My First Time

Male • 26 • Massachusetts

I was on a second date with a girl who I found rather attractive, and she had a proposal. "Let's play the sexual partners game." Despite not knowing what that game consisted of, as a twenty-six-year-old virgin (long story), I assumed it wasn't going to produce a favorable outcome.

"What is that?" I asked, not masking the fact that I didn't really want to hear the answer.

"You have to guess how many people the other person has slept with. The closer guess wins." She made it sound so simple. "You go first."

My competitive nature precludes from me turning down any challenge I think I can win, even if it means embarrassing myself in the process. I took a good look at this petite twenty-four-year-old blonde sitting across from me, and tried to imagine how many guys had been inside her. I had few clues about her past, but I did know she was a fairly devout Catholic. I couldn't decide if that would make her more or less promiscuous, but I decided to err well on the side of caution: "Hmmm, I'll go with five. Your turn."

I didn't realize it at the time, but she was working me over. This was not a game, but an elaborate setup.

She began to look at me like I was a jigsaw puzzle or an Escher lithograph. I would later discover that she had an uncanny ability to read men — accurately estimating their net worth and endowment in mere seconds. I didn't realize it at the time, but she was working me over. This was not a game, but an elaborate setup.

"I'm going to say seven," she held out the last syllable, coyly reading my reaction.

My acute sense of comedic timing acted up. "Close. Only off by seven."

She feigned shock. "You've been with fourteen girls! I'm impressed." (She wasn't.)

"Actually," I said, "I've been with zero." Lying about being a virgin was something I had vaguely considered in the past, but she'd caught me off-guard. In this case, it seemed the truth had worked in my favor. I had passed the elaborate test.

"Wow, I'm really impressed you would admit to that." The words seemed genuine. "I think it's great that you're a virgin," she said. She was laughing slightly, but it didn't seem directed at me. "I've only ever been with one guy, and I really don't have much respect for people who sleep around."

If she was simply trying to make me feel better, it was unnecessary. Victory was at hand. "So, I win? I was only off by four!" I raised my arms in mock triumph.

"You're so innocent and naive. It's really cute." She was glowing. "I'm going to enjoy corrupting you."

Over the next few weeks she did her best to tease and test me, enjoying every second of my reactions to her games. She told me that she was going to take my virginity, but she gave mixed signals on when and how that would actually happen. The culmination of the teasing came when we were naked in a whirlpool tub. She told me we weren't going to have sex for another month, and then spent about two hours grinding on me in the steamy, bubbly water. I enjoyed it too much to be pissed off.

The next day, I decided that I needed to take control of the situation. I suspected that she had really wanted me to take control the previous night in the tub, despite her verbal misdirection. So as we sat on her couch watching the History Channel (sexy, I know). I started slowly inching my hand into her pants. I was particularly proud of the pace and subtlety of my execution. She put up no resistance, and was soon cooing and breathing softly against my face. Meanwhile, George Washington was crossing the Delaware.

She took some initiative and started returning the favor. She unbuckled my belt, and, in a matter of a few minutes, was going down on me. The sensation was indescribable, but I was afraid that I wasn't going to be able to get off from it. This made me try harder to focus on getting off, which, of course, is counterproductive. Fort Ticonderoga was slowly falling to the British.

I was dead-set on ending my twenty-six-year drought.

After a few minutes, I said she could stop because it wasn't going to do anything for me. She said that's not why she was doing it, and, in what seemed like one fluid motion, yanked her jeans off and got on her back. I slid off her panties and she wrapped her legs around me, stared submissively into my eyes, and didn't say another word. Benedict Arnold's treacherous plans were brought to light.

At this point, I was giddy with adrenaline and testosterone, but I managed to keep a look of steely resolve on my face. I was dead-set on ending my twenty-six-year drought. I tossed my shirt across the room, and without stopping to think, took the plunge. I really had no idea what to expect, but needless to say, it felt incredible. All of my life I'd assumed I would last about seventeen seconds my first time, but to my surprise, I made it a solid four or five minutes. After waging war for years, the British were surrounded, and forced to accept defeat to this new, emerging nation. We came, nearly in unison. It was glorious.

We collapsed in a heap of sweat, ecstasy, and joyous laughter. She had exacted her revenge against the nameless guy who took her virginity and broke her heart, by taking my virginity (and a few months later, breaking my heart), and I had achieved my longstanding goal of having sex (with a hot chick, nonetheless).

Forty-five minutes later, we were at the local pharmacy buying the morning-after pill. I can only imagine what was on the TV at that point.


