Rachael Pt. 03 Ch. 16: The Card Game

The Card Game

AUTHORS NOTE: Readers who have read Rachael's story from the beginning will recognize this scene. It marks a major turning point in Rachael's life and a turning point in the story. The past is past; we have returned to the beginning and the future is here now. Enjoy.

George asked me to join him for a card game at new location on one of our regular Thursday evening sessions. The card game was Friday night and he thought it might last a long time. He wanted me to be a maid for the night, serve drinks and food, service the other players.

I agreed to doing the card game and the next day Dave told me he was taking his wife to Radford in the airplane for the weekend. That freed me up for the whole weekend and I could spend it with George. I was hoping for some sex with that giant cock once again. It had been way too long, and I needed some good sex.

When we arrived at the party, I discovered a kindred spirit. A fellow slave was serving his master who was the host for the evening. They were playing bridge which always gave the players opportunity to take a slave to another room for fun and games. Punishment was usually not a part of the night, plus I was excited to meet another slave.

Sally was a guy dressed in a black and white maid costume wearing a blonde wig and high heels. I was surprised at how good his makeup was. I wasn't even sure it was a guy at first but some of his mannerisms and body language gave it away.

We spent some time sitting on our station pads and got to chat as long as we kept our voices low and listened for the needs of the card players. From time to time one of them would come and take one of us to a bedroom and get whatever he wanted. George came for Sally early and I heard him demand a blow job. Sally reached for George's zipper and George said, "Not in front of Rachael." Sally took him to the bathroom.

Everybody seemed to want my pussy and I couldn't remember the last time I was fucked so much that way. Nobody seemed to want my ass, I guess they did that with Sally. I was getting sore by the end of the evening, bad lube and too much friction.

When the evening was over, and the money changed hands, George told me to stay and help clean the place up. I could call a cab to get home and he would see me Sunday morning for our regular meeting. I guess no big George tonight for me.

"George, I didn't bring my purse, I don't have any money to pay a cab."

"Too bad, walk or hitch a hike."

"Yes, Master." I grumbled, and he slapped me.

"Do you want me to beat you here and now?"

"No, Master, I will be pleased to find a way home."

"Good, and I will tell the host that you are to stay and behave until he is finished with you."

"Yes, Master." I chirped.

Sally and I cleared the dishes, stripped the bedding and put everything in either the dishwasher or washing machine. I asked him about his life and how he got to be a cross dresser. He began to talk about his life as we worked, I just shut up and listened.

He had grown up with three older brothers that were all jocks. They played football, basketball, baseball and ran track. He was not real athletic and instead of playing sports he stayed close to his mother.

"Did you ever question your sexuality?" I asked.

"Yes, when I was a teenager I looked male but wanted to be a girl."

"How did you deal with it?"

"I mostly didn't. I stayed home, did chores for my mother and held on to her when I had conflicting thoughts. I confided in her and she didn't really try to make me a boy. She had three other boys to keep, and I could be all the girl I wanted to be as far as she was concerned."

"When did you start cross dressing?" I asked.

"I guess it was my middle teen years. I would take my mothers dirty panties out of the laundry and put them on for a while under my regular jeans. I tried a bra one day, but it was too big and just bunched up under my sweatshirt. I always felt guilty about that and probably never got over it."

"Is that when you became Sally, did you like being a girl?" I asked him

"No, my name then was Samuel. I did like being a girl though and thought a lot about how life would be like if I could stay that way."

"When did you become Sally?" I asked.

"Much later in life."

"I couldn't stand being a boy in high school either. What did you do after graduation?"

"I went to college and I tried to join a fraternity. I wanted to become a mainstream man. I couldn't do it. The brothers in the house thought I was queer and harassed me worse than the jocks did in high school.

One night after I had served dinner and done my chores around the fraternity house as a pledge, they took me to a brother's room upstairs. There were four of them, all brothers and they made me strip, made jokes about my small penis, large nipples and flabby middle. It wasn't long before they had me on my knees and one of them pulled out his dick while two others held my head and he forced his cock into my mouth.

I wanted to be a brother and I thought in the back of my mind that this was part of my initiation ritual. I didn't fight them so they relaxed and then all of them pulled out their dicks and started to flog themselves. Soon they had me on the bed sucking a cock when someone pulled my pants down. Another one held my ankles and one of them proceeded to penetrate my ass with his dick. This was new to me and although it was uncomfortable it really wasn't that painful, and my male ego didn't object. They all fucked me before the night was over and laughed as I walked out the front door to go back to my dorm."

"That must have been horrible." Rachael said.

"I knew I had been abused and brutalized, but I didn't feel like I had been physically damaged. When I got home, there was no blood in my underwear and the minimal pain of the incident had waned. I sat in my bed that night and fantasized about being a gay man and having more anal sex. I was still conflicted. I wanted to be a man, but it looked like life was taking me in a different direction. The next day I received a registered letter from the fraternity informing me that I would not be offered a place in the brotherhood. That was a disappointment, but I wasn't surprised after the rape."

"Did you enjoy the school?"

"I was discouraged at my attempts to become a man, so I dropped out of college and joined the Army. Basic training was very physical and difficult for me, but I graduated and felt some pride of accomplishment. I was recommended for Officer Candidate School but not selected for attendance. I had the grades and leadership skills but lacked the military bearing that officers need to lead troops in battle."

