Author's Note: this is the first in a series retelling some of the sexual escapades I had when I was a horny, shameless and slightly perverted teenager. The following is all completely true, but I may delve into fantasy at later points in the series. Also this is my first story on this site so please feel free to leave any constructive criticism in the comments.
Disclaimer: this story took place towards the end of Year 13 (the US equivalent of which being high school senior year) and so all characters are 18 or over.
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We've all been there: a teenager making poor decisions based on lust rather than logic. Am I proud of what I did? Well, maybe not all the background details, but the deed itself? I'd be lying if I said I didn't enjoy telling people the story.
But first, the aforementioned shameful background details. There was a girl who for the purposes of this I shall call Annie. I'm not going to ask you to believe that Annie was the hottest girl in the world etc., but she was fairly good-looking. She had a kind of dark and edgy vibe going on, and had a body type that I love: skinny with an ass. Her tits were -- I would guess -- B or C cup: not huge but a decent handful (although I didn't find that out until later).
When we were together, it was fiery. When it was good it was great, but when it wasn't, the rows were blazing. In the end -- somewhat predictably -- there was one row to many and the paper covering the cracks in our relationship crumbled away.
I couldn't have that. I was hormonal, angsty and most of all horny. Luckily enough, I had a friend who was interested in me. It was a shameful rebound, but I was 18 years old and a virgin (the age of consent in the UK being 16), so I was on a mission.
Unfortunately, she was very Christian, and completely dedicated to saving herself for marriage. After a few months with not even a kiss, I found myself being drawn back to Annie. She, for her part, was more than willing to accommodate me.
I remember the night it began very specifically; it was the night before Valentine's Day. We got to chatting over text about this and that and the situation escalated. I'm not sure how it happened, I think we egged each other on to be honest, but before I knew it we were sexting. We told each other all the filthy things we were going to do to each other.
Of course it was wrong. I know that, I knew it at the time, but kidded myself otherwise. It wasn't even that, I just kept the two things apart in my mind. It was as if the version of me that was in a relationship and the version that became friends with benefits with Annie were two different people. I do truly regret it though.
Regardless, in hindsight it's clear that this state of affairs could never be sustained, but I wasn't thinking ahead. It all came to a head on our drama performance day. For context, we were both studying A level drama, and the way the performances were assessed was in one performance day, where each group took it in turn to put on their performance in the school 'drama hall' (auditorium) while the rest -- and whichever students from younger years were meant to have a drama lesson at that point -- comprised the audience.
Our sexting had become increasingly unsubtle -- including me telling her to bring herself to orgasm during a lesson -- and on this day she wore a dog collar (vaguely disguised as a choker) to school on my instructions. This turned us both on, and the situation was exacerbated by my giving her ass a quick squeeze as she went up the stairs ahead of me.
We took our places for the day, and we were sat on the back row (in fact, I was put in charge of operating the camcorder on a tripod at the back of the seats that recorded the performances). No sooner had the lights dimmed than my hand was back on her ass, squeezing and caressing her curves.
I stayed outside of her jeans for about five minutes before my hand slipped inside. I felt her soft flesh on my hand as she looked determinedly at the stage. She dared not make eye contact lest any of the people sat around us noticed that something was amiss.