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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  • April 21st, 2025
  • Male 36 Tall and Handsome EscortMale 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 ...
  • CONTROLLING and SADISTIC GAY BDSM MASTER...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...
  • Upscale Gent Required in ChicagoUpscale 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...
  • Kevin, Male Escort for hireKevin, 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....
  • ❀️ YOU CALL ME DADDY 😈 I❀️ 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! πŸ’¦White men, black men.. I will...
  • Ripped and Sexy Gay Male Escort in Chicago...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...
  • Italian/American Gigolo to make you feel goodItalian/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...
  • πŸ†πŸ’¦πŸ‘ 9 Inch Thick Power Top Looking To Destroy Your Hole - DiscreetπŸ†πŸ’¦πŸ‘πŸ†πŸ’¦πŸ‘ 9 Inch Thick Power Top Looking To Destroy Your Hole - DiscreetπŸ†πŸ’¦πŸ‘ 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...
  • πŸ’Ž Sugarboy πŸ’Ž πŸ‘‘ Let Me Be Your Prince – All I Need is a KingπŸ’Ž Sugarboy πŸ’Ž πŸ‘‘ Let Me Be Your Prince – All I Need is a King  πŸ“ My Location: ChicagoπŸ’Ž I'm Seeking: a Generous & Discreet DaddyπŸ”₯ This is about Me: Hey, I am cute and slim, I have blonde hair and a friendly personality, I also  have a mischievous nature. I'm a bit younger in my 20's and I'm totally finding an older daddy! There is nothing...
  • 20 Year Old Party Boy for Your Cock πŸ˜‹ Chicago20 Year Old Party Boy for Your Cock πŸ˜‹ Chicago Fuck my Tight Ass. Make Me Gag on Your Cock πŸ˜‹ 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...
  • Hung Black Male Chicago for male actionHung 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...
  • Surrogate Father Services - Need a Fertile Male, or Just a Night YouSurrogate 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 ...
  • Hello Ladies, Meet Mr. Goodbar...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 ...
  • Marco Male for Male Arrangement in ChicagoMarco 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...
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  • April 20th, 2025
  • 50 Shades of Gay...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...
  • Jon Boy seeking Chicago Top Male to PleasureJon 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...
  • Bryan for Hot Male-on-Male Action in ChicagoBryan 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...
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  • Exotic Gay Latino Visiting Chicago from Brazil...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...
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  • College Grad studying for MastersCollege 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!...
  • EBONY Gay Male Encounters With Discretion in Chicago Tonight!...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...
  • Sexy Chicago Guy Looking for Hot Male-on-Male FunSexy 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. ...
  • Throbbing Cock Needs Tight Ass to Ride in ChicagoThrobbing 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...
  • Chicago πŸ†BBC KingπŸ† – You Know What It IsChicago πŸ†BBC KingπŸ† – 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...
  • HIRE THIS BIG DICK FOR THE NIGHT ;) - ChicagoHIRE 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...
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  • Male Escort, Hot Body will please youMale 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...
  • Macho, Macho Man... 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, ...
  • Baby faced 30 year old escortBaby 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...
  • II'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...
  • PR Gigolo living local. Has time for you.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...
  • Best thing you never had with a big surprise!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! ...
  • Sexy Sissy Twink Escort Wants to Get Rekt by Power Top Man!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 ...
  • Gaymer Guy seeks M4M Arrangement in ChicagoGaymer 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...
  • April 19th, 2025
  • Chocolate Thunder Gay Male Escort in Chicago...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...
  • Tall Dark handsome long hair and long everywhere 31Tall 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...
  • II'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 ...
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  • 9in Hung Breeder9in 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...
  • Big hands can massage your tired bodyBig 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...
  • MALE ESCORT - Chicago - READY TO FUCK!!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 ...
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  • Always Bring Bananas to the Party!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...
  • Hot and Sexy Male to take you to the moonHot 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...
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