. 01: the Transition

My name is Rachael, and this is the continuing story of my transition from a teenage boy to a grown woman. In the previous book I attended and graduated from Radford. My boyfriend, Steve, went on to play professional baseball and I stayed in Radford, returned to school and studied advanced biology for two years, becoming educated in all the ways of transgender. Steve went on to play baseball but never made it out of the minor leagues. He stopped writing after the third trade to another farm system out west.

I returned to the brothel to live and study. Madame Silver and I studied and took clients by appointment. She expressed an interest in the biology of transgenderism and we spent many a night exploring the field. She never considered having the change, she loved the way she lived and the cock between her thighs.

I earned my Master's Degree and figured it's time to do the deal. I signed up for a transgender reassignment program at a hospital in Jacksonville. The program would be six months in duration and I would have to move into an apartment and live there for the whole time. The cost seemed outrageous, but I had saved the money and it was my life's ambition.

The program administrator offered me a low paying job in a laboratory, that might defray some of my living expenses and provide me with access to hospital support and insurance. Madame Silver and I enjoyed a wonderful final session of unending passion. We both knew that it would be my last time as a functioning male. I made the most of it, fucking her as many ways as possible and enjoying both the sex and her company.

I pondered going out and trying to find Jenny for one last pussy fuck but thought better of it and prepared to leave town without being with another woman.

I left the next morning, hoping to bring back a brand-new pussy for Madame to have her way with. The thought of giving it up to her became constant in my mind. She on the other hand, constantly reminded me that we could live forever like we were, and she would be happy with me having a dick. The conflict was deep in me, I felt in some part of me that I wanted this for both of us, and another part of me saw it as selfish. She liked having her dick and I was giving mine away. Madame Silver should have been all the woman I would ever want or need. In the end, I decided to have the surgery and look forward to having her big dick in my new pussy.

The hospital, the surgery and the job all went almost perfectly. There were no major hitches. I did all the class work they required, talked to the shrinks until they were blue in the face, and tendered myself to the surgeons for multiple surgeries.

They took my male genital organs first and allowed me to heal somewhat before they began the process of creating a vagina and hopefully some sexual sensation. I didn't realize at first that they turned my penis inside out and stuffed it back up inside of me to heal itself and become the lining of my new vagina.

The prostate, scrotum and the testicles were gone. I often wondered what they did with them, but never asked. I didn't have a lot of pain. I did have a little discomfort and urination became a problem on several occasions, but I suffered through it. When they finished I owned a bald pussy, lips and clitoris included. I couldn't believe they fixed me.

The doctor admonished me to allow her to heal for several months before I tried her out and I promised I would. The last thing I wanted to do is damage my new pussy. They required that I stay there for an additional 30 days to observe the healing and further advance my training on how to take care of myself and my new complete gender reassignment. Since I enjoyed the job and the lab work I stayed and life went on. I wrote to Madame often, described the process in as much detail as I could without medical terms. She wrote back and let me know that she missed me dearly and could hardly wait until my return.

Dave, worked in the lab with me and he hit on me a few times. I finally agreed to go out with him after my doctor's release. The first time out, Dave acted a perfect gentleman, we went to a nice downtown restaurant, drank some wine, ate some dinner, and he wouldn't even let me get half the check. He walked me home and we shared a good night kiss. He knew my situation and I guess it fascinated him, but he didn't ask me for sex. I think he knew I wanted to save my virginity for a while or at least until I totally healed. He understood and never pressed me.

He asked me out again the following Friday and I agreed to meet him. We were sitting in a restaurant and I felt particularly randy. I slipped off my high heel shoe and moved my stocking clad foot to his crotch. I sat across from him and made the reach easily. He looked at me with a sneaky grin and I knew I did something he liked. I rubbed him into an erection and massaged his cock thru his pants with my stocking until we were both grinning like two teenagers.

"I thought you wanted to save that new pussy?" he said.

"I am," I replied.

"Then we shouldn't be doing this," he retorted.

"I know, but I want to. I want to feel your cock. Can I do that?"

"Okay, just so I know what I can expect."

"You can expect anything you want, hand, throat, asshole or all three."

"Just no pussy," he said.

"That's right, no pussy."

"I can live with that," he said thru his grin.

I drew back my foot, put my shoe back on and gave him a minute to recover before we paid the bill and walked hand in hand out the door of the restaurant. We walked slowly back to his apartment and talked about nothing at all. My mind full of the desire for the sexual relief he could give me. I hoped he felt the same thing. He looked nice, he was polite and respectful. I knew he wouldn't hurt me. I guess I felt safe. Little did I know?

He opened a bottle of wine and we sat on his couch for a while still chatting about work and my recovery. I got really antsy waiting for him to make a move. The last time for me was a long time ago and I decided to make the first move. I swung across him and straddled his lap, leaned down and kissed him as hard as I could. He returned the kiss and ran his hands up my back, caressing my skin and finally releasing my bra. I leaned back so he could help me out of my blouse and press my nipples into his face. He sucked each one while massaging the other one with his hand. We kissed some more, and it got hotter and hotter.

