Chicago Men Seeking Men Classifieds

Browse Chicago men seeking men classifieds to meet local gay, bisexual and bi-curious men for sex hookups. Contact any of these men to swap pics and contact info. Chat online or text and arrange real-time sex hookups if you feel a connection. It's free to search all men for men classifieds, or post your own adult ad!

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October 7th, 2026
💙 Unwind With Nico 🌿 I am Nico, a fully qualified massage therapist as well as an experienced companion. Nice, charming, warm and friendly. I do love giving massages, although I'm here for dating and some fun.. I can be just a little bit naughty 😏... Handsome Feel free to message me here - let's connect! ✨ Pr...
The Trevor Project Saves Young LGBTQ+ Lives BonePage Supports The Trevor Project 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...
Tatted Dad Looking For His Boy Around Chicago 35, hairy, brown hair, brown eyes, 5 ft 10, about 7.5 inches cut. Hippie type guy looking for his "boy" to smoke with. Prefer younger guys but can go older for the right guy. Hey, a hot guy is a hot guy, regardless of age. Mostly top here, but very oral and loves to eat a hot ass. Send me a message ...
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......
Irish eyes are smiling in Chicago Hey guys, I am Sean, 27, fit, fun, and freshly landed in town with a cheeky grin. I'm a fun fella, moved here to the Chicago area recently and looking for fun lifestyle and fit guys to hang out with. Go ahead and message me and check out my profile @IrishSean27.  I’m a laid-back gentlema...
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....
Gay Russian Bear New to Chicago... My English is not so good yet. I am Vlad from Moscow, Russia and want to find gay young man for sex in Chicago. I am 34 years old, 6'2, 210 lbs, blue eyes, big size penis, not cut, stay in good shape and love good party.  I am here for 3 years, engineer and single, but still no car. If you are...
💪🍆 I'm All Tha Chocolate You Could Need 💪🍆 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 🍆 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...
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...
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...
💦 Midwest Heat, Let’s Link & Sweat 😈 – Illinois Edition What’s up, Illinois? I’m a laid-back, masculine guy lookin’ to connect with another man who’s down to get into something real, raw, and ridiculously hot.I’m into chemistry, dirty talk, deep kisses, and deeper strokes. Whether you’re curious, experienced, or just i...
🌶️Male Seeking Male – “What Are You Into?” Everything. Now Come Over. 🍑🖤  You have me as your hidden secret while I am your deepest sexual desire which will cause you to  have morning soreness and a pleased expression 😘 I enjoy oral fixation while practicing roleplay and light  dom/sub games with an interest in power dynamics and extended filthy nights ...
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...
MALE STUD FOR HOT ACTION - Chicago Area 😈🔥👬 Get Ready for the Fuck of Your Life! 🍆 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. 🍆💦 I'm a kin...
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...
Fuck Me Like Your Bitch Won't Let You. (Ass Up/ Face Down/ Anon) I'm not looking for small talk. I'll be ass up, face down, and ready for you to fuck my brains out. Looking for someone that knows how to destroy an asshole. 100% anonymous, I don't care to see your face. All I want is a deep hard fucking until you blow your load all over my guts. The deeper and har...
🍻 Fresh Out of a Relationship.. Just Want a Fun Night Username: @RyanOutTonight Private Meetups: YesPhone Chat: YesVideo Chat: YesPics Available: 16 💬I'm ready for a night out😉HMU Hi.. My name is Ryan and I'm from Chicago. Recently come out of a relationship and I'm not looking for anything too serious. I need to get out and about, get some ex...
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...
Chicago Musician wants to funk you up! Gay Musician 4 Fun in Chicago! I'm Gig (real name) living and working here in Chicago. I'm a cross between Little Richard and Prince baby! Not the serious type and love to party. (music, sex, 420 and drinks) I'm always down for some music playin and singing. But, I'm really here for the men. L...
