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.
The pause offered me an opportunity to change things up, and I wasted no time in doing so. I rolled Amy off my body, so she was lying flat on her back. Her red hair lie sprawled out across the white comforter. I moved to the foot of the bed and slid off Amy skirt, which revealed a pair of white panties highlighted in lime green trim.
There was a small wet spot on Amy's underwear from where she had been grinding up against me. I brushed my hand across it, feeling the little bit of stickiness seeping through. Her panties came off with ease and I got my first glimpse of Amy's pussy, which was cleanly shaven.
As I stared at Amy lying nearly nude on the bed, I noticed how much she looked like Samantha. Granted Samantha was younger, had a bigger butt and boobs and was taller; but lying on the bed there was a definite resemblance. The red hair was nearly the same shade and their skin tones were identical. There was also something about their face that was similar that I couldn't quite pinpoint. Regardless, this revelation was a major turn on for me, as I had been missing Samantha over the last few days.
I slipped off my shorts and unleashed my dripping wet dick. The temptation for me to take that opportunity to mount her and thrust away was strong, but I knew that wasn't what Amy was looking for. I crawled part of the way up the bed and adjusted Amy's legs so that my mouth could find its way to her smooth pussy.
Going down on a woman was one of my strong suits. This skill had been acquired over time, but some of the skill was tied to my ability to read a woman. Not every woman likes to be gone down on the same way. For some, they like hard and fast passes of the tongue, while others prefer it light and slow. Some women like you to focus solely on their clit, while others like for you to explore their entire pussy with your tongue and lips. The options are endless, so it takes some trial and error to find what will set the woman off. I had a very good ability to be able to adjust and find out quickly what a woman liked, and make it happen.
I knew that Amy would like it light and slow, based off the way the rest of our encounter had gone. The tip of my tongue slowly passed up and down Amy's slit. I continued to pass it up and down her slit, sliding my tongue deeper with each pass. Amy closed her eyes and began to moan as I worked. My tongue focused on Amy's clit, slowly increasing my speed and force. Amy's eyes were closed, as she lie on the bed jolting as the pleasure shot up her body.
"Oh...my...YES!" Amy screamed, grabbing the back of my head and forcing it against her hips as she enjoyed the pleasures of her orgasm.
Amy finally released her grip from the back of my head and I pulled myself away from her pussy. I maneuvered myself forward, as Amy was panting trying to catch her breath. The tip of my cock was already soaked in precum and I slipped myself inside her. I slipped inside with ease, but Amy's pussy was a little tighter than I had expected.
As we lie in the missionary position, I placed my hand behind Amy's head allowing me to pull her body closer to mine as I thrust. My thrusts started off very slow, but I was not timid.
"One, two, three, thrust," I counted off in my head as we began. My hips clapped against her elevated thighs with my powerful thrust forward.
Amy's face was frozen, somewhere between a smile and a moan. I slowly sped up my pace, keeping my pauses between thrusts to a minimum. As I began to rub her breast with my hand, her face finally became unfrozen, as she began to let out precious moans.
The bed began to creak and smack against the wall. I was doing my best to not sacrifice motion for speed, but it was difficult with how hard I was going. Amy's precious moans turned to screams as she got close to another orgasm.
Amy reached up and dug her finger nails into my back as the orgasm took over her body. I continued to thrust vigorously trying to push myself to cum. As Amy's orgasm came toward an end, I fired my load inside her. I froze as I could feel my cock flexing involuntarily as it spewed out ropes of my cum.
I could feel the last bit of cum slip out of the tip of my cock, and I slipped out of Amy and laid beside her on the bed. Amy and I both lie breathing heavily. After a minute, Amy caught enough of her breath to speak.
