The Training of a Ladyboy

"Sorry I took so long Dave, I just wanted to look my best for today."

"Quite alright." He replied. "You do look ... good." He continued. "Really good. Pretty even."

Blushing I responded "You think I look pretty? Truth is, there is no point in my trying to look manly, so I thought maybe I should just try and look pretty."

"I think that is a wonderful idea. And with your hair done up and with the make-up you do look very pretty." Dave exclaimed and approaching me towered over me despite my heels. Reaching out a hand he placed a finger on my lower lip. Pressing my lips downward he let his finger slide off, causing my lower lip to bounce back to attention "Is that lipstick on your lips?" Dave inquired.

"A little yes, is that ok Dave?" I shyly asked.

"Oh yes, quite alright indeed. Actually looks really good on you."

I watched as the wheels turned in his head. Wondering what he was thinking I then heard him say "You know, maybe tonight we should just stay at home. You know, not hit the bars but just get drunk, I mean, have a few drinks, here at the apartment. You know, I can mix drinks and you can show me different hair styles you like, and try on different levels of make-up. You know, try on more make-up maybe, I can tell you what I think. Red lipstick would look nice. Yes, bright red lipstick I think would look nice on you."

"I think that is a great idea Dave!" I exclaimed. "And of course I can try on make-up, or clothes, anything you want. I will do anything you want Dave." I confessed, eager to be under the control of this strong and dominating man. He smiled at the admission.

We enjoyed our picnic very much. I hand fed Dave and he enjoyed the experience. I playfully licked and sucked on his fingers when he did the same for me. On the way home his hand slapped my knee at a joke and he ran his hand to my upper thigh. Before he could pull it away I placed my hand over his and he left his hand there for the remainder of the drive home.

We began drinking early that evening. Dave soon had me tipsy and suggested I try on different make-up. He soon had me in bright red lipstick and heavier rouge and eye shadow than I had on during the picnic. He said it was necessary in the darkness of the room. He asked if I had bought any other clothes that I wanted to try on and I mentioned that I did but that I was too shy to show them. He teased me and pleaded for me to show him but I remained too shy.

Then raising his voice he commanded "Bitch, I told you to show me. So do it now!"

Putting my head down in shame I apologized for not considering his feelings first and I promised to obey his every command from then on. He nodded his approval and I skipped off to change, happy that he still accepted me.

I shyly returned this time with a white body hugging T-shirt that did not cover my belly button and a tiny pair of white cotton briefs. Well, really they were panties. At the store I had tried them on and found that I preferred the feel of panties. My little penis just tucked nicely between my legs when I wore them and they fit very well. So I had bought quite a few new pairs actually.

Dave smiled broadly. Walking over to me he took my chin in his hand and raised up my eyes to his. "I like it." Dave said. "You like wearing panties?" Dave inquired.

"Yes." I responded, ashamed of myself.

"Don" t be embarrassed." Dave consoled. "They fit you well. You look good in them. Very pretty." Taking a broad finger from his free hand he pushed the finger against my lower lip. "I like the bright red lipstick too." He said as he pushed his finger between my lips. I flicked my tongue over his finger and sucked on the warm flesh as he continued "Do you have more panties in there to try on?" He asked. I nodded yes, his finger in my mouth and my eyes locked on his. "Try on all of the panties you bought and show me." He commanded. "And bring me the red lipstick." He added.

"Yes Sir." I responded. "I will do absolutely anything you say Sir."

Returning with a pink pair of silk panties he had me hand him the lipstick and ordered me to remove the T-shirt. I did so obediently, not wanting to offend my Master. Standing in front of me he told me to pout like a little bitch and when I obeyed he put more lipstick on my lips. Then he took the lipstick and drew circles around each of my nipples with it, highlighting them, making them appear larger. Then he wrote two words across my chest. On my left pec he wrote 'pretty' and on the right pec he wrote 'bitch'. Handing me back the lipstick he said "That is what you are. A pretty bitch. Now go and show me more panties!" He commanded and I ran off obediently, afraid to earn my Master's disapproval or wrath.

I returned with other panties and he kept sending me back until I came out with a tiny pair. They only came up and covered half my ass cheeks and left my dark blonde bush exposed above the panties in the front. These were in fact my favorite and so I had left them until the last. Dave said that they were also his favorite and for the remainder of the night I wore only those.

Dave put on soft music and told me to dance for him, and I obeyed. By now I naturally obeyed without question or hesitation. Passing by him once I staggered and landed on his large powerful lap. Dave placed hand around my slender back and the other on my leg. As I sipped my drink and continued to sit on his lap he caressed my calves, my thighs, my belly. He pinched the nipples that he had painted up. He put his finger to my mouth and I eagerly sucked upon it. He stroked my hair and told me that I was very pretty and that he was sorry he hadn't noticed sooner. I held him tight and told him that it was alright, that now I was where I belonged.

Dave said I looked tired and should run along to bed and that he would drop by in a few minutes to ensure I was OK and hadn't drank too much. The truth was that I hadn't drank much at all, but I agreed. Pulling back my bed clothes I lied myself on the sheet on my belly. I pulled my little pecker forward under my pretty panties. I thought I knew what was coming next.

