Rentboy – Largest Gay Male Escort and Massage Site

Advanced Search

filters



Sexual Position




Cock



Rates


Ethnicity











Interests




















Body Hair






Build








Safe Sex




87 male escorts and male masseurs 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.

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)
I'm #1 on the map Chicago, IL
My Phone Number
Mobile+1 (773) 354-8802
Email
In Rate Out Rate
$225.00 $250.00

Fun guy next door!

Hey guys, I'm a fun, sensual guy. I really enjoy to sucking cock and like to kiss! Versatile when it comes to fucking. I enjoy pleasing a man! Let me fulfil your fantasies and desires! Send me a text or email! Look forward to hearing from you!
I'm #2 on the map Chicago, IL
My Phone Number
Mobile+1 (312) 725-0690
Email
In Rate Out Rate
$250 $300

Chocodick4u search no farther I'm all the man you need..

I Have 3 words for you...DOMINANT, AGGRESSIVE & VERBAL!    MALE COMPANION VERY DISCREET AND PRIVATE. Ready to explore your wildest fantasy AND BE PLEASED IN EVERY WAY POSSIBLE. Guaranteed a satisfying, fun, safe time, no rushed service Companionship, massage No discrimination against... (more)
Chicago, IL
My Phone Number
Mobile+1 (202) 618-0172
Email
In Rate Out Rate
$200 $300

CHICAGO'S HAIRIEST GINGER OTTER!

If you are looking for the hairiest ginger in Chicago, then I am your man! I am a young, educated college student. Fiery red head available for your desires. I clean up well for dinner and special events, also a great conservationist. Or if you have something more scand... (more)
Chicago, IL
My Phone Number
Mobile+1 (773) 574-0912
Email
In Rate Out Rate
$220 $200

Midwestern Bubble Butt *PORNSTAR*

Lets have some fun! Private Gallery Password is:  enter  Also there is plenty of pornography to see what you’re getting :-)100% Discretion assured!Companionship and conversation are a no brainer for me - whether its cocktails and dinner you'd like, you just need some man to man time ... (more)
Chicago, IL
My Phone Number
Mobile+1 (402) 871-6928
Email
In Rate Out Rate
$220 $260

Hi everyone! My name is Tony you typical Cuban lover, very passionate, laid-back, nice, educated guy.I'm also very discrete,and respectful and a little shy.If you are looking for a nice relaxing time or just a nice company for a dinner etc..i'm your guy.  Hope to hear from you soon and please o... (more)
I'm #3 on the map Chicago, IL
My Phone Number
Mobile+1 (630) 639-3614
Email
In Rate Out Rate
Ask me200 $350

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 natural and confident top, professional, educated and very into what I do. I’m 27, 5’11, 207 lbs, brown hair, hazel e... (more)
Chicago, IL
My Phone Number
Mobile+1 (872) 216-1618
Email
In Rate Out Rate
Ask me $300

Actively Looking
34 Top Cut

In Chicago XXX Italian Stud - From L.A. This Week Only!

Easy going with a good sense of humor, mature & confident, I know how to deliver what you need. From a passionate boyfriend experience to a dominant and aggressive top. I get into most every scene & I love to party. I've got a thick and meaty 8 inch cock, with big low hanging balls.  I ... (more)
Click to open map Chicago, IL
My Phone Number
Mobile+1 (310) 927-9484Home+1 3109279484
Email
In Rate Out Rate
Varies- Ask Me $250

As seen in Raging Stallion's "Young Warriors"

I am a sociable, fun, down-to-earth & down-for-whatever guy who is the perfect companion for a night on the town, a lazy afternoon at home, or any other kind of fun you can imagine. I am a college student who models and does adult films. I am everything you can possibly ask for in a companion: A... (more)
Chicago, IL
My Phone Number
Mobile+1 206-681-3304HomeNO BLOCKED CALLS
Email
In Rate Out Rate
$200 $200 + cab

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 STD 26/5'11" 175 /muscular buff/natural smooth all over/ AVAILABLE FOR ALL AGES AND SHAPES , LIKE OLDERS GUYS, IAM FREE OF STD HIV, IN/OUT ... (more)
Chicago, IL
My Phone Number
Mobile+1 312-375-6020
Email
In Rate Out Rate
$180$ Ask me

Award-Winning Porn Star in Chicao 9/29 to 10/3 only.

