On one trip up to northern Wisconsin that I take to our cottage, I always get dressed up for the drive that is if the wife doesn't come along. No one has a clue that I'm a crossdresser. But this time, my daughter, who was twenty-four at the time, wanted to come along. 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 do get to dress when I'm up there and go on cam. So that night at around midnight, I got dressed in my white lingerie with a blouse, skirt, and heels oh and, of course, my wig. The room I'm in is just off the rec room. I was on cam with someone, and he was asking questions. The same dumb questions guys always ask.
Usually, 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. I'm getting bored, and I'm just about ready to give up when the room door opens, and my daughter pops into the room. We are both startled. Me to see her looking at me dressed as I am and her looking at 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, so I just came in. Why are you not in bed sleeping, I say? Can't sleep, she says.
Let's get back to why you're dressed like that? Well, to tell the truth, I like the look, and it feels right. Is that ok with you?
Well, I guess its ok if you like to do that. Here come the questions. 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, when I get a chance to dress, second and third, no one knows. But now you do. So 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 cam with. And then what happens? Are you looking for a guy or a girl? It makes no difference, but it is usually a guy that comes on. Then you just chat? Yeah and. The guy might ask to show some skin, and it could get more involved.
More involved? Like what? Showing more I say. Like more 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? Yes, I say. Can I stay and see what happens? No, I respond, I did say it can get more involved. So what she says how bad can it be?
How embarrassing that she wants to stay and see me like naked with I bet by then a hard clitty. Now I'm stuck. Not what I had in mind that this would ever happen. Damm, I just want to crawl into a hole.
Bing! Someone is asking to cam. Aren't you going to answer? Here goes nothing. I answer. It is someone that I know for a while on cam. He is very dominating to me. He really 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 that I'm not proud of in front of her. But knowing him, the cam session will get me naked.
Well, who is it, and what is he saying? I tell her it's a guy that I have cammed with before. 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 be warned this will not be pretty. So I tell my dom what happened and that she is staying to watch. He is beside himself with joy that I have been busted, and I'm going to perform in front of her.
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.
She says this is it? What kind of dominating person is he? Weak ideas. I say just give him time. Bing! Someone else wants to cam. I tell my dom of the person that wants to see. Like other times he says 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, my 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? You get off on this shit? Yes, I say. The more dirty names he calls me, the more I love it.
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 really 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. You can stay, but keep in mind that I love doing this on cam for anyone to watch.
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 legs wide.
Tell me how your daughter is taking this? Ask her if we can see her?
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 on pants and a t-shirt. 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 blouse and skirt also turn 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. The dom says she always has wet panties for me.
My dom says, ok bitch; you can sit. Turn chair toward cam so we can see between legs. Open those fucken legs wide. Nice, we can see you are hard in those tiny panties. See daughter how hard she is? Yes, it is very hard, she says. Ok, dom says let's get a little sexier. Stand up bitch and drop your panties to your ankles. Face the cam when you do so.
I pull the sides away and tug them down, letting them fall to my heels. When my clit springs up and free, my daughter gives off a giggle. See how her clitty stands erect? She gets off on these cam sessions with me, telling her what to do. I see, I see, she says. She is so hard, and her sissy cock is running 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 legs and bend over and show your ass pussy. Hhmm 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 plug in. Hey, turn your ass to cam, so we see plug going in. Plug slides in, and I stand there waiting for the next 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 cheeks wide. How does it feel sissy? Feels like my pussy is full, I say.
Well, sit on it. Now it can't get out. Spread 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 mostly 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. Nice he says, remove 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. She is 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 going faster. I want you to pull the cock all the way out a push it back in as fast as you can. I do as best as I can, 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 asks what is the other guy doing? We look at the computer screen he is stroking his cock. I hope he doesn't 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 now bouncing on the dildo, and my clit is hitting my belly. Up and down, I go fast. Stop, he says. Let's move on. Maybe the daughter can help this time. Daughter, go 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. Daughter lube up the dildo really good it will be kind of hard to get it in.
Could we get you to 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 in front of herself. 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 all over the place.
She says I'm ready! Here it comes bitch you better be ready. Keep your head down and spread your pussy cheeks for me. I do as told and await the dildo that 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 to 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. Oh well, 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. All of a sudden, 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's 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 get a good 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 if flying all over the place my daughter says.
She is doing so good I think its 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. Horny? He says. Can we see your panties to see if their wet, my dam 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 floor.
I am now spent of all 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 stays, 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.