I was very lucky to have been able to learn a lot about anal sex at an early age. I was at boarding school and struck up a relationship with a local farmer, this wonderful relationship was based around me dressing up as a 15 year old girl/sexpot and experimenting with him fucking me.
The process of anal sex took a while to sort out as I found the way to relax myself enough to let him slide his cock into me and I luxuriated in the sex itself, finding ways in which he could make it easier to get his cock into my tight young arse. This was the days before sex education so it was a little of the blind leading the blind! We even questioned whether anal sex would dangerous or not and simply not possible although instinctively I was deeply drawn to it and it was his research efforts, sending of for some books on erotica that we discovered it was something widely practiced over centuries by men and boys! Talk about naive!
Every Saturday afternoon the school thought I was going to his farm to perform social duties in helping the local people who lived around the school by being useful and socially aware. In reality I would be let into his farmhouse and immediately bound upstairs to slip into a little mini-dress, stockings and suspenders and would then play games around the house ending up with him fucking me bent over some item of furniture or on the floor my legs curled around his back or me gently sucking him off. It was an enormous stroke of luck that at this tender age of 15 my latent transgenderism was allowed to blossom in a relatively safe atmosphere and with a kind and gentle lover.
We did not have the internet so he bought all my clothes by mail order catalogue and in a few weeks I had a decent wardrobe of both clothes and underwear and a small collection of make-up. I also learnt the hard way about make-up removal……after one of our sex sessions finished and having to brutally wash and scrub my face to remove the make-up in order to go back to the school. I learnt later which removal creams worked best and made things a little easier on my face, avoiding the embarrassment of standing in line for the evening meal with bright red cheeks and lips from scrubbing them so hard, thinking everyone would be looking at me and thinking I still had make-up on!
This was all brilliant and very sexy but during the week I ended up servicing more than my lovely farmer boyfriend, as my school mates discovered the joys and sensual pleasures of my pert rounded little bottom.
We all lived in a set of old school buildings and there were between 12-20 boys in each dormitory. My dormitory was an odd shaped as it was effectively in the attic of the building. My bed was in an L shaped dog-leg near the dorm entrance and so effectively cut of a little from the rest of the boys in the dorm. One of the more senior boys in my middle house had developed a bit of a lustful passion for me. I was a slim, androgynous and pretty boy and the school, in a sudden convulsive leap into the 20th century, decided to allow us to grow our hair long. The year was 1967 and England and London were ‘swinging’ frantically, so deep in the heart of the English countryside I was able to grow my hair, which made me look even more effeminate.
There was one boy who kept pestering me, with alternate declarations of lust and then if I didn’t respond with threats of violence, a pattern I’m sure many boys who went to public boarding schools will recognise. For my personal safety and to avoid the bullying where possible I quickly became adept as using my androgynous sexuality to get the bigger boys to fancy me and as a side-effect look after me or protect me from the worst of the bullying. I became an expert masturbator of proffered cocks, reaching into trousers and underwear to quickly bring boys off with expert fingers and a good understanding of how the male penis and balls worked and where the most sensitive parts of the cock were and susceptible to expert fondling.
Things quickly escalated so after prep one evening I was behind the gymnasium with three older boys who took their turn having pulled my trousers and underwear down, to push their eager stiff young cocks between my thighs from behind and to fuck the tight gap between my legs till they grunted and came and a spray of their spunk would jet out in front of me, sometimes splashing my shoes.
This carried on from some weeks but all the while I was also getting wise to actual anal intercourse with my lover every weekend, then on a Wednesday afternoon in the silent and deserted school squash court, my biggest paramour and tormentor! Took me and cornered me for a another dummy sex session.
I was pushed against the wall and with him behind me and he soon had pulled down my shorts and pants and was ramming his stiff little erection backwards and forwards again between my thighs. A lot of his precum was getting smeared all around my crotch and between the crack of my buttocks and to make it more comfortable I helped by spitting on my fingers and generally lubricating the whole area around the top of the insides of my thighs and into the tight sphincter of my anus.
He kept his thrusting up and then suddenly pushed me over, so I was bent at the waist….at that moment the head of his cock slipped upwards slightly and as if guided by the natural concave shape of my bottom, he slid in one movement into my arse, accompanied by a taut yelp from me in surprise and pain.