Looking for two overnights!Explorative and educated, I do like to try new things. I am currently in college for medicine, so I can continue a conversation if that is what you desire. If not, we can get to business. I don't offer the boyfriend experience in public. Only while we are indoors. I l... (more)
travel adChicago, IL
My Phone Number
Mobile+1 (615) 681-7193
Email
In Rate Out Rate
Ask me $300

Visiting Oct 3-4 only

Visiting, Oct 3-4 Only.Hello I am always in great shape, Hairy 5'10" 225# 53C, 19A, 32W, 28Th, very handsome very masculine, abs, tan, Hairy at the moment, all for real, I also give great massage, always better to text me or Email for more info.Always better to book ahead also.702-530-6161
travel adChicago, IL
My Phone Number
Mobile+1 (702) 530-6161
Email
In Rate Out Rate
$200 $220

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 #5 on the map Chicago, IL
My Phone Number
Mobile+1 (773) 870-2154
Email
In Rate Out Rate
$225/hr $250/hr

I aim to please.

Hey gents, Thanks for checking me out, the fastest way to get a hold of me is to text. I am a fiery, educated, young man that enjoys pleasing YOU! A gentleman in the streets and a freak in the sheets, I clean up rather well and am available for dinner and events, or for something more scandalous. Ha... (more)
Chicago, IL
My Phone Number
Mobile+1 6302201736
Email
In Rate Out Rate
N/A $250/hr 400/2hr

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 #6 on the map Chicago, IL
My Phone Number
Mobile+1 773-413-8086
Email
In Rate Out Rate
$225.00 $250.00

Actively Looking
24 Top Cut

...

prefer email, then text.
Click to open map travel adChicago, IL
My Phone Number
Mobile+1 (312) 854-9204
Email
In Rate Out Rate
Ask me $200/hr

Actively Looking
25 Top Cut

PORNSTAR TOMMY DEFENDI

Hi there, let me start with thanking you for your interest and curiosity in my services. I have been performing on camera for over 6 years now and escorting since Sept 08'. I am very adventurous and love to meet new people. Sharing genuine expieriences with others and making fantasies come true ... (more)
Chicago, IL
My Phone Number
Mobile+1 (702) 518-5440
Email
In Rate Out Rate
Ask me Ask me

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 decid... (more)
Chicago, IL
My Phone Number
Mobile+1 7735677170
Email
In Rate Out Rate
Ask me Ask me

Muscle jock / Porn Model

Chicago Sept 27-30! What you see is what you get with me (if not better!) and I have the reviews to back it up - link below. Discreet & professional! I'm a nice guy who's done some porn, constantly at the gym and am also a certified personal trainer in Arizona... Big muscle here! I'm... (more)
Chicago, IL
My Phone Number
Mobile4802270847
Email
In Rate Out Rate
$300 $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)
I'm #8 on the map Chicago, IL
My Phone Number
Mobile+1 312-391-4541
Email
In Rate Out Rate
Ask me $225

Actively Looking
24 Top Cut

XXL 12in HOSTING DOWNTOWN CALL FOR LOCATION

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, 23Y/O CLEAN CUT WELL GROOMED, KIND AND GENTLE AS YOU CO... (more)
Chicago, IL
My Phone Number
Mobile+1 (773) 628-3772
Email
In Rate Out Rate
$150ASK $200ASK

Tall, Dark, & Handsome......

I'm a College educated professional. I'm discreet and respect a clients need for the same in return. I'm passionate about giving you the best experience you can get, weather that be a night out on the town or just an evening in. I enjoy most scenes and am open to many possibilities. Plea... (more)
Chicago, IL
My Phone Number
Mobile+1 (312) 532-3614
Email
In Rate Out Rate
Ask me for options/locals $250

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!