Chicago Men Seeking Men Classifieds
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May 19th, 2025
Professional Wants to Settle down in Chicago... Gay Man for Commited Relationship
Hi, I'm Hal a nurse practitioner ultimately looking for gay marriage in Chicago. I'm not too particular about race, religion or political bent really. As long as you are a loving and caring person. If you have a hot temper do not contact. I'm over that crap! Willin...
Star Wars fan looking for his Obi-Wan Rudy seeks man in Chicago
Name is Rudy and I'm looking for a man in Chicago. Are you out there somewhere? I am looking for you. I love Star Wars. Possibly a little nerdy ;)
Would like to have light saber fight with the right guy. Private message me @GayNerd4m...May 18th, 2025
Just turned 21 and new to the scene in Chicago I am Kyle and I just recently turned 21. Happy birthday to me! This is hard for me because I am new and don't know what to say. I guess I just want someone who can play video games and take me seriously.
I don't care about age or anything but anyone up to 50 is ok. You must be funny and educa...
Holy Capped Crusaders! - We'd Make a Hot Dynamic Duo! Bottom Boy Wonder searching for his BAT-man. Twink 24 years old, 5'9, 160 pounds in Chicago seeks cosplay leading man to form a dynamic duo. We may not exactly fight crime, but we will have lots of sexy roleplay fun. Let's travel and go to conventions and events and contests! We'll take the world by...
I'm Your Sexy Guy... ALSO BI ππ¦ Chicago I am here to rub you down to a state of complete relaxation and release from all your stress. I am a student of somatic massage and would love to use my techniques all over you. I only do out-call at the moment. I am located in Chicago but I am happy to travel anywhere,,,
Gay M4M - Deep Rub...
Sexy, body builder, age 26, looking for man in Chicago Hey, Kevin here, I am looking for a partner who can work out with me. I want a dude who is open to anything, like a rough workout, if you get me and wants to just hang out and have fun.
I'm open to most anything. Do you have any ideas? Message me if you are in this area and want to hang out....
RuPaul Step Aside! Fashionista looking for my model boyfriend! Drag Queen Extraordinaire Silvia
My name is Silvino but on weekends my name is Silvia! I love dressing up and I do drag shows. I am not totally flamboyant but I do like being noticed. I love classical music but I also love, love love dancing the night away at clubs!
How about you? Check my pr...
πͺπ I'm All Tha Chocolate You Could Need πͺπ Hey I'm new to dating sites but I'm ready to give it a try and see who might message me. I'm wanting to get out and have some fun. Yes I'm black and yes I have a thick π but I'm so much more than that. Also I want you to know that I love all shapes and sizes of men, I just want someone I can conn...
Small, smooth body big heart Smooth 19 years old in Chicago
Hey guys, I am Jon and I am 19 years old, smooth, about 120lbs but fit. I like to do karaoke, dance and travel. I love the male body and enjoy sex anytime, anywhere! I'm a passionate and attentive bottom only plus a cook a great meal! Check out my profile and send a m...
SUGAR DADDY ππ¨βπ¦° π¦Looking 4 Play Boy M4M Hey there babe, I'm a 25 year old male who is searching for another guy to play with and spoil. I'm strong and muscular, I drive a beautiful car, I can take you to do things you've always desired π€ It turns me on so damn much to find a cute little man to play with and take care of. Let me be D*dd...
Gay Body Rubs - Need Sexual Relief? - Yeah, You Need SAL!... Sal here in Chicago to melt your stress away and relieve that pent up sexual tension like no other. I host and offer full amenities and services to my gay clients. All men are welcome as well as couples who need to unwind and spice up the day the right way. I serve gay, bixsexual and bi-curious clie...
Discreet meet only in the Chicago area!!! I am Jamali here in Chicago for a while doing some work for a tech company so I can't get too involved with anyone. I'd like to get out and experience this town, the party vibe and the men in it. I'll be going home in a few months. If you are iinterested in an Asian-Indian man then come check me out...
