Rentboy – Largest Gay Male Escort and Massage Site

Advanced Search

filters



Sexual Position




Cock



Rates


Ethnicity











Interests




















Body Hair






Build








Safe Sex





89 male escorts and male massage therapists In Chicago, Illinois

card grid realtime
page of 5

Sorry!

The ad you tried to reach is no longer available. Below are ads in the same location as the ad you tried to reach... or try searching again.

Southern Hospitality,

Face and additional pictures are available per request. Laid back, confident, very good looking. Over all great guy. Southern born and raised, accent and all. I genuinely enjoy what I do, so I have no doubt you'll enjoy what I do too. I respect everyone's privacy and any encounter is between us. Fee... (more)
I'm #1 on the map Chicago, IL
My Phone Number
Mobile+1 (404) 860-1213
Email
In Rate Out Rate
Ask me Ask me

FROM THE DARKNESS COMES YOUR LIGHT

First and formost I would like to thank the 1.5 million viewers for ranking my performance one of the all time highest rated & most watched in pornhuBB history.  Never saw that coming.   That said, if you know what you like and like what you see...then indulge yourself. SXVideo p... (more)
I'm #2 on the map Chicago, IL
My Phone Number
Mobile+1 (773) 354-8802
Email
In Rate Out Rate
$250 $225

Massage By Eric

Come experience my art of healing... I am a Licensed Massage Therapist (LMT) and artist weaving the therapeutic and erotic, onto your body's canvas. I offer Swedish Full Body massage and Thai Yoga variations, which involves a floor matt and assisted stretching, compressions and acupressure with... (more)
I'm #3 on the map Chicago, IL
My Phone Number
Mobile+1 (612) 360-0162
Email
In Rate Out Rate
$100 $100

Total Satisfaction

Sexy, Fun, and Well-Endowed, Masculine Top... Im easy to be around, have a sense of humor and alays alow things to play out at your comfort level. I'd say that Maturity Confidence, Professionalism and a love for fun define me. If you're looking for two guys I work with several really hot men th... (more)
Chicago, IL
My Phone Number
Mobile+1 (310) 927-9484Home+1 3109279484
Email
In Rate Out Rate
Ask me for details Ask me for details

Actively Looking
32 Versatile Cut

Aggressive, Passionate, and Discreet.

If an Authentic Experience is what you're wanting, you don't need to look much further . . . I honestly dig what I do. I have a lot of fun with it, and I know what i'm doing. I'm New, and I'm Honest. Real Age, Real Photo. Clean Guaranteed! Feel free to call or text w/ any further questions.
Chicago, IL
My Phone Number
Mobile+1 (312) 483-7976
Email
In Rate Out Rate
Ask me Varies

Returning to Chicago March 29!!!

I'm a hot and passionate companion. I can get into intelligent conversation over a nice dinner as easily as I get into sensual play. You will find that I am dependable, professional, real and easy to get along with. I enjoy theatre, travel, fine dining, shopping, movies, and more.  I returned t... (more)
I'm #4 on the map Chicago, IL
My Phone Number
Mobile+1 (773) 870-2154
Email
In Rate Out Rate
$225/hr $250/hr

You have stepped into the erotic zone

Tall,Dark,and Handsome Prince looking to relieve you of all your built up tensions, give you the most exquisite pleasure,and take you through the most ultimate experience.Built like a "Super Hero" and hung like a " PornStar".Seriously! Doing In-Calls Out-Call$250.00 an hour $1000.00for day.Call me ,... (more)
Chicago, IL
My Phone Number
Mobile+1 (312) 344-3052
Email
In Rate Out Rate
$250.00 1 hour $250.00 1 hour

I am the best .no worries

 TRUE  Passionate experience for the right person  , also with alot more pics to share upon request, im very athletic and my ad is real and my motives are to have fun  !!  ,I  provide a vast array of options such as personal training or martial arts, domination, wrestli... (more)
I'm #5 on the map Chicago, IL
My Phone Number
Mobile+1 3128591581
Email
In Rate Out Rate
Ask me asm me

Midwestern Bubble Butt *PORNSTAR*

Back home for a short time ;)Check out some of my porns there and there.  And no, I'm not a total PowerBottom!  I just play one in the movies!  Of course some of the best tops are bottoms.  I am mild to wild kinky or vanilla and very well experienced in many fesishes...easy-going... (more)
Chicago, IL
My Phone Number
Mobile+1 (402) 871-6928
Email
In Rate Out Rate
$220 $260

**XXL TOTAL TOP ***BOOK NOW!!!**

Six Packed, THICK, mushroom headed and EXCEPTIONAL 11"; 5.10", 180lbs 30w, Tested 3-13-15 and HIV- DISEASE FREE; SAFE ONLY; Available for Block hrs and overnites. FOR THE DISCREET MALE. Please describe what type of service and time frame you want. HEADTURNER; DISCRETION EXPECTED AND INSURED. Email: ... (more)
I'm #6 on the map Chicago, IL
My Phone Number
Mobile+1 (312) 731-2394
Email
In Rate Out Rate
Out Only $300hr

YONG & FRESH SEXY LATINO

HEY GUYS WHAT SUP IM OLIVER A GOOD LOOKING LATINO GUY IM VERY FRIENDLY AND VERY CLEAN...IM 5"8 TALL 148 LBS...NICE THICK 8" UCUT , NICE BUBBLE BUTT LEAN BODY AND ALWAYS READY TO GIVE U A GOOD TIME IM 100% REAL SO IF U ARE LOOKING FOR A GOOD TIME JUST TRY ME AND U GONNA LIKE ME THE BEST WAY TO CONTAC... (more)
travel adChicago, IL
My Phone Number
Mobile+1 323 481 8671
Email
In Rate Out Rate
Ask me Ask me

Stop searching the rest, you've just found the best!

