Chicago Men Seeking Men Classifieds
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April 7th, 2025
Bear looking for shaved dude My name is Freddy (FrEEkXX) and I am looking for a guy to love. He has to be shaved because I like the feel of my beard on bare skin. Drop me a text or email @FrEEkXX if you want to hang out. ...
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...
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...
Asian gay guy out for love Asian Gay Male for Male in Chicago
Asian guy out to everyone and want to find a nice guy. I am pre-med at the moment and working on Internship. Love movies and video games. Are you a nice gay or bisexual man? Let's chat and see how things go.
Wanna hang out? Name is @TanDude4M, let's trade p...
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...
Hi Guys, I am looking for someone to hang out with in the Chicago area I am 42 and I am into basketball and golf. Love eating out and going to concerts when I can and I want to meet someone who can be my soul mate. Check out my profile.
If you're not Mr Right, you might be Mr Right Now! Let's swap pictures, meet up for lunch or drinks and see where this goes! ...
Hot Muscle dude movie fan Hey, it's Jeff. I am tall and I real fit. I do weights. I am nuts about movies so you gotta be into watching anything. give me a shout. "JeffBuff9"...
31 Years Old in Chicago, Sugar Daddy Arrangement!! Seeks a Sugar Daddy Arrangment in Chicago
I don't care so much about your age but you must be fit and healthy and able to swim and snorkel! I love anything in the water and usually maintain a tan! I am active, fun loving and they say I am attractive! My name is Phillip and I am 31 and I have a dema...
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...
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...
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 ...
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...
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...
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 ...
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...
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. ...
Black man, 41 needs good boyfriend Black Daddy
Man, I don't know what I am supposed to say here lol....I am Frank and I am 41 and 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!
I need some fun and some light hearted dating with ...
Local guy waiting for handsome prince Steve, 21, willing to travel but only within 75 miles or so from Chicago. Working from home right now and just my dog for company I want to meet a real nice dude.
Send me a message to @Steve21SeeksMatureMan.
View my pictures online, send your pics and I'll send my private pics. Let's te...
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...
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'...
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...
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....
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...
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...
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. ...April 6th, 2025
New in Town- Male Masseur NSA Gay Masseur New in Chicago
Hi guys! I give amazing massages. Want to date? I am Tommy and I am 29, tall, and long and thick π clean and HIV neg. Message me for my photos and contact info. Let's make this happen!
@GayMasseurChicago...
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...
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 ...
Gay Lawyer seeks Male Soul Mate Hello, I am a 38 year old lawyer in Chicago looking for a handsome and intelligent man to share weekend fun and outings with. I am reasonably handsome, but that is all about perspective. I am tall and have short brown hair. I like to dress nicely. I enjoy coffee, great conversations, travel, sports ...
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,...
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...
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, ...
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 ...
Mahogany Woody all yours Well hung, muscular and fit 33 y/o mahogany man. Will consider anything as long as you are a sensual lover. Message me to swap pics and meet up. @MahoganyWoody
Username: @MahoganyWoody
Location: Chicago
Age: 33
Text: Yes
Photos: Yes
Available to travel: No
...
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. ...
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...
Newly out bear looking for hairy dude Gay Bear for Hairy Dude in Chicago
Hey, my name is Pascal and I am newly out. I am 26 and I have a very hairy chest, and because it's dark it looks really thick. I have also been cultivating my beautiful beard for 6 years. I like hairy dudes, so if you want to chat and see where it goes just shoot ...
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....
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...
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...
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...
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...
Country Boy Male for Male Country Boy Male for Male in Chicago
I am a regular cowboy hat wearing, guitar playing dude who wants to meet a guy who is authentic and down to earth. I am into fishing and horse riding and I love baseball and beer. I'm a good ol' country boy who likes the company of a nice man.
Come and say hi a...
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...
Chocolate skin man in search of partner Hey guys. I am Frank and I stand about 6'3" but I'm very shy. I've only had a few male dates so if you want to get to know me a little let's chat online @FrankChicago to swap pics and arrange a hookup.
Member Name: @FrankChicago
Age: 34
Location: Chicago
Photos: 12
Verified: 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.
Message me now @ChocolateRush for my pictures and #...
KINKY KENNY FOR HOT MALE-ON-MALE π Horny Man Wanted in Chicago π
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 π
ππ¦ 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...April 5th, 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...