Chicago Male Escorts Sex Classifieds

Browse Chicago male escorts listings of providers to find male escorts and independent sex arrangements near you. Due to U.S. regulations, prostitution ads are illegal and thus are not allowed. All ads in BonePage male escort ads are for legal escort services or adult companionship arrangements. Any sex that may occur is strictly by mutual consent between adults, and of their own free will.

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November 26th, 2025
CONTROLLING and SADISTIC GAY BDSM MASTER... Gay BDSM Escort in Chicago! Meet your dominant, uber controlling, nuanced and deviant Master Rex male escort in Chicago. Combining sensuality, eroticism and fantasy in his well appointed private pleasuredrome. I provide primal experiences that awaken the instincts, disolve the self, and give me ful...
Chicago 🍆BBC King🍆 – You Know What It Is Sexy & Muscular Ebony Escort in Chicago = your pleasure Firstly, I would like to welcome ,I cater for those that seek exclusive quality, if that’s you: you’ve found your dream man. I take my body seriously, being atheletic is always a priority which will be obvious when you explore m...
Hot Gay Male Escort of The Asian Persuasion! I'm Tuvan of Korean heritage originally from Seoul, South Korea and new here to Chicago. I have training in the sexual arts and possess many skills rarely seen in the Western World. I am sub, bottom, 5'6, 25 years of age, highly trained, professional, discreet and love American gay men.  I do ...
You Can't Put a Price on Pleasure,,, and I Bring it!... You're gonna get a lot of bang for your buck with this young hung bi-stud who is always ready. Just when you think I can't possibly go again, I'm up for the challenge. Chicago is my home and travel is OK within 50 miles or so. Let's get together tonight!...
Spanish Gigolo for hire M4M Male Escort Now in Chicago "¡Hola! I'm Juan Carlo, age 28, handsome, a charismatic and outgoing gay Puerto Rican man with a zest for life. 🏳️&zwj;🌈 About Me: 🌟 Handsome and Confident 🌴 Proud Puerto Rican 💃 Passionate Dancer 😘 Great in Bed!!! I'm on the lookout for se...
Upscale apartment with all facilities. I can please you here or at your home. [Male for Male] Bradley M4M Escort in Chicago Area Hey guys, M4M escort in the Chicago area. I am Bradley, 31, fit, European by birth and waiting for you to call me so I can show you a great time. Tall and well hung. View my online profile and message me BradleyKM4M. Send your photo for mine.   No ...
🌆 ILLINOIS DADDY SERVING DEEP DISH & DEEP STROKES 🍆💦  I am from Chicago and I am fighting for the entire state of Illinois—I am your dominant,  well-hung Black Daddy who does not play when it comes to laying pipe and dealing with boys who  need it deep, raw, and real. View My Escort Profile Here - I am all about control, pressur...
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, ...
MALE ESCORT - Chicago - READY TO FUCK!! Are you looking for a hot and horny guy to fulfill all your wildest fantasies? Well, look no further because I'm here to make all your dreams come true. My name is Bill and I'm a sexy stud from Chicago who loves to get down and dirty with other guys. My Pics & Info - My Male EscortI'm into ...
Ripped and Sexy Gay Male Escort in Chicago... Top dominant gay male escort muscle man in Chicagoland to fill every hole with my extra large member, and pound your ass into submission! I got the tools, skills, stamina and the drive to make you see stars baby! Book with me for a sexual encounter you'll NEVER forget! I am a professional independen...
❤️ YOU CALL ME DADDY 😈 I'll Teach you my ways   Hey there, I'm a Bi sexual ebony man who knows How to fuck and will give it to you just like the good boy you are. You will beg me for more and more. I also like to take and be pleasued, so don't be shy baby boy.  I promise to stretch you out real good! 💦White men, black men.. I will...
Sexy Sissy Twink Escort Wants to Get Rekt by Power Top Man! Drive it home rough and real hard big boy! I'm Harris a 22 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 Chicago, are ...
