No chance
Mine was also on my wedding night, just shy of 21 years old. It would be sweet except we divorced less than 2 years later. But I don’t regret waiting.
It was in the Hotel after the Wedding. He was also a Virgin and neither of us really knew what we were doing. I was crying out of pain, he kept apologising, I was also laughing at the bizzarness(?) of the situation. Let’s just say it was over quick!!
Here’s the amazing part. We had been dating for 3.5 years prior, and had not had sex!!!
It turns out (and yes I probably knew it at the time) I was gay. But what about him? He never pressured me… I haven’t seen him for 10 years, but the poor bastard is probably gay too.
Well I guess that worked out for everyone.
Should I mention he was a Baptist Minister?
:dubious: :dubious: :dubious: :dubious: :dubious:
At my friend’s house - two guys we’d met the previous summer came to town to party with us … I wanted to get the whole ‘virginity thing’ over with, and hooked up with one of them. Very unromantic, very awkward, and ultimately very disappointing for both of us. He was a few years older, very hot, and MUCH more experienced than I … I was so nervous, and just could not relax. Ultimately, I was so embarrassed at my lack of prowess that in the a.m. I hid my face in the pillow & feigned sleep until he left.
Funnily enough, a friend of mine hooked up with him a few years later and mentioned my name … he told her he’d always felt bad that it was such a disappointing experience for me, and that he was equally embarrassed the next day.
Which definitely made me feel better about the whole thing!
Age 25, at his house. It wasn’t great physically – ouch, ouch, ouch! – but it got better on subsequent occasions. I wasn’t expecting the first time to be great, I just wanted to go ahead and Do It and get the potential OUCH! part over with. We’d been together two months, so it’s not like we rushed into bed.
In a waterbed.
With the mayor’s daughter.
No, I’m not kidding.
** Airblairxxx ** Did you grow up in the town of Candor? 
For me it was 18, in the back of my 1968 Plymouth Fury.
The girl was a friend from high school. She had more experience and that night was an education.
::: sigh:::
I’d sure like to go back and relive that night again.
It happened a few months after I’d turned 17. My 21 year-old then-boyfriend & I decided to go to a local park & have a picnic, as it was a beautiful day. Well. We started making out in a semi-secluded area, then we made out a bit more. I was, coincidentally, wearing a skirt & we did have a blanket, sooooo… It was one of those “one thing led to another” things. I don’t regret it, though it was a bit of a blur. Makes for a good story. 
With my high school sweetheart, on the Fourth of July, in his bedroom, when I was 16, he was 15 and a half, he was also a virgin.
The sex was uncomfortable and unpleasant (for me), but the experience itself was romantic and memorable. I’m glad it was someone that I loved, and that loved me back.
OK, that’s just wrong.
My story?
Let me take you back to the warm summer of 1989. I was camping in the South of France (Frejus, for those in the know) with my parents. On the campsite, there was this discoteque. Well, really, it was a palm leaf roof with a dancefloor underneath, and a crappy stereo belting out all the latest summer tunes.
I was 16, Nathalie was 18, and French. We’d been kissing and fooling around for a few nights, when she didn’t stop at the usual goodnight kiss, and crawled into my tent. Right next to my parents’ caravan, I might add.
Being the suave guy that I am, I picked up on this subtle hint, and figured I’d better follow her. Now, this was a small tent, so undressing was a feat in itself. However, once all that was done, it was actually pretty good. Not the best sex I’ve ever had obviously, but not disasterous either. Of course, if you’d ask her, you might get a different answer - what the hell do 16 year old boys know about women, after all? It wasn’t her first time, that much I can tell now, in hindsight.
We hung out for the remainder of my holiday, and I think we exchanged maybe one or two letters after I went back to the cold North.
No regrets, though. She was the right girl at the right time.
CrazyMonkey, don’t leave us hanging with that hospital story there. Spill, dammit!
Dorm room. I’ll be there again next month, but I wish I could take it with me - I’ve had some good times with that mattress. Ah well. At least I get to keep the girl. 
Nah. It’d be fun to do it behind a waterfall or something, but it would’ve been inconvenient to say the least. I figure starting someplace standard leaves you room to work on more interesting locales.
Hmm… lets see.
Age 18, both of us. In her bedroom in her parents’ house. While her mother was probably in the house - she(the mother) didn’t mind, in fact, she probably thought it was sweet.
