Submitted by J. Wordsworth, Age 26, Seattle

I was a freshman in high school. I was 6’3″, skinny, wore glasses and took AP and honors classes. As you can imagine, I was completely inept when it came to girls. Utterly incompetent. I was incapable of saying anything remotely intelligent. I was also painfully aware of how awkward I was, which was a vicious cycle as far as my penis was concerned.

In my biology class I noticed this girl. She was attractive, and more importantly, she talked to me. More accurately, she had to talk to me as she was my lab partner. She was into drama and also ballet. I didn’t know why I was drawn to a girl with demonstrated flexibility at the time; I just vaguely knew that it was good for a girl to be flexible (probably natural male instinct). She also had a car. And a license. I was 15 and had neither. Perfect scenario for me.

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Submitted by JP

note: this falls a little outside the norm for stories, but it seems to be in the spirit of the website.

I was getting physical with a girl I worked with at a Christian camp. We had spent the entire summer focusing on our work and not noticing our increasing attraction to each other until camp ended and things got intense fast. Over the course of our encounters throughout the week, we had approached second base, but were still admittedly some time away from “sealing the deal”, so to speak. Things were definitely headed in that direction though, and as young infatuation tends, our conversations crept towards speculations of the future and long-lasting love.

On one of our frequent walks, we had a discussion about marriage, as a principle. I made the mistake of telling her about some of my more unconventional (considering our conservative context) views of marriage- as in, I didn’t need the government’s approval to be married and I doubted I’d be interested in a legal ceremony.

Well, it was as if the wind rushed through the window and blew the candle out. This notion of mine flew in the face of her more traditional views, and she said, not quite so plainly, but on the spot, that if our views on marriage didn’t complement each other, well, what was the point of going any further?

Needless to say, there would be no doubles or triples from that point on, much less a trip around the bases. The fire had been doused by a bucket of holy water.

The first lesson? Know your audience. I would have liked it if things had gone on a little longer, but I was too idealistic and naive to think that something as simple as an opinion on marriage could deter blinding passion.
The second? Think twice before getting involved with a conservative.

Submitted by Mortality, Age 18, Sweden

I was on vacation with my family about a year and a half ago. I was still a virgin then, and I’d started talking and flirting with this guy.
On my last night there, he snuck into my hotel room.
So we made out and pretty soon all the clothes were on the floor.
Why no sex? He didn’t bring any condoms, and even though he said he’d pull out before he came so I wouldn’t get pregnant, I didn’t want to. Who knew where he’d been?

Submitted by Drew, Age 21, Toronto

My first week on the campus residence at college was typical: meet a ton of new people, make a ton of new friends, get hammered, and preform various acts of debauchery.

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(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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Submitted by LilB, Age 29, Philly

The Setting: A small New England campus named after a Supreme Court justice. Let’s just call it Scalia College. Good ol’ Scalia had an active and influential population of religious fundamentalists of a certain persuasion (won’t name names but when you think of Hollywood and international banking, they’re high on the list). Scalia was also not known for its attractive students. Women who in the rest of the world would rate at best a 5 (in low light and when you’re intoxicated) would suddenly be bumped up to a 7 or 8 at Scalia. This is what we called the “Scalia hot” phenomenon.

Anyway, there was one woman who was of this fundamentalist persuasion, who was “Scalia hot.” She had a huge rack and was well known on campus for being one of these religious types. I had been trying to get into her pants for months, but her fundamentalist beliefs and mode of clothing wouldn’t allow for it. Not that I didn’t try and she didn’t lead me on. She was very flirtatious and suggestive, but the line was drawn at some mild cuddling on the couch watching TV, or at best, in her room in a suite with the door wide open.

Until one night. Many students at Scalia in one particular set of dorms – the same quad where the lady of this story lived – had figured out how to pirate cable. In the mid to late 90s, pirated college cable equaled pirated college cable porn. Jackpot!

One night, I’m in her room. She shuts the door. We flip on the TV, start surfing through the channels … and she stops. On the porn channel. I think this is my chance. Can you tell how this story ends?) She leans over and kisses me. What do I do?

I keep watching the porn.

That’s why I’m posting this story to a site called How Not to Get Laid, and not Penthouse Forum.

(The story below comes from Dr. Blogstein who was kind enough to have me on his awesome radio show last night (CLICK to hear show). I challenged the doctor to send in a story he told about himself, a pair of 19-year-olds, and a dizzying moral dilemma. He came through, and it’s a story to which many of us self-professed “good guys” can relate. I now extend my challenge to everyone else. If you’ve been enjoying what you read on this site, the time has come to follow the good doctor’s example and share a story of your own! It won’t hurt, and I guarantee you’ll feel better afterwards. — SF)

Submitted by Dr. Blogstein, Age 31, NYC

I was on a cruise with five of my friends to celebrate my 27th birthday. It just so happened that my actual birthday night coincided with karaoke night on the ship. Exciting!

When dinner was over, we ran down to the ballroom where karaoke was to be held but alas all the slots were filled. I begged the girl to let me sing my rendition of Frank Sinatra’s New York, New York because it was my birthday. How could she say “no” to that? Sure enough, ten minutes later, she announces to the room that its my turn and also jokes that its my 21st birthday.

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I was spending my summer on Cape Cod, and I’d managed to start dating this local girl (we’ll call her Kate) who was on the verge of being out of my league. Young, beautiful, taut, frequently in shorts, you get the picture. And she was a good girl too, not the sort who was gonna sleep with any old guy who blew into town. And I liked that. But my point is: I knew I had to pay my dues if I wanted things to get as physical as you better believe I wanted them to get. I had to be the good boyfriend.

She had a little brother. Cute kid, maybe eight years old. I’d met him once and we’d hit it off. “I love that my brother has so much fun with you,” she’d said. Later that day, Kate’s bra came off for the first time. My simian male brain made the following connection: nice to Kate’s brother = hot love with Kate. This would be my undoing.

Couple weeks later. Big party at her parents house. Real WASPy New Englandy fancy backyard affair. I wore my best slacks, my best shirt, and my only blazer. Kate was fancy too. And deadly gorgeous. I was in lust, but had to control it until later. I had a feeling it might be my lucky night.

But first, I’d lay the groundwork. Play with the little brother. And so I did. I made him laugh. I used funny voices. Stupid voices. Probably-not-so-attractive-to-the-opposite-sex voices. I was silly. Too silly. I played pretend. WAY too well. I really had a blast with this little kid. Too much of a blast. Throughout the afternoon, I could see Kate slowly losing her interest in me, but I used all the wrong tactics to get it back. I doubled my efforts. I played tag with this kid. Football. Badminton. I got sweaty. And not just sweaty. I got arm-pit stained funky smelling unkempt hobo-at-the-tea-party sweaty. Really not a turn-on. And by the time I realized exactly how royally I’d screwed myself, it was too late to do anything about it.

Would I see her that night? No, on second thought, she really ought to help her parents clean up. And the next day? Well, maybe she had enough time for a movie, but not much else. You get the idea. A slow fadeout. To this day, I’m still kicking myself…

Submitted by D. White, Age 33, Philadelphia, PA

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