Rentboy – Largest Gay Male Escort and Massage Site

Advanced Search

filters



Sexual Position




Cock



Rates


Ethnicity











Interests




















Body Hair






Build








Safe Sex




85 male escorts and male masseurs In Chicago, Illinois

card grid realtime
page of 5
Actively Looking
39 Cut

Time to Fall Back into These Arms

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)
Click to open map Chicago, IL
My Phone Number
Mobile+1 (773) 354-8802
Email
In Rate Out Rate
$225.00 $250.00

Latin Twink

Very smart and great personality make for amazing company.  Enjoy a good bottle of wine, dinner, going out for drinks, and exploring the city and traveling.  Let me know what you are interested in and we will go from there.
I'm #2 on the map Chicago, IL
My Phone Number
Mobile(951) 331-8137
Email
In Rate Out Rate
Ask me $180

top cuban 10 inches (real big dick) now in Chicago

 hello .. my name is maykol!!'m Cuban and I live in Madrid at the moment !!for the first time in the USA and I'll be a week in Chicago ! I'm very masculine, sexy and very sympathetic!! I have very good body as I train every day. I like to have fun in sex, and passionate  be dominant at the... (more)
Chicago, IL
My Phone Number
Mobile+1 (323) 304-4418
Email
In Rate Out Rate
Ask me Ask me

ADULT FILM STAR THAT LOVES SEX , SEX AND SEX !!

I'm a muscular jock that is well traveled, passionate and wild with a heart of gold ! No attitude or judgements. I can be extremely affectionate, romantic and I love to kiss. But if you're looking for something a little more wild, rough or if your into leather fetish or any other fetish I'm your man... (more)
I'm #3 on the map Chicago, IL
My Phone Number
Mobile+1 773-413-8086
Email
In Rate Out Rate
$225.00 $250.00

One of the BEST TOPS in Chicago!

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 return to ... (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

In Chicago Friday 11/28- Sunday 11/30

Hey    Looking to have some fun tonight or interested in booking for the future?   I'm available for 1 on 1 privates, dinners, muscle worshipping, fetishes, shopping sprees, or if you just want someone to spend time and talk too.   I come discreet and ready to have some fun... (more)
Chicago, IL
My Phone Number
Mobile(352) 346-0181
Email
In Rate Out Rate
$140 $160

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) 905-4691
Email
In Rate Out Rate
Ask me Varies

Bigger is always better

COME experience a session that will blow your mine!!! I specialize in 1st timers , which I aim to make your 1st experience a very pleasurable one, Massages, Role-Play, Mild-to-Wild, Domination, Companionship, Private Sessions, etc Certified Massage therapist!!! If you want to have one of the best se... (more)
Chicago, IL
My Phone Number
Mobile+1 (630) 917-1884
Email
In Rate Out Rate
$250 $300-400

MARCHELLO HOT LATINO in CHICAGO BOOKING NOW 100%DESCRETE/ PICS

BEST WAY TO GET A HOLD OF ME RIGHT AWAY BY CALLING OR TEXT ME, Chicago escort/very good looking LATIN VERY FRIENDLY ESYGOIN LIKE TO KISS ORAL MAKING LOVE, FREE ACTITUD , . 26/5'11" 175 /muscular buff/natural smooth all over/ AVAILABLE FOR ALL AGES AND SHAPES , LIKE OLDERS GUYS, IAM FREE OF STD HIV, ... (more)
Chicago, IL
My Phone Number
Mobile+1 312-375-6020
Email
In Rate Out Rate
$180$ Ask

Actively Looking
24 Top Cut

12IN HOSTING IN MY OWN LAKEVIEW APARTMENT $100 SPECIAL OR I DRIVE

I AM THE COMPLETE PACKAGE IF YOU SEE SOMETHING YOU LIKE CALL TXT ME NOW YOU WILL NOT BE DISAPPOINTED. I LOVE WHAT I DO, AND YOU WILL LOVE HAVING ME :) DEVONSTARR 100% TOP DOWN TO EARTH AND LEVEL HEADED. MILD TO WILD, YOUR CALL. MUSCULAR, LEAN, 24Y/O CLEAN CUT WELL GROOMED, KIND AND GENTLE AS YOU CO... (more)
Click to open map Chicago, IL
My Phone Number
Mobile+1 (773) 628-3772
Email
In Rate Out Rate
$150ASK 100SPECIAL $200ASK 150 SPECIAL

