r/chicagor4r

▲ 7 r/chicagor4r+1 crossposts

29 [M4M] #Clearing - Horny Latino here looking for jerk buds Let's edge and cum together.

Hello. I've been jerking and edging my cock and would love to find someone else to jerk with. Love masturbating, love porn, gooning, love to get my hard cock wet and oily. Tell me what makes you horny let's masturbate to it. Let's get some lube and lube up our hard dicks. Looking to relax, get naked and masturbate together, open to giving each other a hand and maybe more. Let's build some big loads together.

Latino 29yrs old, very clean and disease free. Very discreet. 5'7, 160lb. Uncut cock Midway - oak lawn area. Can travel. Sissies, femboys, cross dressers, ftm, straight-curious guys are a huge plus. If you have Snapchat let's talk there.

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u/throwawayy773 — 4 hours ago

29 [T4M] #WestLoop - Want to try topping a cross-dresser like me?

Hey there. I'm looking to explore my kinkier side a bit and cross-dress for a guy. It's still a (relatively) new thing for me, but I'd like to think I pull it off decently (see my profile). Haha.

 

I'm looking for some foreplay, oral, and to get fucked. But I'm also open to kinks and trying out most things in between. For example, I do have some play handcuffs. Haha.

 

I'm 5'7, 160lbs, 75% white / 25% Asian, and completely clean of drugs and diseases. I will admit since I'm still getting comfortable with dressing up, I would prefer to host at my place in West Loop rather than travel.

 

Hope to hear from (and get pounded by) you! My only request is that if you reply, please just include some descriptors about you and whether you can travel (similar to what I did) just so we have a good baseline. Thanks!

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u/MDvirgin — 1 hour ago
▲ 3 r/chicagor4r+1 crossposts

26 [M4M] #LoganSquare - looking to chat with married taken men who are curious or neglected sexually at home

Want to chat or meet with bi-curious or horny taken men. Bi guy here too. If you're horny, your wife/girlfriend doesn't take care of you, you want to explore, or just chat hmu. On Snapchat, discord, or here.

Dm with pics and stats

BWC++ uncut++ corporate++ blue collar++

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u/Express_Mission_5971 — 2 hours ago

26 [M4F] #LittleItaly - lf a new fwb or onetime hookup. Bwc fit

Lf a fwb or hookup kinda want something consistent im 420 friendly, can host, can drive. Always down to chill an have fun after work hours 5ish and weekends fun time anytime hmu let’s chat. What’s ur favorite go to spot in Chicago?

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u/Immediate_Branch_255 — 20 minutes ago

27 [M4M] #SouthShore - Any masc tops want a stay at home soft bottom?

I am seeking a masc top that's open to a stay-at-home soft bottom boyfriend or a long term relationship. Please be serious and open to connect.

I'm a black chub, around 5'7, a soft bottom that prefers to give oral over anal, and not really hairy. I also have nice lips and a really nice body. I'm pretty sweet and like to please my top. I don't have much sexual experience, so hopefully that isn't an issue.

I'd want you to be single, masc, at least 20, preferably skinny or muscular but I'm open to chubby. I'd want you to have a really nice dick for me to make love to eventually and I'm not against being sexual as I do like it!

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u/highdepths25 — 3 hours ago

23 [M4F] #RiverNorth - Looking for some fun times with someone

Hey, I am looking for someone to have fun with. I am a 6'1 Latino M who is pretty chill and open-minded. I am honestly down for anything and kinda new to this r4r thing. I do promise a good time together, and like to give a lot. Not looking for anyone specific. Am open to couples, foursomes and more too. Also kinda curious about t-girls.

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u/Mysterious_Tap_4547 — 2 hours ago

28 [m4m] #Lakeview - Looking for Men to stop by my GloryHole

Swing by and get that dick sucked. No reciprocation needed. Fully discreet with an eager throat hungry to milk every drop from your full balls. DL/Straight/Bi guys are encouraged. Hairy and thick cocks to the front of the line. Come get milked behind your gfs back.

