It was a week and a half in, and Katy had stopped by for sex nearly 40 times. My imagination of sexual positions was dwindling down and my enjoyment in our sessions was dwindling with it. I wouldn't have imagined that I would get bored having sex with someone as sexy as Katy Perry, but nevertheless it had happened.
It wasn't that I wasn't enjoying the act of sex with her, as much as it was missing the emotional connection. The only way that I can make it clear is to compare it to masturbation. When I masturbate, I enjoy the sexual release it provides me. Masturbation can actually be nice on occasion as sometimes all you want is the release. However, eventually you want something more. Sex is about a lot more than just getting that sexual release, it is about the emotional connection that you gain with a partner.
I know that it may sound strange coming from someone in my profession and with my history; but I was missing the connection with Katy, and it was preventing me from really enjoying our encounters.
It was approaching midnight when Katy stopped in for her final romp of the day. This particular day we had already had sex four times, this next encounter being number five. When Katy walked through the door, I attempted to seem excited. My sexual energy was running low and I knew that sex again tonight would be difficult.
The last ten days had provided me with plenty of time to plan out my encounters, so I already knew what I was going to do tonight and how I was going to do it. Katy stood in the living room, fresh from her concert, wearing a tight short baby blue dress. The dress hugged all of her curves and showed off just enough skin to be tasteful enough for kids, but sexy enough for adults.
I led Katy back to the bedroom and removed my clothes, as she did the same. My dick flopped out of my underwear, soft as could be. I concentrated on Katy's big breast and nice ass, hoping that it would provide me enough motivation to get hard. My cock began to stiffen and grow, but it was quite as hard as I was hoping it would be.
I pushed Katy back onto the edge of the bed. I began to rub the tip of my cock up and down Katy's slit, which got me hard enough to penetrate her. My plan was to plow her from the edge of the bed and then finish with a few shot of warm cum on her boobs.
The thrusting began and it was evident that Katy wasn't going to take long, based on her reaction. I was thankful because I didn't think I had enough sexual energy to stay hard for a long session. I concentrated on Katy's breasts as they jiggled from the smacking of my hips against hers.
We were only a few minutes in and Katy already came. I pulled out, sensing that I was close as well, and began to stroke myself to try and cum on her. The pleasurable pressure began to fill up my cock and I released into my orgasm. The sensation felt good as always, but I hadn't blown out long streams of cum like usual. Instead, my cum slowly oozed out of my tip, dropping down onto the lower part of Katy's belly.
I was disappointed in the result, but hoped to play it off like that was my intention. I fell back onto the bed as Katy got up to clean herself off. Exhaustion was setting in, as this was by far the most sex I had participated in during such a short stretch. Katy wiped off her belly with a towel and began to gather her clothes to get dressed.
"I really appreciate the way you have handled yourself so far," Katy said, which was the most she had spoken to me during my entire time with her, "You have done a great job being available and mixing things up. I especially like that you haven't been super talkative. Most of the guys The Agency sends are always trying to talk to me after sex."
"Well, I'm just doing as I was told," I responded, "I was told that you didn't like to talk, so I have tried to stay quiet. It is not that I haven't wanted to talk to you, just that I know that you didn't care to speak to me."
"I appreciate you being considerate of that. It is just my personal preference when it comes to sex and relationships."
Katy began to turn to leave the room. It was the first real conversation I had with Katy in ten days, and it left me with more questions than answers.
"Katy, wait!" I yelled from the bedroom as she was almost out of the bus.
I jogged to the living room where she stood near the door.
"I know you say that it is just your personal preference, but I am really curious as to why? I know you might not want to discuss it, especially with me, but I would be very interested to hear why, if you are open to it."
I stood and stared at Katy as she decided. Most men would have killed for an opportunity to do what I was getting to do with Katy, but for some reason the situation was bothering me. Even if it didn't change, I would like to hear why she was the way that she was.
"It would...I'm not sure if...Well...," Katy stumbled, as she appeared to still be unsure, "It is going to take me a while to get through this. Are you sure you really want to hear?"
"I want to hear it if you are willing to tell it."
