[UfoZ8myCow]

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?