π―REALπ―HANDSOMEπ―MANLY You ready for some manly gay sex here in Chicago? I know I am, I made this ad to make a nice BF to fuck or fuck me.. We can even find some other sexy guys to have some sex with too.. I love partyingβ¨ and having group sex. Do you like to take it or give it? I will give you something to suck on alri...
Spanish Speaking Handsome Guy Hola a mis chicos. Estoy buscando a un hombre que esté en forma y musculoso que le guste jugar y comer. Me encanta cocinar. ¿Quieres que te prepare la cena? ¡Lo haré! Golpéame. @ChicoGuapo32
Hello my guys. I am looking for a man who is fit and muscular who likes to...
Shy guy wants someone to bring him out of his shell Shy guy for male in Chicago
Hey, I am Scott and I am 27. I am not an extrovert but once I get comfortable with you I can be funny and a little out there. I am not the sort who like attention too much but I do love clubbing and sports. If you are into jetskiiing it's a plus, otherwise, anything wate...
Navy Vet wants to meet partner for life I am a Navy vet currently on reserve duty. I live in Chicago and I love it here. I wanna meet a guy who is appreciative of my service career but also likes to travel and have adventures. My name is Tom and I am African-American, age 29. Message me to exchange photos and to meet up. Willing to t...
Bryan for Hot Male-on-Male Action in Chicago Bryan M4M in Chicago
Hey guys! I'm Bryan, looking for some hot male-on-male action. I want to meet a guy in the Chicago area who is ready to get down and dirty with me. See my pics and contact info @Bryan24m4mX.I'm primarily top but can switch for the right guy. I love getting my big thick cock suc...
Smoke and Leather! Smoke and leather go together. I'm Toby, 32yrs, 6'0, 200 pounds, extra large, living in the Chicago area, a hairy thug, def top gay man wanting to pound gay, bisexual and bi-curious men. Just be ready to pleasure me while I chain smoke. I don't care if you smoke or not just be damned grateful that y...
SciFi lovin' guy getting lonely in Chicago I love SciFi TV and movies. I am Will. I am 31, tall and muscular with light brown hair, grey eyes and tan skin. I work and I have a nice home and car. I need a friend with benefits! Send me a private message to @WillSciFiFan if you want to swap pics and maybe get together and cuddle up watchin...
Caramel Complexion male seeking night of pleasure Hey guys! I'm a gay man, looking for someone to discreetly play with. Hookups are great but an ongoing FWB would be even better. I'm age 31, 6'2 and have a thick.. well, you'll find out ;)
Let's swap pics first and then meet up in Chicago.
CaramelSurprise31...
Spanish Gay Man Needs New Owner... Hi, I'm Shaggy a sub from Madrid, Spain originally and just moved to Chicago about 5 years ago. My English is good, I'm 32 years old, 5'9, 170 pounds, very skilled in bed and very passionate. I need someone to own me, take me, use me and protect me if only for a short time. What do you say amigos? I...
Caribbean Queenie Likes hung guys Drag Queen for Hung Man in Chicago
Hey ya'll!! I am Queenie (real name Wayne) and I adore drag shows and dressing up! I am a little (yes, only a little) eccentric and I love part-ayy-ing! I am 38 and 7 1/2 *wink wink* and I am just wanting to meet and date a really awesome guy who can understand me...
Alex's Huge Throbbing Cock in Chicago π¦π¦ New to the scene, willing to try anything!
Thanks for checking my ad. I'm new to this. My name is Alex (hmu @AlexThrobbingCock4u) and I love fucking and getting my huge throbbing cock stroked and sucked to completion. I'm single but not totally out yet so please be discreet. At the same time, I'm a...
Gay Biker in Chicago. Genuine man looking for male life partner Gay Biker in Chicago Seeking M4M Life Partner
Or at least a dating partner for now. No one knows where anything will go but I am into football and sports. I play golf, so if you like golf that is an absolute bonus! I am a proud doggie daddy, love dogs! I also own a motorcycle and love to go out rid...
