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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December 23rd, 2025
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...
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...
YOUR PERSONAL MALE PORN⭐ - LET'S HANGOUT TONIGHT 👅🍆 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 Amstedam, the cities close enough to it is also fine. I only answer whatsapp so no emails. ...
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...
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...
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...
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 ...
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...
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...
Gaymer Guy seeks M4M Arrangement in Chicago 24 y/o Fit Male Will Spoil Your Cock Hey, I'm Darrel, age 24, fit, very well hung, clean and always down for a fun time. Disease-free, HIV negative. Kink, 420 and gaming friendly! I'm seeking gay, bisexual or bi-curious guys who are ready to get down and dirty with me. You can find me in the M4M pr...
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: ...
Big hands can massage your tired body Ladies, I am Giovani and I am a trained masseur who can take the extra steps to make you feel so good. I can relax you and speak to you in fluent Italian. How about you message me (GiovaniMasseur) and book an evening with me? Mention this ad for a special rate. I am waiting and available in Chi...
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...
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...
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 ...
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...
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...
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...
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...
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 ...
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...
I'm a Mix of Tom, Dick and Harry... I'm Tom and I'm hairy, and I'm a professional male escort living in the Chicago area. I'm 34 years old, blonde haired, blue eyed, muscular, 6'1, well hung (9in + thick) and am fetish friendly when needed. Experience the unforgettable and best erotic encounter of your life. Satisfaction is guaranteed...
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...
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 ...
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...
December 22nd, 2025
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...
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...
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! ...
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, ...
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!...
🌆 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...
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!...
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...
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...
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...
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...
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...
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. ...
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...
Male Escort, I'm a Small, Submissive Sissy For You😉💦 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 calls ✈🌎 Inquire within 😈🥂 I'm a walking daydream that could make you scream and cr...
Italian/American Gigolo to make you feel good Italian Stud for Woman in Chicago Hi, I'm Alex, an Italian man, age 34, in Chicago. Italians really are the best lovers and we know what to do to please our ladies. I am an independent escort who can serenade you, cook you a beautiful meal in your own kitchen and spend the evening with you until yo...
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 ...
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...
December 21st, 2025
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 ...
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 ...
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...
8 inch, 6 feet, ripped and brown has pleasure for you M4M Male for Male Escort in Chicago Hello guys! My name Frank and I am available for companionship locally. View my online profile @FrankM4M8 for my pics and contact info.  I'm chill and 420 friendly. No hard drugs. I'm 6 ft tall, thick 8 inches where it counts. Kink friendly and open minded....
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...
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...
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