I was 18. It was my last day of school. He was 22. He was my boyfriend of a year and a half. I walked home in the rain that day. Got to his house soaking wet. Changed into his clothes and he asked if I wanted to have sex. I jumped at the chance because for the last year I had been asking him if he wanted to. He was a virgin too and I think he was afraid. All I remember is it hurt sooo bad because he was very well endowed. I ruined his sheets too.
The first time was in the woods behind the house I’d grown up in. It had been my favorite spot since I was little, and I wanted it to be there.
I was 16, he was 17. He eventually talked me into it, even though I didn’t really care. I wound up giving in.
It had been the first time for him as well, and the sex was horrible, as is to be expected. But he didn’t make this assumption. He expected his penis to know what it was supposed to do all on its own accord…and of course it didn’t. He kept switching positions in half ditched effort to get it to “work,” not realizing the problem wasn’t with me or with the position, or even his penis, but with his lack of experience…which I was perfectly okay with, and had expected.
He got progressively more and more spastic, no matter how many times I told him it was supposed to be this way…how could it go any other? Neither of us had done it before. Eventually he just got dressed and went back to his car to see what time it was, leaving me naked on a blanket in the middle of the woods. He came lumbering back about five minutes later, told me he had to be somewhere soon, and took me home. He broke up with me two days later, because he wanted to be able to “see other people” [even though we were in a non-exclusive relationship–at my insistance. :rolleyes:].
So to answer your question, yes, I regret doing it there very much (almost as much as I regret having sex with him at all)…not because the place wasn’t memorable, but because I wrecked not only my first time by having it be with…him…but I wrecked my favorite place in the world by choosing to doing it there, because now I associate it with all that.
It was 1973, we were both 17 and had been dating for 2 years, and were very much in love. Her parents were out of town, so we had the house to ourselves. After a night out we went back to her place, and wound up in her bed.
I was incredibly nervous, and horny in the way only a 17-year-old virgin guy can be. I probably lasted all of three minutes, and it couldn’t have been very good for her, but she always told me it was.
I loved her every day of the next 13 years even though due to my stupidity, I got to spend only a little of that time with her. Even though it wasn’t the best experience ever (certainly not for her) I wouldn’t trade any of my time with her for anything.
I was 17. She was 23, the married sister of one of my best friends, and the mother of a baby boy. She was stunningly gorgeous, with a fabulous figure, despite having delivered a child less than a year ago. The fact that she was a dance teacher probably helped, in that regard. I was at the peak of one of my phases of muscular fitness, ripped and pumped to the point that my friends started calling me “the monster” (that was meant as a compliment).
My friend’s family owned a cabin on a lake in New Hampshire, and we spent a lot of time there, that summer. At the time, I wore a Speedo bathing suit, and I have a distinct memory of seeing the lady struggling to pick her jaw up off her well-formed chest, the first time she saw me walk out of the changing room wearing nothing but my Speedo. It was actually a little embarassing. Not because of her, but because of my friends, who were initially convinced I was “sucking in” my stomach, until I showed them the difference. But, I did notice her reaction, and secretly enjoyed that part of the experience, though I had no thought of anything being possible between us.
We got to be good friends, over that summer. Though still a virgin, I was otherwise relatively mature for my age. My mother had died, after a long battle with cancer, that spring, and she commented several times on how well she thought I was handling it. I didn’t own a car, at the time, so she would often drive me to and from NH. My friend didn’t own a car, either, and stayed in NH all summer, but she came back to Mass during the week, and went up on weekends. Oddly, her husband never went to NH. I don’t know if I ever knew, or cared, why, but I was glad of it. It made the long drive much more intimate.
At first, I thought she was just being friendly, and sympathetic about my situation. But, as we talked more, and got to really know one another, it became clear that there was more than just friendship involved. For my part, I was seriously in lust with her, before I ever got to know her. Over that summer, I fell in love with her. And, she with me. For her, also, it started as pure lust, but led beyond that.
