I lost my anal virginity when I was fifteen, when one of the schooling prefect's called Rob made me his personal screwing toy. Later Rob mentioned our bang school term to his divorced father. Apparently Rob and his begetter had a good relationship although Rob lived with his mother after his parents were divorced. Rob and his Dad's kinship was a close one mainly due to their high sex drive. Rob and his Dad used to masturbate each other. Rob's use to suck his Dad's peter, but Rob was more dyke than gripe 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 step-in to please his Dad when they had their wanking sessions, but Rob preferred wearing underpants and seeing girl or former boys wearing them.

So you can reckon how delighted Rob ‘ s Dad was to learn that Rob's had his own panty wearing little cum slut. Rob 's father took a peachy involvement and encouraged Rob to land me to meet him at their home. I still think of that day, when Rob took me over to his house and introduced me to his don, Rob quickly left leaving me alone with his father, who led me to the upstairs sleeping room where there on his bed all laid out were a beautiful natural 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 delight toy was no surprise for me, my cracking Uncle had helped broach 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 letdown 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 rest home at 21 and every time I was home.

Anyway up cashbox I was fourteen all my sexual play was oral ; I continued my education of orally pleasing a man from my majuscule 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 menage, Rob's Mom was away so Rob had arranged for an sr. married woman to stay with him the weekend, Rob being a Thomas Young horny studhorse with an instable penury for sex whether it was a cunt or an dickhead, his constant erections could fulfil any need woman's lecherousness, Rob's Dad says the woman was a complete nymphomaniac, and that he's also fucked her lots of fourth dimension, Before Rob left us he turned to me and said I'd good meet 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 outback populace toilet, Rob's Dad told me to pillage down to my panties, and follow him into the toilet.

There were two aged men and a vernal male standing at the urinal with their jeans and underpants dropped down, all three were wanking each other and looking at each other tool, until I came him, Rob asked the men if they wanted a sissy boy sucking.

The inflammation 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 untested guy just watched he slowing masturbating himself, then Rob's Dad asked the youthful guy did he want to roll in the hay my angelic ass, Rob ‘ s Dad knew the younger guy's cock was smaller than the two old men's. While sucking two huge succulent hammer, Rob come behind me yanked my skimpy knickers down and started to lubricate my hump hole by digit fucking my asshole with his index finger. I moaned and groaned with raptus, when the young man's shaft reached its full erection he guided his cock inside me, this young man was eager to roll in the hay and took full advantage of my boy pussy, wham bang it was for ten minutes, not let up just uninterrupted gyration, I'm screamed out a pair times became my boy cunt became dry, then after the young man had ejaculated his cum onus 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 gear up to exhaust their overloaded balls, I reached that breaker point I couldn't get enough cock inside me.

We left and finally reached our destination, the first Nox sleeping I began our usual oral game. He told me I was getting almost perfect at pleasing him and former men. He was rubbing me softly saying how beautiful I was. He said I was truly a natural roll in the hay sissy. He said I was one of only a few with my special gift. The sole deviation that dark was his new interest in playing with my derriere as well as my sucking his dick. He kept rubbing it and running his finger along the crack stopping at the piffling 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 press on my muddle was getting unfluctuating. All I could do was conjure back as it felt so good. He then asked me to turn putting my aspect in front line of his dick. He wanted me to soak up him as he had taught me. I loved doing this and went right at it. His prick was always welcomed in my mouth. He then reached around and continued to work, totally with my, as he called it, my sweet-smelling kitty.

He kept rubbing the pocket-sized hollow and pushing against it. Each push against it went furthering. Soon I gasped as his finger went fully in. This all took spot over an hour. So he took over an time of day to loosen me up enough to advertise his finger in. It surprised me but soon I just could not centralise on sucking, only on what I was feeling back there. I was lost in a pleasure I 'd never matt-up 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 charge. He asked how it felt and all I could do was groan. I wanted more. He put More of whatever he was using on his finger and pushed it in all the way in one libertine motion. I may suffer been nine but I was a withering mass in sexual pleasure. I never knew something could finger 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 daughter could do to please her man. He wanted to put his cock in my pussy thus giving myself and my consistence 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 Milquetoast boy could.

He had me get on my genu 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 endorsement. I was lost in lustfulness even as a young sissy boy. He pulled them out and the sudden vacuum saddened me. Then there was a tangible 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, declare oneself their body completely to their master. I so wanted to do that that I just had to give birth with the stinging and please him. I needed to show him I was a safe little sissyish by giving him my body for his pleasure he would see and think it. It took what seemed like time of day but soon I felt his dick hairs against my posterior. He was leaning over kissing my backbone. 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 practiced sissy he'd ever fucked.

He only got it all the way in when I felt it seem to get giving 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 turncock was now in me as it should be. He said that he had fucked me as a man should have it off a girl and filled me with his cum. He had me rolling wave over still with his dick 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 torso and he put in me that gift, a gift both he and my Uncle always said was a man 's gift to his young lady. I slept so soundly that dark as I knew no subject 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 Nox he said I should give my pussycat sleep, so I sucked him till he came in my mouth. He kept telling me to terminate pouting ; all I wanted was to feel him in me again. Too filling me with his cum. Well the remainder of the weekend there I did everything I could no count what clock time of day to get his pecker inside me. I was hooked ; I loved as he said `` fucking '' He told me I was a lifelike. From that day till I was in my mid-twenties I loved him and loved him deep in me, fucking me farsighted punishing and rich for as long as he wanted .