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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March 4th, 2025

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...

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, ...

💪 2 Sexy Masculine Studs - 2 for 1 💪 YOU WANT 2 MALE ESCORTS AT THE SAME TIME?iMAGINE ALL THE KINKY ROLE PLAYS  😉 😍 176 FIVE - ⭐️STAR reviews 💬 Text for the fastest response.🔷 Muscular, masculine, FIT.🔷 Strong hands, big smile, & nice cocks!! 💪 Gym active five days a week.🔷 Approachable, easy-go...

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...

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...

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!...

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...

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. ...

💎KiLLAH💎BBC - DTF Yo, I'm an Ebony Man Who is Biwell hung and ready to please.🍆  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 ...

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! ...

March 3rd, 2025

Italian Stallion ready to give you a special evening Italian Man for Male Companionship in Chicago Area Long, hung Italian stallion with great tongue. You want pleasing? I can please! Message @Mario4malefun and have the night of your life. I'm young, virile and hung. I've got what you want! Sugar Daddy arrangement possible.  Clean, easy-go...

Professional Cuckhold Bull Serving Straight and Gay Couples in Chicago... Hello cuck fans and practitioners in Chicago. I'm Curtis a bisexual male bull escort specializing in cuckhold encounters. Def. top, professional, very clean, respectful, 10 inches thick and uncut. I'm 30 years old, in great shape, lots of stamina and endurance, brown hair, blue eyes and know how to ...

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...

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 ...

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...

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...

TOP ONLY🍆XXL -- ❤️❤️ I'LL BE YOUR VALNTINES ;) MALE ESCORT READYFOR SEX NOW! 😍😍SPANISH XXL❤️🍆Chicago TOP ONLY Sexy & Muscular M4M 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 bod...

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 ...

HIRE THIS BIG DICK FOR THE NIGHT ;) - Chicago Sexy Chicago Guy Seeking Hot Male-on-Male Fun 💦🍆👅 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 as...

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...

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, ...

Hot and Sexy Male to take you to the moon Male for Woman Companion in Chicago I can send you soaring to heights you never went to before. I am able and fit and ready to pleasure you however you please! Please message Jeremy in Chicago to book a date. I will send you a selfie along with my mobile number.  Excellent Prices Open-Mind...

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...

YOUR PERSONAL MALE PORN⭐ - LET'S HANGOUT TONIGHT 👅🍆 HOT GUY IN Chicago READY TO BE YOUR ESCORT - MEN, WOMEN OR BOTH AT THE SAME TIME ;) I can be dominant or submissive, vanilla or violent BDSM, long forplay or directly sex ? So tell me what you need, I'm down for a group sex too 😘 look at my video as an example 🫠 You don't have to be in A...

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...

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...

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...

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...

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!...

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 ...

Upscale Gent Required in Chicago Male college stud for upscale gentleman in Chicago Hey, I am in college right now and I have to pay for everything.  I ain't rich but I am a stud. I only do top, so if you are into that kind of thing let me know. Let's chat a little first and get to know each other. Private message me! Userna...

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...

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...

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...

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!!...

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...

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...

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. 🏳️‍🌈 About Me: 🌟 Handsome and Confident 🌴 Proud Puerto Rican 💃 Passionate Dancer 😘 Great in Bed!!! I'm on the lookout for se...

March 2nd, 2025

Sexy Gay Male Seeking Hot Guys for Discreet Fun in 💪🍆 Chicago ready to fuck right now 😘😉 I'm your guy  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...

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...

HOT ESCORT Guy Seeking Hot Male-on-Male Fun 🍆💦🔥 Sexy Chicago 🍆👨‍❤️‍👨 Guy Seeking Hot Male-on-Male Fun View My Male Escort ProfileAre 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 ...

Cute and Sexy Twink Escort Heating Up Chicago Nights!... Hi all, I'm Tad an erotic dirty minded little twink escort serving the Chicago area. I'm fetish friendly, 24 years old, 5'7, 140 pounds, blue eyes, blonde hair and have the skill to thrill. Incall, outcall, parties, events, travel, roleplay and more.  Let me make your fantasy come true tonight...

Simon the Escort. Call for a night of joy - Men or Couples! Male Escort in Chicago Call me to book ahead for your dream night. Male for male or couples. I am Simon and I can whatever you want to do. Message me online for special price for first timers. View my online profile and drop a message for my private pics. Member: SimonSaysXxX Location: Chi...

Male Escort, Hot Body will please you Male Escort for Woman in Chicago I am Gregory and I am 28, handsome, buff and able to please you. I will take you to dinner and wine and dine you and more. I'm also available for travel. Message me @HotBodMale for my current photos and contact info.  Experience passion and ultimate sexua...

Male 36 Tall and Handsome Escort Male Escort for Women in Chicago Would you like to have a handsome man on your arm to take you to the theater or movies? How about a special night out for dinner, dressed up in a beaufitul outfit? I am a male escort working through college and enjoy meeting ladies who are fun and friendly. Message ...

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....

Hung 8” HUNK 🍆💪 guy hosting in Chicago Stud Looking for Hot Hookups and Discreet Fun Always have a good time, always READY for you 🥰tougher than the rest, allow me to show you FUN!📲 Message me through RM ✉️ or text me (number in bio)🍆 8" uncut lean muscle, tattoos and lite body hair💪🏼 Athletic and in Shape 😉�...

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...

Male Escort, I'm a Small, Submissive Sissy For You😉💦 I need a nice big man to control me and use me - Chicago✅  View More of My Pix and Profile 5 foot 7 tiny BF for you to throw around and control🌴👑 I Model locally and do adult acting 🎥📸 VIP Dancer available for private parties 💵🕺Escort avilable for dates, hosting in and out...

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 ...