Sexy Gay Male Seeking Hot Guys for Discreet Fun in 💪🍆 Chicago Hey there, I'm Lawton and I'm on the hunt for some sexy guys who are up for some naughty fun 😉. I'm a gay man who loves to explore all kinds of kinky fetishes and sexual acts. From deepthroating a throbbing cock to riding a huge dildo, I'm down for it all. Whether you're into being a top or botto...
EBONY Gay Male Encounters With Discretion in Chicago Tonight!... I am gay, black male escort serving the Chicago region. I can accomodate any type of need you might have for an exciting encounter of the ebony kind. Me: Clean, Independent male escort, 6'0, 30 years old, black, 9" + uncut, always ready for action, I do in calls, out calls, travel and am party/420 f...
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...
Chicagoland Male Escort - Best in the Mid West! Hi ladies I'm Carl 28 years of age, 6'1, 200 pounds, take good care of myself, professional, discreet, serving the Chicago area and well endowed. You'll find that I'm comfortable to be around, engaging, upbeat and have a certain sexual vibe.  I am open to women or couples, events, travel, part...
Brandon the Stud Brandon Male Escort in Chicago Hey guys. I'm Brandon. I enjoy dancing, erotic stripping, lap dances and I know how to make you feel good all over.  Hi there! I'm Brandon @BrandonStud and I believe life is meant for dancing with someone special. I'm a gay man who's passionate about dance, and ...
Big, Bold, and Ready to Please 😈🍆 Come Play with Daddy You have been desiring a BBC, haven’t you? That **thick dick, strong, and  commanding presence** that can tell what you need and give it to you. I am  **dominant, experienced, and willing to make you feel as if I am inside of you.** I do  know how to satisfy you, no ma...
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...
JOIN US TO DECRIMINALIZE SEX WORK Decriminalize Sex Work Decriminalize Sex Work by Sienna Mitchell, BonePage.com Staff ReporterThis article sponsored by BonePage Chicago M4M Sex Profiles BonePage supports the movement to decriminalize sex work around the world. The unfortunate reality is that male escorts and other sex workers oft...
20 Year Old Party Boy for Your Cock 😋 Chicago Fuck my Tight Ass. Make Me Gag on Your Cock 😋 Hi, I'm Chuck. I'm a horny gay guy from a conservative family background looking to make up for lost time with some hot male-on-male action in the Chicago area. I love getting my ass pounded hard and deep, feeling your throbbing cock slide in and out...
November 25th, 2025
Michael 42, 5' 11 for Male Companionship in Chicago Male for Male Companionship in Chicago Not your usual male for male companion. Hey guys, I am Mike. I'm 42 and I am great at what I do. If you want me to prove it cum and message me @Mike42m4m. Age play, kinks, 420, alcohol ok. No STDs, clean. I'm discreet and attentive to your needs. I'm easy goin...
Tony, 39, Local, hung, tall and fit for woman Chicago Male Escort for Woman Hi ladies. I'm Tony, male escort for woman in the Chicago area. I ride a Harley and I can take you for a ride on it. Or we can enjoy an evening on the town. I enjoy a wide variety of activities from the opera to sports events. View my profile online @TonyHarleyRoa...
HIRE THIS BIG DICK FOR THE NIGHT ;) - Chicago Hey there, I'm Dave and I'm looking for some sexy guys in Chicago who are up for some discreet and kinky fun. I'm a gay man who loves to play with other gay, bisexual, or bi-curious guys. I enjoy giving and receiving blowjobs, getting my ass played with, and exploring all kinds of fetishes. From rid...
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...
Exotic Gay Latino Visiting Chicago from Brazil... I am Emelio a fetish friendly gay male escort serving Chicago GAY MEN who have good taste and appreciate classy companionship and erotic intimacy that will satisfy your wildest fantasies. What is your kink? I am open to anything and find fetish to be addicting. You can be certain that I am always p...
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Baby faced 30 year old escort M4M in Chicago I am funny and intelligent and well versed in man subjects. If you like to talk I like to listen. I enjoy good conversation and fine wine. If you would like to have the pleasure of my company for an evening we can do whatever you want. Check out my pics and contact info @alexp30X. U...
