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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May 17th, 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. ...

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...

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....

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: ...

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...

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!...

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...

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 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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

May 16th, 2025

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...

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...

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...

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 ...

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....

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...

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 ...

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...

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...

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...

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!...

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...

Upscale apartment with all facilities. I can please you here or at your home. [Male for Male] Bradley M4M Escort in Chicago Area Hey guys, M4M escort in the Chicago area. I am Bradley, 31, fit, European by birth and waiting for you to call me so I can show you a great time. Tall and well hung. View my online profile and message me BradleyKM4M. Send your photo for mine.   No ...

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...

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...

🌆 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...

May 15th, 2025

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...

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! ...

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 ...

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...

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...

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...

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. ...

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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. 🏳️‍🌈 About Me: 🌟 Handsome and Confident 🌴 Proud Puerto Rican 💃 Passionate Dancer 😘 Great in Bed!!! I'm on the lookout for se...

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...

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, ...

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...

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...

💎 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...