Winnetka IL
Age 18-100

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Men Seeking Couples in Winnetka IL – Real Personals — Page 2

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Jan 17, 2026

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33m. bull seeking ongoing fun. (Rogers Park) 33

Jan 06, 2026

European for fun (Ohare -north west suburbs-chicago area) 41

Dec 14, 2025

Nw burbs tonight only . i want to watch if you allow (Algonquin) 35

Dec 05, 2025

Looking for kike minded friends in the area (West Rogers) 33 Verified Premium

Nov 16, 2025

First mff. can you help? (Northside Chicago) 35 Verified

Nov 03, 2025

Please spank me until i beg. (NW Burbs) 55 Verified Premium

Are you a couple that are spanking affecionado's? (Des Plaines) 65 Verified Premium

Nov 02, 2025

Couple needed to administer domestic discipline (NW side) 55 Verified Premium

Oct 16, 2025

Free weekend for fun! (West burbs (but can come to the city)) 26

Oct 10, 2025

29 yo white, fit, and very endowed male looking to play today/tonight! (Albany Park/Travel to you) 28 Verified Premium

Oct 08, 2025

Dominant guy seeking submissive couple (North side) 36

Sep 28, 2025

Upscale bull for couples (chicago only) (west town) 36

Sep 24, 2025

Someone teach me please (Albany Park) 32

Sep 22, 2025

Buying a show - hosting today! (Skokie) 36 Verified

Sep 09, 2025

Mfm a fun night where everyone leaves with a smile (Arlington Heights) 67 Verified

Bi m vouyer or join in. can host you or travel today (Ravenswood or travel) 29

Aug 25, 2025

Fun bi guy, .looking for a open-minded couple or female (Chicago) 56 Verified Premium

Aug 22, 2025

Hung bull for hotwifes (Jefferson Park) 36

Aug 15, 2025

Wanted a kinky couple near park ridge for fun right now (Park Ridge) 48 Verified Premium

Aug 12, 2025

Seeking a submissive couple (Jeff Park) 58

Aug 06, 2025

Let’s play open minded and hung 9” here (Chicago) 55

Aug 05, 2025

Looking for someone to come with (Niles) 26

Aug 04, 2025

Handsome extremely hung 9” let’s do this (Chicago room or travel) 55

Jul 19, 2025

Voyeur here (Wheeling) 43

Jul 05, 2025

I’m looking to meet up with a couple and help them explore (West Loop) 50

3 some for late night (O’hare) 38 Verified

Jun 21, 2025

Buy wife’s panties (Winnetka) 35 Verified

Jun 19, 2025

I service your man while you watch (Chicago) 35

Jun 17, 2025

6’3” tall, black, packing – northside chicago (North) 25

Jun 13, 2025

My first time too! (North) 42

Jun 11, 2025

Me giving a bj while u wtach (northbrook area) 65

Jun 10, 2025

Any couples looking to host a hung guy during the day (Chicago) 36 Verified

Any couples looking to host a hung guy near schaumburg (Schaumburg) 36 Verified

Jun 03, 2025

Smooth bottom to be shared (Chicago) 28

Jun 01, 2025

Watch your husband top me (Rogers park) 28

May 09, 2025

Service me please (Chicago i travel to you) 55

You guys can service my 9” together (Chicago u host) 52

May 04, 2025

Fun for all of us switch here with a 9” to show (North shore to south shore and every where in between) 50

May 01, 2025

Handsome and hung to play with both of you (Chicago north shore to south shore) 52

Apr 26, 2025

Huge ping pongs (Lincoln square) 26

Apr 15, 2025

Can't stop thinking about sharing your spouse? (Andersonville) 35

Apr 08, 2025

Sissy husband, where are you? (west ridge) 37

Dirty talk (west ridge) 37

Apr 02, 2025

Hung muscular latino looking to be of service to a couple . (North Suburbs) 30

Mar 18, 2025

Need a place to play? like being watched? (Chicago) 34

Mar 17, 2025

Love to play with both open minded here (Chicago and surrounding area I’m mobile or can host) 55

