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!

Home / Dating / Men > Men

<<<

August 11th, 2026
Curious Married Guy Seeking Discreet Connection 🤫🌙 That is the truth, the whole truth and nothing but the truth. I am married and I have had over the last few years sexual feelings towards other men. Discretion is therefore paramount. Therefore I would be looking to chat to someone who understands my position fully and would not in any way attempt t...
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...
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...
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 #...
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...
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...
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...
Tall Dark handsome long hair and long everywhere 31 Black Male for M4M in Chicago I am Dajuan, age 31 black male, and I am tall and long as in exceptionally well endowed. You may be shocked but you will not be disappointed. I am from Jamaica and I am here in Chicago looking for men who want a hot, sexy date. I'm clean, disease free, no addictions, a...
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, ...
🍫 Midwest Chocolate Craving? Come Get Fed 😈 – Illinois Edition I am a tall, strong, and sexy Ebony man living in Illinois who is looking for a real one to match my energy. I am the one you have been waiting for whether you are masc, curious or just ready to experience this deep stroke life. I am all about good vibes, dirty fun, and unforgettable nights. No stre...
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...
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...
James is My Name and F#cking Your Brains Out is My Game! Don't underestimate this Italian/Lebanese twink from Queens. Well endowed top boy (and bottom) will make you tap out and take you to the limit tonight or any other night! I got the endurance to back up my claim and a whole lot of tricks up my sleeve for the right guy. I prefer older bears, but if yo...
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 ...
August 10th, 2026
Henry your Puerto Rican Stud for Local Man Puerto Rican male for male in Chicago I am Henry, from Puerto Rico and I am living local and wish to meet you. I am friendly, sexy with a big dick that is sure to please. I'm easy going and like to have fun. I'm very much sexually adventurous so I can please you much. Check my profile @RicoHen...
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...
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...
I Need an Interesting Man in Chicago... An active imaginative and educated mind stimulates me. I'm Howie, 37 yrs, 5'11, 180 pounds, shaved head, not so attractive, keep to myself a lot, accountant and lover of all things novel and interesting. The world is full of so many fascinating things that I want to soak it all up. If you feel this ...
Confess Your Naughty Kinks to Me! Dirty minded twink 21 years old, well endowed, 5'9, 160 pounds, blue eyes and just out of the closet loves to hear about and play out kinks of all kinds. Blow my mind with your hottest fetish! Better yet let's get together if the mood strikes and fulfill yours and my fantasies. If you live in the Ch...
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...
I'm Troy in Chicago - Bi-Curious Looking to Experiment... Bi-curious in Chicago Hi guys, I'm Troy here in Chicago divorced after 10 years and am entertaining the idea that I might like the gay lifestyle. So, here I am on this site looking for a special kind of man who isn't going to go too fast with me. (is patient) Woman say I'm well hung, but ...
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...
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...
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...
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...
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...
💎 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...
August 9th, 2026
Ebony Street King Looking for a Real One 🖤🔥 About me Confident Black Man with street edge look. My friends say that initially everyone notices my looks and all that because of my height, muscles and deep voice but when you actually speak to me, you soon see that there is so much more to me. Friendly, open and the most honest person you could ...
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....
💯REAL💯HANDSOME💯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 partying✨ and having group sex. Do you like to take it or give it? I will give you something to suck on alri...
🍻 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...
Hung Black Male Chicago for male action Wants hot male for male sex in Chicago. All races welcome. Want some hot male-on-male action? Well, look no further because DeAndre is here to satisfy all your dirty desires. Private message me @DeAndreXXX24. I love hot dates with hot guys, any race. Pretty much top because I prefer being in charge...
🔥Gay Hookups – Bedroom Eyes & No Bullsh*t Vibes 💋🍆  Your mama warned you about me yet your dad would secretly appreciate my nature 😈 34,  toned, tattooed, and nasty in the best way possible. I seek a genuine male partner who  understands my body type through strong hand usage and dominant presence and filthy sexual thoughts. Your ...
August 8th, 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...
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 @St...

<<<