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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
ChiOkieSwitch
C***********h
Bondage and domination are pretty much the key to getting me to that perfect subby headspace. Really enjoy chastity, slings, leather, rubber, bondage, electro, shaving, hypno, and more. It’s not a full list, just the start of a conversation. When it comes to gear, the more the better... but some of the best sessions have had no gear or restraints at all. Submissive 99% of the time, but the right boy can turn a more dominant switch. Not sure sometimes until we meet. Hearing or seeing a boy squirm or moan in *** is going to get me hard. Or might just tie you down and use you as a living dildo. If we’re fucking: mostly bottom, only sometimes top. On PrEP and tested quarterly. No ***, ***, ***s, and the like. Spanking usually results in me being violent. Few have successfully gotten me to the right headspace. Please discuss before trying. Often locked in chastity without the keys. Would like to explore slave training/TPE submission. Chaste/locked status: Current: Locked (90% of the time) as of November 6, 2023 Previous longest: No jo since Aug 14, 2021, locked on Sep 22 2021- June 2022. (Permalocker Sep 30 2021-Jan 12 2022)
Male (44) 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
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
c0redloop81
c*********1
General submissive into rope bondage and captivity as well as wrestling, gear, and various other activities. Hopes are not high but I’ll give it a try.
Male (34) 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
ChiOkieSwitch
C***********h
Bondage and domination are pretty much the key to getting me to that perfect subby headspace. Really enjoy chastity, slings, leather, rubber, bondage, electro, shaving, hypno, and more. It’s not a full list, just the start of a conversation. When it comes to gear, the more the better... but some of the best sessions have had no gear or restraints at all. Submissive 99% of the time, but the right boy can turn a more dominant switch. Not sure sometimes until we meet. Hearing or seeing a boy squirm or moan in *** is going to get me hard. Or might just tie you down and use you as a living dildo. If we’re fucking: mostly bottom, only sometimes top. On PrEP and tested quarterly. No ***, ***, ***s, and the like. Spanking usually results in me being violent. Few have successfully gotten me to the right headspace. Please discuss before trying. Often locked in chastity without the keys. Would like to explore slave training/TPE submission. Chaste/locked status: Current: Locked (90% of the time) as of November 6, 2023 Previous longest: No jo since Aug 14, 2021, locked on Sep 22 2021- June 2022. (Permalocker Sep 30 2021-Jan 12 2022)
Male (44) 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
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
c0redloop81
c*********1
General submissive into rope bondage and captivity as well as wrestling, gear, and various other activities. Hopes are not high but I’ll give it a try.
Male (34) Chicago, Illinois

New personal ads in Chicago

Alan-6102
New dildo

Someone help me choose a new dildo 😝😝
BDSM/Fetish Family ● 18 to 80 years ● 500km around UK Awsworth
Casper269
Shower Time

I would like to have shower sex and explore each others body and more.
Kinky Date ● 18 to 30 years ● 25km around USA Buffalo
The_Director_
Kinky Party

If I throw a kink party, who all would be willing to join? It would be BYOB tho
BDSM/Fetish Family ● 18 to 80 years ● 65km around USA Jacksonville
minneapolis88840
Looking to leave you pleased and satisfied

Let’s meetup and have some naughty fun it will be worth it trust me darling ;)
NSA ● 18 to 80 years ● 55km around USA Minneapolis
hillsdale84240
SheFights

Is anybody even into this kindve stuff anymore?
BDSM Play Partner ● 18 to 80 years ● 25km around USA Hillsdale
humbledpie
Housepig for Ladies

Naked housepig to do Your chores as You sit and relax?.Shout PIG!! if You need something and i would stop and move to You awaiting Your orders.
Pro-Dom/me Session ● 18 to 75 years ● 100km around UK Manchester
Domseeker123
Seeking Master Domination

Dom seeker looking for experience Master / Sir.
BDSM Play Partner ● 30 to 72 years ● 25km around USA Fort Myers
Lespaul1959
Cyberplay

Anyone want to trade? 😈
BDSM Play Partner ● 18 to 80 years ● 500km around USA North Garden
MactavishStir
Add snap

Rogue_mactavish
NSA ● 18 to 80 years ● 65km around UK Stirling
gaviota50550
Looking for like minded couples/people

Let’s play!
Kinky Date ● 18 to 80 years ● 5km around USA Gaviota
kyler0
Anyone looking for anything fun hmu

Bored and looking for anything fun just text me and we will see where it goes
Kinky Date ● 18 to 80 years ● 125km around USA Glendale
michaellikesfun
I wish some beautiful girl was with me

I wish some cute beautiful girl was with me rn naked with nice titties and a nice butt spooning with me in bed going to sleep peacefully and then her putting my cock in her wet pussy with my hands on her tits falling asleep with my hard cock in her wet pussy and waking up with sticky cum dripping out
Club Buddy ● 18 to 80 years ● 25km around USA Spring Lake
denver50205
Free this weekend

I have a house to myself this weekend so I’m down for anything
Munch Buddy ● 18 to 78 years ● 175km around USA Denver
Reece033
Where are the dom/switch women at? 🙂‍↔️

Looking for a dom/switch women to explore my mommy issues 🙂‍↔️
BDSM Play Partner ● 18 to 80 years ● 500km around UK Newcastle upon Tyne
great665
Cuckold/open relationship on her end only

Mexican/29 looking meet a Size Queen who wants a safe space to be yourself while you're encouraged. A proud cuckold/submissive, online only based in Nebraska but open to anyone who's ok with online. On a healing journey lets all be our most authentic self❤️
BDSM Play Partner ● 18 to 99 years ● 500km around USA Calexico
Pureplay
Casual, cuddles & a bit nerdy 😈

25 year old…can be nerdy sometimes…FWB, casual, cuddles whatever 😜… Lets help each other out🍆💦😈
NSA ● 18 to 80 years ● 20km around USA Dallas
dumfries-and56794
Soooo horny

In bed alone, naked and so horny
NSA ● 28 to 80 years ● 145km around UK London
michaellikesfun
Soft pretty hands around my cock

I want my cock to be jerked off by some pretty hands
Munch Buddy ● 18 to 80 years ● 25km around USA Spring Lake
Kingofroses
Looking for friends

Just tryna be make friends n overall just have people to chat with in my free time
NSA ● 18 to 80 years ● 500km around Canada Leduc
HighlyAnti
Drinks tonight ?

Drinks on this nice Friday night ?
Kinky Date ● 18 to 80 years ● 25km around USA Houston
Hishouse13
Its my birthday

Any ladies be interested in helping a man celebrate his birthday today?
Kinky Date ● 18 to 80 years ● 80km around USA Cleveland
letsdoittt
Hmu new heree

Let's talk about it
NSA ● 18 to 80 years ● 35km around USA Howell
Rob2579175
Use me as your boytoy

I really wanna eat pussy, worship boobs , ass and feet of women. If interested please hit me up . I am available at anytime in Toronto region and also I can travel almost anywhere around 500km radius to Toronto. I am also interested in so many other things please message me personally to know more
NSA ● 18 to 99 years ● 500km around Canada Toronto
BoiseSubbie
Sissy slave for your chores

I love being used as a maid/housewife, give me your chores and use me while I do them. I'm open to anything, not seeking payment just fun😈
BDSM Play Partner ● 18 to 80 years ● 95km around USA Boise

More Kinky men in and around Chicago.

Find kinky men in Chicago

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