I lost my anal virginity when I was fifteen, when one of the schoolhouse prefect's called Rob made me his personal piece of ass toy. Later Rob mentioned our hump sessions to his divorced forefather. Apparently Rob and his father had a good human relationship although Rob lived with his mother after his parents were divorced. Rob and his Dad's relationship was a closely one mainly due to their high sex drives. Rob and his Dad used to masturbate each other. Rob's use to breastfeed his Dad's cock, but Rob was more macho than gripe and preferred to be sucked and fuck rather than be fucked. Rob's Dad was always turned on by seeing womanhood or men wearing pantie, Rob use to wear panties to delight his Dad when they had their she-bop school term, but Rob preferred wearing underpants and seeing young lady or other boy wearing them.

So you can suppose how delighted Rob ‘ s Dad was to get word that Rob's had his own panty wearing little cum slut. Rob 's father took a great involvement and encouraged Rob to bring me to meet him at their home. I still recollect that day, when Rob took me over to his house and introduced me to his male parent, 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 option of panties. He told me Rob said I was the Best sissy boy he'd ever fucked and wanted him to share in a musical composition of ass.

Being a man's pleasure toy was no surprise for me, my heavy Uncle had helped initiate me previously, he was an old bachelor ; instead of treating me as his gravid nephew he preferred me to be his niece, which included learning things Milquetoast 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 independent fetish was cissy boys, and delighted I the fact he found leave girlie boy ; Rob was a disappointment to him because he turned out to be a dike boy, but appeased his Dad by introducing me to him. I saw him most everyday till I left dwelling at 21 and every time I was home.

Anyway up till I was fourteen all my sexual play was viva ; I continued my educational activity of orally pleasing a man from my gravid uncle. Rob's Dad offered to consume Rob and me along for a week of yachting, swimming and just fun away from the theatre. Unknown to me Rob was dropped off at his Mom's house, Rob's Mom was away so Rob had arranged for an aged conjoin char to persist with him the weekend, Rob being a young horny stud poker with an instable penury for sex whether it was a cunt or an cocksucker, his constant erecting could satisfy any motivation woman's lust, Rob's Dad says the woman was a complete nympho, and that he's also fucked her lots of prison term, Before Rob left us he turned to me and said I'd better fill 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 remote public toilette, Rob's Dad told me to strip down to my panty, and abide by him into the toilet.

There were two honest-to-god men and a unseasoned Male standing at the urinal with their jeans and underpants dropped down, all three were wanking each other and looking at each former peter, until I came him, Rob asked the men if they wanted a effeminate boy suck.

The fervour and my lustful young 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 tool sucker, I was instructed to kneel down and suck the two older men's cocks, the younger guy just watched he slowing masturbating himself, then Rob's Dad asked the jr. guy did he want to fuck my sweet ass, Rob ‘ s Dad knew the jr. guy's peter was small-scale than the two older men's. While sucking two immense succulent tool, Rob come behind me yanked my skimpy knickers down and started to lubricate my nooky hole by finger fucking my prick with his power finger's breadth. I moaned and groaned with XTC, when the untested man's tool reached its fully erecting he guided his pecker inside me, this young man was eager to do it and took wax advantage of my boy puss, wham bang it was for ten bit, not let up just continuous revolution, I'm screamed out a brace fourth dimension 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 tour to fuck me, by now they were set to release their overladen balls, I reached that point I couldn't get enough cocks inside me.

We left and finally reached our finish, the first nighttime sleeping I began our usual oral exam games. He told me I was getting almost perfect tense at pleasing him and early men. He was rubbing me softly saying how beautiful I was. He said I was truly a innate ass sissy. He said I was one of only a few with my especial talents. The only difference 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 petty hole and press. He asked me if it was alright and I just nodded in acceptation of this new wonderful feeling. Then I noticed his finger was all gooey and his pressure on my hole was getting firm. All I could do was press back as it felt so unspoiled. He then asked me to turn putting my face in nominal head 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 back talk. He then reached around and continued to run, totally with my, as he called it, my sweet snatch.

He kept rubbing the diminished hole and pushing against it. Each energy against it went furthering. Soon I gasped as his fingerbreadth went fully in. This all took place over an hour. So he took over an minute to loosen me up enough to push his finger in. It surprised me but soon I just could not concentrate on suck, only on what I was feeling back there. I was lost in a pleasure I 'd never matt-up before or even imagined potential. He began to crusade his finger in then pull it out, the back in again. The rhythmic motion was so excite. 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 digit and pushed it in all the way in one fast gesture. I may have been nine but I was a withering mass in intimate joy. I never knew something could palpate so good. He again asked how I felt, and all I could do was moan ever so weakly and nod my head teacher yes. Then he asked if I wanted to do something only a miss could do to please her man. He wanted to put his cock in my pussy 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 delight him in whatever way a sissy boy could.

He had me get on my human knee with my elbow joint down and my bottom in the air. He again pushed in his finger and by this time it was easily going in. He added a second base. I was lost in crave even as a Edward Young sissy boy. He pulled them out and the sudden emptiness saddened me. Then there was a real sharp pain. I felt something much vainglorious that his finger pressing into me. He was rubbing my stub and whispering how wondrous it felt. He was telling me how beautiful I was. This he said was what Milquetoast was meant to do, volunteer their trunk completely to their master. I so wanted to do that that I just had to support with the stinging and please him. I needed to express him I was a in effect little sissy by giving him my consistency for his joy he would see and consider it. It took what seemed care hours but soon I felt his peter tomentum against my butt. 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 question the considerably milksop he'd ever fucked.

He only got it all the way in when I felt it seem to get bragging and then he said he was sorry, he came. He explained that his cum, the same cum I had many meter tasted when I sucked his hammer was now in me as it should be. He said that he had fucked me as a man should make love a lady friend and filled me with his cum. He had me roll over still with his putz up in me and I feel asleep with him in me. As I fell asleep I now knew I truly was a epicene 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 little 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 future day, our third, my bottom was a bit sore but I was just glowing. I could not hold off till bed fourth dimension 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 block pouting ; all I wanted was to feel him in me again. Too fill me with his cum. well the residuum of the weekend there I did everything I could no weigh what time of day to get his shaft 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 20 I loved him and loved him deep in me, fucking me tenacious toilsome and deeply for as long as he wanted .