I lost my anal virginity when I was xv, when one of the school prefect's called Rob made me his personal fuck toy. Later Rob mentioned our fuck sessions to his divorced forefather. Apparently Rob and his Father of the Church had a good human relationship although Rob lived with his female parent after his parents were divorced. Rob and his Dad's human 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 shaft, 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 woman or men wearing panties, Rob use to wear panty to please his Dad when they had their wanking sessions, but Rob preferred wearing underpants and seeing girls or former boys wearing them.

So you can suppose how enthrall Rob ‘ s Dad was to hear that Rob's had his own panty wearing little cum slut. Rob 's Padre took a great interest and encouraged Rob to play me to see him at their home. I still commend that day, when Rob took me over to his house and introduced me to his father, Rob quickly left leaving me alone with his forefather, who led me to the upstairs bedroom where there on his bed all laid out were a beautiful choice of panties. He told me Rob said I was the secure pantywaist boy he'd ever fucked and wanted him to part in a piece of ass.

Being a man's pleasure toy was no surprise for me, my not bad Uncle had helped initiate me previously, he was an old knight bachelor ; instead of treating me as his neat nephew he preferred me to be his niece, which included learning things sissy male child 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 right feminine boy, his independent fetich was emasculate 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 workaday trough I left domicile at 21 and every time I was rest home.

Anyway up cashbox I was XIV all my sexual playing period was oral exam ; I continued my education of orally pleasing a man from my heavy uncle. Rob's Dad offered to take Rob and me along for a hebdomad of yachting, swim 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 old married woman to persist with him the weekend, Rob being a young horny stud with an instable want for sex whether it was a cunt or an dickhead, his constant erection could satisfy any need woman's lecherousness, Rob's Dad says the adult female was a sodding nympho, 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 sight 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 hour we stopped near a remote public toilet, Rob's Dad told me to leach down to my pantie, and follow him into the toilet.

There were two older men and a jr. virile standing at the urinal with their blue jean 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 sissy boy suck.

The turmoil and my lusty youth couldn't refuse the opportunity to fellate three males cocks, one of the men was known to Rob's Dad he said"I hope you've brought us a really dear pecker sucker, I was instructed to kneel down and give suck the two elderly men's cocks, the untested guy just watched he slowing masturbating himself, then Rob's Dad asked the untested guy did he desire to fuck my sweet ass, Rob ‘ s Dad knew the younger guy's shaft 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 lube my bang jam by finger's breadth fucking my asshole with his indicant finger's breadth. I moaned and groaned with disco biscuit, when the young man's prick reached its wide erection he guided his cock inside me, this youth man was bore to fuck and took entire advantage of my boy pussy, wham bang it was for ten minutes, not let up just continuous whirling, I'm screamed out a couple times became my boy snatch 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 lie with me, by now they were fix to release their overloaded globe, I reached that full point I couldn't get plenty 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 former 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 deviation that dark was his new interest in playing with my posterior as well as my sucking his cock. He kept rubbing it and running his finger's breadth along the fissure stopping at the little hole and pressing. He asked me if it was OK and I just nodded in acceptance of this new wonderful feeling. Then I noticed his digit was all gooey and his pressure on my mess was getting firmer. All I could do was press back as it felt so in force. He then asked me to change by reversal putting my cheek in front of his prick. He wanted me to draw 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 diddle, totally with my, as he called it, my sweet pussycat.

He kept rubbing the minor hole and pushing against it. Each energy against it went furthering. Soon I gasped as his digit went fully in. This all took post over an hour. So he took over an hour to loosen me up enough to bear on his finger in. It surprised me but soon I just could not boil down on sucking, only on what I was feeling back there. I was lost in a pleasure I 'd never finger before or even imagined potential. He began to push his finger's breadth in then pull it out, the back in again. The rhythmic question was so energize. 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 withering mass in sexual pleasure. I never knew something could feel so practiced. 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 puss 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 sissyish 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 lecherousness even as a young sissy boy. He pulled them out and the sudden void saddened me. Then there was a real sharp pain. I felt something much bigger that his finger's breadth pressing into me. He was rubbing my tail end and whispering how marvellous 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 sea captain. 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 dear little Milquetoast by giving him my physical structure for his delight he would see and trust it. It took what seemed like hours but soon I felt his dick hairs against my butt. He was leaning over kissing my spine. He kept saying over and over how hot it was inside me and how marvelous 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 peter was now in me as it should be. He said that he had fucked me as a man should fuck a daughter and filled me with his cum. He had me roster 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 nighttime as I knew no subject what anyone said or whatever they showed me, I was a sissy, I had proved it.

The following 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 hold back pouting ; all I wanted was to finger him in me again. Too satisfy me with his cum. Well the remainder of the weekend there I did everything I could no weigh 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 raw. From that day till I was in my 1920s I loved him and loved him deep in me, fucking me long hard and deep for as long as he wanted .