Chapter 1: My Past With Randy

Note: There are a few diary entries from way back me and Randy so I won’t repeat everything here. If you’re interested, you can read about us back then in:

My 1st Time With a Virgin
Fooling Around at My Boyfriend’s House
Caught by My Boyfriends Sister
Way back during the beginning of my senior year in high school there was a boy in my church senior high youth group named Randy. I was a seventeen year-old senior while he was just a sixteen year old junior. Younger guys, especially those younger than me, typically weren’t all that interesting to me so he never caught my attention until one fateful evening at a youth group meeting.

I was wearing my typical denim shorts (short but not TOO short for church) with an old church camp t-shirt that was a baggy and really did nothing for my figure. All in all, I was wearing the about the same outfit as most of the other girls.

At one point Randy was sitting next to me and I couldn’t help but notice that he was staring at my legs whenever he thought I wouldn’t notice (why do guys always think they can get away with that?) Once when I knew he was looking, the next time I turned my head quickly toward him and he glanced away, blushing because he knew that I’d caught him. Actually I thought his shyness was sort of cute and in a way it turned me on a bit. At the time I wasn’t seeing anyone in particular and besides, if he got rid of the dorky glasses I bet he’d look pretty hot. Maybe it was because he was so shy, but I’d never seen him alone with a girl and I’d never heard of anyone dating him.

Later on in the evening we played a scripture quiz game. The girls drew names from a hat and wouldn’t you know it but I pulled out Randy’s name to be my partner. Our table was off in the corner with nobody was too close to us but it wasn’t like we were alone or anything even close to being like that. Still, I found myself thinking about how he had been staring at my legs and crotch earlier, wondering what he was thinking at the time.

In my mind, I pictured him going home later and laying in his bed all alone at night, fantasizing about me and wanting me, wishing he could put his hands all over me and feel those smooth tanned legs he’d been staring at all night. I imagined him getting this wonderful erection and then masturbating himself as he imagined me dropping my shorts and showing him more of me than he’d seen before.

Sitting so close to him now, I started to get that feeling deep inside, that irresistible itch that can only be truly satisfied by a man. It was then that I really started looking at Randy with more than just curiosity or passing interest. What he would be like if we were alone? How it would feel to have him do more than just look at me? How big was his dick? Had he ever fucked a girl with it? Heck, had anyone even sucked it yet?

As it turned out, I managed to coax him into asking me out on a date (actually I think I did most of the asking, he just agreed with what I said). It was fun for me because I’d never dated a virgin before, let alone a guy who hadn’t even been past first base! We went to see a movie and I like to think that he still gets an urge to masturbate whenever he remembers what I did to him that night. Long story short ... Randy wasn’t a virgin when he returned home! What made it special for me was that he was my first virgin. I’d never been fucked by a guy doing his first girl before so he’ll always hold a special place in my memories.