First time sex – Boarding School initiation


I was sent to a boarding school in Yorkshire when I was 13. I was sexually innocent and although I got regular erections I had never ejaculated and knew very little about it. The school house I was in had a dormitory with four corridors radiating from a central hallway with washrooms. Each corridor was separated into cubicles by wooden partitions, which gave some privacy although there was an opening in the top half of the door so that prefects and masters could check on us during the night. Each corridor was presided over by a prefect who had the cubicle nearest the hall. Everyone went to bed at 9pm, lights out. As soon as the lights were out the corridor was filled with the sound of squeaking beds in what I later learnt was a wanking race. Each boy would slap his belly three times to signal his ejaculation, it all only lasted a few minutes! After a week or so, one of the older boys called Mick said he hadn’t heard any noise from my cubicle and did I even know how to wank? I had to admit I didn’t. “Never mind” he said, “It’s time for your initiation and you’ll learn all about it then.” He told me that our prefect would visit that night and I’d better do what I was told. I went to bed nervous and worried about what might happen. Soon after lights out my cubicle door opened and the prefect walked in wearing his dressing gown. He pulled my bedclothes aside and gruffly told me to lie on my belly. He yanked my pyjama bottoms down then I felt his heavy weight land on my back. He …

shuffled about a bit then his hard cock slipped into my bum crack. “What’s going on?” I cried. “Shut the fuck up” he said, then started humping, sliding his cock up and down between my bum cheeks, grunting all the while, Suddenly he stiffened and groaned and I felt a sticky wetness spread over my bum. He rolled off and left without a word. I went to the washroom to clean up, confused about what had happened but also with a slight tingle of excitement which I didn’t understand. Next day Mick asked me how I was. “OK” I said. “Well you’re a quarter of the way through, the other prefects want a go too” he said. “Do I have to do this?” “Yes, we all had to, it’s part of of life here” he said. That night my door opened again and another prefect walked in. He smiled at me and sat down on my bedside chair. He asked me to take off my pyjamas and lie down on top of my bedclothes, I noticed he was rubbing his crutch as he watched me. “I’m told you don’t know how to wank” he said, “I’m going to show you.” With that he pulled his dressing gown open and revealed his stiff prick pointing straight up from a dark bush. He put his hand on it and began rubbing it up and down, sliding his foreskin on and off his shiny cockhead. I was fascinated as, being circumcised soon after birth I had never seen anything like it. “Go on, you too” he said, so I started to pull inexpertly on my soft willy. “No, let me show you” he said and took me in his hand and started to squeeze and tug me. I soon became hard …and he put my hand back on my cock, wanting to get back to his own wank. I matched him and rubbed away. It was pleasant, but no more than that. It had more effect on him though, he was watching me intently and wanking furiously. Suddenly he moaned “I’m cumming!”, his legs shot out straight in front of him and white blobs of cream spurted onto his chest. After a moment he cleaned himself up with a hanky and got up to go. “It’ll happen for you soon if you keep practising” he said. I carried on rubbing for a bit, having got quite excited by watching how much pleasure he had got from it. I was getting into the swing of things now so was in bed early and waiting for the next encounter. Sure enough the third prefect soon came in. His nickname was “Hosepipe” and I soon got to realise why! He made me sit on my chair while he lay on the bed. “Wank me off” he said, revealing his huge member. I had to use both hands and even then only covered half of it. My prick was hard and I wanted to touch it but he made me keep both my hands on his monster. I shyly asked him to touch me but he wouldn’t, just urging me to wank him harder. It went on for ages and my arms were aching from the effort. At last he arched his back and shuddered. A small dribble of white cum oozed out of his cock slit …

and that was it. I was learning that not all cums are equal. After he left I wanked away for while but nothing happened. Fourth night and the last prefect. I started wanking before he arrived and when he did he just stood there watching and slowly massaging his crutch. It made me excited and I felt a warm sensation in my middle that I’d never felt before. He was another bum man but much gentler than the first one. He got himself nicely settled between my cheeks then pushed his hand underneath me to grasp my cock. As he rocked he squeezed my cock and I realised I was loving it. He took his time and told me how soft my bum crack was and how sexy it felt. I could feel waves of sensation building up in my prick and balls as he began to speed up. Suddenly he pulled back and rolled me over. “I’m going to spunk on your chest” he groaned and straddled me, his cock pointing straight at my face. I had my cock in my hand, wanking like mad and experiencing sensations I’d never had before. He pulled his foreskin back and shot a huge spurt over my chin. That did it, I saw stars in front of my eyes and my body convulsed as I shot my first ever orgasm, not big but a success at last! After that I practised every night and every morning and it was not long before I won my first wanking race!

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