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.

Home / Adult / Male Escorts

Show Ads In: Bloomington-Normal | Carbondale | Champaign-Urbana | Chicago | Decatur | Peoria | Quad Cities, IA/IL | Rockford | Springfield, IL

  • April 20th, 2026
  • 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 ...
  • ๐ŸŒ† ILLINOIS DADDY SERVING DEEP DISH & DEEP STROKES ๐Ÿ†๐Ÿ’ฆ  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...
  • 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....
  • April 19th, 2026
  • 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...
  • FATHER BY DAY - ESCORT BY NIGHTโญ - LET'S HANGOUT TONIGHT ๐Ÿ‘…๐Ÿ† 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 ๐Ÿ˜˜ look at my video as an example ๐Ÿซ  You don't have to be shy, I will take good care of you, I assure. I only answer whatsapp so no emails. Hit me up an...
  • 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...
  • 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...
  • Surrogate Father Services - Need a Fertile Male, or Just a Night You'll Never Forget? I am a male escort serving the Chicago area. My forte is surrogate impregnation of women who need my services. I have great genetic credentials (see more on that later) and I will see the process of impregnation through to completion. Discretion is my upmost concern. Most of my clients are lesbian ...
  • 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 ...
  • HEY DADDY ๐Ÿ˜ˆ GAY ESCORT FOR TRUCKERS IN Chicago ๐Ÿšš 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...
  • 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...
  • 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. ๐Ÿณ๏ธ‍๐ŸŒˆ About Me: ๐ŸŒŸ Handsome and Confident ๐ŸŒด Proud Puerto Rican ๐Ÿ’ƒ Passionate Dancer ๐Ÿ˜˜ Great in Bed!!! I'm on the lookout for se...
  • 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...
  • Smooth Ebony Gentleman Available Tonight ๐Ÿ–ค Marcus Username: @MarcusElite Male Escort: Yes Private Meetups: Yes Phone Chat: Yes Video Chat: Yes Pics Available: 15 ๐Ÿ’ŽSerious inquiries only๐Ÿ’Ž Hello, I am Marcus here in Chicago... Extremely good looking, athletic, and charismatic. The girls I am interested in are women who appreciate a man w...
  • 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...
  • Sexy Gay Male Seeking Hot Guys for Discreet Fun in ๐Ÿ’ช๐Ÿ† Chicago Hey there, I'm Lawton and I'm on the hunt for some sexy guys who are up for some naughty fun ๐Ÿ˜‰. 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...
  • โค๏ธ YOU CALL ME DADDY ๐Ÿ˜ˆ 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! ๐Ÿ’ฆWhite men, black men.. I will...
  • 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...
  • 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...
  • BBC EBONY ๐Ÿ† STUD READY TO PLAY ๐Ÿ† Chicago I'M YOUR NEW BBC LOVE OBSESSION๐Ÿ† 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...
  • ๐ŸงSexy Twink Boy Chicago ๐Ÿง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. ...
  • Athletic Ebony Gentleman โ€“ Bi, Tatted, Open-Minded & Ready to Please ๐Ÿ”ฅ ๐Ÿ’ŽBisexual Ebony Escort (Men or Women)๐Ÿ’Ž Height: 6'1" Weight: 220 lbs Build: Muscular Ink Count: Medium (shoulder to waist) about me: black athletic male looking for a good energy. Good vibes also a must. Respectful men, women and couples always welcome if you're looking for a good time. ...
  • 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 ...
  • 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...
  • 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 ...
  • 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 ...
  • BIG BLACK COCK ๐Ÿ†ย  I KNOW YOU WANT TO PLAY WITH DADDY ๐Ÿ’ฆ   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? ๐Ÿ’ฆI love white men, black men..I love being top and b...
  • 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...
  • 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...
  • 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...
  • 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 ...
  • April 18th, 2026
  • ๐Ÿ†๐Ÿ’ฆ๐Ÿ‘ 9 Inch Thick Power Top Looking To Destroy Your Hole - Discreet๐Ÿ†๐Ÿ’ฆ๐Ÿ‘ FREE Sex Finder Service! We get you LAID, gaurunteed. We do all the hard work for you. Getting laid has never been easier. This Is How It Works: 1. You enter your email. 2. You get a FREE list of men in Chicago who are "down to fuck" right now. 3. You contact these horny men and get laid t...
  • 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...
  • 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...
  • 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!!...
  • 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...
  • I'LL BE YOUR GAY LITTLE LOT๐ŸฆŽ The road doesnโ€™t stopโ€ฆ but you can. HEY DADDY ๐Ÿ˜ 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...
  • 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 ...
  • 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...
  • LEAVING SOON.. Treat Yourself ๐Ÿ’œ Smooth as Whiskey ๐Ÿฅƒ ๐Ÿ˜ˆ ๐Ÿ“Visiting Chicago for a short time — available in surrounding areas๐Ÿ“ new in town. very confident, very clean and very charming. im very down to earth and love to have a chat with people especially the ladies if you are into having a good chat and wanting to have a nice vibe and even a b...
  • 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...
  • 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...
  • ๐Ÿ’ŽThe Best or Nothing.๐Ÿ’Ž28m Escort in Chicago โญ๏ธ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. ๏ฟฝ...
  • KINKY KENNY FOR HOT MALE-ON-MALE ๐Ÿ˜ˆ Horny Man Wanted in Chicago ๐Ÿ˜ˆ 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, ...
  • 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, ...
  • 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...
  • 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...
  • Chicago, IL โ€“ Deep Dish & Deeper Desires ๐Ÿ•๐Ÿ’ฆ  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 ๐Ÿ˜ˆ View My Gay Escort Profile and Pictures - You can find me at &...
  • HOT ESCORT Guy Seeking Hot Male-on-Male Fun ๐Ÿ†๐Ÿ’ฆ๐Ÿ”ฅ 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. ๐Ÿ†๐Ÿ’ฆView My Male Escort Profile Age: 29 years old Name: MOE ๐Ÿ˜ˆ๐Ÿฅต Gender: MALE Location: ...
  • Hung 8โ€ HUNK ๐Ÿ†๐Ÿ’ช guy hosting in Chicago ๐Ÿ† 8" uncut lean muscle, tattoos and lite body hair๐Ÿ’ช๐Ÿผ Athletic and in Shape ๐Ÿ˜‰๐Ÿ”ฅ 70 five-star reviewsโžก๏ธ I love to top and I also love to bottom..โžก๏ธ Open Minded to Anythingโžก๏ธ Discretion guaranteedโžก๏ธ Friendly and fun, always a good timeโžก๏ธ Fully transparent, no games and...