Around my junior year, Candace and I began to discuss boyfriends and girlfriends and things that went along with that. We had been drinking at my dorm and it wasn't long until the topic of sex came up. Candace was a beautiful girl. She had cute face, long brown hair, full breasts, perky butt and a fit frame. Yet, I had never looked at her sexually, more as just a friend. She began to talk about things that she enjoyed in bed and her pet peeves. It was weird to talk about sex with her, mainly because it made me look at her in a different manner. It was like all of a sudden I had noticed her sexiness.
We ended up sleeping together that night, and it was one of the hottest nights of my life. For hours, we went at each other, experiencing orgasm after orgasm. The next morning, we awoke and realized that our relationship had changed. We couldn't just stay friends after the type of sex we just had, but we also weren't ready to start a relationship together.
For a while, we tried to be friends with benefits, and it actually worked out for a few months. It was in those months that I really developed sexually. Our level of communication was so high, that we could coach each other on what we enjoyed and how we could do better in the bedroom. It was the perfect system, with what seemed to be the perfect girl.
Candace met her future husband later that year. As soon as he asked her out, she cut our friends with benefits off. We tried to remain friends, but it was no longer feasible. I had grown to truly love Candace, but she had not returned the sentiment.
Candace was a lot of the reason why I had never gotten back into a serious relationship. I dated on and off since college, but nothing ever lasted more than a few months. I owed most of my sexual expertise to Candace, which helped secure this job. Ironically, if she had returned the feelings that I had for her, I never would have ended up with this job in the first place.
I sat with my head buried in my hands as I sat naked on my bed. I guess over time I had become arrogant enough to believe that this would never happen. The feelings of embarrassment that were running through my head could not be stopped. I lay in bed and tried to sleep, but sleep alluded me. All of the confidence I had carried with me into this job had been stripped away in a single encounter.
It had to have been 4 or 5 o'clock when I finally fell asleep. When I awoke it was already 1:00 pm. I put on some clothes and walked out of my bedroom, relieved to find that Kerry had left for the day. As I was finishing my brunch, I heard the door to the suite open and shut. Walking into the living room was a tall, well-built, light skinned black man.
"Oh, you must be Joe, right? I'm Jake and I really appreciate you covering for me last night."
I stood and shook the man's hand and we made our way back to the guest bedroom. We began to converse as I packed my belongings and he unpacked his.
"How'd everything go last night?" Jake asked.
"Ehh, not great," I lightly chuckled to mask my embarrassment.
"Ahh, well don't let that get you down. Kerry told me that I am one of only two men that have been able to satisfy her. She just has issues sexually and her personality makes it difficult for her to overcome those."
Jake began to change his clothes as I zipped up my suitcase.
"It was just tough," I said, "I have never really had any issues like that before. I thought things were going well, but she said that it just wasn't going to work out."
It was around this point that Jake changed out of his boxers and I immediately realized why Kerry had issues with me the night before. Out of his boxers flopped out one of the largest cocks I had ever seen. His flaccid dick hung longer and thicker than mine did erect. It was this reason that I referred to him in my head as Jake the Snake. I was thoroughly impressed, and began to feel better about what had transpired the night before. There was no way I would be able to provide someone a cock that big, but that wasn't my fault.
This was the first opportunity I had gotten the chance to meet another associate of The Agency. I found out that Jake had been with the agency for two years and had gotten involved with the company the same way I had.
"So are you one of Eliza's associates?" I asked.
"No, I work for Claire, but I have met Eliza before and she seems like a nice gal. It has to be tough for her to be out of the field now, though."
"Out of the field?"
"Oh yeah, did you not know that she used to be a field associate just like us?" Jake asked surprised, "She used to be the company's highest grossing associate. She had a lot of big jobs, but her biggest was that she was the go to gal for George Clooney. They had quite the relationship, being together on his movie sets for 7 or 8 years. Evidently, when he met Amal, his new wife, he quit employing Eliza. She had grown pretty attached to him, which is easy to understand considering how long they were together. The big bosses found out she wasn't taking it well and pulled her out of the field and into an agent role."
"I had never heard about that," I said as I tried to process his story.
"This work is difficult man. When you get a client that you spend a lot of time with, it is easy to grow an attachment to them. Kerry and I have a great relationship, but I have to constantly remind myself that this is just a job and not build too much of an emotional connection. It is an exercise in futility, though. You are bound to build connections at some point. Our bosses don't care as long as it doesn't affect your work or compromise the secrecy of The Agency."
This conversation made me feel better about the job. After my training day, Eliza had made a point of saying that this job was just sex and that we weren't supposed to develop feelings. It now made sense that she was trying to prevent me from making the same mistake she did. However, I knew that I couldn't do this job without developing any emotional feelings. In my first mission, I had developed a great relationship with Taylor Swift, which I knew couldn't have been avoided.
Jake and I talked for a few more minutes before I finally told him I needed to head to the airport. I gave him my phone number in case he ever needed to reach me, or just wanted to hang out if we were off at the same time. Jake seemed like a nice guy, and it was very important for me to get to talk with someone that was in this same crazy situation.
On the car ride back to the airport, I just stared out the window and tried to process everything that Jake and I had discussed. Eliza finally made sense. This job finally made sense. Jake had provided a level of clarity to everything that had been bogging my mind for the last 5 months. Surprisingly, this had been one of the best days in my job, and I didn't even have sex with anyone. Instead, I was provided with clarity that had been wrecking my mind. I felt like I could now move forward with confidence.