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Gay Stories
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Bi-Sexual Male / 50
When I was a kid I masturbated heavily, the earliest I remember was when I was about 6 or 7. My mother found me
pillow fucking and tried to stop me. Of course I couldn't stop and as I grew up daily masturbation was a part of my
life, often several times a day and night. I managed to keep my habit secret, often going into the woods near my home to play with my little prick. I went to a private school and then to boarding school at the age of 13.
Leaving home at 13 to go to a new school is always daunting for a child and boarding school is a strange experience.
On my first day the house master helped me to find my way around and was very friendly, so much so that I lost my fear of my new surroundings. He told me that he was always ready to help me with any problems I might have and that I could visit him in his office at any time. I didn't think that his interest in me was in any way sexual, but I did enjoy his company. He was a lot warmer that my father, willing to put his arm round my shoulders and give me a gentle hug.
At home finding privacy to indulge in my frequent masturbation was easy, but in school it was quite difficult. I could go into the toilets but I would have to be careful not to make any noise. At night it was easier s I could pillow fuck as much as I liked after all the other boys had fallen asleep. There was a rule that boys must not visit the dormitories during the day, but my need to feel the soft pillow underneath me and to masturbate was overwhelming. So I found that I could get to my room without being seen if I was careful.
For some time I got away with my little excursions upstairs but one day my housemaster, Bob, heard me. He had his room on the same floor and near mine. While I was lying on my bed, pants down, gently rubbing myself into paradise, he quietly came into the room. I didn't hear him and the first thing I knew was a hand on my bare bottom, gently feeling and pressing me against the pillow. I looked up and saw him smiling at me. He said 'you are a lovely boy'. I saw him undo his trousers and drop them, followed by his underpants.
He started to fondle his cock. I had never seen grown man's cock before. It looked huge, with all that hair and his big balls, so much bigger than my little thing. I was shocked and stunned my the sight. He kept stroking my bare bottom and than got onto the bed next to me, pressing his very warm penis against my smooth young body. He said ' I dream about you all the time, you are lovely'. He kissed my neck and back and gently rubbed himself against the tight crack between my arse cheeks. His rubbing became more uncontrolled and the inevitable happened, flooding my back with his warm cum. I thought he was peeing over me. I hadn't seen cum before. There was a lot of it. Some ran down on the pillow and some found its way under my bottom, making my little balls wet and slippery. When he had stopped coming he pulled up his pants and trousers and proceeded to wipe up the cum with his handkerchief.
I was overcome with a mixture of shock and fascination, and a strange feeling of fulfilment and pride. It made me masturbate even more and daydream about it, remembering every detail of his lovely big cock and the pulsing feeling as he emptied himself over me.
That night I hardly slept having climax after climax.
The next day he came and found me after school and expressed his guilt about what had happened. He was very sorry and said that it was all wrong and mustn't happen again. If anyone found out he would be in very serious trouble. I tried to reassure him, telling him that I liked it, but it didn't seem to make any difference. After that he avoided me, and when we met he hardly wanted to look at me. He was obviously feeling very guilty that he had had a sex experience with a boy.
Several weeks went by, but nothing changed. I dreamt about him and masturbated too much, wanting to feel that big hot thing against my sensitive body.
One day when I was showering after games, he came into the changing room and was passing my shower cubicle. He stopped and looked at me with the water pouring over my naked young body. Seeing him there made me stiff and I started to masturbate, smiling at him as I did so. The look on his face showed the depth of lust he had for me. He quickly walked away. As I was changing back into my clothes, I took my time so that I was the last boy to leave. He came up to me and said 'would you like to visit me after school?' My head was swimming and I stuttered 'yes'.
As I walked to his room my pulse was racing and I was almost breathless with anticipation, my little prick was rigid in my underpants. When I got to his room he was already half naked. He had taken off his pants and his cock was rigid. I had dreamt of getting my hand round his cock and squeezing it and playing with it. Now it was there waiting for me. He slowly undressed me, kissing my face and lips and whispering that he loved me. When I was completely naked he cuddled me against his hairy body, crushing his thick penis against me. He held me so tight I could hardly breathe. I managed to loosen his clutch and while he was still kissing my face got my hand round his cock. I squeezed it and felt its lovely shape and heaviness. He let me play with it for what seemed to be ages but was probably only a minute or two. Then he cuddled me between his legs and rolled over onto his bed. I was crushed beneath him into the bed clothes as he gently rubbed his lovely thing against my body, engaging my prick in the process.
When he started to cum he was convulsed with uncontrollable passion, warm spunk squirted out of his throbbing cock drenching my chest, even reaching my face in great spurts. He went completely limp and exhausted, repressing his tears and out of his mind with carnal satisfaction. I was covered in cum, and he took some of it and dr**ed it around my little prick and balls. He then held me against him again , gently masturbating me to yet another breathtaking climax. We cuddled for a long time with his slippery warm cum between our bodies. He came again, telling me how much he needed me. I kissed him, and he pushed his tongue into my mouth to be eagerly sucked.
After that second event there was no point in apologies and pretence. I went to his room as often as I could, making sure no-one saw me. We became ever more intimate. His hands were all over me, feeling me in the most intimate way possible. I had no illusions about what he wanted. His fingers eagerly explored my anus, pressing into me and thrilling me in a way that I could never have anticipated. It would only be a matter of a short time before his eager fingers would be replaced by an eager cock. Until then he knew he had to be gentle and tender with me. I had a tight lovely bottom and his cock was big and hard. I thought it would be best to stretch my tight anus with something suitable, and I found a small bottle with a round cap that I could insert into my virgin bottom to prepare myself for that first wonderful fuck. It wasn't as big as his gorgeous thing but it was a start. At night I would push it in and out of my anus as I masturbated.
He had restrained himself during our encounters, not wanting to enter me before I was ready. He was very patient, gently encouraging me into new discoveries with long kissing and cuddling sessions. I had learnt to be very clean and well washed before visiting him. He soon took to tonguing my anus and pushing it into me, overwhelming me with sexual pleasure. He wanted to enter me and fuck me filling me with his wonderful warm cum. I was very impatient to be his eager little fuck. So when he put lubricant into my anus I new the time had come. He pushed his big cut knob against my virgin c**t and gently but firmly pushed against the weak resistance of my inexperienced bottom. I relaxed and suddenly he was inside me for the first time. It hurt slightly but the joy and sensuality overcame any pain. He slowly fucked me, in and out, deeper each time. He was far too far gone to contain himself and after a few thrusts my virginity was swept away in a flood of warm cum.
He always had a big cum load, and he filled my bottom that first time with a massive one. I have a very sensual g spot inside my anus. When I'm fucked a man's knob pushed against it makes me climax uncontrollably. The climax makes my anus tighten round the cock, much to the satisfaction of the guy. He soon discovered that and he knew that I was always going to be his eager slave, never saying no and always ready for him.


