Rachael Ch. 06: Jocks

Chapter 6

Jocks

Madame Silver described the terms of employment and we went over the agreement that she wanted me to sign. It seemed clear and mostly about indemnifying her should I screw up. The rate was fair; I got 30% plus room and board. I could get out of my apartment and save a bunch of money. She didn't have any problem with me staying in school. She even encouraged it and said she would make accommodations with my schedule. This seemed all too perfect for me, so I pressed her about wanting to become a lady, a real lady. She said she would help me with the training and the medical side of things, I couldn't ask for more.

I moved into Madame Silver's bordello the following week and took up my place in the selection room. The first night I had two customers and they both seemed to enjoy my special equipment. Seems one of them asked especially for a TS and management did the picking. He had been with Madame before and hesitated at first but warmed up when he discovered my appearance and youth. We had a good time and he promised to come back and see me. He also left me a nice tip for my cash collection. Life was good at Madame Silver's house of respect.

I soon settled into a routine, classes during the mornings and sex in the evenings. What a wonderful world. No games, no stress, just study and sex. Once a week Madame would call me to her quarters and we would talk about my feminine issues. We worked on wardrobe, makeup, hair, posture, walking, sitting, and presenting myself to the male population as a lady. I wanted nothing to do with lowbrow looks or the tramp appearance.

I started dressing up for classes, which at any University will get you plenty of notice. I didn't have much competition in the looks department in class, the guys all tended to chat me up, but I managed to keep them at arm's length and made no dates.

Then I met Joe. He swept me off my feet. Literally picked me up and swung me around. Shocked and taken aback I didn't know what to do so I put up my usual defenses and fended him off. Not to be put off, he was aggressive but polite, insistent but nice, very good looking and sexy as hell. He took me to lunch after class that spring, and we became an item almost instantly

Joe is a jock, big and strong, he played baseball and stared for the school team. A rock-solid short stop with a 400 plus batting average, stars in his eyes for the majors and a very strong work ethic. I went to practices and some games. I told Madame about him in one of our "lady" sessions and although not pleased, she tolerated it.

I knew early on that I had to keep sex out of our relationship. I kissed him and even jerked him off one time to keep him placated. I really liked being with him and I didn't want to scare him off. I don't think he would have approved of my living arrangements or my employment.

Just before school let out for the Summer, I decided the time had come for him to learn a few things about me. I knew it was going to be hard and I might lose him, but it needed to be done. We ate an early dinner and I told him we needed to talk about the upcoming summer. He planned to go home for a while and I, of course, intended to stay in town.

I started off by telling him I had some secrets that he may or may not approve of. That's just the way things were. These are the things that I am and not much is going to change even if we develop a long-term relationship.

"First off, I am a transgender person. That means I am not all woman, parts of me are male." I paused and let him soak that in, drank some wine and watched him.

He looked at me and said, "You have a cock?"

I nodded and didn't say anything.

"Is that why we haven't had sex?"

I nodded again without speaking.

"Wow, this is something I never expected," he said.

I looked him in the eyes, and I could see tears forming and I knew this was going to be bad.

"I am in a long-term program to fully transition to a woman over the next several years. It doesn't happen overnight. I have been living as a woman for four years now and I work every day at making the final transition. Having said that, I am several years away from my goal, but I have no intention of wavering from the course."

"Does this mean I am gay?" he asked.

"I don't think so," I blurted. "You didn't even know."

I could see that I damaged his ego and I was not sure he could handle the rest of this I backed off and let him think. His face turned into a mass of indecision and I shortly could see that this wasn't going to end well. For all the open mindedness of the modern world there are just some things that are too different to accept. For Joe, that included having a gay lover.

We parted company that night, no kiss, no promise, no "see you tomorrow", no nothing, just parting.

Sometimes you get the bear and sometimes the bear gets you. My conscious was clear, I did my duty and I didn't have to tell him about Madame Silver.

That summer after my sophomore year at University turned out to be short and very sweet. Business at the bordello maintained itself as it boiled down to the regulars who were not students. The students made for volume during the class year, but the townspeople made for quality all the time. I learned early on to accommodate my regulars and make sure they didn't suffer in the busy season. Most of them understood that this is how I make my living and gave me some respite.