Sexy, intelligent, playful.... Fresh off the farm and well traveled. You can't get any better than that! Romp in the sack? Night on the town? Whats your flavor? Providing an array of experiences and all you have to do is message me and the rest will follow.experienced in erotic massag... (more)
I'm #7 on the map Chicago, IL
My Phone Number
Mobile+1 (312) 967-9612
Email
In Rate Out Rate
Not preferred $200

Hookies Mr. Chicago 2014

Furry muscle guy here to provide excellent companionship. I enjoy dinner dates, cuddling, hitting the town, or just staying in bed all weekend long. You’ll find me a natural and confident top, professional, educated and very into what I do. I’m 28, 5’11, 207 lbs, brown hair, h... (more)
Chicago, IL
My Phone Number
Mobile+1 (872) 216-1618
Email
In Rate Out Rate
ask me $300

Pleasure seeking, sensuous top!

For the discerning gentleman... I'm a masculine, well-endowed top to serve for your pleasure. Accommodating and discreet. Sensual touch and more for an erotic massage; special rates available! Please know that I am also negative, drug/disease free. Available weekdays and nights; most weekends. Email... (more)
Chicago, IL
My Phone Number
Mobile+1 (312) 835-8137
Email
In Rate Out Rate
$160 $180

Irish lad in the big city

A hundred years or more ago, thousands of Irish moved to Chicago to fulfill their dreams of living in tenement housing. Now, in the present, Jack Riley is bringing up the rear. Literally, so to speak. As an Irish immigrant, I bring a great experience to any appointment. I do have the sexy accent, as... (more)
Chicago, IL
My Phone Number
Mobile+1 (708) 600-6754
Email
In Rate Out Rate
$200 $200

All night luva

If you're looking for a handsome face, a sexy build you've found it!!! Have an unforgettable experience with a young, sexy dude seeking to please you, whether through a sensual massage, or being your company through the night which you"re sure to have the best time of your life!! Whatever you decide... (more)
Chicago, IL
My Phone Number
Mobile+1 7735677170
Email
In Rate Out Rate
Ask me Ask me

CHICAGO'S HAIRIEST GINGER

Hello, and thank you for checking out my profile. I am an affectionate individual and love body contact. I am also experienced with BDSM and fisting top. I have a wide range in interest from cuddling to watersports and all that inbetween. Friendly, discrete, educated art student. Contact me via te... (more)
I'm #8 on the map Chicago, IL
My Phone Number
Mobile+1 (773) 574-0912
Email
In Rate Out Rate
$250 $200

DARK SKIN GUY BACK IN STYLE

I''m a Sexy TOTAL TOP Guy 5''5, 150lbs, Clean cut, FIRST TIMERS, ; FREAKS WELCOMED Very Very Professional. Very Discreet. My Services Range From Mild To Wild! Come Let Me Take Care Of You. Ultimately I take control giving you WHAT YOU WANT ; NEED. ***UNINHIBITED*** I also Give Great Massages, Nude, ... (more)
travel adChicago, IL
My Phone Number
Mobile+1 7733125797
Email
In Rate Out Rate
$120 $150

Actively Looking
24 Top Cut

Nerdy artist here

Hey im Joshua, Im 24 Tall hung and ready!   Im artistic hairy and very playful :)   Ive Got a Treasure Trail, furry butt, and Long Hairy Muscular Legs    i Like to stay fit but i dont have a 6 pack, if youre looking for perfectly chisled im not that guy, im nerdy and got so... (more)
Click to open map Chicago, IL
My Phone Number
Mobile+1 415-857-0720
Email
In Rate Out Rate
$250 per hour $220 Per Hour

HUNG STUD(10x6") AVAILABLE FOR YOU-LIMITED TIME

HI ALEX HERE -THANKS FOR CHECKING OUT MY  AD - VISITING CHICAGO - LIMITED TIME. GREAT LOOP LOCATION.Hi - This FRIENDLY sexy masculine hung guy would love to fulfill your pleasures and needs.Naturally smooth skin ,nicely muscled-v-shaped torso and amply hung -a hot 10x6" thick cock.Talented ver... (more)
I'm #10 on the map Chicago, IL
My Phone Number
Mobile+1 (917) 421-6353Home+1 (917) 421-6353
Email
In Rate Out Rate
$250 $300

Actively Looking
31 Versatile Cut

Visiting Chicago Til 3/31

*Friendly-Adventurous-Passionate-Goofy-Masculine-Smooth*  I'm a fun-loving and outgoing guy who appreciates good conversation as well as charismatic sex appeal.  I get into a variety of scenes that can range from vanilla and sensual to wild and erotic.  Tell me any and all of your fa... (more)
Click to open map travel adChicago, IL
My Phone Number
Mobile+1 (347) 201-0309
Email
In Rate Out Rate
$250 $300

Masculine Body Builder

Easygoing and super friendly muscle man. I'm kind of like my dog...I might look like I'm going to bite, but I just want to lick you! I like to kiss and I'm very affectionate. Educated, easy to talk to and good dinner company. Very versatile, can be sweet and playful or kinky and twisted! Really enjo... (more)
Chicago, IL
My Phone Number
Mobile+1 312-391-4541
Email
In Rate Out Rate
Ask me $225

page of 5
in/out rate
in rateIn Rate
out rateOut Rate
star rating
rate from 1 to 5rate from 1 to 5
unratedunrated
Foreskin
cutCut
uncutUncut
Age
# of years# of years
Sexual Position
topTop
bottomBottom
versatileVersatile

signup for the rentboy.com newsletter

Don’t miss out on our latest news, events, and the sexiest men available near you!