We're looking for stories about the first time you had sex. Email with 500-1000 words. (Don't worry, we won't print your name — but please do make sure to include your gender, where you were, and how old you were.) Submissions may be edited.
According to just about every pre-college advice manual, floorcest is a bad idea.
"So no, I didn't lose my virginity in the most traditional way."
"He looked like if Ian Somerhalder and Gerard Butler had somehow created a baby."

Commentarium (54 Comments)

Sep 27 11 - 12:17am

This is uh, pretty nice.

Sep 27 11 - 1:40am

Gross, use a condom.

Sep 27 11 - 2:48am

Throwing in references to the American Revolution was nice. I like.

Sep 27 11 - 5:47am

Glorious. Virtual high five! So nice to hear there were others who didn't loose it at 15 :) Way to not freak out under the pressure, unlike myself, haha.

Sep 27 11 - 7:42am

I was 21 and half..was worth the wait.But I really wanted to get rid of it.

Sep 27 11 - 10:47am

I liked this one. It wasn't as sensitive or as cloyingly affected as other first time stories ("we were in a playground on the swings at 3 am. His eyes looked dangerous in the moonlight")

Sep 27 11 - 11:53am

Came in unison? Yeah, whatever. I seriously doubt she came. Typical dude wishful thinking.

Sep 27 11 - 12:28pm

She came from four or five minutes of nothing but vaginal intercourse? Either (1) she was faking it for his benefit; (2) she'd had far more practice at sex than her supposed one other partner would lead one to think; or (3) she was touching herself in order to get herself off.

Setting that aside, given this young woman's behavior, I have to believe she'd had more than one other sexual partner. Perhaps she'd had vaginal intercourse with only one guy before the author, but I tend to think she's jerked off (or been fingered by), blown (or been eaten out by), dry/wet humped, and maybe even backdoor fucked quite a few. Because, you know, all that shit doesn't count to some "devout" types.

If you ask me, the author of this piece still sounds a bit naive, even after his initiation into the "been there, fucked that" club. I mean, that he still takes this woman's word for it that he was only her second partner? That he doesn't seem to regret fucking Little Miss Religious without a protection? That he doesn't look back and think that he should've at least pulled out? Yeah, he still hasn't learned anything.

Cuz, seriously, only virgins tell their prospective partners the truth about their magic number. The rest of us tend to do what the young woman in this story probably did: Lie.

Sep 27 11 - 1:54pm

You really are a bitter person, aren't you?

Sep 27 11 - 2:36pm

I agree with Wow, that couldnt have been a more negative reaction, which is your right to spew but, as a sexually active female Id like to say you could be wrong. First of all, he says that he made his way into her pants with his hand to start off, and secondly, just because its vaginal intercourse, doesnt mean that the orgasm couldnt be created by clitoral stimulation by just their bodies being in right spot for him to be grinding on it. I know its worked for me... And as for her number of partners and how she was acting, well, did you really not ever feel horny or act like it or see how people act like it on TV until after you had 4 or 5 partners? I think most girls know how to tease long before they actually lose their virginity, myself included. Just my opinion. Perhaps you're just more inexperienced than you make yourself out to be "Ditto"

Sep 27 11 - 3:15pm

RE: Wow

Is it bitter of a person to criticize a 26-year-old adult for having unprotected sex and for not bothering to at least withdraw?

RE: 2ndWow

If we are to keep our exchange civil, perhaps we shouldn't opine about the extent of one another's sexual experience.

That said, I do maintain the unlikelihood of the woman in the story coming in unison with the author, after only a few minutes of nothing but thrusting. It's not impossible, of course; inadvertent clitoral stimulation can happen in the missionary position and some women do even claim to be able to come vaginally.

But I do still find parts of this story doubtful. Not impossible. But certainly doubtful, given the fact that many sexually active people do in fact lie about their number of sexual partners -- as I do still believe the young woman in this story may have done, given that she considers herself devout and claims to have little respect for those who "sleep around" (which, not for nothing, kind of seems like exactly what she did with the author, who never claimed they were in some sort of exclusive relationship).

Sep 27 11 - 3:31pm

Ditto, if all you did was criticize him for that, I would be with you 110%. It was completely naive and immature for him to have unprotected sex with her, yes. But you projected a lot onto the woman, and you seemed to imply, oddly, that if she was taking an active role in her orgasm, it somehow didn't count.

Sep 27 11 - 4:00pm

RE: dude

That's actually the exact opposite of what I was trying to convey. In my opinion, she would've HAD to take a far more active role in her orgasm than the author implies she did in order for her to orgasm (again, after only a few minutes of vaginal intercourse). Maybe she knew how to angle herself so as to get some clitoral stimulation; maybe she simply took the initiative to touch her clit herself.

