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Find kinky men in Chicago

Cobbsmark485
Cobbsmark485
Matured, Lonely-widowed, mud-guy(Oil-Driller-guy). I'm looking for friends and more. I'm looking forward to chatting with profiles with real informations. I don't nag or yell but don't write me if you are not who you are on that app or profile. I will block and report you. I don't want any military men or nurses deployed on any military bases. Looking for LTR but I'm ok if you're just looking for a hookup. We all need a release. I'm a true edged and functionable Versatile here but also love to cuddle, rim ass, oral giving and receiving, massages and very submiive. Very curious to be your slave, inexperienced and wanted to be an experienced student, no degraders, no porn artists. Tested regularly, on PreP. DDF -, HIV- as of November 2025.. Fully vaccinated for COVID and Monkeypox. I like swimming, fishing, drilling, gardenning, cooking, travelling, shopping, bowling, amusement parks, musics, SCI-FI Movies, walking, skating, petting and camping. No man is an island so hit me up and let's see where chemistry takes us next.
Male (50) Chicago, Illinois
DavLView0122
DavLView0122
GWM offers refreshing foot massage to young prof men/grad students GWM is seeking young, professional Caucasian males who want their bare feet massaged and cared for. I am 58 yrs old, intelligent, well traveled, interesting conversationalist. Enjoy foot/face contact with the feet I am massaging. This is the most satisfying foot massage/foot worship you could ever hope to find. My massage is perfect for all young professionals and grad students. It is also great for guys who like attention, who have a dominant side and like to be catered to. It is nurturing and healthy. I prefer a guy who likes having his feet massaged, worshiped, smelled, and worked by an older guy. Maybe you work from home, and would like to work on your computer with a man taking care of your bare feet while you work and talk on the phone? Or, you can easily come to my place and get your massage while you work from here. Just bring your laptop and phone. Maybe you are a grad student who would like to relax, have your shoes and socks removed, and have your bare feet taken care of by me.
Male (58) Chicago, Illinois
CoolGuy6942067
C************7
Career-focused sub 🐷, so my time is purposeful, but my curiosity is endless. I’m drawn to self-aware, creative guys who think intentionally and aren’t afraid of ambition ;). I don’t love listing my laundry list of interests, as they depend on the guy. Connection is more psychological than surface-level for me. Ask specifics, or show me how you think. Into protocol, and consistent training.
Male (25) Chicago, Illinois
PixarDad
P******d
Socially: I really enjoying spending time with people who enjoy both lighthearted and deep conversations. Those who enjoy authentic belly laughs, delicious food, quality beers & cocktails (also sober friendly), and exploring all the wonders & magic the world has to offer. Lastly, really enjoy spending time with people who love movies, music, the arts, and learning from one another. If you’re curious on any of my favorite types of cocktails, foods, movies, music, or plays/musicals, feel free to ask. Sexually: Pretty open to most things since I range from vanilla to kinky. Really attracted to Daddies and Bears, especially Polar Bears. Happy to share specifics in DM’s.
Male (38) Chicago, Illinois
chicago55023
c**********3
I’m Bernard, 39, from Chicago Illinois. My interests are: being jumped on/crushed underneath a mattress, kissed none stop, being rocked like a baby in a guy’s arms, being told I love you consistently. I’m looking for a white male, early to mid 20’s for this kinky adventure. text or message me with interest.
Male (39) Chicago, Illinois
suffolk75208
s**********8
I'm a successful businessman in my early 50s who believes that life is about purpose, resilience, and continuous growth. I've been divorced for nine years and have no ***, which has given me the freedom to focus on my career, personal development, and the experiences that truly matter. I value integrity, respect, and meaningful connections over superficial conversations. In my free time, I enjoy traveling, reading, golfing, fine dining, and exploring different cultures. I'm grateful for the life I've built and believe the best chapters are still ahead, especially when shared with genuine and positive people
Male (50) Chicago, Illinois