While sitting across his lap I could feel his manhood pressing on my new vagina. I finally slid down and released his erection from his jeans and boxers. He lifted his hips and I pulled them free, pushing them down around his tennis shoes. Soon I pressed him between my lips and he went out of control. He grabbed my head and shoved me hard down on his penis. I sucked a lot of cock before tonight, but this was different. His dick was enormous, super hard and leaking pre-cum like a faucet. He spilled so much of it at one point I thought he ejaculated.

He wouldn't let me up. He held me down and kept thrusting up into my mouth. I gagged several times, and almost threw up all that food and wine. It didn't seem to bother him at all, he just kept fucking my throat and I kept trying to accommodate.

Finally, I got my hands down on something solid and pushed up away from him. I was gasping for air when the first blow landed. An open right hand to my left cheek. It stung like a bitch and I wasn't sure what happened, sexual play or damage intended? Shortly I found out this is not play for him. The second blow was a fist to my left eye. That really hurt. I reeled back into an upright position, partly to get away from his reach and partly to take stock of the damage. "What the fuck!" I shouted.

"Finish me off," he commanded as he reached for my head.

"I don't think so," I responded as I moved farther away.

Just as suddenly as the first slap he leaped onto me, pushed me over backwards and sat on my chest. Now he hit me with both fists, first the left and then the right. I was pinned down with no way to respond. He tried to put his dick back in my mouth and hit me at the same time. I got my hands under his ass and pushed with all my strength. He went up over my head and landed on his face in the coffee table.

I got to my feet grabbed my blouse and started for the door. He scrambled to his feet, grabbed me from behind and said,

"Not so fast bitch, we're not done yet." With that he spun me around and clocked me again with his big right hand. I saw stars and my knees buckled, sending me to the floor again. That was the last thing I remembered for a while.

When I finally regained consciousness I found myself tied across a single bed face down. The ropes burned my wrists and ankles and I could tell that my clothes were gone. My panty hose were pulled over my eyes and everything looked blurry around me. I lifted my head and there he sat, resting in a lounge chair looking at me.

"Well there she is," I heard him say, "Are we having fun yet?

He rose from the chair and walked to the bed where I waited for him, motionless and immobile.

The first blow hurt, and I couldn't figure out what he used to deliver it. Then I realized he held a whip in his hand and he dragged it slowly across my rump. Then without a warning he would pull it back and hit me hard with it, bringing up welts that I could feel.

This is not good, I thought.

The whipping continued soft then hard and moved down my ass to my thighs where he continued the torture.

This kind of pain is something I never felt before. A stinging and burning all on the surface of my skin. My skin felt like it was on fire.

He came back from the bathroom with something and I felt him smearing lotion of some kind over my wounds. It felt cool and refreshing. He was putting out the fire. His hands rubbed down between my cheeks and close to my new vagina but stayed away.

He massaged my asshole with his lotion and fingers, pushing one, two and then three fingers into me and stroking me hard, painfully hard. Then he got on top of me and I could feel his cock trying to penetrate me. He couldn't get it in. The angle was wrong and all he could do was push and pound his erection into the area around it. I tried to clamp it up as best I could and pull my hips down into the bed further preventing his penetrating me.

He finally figured out he couldn't butt fuck me without my help and said, "You can either help me get it in or I can go to the hole I know how to get in."

With that he rose up and began slapping my ass cheeks, leaving big red handprints that I of course couldn't see. I realized that I needed to stop fighting and let him get himself off, maybe then I could escape. I eased up off the bed with my hips and he sensed what I was doing. I could feel him lubing things up again and readying for a second assault.

I mumbled, "Slowly," and rose to meet him.

He figured it out and finally slid in and slammed his cock right to the bottom. It hurt like a bitch, sharp penetrating pain, but I knew how rectal pain felt and I wasn't worried about damage. Besides, many months were gone since I felt the pleasure of a cock in my ass and a little pain was to be expected.

He began to pull back out and slam back in again. He liked the sensation of parting the pucker spot. Again and again he pulled out and pushed back through the entrance. I encouraged him to fuck me, but he wanted to torture me instead. Pull out and jam it back in, pull out and jam it back. It was maddening.

I like being fucked, I thought he would do me, but all he wanted was for me to be in pain. More slaps, more jabbing, more humiliation. I don't know how long this went on because I passed out again. I don't know what he did when I went limp, but when I woke up I found him back in the chair stroking his big dick with lotion.

He saw my eyes open and said, "How do you feel, now?"

"I hurt," was all I could offer. My face hurt from the punching, my ass sore from the fucking and my butt cheeks hurt from the whipping. Other than that, I was just hungry.

