in mind that this would ever happen. Damm, I want to crawl into a hole.
Bing! Someone wants to chat. Aren't you going to answer? Here goes nothing. I answer. It is someone that I have known for a while on cam. He is very dominating. He gets me doing things that my daughter should not see. Do I tell him she is here? Maybe he will not have me do something I'm not proud of in front of her. But knowing him, the cam session will get me undressed, down to no panties.
Well, who is it, and what is he saying? I tell her it's a guy that I have cammed with before. He is my dom. He is asking if the slut is ready for my chores? Slut, she says? What the hell does he have you do? Are you going to tell him I'm here? I want to see what he is typing so I know what's going on.
Well, I think I have to, but this will not be pretty. So I told my dom what happened and that she is staying to watch. He is beside himself with joy that I have been busted and will perform in front of her. Turn on your cam, he says, and the cam is set off to the side. Oh, there you are slut.
It is knowing him that he starts mild—a few easy gestures. Like, show more leg. Hike upskirt and show more skin. Cross legs, spread legs so he can see between my legs. And that is just what he does.
She says this is it? What kind of dominating of a person is he? Weak ideas. I say just give him time. Bing! Someone else wants to chat and cam. I tell my dom of the person that wants to see. Like other times he says to tell the person my dom is on and that he gives out the demands. I'm starting to sweat. I know what's coming and hope my daughter doesn't go blind from what I'm about to do.
He says, stand and show us what you have on, bitch. He says he wants to see my ass while lifting my skirt. I have a thong on, so my ass is pretty visible to everyone, and when he tells me to turn so he can see the front, the bulge in my panties is pretty big. I try to ignore that she is there. But nope, she has to speak. Dad, are you hard? Do you get off on this shit? Did you shave? Is your junk shaved also? Yes, I say. The more dirty names he calls me, the more I love it. That's why I'm hard.
Well, whore, did your daughter see your sissy ass and that bulge in your panties? Yes, sir, she did. The other guy says, daughter? My dom explains to him what is going on.
Dad, are you ok with what is going on? You know if you keep going that I'm still staying. I say, are you sure you want to stay? I'm not leaving now. If you stay, remember that I love doing this on cam for anyone to watch. Maybe you should not see some things.
The dom says, ok, sit down, sissy, and pull up your skirt so we can see a lot of leg skin. Turn to cam and open your legs wide.
Let me know how your daughter is taking this. Ask her if we can see her.
My daughter says I will sit next to you, Dad, so he knows I'm still around. He says to turn on the mic so we can chat back and forth. We don't care if you have a guy's voice.
At least she has pants and a T-shirt on. Dom says her breasts and my breasts look about the same size. Can we see her ass? She stands and shows her ass with her pants on. She has a better ass, he says. Ok, honey, you watch and listen to what your Dad, the whore, bitch, slut will do for me.
Ok, slut stand and remove the blouse and skirt. Also, turn a few times for us. I do as told, and I can feel my wet panties from my leaking clit. My daughter laughs and says. You have wet panties, and your lingerie is sexier than mine. The dom says she always has wet panties for me.
My dom says, ok bitch; you can sit. Turn the chair toward cam so we can see between legs. Open those fucken legs wide. Excellent, we can see you are hard in those tiny panties. See daughter how hard she is? Yes, it is very hard, she says. Ok, let's get a little sexier. Stand up bitch, and drop your panties to your ankles. Face the cam when you do so. I look at my daughter, who is watching with wide eyes at my crotch.
I pull the sides away, tug them down, and let them fall to my heels. When I do, my clit springs up and free, and my daughter giggles. My dom says, see how her clitty stands erect? She gets off on these cam sessions with me, telling her what to do. I know I see, she says. She is so hard, and her sissy cock runs like a river. Ok, slut, turn around a few times, then take a walk so we see your clitty bouncing around.
So cute, he says. Now I want you to kneel on your chair ass to the cam. Spread your legs and bend over and show your ass pussy. Hmm looks tight. Should we loosen that up, daughter? What she says, how? Oh, she didn't tell you that she has toys? No, she didn't. Well, slut, grab a toy. I go and get my butt plug and some lube. Come on, lube it up and get it into your ass pussy while standing. This is so not my Dad, my daughter says!
There I am trying to get this plugin. Hey, turn your ass to cam so we see the plug going in. Plug slides in, and I stand there waiting for the following command. See how she is now waiting for me to tell her what's next. Take a walk again, then show the plug in your pussy by bending over and spreading your cheeks wide. How does it feel, sissy? It feels like my pussy is full, I say.
Well, sit on it. Now it can't get out. Spread your legs and play with clitty till I tell you to stop. But it might go off if I do that. Just do it, and it better not shoot your sissy juice. I start rubbing my clit, trying to rub it as little as I can and mainly massaging my sissy balls. Ok, you can stop. I can see my daughter looking at me wide-eyed. So embarrassing. Next, you need a different object in your pussy.
Get something. I go and get a black cock dildo that's not too big and long. Excellent, he says. Remove the plug and lube up the dildo. This is amazing that she is doing these things and is not embarrassed, my daughter says. Oh, I am embarrassed, but I have gone this far. I'll keep going, I say. A real slut, he says, isn't she?
