My name is Kai.
I was twenty-one, tanned, and dead broke when the Harrington women hired me to “teach surfing.”
Turns out the only thing they wanted to ride was me.
100 % first-person male diary • one summer as live-in boy-toy for an entire billionaire dynasty of women • Martha’s Vineyard • beaches, boats, barns, and zero escape • 18+
I stepped off the ferry with a duffel bag and a six-pack stomach. A black Range Rover was waiting. Inside were three generations of Harrington women staring at me like I was lunch. Eleanor (the 68-year-old matriarch, still stunning) reached over from the driver’s seat, squeezed my cock through my board shorts, and said, “Welcome to the family, darling.” I was hard before we hit the private driveway.
First night Eleanor took me to her bedroom alone. Silk sheets, ocean view, bottle of 1982 Margaux. She made me strip, poured wine over my chest, and licked it off while telling me exactly how she built her fortune. Then she rode me so slowly I begged. When I finally came inside her she kissed my forehead and whispered, “Good boy. Tomorrow you meet my daughters.” I slept with her hand around my throat and her pussy still pulsing around me.
Charlotte (48, Wall Street shark) and Victoria (45, gallery owner) share a wing of the house. They made me fuck them together on the rooftop deck at sunrise. Charlotte in my lap facing me, Victoria behind me with a strap-on, both of them kissing over my shoulder while the gulls screamed. I came so hard I saw white and they just laughed and swapped positions.
There were six cousins, ages 28 to 38, all bored and beautiful. They turned the pool house into a rotation schedule taped to the fridge. My name in dry-erase marker next to time slots. I lived in board shorts that never stayed on longer than thirty seconds. Some days I didn’t even make it out of the outdoor shower before someone dragged me onto a lounge chair.
150-foot yacht, fireworks over the harbor, thirty Harrington women and me. They tied me spread-eagle to the bow rail naked while the sky exploded red and blue. Every time a firework went off someone new climbed on. By the finale I was painted head-to-toe in cum and champagne and the entire family was singing the national anthem off-key while riding my face in rhythm.
Old horse barn converted to playroom: swings, benches, mirrors on every wall. One night they blindfolded me, led me in, and spent six straight hours edging me. Hands, mouths, toys, ice, hot wax. I cried, I begged, I promised them anything. They finally let me come at dawn and I shot so far it hit the rafters. Eleanor wiped my tears and said, “Welcome to the permanent staff.”
Labor Day weekend. They threw a “goodbye” party that lasted four days. Every woman who’d ever touched me came back. I was passed around like a joint at a music festival. I stopped counting after fifty. On the final night they carried me to the beach, laid me in the sand, and took turns one last time while the tide came in and washed us clean.
Summer was supposed to end. My ferry ticket expired. Instead Eleanor tore it up, handed me a black card with my name on it, and said, “You’re not seasonal, darling. You’re family now.”
I’m twenty-three this year. Still sleep in a different bed every night. Still wake up with salt on my skin and someone’s mouth on my cock. Still get hard every time I smell sunscreen and money.
Best summer job I never quit.