It is a pleasure to be fabulously wealthy. It gives a teenaged boy lots of opportunities that would never be available to a middle-class teen. One of those things is learning to sail and drive large motor yachts. I showed an early interest and my oil baron father provided me with the best training in both classes of vessels.
My story starts one day when I was inspecting our sixty-foot yacht. I was a fanatic about order and safety. After checking all the life vests, the zodiac, and emergency communication gear. I got a phone call from my mother that she and grandma wanted to go out for a day in the sun. She informed me that I was to captain the vessel and they would be there in ten minutes expecting to leave.
The boat was ready, so this didn't bother me, but I had a date scheduled with this young model for some fun and sex during the afternoon, but my sex life meant little to mother and grandma. I couldn't say no, so I started up the engines and waited for their arrival.
Their limousine pulled up to the gangway and I dashed down to meet them. As I opened the door I was surprised to see a man with them. My mother introduced him as Paco. Paco was around Mom's age, forty-one, but seemed to be with grandma, as she held onto him as she went up the gangway. Grandma was sixty-three and had a great figure, the best that money and plastic surgery could provide. Mom was drop dead gorgeous and with little work to keep her there.
Mother stopped by me before boarding. "Louis, we're going below to have a drink. Call us when we're out to sea."
I gave her a quick salute. "I will do that." She went aboard wearing a cover up and without the bag she had left at my feet on the dock. I took the bag on board then cleared the lines and backed the boat out into the channel.
I kept a slow pace until we cleared the outer marker buoys and then turned on the speed. When I got three miles out I keyed the intercom and let Mom know we were out to sea.
It was a smooth sea with a gentle wind. I could see other boats, but none too close to us. I kept a heading out to sea.
Mom was the first up, and my mouth dropped open at the sight of my mother wearing a string bikini bottom and no top. Her big breasts jiggled as she climbed up on deck. I was glad I was wearing sunglasses as Mom might not have liked the going over I gave her as she smiled at me.
Next up was Grandma Claire. She wore the same as mother. Grandma Claire's tits didn't jiggle like Mom's. Grandma's were fake, but great fakes, in that they looked natural, they just didn't move when she did. She walked over to Mom and whispered in her ear. Mom looked over at me and shook her head as if to tell me to stop gawking at them.
Next up was Paco wearing a Speedo thong. Not many men can pull off wearing a tight thong bathing suit, but Paco could. He was built. His muscles were well defined, but most defined was the large cock stuffed into the suit. If he got a little excited, something was going to leak out. He moved up next to Grandma Claire. Neither Mom nor Grandma Claire worried about what would be said after this voyage. It was an unwritten rule that what happens on the boat stays on the boat. If Mom and Grandma were going to be up to something with their Latin companion she knew my lips would be sealed.
I set the autopilot and climbed down to the foredeck. "Drinks, anyone?" I asked. Being captain also meant that I was bartender.
All three wanted Margueritas. I opened the bar as Mom spread out a thin pad big enough for the three of them to lie on over the deck. Mom laid down on one side and Grandma Clair and Paco laid down on the other. Paco produced sun tan oil and began to oil up grandma's well-tanned back.
I served up the drinks. Mom sipped hers. "Nice job, Son. Do you think we're far enough out to strip down?"
I stood up and looked around and saw no one within three miles. "You should be good, Mom."
She smiled and untied her bottoms and tossed them aside as did grandma and Paco. I'd seen mom and grandma naked before on trips, but Paco had a huge cock. It flopped over his thigh and he looked at me as if to say, top this.
So I did. I stripped off my clothes and stood naked by the passengers. My dick was legendary. Mom loved to take newbies on trips and see their faces when I stripped naked with them. I'd had women choke on drinks when my cock came into view. Mom called it 'Moby Dick.' Paco had a surprised look on his face, then he licked his lips. I smiled at him and licked mine back at him. I was one of those guys who, when he puts his hand down a pair of pants is happy with whatever he finds.
I went up to sit on the flying bridge and keep an eye out for other boats and watch to see if there was any action below.
It didn't take long before Paco's application of sun tan oil onto Grandma Claire's body turned into foreplay. His fingers were rubbing Grandma's pussy and she was loving it.
Mom watched and rubbed oil on her tits. Grandma's face was a mask of lust as her Latin lover worked her pussy lips and clit. He was obviously a professional, he seemed in no hurry to get Grandma off, he was booked, I was sure, for the entire day.
Mom raised her glass and I climbed down to make her another drink. When I delivered it to her, Paco had Grandma on the edge. I stood by Mom and watched him bring Grandma to an orgasm.
Mom looked up at me. "Why don't you get back up to your perch? We don't want to hit anyone."
I knew I was being dismissed so I resumed my seat up on the flying bridge. As I sat down I saw Mom beckoning Paco to her. Mom laid on her back and Paco applied the oil to her body. While I watched him turning her on, I was happy that Mom and Dad had an open relationship. This relieved me from informing on her when she had some extramarital cock.
Mom's hand took hold of Paco's cock and stroked it as he rubbed oil into her tanned skin. Grandma rolled over and watched her daughter as she jacked on Paco's cock.
I opened a safe on the bridge and took out a high-end video camera. I focused it on Mom's hand and hit record. Mom loved to make videos of her sexual encounters for viewing later.
I watched her though the view finder as her lips surrounded the large circumcised hear of Paco's dick. I kept the focus close because Mom loved videos of her giving head to big dicks.
I was so focused on filming Mom that I didn't notice Grandma climbing up until her lips went around the head of my cock and her cheeks hollowed. I grinned down at her and put my left hand on her head to push it down over my dick.
It might surprise you that I didn't seem surprised that Grandma Claire was sucking my dick. Ten years ago, when I was fifteen, Grandma Claire took my virginity on a boat trip with my parents. She had caught me below when everyone else was topside and introduced me to the pleasures of fucking.
Mom was taking Paco's cock deep and was drooling down the shaft and fondling his balls. I was getting it all even with the distraction of Grandma on my dick.
Mom shoved Paco down on the deck and mounted his cock. I got a great shot of his brown dick splitting Mom's pussy lips and entering her.
Grandma said, "Hand me the camera." I passed it to her and she leaned over the rail and filmed her daughter fucking their gigolo. She wiggled her ass at me, and I knew what she wanted.
I got on my knees and spread her ass cheeks and stuck my tongue into her tight little brown pucker. Pressing my tongue into Grandma's asshole I heard her moan trying to keep quiet so she could capture my mother's loud moans and dirty talk.
With my face in Grandma's ass I couldn't see mother anymore, but I could hear her grunting. "Fuck my cunt, you stud. Give me that big fucking dick."
Grandma wiggled her ass again and I again knew what she wanted. I stood up and fit my hard cock to her cunt and pushed it inside my grandmother. I'd fucked grandma many times over the last ten years, but I loved every time I had her. I had certainly fucked her more times than any other woman I'd had.
Grandma filmed Mom's climax and Paco pulling out of her and shooting his load on her face and into her mouth. Mom's face looked like a badly iced cake when Grandma put down the camera and turned back to look at me.
"Fuck me, Louis. Give your grandmother that big dick of yours. Put your thumb up my ass and make me cum."
.... There is more of this story ...