Kelly's Diary 041 - My First Time With a Virgin - Cover

Kelly's Diary 041 - My First Time With a Virgin

Copyright© 2024 by Kelly85

Chapter 1: Meeting Randy

Coming of Age Sex Story: Chapter 1: Meeting Randy - I can't even begin to say how many times I've heard guys dream about sex with a virgin. Well, why wouldn't the same apply to a girl?

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   True Story   First   Oral Sex  

During the beginning of my senior year in high school there was a guy in my church senior high youth group named Randy. He was a sixteen year-old junior so as a seventeen year-old senior I’d not paid him a lot of attention until one night at a youth group meeting. My interests tending to more to guys older than me, not younger.

It was Indian summer so I was wearing a pair of cutoffs that were short but not too short for church with a T-shirt from church camp that was a baggy and really did nothing for my figure. Needless to say I wasn’t wearing a bra but between Mother Nature’s cruelty to me plus the oversized T-shirt it wasn’t all that obvious.

We were sitting in a circle of uncomfortable metal chairs with Randy seated next to me. I smiled to myself as I noticed that he was staring at my legs whenever he thought I wasn’t paying attention. I always get a kick out of how dumb guys can be! Like he actually thought I didn’t notice? Once when I knew he was looking I turned my head quickly and he glanced away, blushing because he knew I’d caught him and he realized that I’d known all along that he’d been looking at me. 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 so it didn’t take much to ratchet up the ol’ Kelly horny index! Besides, if he got rid of the dorky glasses I bet he’d look pretty hot. Randy seemed a bit immature but then what teenage boy wasn’t? After all, that’s why I preferred them older. I’d never even seen him alone with a girl and I doubted he’d ever been on a date.

Later on in the evening we were going to play a scripture quiz game and the girls had to draw names from a hat for their partner. Given what had happened earlier I was amused at Fate’s irony when I pulled out Randy’s name. When I walked over to Randy and showed him the slip with his name on it, he blushed beet red and I couldn’t help but smile.

“C’mon Randy, it’s OK,” I said quietly so the others wouldn’t hear, “I didn’t mind you looking at me. Besides, don’t you know that girls really like it when guys look at them, even if we say we don’t? Why do you think we go through all the trouble to dress up and look good for you guys?”

Randy just stammered a bit so I smiled again at him to try to let him see I was OK with everything. He was beetled though and didn’t seem consoled. We all sat down at our designated tables where I spread out the quiz cards. Our table was off in the corner with nobody was too close to us but it wasn’t like we were alone or anything like that.

As I prepared the cards I started thinking about how he had been staring at my legs and crotch earlier, wondering what he was thinking when he did. Actually i wasn’t too hard to imagine. In my mind I pictured him going home later and laying in his bed all alone in he dark, fantasizing about me and wanting me, wishing he could put his hands on me and feel those smooth tanned legs he’d been staring at. Mmmmmm, I imagined him growing erect and then masturbating as he dreamed of me dropping my shorts and showing him more of me than he’d ever seen of any girl 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 boy. It was then I really started looking at Randy with more than just curiosity or passing interest. What wld he be like if we were alone right now? How it would feel to have him do more than just look at me? I felt my face flush a bit the more I thought about him so I decided learn a little bit more about Randy.

“So Randy, do you have a girlfriend?” I asked as nonchalant as possible so as not to scare him off like a frightened rabbit.

He just shook his head and looked down at his index cards as if he was embarrassed to admit the truth. I felt sort of sorry for Randy as he seemed so insecure with me. At the same time it made him all the more interesting as I wondered what I could do to make him more confident. Sort of like he was now a project for me, somebody to rehabilitate even.

“You know Randy, I’ve never bitten anyone in my life so you CAN talk to me! Is there something wrong with me, some reason that you can’t look at me?”

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