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

>>>

September 7th, 2025
💪 2 Sexy and Fit - 2 for 1 💪 176 FIVE - ⭐️STAR reviews 💬 Text for the fastest response.🔷 Muscular, defined, FIT.🔷 Strong hands, big smile, & nice cocks!! 💪 Gym active five days a week.🔷 Approachable, easy-going, friendly, non-judgmental, and discreet.🔷 Trained & fully equipped to give proper ...
September 6th, 2025
❤️ 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...
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...
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! ...
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...
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 ...
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...
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 ...
🌆 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...
💎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. �...
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...
💎 Sugarboy 💎 👑 Let Me Be Your Prince – All I Need is a King  📍 My Location: Chicago💎 I'm Seeking: a Generous & Discreet Daddy🔥 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...
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...
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...
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...
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...
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 ...
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...
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...
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...
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...
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...
September 5th, 2025
Big, Bold, and Ready to Please 😈🍆 Come Play with Daddy You have been desiring a BBC, haven’t you? That **thick dick, strong, and  commanding presence** that can tell what you need and give it to you. I am  **dominant, experienced, and willing to make you feel as if I am inside of you.** I do  know how to satisfy you, no ma...
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...
🍆💦🍑 9 Inch Thick Power Top Looking To Destroy Your Hole - Discreet🍆💦🍑 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...
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...
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 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 ...
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...
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 ...
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...
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...
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, ...
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. ...
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...
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...
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...
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....
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...
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...
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!!...
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...
September 4th, 2025
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. ...
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...
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: ...
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 ...
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...
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 ...

>>>