Anklet Adventure Pt. 03

I hurried to see what was so urgent.

Flushed with embarrassment and humiliation, he said, "Dad, look at me! What the hell is that? My cock is trapped in it. How did that happen? What the fuck happened to me? And I had this in my ass!" he exclaimed as he held up the big butt plug he'd obviously cleaned off at the sink. "I worked it out of my ass, and fuck, does my ass hole hurt and burn! It dripped liquid, almost like I was pissing!"

"You don't remember anything about what happened last night?"

He thought for a few minutes. "No, well, not really. There're some surreal thoughts, fantasies like come true, but I'm not sure. And I'm so hung over. Oh shit, Dad, I hurt all over!"

"Just take it easy," I told him, "It will come back to you as the day goes on. In the meantime, it would be best for you to work that butt plug back into your ass. Our host probably put it there or at least approved of it, and I don't think you want to disappoint him by removing it without his permission. After its back in, come join us on the deck."

"I can't. My clothes are gone. And I can't be seen like this!" he said, motioning to his cock cage.

"Are you so preoccupied with your own humiliation to notice you're not alone? Look at me," I told him, pointing to my matching little pink cock cage. Son, this is a sex vacation. We're here to be used and abused. If you have no appetite for that, I understand, and you may return home," I told him, knowing he wasn't going anywhere after his submission last night. A few moments later he joined us on the deck, cock caged and ass plugged.

Mark must have noticed our entire family up and alive at the pool so came out to greet us, in the buff as normal. "There's my pussy's, all five of them!" he said. Knowing the kids would be severely hung over from their black-out drunk, he couldn't resist teasing them. "Do our heads hurt today, kids?" he chided. "Its okay, you'll live. I know your bottoms hurt too; right? You've all been fucked hard and you did really well. If you don't remember, trust me, you had a really good time. You can have the rest of the day off to recover. Tomorrow afternoon, I'll bring you all new clothes for another exciting evening. Enjoy your day," he said, and left.

By the following day, everyone had fully recovered. The kids were up early and asked Thomas for mixed drinks with breakfast. He brought them straight orange juice. "Master said you were to stay sober today. He said you needed to be numb and dumb for your first night out, but tonight he wants you to be fully aware," he told them.

At around noon, a young lady delivered clothing for the kids in individual gift boxes with their names on them. Carl was amused that his read, 'Carla'. The girls opened theirs to find the minimalist wardrobe; heels, short skirt and a T-top cut off just below the tits. "That's it?" Martha exclaimed.

"You don't know anyone here and will never see them again," Lynda told her. "Just wear it and have fun."

Carl opened his and was in total shock. "What the fuck!" he cried, seemingly ashamed to even show us what was in his package.

"Show us, Carl," Debbie told him.

"This is just wrong. Its got to be a mistake," he said as he lifted some of the items from the box. It contained the same items the girls received, but he also received sexy, female undergarments and a blonde wig.

"Hmmm," Lynda replied, "I think you need to talk with your Dad about that, Carla. I don't think it's a mistake."

"He made me dress like that too, son. Don't be embarrassed, just go with it. They are not interested in your straight side, they only want to use your feminine traits. Its all good. Let Debbie and Martha help you with it. It can be fun."

The girls were actually excited about dressing up their brother. They took him to their room and went to work on him. They bathed and shaved him, rubbed him down with lotion from head to toe, put him in stockings with a garter belt and pulled on the silky lace panties. Then came the matching bra and a little cut-off T-shirt and short skirt. They made up his face, just like my wife had done to me when we were on cruise. I knew that if I could 'pass' as I did, that Carla would have no difficulties at all. 'She' was much more feminine than I in every way.

It was nearly five o'clock when they finished primping and all three girls emerged from the room, ready for dinner and a night on the town. They all looked a bit slutty, like very young, high class, teen hookers. They were gorgeous! Carla had obviously been practicing in the heels and had it down pat. He already had the feminine mannerisms, by nature, so she now presented the complete, convincing package. She was incredibly hot!

Mark sent Thomas over with one drink for each of them just to calm their nerves and bolster their confidence. Then, at about six, he and two other escorts came for them. Lynda and I were surprised to see Jack, the guy with the massively thick cock from the cruise, kneel at Carla's feet and place one of those BBC and spade charmed anklets on her before helping her from the chair. Oh fuck, I thought, our boy was in for it tonight!

"I'll have the kids home by one, Mom and Dad," Mark jokingly told us. "Don't worry about them. I'll see to it that they are well taken care of. We're doing a repeat of last night, but this will be a night for them to remember," he said with a smile. "Some friends will be by for you to entertain this evening. Do have fun with them," he told us, then leaned over to me and whispered, "One of them is strictly a gay top, just for you, bitch."

They walked the girls out to the limo and left while Lynda and I ran inside to clean up for the evening's activities.

The remaining days of our family sex vacation continued much unchanged. Carla stayed in character until the day of our departure, and what little inhibitions they still had after the initial night of fucking were completely gone after the second adventure. After the fourth night of our adventure, we noticed our kids' anklets were augmented by a tattoo; a queen of spades for the girls and jack of spades for our son. Our perverted voyeurism progressed from watching them fuck in their rooms to joint fuck sessions at the pool. Carla and I both had the privilege of clean-up duties for both males and females; all of them. Oh, what a thrill it was to place my tongue into those almost brand-new little girl cunts full of cum and lick them clean. On the very last night of our trip, Mark allowed my son and I to remove out cages just long enough to do a sixty-nine suck off for everyone's amusement. It was our first, cock induced cum since we had been paced in chastity, and it was great!

On the flight home, all wondered which of the girls might be pregnant. Were we going to have another black baby or two in the family? Was 'Carla' going to be attracted to women again, or was he strictly a faggot bottom cock sucker? Were the girls going to entertain any of the white boys they used to date? Maybe they'd be lucky enough to find one who would love and support them, and help them find big black cocks to fuck, like I was destined to do for the rest of my life. What a wonderful, fucked up life has come from that stupid anklet!