• Chicagoan 37

Latest listings

  • Casual Hotel Fun - m4t - 36 - Chicago IL

    Casual Hotel Fun - m4t - 36 - Chicago IL

    Men looking for Trans Chicago (Illinois) October 21, 2025

    Married man looking to get his cherry popped. Skinny bottom only please. If your in the Chicagoland area and looking for a fwb situation send a few pics, let's get coffee and figure out a hotel????

  • Casual Hotel Fun - m4c - 36 - Chicago IL

    Casual Hotel Fun - m4c - 36 - Chicago IL

    Men looking for Crossdressers Chicago (Illinois) October 21, 2025

    Looking for some occasional fun with a straight married man? Are you in the Chicagoland area? Are you skinny? If so, and you are interested, hit me up with a few pics and hopefully we can get a coffee and figure out what hotel we want to book lol.

  • Casual nsa/fwb - m4w - 37 - Chicago IL

    Casual nsa/fwb - m4w - 37 - Chicago IL

    Men looking for Women Chicago (Illinois) October 21, 2025

    Just like the title says. LOL Please send a picture or two if you're interested and please live in the Chicagoland area! I can travel. I don't discriminate on age, race Etc. Please be clean and let's both be respectful! Interested in average to skinn...

  • Casual Hotel Fun - m4w - 37 - Chicago IL

    Casual Hotel Fun - m4w - 37 - Chicago IL

    Men looking for Women Chicago (Illinois) October 20, 2025

    I am looking for a skinny girl that wants to have fun occasionally. Please live in the Chicagoland area! I'm not looking for multiple partners. I am white male, 37, 5'9. Athletic/Skinny build. I don't discriminate against Age,race,marital status ect....