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Old 02-13-2009, 12:00 PM   #1
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The worst Date Story Ever....

What is the most rediculous thing you have done on a date that left you in an awkward situation. Good Luck!
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Old 02-13-2009, 01:34 PM   #2
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Ok well here it goes.

My name is Mitch Mckee. I am a world class pancake maker. I have made pancakes for Roseanne AND Tom Arnold.

No but really are we allowed to enter? I want some shoes.

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Old 02-13-2009, 04:13 PM   #3
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Anyone can enter.
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Old 02-14-2009, 10:35 AM   #4
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So umm where does one post their story then?
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Old 02-16-2009, 08:01 PM   #5
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Well you were suppose to enter here but i guess this contest is bust

Ended....
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Old 02-16-2009, 10:31 PM   #6
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Can I have the shoes then?
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Old 02-16-2009, 11:23 PM   #7
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Umm I want some shoes dag nab it. You should've just gave them to my while I was there today.
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Old 02-17-2009, 12:12 AM   #8
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No one wants to share the time they got an STD on valentines? or got drunk turned off the lights and decided to play who's in my mouth???

I don't think I have had anything like that happen to me, but I think Sean has a story or two.

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Old 02-17-2009, 12:14 AM   #9
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Quote:
Originally Posted by chico View Post
No one wants to share the time they got an STD on valentines? or got drunk turned off the lights and decided to play who's in my mouth???

I don't think I have had anything like that happen to me, but I think Sean has a story or two.

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Old 02-17-2009, 12:21 AM   #10
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Old 02-18-2009, 03:17 PM   #11
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Aw man... I was just about to tell you guys the story of Valentine's Day with my high school girlfriend and my (failed) attempt at anal.

That would have definitely been worth a pair of shoes. C'mon Dan!
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Old 02-22-2009, 10:28 AM   #12
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Elementary School Baller

So I remember once back in like 5TH GRADE, haha, There was this chick that had a crazy huge crush on me named Samantha, and day-in, day-out she would be like telling everyone how great I am blah whatever like everyone knew she was obsessed with me. And the crazy thing is, I was probably just as near as crazy about her too, but I was always embarrassed about so I pretended I didn't like her.


Anyway, it came to Valentine's Day and you know how in school the teachers would always let you bring in Valentine's cards and have small parties or whatever. Well in our classroom, we had these little cubbies for each classmate, and we were supposed to put our valentines in whoevers cubbie we wanted it to go to. So some kid puts this like enormous box of chocolates and elaborate card and all into this chick Samantha's cubbie....

...Everyone flips and immediately assumes I put it there (and I honestly didnt), so she's like head over heels right now, freaking out. And I remember she was so happy like oh myyy goossshhh. So here I am, and she asks if I put it there in her cubbie....and I pause for a sec...ponder this one out....and I come to the conclusion to tell her I put it there ahahahaha So I get all the credit for making this girl's day....and now I kinda feel bad for the kid who actually put it there.


THANKS KID WHO PUT VALENTINES CHOCOLATE IN HER CUBBIE!!!


Ok that was a little more cheesy than awkward...
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Old 02-23-2009, 11:27 AM   #13
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This one happend about 4 yrs ago, I had been dating this hooters calendar girl(miss november 2004-Jennifer Chapa) (if you guys wanna check her out) anyways V-day was coming up and I had everything planned out, I was gonna take her to this really nice restuarant and then see a movie that night.V-day happen to fall on a monday that yr, which was awesome because we would get to spend it together, this was going to be my first real valentine, so it was real special. The day before V-day came Jennie told me work called her in for an emergency shift for Monday night, so she wouldn't be able to make it. She told me how sorry she was and that she'd make it up to me and "do anything I wanted her to do" so I was like okay (thinking hell ya). Anyways, my father also had to work that night, so I just decided to keep my reservations and take my mom out for V-day. So we get to the restuarant right around 7, get seated, get ready to order, and out of the corner of my eye I thought I saw my gf, but my mom was deep in too conversation so I was focusing on that. So as the girl sat down in the smoking section I actually got a good view of the her and saw it was my Jennie, and I was "WTF" (actually said that out loud) and my mom was like "what happened", so I told her that Jennie just sat down with another dude, and that she was suppose to be working. She actually never saw me until they were done eating, as they got their check I grab our waitress and told her that I wanted to take care of their bill, to just have them come over and thanks me. So my mom and I moved out chairs so our backs were facing them, so they would have to walk around to get in front of us. So as the both of them turned to look at us, Jennie blurpt out "OMG" and turned so red in the face and the guy was like whats going on, and I said "Hi I'm chris, I'm her BF" They both just kinda stood there like a deer in head lights not knowing what to do(awkward). Finally they just kinda slipped out of there, and that was the last time I would see her for like the next 2 yrs. Haven't spoke to her since, except for the message I left her on her vmail.

I know it was long but man that was a crazy V-day, the story doesn't do it justice.
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Old 02-26-2009, 11:47 PM   #14
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Alright, here's my story. Deadline is tomorrow.


