Stories of dating sex

Dating apps have given us unprecedented access to every nut job, borderline sociopath, and bunny boiler in Chicago, and having a nightmarish experience has become some sort of twisted rite of passage. We asked a handful of Chicagoans to share their worst online dating stories, and we were not disappointed.

“I’d matched with this guy on Tinder and we quickly discovered that we had a bunch of acquaintances in common, including some high school classmates and old coworkers.

Rarely, however, does one get to ask a sugar baby questions about the financial side of these arrangements.

Ahead, we chat with Crystal Milan*, a 32-year-old sugar baby on Arrangement.com, about what her job description is, what her relationships are like, and what she expects from her sugar daddies in return.

Bob's erection took on the consistency of Silly Putty.

He repositioned himself on my sheets, looked down, then up at me.

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Actually our sex was nothing out of the ordinary, but it helps us out.

After chatting for a couple of weeks, we decided to meet up at a bar.

Everything was going really well, until he got a few drinks in him and he began telling me obviously fake or exaggerated stories about how wealthy and successful he is, which was a huge turnoff.

Spending too much time on Tinder, Bumble, or Ok Cupid will make any sane person yearn for simpler times.

You know, like when singles met potential mates at corn husking bees or whatever.

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