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.

 

I sucked a guy on a plain on a night flight he was one of the cabin crew

 

My boyhood boyfriend and I from ages 8-13 would suck and in a later years fuck each other in the hollowed out centre of this bush that was just at the edge of a sidewalk on a busy road, trying to be as quiet as possible. In colder months (we lived in Niagara Falls Canada), we would do it behind my dad's car in the attached garage while my parents and brother were inside, or in my basement or his basement across the street while our families were upstairs. I envy that amazing, intimate relationship we had for all those years, remembering it with such fondness, because I so very much would love to find a special friend to share a relationship like that with again.

At 63, I'm still looking, and I'm so ready to have a full out gay relationship with another guy, with sex every day, and to find all kinds of crazy places outdoors and indoors to have it in. I'm really into having sex with another guy as much as possible and anywhere and everywhere: I just have to find a similarly willing fuck buddy or boyfriend to do this with.

 

But so far I've only had sex with guys in milder places. Once I was rimming this guy in his backyard hot tub in late evening, holding my breath while multiple times diving under to tonguefuck his hole (I could hold my breath for at least 2 minutes back then). I continued to see him and we also were sucking each other's cocks in the hot tub, before retiring to his bedroom.

Once I dove underwater multiple times to suck the cocks of this gay married couple in their backyard swimming pool, with other naked gay men in the pool and clothed guys in the backyard, at their annual Canada Day barbeque. The next year on Canada Day we had a threesome suck and fuck session together on their backyard patio after everyone had left the party. Another time a bunch of my gay friends and I went to a coed nudist resort, and ended up coupling up to have sex in a clearing in the woods under the bright sun.

I of course have also had tons and tons of sex with guys in regular places like in back rooms and patios of gay bars, bathhouses, gay sex clubs, straight porn theaters, gay porn theaters, gloryhole booths in video arcades, BDSM dungeons, in masturbation circle jerks, and, my favorite, in huge gay orgies, always with bi and gay men numbered between 30-50 hot guys.

But I can't wait to find crazier and crazier places, especially of the exhibitionist variety, to suck and fuck guys in. Bisexuality or homosexuality totally rocks, and should be celebrated anywhere and everywhere!

 

When I was in USAF tech school in Mississippi, I was dating this woman I'd met on the bus ride from Texas to Mississippi and we really clicked with each other. Come to find out that we were in the same classes so that made it easier for us to really get to know each other better. One night, we'd gone off base to an Italian restaurant where we had dinner - and then we went roller skating and I was surprised that she didn't know how to skate but we had fun just the same. As we were leaving the roller rink to head back on base, she said, "I don't want to go back just yet..." and I asked her where she wanted to go, my mind whirling because while it wasn't late, the only place still open was the bowling alley that was behind my dorm - but we usually met there, bowled, talked, stuff like that.

"Take me somewhere you can fuck me," she said. "I want your cock in me and I need it badly!"

On US military bases, there are few secluded places one can go to do stuff like this on-base - and we were on the wrong side of the base to take an easy walk to the motel. My mind is going 200 mph as we go through the gate to get back on base and as we walked, we both looked to our right and saw the thick stand of bushes and trees that lined that part of the base golf course and I remember being told that it was like that to keep golf balls from hitting the dorm (and it was my dorm). We both looked at that area, looked at each other, then turned to see where the gate guards were and... vanished into the thicket of greenery.

She practically ripped my clothes off and hers, too. Our lips locked, tongues exploring each other and she reached down between us and guided me into her. She was stupid wet and I slid in to the hilt. She gasped as I hit bottom in her and she said, "Keep kissing me because I'm a screamer..." Yeah, the last thing we both needed was the Sky Pigs to hear her and come investigate and we both get court-martialed. I was pounding the shit out of her and she moaned "loudly" against my mouth every time she had an orgasm.

I had to cum and I started to pull out but she grabbed my ass, dug her nails in, and held on until I couldn't hold it any longer and I came with a groan that I was sure the SPs at the gate would have heard. I could feel her using those wonderful pussy muscles to milk me; I was about to pull out but she wouldn't let go of me, so I gently moved against her until we both felt me get hard again inside of her and now on my second wind, man, I really laid the pipe to her. I came like maybe a half-hour later and we lay there on the ground gasping into the kiss until we kinda settled down.

I pulled out and we tried our best to get our shit back together; I peeked out of the area we were hiding in and saw that the coast was clear and we walked together and as if nothing had happened. We're both giddy over what we'd just done; she said, "I'm going to be walking funny for the next couple of days..." After that first time having sex, we'd go to the motel to get busy - that's when I learned that she was 100% against oral sex of any kind. For me - and someone who loves eating pussy - it was a bummer but by the time I'd slide into her, not being able to give her head left my mind as I could fuck her pussy and her ass.

We both graduated from tech school and she left to go back to her service station that also happened to be where she lived; I still had a few days to go and days that would find me fucking my squadron commander's wife...

But that's another story,..