The mood is right, the house is empty and you're itching to try it out. After looking online for women's clothes, you've decided to embrace your sissy ways and try crossdressing.
Look at these women - they're so beautiful. I wish that I could look like that. Well, perhaps I can! Maybe I should start with some makeup to try and make my face look as pretty as possible. Lipstick, eye liner, mascara - the works. Oh, I do look quite a delight when I'm dolled up. This is so much fun.
What it really be wrong if I put that little girly outfit I got on? It fits me so nicely too, I'm such a girl and I love every second of it. These panties feel right and the stockings make my legs look fabulous. All I need now is to hit the streets and convince a guy that he needs to take me home and treat my sissy ass to a big, fat cock that I'm clearly begging for.
You can see that this crossdressing newbie has never transitioned before. Not that it matters, though - we're sure his first time becoming a sissy will be really fun!
You can see from the smile on his face at the start of this scene that he wants nothing more than to become a beautiful woman. It begins with some makeup application but soon enough it transitions into finding a set of bra and panties that he can wrap his sissy body in. The red lingerie outfit is just perfect for what he wants.
It's a little uncomfortable to begin with, but the experience is taken to a new level when this sissy slut looks down at the body she's created. In fact, the cross-dresser gets so horny that she starts to masturbate at the very idea of being dominated by a man as she embraces her feminine ways. While it might be a first time sissy, it sure as hell won't be a last time sissy!
He was looking forward to taking on this sissy slut and knew that a first-time cross-dressing was going to love every second of their erotic sexual adventure together.
Get in here and strip down for me. I want to get you all dressed up like a pretty lady so that I can eventually treat you to the cock that you so desperately want. Put that wig on and slip into those stockings - that's it, what a good girl. Oh, and don't forget the dress, I want that to drape over your body while I fuck you in the ass.
Do you like your first sissy adventure? I love it when I get to fuck crossdressers hard and deep in their tight asses. I'm going to make sure that you get a nice healthy load of cum deep inside you that shows just how hot you are as a woman. You did great today sissy and of course I'm happy to do this again - you were fantastic!
Sometimes things just happen, and that's okay. What things, you ask? Well, like you finding some lingerie and deciding to dress yourself up as a woman.
Man, I've always wondered what it feels like to be a woman, and the chance to do that is right here. Should I do it? Okay, well let's start with a little bit of makeup to make sure I look like a woman before I try these clothes on. I feel so naughty during my first time becoming a sissy bitch, but it feels so right at the same time.
I look fantastic! Let's get those panties on with the stockings to really amplify my feminine features. Oh, and what's next? Yeah - that's right, a little top to hide away my itty bitty titties. I'm so horny right now and I'm so glad that I did this. Cross-dressing is my new favorite thing. I'm going to do it as much as I can in future.
You've agreed to dressing up as a woman for the first time. You feel incredibly horny and just can't wait to experience what happens when you've completed the transition.
This guy is so hot - I hope that becoming a woman for him really makes me the type of person he wants to fuck. Perhaps I should slip into that dress and start to apply my makeup. Yeah, that's a good idea - let's get this girly show on the road! He's so hot and I know for a fact he's going to love pounding me in the ass.
Oh, he treats me like such a submissive sissy. Who knew that cross-dressing was so erotic? My ass is so tight and his dick is so big: the perfect combination that just makes me want to cum. I was a little worried at first that becoming a lady and having sex wouldn't be enjoyable, but now I've experienced it, I'm looking forward to my next sissy fuck session so much!