October 6th, 2026
💎 Adorable Sugar Baby 💎 Seeking his Generous King 👑 📍  Location: Chicago    Seeking: A kind/dominant daddy👑  A Little about Me: Hello everyone! I am a sweet, fit blonde with a flirty nature  and an appreciation for the good things in life. I enjoy being pampered, looked after and treated  like a king. If you a...
💦Male for Male – NSFW Only: You Dom, I Submit. Period. 😈🖤  The advertisement is not intended for casual greetings. This is: You top. I bottom. You  take. I give. You tell me what to do. I do it. Simple. Dirty.  Hot. View My Gay Dating Profile Here - ❤️✨ I completely submit to all things kinky while being body-positive and ready to sur...
Small, smooth body big heart Smooth 19 years old in Chicago Hey guys, I am Jon and I am 19 years old, smooth, slight build but fit. I like to do karaoke, dance and travel. I love to explore the male body and enjoy sex anytime, anywhere! I'm a passionate and attentive bottom only plus I can cook a great meal! Check out my profi...
I'm Your Sexy Guy... ALSO BI 🍆💦 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...
Blond Twink Need My Smooth Ass Fucked I am ass up, face down and looking to be fucked anonyumosly. You walk in, slide it in and spill your load deep inside me. All ages and races welcome. Looking to see how many loads I can collect today. I am 19, 5,9 160lbs with a nice smooth bubble butt that needs your attention. Hit me up. FREE Gay ...
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, plz. Not all the time, but you need a good sense of humor. Life is too fun to be serious all the time. Message me ...
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...
🔥 Your Private Indulgence in Chicago 🔥 You can trust me as your hidden secret while I become the constant thoughts that stay in your mind after our time together ends. The special bond between us creates a sensation which makes you move at a reduced pace during your daily activities and causes you to smile for no apparent reason. I enjoy...
Male Seeking Male - Chicago, IL – Deep Dish & Deeper Desires 🍕💦  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 😈 View My Gay Dating Profile and Pictures - You can find me at ...
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 never seem to have time to get out and mingle. I need a friend with benefits! Send me a private message to @WillSciFiFan if you want to swap ...
VirginAss88, Never Been With a Man... I like having fun. I'm very honest perosn, very brave and interilligent. Love it here in Chicago and all the possibilities it offers for a guy like me. don't like the idea of bar pickups and would rather ease into this thing. Must be descreet and honest. Message me here. VirginAss88...
Nerdy Guy Seeking a Cute Dude 🤓💬 A bit of background I'm usually quite pretty much invisible, but I'll be a bit more noticeable once I'm awake. Tech kind of person among a few other things. Self-proclaimed self-styled pop culture geek and obsessive love of cinema and video games. Wide awake at late hours of the night having empty c...
🔥 Your Best Kept Secret in Chicago 🔥 28year old male! The following scenario exists in my mind. Your eyes meet mine when you want to remain hidden yet my presence stays with you throughout the entire day. Your connection with me causes you to slow down during your morning walk while you encounter various joyful experiences. I want to p...
29, Swimmers Build, Looking To Fuck Tonight - Host or Travel Title says it all, looking to host or travel. Looking to fuck all night. I am hung with a 9 inch uncut dick. Verse, but more of a top. But if you have a nice cock, I'd be riding you in a heart beat. More into the vibe of the guy than worried about age or looks. Hit me up and see if we are a match. ...
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 truck 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 wanting to me...
Sexy Sissy Twink Wants to Get Rekt by Power Top Man! Drive it home rough and real hard big boy! I'm Harris a 23 year old twink sissy, Aries, 5'7, 140 pounds, blue eyes dark hair, tight ass who loves alpa type gay men and bisexuals. Please have stamina, strong controlling hands to hold me and help thrust harder. Let me know if you live in the Chicago a...
6'2 Dark Chocolate in Chicago Hey! I'm Gary, age 27, tall, dark, chocolate, want to meet you. Super ready HIV Negative. Come and play in Chicago at Roscoe's Tavern or Dorothy.  Message me @ChocolateRush for my pictures and #...
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...
