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 love academic session to his divorced father. Apparently Rob and his father had a right 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 macho than kick and preferred to be sucked and fuck rather than be fucked. Rob's Dad was always turned on by seeing char or men wearing panty, Rob use to fall apart scanty to please his Dad when they had their jerk off sessions, but Rob preferred wearing underpants and seeing girl or other boys wearing them.

So you can reckon how entranced Rob ‘ s Dad was to hear that Rob's had his own panty wearing little cum slovenly woman. Rob 's father took a great interest and encouraged Rob to fetch me to meet him at their home. I still recall that day, when Rob took me over to his mansion 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 option of panties. He told me Rob said I was the best pantywaist boy he'd ever fucked and wanted him to ploughshare in a bit 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 knight bachelor ; instead of treating me as his great nephew he preferred me to be his niece, which included learning matter effeminate son 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 principal fetish was cissy male child, and delighted I the fact he found will 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 quotidian till I left domicile at 21 and every meter I was dwelling.

Anyway up till I was fourteen all my intimate play was oral ; I continued my education of orally pleasing a man from my large uncle. Rob's Dad offered to choose Rob and me along for a week of boating, swimming and just fun away from the household. Unknown to me Rob was dropped off at his Mom's firm, 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 dickhead, his constant erections could satisfy any motive woman's lustfulness, Rob's Dad says the woman was a nail 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 distant public gutter, Rob's Dad told me to reave down to my pantie, and espouse him into the toilet.

There were two honest-to-god men and a vernal male standing at the urinal with their jean and underpants dropped down, all three were wanking each former and looking at each other prick, until I came him, Rob asked the men if they wanted a sissy boy sucking.

The fervor and my lustful young couldn't refuse the opportunity to suck three males dick, one of the men was known to Rob's Dad he said"I hope you've brought us a really good dick mark, I was instructed to kneel down and suck the two senior men's cocks, the young guy just watched he slowing masturbating himself, then Rob's Dad asked the younger guy did he want to get laid my sweet ass, Rob ‘ s Dad knew the younger guy's stopcock was smaller than the two previous men's. While sucking two huge succulent cocks, Rob come behind me yanked my skimpy knickers down and started to lubricate my screwing fix by finger fucking my bunghole with his index fingerbreadth. I moaned and groaned with ecstasy, when the young man's cock reached its full erection he guided his cock inside me, this untried man was eager to have intercourse and took full advantage of my boy pussy, wham bang it was for ten instant, not let up just continuous gyration, I'm screamed out a couplet times became my boy cunt became dry, then after the Thomas Young man had ejaculated his cum freight inside me he left quickly left. Rob's Dad was really pleased with me ; Rob's Dad invited the two sr. men in turns to lie with me, by now they were cook to release their surcharge glob, I reached that point I couldn't get adequate rooster inside me.

We left and finally reached our terminus, the first night sleeping I began our usual oral examination games. He told me I was getting almost perfective at pleasing him and other men. He was rubbing me softly saying how beautiful I was. He said I was truly a cancel fucking Milquetoast. He said I was one of only a few with my special endowment. The only difference that night was his new interest in playing with my tooshie as well as my sucking his turncock. He kept rubbing it and running his fingers along the crack stopping at the piffling hole and pressure. He asked me if it was alright and I just nodded in acceptance of this new wonderful tactual sensation. Then I noticed his fingerbreadth was all gooey and his pressure on my kettle of fish was getting loyal. All I could do was press back as it felt so estimable. He then asked me to grow putting my face in front of his turncock. 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 take on, totally with my, as he called it, my sweet puss.

He kept rubbing the modest hole and pushing against it. Each push against it went furthering. Soon I gasped as his digit 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 contract 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 question 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 apparent motion. I may have been nine but I was a withering plenty in sexual pleasure. I never knew something could feel so in effect. He again asked how I felt, and all I could do was groan ever so sapless and nod my head yes. Then he asked if I wanted to do something only a girlfriend could do to please her man. He wanted to put his dick in my slit thus giving myself and my physical structure 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 pansy boy could.

He had me get on my stifle with my cubitus down and my fanny in the air. He again pushed in his finger and by this fourth dimension it was easily going in. He added a second. I was lost in lust even as a young pantywaist boy. He pulled them out and the sudden emptiness saddened me. Then there was a real sharp painfulness. I felt something much heavy 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, tender their physical structure completely to their master. I so wanted to do that that I just had to bear with the stinging and delight him. I needed to show him I was a good footling emasculate by giving him my eubstance for his pleasure he would see and believe it. It took what seemed the like hours but soon I felt his dick haircloth against my behind. 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 head the best sissy he'd ever fucked.

He only got it all the way in when I felt it seem to get boastful and then he said he was sorry, he came. He explained that his cum, the Saame 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 screw 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 consistency and he put in me that talent, 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 tertiary, my bottom was a bit sore but I was just glowing. I could not wait till bed meter 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 sassing. He kept telling me to stop pouting ; all I wanted was to finger 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 prison term of day to get his cock inside me. I was hooked ; I loved as he said `` roll in the hay '' 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 oceanic abyss for as long as he wanted .