He continued to play with his dick while I watched and wondered what he would do to me next. I was truly helpless, and I didn't like the feeling much.

After we stared at each other for some time he stood and dragged the chair over to right in front of me. He sat down again, with his cock in my face. He pulled my hair until he lifted my mouth to the right spot and then let my face back down over his dick. He put it full in my mouth and all I could do was tongue him at this point. He grabbed some more of my hair and began to raise and lower my face over his swollen cock. I fought off the impulse to bite him, I just couldn't do it. I felt him getting harder and harder the more he went down my throat. Then he backed the chair up suddenly and started jacking himself off with violent strokes. His face went red, his breathing quickened and right in front of my face he spewed his seed into his hand. I looked up to see what he did, and to my surprise, he brought his hand full of semen over and pushed it up against my lips.

"Eat it all, bitch." I stuck out my tongue and lapped it as best I could. I found it a difficult position for me to work in, but I did my best. Then he brought the chair back under my face again and holding his dick up to me said, "Lick it all clean." I did what he demanded and enjoyed the taste of it. What I didn't realize was this is my reward for being a good girl.

When I finished cleaning him up he walked over and released the rope that held my hands to my feet under the bed. Pulling the rope from my hands out from under the bed he told me to stand up if I could. I did, and he bent over and took the ropes off my ankles. With my hands still tied in front of me he led me by the wrists into the bathroom. The room looked huge, almost as big as a normal bedroom. The shower looked like something from a locker room.

"Get in the shower."

I stepped into the shower, and he looped the bitter end of the rope over a hook in the ceiling, pulled my hands up over my head and secured the rope down to a cleat on the near wall. "Shower time," he said.

The showerhead was on the end of a hose and he held it as he turned the water on. Soon the water warmed up and he washed me down from hair to toes. He used a soft cloth and soap that smelled like flowers. I began to relax and didn't fight him when he wanted to wash my private areas. He treated me gently, but I was still tied up and my mobility limited. He stepped back and admired his work, pinching my nipples and my soft pink breasts.

After shutting the water off he got a large fluffy towel and gently padded all the water off me. Then he took extra time to rub my bottom, giving special attention to the welts. He brought some salve and applied it to my whole bottom and the backs of my thighs. I must admit it felt good. He also put some ointment on my cheeks and one eyebrow. The pain in my face had gone away but he must have seen some damage in the shower.

When he looked satisfied he took the rope down, unhooked me from the ceiling and led me back into the bedroom.

"We have a little time before my first appointment arrives and I want to teach you some more discipline."

He led me to a back wall and once again looped the rope that tied my hands together over a hook in the ceiling and tied it off to a cleat. I stood comfortably but my arms were back over my head and my shoulders a bit uncomfortable.

I watched him walk across the room to a tall chest of small drawers. It looked like a large jewelry cabinet. He opened a drawer and selected two objects that I didn't recognize.

Returning to my side of the room he proceeded to attach clamps to each of my nipples. There were little thumbscrews on them and he watched my face as he tightened each one up. When I winced, he stopped turning and then backed off a touch. He smiled as he walked away and went back to the chest. Opening another drawer, he selected two more items and returned to me. "Do I have to force your legs apart or will you cooperate?" he said.

"I will cooperate," I replied.

I moved my feet apart and he reached up between my thighs to my newly made pussy and applied a clamp to one of my new labia. Then he put the other clamp on the other side. Once again, I winced but I didn't say anything.

"You have to get used to these before I put weight on them to stretch your lips out." Then he walked away and left the room.

Well, here I stood, knees apart, clamps on my sensitive areas wondering what's going on. I needed to start thinking something pleasant or I would go start raving mad with the pain. It wasn't so bad that I wanted to cry, more aggravating and embarrassing than anything else. Being uncomfortable made napping difficult. I did my best to ignore the clamps, but my mind kept coming back to the pain, A sensation that I would never forget and one day learn to love.

I don't know how long I hung there before Dave returned. He checked my restraints, removed the clamps from my nipples and I felt the fire I would learn to crave. When he removed the clamps from my labia I expected the same burning, but it didn't happen. Perhaps being manmade they reacted differently. He placed all the clamps in a jar of liquid. Returning to me he took the rope down off the ceiling hook and said, "Follow me."

He led me to another corner of the room where I saw some large animal crates. He opened a door and said, "Please get in and I will unbind your hands."

I did, and he untied me, looking for any damage on my wrists. I didn't have any, the bindings were very soft. "Are you hungry?" he asked.

"Yes, I am," I answered.

He left the room and returned with a tray of hot oatmeal and a bowl of diced peaches. He put the tray inside the crate and closed the door. "Would you like coffee or tea?"

"Coffee."

He left again and returned with a large mug of black coffee. "I don't have cream and sugar, you have to drink it black."

"Okay."

With that he left, and I ate. I was very hungry and the bedding in the crate soft and comfortable. After eating I relaxed and fell asleep.