I had saved a lot of money over the summer and salted it away in my surgical account. The sooner I had the cash the sooner I could fulfill my constant desire to be a woman, completely. I couldn't wait to have a pussy and be able to entertain a lover as a real woman. I feared it would be unfulfilling but pressed on never the less.

School started in the fall and I returned to class while still working and living at Madame Silver's wonderful house. As classes ramped up my thoughts returned to Joe. Not having seen him I wondered if he enjoyed a good summer. On the off chance of seeing him from afar, I went to a baseball practice in the second week of Fall Training. I sat under the bleachers because I didn't want him to see me, modesty, I guess. I really liked the guy. I just couldn't cheat him. He was playing shortstop and getting a workout of grounders from the coach conducting infield practice. They must have run a dozen double plays back to back with hard shots to the shortstop and the second baseman, a nice-looking guy I had not met.

I enjoyed their workout and cast my eye around the stadium for others I might recognize. Low and behold I spotted Jenny, one of the girls from Madam Silver's hanging over the fence shouting encouragement to the infielders. I watched her for a while. There were quite a few spectators so I could move around and check her out from different vantage points. She seemed to be having a good time. When practice ended, I watched Joe go over to her at the fence and she leaned in and they kissed each other with something other than a "hi how are you" kiss. Very interesting, I thought.

It was a work night and I went home and prepared myself for the evening's festivities. Madame arrived in a good mood for dinner and we all looked forward to the night's fun and frolic. I had a busy evening receiving several regulars by appointment and one of Madame's that she couldn't fit in to her schedule. By two o'clock all I wanted to do is take a long hot bath and wind down.

The light over my bedroom was door turned on indicating that the evening was over, and I was off the clock. I headed straight for the tub. After drawing hot water, I heard a knock on the door and shouted, "Come in."

Jenny stuck her head in the door and said, "Do you have a minute?"

"Sure" I answered.

"Do you know a baseball player named Joe?" she asked.

"Yes, I met him last spring before school let out," I responded.

I got into the bath water because I wanted to soak in it while still hot and I told Jenny to come in the bathroom and have a seat.

She seemed embarrassed but seeing my friendly look, floating boobs and limp dick she pressed on.

"I met him a few days ago and he seems really nice. I went to the ballpark today and watched him practice then we had dinner. After dinner I thought maybe he would want to get friendlier and I was fully prepared to let him have anything he wanted. We went to his apartment and he fixed us a drink but didn't sit next to me. I sat on the couch and he sat in a chair across from me. I sipped my drink and then he came out with it. He asked me if I knew a "Tranny named Rachael."

"I didn't know what to say so I told him the truth. That I knew you from a place I worked but we were not close friends, just work mates."

He wanted to know all about you, and I told him I really didn't know much, just you were nice, friendly, beautiful and I found it hard to believe your anatomical configuration. He asked me if I had seen you naked and I told him no. It was just an accepted story around the work place and there was another TS there as well, so I never doubted it. He went on and on about how you broke his heart last year and how bad he felt over the situation. I didn't know what to do or tell him, so I just kept my mouth shut and listened.

"After he started to cry, and I had finished my drink I left and came home. I saw your light on and wondered if you would talk to me about Joe."

"Wow, that's quite a story," I answered.

"Look Jenny, Joe is an ok guy and I dated him for several weeks. We had a good time but never got intimate. He was always a gentleman and I never offered anything extra if you know what I mean. When he got desperate, I gave him a hand job and he went home satisfied thinking me a good girl."

"Does that really work?" she queried.

"It will work if you make it work, nothing is automatic with jocks."

I looked at her and knew something was amiss. "What's up, this isn't all about Joe?" I asked.

"I have a client that wants to do me in the ass, and I don't do that. I really don't want to lose the guy, he is a great tipper and I don't think he would mistreat me. Last night he offered me an extra hundred if I would let him do me in the butt. I couldn't refuse him, but I told him we had to wait until his next visit. I just wasn't ready for him last night and besides it would bring him back sooner. Then when he left, he handed me a one hundred dollar bill and said this is for the anal and he would collect next time he came. Now what do I do?"

"I guess you want to learn how to do anal?" I asked.

"Yes, I do but I am scared of it," she said.

"Have you ever tried?"

"No."

"Okay, I will teach you the basics and you will learn how to be safe and not let it worry you."

"Thank you, Rachael, I really appreciate your help."

"No Problem now let me finish my bath. Go home and take one yourself, come back here about nine in the morning and we will have a lesson."