"What was Army life like?"

"I went to administrative school and learned how to be a company clerk. Fill out all the forms, keep track of everything and generally run the office. My typing skills were excellent and after graduation I was assigned to a troop depot in Missouri. The Ozarks of Missouri. This was the middle of nowhere and there was very little for the troops to do except train, eat, sleep and bitch about it.

As the company clerk I had my own office and was even given a small room of my own in the barracks. I didn't have to sleep in the squad bay with the rest of the headquarters platoon. The company First Sargent had a similar room at the other end of the billet. I enjoyed my privacy. Of course, everybody used the same latrine which featured a group shower, exposed toilets and a piss trough. Sinks with stainless steel mirrors and cold water most of the time.

"Did you enjoy watching the other men shower?"

"Yes, to some degree. One night late I went down to the latrine to defecate. Dinner had gone through me way too fast. When I entered the room, I heard some voices in the shower and didn't pay any attention to them. Soon the sounds of men having sex came to my ears from the shower. The water was running but there was a lot of grunting and encouragement going on. When I finished my crap I just had to look. What I saw took my breath away.

There were three guys in there and two of them were passing the third guy back and forth taking turns fucking him in the ass. I was transfixed and then I was spotted. One of the guys doing the fucking was the First Sargent. The other guy I recognized as another Squad Leader Sargent."

"Did you go into the shower with them?"

"No, the First Sargent saw me standing there but I turned and went back to my room. He followed me, and I quickly became introduced to the world of barracks sex. There were no women around. The only women on the base were married to the officers. The small town outside the gate only had a handful of worn out whores for the eleven thousand men on post. Most of the guys would rather fuck a buddy in the latrine than pay for one of them.

The First Sargent began to come see me on a regular basis and introduced me to anal sex in a big way. It wasn't long before the word got around the barracks that the Company Clerk was a good lay. I didn't discourage them and when the pressure of the work and training got to be too much they would come to me for relief. I liked it."

"Where did you get the name Sally?"

"The First Sargent began calling me that several weeks after he started with me. I was his pet and he wanted to have a pet name for me. The name stuck, soon I was known as Private Sally. Someone even put a sign on the door to my room that said Sally and I discovered that they would turn it over when someone entered my private quarters for sex. That way no one would interrupt us."

"How long did you stay in the Army? Did you get to travel any?"

I did four years and I was heavily recruited to sign up for another four years, but I had been stuck in the same post all my service years and I had had enough of Missouri and the Army life. I never went anywhere and neither did the First Sargent. Lots of troops came and went but we stayed there and trained them."

"Did you ever get promoted or given medals for your service?"

"Not long after I became the go to guy for relief, I was working in my office one day and the Company Commander and the First Sargent came in and brought me to attention in front of my desk. The First Sargent cut the Private's insignia off my arm and handed me the patch worn by a Specialist Five. I was being promoted two ranks with a giant raise in pay. I was stunned, the Company Commander smiled and told me he was proud of my work and that I earned the promotion. The First Sargent just smirked. I knew who made the recommendation, and he made it happen. We had a big party that night to celebrate my new rating and I got to fuck the First Sargent for the first time."

"I guess you came back to Richmond when you got out of the Army?"

"I did, and I looked around for some way to enjoy what I had in the barracks in civilian life. Most of what I found was seedy, dirty and not very appealing. The gay guys I met were not my kind of people. I didn't enjoy their company at all, so I looked for a better way to go out.

That's when I discovered cross dressing and really put my mind to it. I found a lady in a dress shop that served cross dressers and introduced me to several men who liked to dress up and party. She had her own agenda and would take me upstairs to her apartment and teach me how to dress, do makeup, care for a wig and be a sexy woman. In return I gave her what she needed. She didn't like rough men, she wanted a gentle man to take her to her bed. I liked her, but it was never love."

"What did you do when you dressed up?"

"Most of the time I just pranced around the room in front of a mirror. I taught myself how to walk and worked on my body language. One day I stepped out of my apartment and walked down to the park. Well, let me tell you. I had several men approach me and ask me if I wanted a drink or to party. This was good, and I soon figured out how to handle my suitors. I usually let them kiss and fondle me but when we got in close quarters and they wanted more, I would pull back and tell them I was a cross dresser and not a woman.

That usually cooled things off but sometimes they would be curious and take me home to find out the truth. Most of the time I gave them a blow job, and never saw them again. Sometimes they would call me back and fuck me. I had several regular guys that would take me home but rarely out to a club or even dinner. They just got horny and wanted to fuck my ass. That was okay with me, I enjoyed all of it. No relationships, just casual sex with random men.

"How did you end up with a Master?"

"He was one of my regular call backs. One day he told me about S&M and I expressed an interest. He thought I would make an excellent sub and he trained me. I got some pleasure out of it. The pain was tolerable but his ability to satisfy me sexually was unsurpassed. The way he treated me, the way he fucked me, it was all harsh on the surface, but he made me feel like I was important, and he wanted me."

"Dom's tend to do things that way. Maybe it's skill they learn but more than likely it's a gift or a curse, depending on your view." Rachael added.