How Guys Lost Their Virginity

Welcome back to Guysourcing, where a panel of helpful gentlemen answer your questions. This week, guys responded to a reader’s request: “I want your ‘How and Why I Lost My Virginity’ stories.” Let the tales of deflowering begin!

Toe action

I was a good Christian kid. So as my middle-school friends grew into metalheads and acid freaks, I was still wearing matching sweatsuits and listening to Billy Joel. So I was shocked when this girl S. — in from California, purple hair, lip ring, giant Doc Martens—peeled out from my group of friends and chatted me up. Even better, she liked to sing Disney songs and sketch in her notebook, too. (She wanted to be an animator, although she ended up in the Navy.)

I worked up the courage to ask her out on a date, borrowing my best friend’s Pontiac Sunbird. We walked through the open lobby of big hotel, listened to “Lady in Red”, and ended up playing on a jungle gym in a secluded park. At midnight she kissed me and then — and I had forgotten about this until just now — sucked my toes. I do not know why.

We ended up on my friend’s bed. (He had left early that morning for work.) She let me inside her, where I immediately made a mess of myself, which she had the grace to ignore, telling me “Maybe we should wait until tomorrow.” A couple of nights later she let me try again and I comported myself more ably. She even told my friends later that I had given her her first orgasm, which, whether that was true or not, was perhaps the kindest thing that anyone has ever done for me.

LL Cool J

Well, as a homosexual, I have more than one story about how I lost my virginity. The first time I ever had sex with another guy it was only of the oral variety and he was one of my high school friends. We were really high and really horny (as 17 year-old high school boys are wont to be) and a little game of “you show me yours and I’ll show you mine” ended up with me sucking his dick, him getting off, and then quickly telling me not to ever tell anyone about it ever. The whole affair (this happened on a somewhat regular basis for several years) had that sweet mixture of triumph and shame that is the keystone to modern gay sexuality. I jerked off thinking about it every night. The first time I had anal sex on top was with some guy I met at a bar one night in college. It was over in about 30 seconds and I finally understood why everyone was always trying to get laid but had no clue what they were saying about condoms dulling the sensation. I mean, if being over in less than a minute was dull, I can’t imagine the alternative.

Finally, about a year later, I lost my bottom virginity, the most important of all, to an enormous guy who looked exactly like LL Cool J. It was the first time I’d been with the black man, the first time I’d seen a penis piercing, and the first time I let someone persuade me to do something I didn’t really want to. But I did, and it was great…and painful…and the only time where I felt like something monumental had happened to me. The next morning, as I stumbled out of his poorly furnished apartment and took the train back to my apartment, I felt like a new person, like I had finally seen and done it all, and that I could finally enter into the greater conversations about sex that were happening around me. I thought I had seen and done it all and that he really would call me like he promised. He wouldn’t, and boy, I certainly hadn’t.

Dick-pinching

I had been dating this girl who called herself “a reformed slut” for about a month. She was very vocal about how much she loved sex and how much she wanted to have it with me, but she also wanted to take things slowly. As a guy who was 23 and still a virgin, I was already very familiar with the concept of taking things slowly. Honestly, I was fine with it and willing to keep waiting because I enjoyed everything else we were doing, but I really just wanted her to stop calling herself a slut, reformed or otherwise.

For some reason, she would always make me stop whatever I was doing before she would come. So it probably should have been no surprise to me that when we woke up one morning and said she was ready to have sex, she wanted to have really brief sex like she knew I wasn’t going to last more than a minute. I said okay, but was certain that was ridiculous because about two weeks earlier I’d masturbated for three hours and only come once.

I put my penis in and was instantaneously seconds away from coming. So I pulled back out and started pinching my penis so I wouldn’t come so fast. She thought I looked odd crouched on my bed with my dick between my fingers and told me she wanted it back in. I conceded and came about two flops later. She obviously did not come again, but we cuddled a little and started our day.

I ended up breaking up with her less than a week later out of sheer frustration with how she would never let me satisfy her. It was definitely the wrong decision because I wasn’t entirely aware that was why (I told her I’d met someone else) and because it ended up making her feel like a slut again. I really should have just talked to her about how badly I wanted to give her orgasms, but instead I was a selfish kid—despite my age. I like to think now that I’m no longer a virgin I make better sexual decisions, but this all happened two years ago.

Bathroom encounter

I actually ended up marrying the woman I lost my virginity to — which is all aw and everything, though we did break up for two years before getting back together. It was pretty unexpected, actually. I hadn’t put a lot of thought into my virginity. I was dating a girl long distance, and was pretty bad at it. I was full of the stupid nihilistic arrogance of youth, you know? I was nineteen and alternating between visiting her in New York and staying up all night on Instant Messenger. You kids these days with your Skypes and your free long distance have it easy! When I visited, I would sleep in the same bed as the young lady in question, and her splitting the room with a roommate didn’t prevent us from making out a lot. One night, as we were making out, she whispered that she wanted to fuck me. I was a little recalcitrant — it was out of the blue & I was just really starting to like girls, but the cocktail of hormones and the sneaking suspicion that I might be falling in love pushed me over the edge. We snuck into the bathroom for the deed itself— one of the four roommate was deaf, so they had a large handicapped bathroom. We had sex on the floor and I’m happy to report that mutual orgasms were obtained. The path from there to getting married was long and winding, but still makes for a cute piece of trivia.

OJ

I lost my virginity my freshman year of college. I wanted the first time I had sex to be with someone important to me. Somehow I had the fortune and patience to make sure that it was.

I had a terrible crush on this girl for months before she became my girlfriend; and she was the first girl I ever told “I love you.”

I’m not sure if she ever specified it, but I knew that a Saturday evening early into our relationship was going to be the big night. Whatever information imparted to me was done so on a Monday, because I remember that evening I came down with a terrible cold. Not wanting to sneeze and cough all over my girlfriend the first time we had sex, I spent the week chugging gallons of orange juice and trying strange, homeopathic remedies. They didn’t work, but Saturday arrived and I don’t think I sneezed on her once. I remember she had sheets monogrammed with her initials and afterwards feeling a little creepy about having sex on something her parents had had monogrammed for her. Other than that, I felt awesome.

I’m fairly certain if cell phones had been in use, I would have texted my friends the news shortly after. But telling them had to wait until the following day.

Desert rescue

Considering that I was 22 years old, it may not make much sense to ask “why” I lost my virginity. That is like asking why a man stranded in the desert decided to drink the water that he miraculously discovered while crawling in the sand. In terms of the “how,” alcohol played a very helpful role, because I don’t think she and I would have had our first kiss if we hadn’t been drunk. Then as we grew more serious about each other, it was inevitable that I would get to have sex with her eventually, and it happened about a month after we started dating. Losing my virginity was like watching the hottest porn ever, but instead of having roughly 40% success at imagining that the porn guy is me, I had 100% success at imagining that the porn guy is me. It was every bit as wonderful as that first drink of water in the desert, and life has been great ever since. We stayed together, and now we’ve been married for two years.