Readhead Crossdresser

I love dressing up as a woman

Crazy crossdresser trying on lingerie

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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.

My sissy fantasies about getting fucked

A black guy loving studs wearing red lingerie

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Life can be pretty interesting at times, especially if you have sissy fantasies about getting fucked by a black stud. Oh, come on now - there's no reason to hide it!
 
He just looks so hot with his alpha black body that's ready to be appreciated. I'm going to start on my transition while he's here so that he can assist my sissy ass into becoming the most beautiful woman around. Once this cross-dressing is finished and I look like a lady, this ebony stud is going to do what I've wanted for so long.
 
His thick black cock in my ass just feels amazing. He's so thick and getting every inch of that incredible shaft deep inside my tight, white asshole. Not only is this a sissy ass fuck, but it's also an interracial one. Pump me full of cum and try to recover quickly, I can't wait for you.

My tight crossdresser ass is waiting for your dick

Hot crossdresser taking a hard cock

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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!

I am such a pretty lady

Crossdresser solo play in sexy lingerie

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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.

The very first sissy adventure

Crossdresser getting fucked on the sofa

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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!


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