Rachael Ch. 04: The Test

Chapter 4

The Test

I spent most of the coming school year with Charlotte. She had bought the car because she would graduate in the spring and leave for a job in the big city. I was just finishing up my first year at the state university. I still worked at the car lot and went to class. My father's estate and my financial advisor had been keeping me well financed and I had no real money worries. I didn't have a lot of free cash or time to spend on myself, so I really didn't dress up or go out that much. Charlotte was good company, she moved in for the last half of the semester and learned more about being with a male.

She moved out and away from the University in the Spring. I still miss her sometimes when I lay awake at night. She gave me a lot to think about and I enjoyed here emensely.

I was comfortable being a girl but not yet adapted to being a lady. I needed a mentor, so I kept my eyes open for another transsexual who might be able to do that for me. I didn't have any trouble finding boys or dates but that wasn't what I wanted. I wanted another person to teach me how to be a lady. Charlotte had been young and fun, but she was not a lady.

One evening there was a bunch of us hanging around in the University Center just doing nothing. A couple of guys I didn't know came by and tried to get some of the boys to go with them to visit a brothel they knew about. I could hear some of the conversation but not everything. It seemed to be a hard sell because most of the guys didn't have much free cash. Finally, three of them decided to go and I decided I wanted to know more about this place. I asked to come along and got a big laugh. Not to be discouraged, I pressed my point and since I had a car they relented and let me drive them.

The place was in an old residential district and a very big house. There must have been 4 floors and a dozen bedrooms. We all went inside and I kind of hung back just wanting to see what happened. One of the boys had been there before and he introduced the others to the hostess. The hostess kind of checked everybody out and when she came to me, the tomboy, she asked me what I wanted? I told her I was looking for work. I kept my voice down so the others couldn't hear, and the hostess picked up on my effort to be discreet. She said to wait there, and someone would come to get me. She then took the three boys into another room where they could make their selections for the evening. I had never in my life been with a professional woman and I wondered what that would be like. Maybe I could learn something.

Invited to sit and have a drink by the hostess, I moved to a love seat by the fireplace and sat down to watch. She brought me a glass of wine and I sipped and watched the traffic. There were several men leaving, some adults but most of them seemed to be young men from the university. That surprised me. You would think young handsome guys would not have a problem getting dates with girls and even some sex along with it. I had been keeping guys at bay all semester and suddenly thought maybe that was the problem. Too many of us were not offering a helping hand to the boys around school. Maybe I should do something about that. I sipped my wine and watched for about 20 minutes, then the hostess came to me and asked me to follow her.

She led me to a large door, which opened into an office where a very stately woman stood in front of this enormous desk and smiled at me. She looked to be in her 40's with an hourglass shape, large breasts and even larger butt. She wore a beautiful gold form fitting long dress that accentuated everything feminine about her. Her hair was wrapped and stacked on her head exemplifying her long stately neck, her makeup was beautiful, and she had rings on her fingers and earrings loaded with sparkling stones you had to assume were diamonds.

She walked toward me and said, "My name is Madame Silver and I own this establishment."

Her voice was husky and absolutely thrilled me. It sent shivers down my spine. The tone and resonance were like church bells tolling. I felt like I was in the presence of a goddess. She directed me to a chair and walked to a large ornate cherry wood bar and poured a drink, she didn't ask, she just handed it to me and then poured one for herself before sitting directly across from me.

"What can I do for you young lady," she said.

I told her I wanted to find a mentor, a lady I could learn to emulate, and learn from. She cocked her head and looked me up and down.

"Why do you think you need a mentor?" she countered.

I told her, "I wanted to become a gracious lady, refined and able to associate with others that had better breeding than I did."

"Did you have a mother to teach you?"

"No, my mother is a prude, stuck in a low-class world that I want to leave."

"Why do you think you can find that here?" she asked.

"I don't know the answer to that, my friends were coming here. I knew that professional women worked here, and I hoped that maybe something would work for me."

