With my girlfriend of several months. I was 17, she 16. It was amazing. For both of us. Ok, there were a few logistical problems at first, but once those were sorted out, I swear the world moved. (Yes, I mean more than normal. Allow me some romance!)
Seriously. It was the best night of my life so far. I wasn’t even thinking about loosing my virginity, just how to make it better for her. Seemed to work. 
On a beach, age 18, with a girl I’d just met a couple of hours earlier. We wound up dating (and having sex) for a few weeks before I broke it off.
I didn’t have sex again for 6 years after that.
Heh, Troy’s got it right, Daniel.
Wel since nobody here knows me in person, I can share this rather shamefull experience…
I was 17, drunk and ended up having sex at the local gay cruising park…
With a girl I had been dating for a few months, at her place. I had a terrible cold, complete with sore throat and lots of mucus excreting from various orifices. Plus, I was so drugged up on anti-histamines and painkillers I could barely get it up. And she was on her period.
The next week, though, after I got well…never gonna forget that week. I think we left the bedroom once?
In the reclined front seat of a borrowed Honda Civic (It was blue).
Just happy to get it over with. All crunched up. Couldn’t “grab-hold” on anything for leverage.
I thought I was being smart by putting newspaper under her ass so that “stuff” wouldn’t drip on my friends car seat.
Well, it being my first time (not hers) I just exploaded with about a half gallon of “stuff” and it, and her “stuff” came gushing out after it was over and the newspaper just got soaked and the print was running and it really was disgusting.
The worse part was that I wasn’t able to check the baseball scores afterward. ha
Age…let’s just say early teens, at her place while her folks were out
I was 10 or 11 and my friend and I went out into the woods of a local park and went at it. It wasn’t too bad, in retrospect, I just wish we knew about lube since this became a pretty common occurance. For what it is worth, the boy was the same age as me.
Okay, makes sense. Actually, a couple minutes after posting that, I realized maybe that’s what you meant. But I kinda like the idea that your first sexual encounter was with this crazy gender-switching alien.
Daniel
Junior year college, during a party, went back to my room to get a new party tape, saw a girl writing a note on neighbor’s (to the LEFT) door pad. Chatted in the hall, went into my room, sat on the couch, started making out, move to my roommate’s bed (I slept in a high loft and was not up to the challenge of THAT smooth transition), where we got going, then realized I had not shut the door all the way, much less locked it, as my roommate, Dave, started coming in. Yelled for him to stop, and kept at it. She was calling me “Dave” the whole time which was making me laugh, I mean, how do you correct someone in a situation like that? Got her name about a week later. Once more a few weeks later, then we quit. A month or two later I heard a very distinctive noise coming from the room of the neighbor to my RIGHT. She was working her way down the hallway!
Freshman year in college, with a guy I’d been dating for about 2 months. We did it on his grandma’s couch. It was actually really sweet for a first time, but I was really nervous and my body went kind of numb. I was glad I waited until I was in college.
Gardnerville
A Gay Bishop? Can’t beat that!
In a fraternity house with a guy I barely knew. Don’t remember hardly a thing about it…just waking up having no clue where I was or what happened to my clothes. Reason to believe I was drugged but that’s another story for another day.
Not a good experience. At all.
In her bedroom (we were both 17). Her parents were out of town and we knew they wouldn’t be back 'til the next morning.
We fixed each other dinner, had a glass of wine, played some music. The whole thing was wonderful. I’d redo it, just like that, in a heartbeat (come to think of it…we did.)
I’ve expressed this sentiment before, but I think that it is a little unfortunate to hear that so many first times take place when one or other is drunk or otherwise impaired. Also, the “well, let me get this overwith” sentiment is lost of me.
Hmmm…I was 19, in college, living in my first apartment. I’d been with my boyfriend about a year and a half, and really wanted to wait until I was married. He was very pushy, and kept blowing past boundaries we’d both agreed on. I let him talk me into it (he read me bible verses to convince me it was okay. Even though I had issues with his interpretation at the time, I let him talk me into it, because he got offended if ever I wasn’t as horny as he was. He took it as a personal insult. Refused to believe that I didn’t like being snuck up on and having my breasts grabbed, painfully). NOT an enjoyable experience. I cried afterward. Bastard.
But I was pretty stupid, too, for letting myself be manipulated.
I was 17 (20 days from turning 18) and she was 16. I did it with her in the back seat of my parents’ 1982 Ford Cougar. I was nervous and it took me awhile to climax. While I enjoyed the experience, i wish we had been in a more comfortable setting, such as on a bed.
I was 21; we had been a couple for about a month. We’d been fooling around but hadn’t gotten around to “the act,” and I finally decided that (1) I wanted to “get it over with,” and (2) I thought I’d be comfortable giving it up to this particular guy. It was the middle of the afternoon, on my bed in the house I was sharing with three other students.
Later I married him. Yes, I’m one of those boring people who has only had sex with one person. He had been with a few others, but his virginity had been starting to grow back . . . but I did have the pleasure of giving him a few “firsts” as well. And we’re still having fun. 
On her living room carpet, in front of the fire, with an older married woman I was in love with. No regrets, except that it didn’t happen until I was 21.
Just out of curiosity – do any of you think that an “abstinence only” form of sex education would have stopped you?
When I was a freshman in college, one of the first good friends I met was a guy named Jim. For a brief period, Jim dated a girl from the next dorm over named Shawny, but their relationship didn’t last very long, but they remained friends with each other and with me.
Shawny used to joke every time she saw me “I’m gonna take your virginity one of these days,” and I’d laugh and say “Yeah, whatever, I can’t wait. Har har har.”
Then, having finished all my finals at the end of that freshman year, I was in my dorm room, packing stuff up to leave in a couple days, when she strolled in. Her eyes were bloodshot and she smelled funny (I wouldn’t learn to recognize the smell of marijuana for some time, yet). “So, we gonna do this?” she asked, and not knowing what the hell she was talking about, I asked “Do what?” She reached out her hand and began a very nice, um, “massage” that made her intentions very clear.
Fast forward about 15 minutes, to the two of us laying quietly side-by-side in my bed. Shawny was the first to break the silence.
“Well, you lasted longer than Jim did his first time!”
And they say romance is dead…
Of course, it could’ve been worse – my second sexual experience landed me in the hospital…
June, this year (summer before Junior year of high school). With my then-boyfriend, in his bed. It was…okay…nothing great, but then, it was the first time for both of us.
CrazyMonkey, I want to hear about this hospital experience…