The craziest place you had sex with a man ?

That's crazy doing a 69 while driving! It's hot thinking about it, but only because nobody got hurt.
I did jerk off once in my mid twenties on a long road trip at night on an empty interstate. Somehow sitting for so long (and being young) got me erect. I had napkins to catch my cum and clean up, but realized right after that it was reckless of me to do that. If I had to avoid something when I was near the point of no return, I don't think I could've safely done so because of worrying about catching my cum and not making a mess over my shorts.
To be young and stupid I guess? LoL!

 

Yes, it was crazy. It only worked because he was short and nimble. And you'd think that would be enough, but, no. It was so hot that I had to try it with a girlfriend. She and I did 69. It wasn't spontaneous like it was with the guy so I had a chance to get my pants just past my hips to get my dick out and she managed to get in position, though much more gracefully than the dude did.
We drove like that for a short distance, got seen by a couple other drivers before she got nervous and climbed off to finish me off with basic road head.
That was the last time I went that route.
Comparing the two, it was sexier with the guy just because of how it happened organically and the extra thrill of being seen publicly doing gay stuff.

 

This may not be too crazy by many standards, but it was for me. A lawyer I worked with occaisionally had invited me to have lunch. He is a gay top and had flirted and made passes at me for years. Even before I had admitted that I was bi. So, on this day, he picks me up for lunch outside my office. We talk about a couple of nearby dining options. As we are deciding, he is seriously testing my waters- asking about my likes/dislikes and experiences. He shares some of his. As we are driving, he leans over and lays his hand on my thigh...and then he starts sliding it up my leg until his fingers find my cock getting hard underneath my suit pants. He comments how nice I feel and asks if I like what he is doing. I do. I then reach over and slid my hand up his thigh until I found his cock. He smiles and says he has a better idea. Next thing I know, we are at this hidden park in a residential neighborhood. He parks and proceeds to massage and gently squeeze my cock. He then leans over, slides his other hand behind my head and pulls me towards him and he kisses me hungrily. We make out for a bit and then we break. He reached down and unbuttoned his suit pants, took my hand and slid it under the waistband if his underwear...and tells me to oull him out. Which, I did. I then started stroking him while we kissed again. He then suggested that I suck him. I was so turned on, I just went with it. He slid his seat back and directed my head down over his cock. I hadn't sucked a cock in years and was soooo turned on. I enjoyed him every way I could, and judging from his moans and the pressure variations of his hand on the back of my head, it was working. Eventually, he tells me he is getting ready to cum, I redouble my efforts and he unloads in my mouth.
Afterwards, I sit up and become instantly aware of a couple of things- first, we were in a residential neighborhood, at lunch time....and ...that this park was where all the lunch runners from work ran around. I immediately saw several people I worked with. Thank goodness my friend had the windows of his har limo-tinted, so I don't think anyone saw us or recognized me. Of course, I ran into ALL of them later at work. But I couldn't detect any strange looks or vibes. Whew!

 

Wow.

When I have sex I need to be completely naked. Even in an ABS video room. Just gets me up.

Car sex? Not for me.

 

Staircase (three different friends), gym office, car seats, table. My excuse is that I was young.

 

On a hill behind the farm I own is a fire tower. It's about 100 feet high. The work area was locked, so he fucked me on the last platform. Anyone could have seen us as there was a picnic and viewing area below us. As hard as he was fucking me, I think we made the tower rock slightly.