New members in Chicago

Cobbsmark485
Cobbsmark485
Matured, Lonely-widowed, mud-guy(Oil-Driller-guy). I'm looking for friends and more. I'm looking forward to chatting with profiles with real informations. I don't nag or yell but don't write me if you are not who you are on that app or profile. I will block and report you. I don't want any military men or nurses deployed on any military bases. Looking for LTR but I'm ok if you're just looking for a hookup. We all need a release. I'm a true edged and functionable Versatile here but also love to cuddle, rim ass, oral giving and receiving, massages and very submiive. Very curious to be your slave, inexperienced and wanted to be an experienced student, no degraders, no porn artists. Tested regularly, on PreP. DDF -, HIV- as of November 2025.. Fully vaccinated for COVID and Monkeypox. I like swimming, fishing, drilling, gardenning, cooking, travelling, shopping, bowling, amusement parks, musics, SCI-FI Movies, walking, skating, petting and camping. No man is an island so hit me up and let's see where chemistry takes us next.
Male (50) Chicago, Illinois
DavLView0122
DavLView0122
GWM offers refreshing foot massage to young prof men/grad students GWM is seeking young, professional Caucasian males who want their bare feet massaged and cared for. I am 58 yrs old, intelligent, well traveled, interesting conversationalist. Enjoy foot/face contact with the feet I am massaging. This is the most satisfying foot massage/foot worship you could ever hope to find. My massage is perfect for all young professionals and grad students. It is also great for guys who like attention, who have a dominant side and like to be catered to. It is nurturing and healthy. I prefer a guy who likes having his feet massaged, worshiped, smelled, and worked by an older guy. Maybe you work from home, and would like to work on your computer with a man taking care of your bare feet while you work and talk on the phone? Or, you can easily come to my place and get your massage while you work from here. Just bring your laptop and phone. Maybe you are a grad student who would like to relax, have your shoes and socks removed, and have your bare feet taken care of by me.
Male (58) Chicago, Illinois
suffolk75208
s**********8
I'm a successful businessman in my early 50s who believes that life is about purpose, resilience, and continuous growth. I've been divorced for nine years and have no ***, which has given me the freedom to focus on my career, personal development, and the experiences that truly matter. I value integrity, respect, and meaningful connections over superficial conversations. In my free time, I enjoy traveling, reading, golfing, fine dining, and exploring different cultures. I'm grateful for the life I've built and believe the best chapters are still ahead, especially when shared with genuine and positive people
Male (50) Chicago, Illinois
chicago55023
c**********3
I’m Bernard, 39, from Chicago Illinois. My interests are: being jumped on/crushed underneath a mattress, kissed none stop, being rocked like a baby in a guy’s arms, being told I love you consistently. I’m looking for a white male, early to mid 20’s for this kinky adventure. text or message me with interest.
Male (39) Chicago, Illinois
CoolGuy6942067
C************7
Career-focused sub 🐷, so my time is purposeful, but my curiosity is endless. I’m drawn to self-aware, creative guys who think intentionally and aren’t afraid of ambition ;). I don’t love listing my laundry list of interests, as they depend on the guy. Connection is more psychological than surface-level for me. Ask specifics, or show me how you think. Into protocol, and consistent training.
Male (25) Chicago, Illinois
PixarDad
P******d
Socially: I really enjoying spending time with people who enjoy both lighthearted and deep conversations. Those who enjoy authentic belly laughs, delicious food, quality beers & cocktails (also sober friendly), and exploring all the wonders & magic the world has to offer. Lastly, really enjoy spending time with people who love movies, music, the arts, and learning from one another. If you’re curious on any of my favorite types of cocktails, foods, movies, music, or plays/musicals, feel free to ask. Sexually: Pretty open to most things since I range from vanilla to kinky. Really attracted to Daddies and Bears, especially Polar Bears. Happy to share specifics in DM’s.
Male (38) Chicago, Illinois

New personal ads in Chicago

CoupleofFun971
Couple (Cuck)

Looking to play with single men IRL or digitally (GF 20)
Kinky Date ● 18 to 80 years ● 500km around USA Aspers
Leon19982
Relationship

