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 'Lothario Story' Category

Better Late Than Ever

Posted: June 27th, 2007

2 comments so far

Submitted by Teri, Age 24, Hialeah, FL

Juan was a dreamboat in his pictures, and our online flirtation got pretty serious pretty quick. We talked on the phone and planned our date, and he was pitch perfect: confident, cool, and funny. He gave very good phone. He was going to pick me up from my apartment at 6pm, and we were going to go the beach to catch some dinner.

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22 Votes | Average: 3.77 out of 522 Votes | Average: 3.77 out of 522 Votes | Average: 3.77 out of 522 Votes | Average: 3.77 out of 522 Votes | Average: 3.77 out of 5 (22 votes, average: 3.77 out of 5)
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A Snapping Young Lad

Posted: June 13th, 2007

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Submitted by Sally, Age 30, New York, NY

I was on my first date with Cliff. He was a former bad boy with the sort of good looks that had surely led many girls astray. But he’d cleaned up his act in the last decade, at least that was the story: he’d gotten off drugs, gone straight, headed back to school, and gotten his real estate license. Now he was doing quite well for himself as a real estate agent, and seemed like a fine catch.

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23 Votes | Average: 4.43 out of 523 Votes | Average: 4.43 out of 523 Votes | Average: 4.43 out of 523 Votes | Average: 4.43 out of 523 Votes | Average: 4.43 out of 5 (23 votes, average: 4.43 out of 5)
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A Man in Dolphin’s Clothing

Posted: May 23rd, 2007

4 comments so far

Submitted by Sarah, Age 31, Philadelphia, PA

I met this marine biologist (yes, a marine biologist!) on match.com, and he seemed like a real catch: cute, funny, sincere. We exchanged a few emails, then he left town for a month on some research expedition before we could actually meet. While he was away, he emailed me, and I emailed him back. Soon, it got to the point where we were writing each other pretty much every day. It was fun and exciting to have this romantic pen-pal, and we both looked forward to finally meeting once he returned to town.

On date night, he arrived at my apartment ten minutes early. There was a little surprise on my part when I first opened the door. He wasn’t bad-looking exactly, but his internet picture was definitely a best-case scenario. So…no instant fireworks, but that was okay. I felt I had a good guy here, and I needed to give him the benefit of the doubt.

But first, I had to finish getting ready. I excused myself and returned to the bathroom. When I opened the door five minutes later, I found him leaning against the sofa waiting for me — BUCK NAKED.

“I just couldn’t wait any longer,” he said.

I suppose I should have been scared or freaked, but for whatever reason, I just cracked up. He looked ridiculous standing there with his average schlub body, naked as a jaybird. It struck me as really silly, and I could not stop laughing. He got VERY red in the face, colossally embarrassed. For some reason, I said, “no, it’s not you” — but of course it totally was.

He put on his clothes with great speed, and apologized profusely. Neither of us quite knew what to do at that point, so we ended up going to dinner as originally planned. The rest of the date wasn’t technically awful, but his bold disrobing cast a pall of embarrassment over the whole affair, and I was very happy when we skipped desert and said an early goodnight.

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59 Votes | Average: 4.56 out of 559 Votes | Average: 4.56 out of 559 Votes | Average: 4.56 out of 559 Votes | Average: 4.56 out of 559 Votes | Average: 4.56 out of 5 (59 votes, average: 4.56 out of 5)
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He’d Have Wanted You To Kick Me In The Balls Too

Posted: May 4th, 2007

3 comments so far

Submitted by Certified Douchebag, Age 19, Pennsylvania

How about this one: You’re dating this girl, and things have been going well. You’ve fooled around naked before, but haven’t had sex yet. You’re thinking it could be any day now.

Then her grandfather dies. She leaves school for a week. She comes back and keeps having other plans, so it takes you forever to see her again. After a long while, she invites you to her dorm, you have a couple beers, and FINALLY you’re making out on her bed. But she’s still kind of sad about the whole grandfather being dead thing. You kiss her and touch her as she talks. Your patience is getting short, your balls blue. She says, “I think my grandfather would have really wanted to see me graduate.”

You say, “I think your grandfather would have really wanted you to take off your shirt.” She says nothing, and because you’re fondling her breasts, you don’t see her eyes, which probably look shocked, not believing you said what you just said. So you go even further, guiding her hand to your crotch, saying “I think your grandfather would have really wanted you to touch my penis too.”

That’s when she tells you to get the fuck out, and you realize how stupid, insensitive, and not at all funny you’ve been. You want to kick yourself in the head. But you don’t, because your legs don’t work that way. So you go back to your room, look at internet porn, and then tell the world about your stupidity on some site about not getting laid.