We started sitting in her car, after she’d driven me home, just talking. One night, the talk turned to love and loneliness (mine) and, eventually relationships and sex. I was not good at talking about such things, at the time. My family never talked about those topics. Eventually, she couldn’t help but notice my state of arousal during such talks, and one night she reached over and started stroking my leg as we talked. Or, in my case, tried to talk. She asked if she could see my penis, and unzipped my shorts to release it, when I assented. A few gentle strokes, and a compliment I’ve never forgotten, later, it was in her mouth. She didn’t attempt to finish me off, that night, but it was still my first taste of heaven.
We started making out at every opportunity, after that night, until finally, one night, instead of sitting in her car, she came into my house after driving me home. We went to my bedroom, and made out for a long time. Eventually, we got fully undressed and made sweet, fabulous love. She came twice, which she told me was unusual for her. The only regrets I have about that night are that she insisted it be dark, because she was embarassed by the stretch marks she still had on her tummy, and that it never happened again.
We talked about getting married. She regretted having married the man she did. She said that, if she’d known what a cold heart he had, she never would have done so. But, she insisted we stop seeing each other, for a time, while she worked on getting out of her marriage. I was too young and stupid and scared of the prospect of being a stepfather, and facing my friend’s family with their knowledge of what we’d done, to handle that separation. I might have been able to face it, had we been together all that time, with her to reassure me. But, without that, and no one else I could talk to about it, I couldn’t handle it, and I haven’t seen her in a long, long time.
I regret that too, though I think I probably would never have been happy, if we had gotten married. But, I don’t regret the experience, even though it led to my first heartbreak. She taught me a lot; about love, about myself, about talking openly about intimate subjects, and about making love. She’s still a very fond memory, for me.
It stopped me.
You know, the one in between these two, where you do a ten-year prison term for attempted murder?
Where? His house. Upstairs bedroom. The usual.
Do I wish that it had been somewhere else? Well, yes, in that I wish it had been with somebody else, and I don’t think his housemates would have been good choices either.
I also really wish he hadn’t felt the need to read “The Rime of the Ancient Mariner” beforehand. Talk about ways to ruin a perfectly good poem for the rest of a person’s life.
I really enjoyed reading this thread. Not for the kink factor, mind you, but just reading all the circumstances in which people lost their virginity. I guess its fascinating from the prespective of a virgin (me). Its interesting to read how some people just had sex on a whim with virtual strangers, some people lost their virginity to prostitutes, some had horrible experiences, some had wonderful experiences.
While I have not actually had intercourse I’ve done other things, and probably passed up the chance to have sex on several occasions because I was too scared. In retrospect, I think I am glad I am still a virgin, since when the oppotunity to lose it did come along, I was certainly not emotionally ready for it.
I was 17 and a female co-worker was a having a party at her condo on a Saturday night. She was 21. (grin I can remember thinking; “She’s an OLDER woman!”)
I was actually surprised when she invited me to the party, and it didn’t occur to me that she had designs on me…until she asked me to stay after everyone else had left for the evening.
Ok, now to the embarrassing part…
I couldn’t… finish!
NO, not a problem with getting it up, a problem with getting off.
I was so nervous I was hard as two inch diameter steel re-bar, but I couldn’t relax enough to reach orgasm.
I didn’t realize this was a problem until she asked me: "are you EVER going to finish?! (I think with a hint of astonishment in her voice…but it might have been annoyance)
I actually faked an orgasm because I was afraid I was going to hurt her. I’m sure she saw right through that act…there was no mess.
I wonder if I am the only male that’s attempted to fake an orgasm?
I’ve faked a couple when it just wasn’t happening…in fact my second time (first time with protection, which probably had something to do with it) was one of them. And if you look at my sig you’ll have no trouble I hope in ascertaining my gender.