"Do you want to become a prostitute?" she said.

"Not exactly, but if this kind of work teaches me to be graceful and beautiful like you then I want to try it."

She laughed out loud and thought that was a funny way to express how the brood of girls she tended to appear and worked. I looked at her and something registered in me that I had not seen before. She really was elegant to look at, but her eyes seemed to be telling me something her words were not. She turned all business on me for a minute and asked me some questions about what I was doing at the university, did I have a boyfriend, how often did I have sex now, how old was I, did I use birth control, and a few more I can't remember.

Then she said, "Stand up."

I did, and she said, "disrobe."

I started to take off my clothes and she said, "Stop. Disrobing is not the same as undressing. It is an art form. You must learn to do this to excite and arouse the person you are disrobing for. Now, slowly unbutton your top, then act shy while pulling each arm out. Slowly unzip your skirt and push it over your hips even more slowly. If you were wearing hose, you would slowly unhook each garter strap and roll each leg down to the toes. Never look at what you are doing, always look at your partner, read his eyes, see what he sees, tantalize him with what you are doing and enjoy his stare. It is a sign of strength for you and enables you to maintain control."

I did all these things and tried to concentrate on her eyes, see what she saw. When I was down to bra and panties, she said, "Continue."

I took my bra off as slowly as I could, holding it up in front after I had released the clasp in the back, turning slightly sideways to look shy. She liked that and bade me to continue. I turned my back to her looking over my shoulder as I dropped the bra and began to roll my panties down over my butt as slowly as I could. The moment of truth was about to arrive, and I couldn't think of anything to do except face it.

She said, "Stop."

I had unrolled my panties to about the bottom of my cheeks when she said that, and I froze. I brought my hands up across my cheeks to sort of draw attention away from the thing I was hiding. "You're not a girl at all," she stated.

Now I was scared, she knew and there was nothing but fear in my heart at that moment.

"Turn around and walk toward me," she said.

I did as she asked, and she pulled my panties down to my feet and pulled my penis out from between my thighs. My balls fell out of their hiding place and I was fully exposed. She looked up and then cupped each of my breasts.

"These are natural, how long have you been on hormones?"

I told her, "Many years."

"Do you get erections?"

"I can but not without effort."

She then fondled my penis and I started to get a warm sensation and the beginnings of a hard on, but nothing great. She suddenly stood and took my hand and led me to a door behind the large desk. The door led to a bedroom that had a king size bed in the middle of it and several large cabinets on the walls. The woodwork was solid walnut and beautiful, and she pointed me to the bed where I climbed up and sat facing her. She began to disrobe, and I watched as she removed garment after garment. Slowly she revealed herself to me, inch by inch. It took at least 15 minutes for her to get down to her panties and then I understood what I had seen in her eyes before. She had a penis too and in fact it was quite a large penis. It was not erect but when she released it from its hiding place it seemed to hang almost to her knees. I never imagined such a thing. She held it in her hand and looked at me. "Do you like this?" she said.

I had seen some penises before but never anything like this. I just stammered, and she laughed a little and moved toward me.

"Put it in your mouth," she said.

I leaned over and did as she asked. It filled me up and it was so wonderful I could only moan with pleasure. As I sucked on the head, I could feel it getting bigger and bigger, filling up the caverns with hot rich blood, pulsating like a piston engine. Each beat of her heart came thru to my tongue. I could feel her energy and passion as she grew and grew. Her fingers found the back of my head and she whispered, "Open as wide as you can sweetie."

She began to push into the back of my throat, just hitting the gag reflex and pulling back. After several minutes of this gentle thrusting she pushed into the gag reflex and held my head firm in one place, I of course gagged.

She said, "relax, it will pass, and keep your mouth open."

I tried, and she withdrew only to push back there again, this time the gag was short and not as bad. She maintained her position and soon I felt her pushing back into my throat, I was breathing thru my nose and the gag reflex had abated. She was deep throating me on the first pass; wow is all I could think. She moved in and out, getting harder and harder all the time. I tried to close my lips on the shaft, but it was futile, I couldn't do it. She was just too big. Finally, she withdrew and stood in front of me, dripping what looked like gallons of my saliva.

