I would like to share with you an intense experience that I had when I was younger. I seemed to be constantly horny when I was growing up, and went through the typical masturbation/looking at Playboy magazine sort of thing that most teenage boys do. However, it wasn’t until I had turned 15 that I had my first sexual experience with another person, and it happened in the most unexpected way.
Just to explain, I was a very shy teenager. I remember when I was 14 I had 12-13yo girlfriend (Becky) for a few months. For a few days there we didn’t go to school, instead we sat on her bed together holding hands and kissing. Becky had shoulder length blonde hair and was curvy(but not overweight). I remember looking down as we were sitting there holding her hand, and I had an enormous hard on and a large wet patch had formed on my shorts, but I didn’t take things any further due to my shyness and not really knowing what to do. Hard ons were pretty much a constant for me, and often an embarrassing one at that.
When I look back now I think about all of the opportunities for sex that I missed in my teens. Take for instance the hottest girl (Elizabeth) in my grade. In Economics class I would sit near the window on my own, she and her friend would sit opposite me, and the rest of the class would be sitting facing the teacher. Elizabeth would just about make boys cum in their pants just by looking at her. She was 16 (a year older than me at the time), had curly mousy shoulder length hair, average sized breasts, and what seemed to be an all over tan (I did have that confirmed in class one day, but I’ll leave that for another story). And week after week, Elizabeth and her friend would sit the entire two hour class with their legs spread. Her friend would always wear black panties, but Elizabeth’s were either yellow, red, blue, or orange, the same style with a small nautical emblem on the top left hand corner. I got so horny knowing that I would be the only person in the school who would know what coloured panties Elizabeth was wearing that day. Usually I would go home after school, lie on my bed, and masturbate until I came. On another occasion she bent over right in front of me in the playground and I got to see her tight brown arse, and that provided me with many more orgasms. We never spoke as I was average looking and too shy to approach her.
I vividly remember other things I saw in high school; a 13 yo girl who wore a skirt and sat absentmindedly in the playground with her legs VERY wide open, and the material of her panties could barely cover her hole (the rim of her hole was just about visible). Or the 15yo girl whose skirt was worn so high you could see her bottom and knickers as she was walking. Another 17yo girl who walked around all day without a bra and her dark nipples showing through her lemon top. One opportunity I definitely regret missing was a girl who was 14yo (I was 15 at the time) and she and her girlfriends at lunch were measuring the span of the hands of some of the boys I hung out with (to try to measure the length of their dicks when erect). I didn’t really know much about her. She was one of these girls who seemed to be a bit of a slut to be honest, but she had a nice average sized body, blonde shoulder length hair, and nice soft pale skin. She measured my hand and seemed really surprised; for some reason mine was a fair bit longer than my friends (I had a 7 inch cock at that age, so I suppose it was a fair size). She seemed quite excited about it, kept measuring my hand, and called her friends over to check it all out and make a big fuss. Again, shy me didn’t take it further. At the end of lunch she walked over to pick up her bag and didn’t bother to bend her knees at all, giving anyone who cared to notice (like me) a good long look at just how white and creamy and soft her arse and legs were (she wore black bloomers, which contrasted with her skin tone). I wish now that I’d somehow got to know her well enough to ask if I could go back to her place so we had the opportunity to fuck totally naked on top of her bed without a condom. Maybe she was afraid that her mother might have walked in on us.
However, later that year something did happen. My parents never had that much money when I was growing up, so often I’d have to make do with clothes for a few years until they could afford new ones. This was more of a problem with the shorts I wore, which were extremely tight and a bit embarrassing to wear at times at school. It felt like my shorts were glued on and were pressing right against my crotch and arse all of the time, which was a problem with the many hard ons I got each day. I suppose that the other boys at school who liked boys would have gotten a good eyeful and maybe went home to masturbate over me themselves. Who knows? I didn’t think of it at the time. I was nearing 6 foot tall, was (and still am) slim with white skin. My arse is pretty round and I’ve had plenty of positive comments about it as an adult.
Anyway, the shorts situation became a real issue one night at touch football. We played at a park where there were quite a few games on that night. I was wearing a pair of shorts that were loose but so short that I felt like the cheeks of my arse were on display to everyone, even though I had thin blue underpants on (like a speedo style). I was very self conscious and was hoping that no-one else would notice. I started the game and then spent some time on the sideline to rest. There were no seats so I walked up and down the touchline. It was then that I noticed a man about 35-40yo who was following me up and down the touchline about 10 meters behind. When I stopped to watch the play he would crouch down directly behind me and pretend to watch the play, but I got the sense that he was looking up my shorts instead. I’d never had anything like this happen before and I couldn’t make sense of it. Anyway, I returned to the field but injured myself and had to come off again.
I had never considered having a shower at the ground as the showers in the changerooms are open (there is no door or shower curtain) and are for both sexes, but as the game was still going I figured that no-one else would be in there and I’d be able to get in and out quickly, even though it was in a central position to the other fields.
I went in, checked that no-one was around, and went to the showers. I stripped off down to my flimsy underpants and started showering myself. I had my back to the open doorway of the shower cubicle as I didn’t want anyone else to see the outline of my penis through the underpants as I showered. I was enjoying the shower and lathering my near naked body up when I decided to quickly slip off my underpants and give my penis and arse a quick wash. (I’d also forgotten that I didn’t bring another pair of underwear with me so I had to wring what I had out). As I washed my circumcised penis it grew from being long and very soft to being increasingly big and hard and started to stick straight out in front of me. I turned away from the water to wring out my underwear and turned to face the open doorway when I got the shock of my life. The man who had been watching me before was sitting opposite on the bench next to my bag and clothes, with his hand deep in his shorts and was pulling himself furiously as he watched me. I went bright red and tried to cover up my hard penis with my tiny underpants. He looked at my hard penis sticking out and bobbling about, jerked his body, pulled himself at an even more frantic pace, stiffened completely, and then let out a loud groan (his groan was drowned out by the crowds outside). He withdrew his hand and a dark patch started to form on his shorts. I had to go to where he was sitting to collect my gear and get the hell out of there. However, he had other ideas. As I grabbed my things, he suddenly grabbed my arse with both hands and he pulled my hips towards his face, forcing my hard penis into his open mouth. I felt some of his come on his fingers and he rubbed it into my arse.
I was frozen by the shock of it all. His head moved back and forth as he started to suck me off, putting almost all of my cock in his mouth. I was surprised by how warm, soft and wet his mouth was, considering he was a man. I suppose I was lucky that he was clean shaven. My penis was seriously throbbing in his mouth when I realized that anyone could have walked into the changerooms at that moment and seen what was happening. He then did something that sent me completely over the edge (even though I was sooo scared to do so) – he pushed a finger deep into my hole. My come absolutely exploded into his mouth. It seemed to go on forever and I could barely stand up as my legs were shaking that much. As soon as I started to go soft, he got up and got out of the dressing room as soon as he could.
I was left standing there naked, with cum dripping out of my red, swollen cock, and shaking like a leaf. A woman who was about 25yo walked in and saw me standing there like that, and obviously thought something was wrong. She helped me put my clothes back on, but I couldn’t speak. She helped me out of the changeroom and I made my way home, not telling anyone about it until now. I didn’t think that it was anything bad that had happened to me, more a mix of shock and intense pleasure. I haven’t had sex with a man since, and never again want to have underage sex, but I don’t regret what happened.