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78 Votes | Average: 4.64 out of 578 Votes | Average: 4.64 out of 578 Votes | Average: 4.64 out of 578 Votes | Average: 4.64 out of 578 Votes | Average: 4.64 out of 5 (78 votes, average: 4.64 out of 5)
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Actually, I Charge Even MORE For Sex

Posted: April 19th, 2007

2 comments so far

Submitted by Allison, Age 23, New York, NY

My first date with “Fred” wasn’t amazing, but it was good enough to warrant a second, and the second was just good enough to warrant a third. I’m pretty picky about guys, and, because I’m aware of how picky I am, I’ll sometimes overcompensate and give a guy a chance even when I secretly know he’s not right. This was the case with Fred. I knew it wasn’t going anywhere, which is sort of why I didn’t put up a huge fight when he insisted on paying for the fancy dinner we ate on date #3.

Throughout dinner, I went back and forth on whether I was going to let Fred get physical with me later. I knew he wanted to pretty badly, and although I knew this couldn’t go much further, he was real pretty, and … did I mention I’m indecisive?

Okay, so he walks me back to my place, and by this point, I’m starting to get tired of his personality and I’m thinking I probably shouldn’t hook up with him. I make my goodbye at the front door kind of hasty, and seeing his chances fly away he makes one last ditch effort: “Do you mind if I use your bathroom quickly?”

Okay. Fine. He gets the invite upstairs. But once he’s done, I pull the “I hate to kick you out but I have to get up real early tomorrow” line, and he’s clearly frustrated. “Oh, man,” he says, “So you’re really kicking me out …” I apologize, but stand firm. He makes no effort to disguise that he’s stewing in his boots now, and he stutters, searching for the right words. Finally he says: “Man! Do you REALIZE how much I spent on dinner?”

I couldn’t believe it. He was trying to make me feel guilty for not hooking up with him, and he actually thought this strategy might change my mind somehow and get me all hot for him. “Um, you can leave now.”

He slammed the door on his way out.

Hey, call me picky, but my instincts are good.

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38 Votes | Average: 4.24 out of 538 Votes | Average: 4.24 out of 538 Votes | Average: 4.24 out of 538 Votes | Average: 4.24 out of 538 Votes | Average: 4.24 out of 5 (38 votes, average: 4.24 out of 5)
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A Big No No

Posted: April 16th, 2007

2 comments so far

Submitted by Joe, Age 25, Cleveland, OH

Boyz,
If you’re like me and you like big booty, DO NOT mention this to your girl before you get to know her. Dig…

ME: Mmmm, I love me a woman with a big ass.
HER: You did NOT just tell me I had a fat ass!

And this is before things got really ugly. Think twice!

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22 Votes | Average: 3.59 out of 522 Votes | Average: 3.59 out of 522 Votes | Average: 3.59 out of 522 Votes | Average: 3.59 out of 522 Votes | Average: 3.59 out of 5 (22 votes, average: 3.59 out of 5)
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Twice Bitten, Thrice Pissed

Posted: April 11th, 2007

1 comment;

Submitted by Lady of the Lake, Age 20, Ann Arbor, MI

I discovered that my boyfriend had been cheating on me – and he’d done it with two different girls (he’d had sex with one and made out with the other). When I found out, we had a huge fight, and I told him to get out of my apartment and never come back. I was devastated and couldn’t believe I’d been such a sucker.

A couple days later, he calls me and asks when he can come by to pick up his things. I say Tuesday evening. Tuesday comes, and he shows up in this really nice shirt with flowers in his hands. I ask, What’s with the flowers? He says they’re to say he’s sorry. He says he knows we’re broken up and he’s fine with that, but he just wants to apologize. Whatever. He asks for a drink. I refuse. “Just get your shit and go,” I say. But he’s taking his sweet time. Finally, he comes right out and says what’s on his mind.

“You know,” he says, “it’s a shame we never got to have breakup sex.” He pauses and gives me a smile. “Of course, we still could …”

That’s when I spilled my cranberry juice on his stupid fancy shirt.

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43 Votes | Average: 4.51 out of 543 Votes | Average: 4.51 out of 543 Votes | Average: 4.51 out of 543 Votes | Average: 4.51 out of 543 Votes | Average: 4.51 out of 5 (43 votes, average: 4.51 out of 5)
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Good for the Heart, Bad for the Groin

Posted: April 6th, 2007

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Submitted by Chris, Age 32, Washington D.C.

I felt confident and mature even though I was barely 22. Fresh out of college, I already had my own apartment, and, after lucking into a plum job at John Hancock, I was making twice as much money as any of my friends. All this, and I had just started dating Sarah, who was not just a knockout, but four years my senior. I was dating an older woman – a hot older woman!

But, as I said, I was young and cocky. And horny. That’s why, after three and a half dates, I invited her to my place for a dinner that I would cook. It had been almost two years since I last had sex, I was eager to close to deal, and I thought, what better way to do it than by cooking her dinner? How mature of me!

The only problem was, I was pretty clueless in the kitchen. I called my mom for help (again, how mature!). We went through all my favorite recipes of hers until we settled on one that was easy and sure to impress: her beef and bean stew.

