My Sex Life - Part 7: Puberty SeXStoRY

This is the seventh part of my ongoing, chronological exploration of my growing sexuality from the age of four onwards. Please feel free to visit my profile page to access the other stories if you have not already read them first. Everything written in these stories is true and actually happened as described, although I will admit that my recollection of some events, especially of my feelings and sensations, may be coloured by more recent experiences. But the actual events themselves all took place during my c***dhood. In this episode I will take you through some of the major sexual events that occurred in my life between the ages of 11 and 14, during puberty. When I was 11 I started to go to high school and this broadened my sexual awareness greatly! One day, for some reason that I now cannot recall, I decided to have a go at "anal"! So one afternoon when I came home from school I got an empty wine bottle from the kitchen and took it up to my room and hid it there for later that night. All evening I was fidgeting with excitement at the thought of doing something new and different and I could not wait to be told by my parents to go to bed! When I got there I did not bother putting on my pyjamas, I just stripped off my clothes and got out the bottle. I set it on the carpet at the foot of my bed and slowly lowered myself over it until the neck of the bottle was resting against my tight puckered arsehole. I lowered myself further down on it but I could not get it to go in - and it was starting to hurt! Undeterred, I realised that I needed some lubrication, so I spat on my hand and rubbed it all over the neck of the bottle and my hole, then I lowered myself slowly down onto it once again. This time, with a little push and a bit of pain, it slipped in! - it felt wonderful and a bit sore at the same time! - and I had broken my "anal virgintiy" at the age of 11! (It would take me another 20 years to break it for real, but more of that in a future story!). I slowly moved up and down the neck of the bottle by an inch or so for a little while until my ass got used to it, then I started taking more and more of it into my ass until I was resting my buttocks on the shoulder of the bottle and had all of the neck right up inside my ass - it felt so huge inside me and I wished that my ass would expand enough to be able to get the shoulder in as well, but I did not think I would ever be able to do that! (How wrong I was!). Then I began to bounce up and down on the bottle with greater and greater intensity until the full length of the neck was banging in and out of my ass and my semi-hard cock was bouncing up and off my belly. I grabbed my cock with one hand and began to masturbate as I "fucked" the bottle with my ass and it did not take long before my cock began to jerk wildly in my hand and cum sprayed everywhere! And it was at that point that I discovered the second great thing about anal sex - not only does it just feel great anyway, but when you orgasm your anal sphincter muscles tighten up in time with your spurts of cum and when you have something hard inside those sphincter muscles for them to tighten up around it feels out of this world! What a climax I had that night!! It seemed to last forever and I was physically drained by the time I had stopped producing cum! Then came the bad bit - as this was my first anal experience I had little or no knowledge of how to prepare my ass for penetration and by now the sides of the bottle and my ass cheeks were covered in shit! And not expecting this to happen I only had a few tissues with me to try to clean up - not enough by half, as it turned out. So I had to sneak out of my room naked and go to the bathroom to get more to clean myself up, heart beating fast all the while that someone would come to investigate what was going on! Luckily, no-one did and from then on I made sure I had a plentiful supply of tissues in my room! That bottle and I became very good friends that year... Later that year I decided that now that my ass had lost its "virginity" it was time for my cock to do the same. Not knowing any girls who would be likely to want to try real sex at that age, and at this age being far to shy to even broach the subject with a girl, I had to look elsewhere - and found the answer in my bedroom! I had a large cuddly panda bear that stood about four feet tall, not much smaller than myself at that age! I had named the bear Pandy a long time ago and one afternoon after school I took a pair of scissors and I cut a small slit through the fur and "skin" between its legs. Inside was a load of small foam cubes - its stuffing - which immediately began to fall out! So I got a small plastic bag and inserted it into the slit and sewed it in place around the edges of the cut with a needle and thread. This helped to hold the stuffing inside and would give my cock somewhere unfluffy to nestle in! There was no-one else home at this stage so I decided to lose my "virginity" immediately! I stripped off and, placing Pandy beneath me on the bed, I slowly slipped the tip of my hard cock into "her". The opening was quite tight and forcing my cock through it pulled my foreskin back along the shaft of my cock - the first time that this had happened without me having to pull it back for myself. The feeling of someone (or something!) else doing this to me was incredible! I held my cock there, in the entrance to Pandy's "pussy" and savoured the sensation, then I slowly slid the length of my now rock hard cock up inside her. The tight opening slowly slid down my shaft until it was resting at the root of my cock and gripped me tightly there, while the head of my cock felt like it was pushing up into a void filled with something large and wielding - looking back on it it felt surprising realistic considering the very basic materials I had used and my total lack of personal knowledge of what a real pussy feels like wrapped around your cock. I spat on the shaft of my cock a couple of times to help lubricate it and then I started to push my cock in and out of Pandy's pussy, slowly building up speed. As my thrusts started to get faster the plastic bag inside the pussy started to rustle, but with my saliva as a lubricant it sounded a bit like what I imagined a wet pussy slurping around my hard cock would sound