Find Femboy Hookups in Chicago

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I’m looking for a fem smooth clean bttm host to have discreet fun with. A fwb would be ideal. I’m 5’8 170lbs clean 6” cut Read More ...

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Hi, I'm a clean bi bottom, masculine in public and a fem in the bed. I am 5' 7, 158lbs, slender, nice round ass and a little on the hairy Read More ...

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I'm a str8, curious white guy, 31, and I'd love to find someone around the Champaign area that would give a good, teasing rub with a nice, Read More ...

Hi. It's Tuesday. The heat and humidity have me stirred up. I am looking for today. Host in River North or travel short distance. Seeking slim Read More ...

I am very sensual bi feminine guy in this role and love kissing, mutual oral, and will bottom if we go there. Looking for a sensual top that likes Read More ...

I am very sensual bi feminine guy in this role and love kissing, mutual oral, and will bottom if we go there. Looking for a sensual top that likes Read More ...

I am very sensual bi feminine guy in this role and love kissing, mutual oral, and will bottom if we go there. Looking for a sensual top that likes Read More ...

Please guys, do not message me with your over 6 inch size, not what I’m looking for! My gf has used her 6 inch toy on me and it felt amazing. Read More ...

Im 25yo very sexy and nasty freak here! Looking for a Tall strong hung man that likes to have passionate to very dominate and hardcore rough play! ( Read More ...

BBC daddy here looking for a feminine bottom sissy to play with exclusively. My stats are 41yo 6’ 205lbs very clean and discreet. I can’t Read More ...

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Hello, I am an older dominant man that is 68 years old. Are you not drink? I do not smoke completely drug and disease free. i’m white single no Read More ...

Hello this may sound odd ,but i am straight curious and I need a feminine guy or gay guy that's want to experience with a curious guy Read More ...

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Looking for a hot top to spread me open. I like making out, oral, body contact and getting pounded. Im 29, 185 lbs, 5’10”, 6 in cut, Read More ...

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Dearest Domina, How may I serve Thee? Moi: HWP, experienced, sincere, sane, educated and kinda funny available for most feminine whims. Vous: Read More ...

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Im 45yo very sexy and nasty freak here! Looking for a Tall strong hung man that likes to have passionate to very dominate and hardcore rough play! ( Read More ...

I often have great chats when looking for dates. Then we get on the size topic. Apparently there are some size queens out here. I am a masculine man Read More ...

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Early 40's white male looking for new experiences. Interested in fem types to switch roles with, I am dominant type but would like to switch Read More ...

50 year old single d&d free top guy here in the northern suburbs near Grayslake. I am looking for someone 20s or 30s preferable who is near me Read More ...

I'm femme, black, discreet, curious, & chubby. Please be a pretty, good-looking, femme black woman. I like clean, slim thickie or curvy Read More ...

I enjoy giving facials and seeing what you look like covered. I also enjoy filming. While recording this is not required I do prefer to film. So if Read More ...

I’m a 37 year old professional in the city. I’m masculine and work out regularly. I’m looking for someone fem for something ongoing Read More ...

Smooth mature clean fem is looking to be spit roasted or gang banged at your place. Can be covered or bb if clean and ddf. Lmk if interested.

Need a sissy fem man be great if u like to dree too!! mature masc wm here 511 180 Please host for Daddy.

Just a 22M that sadly cannot host nor travel but more then willing to have some car or public play/travel with a cutie. I work second shift so Read More ...

52 Black male. Consider myself heterosexual and would like to find a femme person to service me in a dynamic that feels almost anonymous. Still take Read More ...

pretty fem ts girl looking for straight trans-guys for fun memorable times.Ready now and you can kindly message me . T_gram@shandis4play

-Please read it all- Hi, I'm a 44 year old married guy that is extremely curious about meeting a feminine trans. I've not yet had the 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 ...

Hi ladies. Im looking for two girls to join me and one of my girlfriends for a girls night. We can drink and 420 if preferred. No men or couples. Read More ...

Looking for first trans experience Good looking Ts, 25, 5'9", 190, 7" my first trans experience.. I am ddf and clean. I can host or Read More ...

If your a hot passable cd fem that dresses up and is a hot piece that can bounce on a 7.5 inch cut thick rod and is verbal. 5ft 11in hwp ddf. 40 Read More ...

I’m mwm discrete only interested in older men. I’m looking for someone who can host. I’m a normal straight married guy but like to Read More ...

27 masc wm 6 foot 215 6.5 needing to unload today in Orland Tinley area. More fem preferred but not a deal breaker. Cannot host, just looking for Read More ...

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 ...

Hey, 34 here in navy pier. Feminine, easy on the eyes, and can have you over on weekday evenings at my place. Looking for a genuine guy around my age Read More ...

Older male looking for fun times with a sexy femme cd. Can host most anytime. South suburbs. Midlothian/Oakforest area.

Older single wm looking to host a femme cd/gurl for very erotic fun times. Love oral making out top When replying please send a picture I can reply Read More ...

Been touring the State to see who gives the best head and so far it’s been a good start but looking to expand. Can be one time or ongoing but Read More ...

