r/chicagor4r

▲ 5 r/chicagor4r+3 crossposts

26 [T4M] #Andersonville - looking for jocks with BWC to please ;)

Trans girl looking to have some oral fun ;)

Looking for Jocks and twinks with BWC

Love to rim a nice bubble butt too

5’5 130 with excellent oral skills here.

I cannot host but I’m willing to travel if you’re not too far.

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u/deadbodylove — 13 hours ago

27 [F4M] #McKinleyPark - looking for someone to ruin my sleep schedule with movie marathons

I miss having someone to randomly message at night about a scene from a movie or an anime episode that completely destroyed me emotionally. I’m more of a stay-in type, so my perfect night is snacks, dim lights, something good playing, and someone fun to talk to during it.

I’m into psychological thrillers, comfort shows, late-night rewatches, and anime that somehow leaves you staring at the ceiling after the finale. Bonus points if you can recommend something underrated because I swear I’ve watched everything already.

Would rather talk to someone older and mature enough to actually hold a conversation. Tell me what show you’d force me to watch first. 23+ please.

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u/complexorum — 17 hours ago

29 [F4M] #LoganSquare - hangout buddy with benefits? inquire within.

Low pressure, good times, and maybe a little heat if the chemistry’s right. I’m into easy conversation, playful energy, cozy hangs, and people who know how to flirt without making things weird. Don’t be shy unless it’s the cute kind, I like confidence, good humor, and vibes that feel natural instead of forced. Just looking for something fun, comfortable, and worth looking forward to.

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u/sync19951 — 17 hours ago

27 [F4M] #TriTaylor - In search of a FWB to help me relieve my sore nipples

27 Black female, 5’7 midsize. My boobs and nipples have been so sore recently. When they get like this, I love having them caressed and sucked. Looking for someone my age or older with a strong preference to Black men and dark haired white men.

reddit.com

32 [F4M] #WestLoop - looking for a fun dinner date

I have a million restaurants saved that l've been wanting to check out & l'd love some company.

Ideally we meet up, take an edible (totally fine if that's not your thing), have a great meal & fun conversation, & then we go our separate ways.

*bonus points if we end up making out before saying goodnight*

You:
- mid 20s to late 30s
- a yapper
- great sense of humor
- always down to split dessert

Me:
- 5'3
- attractive (black, tattooed, & thick)
- love to get lost in a good conversation
- a married mom

Message me with a restaurant you've been dying to try out & let's swap pics if you're interested

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26 [F4M] #LoganSquare - wasian looking to worship the bwc of a nice man

i'm 26, wasian, 5'5, 120lbs with long dark hair and piercings. I'm into cnc and praise hehe

u: have a bwc ofc, are 23-33, bonus if u have tattoos, a mustache, and are VOCAL 😵‍💫

I cannot host + preference to ppl w/ pics in their profile!!

reddit.com

29 [F4M] #Loop - kinky, touch starved, and honestly looking for a fun hookup

honestly feeling pretty lonely lately and missing that kind of connection where you can flirt, tease, and slowly open up about your kinks without feeling judged. i’ve got a few fantasies sitting in the back of my mind just waiting for the right person.

reddit.com
u/rihito321 — 2 days ago

33 [f4m] #westtown - searching for a consistent fwb with an emphasis on the F

Hi! I’m 33, black, plus size and looking for an actual friend with those incredibly fun benefits. I love to read, cook, travel, watch sports and hang out with my corgi. I don’t necessarily want a serious relationship but also I do like consistent sex so … ¯\_(ツ)_/¯

I’m big on vibes!

I don’t have a type but please be older than 25 😅.

Let me know what you’re looking forward to this summer so I know you read this !

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u/19-throw-away — 3 days ago

31 [F4M] #LincolnPark - here comes warmer weather and open windows. Thoughtful, curious and patient dumbass seeking same, 28+.

I'm looking for an easygoing FWB that enjoys chatting and/or sexting throughout the day, consistent getting-togethering, and is receptive to trying new things and talking

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u/the-howdy-ist — 2 days ago

19 [F4M] #LOOP - smoke, cuddles, and someone fun to stay up with tonight 💨💕

honestly just looking for someone with good energy tonight. someone attractive, affectionate, funny, and easy to talk to. i miss late night conversations, smoking together, cuddling up, laughing at dumb stuff, flirting too much, and staying up way later than we should 😉

i’m really into warm vibes, playful teasing, good conversation, soft kisses, and people who naturally make me feel comfortable without trying too hard. confidence and humor always get my attention fast.

not looking for weird energy or dry conversations. i’d rather actually vibe first and let things happen naturally. maybe something ongoing if we really click 💋

420 friendly.

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u/JornoJovanna — 3 days ago

33 [F4M] #WestLoop - looking for new friends in the area.

Black slim thick. Looking to have a drink & see where the night takes us. Can be ongoing FWB if we vibe. Travel a lot for work & this seems easier than swipe sites. Can swap pics.

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u/Jarelle18 — 3 days ago

28 [F4M] #Edgewater - Trying this again because why not

It’s been months since I’ve entertained anything casual and I kind of miss it. I’m not here for promises or future plans. Just something simple, physical, and drama-free. If you’re respectful, discreet, and actually available, feel free to reach out.

