I lost my anal virginity when I was xv, when one of the schooling prefect's called Rob made me his personal screw toy. Later Rob mentioned our know session to his divorced father. Apparently Rob and his father had a good family relationship although Rob lived with his female parent after his parents were divorced. Rob and his Dad's relationship was a tight one mainly due to their high sex drives. Rob and his Dad used to fuck off each other. Rob's use to suck his Dad's shaft, 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 adult female or men wearing step-in, Rob use to break scanty to delight his Dad when they had their fuck off 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 take heed that Rob's had his own panty wearing little cum slut. Rob 's father took a cracking involvement and encouraged Rob to bring me to conform to him at their base. I still recollect that day, when Rob took me over to his theatre and introduced me to his sire, Rob quickly left leaving me alone with his Church Father, who led me to the upstairs sleeping accommodation where there on his bed all laid out were a beautiful selection of panties. He told me Rob said I was the best milksop 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 instruct me how to be a proper feminine boy, his main juju 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 workaday money box I left home at 21 and every sentence I was home.

Anyway up money box I was fourteen all my sexual play was oral ; I continued my education of orally pleasing a man from my smashing uncle. Rob's Dad offered to take Rob and me along for a hebdomad 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 older married womanhood to stay with him the weekend, Rob being a young horny stud with an instable want for sex whether it was a snatch or an asshole, his constant erections could satisfy any pauperization adult female's lust, Rob's Dad says the woman was a staring nympho, and that he's also fucked her lots of time, Before Rob left us he turned to me and said I'd safe satisfy his Dad's pecker or he'll mickle 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 world toilet, Rob's Dad told me to strip down to my pantie, and stick to him into the crapper.

There were two honest-to-goodness men and a younger male person standing at the urinal with their jeans and underpants dropped down, all three were wanking each early and looking at each other cocks, until I came him, Rob asked the men if they wanted a effeminate boy suck.

The excitement and my lustful younker couldn't refuse the opportunity to suck three male person putz, 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 suckle the two previous men's shaft, the younger guy just watched he slowing masturbating himself, then Rob's Dad asked the vernal guy did he want to have it away my Sweet ass, Rob ‘ s Dad knew the younger guy's stopcock was littler than the two older men's. While sucking two huge succulent cocks, Rob come behind me yanked my skimpy knee pants down and started to lubricate my fuck hole by finger fucking my asshole with his forefinger finger's breadth. I moaned and groaned with ecstasy, when the young man's shaft reached its to the full erection he guided his cock inside me, this young man was eager to fuck and took fully 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 pussy became dry, then after the young man had ejaculated his cum freight inside me he left quickly left. Rob's Dad was really delight with me ; Rob's Dad invited the two older men in turns to fuck me, by now they were ready to release their overcharge clump, I reached that point I couldn't get enough rooster inside me.

We left and finally reached our finish, the first dark sleeping I began our usual oral biz. 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 piece of ass sissy. He said I was one of only a few with my extra talents. The only if divergence that night was his new interest in playing with my posterior as well as my sucking his prick. He kept rubbing it and running his finger's breadth along the crevice stopping at the little pickle and pressing. He asked me if it was alright and I just nodded in toleration of this new wonderful spirit. Then I noticed his finger's breadth was all gooey and his pressing on my jam was getting firmer. All I could do was exhort back as it felt so undecomposed. He then asked me to grow putting my face in front of his putz. He wanted me to fellate 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 honeyed pussy.

He kept rubbing the minor mess 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 tease apart me up enough to push his finger in. It surprised me but soon I just could not centralise on suction, only on what I was feeling back there. I was lost in a pleasance I 'd never mat before or even imagined potential. He began to push his digit in then draw it out, the back in again. The rhythmic motion was so exciting. 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 fingerbreadth and pushed it in all the way in one fast apparent motion. I may suffer been nine but I was a annihilative mass in sexual pleasure. I never knew something could sense so serious. He again asked how I felt, and all I could do was groan ever so feeble and nod my head yes. Then he asked if I wanted to do something only a girl could do to delight her man. He wanted to put his pecker 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 cubital joint down and my butt 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 pansy boy. He pulled them out and the sudden vacuum saddened me. Then there was a tangible sharply pain. I felt something much bigger that his finger pressing into me. He was rubbing my butt and whispering how fantastic 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 point him I was a honorable little sissy by giving him my torso for his joy he would see and believe it. It took what seemed like 60 minutes but soon I felt his putz hairsbreadth against my tail end. He was leaning over kissing my vertebral column. 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 enquiry 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 whorl 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 pantywaist boy I now really believed it. I had taken a man into my soundbox 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 subject what anyone said or whatever they showed me, I was a sissy, I had proved it.

The next day, our third, my rear was a bit sore but I was just glowing. I could not wait till bed prison term and what he had said we did, `` fucked '', and to do it again. That night he said I should give my pussy relaxation, so I sucked him till he came in my mouth. 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 sentence of day to get his pecker inside me. I was hooked ; I loved as he said `` piece of tail '' 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 intemperately and cryptical for as long as he wanted .