In the bathroom of a local laundry mat. It was like 9 or 10 PM and no one was there when we went in. It was impossible to find a good position in a small bathroom when neither of us had done it before. We spent 15 or 20 minutes changing positions, and couldn't find one that worked for both of us. I popped her cherry so it was painful for her anyway we tried it so eventually, we gave up and got dressed. When we walked out, there was an older woman doing laundry, she stared at us with a grin as we quickly walked out.
A few weeks later, I brought her over to my friend's house after school, his parents were gone so we could do whatever. We hung out in the living room for a bit and then she wanted to talk to me alone so I took her to my friend's bedroom. He said, "Just don't fuck her on my bed." But, about five minutes later, I fucked her on his bed. We got naked, she laid on his bed, I put a condom on and climbed on top of her. She was wet as fuck and as soon as I put my cock in her, she started moaning. The bed was way better than that bathroom and it felt amazing. I only lasted 15 seconds or so, and blew a huge load balls deep inside her, filling the condom up. About ten minutes later, we both wanted to go again, but didn't have another condom. I looked around his room for one but didn't find one so we decided to fuck bareback. It felt even better this time and as soon as she started moaning, I started to cum. I pulled out just in time and shot it right on her pussy before she grabbed my dick and aimed it away. We laid there and talked for ten minutes before I got another raging boner and pulled her on top of me. I lasted about 30 seconds this time and nutted up in her as she rode me. She rode me for another minute or so before my friend barged in and busted us. He was pissed so we left and I walked her home.
I count both times as losing my virginity because I didn't cum the first time.

 

School yard against a wall.

 

My girlfriend's family (girlfriend at the time) was fairly well off. They had an immaculate horse barn and a tack room on the second level. We lost our virginity on a few horse blankets.

 

in my bedroom with a much older man.

 

My boyfriends bedroom while his parents were at work.

 

What engine was in that truck?

 

My anal virginity?

 

The first time I tried, at 16, I didn't even get my cock in before I 'shot my load' so I suppose that doesn't count.
The first time I did get it in, at 18, was on the 'specially prepared bed' of a 39 year old woman - after weeks of her 'training' me in the 'arts' of arousing a woman and in how to 'hold back'.

 

Cant remember. If I do, I will go back there to retrieve it.

 

No one forgets where they lost their virginity.

 

llllllllllllnext door niegbrors house her name was Teri. She was older than me a couple grades a head of me in school. Aolder girl who was the girl next door to

 

Under I95 in Philadelphia. The side walks block the view of people in cats, But every passing rig got a good show

 

MN extdoor neighbors daughter

 

My bedroom at home. Parents were away for the weekend. My gf came over and we got naked. Yeah, it was awkward, but very touching, because we really did care for each other. Lots of creative places and settings after that, but first time was sweet and fun.

 

Oral, in a car in a high school parking lot.
Vaginal, in a motel in Los Gatos, California.
Anal, in my BF's apartment when he was in college.

 

Wish I can remember where - would love to go back to retrieve it.

 

On a bed with a girl named Marnie. I wrote a story about it!

 

It was in the first class section of a trans Atlantic flight between London and NYC she was one of the flight attendants and about years older than me, blonde, slim, huge tits. She had just served me my umpteenth glass of champagne and noticed my massive hard one poking through my Chinos. She asked if she could help with relieving the strain.

 

Back of my buddies van, my friends were all watching me fuck some random chick as we drove down the freeway, good times!!