My name is Ryan Sterling and I own a resort in the Florida Keys. Daniel, who is eighteen, and I live on the resort in a penthouse overlooking the water. He is going off to college after the summer is over. Daniel is not my son but his father died when he was young, and I have known him for years and taught him everything he knows about everything.

I have been teaching him some of the basics about how to bed a woman properly and he essentially asked me something to the effect of; 'Will you and/or can you demonstrate some of this to me?'. I told him that I could not at the moment but when I did I would let him know.

I found who I wanted to teach him with, her name was Stella and she was thirty two and had eyes that pierced right into your gut. She had been staying at the resort for a week and so I had introduced myself to her as the owner, honestly wanting not much more than to get inside her. She seemed quite open in more way than one and long story short, she wound up getting herself another week free at the resort on me after we had kinky sex for nearly an entire day on Tuesday.

It was now Friday and I was eager to teach Danny some new tricks. I went down a couple floors to the room that I had Stella put up in and asked her how she was doing. She responded that she was overwhelmed with the view from her room and the treatment she had been getting from the staff. I asked her quite bluntly if she would be willing to be my womannequin for Daniel's lesson. She responded that she would want to see a picture of him first so that she would know what she was getting herself into. I showed her his social media profile and she was elated to see that he was simply an eighteen year old version of me with slightly tighter abs.

She was all too happy to accept her new opportunity and asked what time she should swing by the roof. I told her to come over for dinner around eleven and texted Daniel to be home by then because I had a surprise from him.

I told Stella I would see her later and she gave a cute air kiss goodbye.

The kid walked through the door at ten, a bit drunk but nothing too out of the ordinary. He bluntly asked as he walked in where his surprise was. I told him it would be coming soon and that he would have to be a bit patient. He obliged and started listening to some music on the couch with his headphones in. I ordered room service dinner and Stella walked in about five minutes after the food got up to our apartment. The sun was setting and you could see the scenic vanilla sky against the ocean through the floor to ceiling windows.

I explained to Daniel that Stella and I had been having sex and that she would be the woman who I demonstrated some technique on for him. He was a bit shocked at first that I had actually gone through and fulfilled his half-hearted request, but after the initial shock, his face turned into a cheek to cheek grin. He was like a kid on line in a candy store, just waiting to taste what was under the wrapper.

I told Stella that she could start disrobing if she felt comfortable to which she immediately stripped stark naked. I told Daniel that I'd be getting hands-on and that he could take off his clothes too if he wanted some practical lessons.

He nearly jumped out of his clothes and was naked in a matter of moments. His body reminded me of how I looked when I was younger, now thirty-eight, I saw his strong younger features and felt proud of how he had developed.

I took off my clothes as well, and ripped off a condom pack as I put a raincoat on my eight inch dick. It was always funny how small condoms felt on me and how nearly funny it was to see my dick in a plastic wrapper. I immediately grabbed Stella and held her mid-air as I shoved my dick into her pussy slowly starting with the head. However, gravity did its job and she was soon fully impaled by my dick.

I sat down on the ground and she continued to remain in place, having sex with me cowgirl style and not even caring that my horny little friend was jerking off next to us. I told him to watch how I was able to fuck her slowly and not rush, letting the tension and excitement build up in her. Stella started panting, and, like clockwork, needed a faster tempo than I was initially giving. The result was her bucking her hips as hard as she could on my dick, grabbing it with her kegels as she moved up and releasing as she sat back down.

After a minute, I was ready to cum and I let Stella suck me to completion. Dan was staring at Stella and I quite possibly in wonder of the fact that I still had sex, and was still good as ever at it. Stella stood up and motioned Danny to come over saying, "It's your turn now, kid."

Dan got up and jokingly told me that my old fashioned ways were not enough for a hot younger woman like Stella. He grabbed a condom from the box and put one on his slightly smaller seven incher that was only slightly less girthy than mine. He began to pound Stella like there was no tomorrow, moving his log in and out like a little rabbit. I told him to slow it down and after some reluctant (and pleasurable) moaning and groaning he finally acquiesced.

Their hips began to move in slower rhythm as Danny stopped trying to be the fastest person in the room. I told him to sit down and have Stella do the work for a little. I watched his face twist and his toes curl as he experienced pleasure like he had never bothered to take the time to experience before. He was soon in the throes of orgasm and he came inside the condom inside Stella, completely out of control of his body. Stella also began to cum and they finished in a hot sticky mess o top of each other.

They dismounted and she said, "I think you learned a lesson today. Timing is everything and what you think is pleasurable might not be as much as you can be getting."

"You might be right," Dan said, "hopefully this won't be the last lesson."

"It won't," she replied, with a cheerful grin, "so long as Ryan is okay with this setup."

I said she could stay at the resort as long as she wanted and could even go on the payroll eventually as an instructor for the summer if she wanted. She said that would be lovely and that she could not imagine a more fun summer job. We all fell asleep naked in my bed, giggling and warm, thinking about our next lesson.