Both of us virgins - we waited until we couldn’t stand it anymore (I actually turned her down a couple of times, nervous about it) and it was quite a good experience since we were very much in love and both of us wanted it. Badly. So yeah, I’d do it again anytime.
And we don’t get that ‘abstinence only’ crap overhere so that’s hardly an issue.
Spill! Spill! Spill! Spill! Spill! Spill!
My first time was lovely… I was about a week away from my 18th birthday, and I’d been having a snailmail romance with a guy I’d met the previous summer. He was 21. I was on a school Drama class trip to the big city, Seattle, where he lived… he came and collected me at the Vance hotel where all us dramaqueers were staying… we rode Seattle city buses to get to his house – rather, his mom’s house, where he still lived. It wasn’t quite as awful as you’d think – she was a single mom and let him be a grownup at home. He was in college; acting school, the same place I eventually went, Cornish College of the Arts.
He made me dinner, including a salad made from veggies he was growing in the backyard, and a great salad dressing, a variation on Ohio Dressing from the Fannie Farmer cookbook ('cause he knew I was born in Ohio) – no alchohol as neither of us drank at all
it was a warm May evening; the window was open, the sun was going down
I knew I was ready for sex. I’d stopped being afraid of it about that time. He was utterly beautiful (an actor and a bike messenger! all muscles!) and I thought we were soulmates… we probably were, at the time.
He gave me a massage with oil scented with clove and vanilla
he had Peter Gabriel with Kate Bush on his tape player
It really couldn’t have been more perfect.
He was a lovely lover, patient and lusty and not nervous, so I wasn’t either.
We dated for the next year and a half. I would have married him if he’d have said “yes”. Now I am so glad he didn’t; we’re still friends, and still talk, but we would have been hating each other by now if we’d married (long (even more) boring story).
It was perfect. I was so glad I’d waited.
(He sent me a gift package including some of the clove and vanilla essence he’d had in the massage oil, and it arrived the day of my high-school graduation. I put some on and spent graduation in a hazy cloud of hormones. I don’t remember a thing about that day other than vivid images of the package.)
Sometimes I wish I could wrap up that beautiful thing and give it to folks like October and Aries28 and Kiki and Jessity. It’s not like I deserved it more.
Oh, and Baldwin, it wouldn’t have made any difference at all.
That’s got to be one of the sweetest things I’ve read on SDMB.
It was Christmas day, I was 18, and it was in his bedroom. I wouldn’t change a thing about it - we’re not together now but it was fun while it lasted. Besides, learned a lot of useful things for the next one!
No one has mentioned it yet but for me it was the girl next door. We were both 14. Her grandmother lived in a mobile home next door to her parents house. She asked me if I wanted to see the inside of her grandma’s house and as they say, the rest is history.
typical, the ngihts of the senior prom after the dance. back at my folks house, no the living room floor, with my folks in the next room asleep. it was ok, awkward, but ok, we were both vergins. a few weeks later, she went off to europe for an exchange program, her folks got divorced, and she came back all messed up. so we stopped dating. I left for the military, spent many a night crying her name in my beer. then I came out, and my first tiem there was with a guy I had met online who was about my same age, also coming out, si we both kinda explored together.
gee, guess you could say I lost my virginity both times to anohter virgin. not sure if he ever was with women, but I think he was.
as far as sex ed, guys in my school did not get sex ed, just the girls. strange hu? but if I had had sex ed, would not have made a difference.
I was 15 and she was 14.
First time was in her parent’s RV. It was pretty cool…the RV I mean. The sex was fantastic.
Ironic story…the girl and I were together for a couple of years until we had a nasty breakup and she hooked up with a friend of mine. About a year later my friend bought that RV from her folks. I don’t think she ever told him.
I was 17. It was with a prostitute. My best friend’s uncle took four of us during the summer between our junior and senior years to the whore house in neighboring Woodward, OK. The States Hotel. What a night.
E3
LOL! That was a Southern boy, right?
With a woman, I was 18, and it was in my bedroom in my parents’ house. Surprised the hell out of me, really, as I hadn’t realized she thought of me that way.
With a man, I was 30, and it was in his hotel room. Surprised the hell out of me, really, as while I had long known I could be a barroom pickup for a cute guitar player I hadn’t ever figured on said guitar player being a guy.