Chicago Shemale and TS Escort or Hookup

USA > Illinois > Chicago

Transsexual Asian maid needing naughty RPing in Chicago, IL

Transsexual Asian maid needing naughty RPing in Chicago, IL

With a soft, pretty face and a small and compact little figure like this, who would ever guess I have this big boy stashed away ? It’s 6 inches long, uncut, and is quick to get bricked right up. I really have tuck her away well when I’m out and about, or else the secret of my transexuaity unveils itself haha!! I live in Chicago, Illinois down in Bucktown …

View profile of Alyssa, 27 yo

Would you run a train on a horse-cocked tranny in Chicago, IL?

Would you run a train on a horse-cocked tranny in Chicago, IL?

I’m an exhibitionist what can I say, and I know everyone loves seeing my monstrosity of a cock, put me in a museum already lmao! I’m a slutty little whore that loves to be degraded and slapped around. Pull my hair and make me take it like the animal I am. I’m not picky when it comes to guys, all I ask is that you have…

View profile of Asia, 23 yo

Big-booty tranny looking to go out to sex clubs in Chicago

Big-booty tranny looking to go out to sex clubs in Chicago

One of my biggest kinks is people watching me have sex with others. I’m a big sexy mama that loves to flaunt my stuff. I’m looking for a hot, hunk of a guy to go out to these clubs with in the city. I love to dress up, do my makeup, wear skanky heels, and a dress so short you…

View profile of Lexi, 24 yo

Come upstairs with a refined trans ? Lincoln Park

Come upstairs with a refined trans ? Lincoln Park

I might look like a straight and boring tranny on here. But I am rather kinky. I enjoy safe, yet sexy stuff with me. Think some light bdsm, domination and a slight dose of humiliation. I am into men over 40 years old, but I won’t call you daddy. I’ll be your refined trans lady friend. Picture us sharing a bottle of wine …

View profile of Victoria, 36 yo

Take a break from work with a tranny Latina from The Loop

Take a break from work with a tranny Latina from The Loop

My apartment is ideally situated to invite men home to decompress and relax in my arms. I literally like to unload a man’s pressure by blowing him out. There’s nothing quite like sensing a man relaxing under the soothing touch of my TS tongue around his cock. Moreover, what I prefer is to hook up with men who are normally afraid to live their fantasy of

View profile of Lola, 34 yo

Come up my Chicago, IL apartment for a quick hook up

Come up my Chicago, IL apartment for a quick hook up

I am Sylvia a libertine, a frivolous shemale of 28 who wants to make the most of my sexual life while I am still in my 20s. I live in Chicago proper, not too far from downtown in a small, but comfy apartment in which I’ve been for years now. And in all those years, I can’t count how many men I’ve invited up. Why do you think ? For …

View profile of Sylvia, 28 yo

Boost your sex confidence with a shemale in Evanston, IL

Boost your sex confidence with a shemale in Evanston, IL

You could say both, but do you prefer front or back ? Not just in terms of what you prefer, but also is in, would you want me to be the big spoon or the small spoon. Again, not as in sleeping, but as in spooning sex. Personally I love them both equally. As a versa shemale, I like to adapt to me partner’s preferences. If a man is more confortable to be on top, to ride my chubby …

View profile of VersaRose, 29 yo

Dabbling into being an escort, shemale from Chicago, IL

Dabbling into being an escort, shemale from Chicago, IL

I am not your typical shemale. Forst of all, I am not a real transwoman. I am a sissy, a cross dresser of 26 named Veronica who enjoys dressing up and acting up like a woman for pure pleasure. And in my case, the pleasure goes beyond putting on make up and choosing a dress that advantage my long slim legs. More often than not …

View profile of VeronicaIL, 26 yo

Dominant FTM with a real tranny clit – Chicago, IL

Dominant FTM with a real tranny clit – Chicago, IL

Call me the SheDaddy. I’m a trans FTM for female to male. I’m growing the cock I should have had all along. My long clit is popping out and is ready to be sucked and tickled with your tongue. Expect a real humid and wet area when I shove your face down there. I’m the SheDaddy as I enjoy dominating my partners. See those chokers and different leather straps on the wall ? Expect me to use an array of them when we …

View profile of SheDaddy, 31 yo

Giving online dating a try, shemale Northalsted, Chicago

Giving online dating a try, shemale Northalsted, Chicago

I ain’t joking, if I could find a girl as hot as me (but without a cock) who’s as chick as me, I’d fuck her. I’d even lick her pussy ! Which is something I have not done in a while. I’m 27 and started transitioning more than 7 years ago. But anyway, I’m not on this dating site to talk about women, I’m here to talk about me, and to …

View profile of JessyChic, 27 yo

Bears wanted for a horny versatile shemale in Chicago

Bears wanted for a horny versatile shemale in Chicago

Where’s my teddy bear at ? I hope he his hiding somewhere nearby Chicago. Maybe he’s been hibernating because I have not had enough actions lately. I am a true versatile. I can switch from dominant to dominated and to top to bottom. I’ll fuck with you, but you’ve got to understand that I’ll go …

View profile of MamaBear, 28 yo

Curly blond addicted to anal and rimming dating in Chicago

Curly blond addicted to anal and rimming dating in Chicago

My name is Penny, I’m a mystifying curly blond haired beauty with bolted up boobs. Forget about it if you want me to fuck me. My cock is off limits. However, I’ll do anything you want with yours. You see, I’m such a feminine shemale that I’m able to have full blown orgasm from anal sex. I’d even say that I prefer to my anal orgasm to regular ones …

View profile of Penny, 27 yo

Cheer me up with an ass pounding, tranny in Chicago, IL

Cheer me up with an ass pounding, tranny in Chicago, IL

I need our hook up to be hard. I want to shake in pleasure and desire while you ram me from behind. How do you like that position ?

View profile of SallyIL, 27 yo

Bring the heat to this chilly blond shemale in Chicago, IL

Bring the heat to this chilly blond shemale in Chicago, IL

Hey guys ! I hope you’re having a wonderful time wherever you are. At least, I hope you’re not as bored as I am up here in windy and cold Chicago Illinois. Every year it is the samething. As soon as temperatures drop, so does my morale. I just can’t stand the cold weather! Every part of my body rebels against it. And my lady cock acts like it would just crawl…

View profile of Windy, 24 yo

Mature trans is dating again in Chicago, IL

Mature trans is dating again in Chicago, IL

Hey there! I know this may sound weird, but this picture was taken by one of my ex lover. We met pretty often in, what I suspect, was his secret apartment to have sex without telling it to his wife. I bet she would not have been happy if she found out that he was dating a transexual. And that the transexual in question …

View profile of ClaraIL, 42 yo
More tgirls profiles :
12