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Tall Dark handsome long hair and long everywhere 31 Black Male Escort M4M in Chicago I am Dajuan, age 31 black male, and I am tall and long. I am from Jamaica and I am here in Chicago looking for men who want a hot, sexy date. Private message or text me JamaicanHeatXXX...
Hello Ladies, Meet Mr. Goodbar... Let me get that G-spot for you! Young male escort in the Chicago area, extra large and skilled. 10 plus real inches, thick, and cut with stamina to spare. Ever been with a man this big? Want to know what it feels like inside you? Don't worry, we will take it slow if you want to ease into it, try it ...
Throbbing Cock Needs Tight Ass to Ride in Chicago Horny 26 Y/O for Male-on-Male Action in Chicago Hey Guys! I'm Walker, age 26 from the Chicago area. Are you a horny gay or bisesexual guy looking for some wild male-on-male action? Well, look no further because I'm here here to explore all your dirty desires. I love getting my dick sucked and givin...
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Edward, 42 Ready to take you out on the town Edward Booking in Chicago Good day, Ladies. I am intelligent, a good conversationalist and versed on many topics, as well as fully fit and able to offer a night of passion and pleasure while you let your cares melt away and you give way to sexual fulfillment. Open minded and kink friendly. I apprec...
Sexy Chicago Guy Looking for Hot Male-on-Male Fun Hey there, I'm a horny guy from Chicago named Kristian who is seeking other gay, bisexual or bi-curious guys for some steamy action. I love to suck cock, get my ass pounded, and explore all sorts of kinky fetishes. Whether you're into a sloppy blowjob or a tight anal ride, I'm game for it all. ...
I'm a hot sissy in Chicago - I'mma blow your mind! Discreet Gay Hookups I'm Cal a gay White male escort living here in the Chicago area seeking strong thugish gay or bisexual men. Give it to me all night rough, deep, hard and intense. I'll give it that way too, and I love to suck, anytime anywhere. Please gay men only. Don't care for on the fence t...
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50 Shades of Gay... Chicago Gay BDSM Master I'm your Master Bruce taking on new slaves in Chicago. I am an intense dominant controlling type who will break you down and make you my little loyal bitch boi. Humiliation, sissy training, bondage and corporal punishment is my stock in trade which you so desperately need! I...
LATIN STUD READY TO PLAY 😘 Chicago I love giving and receiving blowjobs, getting my ass played with, and experimenting with different fetishes. From sloppy deepthroating to riding a huge dildo, I'm open to trying new things and making our time together unforgettable. Let's get naked, explore each other's bodies, and have some mind-bl...
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...
Chocolate Thunder Gay Male Escort in Chicago... Hi I'm Andre chocolate thunder from down under. I am originally from Australia, and have lived here for about 5 years. I'm a gay Black male escort serving gay, bisexual and bi-curious men in the Chicago area. Will travel, incall, outcall and attend functions, and events. I am 420 friendly and always...
Best thing you never had with a big surprise! I am a very sensual mature gentleman who takes good care of himself. I can fit into any situation and my hours are flexible. I serve the Chicago area and am open minded. Couples welcome, bi- curious welcome. Click here to message me anytime! ...
College Grad studying for Masters Hey, gals, I am Simon. I am 25 and I have been studying for my Masters in fine art. I am currently studying online but was in Italy for a year. I am looking for extra cash to keep my expenses lower, so if you like my profile (and I know you will!) give me a call!...
Male for Male Escort in Chicago. 29. 6' 2 Male for Male in Chicago Hey, I'm Jeff. Will visit you or you can visit me 29. 6' 2. I'm working my way through college but I manage some free time. Need to spend time with men. I love the male form and appreciate all types of men and all body types. Message @JeffOralExpert for a get toge...
November 24th, 2025
Kevin, Male Escort for hire Male Escort for Hire in Chicago Hey, ladies, I am here to take you out to dinner, show you a great evening and spend quality time with you. Would love to see you! See my profile and contact info @KevinAtYourService....
The Trevor Project Saves Young 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...
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