How Not to Get Laid

A compendium of coitus rejectus... because we learn more from our failures

A forum for stories about all those amazing sexual encounters you almost had, but didn't.

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Archive for the 'Virginity' Category

The Eastern Hot-Bellied Hinter

Posted: April 3rd, 2007

1 comment;

(Our 50th story AND our first one from The Netherlands! Enjoy. — SF)

Submitted by Oblivious, 25, The Netherlands

So I was like 18 or 19, in high school, and green as they come when it came to sex. I was also shy of ladies, *very* shy. We are talking “blush from hell” shy when I had to face a girl I liked.
Then there was this girl, who was half arabian and half asian. I wasn’t madly in love with her or anything, but I’d file no complaint were she to invite me over to her place, if you catch my drift. I always had a thing for foreign girls, and she did fit the profile alright. Okay, perhaps I had a bit of a thing for her, I’ll admit.

In school we had these designated study hours, and we wrote letters sometimes to pass the boring hours. One day I let the innocent and shy thing work for me, and wrote her a question “innocently” asking whether the women’s body really did react in a certain way to air conditioning on a hot day (like I didn’t know). To my suprise I got a semi-embarrassed smile delivered with the note that came back to me, which indeed contained an honest answer. Perhaps I should have taken that as a sign that she was interrested, but innocent as I was, I didn’t have a clue. Or perhaps she was just embarrassed by the sudden nature of the question. I never was good at picking up signals from girls.

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When I Pitched a Tent

Posted: February 26th, 2007

4 comments so far

I went on a cross-country teen tour for a couple summers in high school, and the second time around, I got lucky. Her name was Amber, and she was a total firecracker of a girlfriend: hot, adventurous, and horny, every high school boy’s fantasy. Problem was, this tour was heavily chaperoned, and finding time alone with Amber was difficult. Most nights, we stayed at youth hostels or in cabins, and the boys and girls were strictly separated. But as luck would have it, we had a couple nights ahead of camping in the woods. An ingenious plan was hatched.

Amber would be spending the night in a two person tent with her friend Sara, who just happened to be going out with my friend and tent-mate Matt. We agreed that at two in the morning, after everyone was asleep, Maria would slip out of her tent and sneak into ours. I would then sneak into Amber’s tent, and the two couples would spend the next three hours getting down and dirty. Condoms were purchased in anticipation of the campout, and the four of us could hardly contain our excitement.

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It’s Not Just About Sex, I Swear!

Posted: January 26th, 2007

1 comment;

Back near the dawn of time, I spent summer and christmas breaks working alongside a smart, beautiful, smart-ass girl. The banter was legendary. Never had I compatibility with someone that devastatingly intelligent, stunning, and, well, dirty. However, due to a high-school-ish lack of self-confidence and cluelessness, I assumed our linguistic sexual interplay was merely in the land of “let’s just be friends”ishness.

Eventually, our friendship progressed into letter-writing and getting together with groups of friends now and then. I think our flirtiness via snail mail and parties got to the point where I somehow indicated my real feelings, for she responded with a “I’d love to go out with you, but [her best friend] has a crush on you and I wouldn’t want to hurt her.” So after much soap opera garbage and letting down the friend easily, I got that first date. And it was spectacular; the specifics were better than I’d imagined (a story for another website?). This was an open-minded girl! But I stopped short of home plate that evening, I don’t know why: I’d never had sex, lack of self-confidence, first date, stupid, etc. And we went on for a couple of weeks, and here’s where the train falls off the track.

Rather than trying to reignite the passion and fun and fearlessness of that first night, I became a supreme fluffhead schmuck. A far-too-expensive necklace for Christmas. Teddy bears. Little gifts all the time “just because.” Discussions at her house, alone, without progressing to making out. Too much obsessive attention WAY too soon. Trying to show her the relationship wasn’t just about sex.

And then, well, it wasn’t. She let me down easy, but she never really explained why she broke it off, to my lifelong frustration. We wrote letters for a while, even with some of the flirty stuff thrown in, halfheartedly, but that was it.

And in twenty years, I’ve never met another woman with that same combination of smarts, beauty, humor, and pure sexuality. How’s that for schmuck?

Submitted by Snake, Age 35, Boston

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Always Use the Rubber Tongs

Posted: January 1st, 2007

17 comments so far

I was a junior in high school dating a senior. She was a cheerleader and very cool. I was a good athlete, which helped my social status. But I also suffered from chronic dork-dom and occasional episodes of buffoonery, which didn’t. I knew it was only a matter of time before she realized this and dumped me.

I had to act fast.

Sadly, knowing I had to act fast and actually doing it are two very different things. The chance to finally lose my virginity was there, but the window of opportunity would not be open long. Weeks went by and so did the bases. First. Second. Third was discussed, which was pretty good for me. I felt that getting to third base pretty much made home plate a foregone conclusion (Years of experience would later prove this not to be the case, but I didn’t know that then).

One Sunday night, she casually suggested that I come to her house to study that Thursday, coyly tossing out the fact that her parents would be at the movies. I managed to coyly ask if there was a chance that we may do more than study and she coyly responded “Maybe.” We were both being very coy and, looking back, it’s a little nauseating. But at the time, it was riveting and totally hot.

Monday passed. And Tuesday. Each day there would be piercing gazes in the halls and evening phone conversations about Thursday.

Thursday. It shined like a beacon on a cold, virginal night.

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The Story of the Born Again Virgin

Posted: December 13th, 2006

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I was at a party during college once and was talking to this girl. Her face was just okay, but her body was awesome. I kept picturing what it would look like naked and what it would feel like.

So somehow, the conversation gets to this place where we’re talking about sex, and she tells me she’s a “born again virgin.” Eager to do anything that will get me closer to doing it with her, I tell her that I too am a born again virgin. Not smart.

So things progress and I find myself back in her room making out. Things are getting good, so I ask her if she has a condom, to which she replies, “But you’re a born again virgin.”

What could I do? If I’d told her the truth, she would’ve tossed me out, so I had no choice but to play the part. Needless to say, my born again virginity was not lost that night.

Submitted by Paul, Age 32, NY

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Onesome, Twosome, Threesome

Posted: December 11th, 2006

2 comments so far

(Welcome! Since this is to be a website where I ask complete strangers to spill their guts about things that happened to them in the past, I suppose it’s only fair that I use this inaugural post to share an anecdote of my own. Please enjoy this story and all those that follow! with love, Stewart)

I was a virgin at the time. Most of the stories begin this way. Fresh out of college, Benjamin Braddock had nothing on me. I was horny, repressed, and overeager.

The terrible thing about being a twenty-something virgin – aside from all the obvious things – is that I was never able to approach a romantic relationship with the same sort of carefree nature my peers could. For me, every date, every girlfriend, every interaction with the opposite sex became loaded. Will she be the one? Will this be my chance to lose the scarlet V emblazoned on my chest?

Not long after graduation, I spent four months traveling around the country with a group of actors. Very quickly, I managed to couple up with the girl I considered to be the “hot one” of the bunch. I’d like to say this made me the alpha male of the group, but in truth, I think it just made me lucky. She was smart and funny and said she used to model, which I got a real kick out of. She may have modeled for the Toys ‘R’ Us catalog when she was five for all I knew. Didn’t matter. My young ego was sufficiently stoked.

She was cheating on her boyfriend with me, which I was okay with because it didn’t seem like that relationship was going to last. Furthermore, the illicit nature of our road-trip romance made it all the more exciting for both of us. We were sneaking around motels across the southern part of the country, making out and getting all hot and heavy. Surely, I thought, it was just a matter of time. Read more »

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