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u/kookino — 3 days ago

36 [TF4M] #Loop - Trans Asian F Looking for Open Minded Guys

Exotic slim, very sexual but not slutty, I'm a dom top but sweet and soft. 5'6" trans Asian F traveling to Chicago looking for openminded guys. I like to have fun, am cheerful and chill.

Please tell me about yourself, height/age, send clothed pic or nude but not a d--k pic by itself. Please be fit, in good shape.

I will not reply to people who send one word message "wyd, hey, sup", who provide no info and pic.

I have a verified pic, I am real, I am dependable. I will request you to verify if we click.

I do not send nudes or face pics, please do not waste time trying to catfish me.

reddit.com
u/QueenOfEdging — 3 days ago

24 [T4R] #Bridgeport - trans boy looking to host in chinatown today

looking to host, not looking to travel. tell me what you're interested in doing together and we'll see, photos on my profile

i prefer a quick creampie. i let you in, you position me how you like, cum inside, leave

PLEASE dm me your age/sex/location and preferably a pic of body/face/dick or something. if you've messaged before hit me up again im looking for rn or anytime today

reddit.com
u/cumragsextoy — 3 days ago

36 [MF4M] #ForestGlen - My wife and I love letting people watch us have sex in person

This was a mutual fantasy that we had talked about for years before actually trying it. The idea really excited us both, and we would get the tingles and butterflies even when we discussed it. My wife was really shy and nervous about actually trying it though, so I just let her process it and work up the courage at her own pace. It was about five years later when she decided that she felt ready to take the leap and bring our fantasy to fruition. We got to know somebody online for about a month, then we invited him to our house. Her and I both enjoyed it immensely and absolutely love doing this now.

We are a couple who are deeply in love and have a very close bond, so our sex style is always intimate, romantic lovemaking. This is one thing we are always sure to initially make clear to anybody we are getting to know because we don't want the spectator to be someone who is looking for ultra-pornified, lascivious sensationalism; we want somebody who will appreciate witnessing the intimacy of a couple with a loving bond romantically making love.

One thing we really enjoy about this is the excitement it elicits in the both of us. We love that naughty, excited butterflies feeling that you get in your abdomen that you get when something is out of the ordinary and taboo; it's so thrilling to us how it makes our bodies quiver and tremble involuntarily. But at the same time, the whole scenario feels more wholesome than it does pervy or debauched because it's not pornified. It's like we get to experience the tenderness of making love while simultaneously enjoying the thrill of the taboo, naughty butterflies that make your abdomen feel like a cement mixer lol.

This is something that we want to do indefinitely. We would prefer to find a regular that we can cultivate a connection with because that would just make this whole thing even more special if it's someone who we could get to know and develop a social bond with. It would feel so special to be able to share our most sacred act of intimacy with someone who became a close friend of ours over time. I'm sure it will happen eventually if we just keep talking to people online.

I'm not sure what else to say about this, but if anyone is interested, feel free to DM us!

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u/_-_-_Mimps_-_-_ — 4 days ago

34 [F4M] #RogersPark - looking to meet this week, prefer tall guys

Hey guys, looking for someone to host. Moving to the south side and all my stuff is in boxes. Want to dip into the local talent while I’m still here up north.

I’m tall myself so I prefer taller men. But if you can get hard, then I won’t be picky. No strings attached, safety first.

Pics on my profile. If you don’t have a pic to share, don’t bother sending a message ok?

Some ppl wanna have conversations. I just wanna suck a nice dick and get fucked. Thanks in advance.

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u/godzilla_rocks — 4 days ago

29 [F4M] #Loop - Looking for Comfort, Connection & a Little Escape

Lately I’ve been craving a little comfort and stepping into a side of myself I don’t always show. Looking for people who get the appeal of slowing down, relaxing, and enjoying that carefree, cozy headspace. No pressure, no expectations, just chatting, sharing experiences, and seeing if the vibe clicks. If you’re local or just enjoy connecting with like-minded people who appreciate comfort, softness, and a little harmless escape… maybe we’ll get along better than we expect.

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u/Top_Entrance8144 — 4 days ago

26 [F4M] #McKinleyPark - Wanting a casual vibe that feels natural

Looking for someone reliable, respectful, and fun to spend time with. I like easy conversation, late-night hangs, and connections that don’t feel forced or overly serious. Must be local and drama-free.

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u/chanequeagentedelFBi — 4 days ago

25 [T4M] #logansquare - boy pussy looking to get railed

i love big dick and intense encounters. i’m pretty open minded to different connections but enjoy someone who is clean, in decent shape, and communicative. if that sounds like you let me know and let’s see if we connect

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u/Electronic-Koala-314 — 4 days ago

18 [F4M] #ChicagoLawn - jgh found this sub now i can stop being the only one entertaining myself lol

Whos down for a quick and meet? im more into older Chicago dudes who can handle a blonde woman like me, hopefully we can have a long term relationship or just be my fwb

reddit.com
u/Elodie_Wave — 4 days ago