It’s successful enough if you keep the condom out of sight 
I’m sure you thought you had a point when you wrote this, but damned if I know what it was.
My girlfriend’s (at the time) bed in her dorm room.
I’ll never forget walking home that night, I felt like such a pimp.
Uh, you didn’t find it incredibly frustrating not to be “finished off”? Far as I’m concerned, once the snake is inside the tunnel, that’s a promise to finish much more sacred than marital vows.
In my bedroom, aged 17 with my boyfriend of the time. I would totally NOT do it again. (He dumped me a week later).
Faking orgasms? Isn’t that unethical, even for a male?
Never done that - but had trouble finishing as well. Just made sure my partner would tell me when/if she wanted to stop or got sore, and made a point of enjoying the journey. It’s possible to have a good time like this and even feel satisfied afterwards.
Trust is the key.
Some horrible slapper from my school, when I was 18, in someone’s attic at a party. It was a fairly grim experience, but I was delighted, though, because I was desperate to shag someone. I’d rather it would have been with someone I actually fancied, but any port in a storm…
Oh! That. Well, no. I was a virgin, remember? And, I mean a total virgin. I was used to being frustrated and having to “take things into my own hands”, so to speak. And, she was very sweet and apologetic about it, and I knew she was still having difficulties with the ethics of the situation. I was, too. So, no, I wasn’t any more frustrated when she stopped than I had been before she started. I was just thrilled and happy to have had the experience, such as it was.
Mine was on top of a shelter in Bushy Park in Dublin.
IIRC manwithaplan was off with another girl in the woods. We were very drunk and clueless but were going out with each other for a while so were quite comfortable with our collective ignorance. It was actually very funny. We (well I) had a great time and enjoyed every second of it not that there were a lot of them
Is that what you did last summer **Yojimbo ** ? 
Mine was with a fellow virgin on a hillside in the late afternoon gloom of an end of summer evening, a Sunday I think. And under a tree, actually I might be able to find the spot even now.
The hill overlooked the town we’d both grown up in and the cricket match in the foreground had just finished. Beyond the cricket ground lay the ancient spire of the church, and the town roofs peeked through the trees after that.
God, she’d had me like a demented maniac for months. Except she hadn’t ‘had’ me at all and there was no real expectation this hillside stroll would be any different to all the other half-cocked gropings.
But it was. I remember thinking ‘Blimey, it’s hot in here’ before there was an almighty whoosh and I pulled out. I can still remember the tingling starting in my toes before shooting up and, well, out. Like a bloody fire hose, it was.
I also remember the look in Sarah’s eyes. Very lovey-dovey. To be honest, I was more concerned about who might be hiding in the bushes behind. And the light drizzle that had just settled in.
25 years ago. Goodness. I wonder what became of her . . .
Mine was age 18, Christmas vacation, with my then-boyfriend, who I was absolutely crazy about and with whom I’d been carrying on a torrid long-distance romance since I’d left for college 800 miles from home three months before. We were on his livingroom floor, and it was the middle of the afternoon, which blew all my mom’s theories about curfews (I was home in time for dinner). He was (and still is) very sweet and patient, and it was a darn good thing that he was much more experienced than I was, although he was only a year older. We had been dating for about 6 months at the time, and we lasted until the following spring…I’ve never been able to get a halfway comprehensible explanation out of him regarding why he broke up with me, but he always says we were going in opposite directions (which I suppose was true; I was starting college, and he was working in an auto supply store).
It had almost been a couple of months before, when he came to visit me at school. It didn’t happen then only because he peeled me off of him, reasoning (correctly in hindsight) that it might have been fun then, but I would have been absolutely miserable, because he was leaving the next day and I wouldn’t see him for months after that.
More than 15 years later, he is married and lives 1200 miles away, but I still consider him a close friend and we talk about everything. I have absolutely no regrets. If it had been with the schmuck I dated before him, I would have had lots of regrets.