Freakiest person you've slept with

[thruster315]

What was the freakiest person you’ve slept with? What was it about them that made you look at them with mild disbelief? Was it something they said? Was it something they wore? Or was it something new that you had never done in bed before? Did they introduce you to something new and kinky?

I’ll let you define what you considered “freaky” and go from there.

And how did you move forward from that initial shock? Did you recoil from it? Or were you the good sport and try to go along with it?

The freakiest person I've ever slept with is myself. For some reason, I keep doing it.

[YeOldePerv]

Originally Posted by reclaimer

The freakiest person I've ever slept with is myself. For some reason, I keep doing it.

More common than you'd expect.

[Beef78]

Yrs ago used to fuck a pretty decent looking MILF in her 40s. I was like 28. She had a 19 yr old son and he liked to peek in, I'd be like whoa wtf and she'd say just keep going lol

[wsbfan1]

Not sure what everyone here considers "freaky" and not one woman, but back in the early 2000s I used to fuck A LOT of black chicks from those old AOL chatrooms. I could go into 'Black F seeking white M' rooms and pretty much get laid anytime. There were A LOT of black chicks who loved white guys in those rooms. I never had my cock n balls sucked more, my ass eaten willingly, fucked more asses or had more 3somes than when I used to cruise those rooms. Those chicks would do ANYTHING! A lot were married to black guys, others were single but they all loved to fuck and didn't act like princesses like a lot of white girls do. It was a lot of fun.

And it's not like I'm some super stud hung guy. I'm an average (in all ways) guy. But boy they loved me.

Originally Posted by Beef78

Yrs ago used to fuck a pretty decent looking MILF in her 40s. I was like 28. She had a 19 yr old son and he liked to peek in, I'd be like whoa wtf and she'd say just keep going lol

Your life sounds like a scene in a porno. I imagine when you left he went in and took his turn.

[ReclaimedMdT]

I was 19 or 20 and was seeing this girl who was studying mortuary science. At the time she was doing an internship with one of the local funeral homes. She asked if I wanted a tour of the place, you know the stuff you normally don’t see during your average visit. I naturally took her up on the tour. I basically saw the inner workings of the whole place. We of course ended up in the ”show room” where they keep the caskets, urns, and stuff like that. She casually brings up the idea of wanting to have sex in one of the caskets. I was young and figured why the hell not. I will say that some of those boxes are super plush, but don’t allow for a lot of room to move. It was awkward to say the least and I’m not ashamed to say that the setting definitely affected my performance in a negative way.

[SynchroDub]

Originally Posted by Beef78

Yrs ago used to fuck a pretty decent looking MILF in her 40s. I was like 28. She had a 19 yr old son and he liked to peek in, I'd be like whoa wtf and she'd say just keep going lol

'Da fuck, dude?
When I was 18 I dated a colleague who was in her 44s and had a daughter of 16, for nearly 2 and a half years.
Pretty petite gorgeous woman, and funny as fuck, even if she was just 4ft/9" (It just happened folks. It wasn't something I had planned on my agenda).

But we never had sex in front of her daughter or anything.
That is definitely not weird/freaky but fucked up, LOL.

[allworkboy]

3 years ago I had an affair with a hot Mexican lesbian who liked to get choked and called names while getting fucked and she also lick my balls which I didn't like. She is a lesbian, legally married to another equally hot Mexican lesbian. But she could fuck, gives the greatest BJ - no cover, had no limits. Every now and then she just needed a dick with no emotional attachment and I didn't have any to her, I just knew she was there to make me feel good and I was there to make her feel good. One time we did it for 5 hours straight and she only asked for a 5 minutes water break and another couple of minutes to go pee. I came 4 times in that 5 hours which is a record. Two is my most. She came maybe 10 times. She is a screamer too. Saying things like fuck me fuck me fuck me hard or I love the way you fuck me with that big dick of yours or I am your fucking slut, fuck me like one. We always meet in a hotel room, nice hotel, not some shady place, and I always worried the hotel management will come knock on the door telling us we are too lout - never happened luckyly. Or the time I got her a school girl outfit that said BJ University on it. Oh she surely earn her diploma that day. I still have a picture of her somewhere.

[Weanz]

Back in University, I was seeing a girl who was a bit on the bigger side but she had the best breasts I had ever seen/enjoyed! She loved sex, and was eager to do it everywhere: bathrooms, my car, on the beach, at a concert under a blanket, on the phone with her friends. She didn't care. Really different from the girls I had dated or normally date!

And it didn't stop after we broke up. Every so often, she would call me up to meet her for a "drink" to catch up; we always ended up in bed. One time she called me, drunk at a club, to beg for a ride home because her new boyfriend was a loser and didn't own a car. She promised it would be worth my time. When I got there, she came running out of the place pulling a smoking hot girl with her. Turned out, her idea of paying me back was a threesome with her friend! My first one... it was nuts.

No idea where she ended up... sometimes, I really miss her