"You are excellent, can you come back tomorrow?" she said.

"Yes ma'am," I replied.

The next day, classes went by at a furious pace. I focused on returning to Madame Silver and learning more about what I could become. I went home after my last class, showered, douched, and dressed in my most provocative short skirt and sweater. I put my hair up, added my best earrings and started to work on my face. Some of the things I needed were here, but I was missing a few, so my efforts were not as great as they could be. Dressing to impress was not something I was familiar with. I finally did the finishing touch with some red lipstick and I headed out for the brothel. When I got to the door, I was let in and the hostess recognized me from earlier. She motioned for me to sit at the bar and told me to enjoy a drink on the house. I asked for a glass of wine and sat quietly watching the flow of traffic and girls.

Couples would come out of the choosing room and go up the large staircase, returning later when business was done. While I sat there, I saw one very pretty blonde in a long flowing satin dressing gown go upstairs twice with different men. She seemed to be very popular and wondered what made her so special.

Soon Madame Silver appeared and beckoned me to join her. She looked me over as I walked to meet her, and she seemed to be pleased with my efforts. She turned and together we walked into the choosing room. I saw the room full of girls, some were young, some were old, dressed in all kinds of costumes that revealed what that girl's strengths were. I was amazed. I saw the blond I had admired before and noted how she made instant eye contact with me, almost like she was drawing me in. Her sex appeal was hard to deny and I was not attracted to girls.

Madam Silver walked right up to her and took her hand, leaned over and kissed her cheek. She then introduced me to Lisa and as I offered my hand she moved past the extended arm and pulled me into a hug and kissed my neck. Shocked and pleased I tried to return the buss and kiss. Madam Silver said, "Let's go have a drink and chat some." It was not a request and Lisa took my hand as we followed the boss to her office. Lisa did not know why I was there, but her actions were completely open and accepting of whatever I happened to be.

The office was as I remembered it and Madam Silver poured three glasses of wine and we sat around a small table. Once we were seated and sipping the wine, she told me that Lisa was a bi-sexual person and had clients of both sexes. I thought that was maybe why she was so popular. Madam went on and told Lisa that I was a transsexual and possibly would make a good partner for her with some of our clients. Lisa and I sat quietly while Madam explained what she wanted to happen.

She wanted Lisa to take me to her room and play with me. She wanted to know how I reacted to the female anatomy, sexual contact and what could I do along with what I would be comfortable doing. Lisa acknowledged the challenge and asked if she wanted her to start tonight. Madam said yes, right away, spend the next hour with her and maybe we can get both of you with a client before the night is thru.

Lisa and I left, and I followed her up the stairs. She took me to her room and let me look around, it was beautifully appointed featuring a large canopy queen size bed set high up off the floor. There was a large armoire and huge dresser and dressing table along with an overstuffed chair and chaise lounge. The room looked beautiful. I asked her if she stayed here and she said that it was her room for as long as she produced for Madam Silver. Some of the girls lived up on the 4th floor in a dormitory style arrangement and use the rooms on the second floor to entertain. The first floor held all girls that had permanent status. The third floor was for overflow, when business was good the girls used the rooms on the third floor too. There were plenty of girls to go around, probably twice as many girls as there were rooms available. It's all very competitive for us, we get paid well but we must produce. Slackers don't last too long.