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u/Overall_Crew_9590 — 4 hours ago

43 [M4F] #GarfieldRidge - looking to have drinks and chill or more

Family ditched me and went on spring break. I have nothing to do and no one to hang out with. Let’s grab some drinks on me. And see where the night takes us

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u/OverSeaworthiness286 — 2 hours ago

33 [M4F] #WestLoop - blk male w/ bbc looking for FWB

33m here chill & fun personality. I live by myself in west loop and can host. I’m told I’m very handsome with a nice dick that goes deep. I enjoy being sensual but also like being rough if you can handle it. Hmu if you’re in or near the city looking for fun or a fwb. I have pics and vids as well.

Please no men, trans or couples inquiring if I’m bi, I’m not. Females only please. Would love to meetup soon I’m horny af.

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u/Fine_Caregiver_5067 — 2 hours ago

28 [M4M] #LakeView - Looking for JO Bud ongoing/one time thing

New to this looking for someone 25-35. I am DL and looking for someone who might also be in a relationship/married that gets the need to be discreet.

Located in lakeview. Want to chat first to see if we have a connection then move on from there. Open to JO, mutual JO, and exploring from there if that’s what you’re about. Ideally would love a situation where we can chill, have the game on, and stroke.

Can’t host all the time but willing to travel/see what we can make work.

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u/Accomplished-Dog7195 — 3 hours ago

30 [F4M] #LoganSquare - looking for something real and consistent

Hi all. New here so be gentle with me :)

I’m looking to make a real connection with somebody who would consider themselves dominant and is looking for more than just a one time thing. I’m open to FWB or a serious relationship if we click.

Me: I’m a working professional with a 9-5, workout often, love to be creative, love to be outdoors/go camping in the summer, reading, movies, and music. I just got a bike and I’m very excited to ride around this summer. I’m on the shorter side, more athletic build so not super skinny (soccer legs for life 🙃), I have some tattoos, lean a little more alt/emo but overall I’m just a little weirdo but a lot of fun. Sexually, I’m submissive and love to turn my brain off during sex.

You: Preferably you are also a working professional, in their early to mid 30s, enjoy some of the same hobbies as me, silly and like to take the lead. Alt/indie/skater boys to the front :)

I’m looking for somebody who I can grab a drink with, watch a movie, just hang out with but also explore sexually with.

Sound like you? Feel free to reach out. Please tell me about yourself, what you’re looking for and your favorite Chicago restaurant so I know you’re actually interested.

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u/OptimalAir8251 — 22 hours ago

40 [M4FM] #Loop - Cum hard while I rim both of you

I enjoy rimming both parts of a couple while they cum. OK, now that I've got that out of the way....

Im 40, white, in shape, and love helping both parts of a couple cum. Something enjoyable about exploring you both, helping raise the temperature, and finding new ways to make your eyes roll back in your head while you cum. Very bi. Love to rim, love to lick both of you clean after you finish. 69ing aficionado. No more fulfilling experience than licking a freshly filled pussy clean.

You: be horny. Enjoy bringing a very bi guy into the mix. Be able to articulate the unfulfilled fantasies, or scenarios you enjoy. Enjoy being rimmed (or have fantasized about it at least!)

Goals: love rimming. Both of you. Especially enjoy my tongue buried in your ass while you cum. So let me rim him and play with his balls while he cums in her. And then lick her clean. And then rim her endlessly. Open to whatever other kinky scenarios you can imagine.

You host, during week, early mornings or midday.

Let me be your toy. Cum hard on my tongue.

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u/HolidayPapaya — 14 hours ago

25 [T4M] #logansquare - looking for dominant dick asap

ftm man looking for rough dominant dick. i enjoy a masculine guy and someone in shape. i love big dick but how you use it is more important. i’m kinky and into a lot of different things. what do you think?

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u/Electronic-Koala-314 — 15 hours ago

26 [m4f] #Bronzeville - British Bull ready to breed some Easter bunnies

Lets flirty chat and have some spicy convos.

Posted a few time here had one success hoping to make it a second. Been honry af recently and just need my balls drained.

Looking for something casual but spicy. That kind of hot flirty relationship that gets your heart beating and the mood going. I do tend to have alot of stamina so hopefully you girls can go few rounds. I have a few kinks and the one that realy get me going is breeding something so primal about it...

If you want to know and are interested hmu. I dont do telegram

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u/Dr_p0stman — 5 hours ago

30 [F4M] #RiverNorth - Pretty Latina Looking for AP April 14-16

Looking for a drug & disease free affair partner, who is also in a similar situation, for ongoing hotel room (or outside) meetups when I'm in town.

