Back seat of an SUV in the middle of the day in a pretty busy parking lot, the windows were tinted but definitely could of been darker.

Topped a guy at a rest stop bareback. Stranger in a public place unprotected. Was over taken by lust i guess. Im only curious and never thought id ever do anything like that. Was scared to death after and had myself checked. Was the singel hottest thing ive ever done.

Bending a mates wife over a sofa while he was asleep on it

Wow, such an amazing thing to happen. Wish this would happen to me.

My riskiest sex occurred at an adult bookstore with booths and glory holes. I had just finished sucking off my third cock when an older fellow came in my booth and begged to fuck me. I was so horned up I just dropped my shorts and bent over for him and was fucked bb. He came in about a minute flat and thanked me profusely. It was so intense and I lived the feeling of his warm cum oozing out afterwards.

Mfm with my gf while my friends gf was asleep in the other room

My girlfriend and I were on a long Greyhound bus ride. It was late evening and most people were probably sleeping. Well, we were caressing, and I was rubbing my hand inside her pants. She was nervous, so she reached into her travel bag, and brought out a blanket, to cover us. Where did that come from???? Anyway, she soon had my cock out and was stroking me as I fingered her. Yep, I got Jacked-Off on a Greyhound bus!!

I think the young couple across from us may have noticed, but they didn't complain as, when I looked over, the guy was busy, sucking on her breast.

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This is the type of risky sex I'm thinking and talking about.

Seriously though ....

3. Sex on a public beach after dark.
2. The bosses daughter at work while I was in HS.

And the number one risky sex ....

1. Sex on a public beach during the day and not having a clue who she was or using a condom.

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Porn theater. I let a guy fuck me unprotected and cum inside me. I was sitting on his lap and I was mostly just grinding his cock because we had no lube. It hurt a lot, and I saw from my tightie whities later that I also bled a bit. It didn't last very long. I came as I was sinking down on his cock. He came in literally less than 60 seconds.

That was almost 20 years ago. It was a pretty self-destructive time. I had bareback glory hole sex once, too, though I did have lube and didn't bleed.

The theater was risky for the obvious health reasons -- clean bill of health! -- but also for legal reasons because that was a time when undercover cops had no other crimes to address so they'd go catch the real criminals in porn theaters.