Come here you little slut. This alpha male has some cock for you and he's going to make sure you're as feminine as possible when it's delivered deep in your ass.
Get in here and start to dress up for me. I want to make you as pretty as possible before we get down to business: I like my asses to be as sissy as possible before they get fucked. That's it baby, put that wig on and pull those stockings up - you're going to feel like such a woman once I get it inside you.
Your first time as a sissy bitch must feel pretty incredible, right? Having this big alpha cock in your asshole. I know that you want me to pump you full of cum to prove just how amazing of a woman you are. That's exactly what I want to hear - now that I know you're happy to do this again tomorrow, I'll give you the hot cum you rightfully deserve.
He's never been with a sissy before, but that doesn't mean he'll go easy on that ass. See this cross dresser get fucked hard by a big fat dick.
I was a little nervous to begin with, but now that I'm getting my dick sucked by this sissy I'm more than into it. It feels so good to have a little bitch in front of me that will do whatever I want. I think I'd like to fuck that ass pretty damn hard, so how about I get untied and go to town on that rear.
That's it, you sissy slut, bend over and take this cock like the cross-dressing sex addict you are. I'm going to dominate you with my huge dick and make sure you never want to get fucked by anyone else again. My first experience with a sissy was great: I can't wait for the next time that I get to treat a little cross-dressing slut like the sex slave they are.
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!
This is the first time he has cross dressed and it's going to end in a very sexual fashion. A hung black stud is just waiting to get his hands on that sissy ass.
I think I look really pretty and from the way this stud is looking at me, I'd say that he thinks the same too! I'm going to put on lots of makeup so he adores me and then treats me like a slut. Yummy, this big black cock is just as good as I imagined. Being a woman is easy! Now how about you give me what I really want, you ebony stud?
Fuck, I love being bent over and fucked from behind. This dude has a massive cock and it feels incredible in my tight ass. The lady in me just wants to make sure that he's fully pleasured - I'm going to take this dick for as long as I can and hope he cums deep inside me. It would be so hot to get his delicious cum to wrap up my awesome first time as a sissy.
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!