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

Advanced Search

filters



Sexual Position




Cock



Rates


Ethnicity











Specialties




















Body Hair






Build








Safe Sex




99 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.

Ready for a great time?

Hey Guys! I'm a young, masculine, fun, active guy, that gets into just about anything. Into something , but not sure if I am? Simply ask! I enjoy making you quiver with pleasure and am damn good at it. Make sure to contact me. Discretion is assured.it
Chicago, IL
My Phone Number
Mobile+1 (630) 631-2148
Email
In Rate Out Rate
Credit Cards and Paypal accepted $250; 500 for 4hand

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 Por... (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

CHICAGO'S HAIRIEST GINGER OTTER!

I will be at the buckwood campground this weekend in Indiana. 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 ... (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 ACTITUD , . REVEWS: WWW.DADDYSREVEWS.COM.search for Midwest, IL .Chicago / marchello 26/5'11" 175 /muscular buff/natural smooth all over/ AV... (more)
Chicago, IL
My Phone Number
Mobile+1 312-375-6020
Email
In Rate Out Rate
$180$ Ask me

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

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
26 Versatile Uncut

Eastern European Experience

Honest gentleman 26 yo Eastern European stud that everyone describes as a sweetheart. bad boy body, Great kisser, skilled 8" top - amazing bottom. I love to make people happy. Friendly and professional with perfect hygiene. Picture are recent and genuine. Text me (no emails) - no blocked numbers.
Chicago, IL
My Phone Number
Mobile+1 530-936-7883
Email
In Rate Out Rate
$250 $250

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

CLEAN, Dominant , STUD

hello I'm a masculine, discreet,  good looking guy that is here for a mutual beneficial  TRUE experience .  I prefer to go out for dinner or any cuasul date to get to know you first , don't have to though , also dont hesitate to ask me to visit you if your out of state , I love travel... (more)
I'm #4 on the map Chicago, IL
My Phone Number
Mobile+1 3128591581
Email
In Rate Out Rate
Ask me asm me

COUNTRY CABALLERO

Hi Chicago! I'm just a country boy visiting from the plains of South America. Taking a year off from University and traveling the world b/4 heading back to school in January. I have an interest in fine foods and dining. My goal is to open my own restaurant after school.Let me whip up a little d... (more)
I'm #5 on the map Chicago, IL
My Phone Number
Mobile+1 (773) 367-7078
Email
In Rate Out Rate
Out call only $275

September 1 - September 4: CHICAGO

8/28: LAST DAY IN SAN JOSE!8/29 - 9/1: San Francisco 9/1 - 9/4: Chicago9/4 - 9/6: San Francisco 9/6 - 9-16: West Hollywood/Los AngelesI can host in my great Boys Town suite or travel anywhere nearby. I'm a Vers/Top, but it doesn't need to go there. I like a guy who appreciates my endowment... (more)
I'm #6 on the map travel adChicago, IL
My Phone Number
Mobile+1 415-609-2487
Email
In Rate Out Rate
ASK ME 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

Award-Winning Porn Star in Chicao 8/31 to 9/3 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

Actively Looking
24 Top Cut

...

prefer email, then text.
travel adChicago, IL
My Phone Number
Mobile+1 (312) 854-9204
Email
In Rate Out Rate
Ask me $180/hr

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

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 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

Young, athletic model for massage and more

I'm a young, fun, intelligent, sexy model working as an escort to help pay my way through school. I've been an athlete my whole life and my body shows it. I'm well-cultured and traveled, able to hold a meaningful conversation, and a lot of fun to be around. I'm very adaptable to any situation, and a... (more)
Chicago, IL
My Phone Number
Mobile+1 (831) 512-9356
Email
In Rate Out Rate
Outcall only $200

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

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

Brown, Hard and ready! 11 inch Hershey Bar!

What's up everybody!?!? What you have here is not your typical entainer for the evening. I'm the REAL DEAL! I'm masculine, muscular "Very Hung", dominant and articulate. I'm open to practicing new fettish and role play. I can travel or host. When it comes to making appointments just email, text or c... (more)
I'm #7 on the map Chicago, IL
My Phone Number
Mobile+1 7087379133
Email
In Rate Out Rate
ask ask

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

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!