Rentboy – Largest Gay Male Escort and Massage Site
Find Boys...

Advanced Search

filters



Sexual Position




Cock



Rates


Ethnicity











Interests




















Body Hair






Build








Safe Sex




102 male escorts and male masseurs In Chicago, Illinois

card grid realtime
Previous
page of 5
Next

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.

Actively Looking
- Versatile Cut

Military Beefy Hairy Charming Educated Sweet Stud

Professional muscle great personality, mild to wild escort or sensual massages. I enjoy all types of places, food, music, available for travel.  Recent client comments, "Beautiful body very proportinal. Handsome, very easy to get along with, nice guy, true boyfriend experience, or mild to wild,... (more)
Click to open map Chicago, IL
My Phone Number
Mobile+1 (646) 807-9356Home+1 (646) 807-9356
Email
In Rate Out Rate
$220 $280

SomeAssTime

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
$225.00 $250.00

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

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

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

Actively Looking
41 Versatile Cut

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)
Click to open map Chicago, IL
My Phone Number
Mobile+1 773-413-8086
Email
In Rate Out Rate
$225.00 $250.00

Actively Looking
24 Versatile Cut

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)
Click to open map Chicago, IL
My Phone Number
Mobile+1 (202) 618-0172
Email
In Rate Out Rate
$200 $300

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

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

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

This is an Experiment

I've heard repeatedly that escorts are often hired just to provide companionship. So, I'm testing this theory out. I'm energetic, funny, fun-loving, and always looking for an adventure. I appreciate both high culture and low culture. I'm a perfect companion for a night at the opera or a matiné... (more)
Chicago, IL
My Phone Number
Mobile+1 (773) 888-1574
Email
In Rate Out Rate
Ask me $125.00

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

TRAVLIN SHAMAN

VgL Massuer in the chicago area. I host with class and style in a clean upscale setting with the hands of a skilled and sexy alchemist who can transmute stress into pleasure.
Chicago, IL
My Phone Number
Mobile+1 708 953-9399
Email
In Rate Out Rate
$130 $150

(646) 732-2360

Hello all. I am a very handsome, ivy-league educated man of Middle Eastern (Iranian/Egyptian) descent. I am 26, 6'3'' 195 pounds...have a hairy, sexy, lean/muscular body. A skilled deep-throater and rimmer as well as a tight, muscled-ass bottom, I am very sexually adventurous and would love for... (more)
I'm #6 on the map Chicago, IL
My Phone Number
Mobile+1 (646) 732-2360
Email
In Rate Out Rate
$180 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

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

Actively Looking
31 Top Uncut

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)
Click to open map travel adChicago, IL
My Phone Number
Mobile+1 773-236-0126
Email
In Rate Out Rate
Ask Me $200

Im here to make you feel like you have never felt before

I know you tired of the bs on the dating sites and the unprofessional escorts, well im here to satisfy your needs. Kick off your shoes and relax a little I specialize in pleasure. I am a charismatic passionate man that will have your toes curling and body shaking. Ask for my password to my pics
Chicago, IL
My Phone Number
Mobile+1 (773) 467-6819
Email
In Rate Out Rate
$200/hr $150/hr

Actively Looking
21 Top Cut

Just landed here in Chicago! New hung meat on the shelf for you! - 22

New to your Big city, but I'm a big guy so I think I'll fit in just fine! I'm 6'2 190lbs.I'm 12 inches hung and extremely handsome. Everyone says they're dominant, but are they really? Well I'm the real deal hit me up for a great time with a masculine guy.3129614795
travel adChicago, IL
My Phone Number
Mobile+1 (312) 961-4795
Email
In Rate Out Rate
Ask me Ask me

Premium Gold

LEO

HANSDOME IN TOWN FOR SHORT TIME

HI MY NAME IS LEO, 27 YR, SEXY & MASCULINE GUY, WELL TRAVELLED READY TO GIVE YOU A HIGH CLASS SERVICE!!!! TONED MUSCLE BODY, 180 cm , 92 kg SEXY BODY 8.5" THICK & HARD. 44 FEET,HOT MUSCLE ASS & DEFINED LEGS. I'M AVAILABLE FOR INCALLS OR OUTCALLS. I PROVIDE MASSAGE OR ESCORT SERVICES (VAN... (more)
travel adChicago, IL
My Phone Number
Mobile+1 (646) 588-1250Home+1 (646) 588-1250
Email
In Rate Out Rate
ask me ask me

Latin twink

Young Hispanic twink ready for action.  Clean, in shape, smooth Bttm ready for some company. Call, text, or message me for any questions
Chicago, IL
My Phone Number
Mobile+1 9513318137
Email
In Rate Out Rate
Ask me $200

Irish lad - funny, fit and free-spirited

Thanks for looking at my ad! I'm an Irish lad here in Chicago, available for incall and outcall (prefer outcall). I'm known for being the type of man who will make you laugh, show you the best of Chicago. Whether it's a dinner, evening's entertainment, a night of conversation and passion, or a trip... (more)
Chicago, IL
My Phone Number
Mobile+1 (708) 600-6754
Email
In Rate Out Rate
$200 $200

Previous
page of 5
Next
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!