Actively Looking
36 Top Cut

Masculine Sexy Top

Sexy,  fun &  well endowed, masculine top. I'm mature,  confident, and always professional. I always deliver, never under perform. I can be your passionate boyfriend or a dominant and aggressive pig. I get into most every scene, I love to party. I've got a thick and meaty 7.5 inch... (more)
Click to open map Chicago, IL
My Phone Number
Mobile+1 (310) 927-9484Home+1 3109279484
Email
In Rate Out Rate
$250 $250

Insatiable Muscled Jock-Make your Reservations NOW!!! 4 Days ONLY!!! Dec 4th to Dec 8th (303) 359-3192 WWW.ELIDANIELSENTERTAINMENTNETWORK.COM

***CHICAGO AREA for 4 DAYS ONLY 12/04 - 12/08 & booking apts before I arrive***LOVE WHAT I DO, HOW I DO IT, & WOULDN’T CHANGE A THING ABOUT IT......I’m not a porn star by choice but definitely down to make some memories on camera…Visit My Website to see some... (more)
I'm #7 on the map Chicago, IL
My Phone Number
Mobile+1 (303) 359-3192
Email
In Rate Out Rate
$300 CASH or CREDIT $350 CASH or CREDIT

100% Texas Beef!

31 yr. old Latin male, 5'8, 31" waist, 156 lbs. Discreet, respectful, easy going, open minded, adventurous, spontaneous, and most importantly, I play well with others :) Please feel free to call or text me at anytime. Here is the link to "Another Morning" ENJOY!  http://www.pornhub.com/vi... (more)
I'm #8 on the map travel adChicago, IL
My Phone Number
Mobile+1 773-236-0126
Email
In Rate Out Rate
Ask Me $200

Natural, Athletic, Discreet

Discrete guy here. Drama free and always on time. Awesome cocksucker! I am interested to please and also can go any where from mild to wild for an enjoyable man on man interaction. I'm cool with working with couples or other escorts. Party's are fun. I aim to please. Can be dom or sub. I'm versatile... (more)
Chicago, IL
My Phone Number
Mobile+1 (312) 343-9348
Email
In Rate Out Rate
$200 $200

Versatile Midwestern Bubble Butt Porn Dude Visiting

Lets have some fun while I'm visiting!  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 fisting...... (more)
Chicago, IL
My Phone Number
Mobile+1 (402) 871-6928
Email
In Rate Out Rate
$200 $240

Actively Looking
22 Top Cut

Shaun the freak

Hi guys new to escorting just unleashed my inner freak for generous males I'm very open to trying new and excited things I have an amazing 10 1/2 inch dick that seems to stay hard and ready I'm very discreet and  I'm into fulfilling fantasy's and being a partner as well  for companionship ... (more)
travel adChicago, IL
My Phone Number
Mobile+1 (773) 557-6837Home(773) 557-6837
Email
In Rate Out Rate
Ask me Ask me

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

Six Packed, THICK, mushroom headed and EXCEPTIONAL 11"; 5.10", 180lbs 30w, 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: SmoothOne2008@hotma... (more)
Chicago, IL
My Phone Number
Mobile+1 (312) 731-2394
Email
In Rate Out Rate
Out only $300hr

BBVID STAR Brody Primal in CHI

Sexually open, aggressive vers guy here.. few limiTs..
Chicago, IL
My Phone Number
Mobile+1 (312) 978-7096Home(312) 978-7096
Email
In Rate Out Rate
$225 $225

Hot , Smooth , Clean , Discreet...

Are you looking for an amazing experience? Then you are at the right place. Hey guys. My name is Luis. Clean, toned, smooth, very discreet. I can come over to your hotel room or your own place. In Chicago or burbs. If you would like to come to me I can host too. Providing amazing full body massage. ... (more)
Chicago, IL
My Phone Number
Mobile+1 (630) 999-7741
Email
In Rate Out Rate
$160 $160

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)
I'm #9 on the map Chicago, IL
My Phone Number
Mobile+1 312-391-4541
Email
In Rate Out Rate
Ask me $225

I can keep you warm ;)

Hey! My name is Riley.  I am friendly, kind, fun, athletic and love to have fun. I only play safe and up for almost anything. I can accommodate you and For sure keep you warm ;)
Chicago, IL
My Phone Number
Home+1 (312) 576-6901Home+1 (312) 576-6901
Email
In Rate Out Rate
ask me ask me

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!