Need a Sex Buddy! After a long relationship I just want a sex buddy who is good with hooking up and being friends. I'm picky since I don't want to just hookup with any Tom, Dick or Harry. About me: Gay male, attractive, 31 years old, clothing purchaser, 5'10, blue eyes, well endowed, laid back, not much of a temper,...
Athletic Guy Looking for a Fun Gym Buddy 💪🔥 A bit about me: I'm quite healthy and fitness oriented, I love working out. I'm 180cm tall and generally a pretty chilled person. I'd love to meet other men who like living healthy, confident and maybe even looking for similar things as me. Fitness enthusiasts, gym rats, and healthy eaters. I enjoy ...
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...
Leather, BDSM and Bondage Lovers Wanted. Looking to host a BDSM & Bondage sex party. All shapes, sizes, ages and positions needed. I have a house out in the country with a private yard that we can do this in. Looking to arrange an all night sex fetish fest. Contact me if you are interested. FREE Gay Sex Finder Service! We get you LAI...
October 5th, 2026
KINKY KENNY FOR HOT MALE-ON-MALE 😈 Horny Man Wanted in Chicago 😈 I'm Kenny, a horny gay man from Chicago who is on the hunt for some wild and kinky adventures with a local area guy. I love getting down and dirty, exploring all kinds of sexual acts and fetishes. I enjoy giving and receiving blowjobs, rimming, playing with dildos, ...
Jon Boy seeking Chicago Top Male to Pleasure 👅🍆💦 Kink friendly bottom male Hey, thanks for checking my ad. I'm Jon Boy, looking for a hot gay man who's ready to play with me and let me explore all kinds of naughty fun as I pleasure you. Recently out gay male, age 21, seeking other gay, bisexual or bi-curious guys for some wild male-on-male action...
🔥 Manly Vibes & Late Night Energy in Chicago 🔥 I am seeking a self-assured man who resides in Chicago and possesses particular objectives while making active efforts to reach his aspirations. I seek to meet people who have chemistry interests like mine and who desire to create authentic relationships during our evening exploration. I seek to spe...
Verse Hung Blond For Some Nasty Fun Tonight Long blond hair, smooth, about 9 inches cut. Vers guy looking for some fun in Chicago tonight. Very oral, love to deepthroat. LOVES to eat a hot ass! If you are looking for some vanilla sex hit me up. I can host or travel within about 25 miles from me. Hit me up and see if we are a match. Would love...
College Guy Looking For A Fuck Buddy In Chicago Are you near Chicago? I am looking for a fuck buddy to fuck around with from time to time. It would be great if you had a place, or we can do car stuff. I am 20, fit, 165 lbs and 5ft 8. Prefer men under 45, but men can be hot at any age. Love uncut guys, but it's not required. Send me a message and ...
Twink Boi⚡ Not Here for Small Talk in Chicago ⚡ This isn’t casual. It’s clear. You lead. I follow. You take control. I surrender. Simple. Intense. Electric. ❤️✨Your belief in your current role and your search for someone who knows their responsibilities exactly aligns with my own perspective. Message Me here -  Discretion ...
Vers, Masculine, Muscled, Looking For A Good Fucking - Host Or Travel Looking for a someone who wants to meetup on the regular. I can host or travel. You need to be discreet just like I am. I have a high level job and I don't need my personal life out there. Age is not an issue, prefer confident men who know what they want int he bedroom. Vers here and LOVES to suck c...
Black Circus Dick Looking To Top A Fags Hole In Chicago. 12 inch, uncut, black, monster, circus dick looking for a power bottom that knows how to take it long and hard in {CIty}. I like a nice fat ass that I can watch bounce while I go at it all night long. I can host or travel. I'd love to see you bent over my bed as you watch yourself in my mirror as I ...
💎 Ready to Be Spoiled in Chicago? 💎 Hey there handsome… I’m a 25-year-old guy with a strong build, big drive, and an even bigger appetite for fun. I dedicate myself to success while enjoying my comfortable lifestyle because I want to experience these pleasures with someone who appreciates luxury. I enjoy spending time wit...

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