I remember the first time I ejaculated.  I remember the first time I masturbated using the traditional method.  I remember having sex for the first time. But before all that, the VERY first thing I ever tryed was fingering my ass.  I was a young boy, curious about my body and I remembering exploring back there while I was taking a bath.  I really didn't know anything but I was pretty sure the way to masturbate was by inserting something into your ass.  Backdoor pleasures soon faded away after I discovered the actual way to masturbate and cum.  After that I was a jacking machine.  My step-father had a subscription to Penthouse and I would always sneek a peek and a tug after school, before my parents came home from work.  Early mornings, early afternoons, any room that was private, outside in the forest, in my car when I turned sixteen. Everywhere and anywhere I could find.  

When masturbations lost it's fun your fucking lonely - Green Day

I was an weird teenage boy.  I didn't really have an indenty and I was being raised in the cliqish 90's. I never really was good with women and really wasn't even getting to first base. I was the king of self love and ruled over my geocities website with fakes of Kelly Bundy. I became bored with it.  I felt like trying something new.  I attempted auto-fellatio several times with little success.  I experimented with "other techniques and practices" but finially I came back around to fingering my ass again.  Boy this was feeling great, why wasn't I doing this more often I thought.  I wanted it deeper than my finger could provide.  I needed a sex toy.  

Ten hours after I turned eighteen (legal purposes lol) I walked into the Adult Video Store and purchased two movies and a pink 5 1/2" anal slim jim and a small bottle of lube.  I was so excited to see what a dildo in my ass felt like.  The first few times it was ackward, and it hurt.  I was unsure what I was doing and usually too stoned to give a shit.  It wasn't that pleasurable.  Eventually anal play would once again fade away and I would return to normal "hunched over monkey jacking to hentai" for me.  It wasn't like I was really getting laid at that time.  Things would soon change though.

To be continued....