Either way, I was simply trying to say that I think it's unlikely that he crawled on top of her, (virginally) thrusted away for all of four minutes, and got her to come.

Sep 28 11 - 8:20am

Failure to read article ("We came, nearly in unison.") leads to snarky comment and defensive responses.

"If we are to keep our exchange civil, perhaps we shouldn't opine about the extent of one another's sexual experience."

Too bad you're not taking your own advice. Since we're debating the merits of a women's sexual response in the missionary position I'll add my own anecdata which says, it is entirely possible in under four to five minutes without having to use extra stimulation. There's more to an orgasm than mere thrusting; anticipation of sex, touching, kissing, giving a guy a bj ...

But, in the end you're really missing the point that you're reading the sexual experience from the point of view of a MAN (I wish I could use em tags here) the only thing he left off in his war references was calling his penis a prick - heh.

Oct 16 11 - 12:22pm

You guys are lame. Its really not that hard to make a girl cum.
Maybe he was just doing the right thing and hitting the right spot. Geesh.

Sep 27 11 - 1:20pm

I really enjoyed the story and writing.

Sep 27 11 - 2:29pm

Nicely done. Your piece seems honest but not self-pitying, playful but not mocking, and admirably restrained throughout . (I admire the second to last parenthesis.)

Sep 27 11 - 3:11pm

The metaphors between war and sex make me wonder if the writer needs Miss Information.

Sep 27 11 - 3:27pm

Too well written and overly romantic. I don't believe its true.

Sep 27 11 - 5:03pm

she faked it.

Sep 27 11 - 5:58pm

The best-written MFT so far.

Oct 05 11 - 12:13am


Sep 27 11 - 6:57pm

Perfectly written. Nuff said.

Sep 27 11 - 7:55pm

@ditto...Its entirely possible for a woman to have a vaginal orgasm in less than that time. Unlikely, but possible.

Sep 27 11 - 10:08pm

Whats with all the bitching? This was far better then the usual tripe that gets put on here. (He was a moody leather jacket scruffy type and we hung out smoking pot all summer and finally did it in a playground...blah blah). Who honestly gives a crap whether the girl actually came or not.

Sep 28 11 - 1:20pm

that was actually pretty nice for the following reasons 1. being a former 26 yr old virgin(More power to ya) 2. Adding the bits and pieces about the American Revolution. and for those idiots who says a girl can't come within 5 minutes (saying shes faking or she was helping the process) have never 1. been horny beyond belief and 2. Never been a girl thats horny beyond belief, its AMAZING what can happen being really horny and having a dick within mere inches of your body.. :)

Sep 28 11 - 5:19pm

As a guy who also lost his virginity at 26, I really liked this story. Very well written. I'm surprised that birth control was not on his mind, though. It sure was on mine at the time.

Sep 28 11 - 9:46pm

I (unknowingly) took a boy's virginity once. He also lasted about five minutes and came right after I did. So, yes, it's possible. He didn't tell me he was a virgin until more than a year later.

Oct 16 11 - 10:53pm
Al Coholic

He only lasted five minutes and you didnt know he was a virgin? Sherlock Holmes wasnt on the case.......

Sep 28 11 - 10:23pm
Sydney Escorts

Aaww! Cute! For me, it really would mean a lot if you are with a virgin. I don't know. There's just something about first times. :)

Sep 29 11 - 10:22am

The people protesting that there's no way a woman could come after four minutes of thrusting need to date a broader spectrum of women and/or stop projecting their own experience onto womankind. Some women can come after five seconds, especially if they're turned on enough; others will never come at all, no matter what anyone does (including themselves). The range of human sexual expression is vast and diverse, and not everyone is invited to the best parties. That's life.

BTW I find safe-sex zealotry almost as tiresome as religious zealotry -- it's basically an analogue of slut-shaming, a way for people to get their self-righteousness rocks off and associate pleasure with guilt. Advocating for condoms is a good thing; belittling someone for not using them in a long-ago sexual encounter is just being a smug douchebag.

Oct 26 11 - 1:10am
Al Coholic


Jan 23 12 - 8:04am

Tell it to them! It may be unlikely but either way, who's the one more likely to know what happened?
And I completely agree on the safe sex rants; absolutely everyone nowadays knows the drill with condoms and birth control, so if they didn't use them they must obviously be regretting it like hell, and not needing the added pressure and shame-attempts from stranger's opinions.

Sep 30 11 - 12:06am

I need to have sex, i need more and more boys for fun, so guys cal me +918056116537

Sep 30 11 - 2:37am
Alaska Hannah

Call me for a good time 9074447021

Sep 30 11 - 9:18pm

What ever happened to celibacy?