π³οΈβπMale for Male β Letβs Skip the Small Talk & Get to the Moaning πποΈ We should avoid pretending about our friendship intentions because I am looking for something more. As a 30-year-old man with a fit body I understand my desires which include a dominant confident partner who takes control without hesitation. View My Sexy Gay Profile -
We will hav...
Want to touch my amazing... Wookie? Me, black gay male seeking local men to date, hang with and have some good times. Up for pretty much anything. (love body rubs) 5'10, green/blue eyes, 30 yrs old, well endowed and always ready if you know what I mean. lived in Chicago for most of my life. I am a city worker so a l...
Fit black dude looking for cream of the crop I am Steve, 34 in Chicago. I don't care what color, size or age you are as long as you are legal. No heavy drugs or heavy drinking. Some drinking and 420 is cool with me though. I am just looking for a stand up guy who is kind and thoughtful and likes sex. I am into fitness and riding. Hit me up&nbs...
Blonde man age 29 wanting handsome boyfriend Hi guys!! I'm Marcus, age 29 looking for a handsome boyfriend in Chicago. I am kind and fun-loving, and I love dogs. I have three dogs in our family. 2 shepherds called Alfie and Sirius and a Westie called Scottie. I am totally out with friends and family and comfortable in my own skin. I am into bi...
MALE STUD FOR HOT ACTION - Chicago Area ππ₯π¬ Get Ready for the Fuck of Your Life! π
Hi there! I'm Mason and I'm ready to get down and dirty with you. I am only into top. I love it all - pounding your ass, playing with sex toys, kink play, and watching you gagging on my throbbing dick until my cum explodes in your mouth. ππ¦
I'm a kin...
Join Me for an Episode of The Hung and The Restless! Endowed Chicago Gay Man Seeks Hookup
I'm a gay man living in the Chicago area with 10+ thick inches of uncut restless pleasure. I'm Matt 28 years old, 6'0, 200 pounds, muscular, black hair, brown eyes and take care of myself. I'm top, but can be versatile depending on you. You will find me warm and...
Looking for Mr. Goodbar... Just out, and just out of the Marines, now a college student and 22 years old gay male living in Chicago Looking for experienced well endowed older man to give it to me. I'm 5'11, 180 pounds, blue eyes, brown hair, 7in cut, and in great shape. This is a little awkward, I'm new so be patient with me....
Looking for Kinky, Fun, BDSM Sex at Random Times, Must be Discrete!... S&M for Sissys in Chicago
I am a gay male, bit of a thugish/bear into all sorts of BDSM, Fetish, Kink and some role play. I host and am seeking sissibois, twinks and queens for some extra sensual and painful fun. Your welcome, my pleasure! I have all the tools necessary in my Chicago dungeon to...
King of your heart waiting for you in Chicago Abe, 32, local in the Chicago area, own my own business. I work hard and play hard. I am looking for a gentle guy who is understanding and kind. I love to laugh so you have to be funny. Not all the time, but you need a good sense of humor. Life is too fun to be serious all the time. Message me ...
Lonely young man just out in Chicago I just came out about 6 months ago and I am new to this kind of dating. I am 32 and I have a job. I love music of all kinds and enjoy singing. My name is Trace and if you want to chat you can click my profile @TraceChicago. ...May 17th, 2025
Long and hung Wants night of fun and more Long and hung... Now that I have your attention, my name is Luke! I am a 28 year old Barista and I moved to this area 3 months ago. It's a weird time and I want to meet people I can hang with. I want a guy who will listen, make me laugh and generally be an all round good dude. Not fussy on appearanc...
Irish eyes are smiling in Chicago hey guys, I am Sean, 27, an Irish fella moved over here recently and looking for fun lifestyle and fit guys to hang out with. Go and message me and check out my profile @IrishSean27. ...
Mature man wants to find love in Chicago When I say mature I mean 48. I may be mature in age but my attitude is defintely younger. I look 38 and I act 28. I'm fit and active and don't plan to slow down anytime soon!
My name is Graham and I am established with a home and I work long hours. I am only available on weekends right now but hope...
