It's a long story but I had by now been the chastised slave to my former Mistress for over 6 months. Over that time I'd been conditioned to be more and more subservient. She seemed to take particular pleasure in humiliating me in front of others, especially her friends.
Most Friday nights she'd have a gathering at her house with 2 or 3 friends. I would serve them, naked except for my collar and tiny steel chastity cage. They all had great fun teasing meand examining my locked little peepee. As the evenings went on they'd take turns fucking my ass with strapon cocks and dildos, milking the cum from my swollen balls. I'd thank them by bringing each of them to orgasm with my mouth.
One night, as she was fucking my ass in the bitch position on a table, one of the ladies suggested that it was time for me to take the real thing. A discussion ensued, one in which was had no say. It seemed that this lady had a friend, black with a huge cock, bigger than any of the strapons or dildos I'd taken, and that he loved fucking the manhood completely out of little white boys like me. As the discussion went on I was filled with a mixture of excitement and fear. My caged little peepee was leaking cum on my belly. It was agreed that she'd call him and a date would be set for my deflowering party.
A couple of days later I was informed that the party would be the coming Friday night. All week long I was on edge wondering about my fate.
Friday eventually came around. Mistress gave me a bottle of Nair and a razor that afternoon telling me to remove all of my body hair and shave perfectly smooth. Half an hour later I was done. Just before guests began arriving she sprayed my lightly with some flowery perfume and applied just a hint of makeup to my face. She then had me put on some 4 inch heels and a silver anklet and practice walking in them, which to both our surprise I took to quite well. I quickly learned that it was easier if I adopted a more femine gait.
I greeted each of the guests at the door, naked except for my collar, cage and heels. The guests were mostly female, a few with boys in tow. Once inside the boys had to undress, house rules. I was pleased to see that all seemed so excited about the evenings events. At about 9 Eric arrived.
Accompanying him were two white boys, completely feminized in makeup, hairstyle and slutty clothing. Once inside the two white boys also removed their clothing revealing the tiniest shrunken little dicklettes I'd ever seen in person. And both had the beginning of boobies growing, with puffy nipples. As they turned around I notices that both wore butt plugs. I wondered if that was to be my fate.
Eric is a monster of a man. Well over 6 foot tall probably 250 lbs, muscular with a huge bulge in his khakis. He was very pleasant as he introduced himself, reaching down to give my little peepee a squeezes with his huge hands. He gently patted my ass saying we'd get to know each other better.
This evening I didn't have to serve refreshments. The other boys there took care of that task. That freed me to spend more time with rhe guests, all who delighted in telling me how the looked forward to seeing my tight white ass fucked. Many examined my locked little peepee and had me bend over so they could get a before view of my ass. It was all so enjoyable for them and humiliating for them. Likewise many of the ladiea were feeling up Eric to see what he'd be working with.
About 11:00 pm Mistress announced that it was time for the main event. A padded table was brought out to the middle of the living room. I was told to lay on it on my back and my hands were secured at my side, a pillow under my head so I could see all that was gpoing on. Eric's boi's removed his clothing revealing a chiseled body and a cock like a log. Still not fully hard it was about a foot long and as thick as my arm. The audience gasped. Both sissy's dropped to their knees and began stroking, licking and sucking on that massive cock and set of balls. It was obvious to all that they worshiped it.
Soon it was rock hard and pointing forward. Eric pushed his sissy's away and moved around so everyone could see his huge black cock. I was trembling, mostly due to fear when one of the ladies called for a measurement for the record. Another pulled out a cloth measuring tape and stepped forward. She pronounced the results, 14 inches long and 9 inches around om the shaft. The swollen head was even larger. As the room erupted in gasps and cheers I was nearly overcome with trepidation. Mistress could tell and soothed me by whispering in my ear that Eric's little pussybois take that cock regularly. If they could handle it certainly I could.
Two ladies grabbed an ankle each lifting them into the air and exposing my butthole. Another started preparing me by lubing me up with a large quantity of lube. First one finger, soon two, three and four. She pronounced me ready and retook her position in the circle surrounding us.
Eric approached stroking his monster cock before him. My ass was lined up perfectly. He smiled and told me and everyone there that I would be experiencing bliss like never before and that I'd never be the same. I had no doubt. "Ready sissy?" he asked. I meekly nodded accepting the inevitable.
That huge cockhead felt hot as it rested at my entrance. I concentrated on my breathing as he gently pushed forward stretching my ass like never before. I screamed in pain until his big cockhead was fully inside and he stopped to allow me to adjust. I could barely hear the small talk about how much he enjoyed breaking in little white boys and turning them into faggots for black cock.