I'm pretty, in-shape, curvy, work in corporate, & have a sense of humor. I like working out, traveling, anything outside and having fun.

Would love it if you're at least 28, kinky, take care of yourself and have a good personality.

Can't wait to hear from you 💝

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u/Fun_Amphibian1341 — 19 hours ago

36 [M4F] #Loop - discreet, daytime connection in loop or lakeview

I will be straightforward, because I respect honesty.

I'm 36, Asian, married with kids, working a corporate job in the Chicago Loop. My life looks stable on the outside, but my marriage has been emotionally and physically disconnected for over a year. I'm not here to change my family situation. I'm here because I genuinely miss connection, desire, and being close to someone who feels the same.

About me: confident, calm, and self-aware. I take care of myself, communicate well, and know how to make a woman feel seen and wanted without pressure or chaos. I work downtown and have flexibility. Lunch dates, coffee, long walks, or stepping away from the office during the workday are all possible. Discretion is natural to me, not something I have to force.

What I am looking for: a woman who understands complexity. Someone who may also feel lonely, touch-starved, or emotionally unfulfilled. I'm not looking for drama, secrecy games, or guilt-driven interactions. I want something private, mutual, and honest where emotional comfort and physical desire exist together. Chemistry matters. Desire matters. I'm especially drawn to women who still feel a strong physical need and aren't afraid to admit it.

If you miss being desired, being touched, and having someone who listens and wants you (without trying to take over your life), we might understand each other very well.

Message me if this resonates. Tell me what you are missing

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u/pppbruce — 16 hours ago
▲ 3 r/chicagor4r+1 crossposts

23 [mm4f] #lakeview - two friends looking for a girl to pleasure together

Ever fantasized about being tag teamed by two best friends? Well todays your lucky day

Me and my buddy have been joking about having a 3some for the longest time now and thought fuck it, we’re both single, let’s try to actually make it happen. So we’re looking for a gal! About us: we’re 22 (him), 23 (me), both recent college grads, respectful, in shape, very sex positive (and experienced)

What we’re looking for: someone around our age who is sexually confident, open minded or knows exactly what it is that she likes and doesn’t like so we can make it our mission of pleasuring her.

If you’re interested or just toying with the idea in your head, message me and let’s see if we vibe, good vibes are necessary cause this is supposed to be a fun time. DM me on here

Verification over smap on both ends necessary, plz if you’re a spam account or catfish don’t waste your time get a life.

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u/Frosty-Ad7615 — 1 day ago

22 [M4F] #lincolnpark - looking for something casual

I’m a 22m fit/skinny who is looking for someone in the area to have something fun and casual. Not looking for anything serious, not picky, let’s talk and see if we click!

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u/Rosas24 — 19 hours ago

43 [F4M] #Roscoevillage - looking for a consistent partner in the city.

Looking for something consistent —

I'm a little shy at first but also outgoing, kind, and the kind of funny that sneaks up on you (yes, sarcasm is my love language). I stay active — whether it's a walk, a workout, or just moving through life with intention, I'm always up for it.

I've have a stable job, a good head on my shoulders,

I love to cook — real meals, with music on and a glass of something in hand. If you're lucky, I'll cook for you eventually. 😏

Friday night ritual: it's my time to decompress and recharge. Saturdays though? Wide open.

What I'm looking for: a man who shows up. Consistently. Someone who means what he says, communicates like an adult, and actually wants something real.

If you're just here for a good time and gone by morning — I'm not your person. But if you're looking for someone to build something with? Hi. 👋

Please don’t dm me if you are under 40 and or have 5 kids. :)

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u/drunkenzoodle — 20 hours ago

32 [m4f] #edgewater - at your service for one sided oral pleasure!

If you're in need of a release but don't want to go through that whole process of a whole ass hookup, look no further!

I love giving head, it's genuinely so fun. At the risk of sounding like I'm bragging too much- I'm pretty good at it too. Let my tongue and slender hands be of use to you as much as you need! no reciprocation needed nor is it expected.

I currently cant host but I'm mobile. If you cant either, we can work out another solution! we can chat for a bit, grab coffee, and hang out first too. comfortability and a safe and sexy space for both of us is my priority above all else.

otherwise, I'm really easy going, and love to keep the vibe light. I appreciate someone who can match that!

looking forward to hearing from you!

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u/cloud5739 — 17 hours ago
Week