Mike Jones, Age 29, Cleveland, Ohio

In 2004, I was working on the presidential election. Our campaign had a major event and we were all put up in a fancy hotel. One of the long-term volunteers that I had been flirting with all summer was also at the event, but not staying in the hotel because she was local to the area.

Midway through the second day, we were giggling in the back of the room during a very boring speech. She commented about how exhausted she was, and I said that I’ve got a room in the hotel. Well, off we went upstairs.

On the way, I was incredibly nervous and wondering what the hell I was getting into taking a girl up to my room without any condoms (and a girlfriend back home).

My questions were soon answered when we got into the room. My campaign-assigned roommate (the former mayor of a major city) was sitting in his bed watching TV with no pants on. He asked if she would wait outside while he got dressed, and he left, but the mood was dead.

We laid in bed, she took a nap, and two hours later he came back.

In the end, I’m glad he was there, because I never saw her again, and I married my girlfriend.

Submitted by C, Age 27, Europe

So I had been traveling for a couple of months, kinda slumming it, and hadn’t been laid in a while. It was beginning to grate, getting to that stage where desperation was soon to follow. Then, a new girl showed up at the hostel-come-beach house where I’d been staying for a couple of days. She was cute, killer accent, and, most importantly, seemed pretty loose. I spent the next three or four days alternatively trying to woo her then surprise sex her. Progress was limited.

Finally, one night after a tantalizing water fight with wet t-shirts, we did a little kissing in the club. She told me she liked me but that I was getting too wasted every night. I promised I’d take it easy on the booze and show her a good time. We wandered back to the house and chatted a little on the veranda. Critically, we had a few more drinks. Then, she announced she was going to bed. She walked toward her room, gave me a meaningful look that I felt in my pants, and went in, leaving the door ajar behind her. I could see her pulling off some clothes as she got into bed.

I walked to her doorway.
I was pretty excited.
But I was pretty drunk.
I stubbed my foot on a litre bottle of water.
I had a funny idea.
She rolled over in the bed when I came in. I could see she was naked. I soaked her with a litre of cold water.

Two minutes later I was back outside her door again. This time it was closed. And locked. And the desperation settled in nicely for the foreseeable future.

Submitted by Rolf, Age 25, UK

It was my brothers stag do. A weekend of getting extremely drunk and a chance to chat up different women in a city I’d never been to before. I’m from a small village so you tend to chat up and get rejected by all the girls pretty quickly. I hadn’t had any action for a while and was starting to riled about it. You know it’s a lean spell when your mates start taking the piss out of you.

The first night was a good laugh, everyone getting extremely drunk, and the next day continued in a similar fashion. It came to the last, and we all went out for a quick bite to eat and then on to the hot spots of the town. We ended up in a super club. Five floors full of different music and about 2000 plus people. I couldn’t fail. I didn’t. We were all dancing (well, if that’s what you call it) when I noticed this not-too-bad-looking bird eyeing me up. I’m thinking “hello,” and the next thing you know, we are getting off with each other. Now, pulling on any stag, especially ones away, is legendary.

The bird then goes to me, “lets go back to mine,” then for some reason I will never know, I suddenly thought, “I don’t have a condom!!” I leave the bird and run ’round the club trying to find my mates, and when I do, they all give me a look of fright. The sight of me, shirt half un-buttoned and sweating frantically, asking for a condom, must’ve, I’m sure, amused them. I eventually manged to harrange some spare change out of one of them and grab some out of the machines.

We then left the club and started to walk back to hers. Then, bizarrely, she insisted on stopping off at the hotel she worked at. We called a taxi and then got back to hers, by which time I was really starting to feel the effects of the weekend’s boozing. We made it into her bedroom, but it was an impossible mission, adding to that about ten text’s asking for mobile phone pictures, and I was done. We fondle around for a bit, but I think I was a big disappointment to her. I said to her at one point, “ I want to do you from behind,” to which she replied, no chance.

I woke in the morning and thought perhaps some better luck, but she was having none of it, and as she went to make a cup of coffee I snuck out the door. Lost in a city I had never been in before, it took me two hours to get home.

Submitted by Francoiz, Age 27, The Netherlands

Two days after my 23rd birthday my girlfriend broke up with me. Facing a lonely two week holiday, I went off for a small vacation to Turkey on my own. Near the place I stayed, I found a good Turkish restaurant in which I enjoyed a superb meal and some good beers. A table next to mine was taken by some English people and a man who turned out to be German. All of them were much older then me (in their forties, I guess) but they invited me to join them after dinner. So I did. Drinking beer, having fun, drinking even more beer, having some good discussions, and eventually drinking more beer.

Midnight had passed a few hours ago and I was there sitting in an almost empty restaurant facing another beer and this 43-year-old (big) German when he suddenly announced he was a gay male (I already had noticed he was male, but not that he was gay). I told him I respect everyone, that it didn’t bother me, and that I still enjoyed the conversation we had.

But what came next stunned me in such a way that I can never forget this meeting with this man:

He bends forward a little bit and says: “I can give u a blow if u like “.

I gasped for air and held my chair tight (very tight!). I must have told him about the girlfriend who broke up with me a couple of days earlier. It crossed my mind that he could have meant something else. In Holland, a hash-filled cigarette is called a ‘blow’ or a joint.

I asked: “U mean a blowjob??”

Confirmative.

All I remember is that NOTHING HAPPENED. I walked back to my hotel room, went to sleep, and woke up the next morning with a terrible pain in the HEAD.

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 Rich, Age 26, Oakland, CA

I was in college and really hot for this girl. We’d hooked up and teetered on the brink of full-blown sex, but the timing of her monthly cycle had prevented us from going all the way. Then I skipped town — more bad timing — for an extended Spring Break in Russia. For the two weeks I was gone, I fantasized about her constantly. We exchanged a couple flirty e-mails. I was crazy with anticipation, and I arranged to see her on the very night I got back. I couldn’t WAIT to get it on with this girl.

Only one thing I hadn’t counted on: jetlag. My last night in St. Petersburg, I partied straight through till morning. My logic was that this would make it easier to sleep on the plane. No such luck. Door to door it was a twenty hour day of travel, and I hardly slept a wink on any of my three flights. I got home barely an hour before I was set to have my date, and I was running on pure adrenaline.

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(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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Went home with a girl from a bar one night and started getting down and dirty. I was completely drunk and suddenly realized that there was another bloke in the room, asleep on her floor. I asked her who it was, and she said, “it’s just my little brother who’s visiting from out of town.” That sort of killed the moment, as all I could think of is how angry I would be if I woke up and found my sister having sex with some random bloke. I got her to give me a blowjob instead, which was completely crap.

The next day I told my friend that I got a subpar blowjob from this girl, and he has told everyone, so now I have people I’ve never met before coming up to me and asking if I’m the guy who received the subpar blowjob.

Submitted by Alistair, United Kingdom

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