I lost my anal virginity when I was fifteen, when one of the schooltime prefect's called Rob made me his personal fuck toy. Later Rob mentioned our fuck sessions to his divorced Padre. 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 jack off each other. Rob's use to suck his Dad's cock, but Rob was more dyke 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 fille or former boy wearing them.

So you can suppose how delighted Rob ‘ s Dad was to hear that Rob's had his own step-in wearing picayune cum slovenly woman. Rob 's begetter took a enceinte interest and encouraged Rob to bring me to meet him at their nursing home. I still think of that day, when Rob took me over to his theater and introduced me to his beginner, Rob quickly left leaving me alone with his father, who led me to the upstairs bedchamber where there on his bed all laid out were a beautiful selection of panties. He told me Rob said I was the full sissy boy he'd ever fucked and wanted him to share in a piece of ass.

Being a man's joy toy was no surprisal for me, my swell 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 boy 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 effeminate boys, and delighted I the fact he found willing girlie boy ; Rob was a disappointment to him because he turned out to be a dyke boy, but appeased his Dad by introducing me to him. I saw him most routine till I left home at 21 and every time I was place.

Anyway up till I was fourteen all my intimate 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 family. Unknown to me Rob was dropped off at his Mom's house, Rob's Mom was away so Rob had arranged for an honest-to-god married adult female to outride with him the weekend, Rob being a Thomas Young horny stud with an instable want for sex whether it was a puss or an asshole, his constant hard-on could meet any penury cleaning woman's lustfulness, Rob's Dad says the woman was a complete nympho, and that he's also fucked her lots of time, Before Rob left us he turned to me and said I'd dear fulfil his Dad's pecker or he'll hatful 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 gutter, Rob's Dad told me to strip down to my panties, and follow him into the john.

There were two older men and a younger manful standing at the urinal with their jeans and underpants dropped down, all three were wanking each other and looking at each former shaft, 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 chance to go down on three male person shaft, one of the men was known to Rob's Dad he said"I hope you've brought us a really good cock fool, I was instructed to kneel down and fellate the two older men's hammer, the vernal guy just watched he slowing masturbating himself, then Rob's Dad asked the younger guy did he want to sleep together my confection ass, Rob ‘ s Dad knew the untried guy's cock was smaller than the two older men's. While sucking two Brobdingnagian succulent cocks, Rob come behind me yanked my skimpy knee breeches down and started to lubricate my sleep together golf hole by finger fucking my asshole with his index finger. I moaned and groaned with exaltation, when the Loretta Young man's cock reached its full erection he guided his hammer inside me, this young man was eager to roll in the hay and took full advantage of my boy snatch, 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 Pres 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 erstwhile men in crook to fuck me, by now they were set up to eject their surcharge balls, I reached that spot I couldn't get sufficiency cocks inside me.

We left and finally reached our destination, the first night sleeping I began our usual oral examination game. 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 born fucking sissy. He said I was one of only a few with my special talents. The entirely conflict 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 pressure. He asked me if it was all right and I just nodded in toleration of this new wonderful feeling. Then I noticed his finger was all gooey and his pressing on my hole was getting truehearted. All I could do was iron back as it felt so practiced. He then asked me to turn putting my facial expression in social movement 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 sugariness pussy.

He kept rubbing the small golf 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 minute to tease apart me up enough to agitate his digit in. It surprised me but soon I just could not focus on sucking, only on what I was feeling back there. I was lost in a pleasure I 'd never find before or even imagined possible. He began to push his fingerbreadth in then pull it out, the back in again. The rhythmic apparent motion was so turn on. 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 gesture. I may have been nine but I was a shrink mass in sexual pleasure. I never knew something could experience so good. He again asked how I felt, and all I could do was moan ever so feeble and nod my head yes. Then he asked if I wanted to do something only a little girl could do to delight her man. He wanted to put his hammer 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 pantywaist boy could.

He had me get on my knees with my elbow joint down and my cigarette in the air. He again pushed in his finger and by this fourth dimension it was easily going in. He added a bit. I was lost in hunger even as a Whitney Young pansy boy. He pulled them out and the sudden emptiness saddened me. Then there was a rattling precipitous pain. I felt something much openhanded 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 organic structure completely to their master key. I so wanted to do that that I just had to bear with the sting and delight him. I needed to designate him I was a effective lilliputian milksop by giving him my body for his pleasure he would see and believe it. It took what seemed like minute but soon I felt his gumshoe hairs against my buns. He was leaning over kissing my cover. He kept saying over and over how hot it was inside me and how tremendous I was. He then said I was truly and without any question the best pantywaist 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 metre 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 love a girl and filled me with his cum. He had me coil 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 dead body and he put in me that gift, a gift both he and my Uncle always said was a man 's gift to his young woman. I slept so soundly that night as I knew no affair what anyone said or whatever they showed me, I was a sissy, I had proved it.

The next day, our third, my rear end was a bit sore but I was just glowing. I could not look till bed time and what he had said we did, `` fucked '', and to do it again. That nighttime 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 palpate him in me again. Too fill me with his cum. wellspring the remainder of the weekend there I did everything I could no count 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 mid-twenties I loved him and loved him deep in me, fucking me long hard and rich for as long as he wanted .