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Waking Up With A Shemale!

I was in Thailand with a few buddies and checked out some clubs in Phuket. I got hammered and then got separated from the other guys. At some point this sweet slutty looking local came up to me and asked if I would buy her a drink. I figured she was a hooker but when I questioned her she claimed she was just into me.

One thing led to another and the next thing I remember I was waking up next to her in my hotel room. I'm cheap so I was sharing a room with another dude... he was asleep in the other bed.

I figured it was time for a little quiet morning action. I started making out with my date. After a few minutes of this she starting giving me a little tug. Thinking it would only be polite to return the favor, I reached down to play with her and suddenly found out she, was in fact, a he!!!

I screamed, jumped out of bed, and yelled "you're a dude!!!"

Embarrassed he/she quickly got dressed and ran out as my friend roared in laughter for about 20 minutes straight.

Your alias: 
anonymous
You: 
Male
Your Date: 
Male
Where you met: 
Somewhere in Phuket
Average: 4.9 (9 votes)

A Sign From God?

I was set up on a date by my boss with her husband's best friend. Wanting to keep peace in the workplace, I agreed to go. Worst mistake I ever made.

My boss told me he was tall, cut and drove a "vette." He showed up, all 5'5" of him in a Chevette. During one part of the evening, while we were driving to dinner, the hood of his "vette" flew up and onto the windshield while we were driving past a cemetery. The universe gives good hints when it decides to. I had mistakenly thought "cut" meant muscular. Apparently it was referring to his lack of a foreskin.

All four of us; myself, him, my boss and her husband; went out for supper at a lovely truck stop diner. My boss's husband and my date left the table for a few moments to go to the bathroom. When they came back they were obviously stoned.

Your alias: 
anonymous
You: 
Female
Your Date: 
Male
Where you met: 
Through A Friend
Average: 4.8 (5 votes)

I Have To Get Going, How About A Quick Handjob... That's What She Said!

I met this chick at Kit Kat. We were making out on the dance-floor a bit and later I offered to drive her home.

Out front of her place we started kissing in the car. I wasn't really expecting anything to happen because she had said that she had to get up early the next day.

Kissing went on innocently for about 15 minutes and then she just blurts out "look, I need to get some sleep... if you want I'll give you a quick hand-job and you can call me next week."

I was taken aback, but quickly recovered to take her up on the offer. She did the deed but never returned my calls after that... win win, for me!

Your alias: 
Playa
You: 
Male
Your Date: 
Female
Where you met: 
Kit Kat
Average: 4.8 (4 votes)

Two For One Special

I admit I have a sex addiction, but my girlfriend, who lives with me, doesn't know. It doesn't help that I also often drink to excess.

Last night I went out with my buds to a bar after work and got bombed. I guess I must have picked up some random chick, banged her, and then stumbled home.

This morning I woke up with wood, as I often do. My girlfriend was feeling amorous and started playing with me. After a few minutes she pulled the covers back to reveal that I was still wearing the condom from last evening's encounter.

Just as I thought the sh*t was about to hit the fan she turns to me and proclaims "good boy, you're ready for me!" With that she climbed on top of me and gave me one the best rides of my life.

Do I feel guilty, absolutely. Will I change my evil ways, probably not. At least I got this off my chest... I do need help.

Your alias: 
anonymous
You: 
Male
Your Date: 
Female
Where you met: 
Bar
Average: 4.7 (3 votes)

The Open Zipper

I was on a date with this girl and, before the food came, I excused myself to go to the washroom. When I returned to the table, I realized that I had left my zipper undone, so I zipped it up under the tablecloth, ecstatic that she didn’t notice anything.

After a great dinner and some pleasant conversation, we got up to leave and as I walked away, I took the whole table cloth, and everything that was left on the table, with me. We’re still dating though, but she tells everyone that story and it still gets the laughs.

Your alias: 
anonymous
You: 
Male
Your Date: 
Female
Where you met: 
Set Up By Friend
Average: 4.6 (9 votes)

Fastest Gun In The West

This has never happened to me before, honestly!

I went out on a date with this girl I met online. We had a wonderful time at dinner and decided to hit a club after. After dancing the night away she was pretty hammered so I offered to drive her home. When we got to her place we started making out a bit in the car. She started to rub me through my pants. I don't know what happened but in an instant it was too much for me and I exploded. There was no covering this up as the front of my jeans were soaked and she knew it.

She uttered "that's ok" politely and got out of the car. I've tried calling and texting her but not surprisingly never heard back from her.

The worst part is she has now posted this story on her Facebook page.

How embarrassing!

Your alias: 
anonymous
You: 
Male
Your Date: 
Female
Where you met: 
Match.com
Average: 4.5 (4 votes)
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