When I was 17 my girlfriend at the time was finally ready to have sex. I, as one might expect of a 17 year old, was excited. Neither hell nor high water was going to stand between me and my final destination.
 
I get ready for the night, trim everything up, shower extra well. Unfortunately there was also an issue. I have a digestional disorder that sometimes cause my shit to become large and quite solid while still inside me. I wasn't aware it was a treatable problem and, in fact, just thought everyone had to deal with the equivalent of anal kidney stones. I bring this up because I had a mighty one which had been loaded into the gun for several days.
 
Let me set the scene. Her parents are away. We have her house to ourselves. She was always a little kinky so she demands we do it in her parents bed.
 
I walk in to a candle holocaust. She's been working on this all day apparently, and its as bright as high noon in there with the lights off. Which is good, because she proceeds to do a sweet, sexy little dance for me. At 16, she was AMAZING. For those of you who never experienced a female at that age, I pity the fool.
 
Now I'm sitting on the bed, watching this dance. I smile and tell her how good she looks. Unfortunately, most of my attention is focused on the dull throbbing from my sphincter and the large amount of intestinal discomfort associated with not dropping duce in days. But somehow I still get hard and we go to town.
 
She starts out on top, then we switch. I bend her over the bed, and I even smack her ass (a ballsy move at the time, but she loved it). Due to my built up distraction, I last for what seems like FOREVER. She can't stop moaning and telling me how good it feels, and then she says what every man wants to hear "I want to make you go in my mouth." I **** love women.
 
So she goes down on me. She was always average at best in the head department but at least she tried. She pops my **** out of her mouth long enough to look up at me and say "tell me if you like this". Then I feel it.
 
She stuck her finger up my ass.
 
My brain hits the panic switch and every muscle in my entire body locks up tighter than a three year old virgin. But its too late.
 
I take a massive, PAINFUL, PAINFUL shit, all over her parents comforter.
 
No, you aren't understanding. I mean large. Huge. IMMENSE. Take your largest shit and multiple it by forty-two and you'll have an idea of what flew out of me.
 
And gents, when I say flew, I don't mean "I pooped." I mean "projectile". I mean "hurricane force winds hitting an umbrella stand". And due to my condition, it comes out as a large, dark brown, smelly harpoon.
 
I know it hit her. I didn't see it. She ran screaming "OH MY GOD OHMYGODOHMYGODEEEEEWWWWWWWW" but I always imagined that, due to her position, it hit her right in the chin. Or at least the tits.
 
I would like to say I got up to go after her. But I heard the bathroom door shut and I just lied there. The smell hit me after a few seconds. It smelled like someone rolled a cat in shit and threw it into a tire fire. I looked down and saw, to date, the largest bowel movement I've ever heard of laying on the bed. Then I noticed the blood, and when I did, I noticed the pain.
 
Apparently the fact that it was so large caused it to rip my ass a little bit (thought I was bleeding from the inside. This little doctors trip the next day is what taught me of my condition). There was a small pool of blood where my ass had been. A final reminder of the exact place and moment I lost my virginity. I will treasure this memory for all my days.
 
I grab my shit with my hands and go to the downstairs bathroom. I throw around 1/3 into the toilet and flush, fearing any more will clog it and only add to my already significant woes.
 
I stand there, holding 2/3's of my biggest shit of all time, feeling a trickle of blood flow down my leg, trying to ignore the sharp pain stabbing my rectum. I find myself wishing I had a photo of this.
 
Anyway, I finish flushing my baby, clean off my hands, jam toilet paper between my cheeks (I skipped the bandaid) and went upstairs. I could hear my girlfriend sobbing from behind the bathroom door. I decided not to say anything to her and just keep moving. The smell in her parents room was abysmal. Its like when you take a shit and walk out of the bathroom you think "hey not so bad today," but then you walk back in to grab your magazine and go "HOLY SHIT!". It was one of those moments.
 
The scene is burned behind my eyelids for all time. My life. My shame. My very first time smelled like a pile of dead babies. I quickly got dressed since the heat from ten thousand candles was making the room feel more like a port-a-potty. I was aware enough to grab the comforter on my way out and drag it downstairs to their washer. Also the top and bottom sheets since the blood had leaked on through all the way to mattress. Still no sign of the GF but at this point I considered it a blessing.
 
I jammed in the washer with 3 loads worth of detergent and set it on spin, knowing that not even the hand of God would save these linens, let alone Tide and Snuggles.
 
Then I left. I avoided my GF's calls for days until she came to my house. We had a long talk about what happened. Talk being synonymous with "breaking up with me because I shit on her". And it was all over. She promised not to tell a soul and I don't THINK she ever did. She was probably as ashamed as I was about the whole deed. But I will always this happening as the most embarrassing thing that has ever happened to me.