Hiii! I am a DDiva host here 4 a masculine strait man that knows what he wants. Im a feminine CD totally submissive gurl that goes down to the base. Read More ...

Looking for guys 21-55 who enjoy being dominated and controlled by another guy. I am into light bdsm, oral, love a skilled mouth/throat. Serious Read More ...

I'd like to meet with a total top lover for regular get-togethers. Someone that will help me out with my feminine needs. A man between 35 and 60 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 ...

As title says, older, masculine, fit dad looking for a fem or twink to please. Reciprocation is not needed but also wouldnt say no. Ongoing fwb thing Read More ...

Dear Daddies, I’m a 38 year old submissive guy looking for a confident, commanding Alpha Daddy to build a real long-term power dynamic with. Read More ...

First time in Chicago next month staying for a few days. Looking to connect with a guy that’s athletic, in great shape, muscular & Read More ...

First time in Chicago next month (June 15-18) staying for a few days. Looking to connect with a guy that’s athletic, in great shape, muscular Read More ...

Hi there, 40 yo guy here in Schaumburg looking for femme guy or cd to hang out. Anyone hosting. Please reach out and let plan. Hope to hear back Read More ...

I am a transgirl, ok so now the terfs scrolled away in looking for a wlw experience im a leather dyke in my 30s but a carry it well. Im a leather Read More ...

I’m a sexy hottie in my 30s who loves getting my juicy pretty pussy devoured by older ladies. I love riding faces and putting this pussy all Read More ...

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

I'm a straight guy and I'm looking for a very passable petite feminine gurl who loves pleasing with her lips. FTM bottom with no facial Read More ...

38-year-old professional guy in the western suburbs looking to connect with feminine trans women and crossdressers. I'm respectful, drama-free, Read More ...

Women who completely derail my attention tend to be soft-spoken right up until they decide not to be. Especially curvy Asian women who seem to be so Read More ...

I'm straight looking for a fem cd or ts who loves to give head, any race is fine just be clean, I'm just looking to have fun.

Curious first timer, I’m very curious about fem guys and cds I want to try something new. Must be fem or semi passable I’m open to just Read More ...

I seek one Mwm alpha here for work ? Or wants needs a loyal sissy by his side our secret I’m feminine smooth love lingerie heels makeup happy Read More ...

Straight top looking for a fem bottom to play with on a consistent basis. I’m 6ft 210lbs Black solid build clean and discreet. Please be a Read More ...

Smooth and feminine and love wearing cute outfits, I would love to give a nice discreet blow job this evening, my place or I’d even do this Read More ...

I’m looking to watch and learn. I’d love to start by observing—maybe watching Daddy go down on Mommy—and then being Read More ...

You must host. You must be in Lombard/oak brook/Elmhurst area. Bonus points for CD, fem or fit. Me: 39 mwm. 5’9” 155 lbs slim and Read More ...

Down for right now, CarPlay or somewhere discreet, looking for oral mainly, tall, Bwc, uncut, fit, masc, prefer ts cd fem twinks whatever. First come Read More ...

I am 50 swm 5'10" 190lbs, not hung but don't have a problem getting hard. I have my own place in the far north suburbs just west of Read More ...

Passable, feminine and discreet TS looking for a regular, safe, sane older man to please. Submissive girl here and connect best with calm, confident Read More ...

Mid 30s, very dedicated, presentable and passable as a feminine CD. Still trying to figure out where I fall on the gender scale, but I've been Read More ...

I'm looking to host a BBC, to worship his body, in any way he desires, and I mean, In any way. I am open to an after dark meeting in my home. Read More ...

So as the title says I’m 43 straight 6’ 190 blond hair green eyes. I’ve just heard that gay boys might suck the best dick and Read More ...

I'm a 41 year old black guy. I'm 6’0” and 205lbs. Very clean and discreet. Std free. I'm a top who loves to pound ass. Read More ...

I am going to be home all night Sunday, looking for big dick, fit guys to rail my femme ass! I'm 26, 120lb, 5'8, very slutty. I am thc Read More ...

Looking to try out hooking up with a ts or cd. Please be fem and ready. I'm mobile but can't host. I can get a hotel room if need be. 30 Read More ...

62 YO (with the mind and libido of a 35 YO) DWM and closet CD with a femme shaved slightly dad bod, is looking to find someone who finds the Read More ...

Dom Straight DL Daddy looking for Trans, CD, sissy’s, fem boy twinks to make porn with and post. I’m 39 5’10 and 190. Big beard, Read More ...

Str8 guy looking to be serviced. Looking for very passable, smooth, feminine gurl who likes being dressed up. Not looking for overweight bros Read More ...

Just as the title says, looking for a fem who enjoys slobbing on knobs to completion. Please be into crossdressing and some form of sissification. Read More ...

Im a younger feminine latina cd that is only interested in a straight curious married man that has an appeal for someone like me, be clean, honest, Read More ...

Nice looking Mwm needs a cute fem type Bonus points for panties garters etc. please be able to host A nice ass is always good

I’m 32, plus size Latina, 44 DD anx stand 5’5 looking for a femme woman to date or be fwb. Age, race, and size don’t matter. I do Read More ...