Find Trans in Chicago

60 yo wm looking for a domme trans playmate 25 to 35 yo.looking to have playmates after 430 pm M/F Possibly weekends.no bs nsa.

can host or visit your place, and car meets are also available. I'm happy to travel to your home or hotel. I enjoy good company, and helping you Read More ...

can host or visit your place, and car meets are also available. I'm happy to travel to your home or hotel. I enjoy good company, and helping you Read More ...

…;;;;;8..2..6.;;;;;;; …;;;;;;;;;2. 44;;;;;;; ……;;;;;;;;9.2.8.0;;;;;;;; TE: laddyAndrea Hey you! I’m here to add Read More ...

…;;;;;8..2..6.;;;;;;; …;;;;;;;;;2. 44;;;;;;; ……;;;;;;;;9.2.8.0;;;;;;;; TE: laddyAndrea Hey you! I’m here to add Read More ...

I am a 57-year-old handsome clean discreet closeted white male daddy "silver fox" type and will be in Chicago next week for work staying Read More ...

I’m 45, 5'7", about 190, married and exploring independently with my spouse’s knowledge and consent. I’ll be in Chicago Read More ...

Trans woman looking for fun with tops or versatile guys. I’m friendly, discreet, and enjoy meeting new people. I can host and travel am Read More ...

Trans woman looking for fun with tops or versatile guys. I'm friendly, discreet, and enjoy meeting new people. I can host and travel am Read More ...

Hello, I'm 29 yrs old newly transgirl who is hoping to meet up with a chill and open man who would like to mess around hmu if ur interested.

Hi! Submissive straight male looking for a passable Trans Woman or CD! I’ve always wanted to serve a beautiful woman with a cock. :) Read More ...

26 white passable nice looking trans woman here looking to play I'm down to party and hang out.I'm hosting here and I can travel, if post Read More ...

Trans woman looking for fun with tops or versatile guys. I’m friendly, discreet, and enjoy meeting new people. I can host and travel am Read More ...

A nice looking trans woman here looking to play, I'm down to party. I'm hosting here and I can travel, if post is up I'm still Read More ...

I'm a versatile pretty trans lady with nice tits, clean skin and deeply passionate about connection, pleasure, and chemistry. I enjoy both Read More ...

Hi! I’m a feminine trans woman looking to connect with respectful, genuine trans-attracted men for link up and seeing where things go. Read More ...

I am a CD from the western suburbs of Chicago. I am looking to meet passable CD's, trans people, handsome men, sexy women, and couples. I am Read More ...

I am a crossdresser and I am looking to meet couples for NSA safe fun. I am also open to group fun. I am mostly a bottom, but will top women and Read More ...

I’m a (some say) handsome, in shape 50 yo male that knows what I want and what I am attracted to. Im looking to begin a friendship leading to Read More ...

I am a Transgender Goddess searching for a loyal and committed sub ready to obey. Looking for someone who wants to be used properly and knows how to Read More ...

A nice looking trans woman here looking to play , I’m down to party.I’m hosting here and I can travel, if post is up I’m still Read More ...

5 11 160lbs blue collar guy looking for first time with a trans person. Currently in mccook for the evening looking to get something going asap

Hello there I'm pretty much a straight latino 33 year old that's into beautiful trans women I'm pretty handsome I've been told Read More ...

In great shape for petite trans male or female around 98 too 115lbs. More petite the better. I am looking for a Companion or FWB homeless. I enjoy Read More ...

In great shape for petite trans male or female around 98 too 115lbs. More petite the better. I am looking for a Companion or FWB homeless I enjoy Read More ...

In great shape for petite trans male or female around 98 too 115lbs. More petite the better. I am looking for a Companion or FWB homeless I enjoy Read More ...

I'm generally attracted to more femme types, but I've also been in the mood to have someone down my throat and to be bent over with someone Read More ...

I'm a trans woman with a big juicy ass looking for a nice dick to suck balls to lick and maybe after I get it wet and sloppy you stick it in me Read More ...

Let released and relax, TE; katiej375 Come relax and release with a sexy ts lady, available to serve. Clean, sexy, naughty and talented. Can travel Read More ...

I’m a BBW early trans looking for a regular situation. I enjoy being treated as a woman. I love to suck and be fucked passionately.

I’m a ts lady here for fun looking for a guy that is interested in playing on a regular basis. Clean DDF and expect the same, I only into Read More ...

A nice looking trans woman here looking to play, I'm down to party. I'm hosting here and I can travel, if post is up I'm still Read More ...

A nice looking trans woman here looking to play, I'm down to party. I'm hosting here and I can travel, if post is up I'm still Read More ...