Mar 06, 2025

Sub looking for a couple (skokie) 36

Mar 05, 2025

Let's take a shower/bath! (Albany Park) 37

Mar 03, 2025

Use my place - i want to watch (Lincoln square) 45

Mar 01, 2025

Looking to buy wife or gf panties (North Side) 34 Verified

Feb 15, 2025

Bisexual 23yo man looking to have fun with a couple (Rogers Park) 23

Feb 08, 2025

Looking to buy wife/gf panties now (Deerfield) 34 Verified

Jan 30, 2025

Fun with vibrating panties (Evanston) 36 Verified

Jan 01, 2025

Looking for older heavy-set couple july 4th, 5th, and 6th (West Ridge, Northside Chicago) 47

Dec 17, 2024

Who needs their bf or husband serviced? (NW burbs) 65 Verified Premium

Nov 14, 2024

Please spank me until i am begging you to stop (NW Burbs) 55 Verified Premium

Oct 28, 2024

Be the subject (Rogers Park, Edgewater, Andersonville) 49 Verified

Oct 18, 2024

Male looking woman (Jefferson park) 36

Male looking for woman or couple (Jefferson park) 36

Oct 05, 2024

Bull looking for a couple / hotwife for this weekend (Downtown) 25

Oct 04, 2024

Looking for two great mouths! (Lincolnwood) 36 Verified

Sep 20, 2024

Please spank me hard and long (Des Plaines) 50 Verified Premium

Sep 07, 2024

Anyone up to play!! (Near NW Burbs) 50

Jul 12, 2024

Laid back guy looking for some casual fun (Northside) 32

Erik

Hosting couple for pool fun (highland park) 55

Jul 08, 2024

Hosting big ones for the night! (Rogers Park) 31

Jun 26, 2024

Latino 27 m for mf cpl/singles (Albany Park) 27

Jun 22, 2024

Bi bwc for no drama fun (Glenview can Travel) 33

Jun 18, 2024

Fit navy vet with bbc in rogers park (Rogers Park) 30

Jun 08, 2024

Alpha male bwc for cuck couple (Chicago) 41

Jun 07, 2024

Indulging a fantasy - m4mw (Edgewater) 50

Apr 19, 2024

Looking to come in your wife’s panties (Morton Grove) 34 Verified

Apr 15, 2024

Older kink (O’Hare) 28

Normal average guy can host! (O’Hare) 28

Apr 12, 2024

Carplay now! (Skokie) 37 Verified

Looking for first time (Chicagoland) 40

Apr 01, 2024

Can host couples monday or tuesday night (Glenview) 50 Verified

Mar 31, 2024

Adventurer seeks hotwife (Edison Park) 37

Mar 21, 2024

Looking for a sexy couple (Lakeview) 31

Feb 28, 2024

M looking for a submissive m/f couple (North park) 34

Feb 24, 2024

Hung looking for similar (Rogers park) 29

Feb 01, 2024

Open minded guy looking for same in cpl (Northwest Chicago) 49

Jan 31, 2024

Looking for a sensual couple (Evanston) 31

Jan 21, 2024

30m - bi, submissive, and looking to serve a couple (Northside) 30

Jan 07, 2024

Hung eastern european (Edgewater) 34

Jan 06, 2024

Looking for a couple today/tonight (North of the city) 53 Verified

Jan 02, 2024

Cuckold fantasy? hung here for wife (Chicago) 29

Dec 25, 2023

Xmas stuffing (Edgewater) 34

Dec 19, 2023

Dominant hung eastern european (Edgewater) 34

Dec 16, 2023

Bwc bull available (North side) 33

Dec 10, 2023

Pool party or discreet host? (lincoln square) 40

Dec 08, 2023

Hung looking for another hung couple (Edgewater) 28

Dec 07, 2023

Tattooed bwc for couples (uptown, rogers park, edgewater, lakeview, evanston, skokie, niles) (Rogers Park) 32

Nov 26, 2023

Fat tool for straight mfm / hotwife (North Shore or anywhere) 52 Verified

Looking for straight mfm or hotwife (St. Augustine) 52 Verified

Nov 12, 2023

Attractive 6-1 well educated fit white guy with an mba looking for fun (Glenview) 47

Nov 03, 2023

Bbc looking for fun (Schaumburg) 27

Oct 30, 2023

A couple's pleasure is my ultimate goal (Jefferson PArk) 64

Oct 21, 2023

Three's a charm? visiting, in lincoln square area monday and tuesday (Lincoln Square) 55

Oct 17, 2023

Hotel by o’hare (Ohare) 37

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