Note: Read the original "My First Day of School" piece that inspired this ongoing Aristocrats-style series. 

I will never forget my first day at Kingston Penitentiary. Believe me, I have tried my hardest, but I recall it like it was yesterday. I wouldn't say I have the sharpest of memories, but the nightmares that frequent my sleep seem determined to keep the details of that day fresh in my mind.

For most people, the first day of prison is an exciting opportunity to reunite with friends and start a new year with a clean slate. I'd be lying if I said I didn't experience a slight amount of excitement that year, but what little bit I did enjoy was mostly trumped by fear of the unknown.

I knew that while almost everyone attending that day would be happy to see each other after a short parole break, I would be enduring the strange feeling of knowing nobody, as it was my first day at a new prison.

I held myself together, even as a big red-dicked man made fun of my virgin asshole and glasses. To make matters worse, I had only just transferred to town a mere two weeks prior, leaving all of my friends behind and hundreds of miles away. Needless to say the ride to jail that day was full of half-hearted optimism and feelings of homesickness and depression. Still, I remember feeling determined not to get raped, assuring myself things would work out for the best.

As I walked into the building for the first time I was very nervous and thought about turning around and running home. It took some courage, but I managed to convince myself that I was going to be fine and that all of my worries were simply in my head. After all, my biggest fear was getting beat up at lunch, an occurrence that I had to witness happen to anyone on any of my other first days of prison.

It wasn't long until I walked up to my new cell, pushing aside the bad thoughts and focusing on being optimistic. Before I walked in, I took a second to assure myself that I was going to make a bunch of new friends and that the prison term was going to be great. Then I picked my head up and marched into my new cell.

It didn't take more than a second or two for my fears to be validated, because as I walked into the room, all of the inmates in the jail started pointing at me and whistling as if I was some piece of meat. It was almost as if they had planned it all along, because the uproar of cat calls could only be compared to what I saw at a surprise party we once threw for my grandpa. Nonetheless, I pressed forward with determination.

I held myself together, even as a big red-dicked man made fun of my virgin asshole and glasses. But then an even bigger man ran up behind me as I took my seat and ripped my pants right off of my ass. He proceeded to pull his cock out and began shooting its contents as he dropped the rest of my pants on the floor. And finally, in true bully form, he finished, didn't kiss me or say goodbye, shattering my rectum (along with my feelings) into pieces.

I could not believe how mean these guys were to me, when I had done nothing to them. I tried to ignore it, but panic began to fill my entire body and I could feel the tears welling up in my eyes. As hard as I tried to fight it, it was no use. Once I started crying, I fell apart and ran out of the room as fast as I could.

I had no idea where anything was, so I just took off and followed the hallway wherever it would take me. I ran past several cells but it seemed like nobody even noticed me, so I just kept running until I found the warden's office.

I burst through his door while he was on a phone call and tried to tell him what had happened, but I was so hysterical that he couldn't understand me. He told the person he was talking to he would call them back and hung up the phone. He grabbed me a glass of water and told me everything would be fine. He tried to calm me down by having me take deep breaths.

I explained to him how mean these men were, and slowly I regained some composure. After about ten minutes of watery eyes and sniffles, he managed to get me to stop crying, and made me realize that I might be overreacting a bit. He handed me a tissue and I wiped away the blood, thinking I had cried myself out.

Unfortunately that wasn't the case, because it wasn't more than two minutes later that I started balling again when he told me he didn't think I was cut out to be a guard at his prison.

All "First Day of…" Aristocrats-style articles:

My First Day of School

My First Day at Prison

My First Day at the Cemetery

My First Day at Alcoholics Anonymous

My First Day of Senility

My First Day of Church

My First Day of School, Part 2

My First Day of Fat Camp

My First Day at the Circus