I really enjoy pleasing and love having my body touched and enjoyed. I'm hoping to connect with a man who's up for a good time with a trans Read More ...

Trans woman looking for fun with tops or versatile guys. I'm friendly, discreet, and enjoy meeting new people. I can host and travel am Read More ...

Let released and relax, Come relax and release with a sexy ts lady, available to serve. Clean, sexy, naughty and talented. Can travel and Can host Read More ...

I’m a 60 WM, 6’1, 200 lbs seeking a CD or Trans that is into kissing, body contact, mutual oral, grinding, perhaps more. I live in the Read More ...

I'm looking for a straight or curious hung guy who loves to fk and get sucked for regular meetups. I can host or travel. Send your pics and Read More ...

A nice looking trans woman here looking to play , I’m down to party. I’m hosting here and I can travel, if post is up I’m still Read More ...

A nice looking trans woman here looking to play , I’m down to party. I’m hosting here and I can travel, if post is up I’m still Read More ...

Sexy TS looking for a man who knows how to have fun and isn't scared of trying new things. I love to roleplay and I'm a very passionate Read More ...

I am a Transgender Goddess searching for a loyal and committed sub ready to obey. Looking for someone who wants to be used properly and knows how to Read More ...

A nice looking trans woman here looking to play , I’m down to party.I’m hosting here and I can travel, if post is up I’m still Read More ...

can host or visit your place, and car meets are also available. I'm happy to travel to your home or hotel. I enjoy good company, and helping you Read More ...

can host or visit your place, and car meets are also available. I'm happy to travel to your home or hotel. I enjoy good company, and helping you Read More ...

can host or visit your place, and car meets are also available. I'm happy to travel to your home or hotel. I enjoy good company, and helping you Read More ...

…;;;;;3. 47.;;;;;;; …;;;;;;;;;3. 76.;;;;;;; ……;;;;;;;;8. 42. 4.;;;;;;;; TE: alliet_28 Read More ...

Please note: **This is for Sunday (9/13/26) at about 4pm **Prefer a cd/ trans, but totally open to a male if you play the part. **Respond with pic Read More ...

Trans woman seeking a genuine deep connection with an open minded guy If youre craving a steamy experience with a hot trans woman with erotic fun Read More ...

Looking for a CD or trans that would want to worship each other. My fantasy is to be with a CD or trans for my first time and see how it goes from Read More ...

I am into trans and crossdressers I am a top 31 male and I'm short but I am blessed I'm not looking for now prefer during the weekday early Read More ...

A nice trans woman here looking to play,,If you’re interested in making this fantasy happen tonight and you can travel or host or arrange a Read More ...

TS here, packing 7+ inches. Looking for a straight, submissive guy who's ready to give up control and be used. First-timers welcome. I Read More ...

A nice looking trans woman here looking to play, I'm down to party. I'm hosting here and I can travel, if post is up I'm still Read More ...

Trans woman looking for fun with tops or versatile guys. I’m friendly, discreet, and enjoy meeting new people. I can host and travel am Read More ...

I'm a very good looking daddy 220 6 seeking trans cd twink fem to have some fun. NW Chicago I'm looking for host or travel

Tall, cleancut, stocky but still pretty hwp, WM with 8” & large b…s, had a hot time with a trans man. I’m hot and bothered Read More ...

…;;;;;8..2..6.;;;;;;; …;;;;;;;;;2. 44;;;;;;; ……;;;;;;;;9.2.8.0;;;;;;;; TE: laddyAndrea Hey you! I’m here to add Read More ...

H,402 M,765 U,1771 Te”” le”” gram: Ariana0671 I’m a trans girl Are you tired of the same old thing? Well let's Read More ...

A nice looking trans woman here looking to play , I’m down to party.I’m hosting here and I can travel, if post is up I’m still Read More ...

A wnice looking trans woman here looking to play , I’m down to party. I’m hosting here and I can travel, if post is up I’m still Read More ...

Hi, I’m 5‘9“ drug and disease free looking for cock suckers and cock worshipers I am 100% top and I desire for all cock worshipers, Read More ...

Trans woman looking for fun with tops or versatile guys. I'm friendly, discreet, and enjoy meeting new people. I can host and travel am Read More ...

A nice looking trans woman here looking to play, I'm down to party. I'm hosting here and I can travel, if post is up I'm still Read More ...

…;;;;;8..2..6.;;;;;;; …;;;;;;;;;2. 44;;;;;;; ……;;;;;;;;9.2.8.0;;;;;;;; TE: laddyAndrea Hey you! I’m here to add Read More ...

