Find Trans in Chicago

Hey there. I'm looking for a crossdresser or trans girl for some sexual fun. I'm 6'2", 210, 7 in cut, clean, 50yo. Available Read More ...

Mature Male looking for a Trans women for a fun time . This could be ongoing, You must host , open to most anything.& Willing to travel

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 ...

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 ...

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 ...

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 ...

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 ...

So I'm free and available all day looking for men or trans girls or c.d. who want to do what ever they want to me I want to please you nothing 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 ...

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 ...

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.

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 ...

Face down ass up and lubed up in bed. Ready to have my ass up Send pics for address18 to 30 slim to athletic Im not trans or a cross dresser just a 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 ...

6'0", 195lbs, 9-10" bwc. Looking for a smooth sissy femboy or trans to hangout with and have some fun. I'm hard, clean, can host, Read More ...

Easygoing. Genuine. Clean. 27WM • 6’0” • 185 Looking for someone who appreciates good conversation and good company. Send your 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 ...

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 ...

Well hello there title says it all wife not giving me enough attention im married but not looking to change that but would love a cd or trans if it 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 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 ...

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 ...

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 ...

Looking for Trans or Passable Cd YOU MUST HOST NEAR 60148 for some fun I am verse so open to tops and bottoms I am open to different ages as long as 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 Details: 25 years 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 Details: 25 years 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 Details: 25 years 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 ...

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 ...

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. '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. 'm hosting here and I can travel, if post is up I'm still Read More ...

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

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 a regular oral sub, bi, str8, trans or gay I can host at times but for a consistent arrangement best if you could host me 62 6’ 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 6'4" with a BWC hosting CDs and Trans at a hotel in Lincolnshire Fetish for pantyhose, fishnets, heels, slutty lingerie Will be 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 ...

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 ...

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 enjoy giving facials or more and looking to film with a trans girl or fem cd. This is just for my personal collection but if you wanted a copy I Read More ...

Love a gurl that dresses all the time and is completely passable that wants a Puerto Rican dick to service on a regular basis. You must be able to Read More ...

Looking for black guys or CDs or trans that love blo n go or possibly more. I love getting serviced that’s all I’m looking for BLACK only

Just a guy in his mid 20s here. Looking to have some naughty fun... would love to have it with someone who is male to female transgender . Would be Read More ...

Hi. I’m a 59 year old WM looking for a CD or Trans for ongoing encounters. I am 6’2, in shape, not hung and you don’t have to be Read More ...

Hey guys, I have posted a few times and sadly I get some pretty sad replies. So, let me help you get some success and get some ass. I am looking for Read More ...

Huge preference of big assets. Pawgs to the front of the line. Would be great if you're into Greek but not required. Let me know something Read More ...

Who likes to show off their ass? Or bulge Maybe you like being watched from a far, from a distance maybe even closer than that? We set up a time and Read More ...

31, 6' 220 7"c blonde/blue Seeking a trans who wants to get tied up, used, toyed, and edged for several hours. I can host with planning. Read More ...

I’m open minded looking to get some very sloppy fellatio. I love to get my azz ate!!! I love big azz n nice nipples If u have a nice Dic 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 ...

Looking for big D for raw fun. Can travel. Hmu. Looking on the south side nwi. We can swap or you can just Top.

I’m a trans girl Are you tired of the same old thing? Well let's switch up and try some new and amazing stuffs ! I'm bubbly, sweet 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 ...

Happy Monday! I’m hosting top guys in Old Town! Looking for in-shape tops! Big plus for muscles, hairy bodies, and manly scents ;) No pic = 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 ...

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 ...

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 ...

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 ...

Horny early trans looking to be treated as a woman. I love to suck and get fucked. Please tell me what you would like. Can possibly host

looking for a TS (mtf) who has a big c0ck and is wanting to mess around, I have no experience with TS at all and would like to have a feminine trans 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 ...

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 ...

I am 34, total bottom, sissy / CD, probably trans but not quite there yet lol. I’m looking for an Alpha top Daddy that wants a loyal and Read More ...

Verse 5’7, 145lbs very fit Asian trans pre op. Visiting Chicago and looking to meet a handsome local. Hung tops are def a plus :) Please Read More ...

Hot in shape CD. Married and clean. Discreet and chill. Wife likes me to play. Looking for a top guy, a verse CD or trans to have fun. Like oral and Read More ...

Horny early trans looking to be treated as a woman. I love to suck and get fucked. Please tell me what you would like.

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 ...

Hi, I'm single, fit, white guy looking for a trans girl for something regular. I can host near O'Hare.

Daddy looking for Submissive smooth sexy trans woman to start a fwb with that will turn into my live in gf for long term. The fwb will be your Read More ...

Hi tall fit rugged masc bi guy here discreet need a hot mouth for a fun horned up session watch porn etc . Service or possible swap into other bi or Read More ...

I’m a submissive trans love dressing head to toe into tight leather, latex, vinyl . And spandex , love getting blindfolded and being put in Read More ...

I’m a handsome str8 37year old fit and hwp cis Italian man and I’m looking for a Trans woman who likes to give sl0w sl0ppy expert He@d. 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 ...

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 ...

Horny early trans looking to be treated as a woman. I love to suck and get fucked. Please tell me what you would like. Can possibly host

30 male 160lbs 5 11 looking for first time experience with a Trans person. Passable cross dresser welcome as well.

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'm 5'11, 30, 7 inches Ddf,safe play only Prefer CD's, trans and femme Can't host unfortunately Up all night

I'm 48 Femme BBW, don't smoke and you shouldn't either. It's okay if you're inexperienced and shy. I am a very enthusiastic Read More ...

Let’s do it rn trans im available for hookup Trans girl looking for fun top, bottom and vers I like to party and get high bj throat fk I like Read More ...

I can last forever pip for pic please be passable or close lol I’m 6 foot 200 and muscular can come to you or can ride around

Fully Discrete closet a sexy versatile trans available for both top and bottom I can host or come over to your place, 28 years old Native American, 7 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 ...

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 ...

Looking for a guy that is interested in roleplay on a regular basis that isn’t scared of try it ing new things. Clean DDF and expect the same, Read More ...

Clean 9in BBC looking for a very skilled edger this can be a one time thing or you can be my personal head doctor must be have great oral talent Read More ...

I am in Decatur, cant travel, been on HRT for 5 years. Very kinky, love exploring kinks, and I love dominant men and women. Hoping I can find someone 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 ...

Me: 28 white “straight” male , 170lbs 5”8 6.5inch You: C/D (it will work if you if a nice smooth and don’t dress), under 45 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 ...

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 ...