My first time becoming a sissy

Crossdressing photo session play

share gif:

 
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!
 


  • Categories

  • Bonus Sites

    Curious Porn Pass | Hardcore Mega Site

    curious porn pass

    Featuring 10 radical and hardcore porn sites all for one low price, under $1 a day. Featuring daily updates and hot hard real HD videos, you'll always have something you like.

    Shemales Fuck Couples | Shemale

    shemales fuck couples

    If we were going to do it, it'd be with a tranny as she thinks they're really hot. So we are having our first ever male, female and tranny threesome! I can't wait to fuck and get pegged.

    Tranny Newbies | Hot Tranny Porn

    tranny newbies

    He didn't know what to expect at first, but she certainly made sure he was taught the ways of having sex with a tranny. With that cock sucked and asshole lubed up, it was only a matter of time

    Cuckolding Humiliation | Amateur Cuck

    cuckolding humiliation

    You have a tiny cock. A woman as gorgeous as me should not have to lower herself to the level of being with a guy that's as small as you. I'm taking a black cock, you're watching me do it

    Bisexual Newbies | Bi Threesomes

    bisexual newbies

    Fuck, getting rammed in the ass by another dude while this hot babe sucks on my dick is pretty hot. I'm going to cum in a matter of seconds if they don't slow down. Why did it take me this long?

    Pegging Newbies | Hot Strapon Sex

    pegging newbies

    I'm going to milk your cock for a while from behind and then, when you least expect it, I'm going to put this big fat strapon deep into your ass to teach you a lesson in submission.

    Black Cock Worshiping | BBC Porn

    black cock worshiping

    I am going to be taking two cocks at the same time and both of them are going to be big black cocks. That's right, your white woman getting violated by two hung black guys

    Gay Newbies | First Time Gay

    gay newbies

    Suck on it like your life depends on it. Blow that man and get ready because he's going to flip you over and go to town on your rear. See how fun it is to get fucked in the ass by a dude?

    My Wife Fucks | Fucking Your Wife

    my wife fucks

    I'm going to make sure that this cuckold experience is enjoyable and that getting fucked by someone else will be fun, but I didn't think it would be this good. His cock feels so nice!

  • Shemales Fuck Couples | Shemale

    shemales fuck couples

    If we were going to do it, it'd be with a tranny as she thinks they're really hot. So we are having our first ever male, female and tranny threesome! I can't wait to fuck and get pegged.

    Curious Porn Pass | Hardcore Mega Site

    curious porn pass

    Featuring 10 radical and hardcore porn sites all for one low price, under $1 a day. Featuring daily updates and hot hard real HD videos, you'll always have something you like.

    Tranny Newbies | Hot Tranny Porn

    tranny newbies

    He didn't know what to expect at first, but she certainly made sure he was taught the ways of having sex with a tranny. With that cock sucked and asshole lubed up, it was only a matter of time

    Cuckolding Humiliation | Amateur Cuck

    cuckolding humiliation

    You have a tiny cock. A woman as gorgeous as me should not have to lower herself to the level of being with a guy that's as small as you. I'm taking a black cock, you're watching me do it

    Bisexual Newbies | Bi Threesomes

    bisexual newbies

    Fuck, getting rammed in the ass by another dude while this hot babe sucks on my dick is pretty hot. I'm going to cum in a matter of seconds if they don't slow down. Why did it take me this long?

    Pegging Newbies | Hot Strapon Sex

    pegging newbies

    I'm going to milk your cock for a while from behind and then, when you least expect it, I'm going to put this big fat strapon deep into your ass to teach you a lesson in submission.

    Black Cock Worshiping | BBC Porn

    black cock worshiping

    I am going to be taking two cocks at the same time and both of them are going to be big black cocks. That's right, your white woman getting violated by two hung black guys

    Gay Newbies | First Time Gay

    gay newbies

    Suck on it like your life depends on it. Blow that man and get ready because he's going to flip you over and go to town on your rear. See how fun it is to get fucked in the ass by a dude?

    My Wife Fucks | Fucking Your Wife

    my wife fucks

    I'm going to make sure that this cuckold experience is enjoyable and that getting fucked by someone else will be fun, but I didn't think it would be this good. His cock feels so nice!