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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February 11th, 2026
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...
I'll give you Sex & the City, Mr. Big Vibes... I'm Jude a professional male escort in Chicago, discrete and aim to please. Your satisfaction is guaranteed in and out of the bedroom. I mix well in any social situation and am well educated. Always ready for intimacy of any kind, even if it's just snuggling. (yeah, I can be a good snuggler too) I ...
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...
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 ...
Gay Man Seeking Tops to Fuck Me Hard in Chicago - Oral Specialist! Fuck my Tight Ass and Cum In Me! Hey studs, I'm Adam, a horny gay man from the Chicago area looking for some hot male-on-male action. I love getting my ass pounded hard and deep, feeling every inch of your throbbing cock moving inside me and feeling your warm load explode deep into my ass. I also e...
James Bond Double wants to take you on a hot date Male for Male Escort in Chicago Hey, I'm Martin. You may call me Marty. I have brown hair, stunning brown eyes, tall, hung and ripped. I want U to be my date. Message or text MartyHungM Kink friendly - Unrushed attention - Top or bottom - Friendly and Fun!!...
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...
KING SHLONG 🍆😈 TRUST MY COCK Get ready to experience Orlando's most relaxing and entertaining Rubdowns 4 men. With 16 very different settings for a relaxing experience, you can choose from traditional candles, Planetarium setting with thousands of moving stars, to the most popular Cinema Experience, where you can see any adult ...
9in Hung Breeder 9" Hung Man for Man in Chicago Nasty As u Want!  Discreet. Always Wild, Fun, Fetish Friendly And Always Erotic. I'll be waiting to please! Men, women or couples. Cucks and fetish welcome. I love all kinds of sex so don't be shy.  Hot Stress free zone. Pictures are real. I've me...
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...
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 ...
PR Gigolo living local. Has time for you. Male Escort for male in Chicago I am from Puerto Rico and I am living local and wish to meet you. I am Henry and I am friendly, sexy and well endowed. I'm easy going and like to have fun. I'm very much sexually adventurous so I can please you much. Check my profile @RicoHenry8. Text or call me...
Exotic and Erotic Escort Orlando From Tuscany Italy... For More Than Just a Hookup Ladies I am Orlando a discreet escort visiting in Chicago. Let me take you on an erotic journey of passion and delight tonight. I know how to treat a woman and bring out the sensual romantic in you. Just let yourself go and forget all about your cares for the evening. Yo...
February 10th, 2026
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....
I'LL BE YOUR GAY LITTLE LOT🦎 The road doesn’t stop… but you can. HEY DADDY 😏 YOU IN Chicago FOR THE NIGHT? Got called lot lizard before haha. Heard it plenty of times like that. Truth is, I do not fit that outdated truck stop mold. A young adult, barely twenty-five, here's who I am - familiar with highways, drawn to city energy after dark, always chasing extr...
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...
🍫 Midwest Chocolate Craving? Come Get Fed 😈 – Chicago Male Escort Tall and strong, the Ebony man walks across Illinois with intent. He does not hunt, he looks for a person who matches his speed. Present matters - no hidden roles behind monitors. Carry confidence? He notices. Bold clothes? Same result. Need honesty? It shows up too. When connections count, sparks g...
BIG BLACK COCK 🍆 I KNOW YOU WANT TO PLAY WITH DADDY 💦   Let's chat right now, share some pix and then talk about hanging out and what we'll do. I want to be dominant and have fun together. I'm a black man and I love sex. I love every type and every type of sex. Whare are you in the mood for? 💦I love white men, black men..I love being top and b...
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...
🌆 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...
HOT ESCORT Guy Seeking Hot Male-on-Male Fun 🍆💦🔥 Are you looking for a wild time with a hot guy from Chicago? Look no further! I'm Waring, and I'm here to fulfill all your deepest desires. From steamy blowjobs to intense anal play, I love it all. 🍆💦View My Male Escort Profile Age: 29 years old Name: MOE 😈🥵 Gender: MALE Location: ...
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...
💎The Best or Nothing.💎28m Escort in Chicago ⭐️I'm into all kinds of kinky fetishes like using dildos, playing with balls, and exploring new ways to make each other cum. Whether you're a top, bottom, or somewhere in between, I'm game for some steamy playtime. Let's get naked, explore our bodies, and have some intense orgasms together. �...
Macho, Macho Man... I'm Bruce and don't mistake me for one of the Village People or I'll have to pound your ass extra hard! I'm a gay male escort serving twinks, fairies and queens in the Chicago Area. I'm 38 years old, 6'2, 220 pounds, Black hair, hairy, 9 thick uncut inches and you are bottom and sub. I am discreet, ...
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...
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...
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!...
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...
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...
Always Bring Bananas to the Party! Hint: They're not for making banana daiquiris! 6'1, white male, blonde well endowed male escort in Chicago who is always ready for any ocassion. I serve men, women, and couples and can attend any special event you may have in mind. I can even cosplay if the event requires it. To book or find out mor...
Erotic Psycho-Thriller...Meet Your New Drug and Addiction! We will explore new and unknown aspects of your sexuality, as well as discovering emotional and subconsious fetishes unbeknownst to you at present. I am a master and architect of perversion and domination, pushing your limits as an ultimate expression of your submission to me - The MASTER! Cur...
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! ...
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...
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...
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...
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, ...
Marco Male for Male Arrangement in Chicago Seeking Hard Male-on-Male Sex in Chicago Hey there, I'm Marco, age 27 from the Chicago area. Looking for a hot gay or bisexual man who can handle my insatiable appetite for sex! Looking for no-strings male on male sex? I'm your guy! I'm seeking other guys who are down for some serious fun. I can go...
February 9th, 2026
💎KiLLAH💎BBC - DTF Hey there, I'm a Bi sexual black man who knows How to please and loves to be pleased.  I promise to give you a Killah time and make you cum! 💦I love white men, black men.. Women... I am to please🎯 Browse My Escort Profile -  Yo, I'm an Ebony Man Who is Biwell hung and read...
Chicago, IL – Deep Dish & Deeper Desires 🍕💦  Chi-Town hunks! I’m a 26-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 Escort Profile and Pictures - You can find me at &...
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...
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...
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!...
Hung 8” HUNK 🍆💪 guy hosting in Chicago 🍆 8" uncut lean muscle, tattoos and lite body hair💪🏼 Athletic and in Shape 😉🔥 70 five-star reviews➡️ I love to top and I also love to bottom..➡️ Open Minded to Anything➡️ Discretion guaranteed➡️ Friendly and fun, always a good time➡️ Fully transparent, no games and...
BBC EBONY 🍆 STUD READY TO PLAY 🍆 Chicago I'M YOUR NEW BBC LOVE OBSESSION🍆 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 o...
🧁Sexy Twink Boy Chicago 🧁YOUR CUTIE ESCORT 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. ...
HEY DADDY 😈 GAY ESCORT FOR TRUCKERS IN Chicago 🚚 Hey daddy, I'm familiar with how gay drivers on long routes often end up here. Solitude during extended trips creates space for cravings beyond entertainment or convenience food. Quiet evenings during journeys can lead someone to seek out connection beyond the usual. Close by, you’ll find truc...
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 ...
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...
Baby Face Hot Dude waiting for the ladies Male for Female Escort in Chicago I am Howie and I am waiting for you. I am 31, hung and fit. I focus entirely on your pleasure and will do what you want. Your satisfaction is my top priority and guaranteed! Message or call @BabyFaceHowie...
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