I pull the plug out and lube up cock dildo. Push it in while bending over, he says. I start to push, and the head begins to go in. Go, Dad, go. Is she now cheering me on? Dildo goes in farther and farther till it is balls deep. Oh, this is fun watching her being a whore, my daughter says.
Well, bitch, don't just stand there, fuck that pussy. I start to push the cock back and forth in my pussy. It feels so good! Faster bitch faster. I am going fast now, and he yells, stop. My breathing is heavy, and I can hear my heart pounding faster. I want you to pull the cock all the way out a push it back in as fast as you can. I do my best, and the cock slides right in and out. You can stop, dom says. Now sit on it. I sit down. Cock is as far in as it can go.
She says, look, what is the other guy doing? We look at the computer screen, and he is stroking his cock. I hope he does squirt because I like to see someone's cock squirt its juice.
It is time to hump the dildo, so I can see your clitty bouncing around. I'm bouncing on the dildo, and my clit is hitting my belly. Up and down, I go fast. Stop, he says. Remove the dildo. Let's move on. Maybe the daughter can help this time. Daughter, find her big toy. Oh my, she says this is big, fat, and long.
Does this fit her ass pussy? She asks. Yes, he says. She has had it a few times.
So will you help her with the big cock dildo? What do I have to do? Jam it into her pussy! I don't know if I can do that. Come on; she could use the help. Well, ok, I'll try and see how I feel after I start this chore. Chore? Don't think of it as a chore. Think of it as getting back at your Dad for being a sissy whore boy. Ok. Bitch get on all fours, pussy toward cam. The daughter lubes up the dildo nicely. It will be kind of hard to get it in.
Could you do something before you push that dildo in her pussy? What, she asks? Could you strip down to your skivvies so it looks like a mistress doing her slave bitch? Your slut, Dad, will be looking forward. She won't see you. It will heighten this cam session. I suppose that will be ok, I think. I peek. She is now in her black bra and panties. I should not be peeking. She doesn't look as sexy as my lingerie. Here I am on all fours, with my drippy clit leaking everywhere.
She says I'm ready! Here it comes bitch. You better be prepared. Keep your head down and spread your pussy cheeks for me. I do as told and await the dildo I know will hurt going into my tight pussy. I feel the head against my pussy hole, and I try to relax so it goes in. Oh god, she is pushing too fast. It hurts. The head has now made its way in. With head in, my body is shaking because of the pain my pussy is feeling. Hurt bitch? Yes, I say. Get used to it because there are six inches or more to get into you.
My dom says, well, mistress, you're doing a bang-up job. It looks like you have done this before and are enjoying it. I am enjoying myself. I hope the slut is, also. My pussy is starting not to feel so tight. Suddenly, she shoves the whole cock in me right up to the balls so fast I fell to the floor. There I was, laying on my belly with a dildo like a flag in my ass pussy. Get up whore, on all fours, she says. I move to the position. I think she needs a spanking, my dom says. What? I say? Can you spank your sissy, Dad? Oh, yes, I can spank this sissy boy's ass. I feel her hand slap my ass hard. Owe that hurts! She keeps slapping away. Both cheeks are getting hot. Finally, she stops. Look at her red ass cheeks. How nice, my dom says!!
Oh wow, did you know there are like ten people watching, she says. How humiliating, I think. But I love to show off. She grabs the dildo again and starts to shove it in and out. She is twisting it as she fucks my pussy. Dom says faster. Fuck her good, so she knows when she gets up in the morning why her pussy hurts. Let's have her sit on it and bounce. I get up and look at my daughter in her bra and panties. Again I should not be seeing her in her undergarments. My clit is so hard and is trying to get harder with what I see.
Bounce, my dom and daughter say at the same time. I hold the balls of the dildo down while I bounce on it fast. Her clit is leaking so bad that the juice is flying all over the place, my daughter says.
She is doing so good I think it's time for her to play with that leaking clitty, my dom says. Leave the dildo in and play slut. I start to jack off slowly. Even though I want to shoot my sissy juice, I want to hold off. These things are getting me so horny, she says. Horny? He says. Can we see your panties to see if they're wet? My dom says to my daughter? I can do one better, she says. She removes her bra and panties and shows shaved pussy that is very wet. Nice and wet, dom says. Spread lips. She does it. I'm sitting here with my hand around my clitty and looking at her wet pussy. I'm going to hell for seeing her naked. Stroke sissy!!
My dom says this is the best cam session yet. Can you bounce a little on the dildo? I try, and that is too much for me; my clit is shooting its sissy juice out like a gusher, hitting her, me, the chairs, and the floor.
I am now spending all my energy. I'm drained. I barely know where and what has happened. You got your sissy, slut juice on my hand. Have her clean it up with her tongue, my dom says. Yes, clean me up!! She shoves her hand at me. I lick my juice off her. I am now your mistress after all that has happened. My dom says I'm done with her since she has unloaded. You can leave if your daughter is ok with that. Yes, she says leave us. I pull the dildo out, and I go to bed. She stayed, and at another time, my dom said she masturbated for him and the others. She even stuck my big dildo in her pussy. He caught it all on video but never showed me. My mind keeps returning to me now, having to call her mistress.