Sep 30 11 - 11:37pm
Yes , please.....

Use a CONDOM!!!!!!

Oct 01 11 - 12:21am
Age 24

Well, this is certainly going to be a hard act to follow.

Oct 01 11 - 2:08am

why am I not suprised that this occurred in massachusetts. I'm gonna make a really broad assumption here, but as a boston native who lost his virginity at 23, i find a strangely puritanical vibe that surrounds boston and it's sexual openess or lack off

Oct 01 11 - 1:57pm

Massachusetts native here who lost his virginity at 27. Not only did I have to leave Massachusetts for it to happen, but I had to find someone else not from Massachusetts to lift me out of that trap.

Oct 03 11 - 3:06pm

Well-written and cute. It's nice to read a MFT that's not about a teenager.

Oct 06 11 - 6:52pm

This man is a writer. Fabulous! Write more, friend! Fucking great story. xo

Oct 17 11 - 8:26pm

everyone on this site is a slut

Oct 20 11 - 8:52am

intresting but next time use a condom pls.. u are puting urself and gals at risks

Nov 05 11 - 6:53pm

nice mix of feelings

Nov 10 11 - 3:36pm
9ice Dj

Wanna 4uck? Kal +2347033086194 Hahahaha. Gud article. Am one also

Nov 20 11 - 8:35pm

I bow down humbly in the preensce of such greatness.

Nov 21 11 - 3:03pm

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Dec 30 11 - 6:34am

I used to hang out with a lot of devout Catholics, and they would never acted in such a manner. They go on about how they would wait for marriage, wear their purity rings everywhere, go to confession to keep their minds pure, pray that others would refrain from premarital sex, etc. This girl is a sham.

Jun 22 12 - 1:51am
Great reade

This is the most lighthearted reading that I have come across thus far from this series. I like it! (I like History Channel too!)

Jul 08 12 - 11:59pm

Excellently written. I loved the jumps back and forth between the sexing and the History Channel.

Jul 31 12 - 12:08pm

Great story, I enjoyed the details and the master mind ideas that this author put together. I'm still a virgin as a male because I don't own a vehicle to go for midnight slut hunting LOL. Other then that some girls hate when I approach them on the street. Not all but some initial reactions are like "Who are you?" I want to save my v-card for someone hot, I have standards, I'm not desperate to lose it --

Jul 31 12 - 12:44pm

to some girl who looks like a buffalo or some ugly face baboon. Not all virgins are exactly innocent just like I am. I maintain my body and about 7/8 out of ten without having the so called jock body. I'm slim and got lil fat here and there due to lazyness. I dated a so/so girl and I couldn't press on, her personality sucked, her looks are not eye catching or ugly inbetween which is very odd, and she keeping her v-card for a relationship/sex. I tried to kiss her but she backed off and she likes me still, I'm considered her decent man unlike the others. Food for thought that girl that I mentioned is a prime example that personality is a must for relationships, I'm too good for her but yeah that's life. I'm working out again and fit, I'm 21 male virgin, not ashamed I don't alienate non-virgins I hate all the stupid excuses virgin girls make, possibly they over think it so much. Their personality probably sucks too, ugly and such or religion issues. I kissed a hot girl before but she had a bf I didn't know of and her indian parents are racist gay like the rest of them, I'm caucasian so it means indian girls are off limit. She wants to save v-card for future bf but she likes me no matter what because I treated her really well like a gentlemen and our personalities both connected well along with physical attraction. As a virgin at 21 I'm late but not very late LOL, my time will come to either stay with a pretty girl that is meant for a relationship or the dump fuck girls LOL too that come along. You see not all virgins are to judged as undesirable like me, we are like any other person but unlucky for whatever situation it may be. I could of lost my v-card to a ugly girl but I don't want to, it's like forcing yourself which to me is extremely degrading. Anyways to sum it up I'm a virgin because no car to party hard and lack of public bus that stop where I live like 11pm I wish I had been back in the city that had 24-7 public busses. Nice talking to all if uou read my long post tell me what you think.

Aug 01 12 - 1:19am

Why do virgins complain about losing it when they can possible not be one hopefully by a decent looking person? Word of advice if you have a good looking face which I have then workout and focus on your future as well. Then hit some part n clubs if you can, be confident and who cares what you say even if you have anything beeter to say, no shame no game. My only issue is should I start creeping many girls and not give a fuck or do it sometimes or when I finally own a vehicle strap in for chick hunting at night parties or clubs or anywhere which would be creepy LOL. I remember getting a cold reject but I don't creep enough to get more rejections or chances. Why do I use the term creep is because I'm talking about talking to random chicks anywhere LOL.