r/chicagor4r

i’m convinced the best conversations are the ones neither person planned on having. one minute you’re introducing yourself and the next you’re talking about childhood memories, favorite movies, random opinions, and completely forgetting what time it is.

i’m into anime, horror movies, art, sushi, late night drives, music, and trying new places around the city. i love people with personality, a good sense of humor, and enough confidence to be themselves without pretending to be someone they’re not.

i definitely have a thing for men with a submissive side. i enjoy playful femdomm dynamics, teasing, and someone who’s comfortable letting a woman take the lead sometimes. for me it’s always about chemistry, communication, and finding someone who genuinely enjoys the dynamic.

i’m not looking for the loudest message in my inbox. i’m looking for the one that actually makes me smile.

tell me your age, your neighborhood, and something you’ve always wanted to try but never have. i always find those conversations the most interesting.

i’ve noticed i’m way more interested in personality than perfect pictures. if you can make me laugh, keep a conversation going, and actually enjoy getting to know someone, you’ve already got my attention.

i’m into anime, horror movies, art, sushi, late night food runs, music, and people that make ordinary nights feel memorable. i’m the type that likes talking for hours, sharing random stories, and slowly getting comfortable with someone instead of rushing everything.

i do have a soft spot for a guy with a submissive side. i like playful femdomm dynamics, a little teasing, and someone who’s open-minded enough to explore that side of themselves. for me it’s always about trust, communication, and chemistry first.

i’m not looking for copy-and-paste messages or one-word introductions. tell me something that actually says who you are. what’s a hobby you could talk about for hours? what’s something you’ve always wanted to try?

maybe we’ll have one good conversation… or maybe you’ll end up becoming my favorite notification.

I’m looking for a selfless and mature man who’s genuinely submissive and would take pride in serving me and bringing me pleasure.
I want the kind of guy who’d let me put a collar on him while we’re home alone before he worships my body all over then eating my pussy and focusing purely on my pleasure for however long I want.

I am looking for someone who likes bigger girls. I have an apple body shape and prefer someone who likes it. I’m looking for an eater and will also suck you. I cannot host.

Dm me and we can talk further

Always have weekday availability. Looking to worship someone regularly to relieve their stress. Dommes are a huge plus. Pretty open minded kink-wise. Send your age and location in the first message. What’s our Netflix and chill show?

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i’m the type that gets attached to good conversations. if we can laugh, tease each other a little, and somehow end up talking until way too late, you’re already ahead of most people.

i’m into anime, horror movies, sushi, art, red wine, and exploring new spots around the city. i go to the gym a few times a week and love people who have hobbies they’re actually excited to talk about.

i’ve definitely got a soft spot for a guy with a submissive side. i like playful femdomm dynamics and someone who’s confident enough to be themselves instead of pretending to be someone they’re not. chemistry, trust, and communication matter more to me than rushing anything.

i’m looking for someone who’s funny, respectful, open-minded, and can carry a conversation without making it feel like an interview. quality always beats quantity.

tell me something that actually says something about you. what’s your favorite horror movie, the last anime you binged, or one thing you’re secretly obsessed with?

maybe we’ll end up being each other’s favorite notification.

Please respond with your stats. Open to DM’s right now. Looking to arrange to meet with someone on Friday night. I preference but looking for stats prior. Been feeling neglected lately.

I hope everyone had a good 4th! I was hanging out with my gay bestie this weekend and we saw so many handsome guys walking around the city and it got us reminiscing about the many times we used to share ALPHA type men when we were younger and more wild/slutty about these things. But what the heck, we decided to try again. If you are a fit guy in the city, open minded, and with experience being serviced or pleased, we'd love to hear from you and see where this goes. We would ideally like something ongoing. We are very discreet, biz exec types and respectful about this. Hope to hear from you!

I don't live in the city anymore, but I still come in often for various events. Square Roots is one of my favorite free music events in Chicago. Looking for a daddy type in his 40s to hang out with. Let's hold hands, grab a drink and make out while vibing to some great music.

Full disclosure I am happily married and enm. We play separately. Not looking for a relationship, but could be a friends with benefits if we vibe.

About me: Nerdy artsy type who loves movies. Nice titties and soft, average body. Light brown skin and dark eyes. Been told I'm cute and/or sexy. Down to exchange pics.

Please be 35+ y/o. I am very open to men or women or both ;) seeking something casual and possibly ongoing if we click!

Hello! I am a 29 y/o BBW wife whose husband works away a lot of weekends. We are very open and eager to find someone to keep me company 2 or 3 weekends/month. I am 420 friendly and love a girly cocktail :) in the bedroom I love to seek and explore all different kinds of fun. Particularly what I am very interested in lately is being filmed/photographed… I can travel to you or if we can meet for a drink first I’d love to see if I can convince you to follow me home ;) tell me what you like and what you’re looking for. Pics on my page.

Young fit couple here - looking for a guy to join us. Please be around our age (20-25) and be fit. We are (23m/21f), won’t respond to anyone outside of this age range.

PLEASE DM your age when messaging for a response. Hit us up, would love to find someone interested!

