The concept of cross-dressing was only suggested to him a few days ago, but now the idea has really taken over. Watch this sissy get their first taste of switching sides.
I think I'm going to start off by wearing some sexy stockings. The idea has always been enjoyable for me: get all dolled up like a little slut and then hopefully find someone willing to fuck me in the ass. I'm going to put on some sexy black underwear too - guys love panties and whatever they want, this sissy bitch is going to give it to them.
Wow, I feel so amazing dressed up as a woman! Now all that's left is for me to put some makeup on, attach this wig and then I'm all set. All of the men are going to want to take this sissy home. I look so sexy and I know that this isn't going to be the last time that I cross dress. I just really wish some hunk would come along and plow me like the girly slut I am!
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!
No one is home, the items are available and it would be a lot of fun. Combine those elements together and what do you have? A first time sissy getting in touch with their feminine side.
The makeup should be where to start - I need to make sure that my face is able to be feminine. If I just apply a little bit here and a little bit there - oh, wow! I didn't think that it would be so easy to turn myself into a lady. The hard part is over, now the fun is really going to begin with getting dressed up so I can have some solo fun in the kitchen. This cute outfit makes me feel so sexy. The stockings are great, the bra is incredibly soft and the panties make me feel like the woman I've always wanted to be.
Sissification seems like a lot of trouble at first, but I can see now that it's so worth it. I feel like a beautiful woman and I just can't wait to jerk off my sissy cock while fantasizing about being fucked by a big, strong man.
The first time cross-dressing is always the best. This guy is about to enter a whole new world of pleasure when he becomes a sissy for the very first time.
I'm going to start with some makeup because it's something I've always wanted to do. Perhaps a little bit of blusher here and a dab of eyeliner there - oh my, I really am quite the pretty lady! This is really turning me on, I have to get dressed up and see what I look like when I'm fully in the sissy transition.
This wig is fantastic and the color suits the outfit I got perfectly. I'm going to slip into these red stockings and and panties to finally seal the deal. I want to be able to live as a woman whenever I want. I feel so sexy and this cross-dressing thing is so enjoyable. All I need now is a guy to show me what it's like to really be a woman.
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