Katy nodded her head and took a seat on the couch in the living room. I grabbed a robe off the bathroom door, to cover myself, and joined her on the couch.
"I'm only doing this because I am appreciative that you have followed my rules so well. This is the only time I plan on opening up, so make sure that you get whatever answers you are looking for."
"Okay, I understand. Well how about we start with why you like to change things up sexually so much and why you only like to have one orgasm per session?"
Katy leaned back into the couch as she got prepared to give her answer, "Wow! You start with one of the hard questions. Well, I think that it stems from the way that I was raised. When I was younger I grew up the daughter of a pastor. My parents were very conservative and very strict with us kids. I was told from a young age that I couldn't date until after high school and that sex was forbidden before marriage.
"Don't get me wrong, I love my parents and most of the lessons they taught me were great, but I didn't have the wisdom to follow it. I wanted to be a rebel and so I would sneak behind their back and have a boyfriend and fool around with him. However, I didn't lose my virginity until I was 20. I was very nervous about it because I had told my boyfriend at the time that I wasn't a virgin.
"That experience opened my eyes to how fun sex can be. I kind of went on to the wild side when I got to Los Angeles and wanted to try different things with different people. That has always been my sexual craving is to explore sex with different people and learn what seems good and what doesn't. In a way, it was me rebelling out from my parents and trying to find my own ideas about good and bad.
"I give you all that backstory to circle back to your question. The reason that I like to try different positions is because it is my way of exploring sexuality with different people. I keep a mental notebook of what I like and what I love. I only want to achieve one orgasm because it keeps all of my sexual encounters on a level playing field. One experience can't outdo another just because it provided four orgasms. It allows me to look at each experience at the same level."
The reasoning seemed a little strange to me, but it made more sense than having no reason at all. Katy was being very candid with me, which I appreciated, as I had a few more questions that had gone unanswered.
"Okay, well that helps me understand that part. My other question is why do you try to avoid talking and building an emotional connection with the sex? Is it just because you hired me and you don't want to establish an emotional connection with me, or do you do that in all of your relationships?" I asked.
Katy wasn't as quick with an answer to this question. It seemed as if she maybe hadn't contemplated this before, or was trying to find a way in which to craft her answer.
After a few moments of silence, she responded, "It isn't just you. This is something that has kind of progressed over time. Sex when I first started had passion to it, but as I began to experiment more and more I abandoned the emotional connection to try and find what I liked about the physical side of sex.
"I got married a few years back, and our sex life wasn't great. Some of this was his fault, but I blame myself and my lack of intimacy for most of the issues that arose. He ended up cheating on me and our marriage ended as quickly as it started.
"Ever since then, I have become even more closed off. The pain that I felt from that divorce still lingers inside me, and I am afraid that any intimacy that I try to allow myself to have will end in heartbreak. This is the reason that I don't like to have a lot of talking with sex. All I want is that physical release, because I know that I can satisfy myself and whoever I am with physically. The thing I fear is letting down my partner emotionally again, so if I keep that out of the relationship altogether than I have nothing to worry about."
How incredibly sad her story was. Closing yourself off from intimacy altogether just based on one bad experience.
"Katy," I said as I placed my hand on her thigh, "you shouldn't have to be afraid of letting someone connect with you emotionally. Take this however you like, but as someone who has sex for a living, I find making connections with people something that adds to the sexual experience. Having sex without a connection is like eating food without seasoning. Sure, the food can still taste good, but it would taste even better with some seasoning."
Katy sat and stared with a blank look on her face. I wasn't sure if she didn't understand, or just didn't care.
"How about this, you give me one night to try and do things my way. If you don't like it, I will never mention it again, but I would like to show you how much better sex can be if you play by my rules, instead of yours," I said.
Katy looked at me with some skepticism on her face, but ultimately obliged my request. I laid out some ground rules for the next day. She was to arrive at my bus at six the next evening (she had a day off from her show before they started the final few concerts of the tour) and was to not come looking for sex until that point. I informed her that we would be together the rest of the night, so she needed to make sure she made no other plans.
When Katy left my bus, it was already late. I deferred making my plans until the morning and went to try and recover from the strenuous day.
