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 21st, 2026
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...
💎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. �...
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...
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...
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...
February 20th, 2026
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...
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...
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...
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 ...
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...
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...
❤️ 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...
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....
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...
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 ...
🌆 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...
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 ...
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...
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...
💎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...
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...
February 19th, 2026
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...
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 ...
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...
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...
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...
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...
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, ...
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...
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 ...
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 ...
February 18th, 2026
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, ...
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...
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...

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