CHAPTER 19

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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."

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