Chapter 36

Six beautiful women in an iconic Sports Illustrated swimsuit pose, standing on the edge of the infinity pool with the Caribbean waters in the background. Except no swimsuits. They were bent over, displaying their backsides with faces hidden. And anal gems sparkling.

The day we arrived in Antigua, I opened the BDSM crate Maggie had bought. Inside, I’d crammed in six anal training kits among the cuffs, crops, light whips, and vibes. I observed carefully for their reactions. Their excitement was universal. But I saw concern on Lisa’s face for just a moment. I knew Doris Alex had enjoyed anal sex, but certainly not since her new teenage body. Teresa had as well, I assumed, but long ago. I’m pretty sure Lisa had, but we had not discussed it. With the other three, they were anal virgins.

Doris Alex and Teresa deputized themselves as my anal officers. They would tell me when my Siblings were ready. I needed to use their expertise versus just jumping in, there being a legitimate safety concern. After all, I had no experience.

I gave them the kits and let them go at it. That first day they called me out to the pool to take a photo. All six of them naked, with jeweled anal plugs in, bent over with their faces hidden.

Such a cool photo; I had to share it. Now, who could I send it to? Only two people. Penny was first. And by her enthusiastic reaction, I knew we would not be a onetime thing. She was already talking about the plane ride home. “I miss you, Brother, and can’t wait for my time with you in another week.”

I sent the photo to Larry. He was pissed that I had not invited him along. Next time, I told him. He quickly picked out Maggie, Molly and Doris Alex. We talked about Teresa, Lisa, and Hanna. He and Sarah, his girlfriend, were still a thing. Maybe I’d have a matchmaking side career.

I also told Larry about the estate I’d purchased and suggested he apply to Oregon and come out after his senior year in high school. When he groused about not being able to afford out-of-state tuition, I offered to cover him completely.

“Dude, I am destined to be a Hawkeye, not a Duck.”

He’d never be a Brother, maybe not a Sibling, but he was my best friend. I’d have to fly him out soon so he’d know what he might miss.

So it was a week later after that first day; I found myself looking at the photo again on my iPhone. Nate had just called on my encrypted app asking about his daughter, Hanna; then the conversation shifted to Teresa.

Teresa was not the emotional mess I had expected. Her body was changing, becoming visibly younger. Doris Alex was a great help, having been through it. Although Teresa felt disappointed about potentially losing her real estate business, she also recognized the positive effects of becoming younger. Fortunately, Doris Alex had packed a makeup kit to create an older Teresa when returning through US customs.

I ended the call with Nate from my bedroom. I had the best bedroom as it was closest to the pool. But every bedroom was massive and had its own enormous bathroom and an outdoor shower. Mine was the nexus of sexual activity as my siblings shared the other three bedrooms. I walked to dinner alone as my six Siblings awaited me, chatting pleasantly among themselves.

Our little island was a group of private villas and a small luxury hotel that had a resort attached. Our temporary home was by far the largest on the island and completely private, including a private beach. Massive greenery of bushes and trees made us believe we were the only ones in existence. So, the best of all worlds. Complete privacy, yet access to a private resort.

We had eaten at each restaurant and at a beach barbecue on our island. It was minutes offshore from the island of Antigua, but we had not ventured there yet, except for departing our jet. Tonight we stayed ‘home’ and ate on the stunning veranda. Our temporary home came with a full-time chef, and why not take advantage of his skills while enjoying the magnificent sunset view over the Caribbean sea.

The women wore casual cover-ups over bikinis, and I wore my favorite black Tom Petty shirt and black shorts. I should have been in white? “Oh, wait!” I said, “I’ll be right back.”

I strolled back in with my authentic, hand-woven Panama hat with a wide black ribbon. Behind my back, I whipped out six women’s versions. Molly saw me first and squealed, “Party hats!”

I handed them out and grinned in satisfaction. “Now this is everything I imagined: sexy women, a veranda, food, drinks, and Panama hats!”

Amazing how something simple can raise the excitement level. I took my iPhone and linked to the stereo system on the veranda. Bob Dylan’s Black Diamond Bay cranked up loud. They loved the song, even though it was Dylan. Soon we were battling back and forth with each of our favorite songs blaring. The party was on!

Lobster, red tuna, conch fritters, salad, and a fresh ocean breeze. My focus kept shifting from food, the six women, and the killer view. Gentle sea breeze, lightly perfumed by the tropical flowers in the landscaping. How could life be any better?

Tonight we shifted seats as we sampled the food and an array of local drinks. The Jumby Bay Rum Punch was my favorite. Gin and grapefruit juice was nice too. My Siblings loved the mango daiquiris, various other fresh fruit drinks, and, of course, more champagne. We were all pleasantly buzzed.

While sitting between Molly and Hanna, they giggled about our pre-dawn rendezvous for sex on the beach. I brought vibes from the BDSM crate and a couple of large beach blankets. They brought ... their naked selves. After sex with me, while running back to their bedroom, they crashed directly into the gardener who was beginning his day working on the hedges. Poor guy got the most pleasant shock of his life as two beautiful naked women knocked him down and landed on him. Then fawned over him, making sure he was okay. They quickly surmised by the cock under his white shorts, he was just fine.

Sitting next to Lisa later, she whispered to me, “I’m ready, Brother.”

Teresa was alongside and nodded, “She is Z, tonight, please.”

I beamed. “Both of you come to my bedroom about midnight. I’m going to have a ... meeting with Maggie and Doris Alex first.”

Three threesomes in one day! And a full day of sailing. Why don’t we just stay here permanently?

After dinner, I took Maggie and Doris Alex by the hand, and we drifted off to the pool. We really were going to have a meeting. After they shed their cover-ups, bikinis, and Panama hats, I threw off my clothes, and we hit the water. Maggie and Doris Alex dunked themselves fully; dirty blonde and red hair just darkened in the low light.

“Wouldn’t it be nice to come here anytime we wanted?” asked Doris Alex.

“It is truly amazing. We still have another week.” I said.

“But wouldn’t it be perfect to come back any time we wanted?” asked Maggie.

“Absolutely, but I am sure this place is in high demand.”

“Unless...?” Maggie started.

“Wait, you are talking about buying this property? I actually thought about it for a minute and checked; it is not for sale.” I said.

Maggie gave me her famous smile. “About that. Doris Alex and I checked more deeply than you did. We can buy it.”