Chicago Men Seeking Men Classifieds

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November 11th, 2025
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...
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, ...
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...
🌶️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 ...
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...
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 #...
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...
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...
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...
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......
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...
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 ...
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...
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...
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'...
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....
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...
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...
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...
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...
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....
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 ...
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...
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...
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...
Mature Wealthy Man Looking for Twink Boy Toy... Hello boys I'm Tony 48 years old and been out for 10 years now and take good care of myself. I'm from Cleveland originally, but moved to Chicago to start over again after my divorce. I don't really have any baggage with the kids being grown up and off to college. I plan to retire very soon and want ...
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...
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...
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, ...
November 10th, 2025
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 ...
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...
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 ...
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...
🔥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 ...
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...
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...
🍫 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...
SUGAR DADDY 🍭👨‍🦰 💦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 🤑 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...
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 ...
THICK AND HARD🍆✅right now Hi Guys 😉 I'm Super Horny Tonight I'm in Chicago and willing to travel    My Pix and Profile    COCK SIZE -7INCHAge: 29 years oldName: LEXX 😈🥵Gender: MALELocation: Chicago Availability: Incall & Outcall The Kind of Stuff I Want: ...
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 ...
November 9th, 2025
🏳️‍🌈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...
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...
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...
💎 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...
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. ...
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...
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 ...
Frisky Bottom Daddy Looking To Be Plowed Looking to have my ass streached by a guy that knows how to destroy a hole. Prefer men that are aggressive and wants to take his aggrevation out on my ass. Trying to be your sex slave for the night. 5ft 9, 150lbs, 35yo. Pics posted. Hit me up. FREE Gay Sex Finder Service! We get you LAID, gaurunte...

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