She asked me to undress for her and I did the routine I had practiced while she sat on the overstuffed ottoman. She nodded and motioned me to come closer to her as I continued. When my breasts were exposed, she reached up and cupped one, squeezing a nipple and turning it pink, not to mention getting it a little hard. I continued undressing and after my panties were down, she examined my little soft penis. She seemed to contemplate what to do next and then she leaned over and put it in her mouth. Her hands went to my buttocks and pulled me closer while she sucked. It felt very good, much different than the physical act of masturbation. This was sensual and exciting. I felt my body start to become aroused. My nipples ached, my stomach fluttered, I had chills running up and down my legs, my knees got weak. I didn't know what to do with my hands. She stayed busy, pulling me into her deeper and deeper, both hands on my butt. I began to react to her with a rhythm of my own, pulling back and thrusting toward her hungry mouth, she sensed my state and stopped the rhythmic movement. She stayed still and just tongued me for a bit. Then she pulled back and examined my now erect penis. I felt shocked and uncertain as to what I was feeling. My dick ached, I wanted more, and my whole body was tingling with desire to fuck for the first time in since Charlotte.

She looked up at me and smiled, "you are going to be very good sweetie."

She got up, took my hand and led me to the large bed and after having me sit down started to take her clothes off in a very provocative manor. I studied her, and my manhood stayed erect watching the strip tease. When she finished, we were both naked and she moved to me and put her beautiful upright breasts against my face. She moved again and had me suckle one of the nipples. I felt it get hard and used my tongue to tease and rub it. She moved me to the other nipple and pressed my face deeper into her soft breast. I noted that her breasts were very soft compared to mine. She began to moan down in her throat and her body swayed easily in my hands. I held her hips and stroked her beautiful skin with my hands.

"I want you to lick my pussy, she said. Have you ever done that before?" she queried.

"I have never been naked with a woman before," I lied.

She nodded, moved away from me and pulled back the bed covers inviting me to join her between the sheets.

"I loved to cuddle," she whispered as we climbed into the bed together.

We faced each other, and she nestled in close against my chest. We hugged and let our bodies melt together.

"I want to teach you how to satisfy a woman, you may or may not always be able to get erect, but you can always satisfy her with other skills. Madame told me you are a good cock sucker and some of those skills will help you with a pussy, but it is much different."

She guided my face down over her belly and I moved slowly between her long beautiful legs. She propped herself up on a couple of pillows and began to explain what she wanted me to do.

"Rub your nose lightly down thru the soft pubic hair, teasing it a little, then bring it back up while sticking your tongue out just enough to reach thru and touch the skin. Observe the swelling of the lips, and then the erection of the clitoris. As I become aroused the little bud at the top will expose itself, the more I become excited the more it will retreat and pull back under the protective hood. Nature thinks it will be battered when the male begins intercourse, so the hood is there for protection. The clitoris is the most sensitive external part of the female anatomy. That little bud has more nerve endings than the whole head of your penis. Run your nose back down and extend your tongue until it is between the swollen lips and slowly bring it all back up until the tongue finds the clitoris."

I did as she instructed and found the taste delightful.

"Hesitate there and lick the little hard nub, feel it, put your lips around it and suck. Rub it with your tongue and make your senses aware of the heighten arousal of your partner. The first sign will be a quiver, maybe in her belly, maybe in her thighs, a slight tremble. Her breathing will increase, and you will be able to see her breasts move up and down faster. You must always be aware of her state of arousal . You can reach under her thighs and sometimes extend your arms and get a nipple between thumb and forefinger. Do that if you can, it makes it all work better. If you get a sudden gasp, or a noise escapes her lips you know you have made it to first base. She is now highly aroused and will be receptive to more and bigger orgasms. Achieving those is as hard and varying as anything on earth. You can only experiment with the things you know how to do and sense your level of success. You are doing very good, I am going to shut up and let you play now."

I did everything she told me to do, and after a few minutes I felt her respond, it was a small tremble but never the less I was doing something right. Then she told me to insert a finger, palm up into the soft opening of the vagina. I did so and continued licking and sucking on the clit. She wiggled me into the position she wanted to feel and told me to curl my finger up behind the pubic bone and tap the inside. As I did that, she began to move against me, her breath became labored, she thrust more and more, and I had a hard time staying down on her but I did my best. Finally, she relaxed and pushed my face and arm back with her hand.

She exhaled and said, "That was very good for a first time, come lie beside me now."