Did it work? Not exactly. Sarah seemed to like the stew, but she didn’t eat much. Stupidly, I encouraged her to eat more, guilting her, saying, “If you like it, eat more. I’ve made so much!” So she ate more. But then she behaved awkwardly for the rest of the night and excused herself before things could really get physical, claiming a major headache. No sex for me.

Sarah and I ended up dating for two years, and eventually I learned that she had actually wanted to have sex with me that first night, but my choice of entree has scuttled our chances. Sarah has a very sensitive digestive system, and such a healthy portion of beans and beef make her fart like nobody’s business. Apparently, my cooking gave her such a bad case of gas – she’d become self-conscious. She spent the whole evening trying to hide her farts from me, and eventually begged off the sex because she knew she wouldn’t be able to control herself with her legs wide open.

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39 Votes | Average: 4.51 out of 539 Votes | Average: 4.51 out of 539 Votes | Average: 4.51 out of 539 Votes | Average: 4.51 out of 539 Votes | Average: 4.51 out of 5 (39 votes, average: 4.51 out of 5)
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Thinking Outside Her Box

Posted: March 28th, 2007

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Submitted by Casey, Age 24, Boulder, CO

I’m in college. One date away from finally boning Wanda Lewis, and that date is tonight. I think about her perfect pair bouncing around in those tight tank tops she always wears as we IM to confirm our plans. I’ve been looking forward to this for a long time.

A new window pops up. It’s my boy Evan who wants me to come out to a rager tonight at SAE.

“2nite? u fuckin crazy bro? i’m boning wanda lewis 2nite.”

That ought to make him jealous.

“excuse me?”

Oh yeah, he’s pretending like he doesn’t know her. That asshole. He knows EXACTLY who I’m talking about.

“u know, tank top girl with the tits from murray’s econ class.”

No reply. Then I read:

“casey, are you IM-ing with someone else?”

Holy hell. I’ve been typing in the wrong box.

I am the biggest idiot in the world.

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41 Votes | Average: 4.44 out of 541 Votes | Average: 4.44 out of 541 Votes | Average: 4.44 out of 541 Votes | Average: 4.44 out of 541 Votes | Average: 4.44 out of 5 (41 votes, average: 4.44 out of 5)
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Charlie’s Big Problem

Posted: March 26th, 2007

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Submitted by Kate, Age 29, Boston

It had been a LONG time for me since I’d last been with a guy and certain body parts were going to go on strike if I didn’t get some action soon. Enter Charlie. I met him at the gym (which was probably my big mistake right there, but anyway…). He had kind of a young Val Kilmer thing going on and he was a lawyer and smelled real nice (even at the gym), so, yeah, I was VERY excited when he asked me out.

We met at a French restaurant and he arrived looking and smelling even better than normal. We sit down and we’d barely started reading the menu when he lays this one on me:

“You should know, if I act at all funny tonight, this is my first date since my girlfriend broke up with me. It was a pretty emotional breakup.”

Uh, okay…

“No problem,” I say, ignoring the warning bells in my head.

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38 Votes | Average: 4.42 out of 538 Votes | Average: 4.42 out of 538 Votes | Average: 4.42 out of 538 Votes | Average: 4.42 out of 538 Votes | Average: 4.42 out of 5 (38 votes, average: 4.42 out of 5)
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Color Me Reassured

Posted: February 21st, 2007

1 comment;

“If you’re on the pill then we don’t need a condom. Trust me, I know when I’m getting an outbreak, and I’ve been totally clear for over a month now. It’s all good.”

Submitted by “It is SO not all good”, Age 23, Minneapolis, MN

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24 Votes | Average: 4.25 out of 524 Votes | Average: 4.25 out of 524 Votes | Average: 4.25 out of 524 Votes | Average: 4.25 out of 524 Votes | Average: 4.25 out of 5 (24 votes, average: 4.25 out of 5)
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Valentine Story - Her Front Row Seat

Posted: February 9th, 2007

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I was dating a guy I probably shouldn’t have, but I was young (22) and I didn’t know any better. He was 30, he made a lot of money, and he was the sort of guy who liked to show you how much money he made, the sort who would aggressively pay for everything just to show you how little money mattered to him. At this stage in my life, I’d be repulsed by that, but at the time I didn’t know any better (or maybe I did but wasn’t listening to the voices in my head)

Did I mention he was hot? Um, yeah. He was kind of hot, which is probably why I let myself get swept up by him instead of running away.

We’d gone out a handful of times, and while we hadn’t technically slept together yet, we’d gotten pretty close. So when he told me he wanted to take me away for Valentine’s, I was pretty darn excited and very ready for the next step.

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23 Votes | Average: 3.57 out of 523 Votes | Average: 3.57 out of 523 Votes | Average: 3.57 out of 523 Votes | Average: 3.57 out of 523 Votes | Average: 3.57 out of 5 (23 votes, average: 3.57 out of 5)
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