My night with Ariel had been fun, but tiring. The next morning, I woke up exhausted, struggling to find energy. Today was an incredibly important day, as I had three prospective clients waiting to try me out.
I made a large pot of strong coffee and began to down cups of it to try and provide myself with the energy that would be necessary to make it through this day. I sat and pondered what the day had in store for me.
Amy Adams was first on my schedule and was a bit of a concern for me. The oldest person I had ever been with was my failed encounter with Kerry Washington, and Amy was a few years older. This may not have anything to do with age, but I still was concerned about the age gap. I was very familiar with Amy as an actress, and was definitely attracted to her; but I knew that the assignment could be a difficult start to the day.
Selena Gomez was my second assignment, which was the one I was most excited and nervous about. Taylor Swift had recommended me to Selena, so I knew I needed a good performance. Taylor had also alluded to a possible threesome in the future if the encounter went well, so I had an added pressure to succeed.
Ariana Grande was the third and final assignment, but was one I felt strangely confident about. In all of my years of having sex, I seemed to perform better with smaller girls. I was athletically built, but not necessarily muscular. Smaller girls had always been easier for me to carry around and manipulate in the bedroom, so I had a lot more options of things to do. If I could make it to Ariana's appointment with enough energy, I knew I could put in a good night's work with her.
I heard a knock at the door and went to answer it. Amy stood waiting, wearing large sunglasses, a yellow skirt and a tight black shirt. I welcomed Amy and showed her inside.
"Mmm, is that coffee I smell?" Amy said as she sniffed the air.
"It is. Would you care for a cup?"
"I would love that," Amy replied as she took a seat on the chair in the living room.
"Cream or sugar?"
"Just cream, please."
I poured Amy a cup of coffee and brought it to her before taking a seat on the couch, sipping the last little bit in my mug.
"How has your week been so far?" Amy asked, taking a few small sips.
"Very tiring, but pretty good. It is difficult to have a bad time in a beautiful place like this. How about you?"
"Well, the first day I got to explore the resort some, but yesterday I was busier. I scheduled some time with a guy named Michael, and that didn't go too well."
"Really built, white guy?"
"Yeah, you know him?"
I laughed, "Yeah, I've met him before."
"I'm sure he is great for some people, but I am looking for something a little tenderer. I was told by one of the agents that you might be that guy."
I got a kick out of the thought that I may be better than Michael, especially considering how cocky he had been all last week. It seemed like I probably was a better fit for Amy, which put me at ease about some of the concerns I had coming into our meeting.
"Hopefully I will be just what you are looking for," I responded with a smile.
Amy and I chitchatted while she finished up her cup of coffee. We then made our way to the bedroom. I still wasn't sure what to expect from Amy, outside of that she preferred tender loving, at least in comparison to what Michael gave her yesterday.
Amy grabbed me when we entered the bedroom and began to kiss me. Her kisses weren't aggressive, but soft with a very loving feel to them. We made our way to the bed and I sat down on the edge and allowed Amy to sit on my lap.
Amy's kisses were slow and gentle. It was nice to be kissing without any rush to it. I explored her body with my hands as we kissed. Amy pulled off my shirt, but never sped up her pace. The slow and gentle nature of her kisses began to put me into a trance. I was relaxed, almost too much so. I needed something to bring the life back into me, so I pulled off Amy's tight black shirt.
Amy had a very tight, perky body for being over 40 years old. I had been with women nearly half her age, which she put to shame. With the black top removed, I was able to see her lime green bra, which appeared to be a pushup as her breasts seemed far larger than mentioned in her bio.
Leaning up against my body, Amy pushed me back flat onto the bed as we continued to kiss. I could feel Amy's hands move down toward my shorts, lightly caressing my hardened cock over the fabric. She then dropped her hips down toward mine and began to grind her hips against my dick, never stopping her kisses.
Again, Amy's movements were slow and gentle grinding against me. I could tell that when Amy said she was looking for something tender, she really meant it. I enjoyed sensual sex, but hadn't really had any all week. My previous clients had all been looking for some intense loving, but I needed to dial it back and be delicate this time around.
I reached down toward Amy's grinding hips and slid my hand up her yellow skirt. I placed both hands on her butt and began to slowly massage each cheek with my hands as she rocked her body. For the first time, Amy paused our kiss as she leaned away to let out a little moan.