Heyyyy, I’m a pretty normal straight guy. I’m not looking for anything too crazy. Really only into girls, but I guess I could be open to Read More ...

Sexy TS verse looking for a man who knows how to have fun and isn't scared of trying new things. I love to roleplay and I'm a very Read More ...

A nice looking trans woman here looking to play , I’m down to party. I’m hosting here and I can travel, if post is up I’m still Read More ...

looking for straight and masculine men. I'm verse and very kinky. Super low key here. Ready to get on my knees and do my job asap Send pics and Read More ...

Submissive seeking aggressive and very kinky more creative and extreme, I’m seeking individuals that want to force me to full fill your ever Read More ...

Hello, sexy trans girl who is hoping to meet up with a chill and open man, married or single who would like to mess around and try something new. hmu Read More ...

Confident trans mistress down for playful, consensual connections, kinky vibes, and unforgettable chemistry. Respectful, discreet, and ready to have Read More ...

I'm a bi white dude who enjoys being more dominant while with a woman but more submissive with a guy. Really want a beautiful Trans Woman Read More ...

Looking for passable trans or fem bottom that could preferably host. I wamna come over and pound that tight hole until I cum deep inside of you. Read More ...

I am into giving facials and enjoy giving them. If you are into receiving them then lets chat. Ideally I would like to film it pov style and can give Read More ...

Hi, we are a couple looking for a threesome with a cis or trans woman. He is 28, cis man, tall and hung. I am a 34 yo trans woman. We are both clean Read More ...

43/closeted bi, Logan here. I have some experience with guys, but always was the top. My curiosity is getting to me and would like to try and bottom Read More ...

Looking to worship/ service a nice c@#k, deeep hungry throat trans women here hottestjenny7 EXCELLENT ORAL SKILLS, intend to please, sit back Read More ...

A nice looking trans woman here looking to play, I'm down to party. I'm hosting here and I can travel, if post is up I'm still Read More ...

If you're into this kind of fantasy and want to make it happen TONIGHT, I'm ready. If you can host or have a motel room, or I host Read More ...

passable closet cd. If this scenario is something you would like to play a part in TONIGHT and you can host or have motel room i will be there Read More ...

Let released and relax, TE; katiej375 Come relax and release with a sexy ts lady, available to serve. Clean, sexy, naughty and talented. Can travel Read More ...

A nice looking trans woman here looking to play , I’m down to party.I’m hosting here and I can travel, if post is up I’m still Read More ...

A nice looking trans woman here looking to play , I’m down to party.I’m hosting here and I can travel, if post is up I’m still Read More ...

Sexy TS looking for a man who knows how to have fun and isn't scared of trying new things. I love to roleplay and I'm a very passionate Read More ...

I want a semi passable/ passable trans gurl or cd to use both my holes. Looking to swallow some gurl cum and then be bent over.

Trans woman looking for fun with tops or versatile guys. I’m friendly, discreet, and enjoy meeting new people. I can host and travel am Read More ...

white passable nice looking trans woman here looking to play, I'm down to party and hang out. I'm hosting here and I can travel, if post is Read More ...

i am a post-op trans woman looking for some cute men to suck :) i love giving head, and have been told i'm quite good at it too but i'll Read More ...

Trans woman here with amazing body easy going and naughty I'm waiting for you right now and ready to satisfy all your desires. Please be real Read More ...

WM professional adores CD and trans ladies especially 35 plus. Love dating and open to LTR. Love to hear from you.

Trans woman looking for fun with tops or versatile guys. I’m friendly, discreet, and enjoy meeting new people. I can host and travel am Read More ...

A nice looking trans woman here looking to play , I’m down to party. I’m hosting here and I can travel, if post is up I’m still Read More ...

A nice looking trans woman here looking to play , I'm down to party.I'm hosting here and I can travel, if post is up I'm still Read More ...

Any crossdresser or trans hosting around N or NW burbs? Incredibly h*rned up today and looking to get head and possibly top. Stats for stats? I can Read More ...

I’m a ts lady here for fun looking for a guy that is interested in playing on a regular basis. Clean DDF and expect the same, I only into safe Read More ...

I’ve been curious for a long time and recently have realized that I haven’t made more of an effort to explore because I’m not super Read More ...

Sexy trans woman, 29, 5'9", 190 Ibs, 8". down for play. Clean, DDF, and expecting the same-only into safe, DDF men. Versatile Read More ...

Looking to have some fun. I love to please. I am a h**ny trans who loves to have her b**bs played with and su**ed. I'm really happy. Whether Read More ...

Sexy TS looking for a man who knows how to have fun and isn't scared of trying new things. I love to roleplay and I'm a very passionate Read More ...