I’m a dominant woman looking for a submissive guy to use as my plaything… I want someone with lots of energy who’s eager to please and who will do whatever it takes to make me happy.

Imagine sitting on the sofa as come through the door, still all sweaty from the gym. I click my fingers signalling you to immediately crawl over to me and kneel at my feet… then I point towards my pussy signalling you to shove your face right up against me and start licking me through my gym shorts before I pull them down and command you to please me and lick up all my juices mixed with sweat.

hi hi

i’ll be staying in hyde park at the end of july for a conference, and im looking for someone to have fun/sex with in my hotel room. i would like to host and do not want to travel. you’ll also be getting free dinner/room service.

im particularly interested in hooking up with a japanese guy lol - i’m not sure why but the last two japanese guys i spoke to were very hot but very crazy. so hopefully this time im presented with more normal people (who are still hot btw - this is a requirement).

for more about me: im 4’11”, not white, and a US size 8-10. message if interested and if you meet the criteria.

39-year-old white guy, 6’175 lbs, just a regular guy looking to give a discreet blowjob or just a handjob.

no strings attached. I live near the South Loop, UIC, Columbia, IIT. Any straight/curious college guys horny?

hit me up !! I can host or your car

100% discreet and down low

i’m a bratty bbw who likes being treated like a fucktoy 😈 i like rough and passionate sex and chemistry is a must. self proclaimed size queen. i’m bored at home today resting after the holiday weekend. we can chill and have some fun

i have pics on my profile you can check out. please be willing and able to verify. i take my sexual health very seriously and you should too, please be able to send recent results. i’m 420 friendly and can host. have a soft spot for latinos

26 trans girl looking for straight daddies to please orally. I cannot host but can come to you within the city only. I’m also open to car play. Hit me up if you’re interested, pics are appreciated ;)

dear future husband,

i don't know where you are right now. it's late, so hopefully you're getting the rest you've been really needing this week. i've been missing you, even though we haven't met yet. maybe we have, in passing, like on the train, at harold washington library, maybe you got off the bus right when i was getting on, maybe you pressed an elevator button for me because my hands were full and we exchanged smiles, i don't know.

i'm still in chicago, i feel stuck here. i probably won't move for a while, maybe ever. maybe i won't need to because you're here already.

i'm not here to play any games (unless its together on steam or something co-op in person haha), i genuinely can't wait to start building something real and sincere, even if we meet on a silly subreddit full of sneaky links and temporary satisfaction. i'm tired of the almost-relationships, the mental gymnastics, and feeling like my love isn't reciprocated. i have too much to give! i'm not seeking perfection, just something consistent and honest. say what you mean, show up when you can, and keep me updated when things are feeling down and you just need a night to yourself. i need those too.

i'm the type of girl that remembers the little things, that makes custom gifts for every birthday and christmas; i'm artsy and have too much creative energy to know what to do with. i've dabbled in many mediums, but i have a deep love for painting and sculpture. i can't wait to share my passion with my future students and with you!

when i love something or someone, i love them hard. i'm very affectionate and love making people laugh! i love team fortress 2, left 4 dead 2, my cats, my family, making gaming content and editing videos into the wee hours of the night. i love late night walks and catching the sunset at the montrose bird sanctuary and montrose harbor. i love drawing people in charcoal out in public and appreciating their beauty (always too shy to show them haha); i love people watching and spending my nights gaming and creating. i will yap your ears off about my comic and all of my art, i hope you're ready ^-^

anyways, i hope you love LOTR as much as me. i can't wait to be cuddled up on the couch with some snacks while watching the extended version, falling asleep and waking up together groggy the morning after, trying to remember where in the movie we dozed off. i hope we meet in time to catch the hunt for gollum in theatres <3

i wonder what your favorite foods are, where you like to run off to when you need alone time, what books made you cry, what games make you lose track of time and lose sleep. i wonder what silly names you've thought of naming our future child/ren. i wonder what your family is like, and what they want me to paint for them.

i wonder where you've been all my life.

i've wrote you letters before, but they're tucked away in my journals from over the years. maybe this one will find you first?

love,

step

Ever wondered whether you can take a pornstar-length cock? I’m looking for you. I’m a true 8.5” and love to find women who’ve always been curious but never had the opportunity to get filled.

I can host in Lincoln Park, and love to start with a lot of slow foreplay so you can relax and get warmed up. I’m more than happy to verify with photos, but ask that you do the same. If you’re interested, please send me a chat and tell me what turns you on the most. Looking forward to it ;)

Starting late tonight all day tomorrow looking for guys into breeding kink guys our age and younger be hung into all holes being filled reply back with age and pic please

Looking for a guy 28+ around Chicago who's funny, easy to talk to, and enjoys a little playful flirting.
I'm petite, curvy, and single, looking for witty banter, good chemistry, and a conversation that might get a little spicy if we click. No pressure—just fun, genuine vibes.
If you're local, send me your age, your favorite late-night snack, and your best opening line. Bonus points if you can make me laugh before you make me blush. 😏