He suddenly stopped his thrusting as the sensations coming from his cock told him that something was different and he realised that he was no longer dry humping me but had his cock completely buried in me to the hilt. The pause in his movements helped me relax and allowed my sphincter to stretch around this hard shaft that was buried in me. The relaxing was something I had learnt to do with my boyfriend so when he suddenly resumed his thrusting I was not taken by surprise, except for the fact that after about ten more thrusts this new sensation of actually fucking me proved too much and he came copiously. I felt the sudden wet warm feeling deep inside my buttocks as he moaned and thrust and squirted his sperm into me.
That was how it started really! after first real school fuck I was in bed in my dormitory and had dozed off when I suddenly felt a hand reaching under the bedclothes, feeling around my crotch.
It was my friend from the squash court, who clearly had been in bed getting horny and decided he’d come along and have a bit more of my soft little bottom. I knew there was not much point in making a fuss as there was always the inherent threat of violence if I did not comply with his desires, so I rolled over and pushed my bottom out towards the edge of the bed and loosened the pyjama trouser cord around my waist. The beds in our dormitories were ancient and luckily were actually very high of the ground so my eager young schoolboy lover was standing next to my bed with my rear at his waist height!......perfect to allow him to lean forward and angle his cock into me again.
I felt a wave of relief as I was preparing to be painfully and dryly penetrated again, when I heard a jar-top open and he fingered a large dollop of cold sticky Vaseline into my tight little hole, preparing it for his hard and bouncing cock that now stood straight out of his pyjamas in front of him and was pointing at my bed.
I made the foetal position and angled my buttocks out towards the edge of the bed and after some fumbling and some whispered cursing; I felt the hot tip of his cock in the cool night air push against my hole. After some combined pushing I felt him slide smoothly into me and I felt that strange pang of desire as I answered my instinctive femininity and moved under the spell of a lustful male mating with me.
At first his excited thrusting made my bed squeak and bang a little, enough to slow him down and change the angle of penetration in an attempt to reduce the clamour of the noisy bed. It wasn’t a major problem as yet again he was ejaculating into me in about half a minute, whereupon he quickly withdrew his hard pink sticky cock, splashing my sheets with the cum that dribbled out of my arse and he slid off into the dark back to his own dormitory.
That was the begging of a new phase in my sexual life at school as the following night after he had repeated using my arse to fuck and cum in again, a friend of his followed about five minutes later to repeat the process and fuck me a second time. I was now becoming a youthful cum slut and was fucked each night by him and two of his mates. Luckily they all came very quickly so my poor little arse was not damaged or stretched enormously by these repetitive, nocturnal, sticky, fucks and even though they were young their eager cocks were not that large so I could take all this sex without any harmful damage to my insides.
I became adept at relaxing myself and then when they were inside me and buried in my youthful boi-cunt, I found that if I repeatedly and rhythmically squeezed my arse tight it helped to speed up their orgasms.
The drawback to all this sex was that my bed ended up smelling of sperm and my pyjama trousers and bottom sheet were always soaked with large wet patches of youthful sperm that leaked copiously out of my twitching little rear. Heaven knows what the domestic staff must have thought, that so much nocturnal emission could come from one boy!
In time things moved on at school, as they do, but I learnt a lot about anal sex in those couple of years and I am rather smug to say that I probably helped corrupt about ten other pupils who learnt to become addicted to my androgynous slim body and who no doubt suffered a little in later life, either passing their infatuation off as a young sexual obsession or, as I found out later in life, becoming fully functioning gay men, while I carried along my lonely path trying to be as close to being female as I could make myself.
One of those boys did stay friends after we left school and eventually I went out with him for a while when we were in our early twenties. He took me out to a discothèque one night, (in those days I easily passed) in a little black Biba dress with my own hair grown long and styled, tottering out on high heels, I am proud to say he was utterly entranced, proclaiming total love for me and perhaps a little cruelly I had the satisfaction of turning the tables and dumping him after he had declared that sex with me had been the best thing he had ever experienced!……….the final score…..Andrea 10 guy 0!!!