like and this just turned me on even more! With a last couple of hurculean thrusts my cock jeked wildly, my ballsack erupted, and my cock spat huge jets of semen deep inside her. I was in an agaony of ecstacy! My vision clouded over and my mind went blank for a few moments. It was the best orgasm I had ever had up until that stage. When I came around again I can remember thinking that if this was what sex with a cuddly toy was like, how good must the real thing be!! An added advantage of using a plastic bag inside Pandy's pussy - it meant that I could wash it out and use it again and again - and, oh boy! did I ever! After a few months, even with washing, Pandy began to smell like a sperm-filled whore but I used her again and again for years, just replacing the bag every now and then. I finally (and regretably) got rid of her when I was 18! Bottles up my ass and my cock inside Pandy's pussy kept me both busy and happy for a few years, but when I was 14 a new idea poppped into my head which was to stay with me and become a major part of my sexuality for the rest of my life. I wondered what it would be like to wear women's clothes? My s****r by this stage was 22 but a quick rummage around in her bedroom one afternoon after school led me to find her old school gym clothes in a bag at the bottom of her closet - she had for some reason best known to herself kept them even though she had dumped the rest of her old school stuff years before. I took the clothes out of the bag and took them to my room. There was a white t-shirt and socks, a short, green wrap-around skirt and (best of all) a white sports bra and green panties! I stripped off my clothes and slowly slid my s****r's clothes on. I tried the underewear first. The panties really hugged my balls tightly and I enjoyed the feel of the bra around my chest, although it was a curse to fasten it at first! Then I wrapped the skirt around my waist and fastened it with the velcro strap - that felt fantastic!! I've loved the feeling of a short, flared skirt around my thighs ever since! Finally I put on the t-shirt to complete the kit. I walked around the house and admired myself in the full-length mirror in the bathroom, then I went back to my bedroom, pulled my cock from the panties, but left the elastic waistline gripping my balls, and wanked my shaft until I came. Then I quickly put everything back into the bag in my s****r's room before anyone else came home. That was a good wank, but the thing I remember most about it was the feeling of that skirt around my legs! So the next afternoon after school I put my s****r's old gym gear on again. This time I got out my tennis racquet and tennis ball and went out into the side garden all dressed up to hit the ball against the wall of the house. There was a tall, thick hedge around the garden so I was not likely to be seen. I used to hit a ball off the wall of the house all the time, but wearing the gym skirt transformed it completely! I adored the feeeling that wearing it gave me. It gave my legs so much freedom to move. I loved the sensation of the cool air on my bare legs and upon my thighs. I loved the feeling of the skirt swirling around my legs when I ran and I especially adored the feeling of the skirt bouncing up past my waist and exposing my panties whenever I played a jump shot! I loved those clothes so much that I started to wear them every afternoon after school and one day I took a chance that my s****r did not even remember they were there and I hid them in my own room to wear whenever I wanted to, not just when there was no-one else at home. I also vowed that when I was a bit older I would go out and buy myself some women's clothes, real sexy stuff, so that I would have my very own girlie wardrobe with high-heels and dresses and lacy underwear - but more of that in a later episode! It was not long after this that I had my first ever outdoor wank. One afternoon I was hitting the ball in the garden in my gym skirt (as usual!) when I heard voices on the other side of the hedge. My house was on the corner of two roads, the smaller one of which ran up the hill past the side garden to the housing estate behind and then onto the woods beyond that. And walking down this road were five girls that I knew from my school! At first I worried that they might see me in my gym skirt, but the hedge was so thick that unless they tried hard, and knew where to look through it, it was unlikely that they would see anything. I was silent and still now, but because of their voices I knew where to look for them! As they neared the junction and the bottom of the hedge they stopped walking but continued talking. As it began to look like they might be there for some time (they were teenage girls after all!) I pulled my skirt up and slipped a hand down the front of my panties and touched my cock. The bl**d was pounding in my ears as I felt it harden in my hand and I eased it out over the top of the waistband. I was stood no more than 15 feet away from these girls and I had my cock in my hand! They obviously did not know that I was there so I started to wank my cock. As I masturbated I became more excited and as I became more excited I became bolder (something that still happens today and sometimes leads me into many exciting and very risky encounters - more of that in future stories!). I slid my panties off my thighs, down my legs and kicked them off my feet and quickly followed that with my skirt and the rest of my clothes and soon I was standing naked less than 15 feet away from five teenage girls with a stonking hard-on in my hand! I moved silently across the lawn to get even closer to them and to see them more clearly through the hedge, masturbating my cock all the time. At one point one of them turned towards me as she was talking and I nearly died and I stopped moving, as I could have sworn she looked straight at me through the hedge. But although she stood facing me for some time and I was only about five feet away from her and comletely naked, she obviously did not see me and kept on talking. Eventually I began to wank again, masturbating my cock faster and faster, bl**d roaring in my ears at how risky this all was, until finally spraying cum into the leaves of the hedge just a few feet from them! WOW!! I remember tham all to this day, but their names will remain a secret...