Hey, I’m looking for a woman who is either a dom, a mistress, or can be a switch and who is interested in building a monogamous relationship. By the way, I’m still inexperienced in BDSM and I would love to explore it with my partner. Maximum age should be 59. Don’t be shy and message me. Don’t mind dating someone from another country/state.Prefer older women if you’re a dom only.
Kinky Date ● 26 to 59 years ● 500km around USA Dallas
ShakinGraves
Lets do something

Fun and friendly
NSA ● 18 to 80 years ● 115km around USA Huntington
ferriday16055
Dominant woman

Someone that will make me wear girl clothes especially panties and dominant me and make me send pictures whenever they want
BDSM/Fetish Family ● 18 to 80 years ● 25km around USA Ferriday
dallas916535
Who likes Bottom/Sub Muscular Guys?

Want online fun right now wanna show myself off. DM if ur big
NSA ● 18 to 80 years ● 25km around USA Dallas
RumsGood
Hey Girl

Luna do you see me?
Club Buddy ● 18 to 80 years ● 25km around South Korea Pyeongtaek-dong
atlanta9026314
Masculine

Masculine dudes sit back relax
Munch Buddy ● 18 to 80 years ● 25km around USA Atlanta
queensbklatino
Few drinks.. anyone to hang with?

.
Kinky Date ● 18 to 28 years ● 25km around USA Brooklyn
ridemyfaceNY
Need some legs wrapped around my face

Looking for some no string attached fun. Straddle my face and go for a ride. Let’s test out and see how long either one of us could last.
NSA ● 18 to 55 years ● 80km around USA Bronxville
ayodesci
late night adventure???

who wants to get drinks tonight
Kinky Date ● 18 to 25 years ● 25km around USA Washington
Jdaddy2026
Looking for friends!

I’m open minded and easy going looking for some likeminded people to have fun and share some life experiences with. My main objective is to make unforgettable memories in and out of the bedroom!
NSA ● 18 to 80 years ● 75km around USA Evansville
gymshark74
Call me Daddy

Who wants to be a good girl for daddy?
NSA ● 30 to 56 years ● 160km around USA Orwell
atlantaSlim
Hey who’s free tomorrow night❤️🤪

Gorgeous ladies who need to unwind and express their kinks
Kinky Date ● 18 to 80 years ● 25km around USA Atlanta
TH1057
Anyone wanna just talk, text/snap? MSG me!

Anyone! Just looking to connect with new people
NSA ● 18 to 80 years ● 25km around USA Granger
duck2023
Kids just left

Like to eat some pussy tonight
Kinky Date ● 18 to 80 years ● 25km around USA Alma
eli234222
Women hmu

Hmu im in the mood
Kinky Date ● 18 to 80 years ● 500km around USA Pembroke Pines
maajoreater
Link tn

Love to make you cum tn
Kinky Date ● 18 to 80 years ● 25km around USA Phoenix
kar22
Play partner

Looking for any females who are intrested in becoming play partners and essentially fwbs
BDSM Play Partner ● 18 to 79 years ● 100km around USA Baltimore
justaguy8739
Femboy hunting

Looking to collect a harem of femboys, (you know who you are). All are welcome hunters and femboy prey alike.
NSA ● 18 to 80 years ● 500km around USA Centerville
daddy001b
BIG CHOCOLATE

Looking for someone can ride 12 inches BBC
Kinky Date ● 18 to 31 years ● 500km around USA Ola
Humpty459
Looking to find a goth mommy

This hoochie Daddy needs a goth Mommy.....
NSA ● 21 to 60 years ● 50km around USA Janesville
johnnypro1
Mostly browsing.

Recently out of a relationship, so I’m not looking to rush into anything—but I’m open to meeting someone, enjoying each other’s company, and seeing where things go. If it feels right, it feels right.
NSA ● 18 to 80 years ● 65km around USA Renton
beenben
*** niewoehnerd

For whatever
NSA ● 18 to 49 years ● 90km around USA Oak Park
london81997
Need a rigger

I’m trying to get tied up and fucked or ridden until I come before I go to uni so hit me up asap. I can’t host btw
BDSM Play Partner ● 18 to 30 years ● 25km around UK London

More Kinky men in and around Chicago.

Find kinky men in Chicago

Looking for kinky men in Chicago?
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