I went to a boarding school in Indiana, not because I was a bad kid, but because it was a prep school with a great hockey program (my main sport). So naturally, there were kids from all over the place that went there. Senior year I started dating a girl from Texas. It started as a fling, but then after we graduated we decided to stay together. Unfortunately, she was already committed to studying a year abroad in London, so the first real year of our relationship was via long distance. Afterwords, she went to Wellesley College (a prestigious all girls' school near Boston) and I was at UCLA, we were still doing the long distance thing. Because of the distance between us, we always tried to make the "most" of our visits (ie, we boned a LOT).

Our sophomore year, I made it a point to get to Boston in February to visit her for Valentine's day. I knew the weather would be unbearable and she would be miserable because it was the middle of swim season, so I thought it would make a nice surprise. So I fly out to Boston, and everything is great... Until that night. Turns out that as luck would have it, the magical time of the month was happening right during my visit. I had already received my red wings before, but she was still pretty shy about period sex, so it was usually a deal breaker.

The first night, there was no sex. This made me sad. So I enacted a plan. A plan that would forever change our destinies. A plan that would cement my status as a man's man. A plan... That would totally gross me out.

The second night, I took her to an amazing Valentine's Day dinner. I was bagging groceries at Ralph's at the time, so I wasnt exactly rolling in cash. But I really went all out, spent about $150 bucks on dinner, wining and dining at one of the most amazing restaurants in Boston. We went through 2 bottles of wine that night, so it's safe to say that by the time we got back to her dorm room (yeah, she lived in the dorms at the all girls' school), we were both feeling pretty frisky (booze + not seeing each other for a month).

Everything's going great. At this point I'm so shitfaced, I could care less if she was on her period. I would have banged a hole in the wall if it was warm enough. I'm leaning up against the wall, pants around my ankles, and she's on her knees in front of me doing the deed when she suddenly stops.

I look down at her.

She looks up at me.

Then she utters the six little words that just about every college aged guy dreams of: "Do you want to try anal?"

I hesitate for 0.00001 seconds before replying "YES!" without trying to sound too crazy. Another moment goes by and she goes over to her drawer and fetches a small bottle of lube. At 19 years old, all I could think was, "OMG OMG OMG OMG Anal! OMG OMG OMG Anal!" I had absolutely no fucking concept of the mechanics involved with anal sex. All I had was porn for reference.

Stupid, lying porn movies.

Much to my chagrin, simply spitting on my wang was not enough to get going. So, I grabbed the little bottle of lube she had gotten from the drawer and lubed up. Except again, I had no idea what I was doing and to boot, this lube was really liquidy and came out of the bottle much faster than I thought it would. So instead of a "dime sized amount" (as it said in the directions on the back of the bottle), I dropped an Exxon Valdez sized load of lube on my junk.

"Oh well. Fuck it. Let's do this!" I thought, as I slowly got down to business. At first I went really slow, because she was uncomfortable with it and it was obviously her first time as well. But, I was drunk. So I quickly got bored with the slow in and out and after about 2 minutes, I was jack-hammering away like an NYC construction worker on crack.

My head was spinning. I was entangled in this new, exciting sensation and it was working out to be everything I had hoped it would be. Eventually, I started to feel that magic tingle. You guys know what I'm talking about. I held back as much as I could then... "Ahhhhhhhh! And boom there goes the dynamite."

After a few moments, I came back from euphoria land. And this is where the evening went south. She was on the pill, so I was accustomed to what happens after the dynamite explodes inside her caverns, so to speak. Except this was different. When I pulled out, the aforementioned Exxon-Valdez sized load of lube came spilling out, mixed with my own additions, but unfortunately as you have all undoubtedly guessed as the astute readers that you are, that wasn't all that came out. Realize that a couple hours had already passed since dinner, giving ample time for digestion. So about a second after I pulled out, the lube came out, my junk came out, and then poop. A lot of it.

"Jesus H Christ in a chicken basket!" I yelled as I backed up in horror, knocking over a desk lamp. When she looked back and realized what had happened, she let out a huge scream and BOLTED out the door, butt ass naked, covered in lube, jizz, and poo and ran to the bathroom with world class sprinter speed.

Apparently, there is quite a bit of preparation that goes into anal sex before doing it. You cant just shove your junk in there and have at it. Stupid, lying porn movies.

It was gross and horrible, and after cleaning myself up, I balled up the sheets and threw them in the garbage can down the hall. Then I waited. And waited. And waited. She didn't come back. So I started to worry. When I found her in the bathroom, she was alternating between showering, puking, and crying from embarassment. Apparently, her sprint coupled with the amount of alcohol coursing through her system had triggered her upchuck reflex with a vengeance.

From then on, I was never allowed near her rear entrance again. We broke up shortly thereafter, although I'm not sure if the anal escapades had anything to do with it.

And that's the story of how I ruined Valentine's Day in 2004.

Can I haz DC Shoes?
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Old 03-04-2009, 09:35 AM   #15
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lol at the previous post
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