I lost my anal virginity when I was fifteen, when one of the school prefect’s called Rob made me his personal fuck toy. Later Rob mentioned our fuck sessions to his divorced father. Apparently Rob and his father had a good relationship although Rob lived with his mother after his parents were divorced. Rob and his Dad’s relationship was a close one mainly due to their high sex drives. Rob and his Dad used to masturbate each other. Rob’s use to suck his Dad’s cock, but Rob was more butch than bitch and preferred to be sucked and fuck rather than be fucked. Rob’s Dad was always turned on by seeing woman or men wearing panties, Rob use to wear panties to please his Dad when they had their wanking sessions, but Rob preferred wearing underpants and seeing girls or other boys wearing them.
So you can imagine how delighted Rob‘s Dad was to hear that Rob’s had his own panty wearing little cum slut. Rob’s father took a great interest and encouraged Rob to bring me to meet him at their home. I still remember that day, when Rob took me over to his house and introduced me to his father, Rob quickly left leaving me alone with his father, who led me to the upstairs bedroom where there on his bed all laid out were a beautiful selection of panties. He told me Rob said I was the best sissy boy he’d ever fucked and wanted him to share in a piece of ass.
Being a man’s pleasure toy was no surprise for me, my great Uncle had helped initiate me previously, he was an old bachelor; instead of treating me as his great nephew he preferred me to be his niece, which included learning things sissy boys needed to do to please older men. After my Uncle’s passing it was then Rob’s Dad continued to teach me how to be a proper feminine boy, his main fetish was sissy boys, and delighted I the fact he found willing girlie boy; Rob was a disappointment to him because he turned out to be a butch boy, but appeased his Dad by introducing me to him. I saw him most everyday till I left home at 21 and every time I was home.
Anyway up till I was fourteen all my sexual play was oral; I continued my education of orally pleasing a man from my great uncle. Rob’s Dad offered to take Rob and me along for a week of boating, swimming and just fun away from the house. Unknown to me Rob was dropped off at his Mom’s house, Rob’s Mom was away so Rob had arranged for an older married woman to stay with him the weekend, Rob being a young horny stud with an instable need for sex whether it was a cunt or an asshole, his constant erections could satisfy any need woman’s lust, Rob’s Dad says the woman was a complete nymphomaniac, and that he’s also fucked her lots of time, Before Rob left us he turned to me and said I’d better satisfy his Dad’s cock or he’ll deal with me later. Rob’s Dad and I continued our journey he said “It’s just you and me now sissy boy, after a few hours we stopped near a remote public toilet, Rob’s Dad told me to strip down to my panties, and follow him into the toilet.
There were two older men and a younger male standing at the urinal with their jeans and underpants dropped down, all three were wanking each other and looking at each other cocks, until I came him, Rob asked the men if they wanted a sissy boy suck.
The excitement and my lustful youth couldn’t refuse the opportunity to suck three males cocks, one of the men was known to Rob’s Dad he said “I hope you’ve brought us a really good cock sucker, I was instructed to kneel down and suck the two older men’s cocks, the younger guy just watched he slowing masturbating himself, then Rob’s Dad asked the younger guy did he want to fuck my sweet ass, Rob‘s Dad knew the younger guy’s cock was smaller than the two older men’s. While sucking two huge succulent cocks, Rob come behind me yanked my skimpy knickers down and started to lubricate my fuck hole by finger fucking my asshole with his index finger. I moaned and groaned with ecstasy, when the young man’s cock reached its full erection he guided his cock inside me, this young man was eager to fuck and took full advantage of my boy pussy, wham bang it was for ten minutes, not let up just continuous gyration, I’m screamed out a couple times became my boy cunt became dry, then after the young man had ejaculated his cum load inside me he left quickly left. Rob’s Dad was really pleased with me; Rob’s Dad invited the two older men in turns to fuck me, by now they were ready to release their overloaded balls, I reached that point I couldn’t get enough cocks inside me.
We left and finally reached our destination, the first night sleeping I began our usual oral games. He told me I was getting almost perfect at pleasing him and other men. He was rubbing me softly saying how beautiful I was. He said I was truly a natural fucking sissy. He said I was one of only a few with my special talents. The only difference that night was his new interest in playing with my posterior as well as my sucking his cock. He kept rubbing it and running his fingers along the crack stopping at the little hole and pressing. He asked me if it was alright and I just nodded in acceptance of this new wonderful feeling. Then I noticed his finger was all gooey and his pressing on my hole was getting firmer. All I could do was press back as it felt so good. He then asked me to turn putting my face in front of his cock. He wanted me to suck him as he had taught me. I loved doing this and went right at it. His cock was always welcomed in my mouth. He then reached around and continued to play, totally with my, as he called it, my sweet pussy.
He kept rubbing the small hole and pushing against it. Each push against it went furthering. Soon I gasped as his finger went fully in. This all took place over an hour. So he took over an hour to loosen me up enough to push his finger in. It surprised me but soon I just could not concentrate on sucking, only on what I was feeling back there. I was lost in a pleasure I’d never felt before or even imagined possible. He began to push his finger in then pull it out, the back in again. The rhythmic motion was so exciting. He asked how it felt and all I could do was moan. I wanted more. He put more of whatever he was using on his finger and pushed it in all the way in one fast motion. I may have been nine but I was a withering mass in sexual pleasure. I never knew something could feel so good. He again asked how I felt, and all I could do was moan ever so weakly and nod my head yes. Then he asked if I wanted to do something only a girl could do to please her man. He wanted to put his cock in my pussy thus giving myself and my body to the man who lusted after me. I said “yes” so excitedly, all I wanted to do was to please him in whatever way a sissy boy could.
He had me get on my knees with my elbows down and my butt in the air. He again pushed in his finger and by this time it was easily going in. He added a second. I was lost in lust even as a young sissy boy. He pulled them out and the sudden emptiness saddened me. Then there was a real sharp pain. I felt something much bigger that his finger pressing into me. He was rubbing my butt and whispering how wonderful it felt. He was telling me how beautiful I was. This he said was what sissy was meant to do, offer their body completely to their master. I so wanted to do that that I just had to bear with the stinging and please him. I needed to show him I was a good little sissy by giving him my body for his pleasure he would see and believe it. It took what seemed like hours but soon I felt his dick hairs against my butt. He was leaning over kissing my back. He kept saying over and over how hot it was inside me and how wonderful I was. He then said I was truly and without any question the best sissy he’d ever fucked.
He only got it all the way in when I felt it seem to get bigger and then he said he was sorry, he came. He explained that his cum, the same cum I had many times tasted when I sucked his cock was now in me as it should be. He said that he had fucked me as a man should fuck a girl and filled me with his cum. He had me roll over still with his cock up in me and I feel asleep with him in me. As I fell asleep I now knew I truly was a sissy boy I now really believed it. I had taken a man into my body and he put in me that gift, a gift both he and my Uncle always said was a man’s gift to his girl. I slept so soundly that night as I knew no matter what anyone said or whatever they showed me, I was a sissy, I had proved it.
The next day, our third, my bottom was a bit sore but I was just glowing. I could not wait till bed time and what he had said we did, “fucked”, and to do it again. That night he said I should give my pussy rest, so I sucked him till he came in my mouth. He kept telling me to stop pouting; all I wanted was to feel him in me again. Too fill me with his cum. Well the remainder of the weekend there I did everything I could no matter what time of day to get his cock inside me. I was hooked; I loved as he said “fucking” He told me I was a natural. From that day till I was in my twenties I loved him and loved him deep in me, fucking me long hard and deep for as long as he wanted.