Gay Body Rubs - Need Sexual Relief? - Yeah, You Need SAL!... Sal here in Chicago to melt your stress away and relieve that pent up sexual tension like no other. I host and offer full amenities and services to my gay clients. All men are welcome as well as couples who need to unwind and spice up the day the right way. I serve gay, bixsexual and bi-cu...
Bi-curious and Want to Try it Out... Hi, I'm Gary, 42 years old, divorced, curious but cautious, well endowed, (I'm told) medium build, 5'10, 180 pounds, ex Navy and need to keep this discreet for now. If you live in Chicago, are patient and know the in's and out's so to speak then I'd like to hear from you.
I don't know why I'v...
Not exactly out yet. Need discreet NSA... Mixed mexican/white male 29yrs, professional divorced with two kids. I am looking to explore my bi-sexual curiousity in the Chicago area with the right man and see if there is anything there. If you can be discreet and are interested then please come see me by clicking here....
Mark, 33 Love country music and driving my truck Hey, the name is Mark and I am a country boy now living in Chicago, age 33, a mechanic and I love to drive my Dodge ram 1500 out on the open roads. Sometimes I take a blanket and a beer and hang out at my favorite lake a few miles from my house in the Chicago area. I am self sufficient and I am want...
Let's Play Cock, Paper, Scissors!... Gay Man Looking for Fun in Chicago
Now that I got your attention. Hi I'm Graham, a gay man here in Chicago and I'm looking for a man who likes to play sexually charged games. I'm 28 years old, black hair, brown eyes, 6'0, well endowed, (8+inches) hispanic, single, love to party, no pets, ...
Caramel Sexophonist Playing your tune Hey guys, my name is Milan. I play the sax and I am mixed background. I probably have a tune you like. You wanna hear me play? View my pics and message me @MellowCaramel.
Within 10 miles: Chicago
Male for male only...
Male Seeking Male β Chicago, IL β Deep Dish & Deeper Desires ππ¦ Chi-Town hunks! I’m a 33-year-old gym bunny with strong thighs, a wicked smile, and a thing for confident men who can take control. I want to meet a dominant top who is familiar with Boystown and the bedroom π View My Gay Dating Profile and Pictures -
You can find me at ...
I am a hot lil sissy living in Chicago - HMU!... Black Sissy Boi in Chicago
Checking this out online, never been at this before. I'm Charles a black male, 155, five foot 5, w long and skinny as you can see in my hot profile pics. Just looking for a little sexy adventure here in the Chicago vicinity. Click here for more of me......
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Proudly sponsored by Chicago Lesbian, Gay, Bisexual & Trans Dating Community
The Trevor Project Donations, by Megan Morrison
BonePage.com proudly supports The Trevor Project, an organization dedicated to suicide prevention among lesbian, gay, bisexual...
Massage genius ready with good hands Thanks for checking my ad. I'm looking for great sex first and foremost but maybe more for the right man. Do you want a nice massage? I am Nico and I can give an amazing massage. If you want to swap pictures and contact info just message me @NicoMassage. ...
F/M seeking love and fun Female to Male Trans Man in Chicago
My name is Karl and I am a F2M trans dude. I was born female but transitioned to male a few years ago. I love my new body. I like dressing sharp with nice suits and taking good care of my hair and my beard. Sometimes it is just scruff and other times I let it gro...
Macho, Macho Man... Are you one of the Village People? I'm a 40 year old macho man looking for bottom man in Chicago. Be ready to be rode hard and deep. I'm 6'2, muscular, hairy, blue eyes, black hair, full 8in, and full of fire. I'm gonna make you tap out boy! I'll pick you up on my Harley and take you for a ride you'...
Artzee Fartzee in Chicago Here for Men and Inspiration!... I'm, Art, (or Arthur) 25 years old, 5'8, 160 pounds, black hair, hazel eyes don't get out much because I'm so into my art, but I'm here to maybe find some inspiration. You never know where it will come from. Could be mind blowing sex with a hot just out gay man. Mmmmm! Bring it on, and hit me like y...