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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September 29th, 2026
💯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...
💦 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...
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,...
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......
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 #...
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....
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...
September 28th, 2026
Asian Twink for Big Hairy Bears... Bottom Asian Twink wants to have hot encounter with big hairy bear tonight! I am new to Chicago and work in marketing for a large real estate firm. I don't get out much and would like to meet the man of my dreams and have wild sexy nights. I'm 24 years old, Asian gay male, hairless, tight ass, lots ...
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....
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...
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 ...
🔥 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...
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...
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...
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...
Black man, 31 needs good boyfriend Black Daddy in Chicago area Man, I don't know what I am supposed to say here lol....I am Frank and I am 31, clean, fit and single. I am just recently out of a long term relationship with my ex boyfriend. I won't go into detail but we just drifted apart. Anyway, I'm ready to mingle! Locals only in t...
💦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...
💎 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...
Nature Boy Seeks Hot Natural Man... I am Ira and love being out in nature when weather permits. I'm looking for a natural gay man (such as a bear or thug) who by his nature will take me and have his way without restraint. I'm a gay twink 22 years old and love to be ravished by force by a strong man. If you live in Chicago and fit this...
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 ...
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 ...
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. This feels right and 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 oth...
I BREAK TWINKS and turn them into MY SEX PUPPETS! Big top bone thug gonna wreck you and make you twinks tap out! Looking for sissie boi to use and abuse here in the Chicago area. All is fair and shit as they say. Needless to say I'm the dominant and controlling type in any situation. Your gonna get the big one rough and deep honey! No screamers ple...
💪🍆 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...
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...
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...
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...
Chill Bearded Guy Seeking a Cool Dude 🍻😉 I'm quite relaxed and very easy going, quite funny and have a beard! I work Monday to Friday and I'm looking to meet new people. I'd like to see where things go. Let's chat and see what we can come up with!  I suppose I just like more assertive guys but not in an obnoxious way. Like someone wh...
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...
September 27th, 2026
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...
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 @St...
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...
🔥 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...
Alex's Huge Throbbing Cock in Chicago 💦💦 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...
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...
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...
🏳️‍🌈Male for Male – Let’s Skip the Small Talk & Get to the Moaning 😈🛏️  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...
🍫 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...
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. ...
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...
🔥 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...
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, ...
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...
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 ...
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 ...
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...
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 ...

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