A few minutes later Dave entered the room. Sitting on the bed beside me Dave stroked my hair. "You awake?" He inquired. No response. His hand slid down my back. Over my ass. Down one leg. Up the other. Then between the exposed crack of my ass. "You sleeping sweetie?" He inquired. No response. I felt a finger reach between my cheeks and tug at the tiny panties. Soon if felt them sliding down my legs, to my knees, my ankles, and off. I was nude.

Dave's hand explored the soft hairless flesh on my bum. He gave each cheek a little slap. With my eyes closed I heard as he undressed. Then I felt as he sat at the bottom of the bed. My legs were forced apart. I did not resist at all. A hand went under my waist. I was raised to me knees. I naturally thrust my ass upward and outward. Again he gave each cheek a little slap. I felt his massive body position itself behind me. A felt a cold wet sensation as something was rubbed onto my anus. Lubricant? I guessed. I felt something hard and round press against my anus. Oh Christ, I was about the lose my virginity. But not in the way I had imagined! Dave was gentle, but occasionally rough. I got the sense he did not know what he was doing and I certainly had no idea how to proceed. So we both trusted in our instincts.

I knew that he thought of me as a girl, and that was alright. I knew that he liked my ass because from behind I looked like a girl. I would make sure I almost looked like a girl for Dave. I would hide my dick, and ensure my appearance was as feminine as possible for him. I knew in his mind he was slowly sliding his dick into a woman. Her vagina. Her anus. I didn't know which he imagined my anus to be. Didn't care. My butt could be either for him, whatever he wanted it to be. All I knew was that I wanted to serve Dave, to serve that cock I was quickly coming to adore, worship, cherish, love. I didn't care which hole he imagined he was shoving his dick into. All I knew is that I wanted that cock in my hole and for Dave to fuck me, and only me, as often as he wanted.

I felt the massive purple head begin to penetrate my ass. My anus spread wide and I felt a quick pain inside. I cringed and instinctively pulled away. Dave seized me by my hips and pulled my back. "Take it bitch. Take it like the slut you are. I'm going to fuck this nasty little cunt of yours tonight one way or the other, so you might as well just relax and let yourself get fucked like the little slut I'm going to train you to be."

I moaned at the suggestion and relaxing felt as his dick sank an inch into my ass. I laid there in pure bliss, and for the first time in my life I felt Dave's big wonderful beautiful precious amazing cock enter his new sluts welcoming and eager hole. Soon his whole length was inside his bitch. And his bitch moaned in sheer delight. It had been a bit painful starting out. But now the pleasure was overwhelming. I felt a surge of energy and arousal rush through my body. Dave pulled his dick backward leaving only the head in and I wanted to beg him to shove it back it, but I maintained my pretense of being asleep.

Soon my dreams and wishes were fulfilled and the thick column was soon balls deep inside me again. Dave began to fuck me in long slow strokes. I moaned desperately. His pace increased. His thrusts intensified. He began to ram hard against me. Fucking me faster and faster, harder and harder I thought my body was going to rupture. But it was Dave's body that ruptured, exploding deep inside my colon. My lover had fucked the virginity out of me and now had cum inside my body. He had placed his stamp on me, claimed me as his own. He owned me now. I was his fuck toy. I would remain his faithful and loving bitch, ever willing and eager to satisfy that perfect cock. That cock that I would come to worship and love and serve unconditionally.

My loaded ass sank back onto the bed as Dave extracted his satisfied meat from my gratified anus. I enjoyed the feeling of his warm wet cum leaking and seeping out of my asshole and down my legs. Sitting beside my pillow he rolled me slightly over. I kept my legs crossed to conceal my tiny erect penis. I would jerk that off after he left the room, remembering the wonderful feeling of his own much more impressive cock inside me. My Master stroked my hair and caressed my face. He told me sweet words. That I was pretty and sexy, that he loved fucking my cunt, that he loved how I sucked cock, that he loved filling my mouth and my hole with his cum. He told me that I was his bitch now and no one else's and that he would train me to be the slut he needed me to become.

Then he leaned forward and kissed me upon my painted lips. I had sucked off my Master twice. He had ass fucked his horny slutty bitch. And now we kissed. This would always remain the order of the affection exchanged between us. A great deal of cock sucking, quite a bit of ass fucking, and the occasional tender kiss. But this was our first kiss, and I was not going to lose the moment. With my eyes closed, in my state of pretended sleep, I kissed my first and only lover back passionately. We locked lips and he slipped his tongue into my mouth. I sucked it eagerly. I stuck out my tongue and he licked at it playfully with his own. One more quick kiss and he was gone.

True to his word Dave trained me to be the slut he so wanted to find. My name now is Chantal, and I love my man, the only man I shall ever fuck. My transformation is complete. In heels, a tight short skirt, an open blouse to reveal the small perky breasts I acquired with the help of the wonders of modern science, my hair grown further out, with my ears pierced, with my make-up and slut red lipstick, I look just like a woman. Dave would introduce me as his girlfriend, and later as his wife. He remarked that I made many men's heads turn, and even saw jealous wives scold their husbands for having their eyes linger upon my form too long.

I tape my tiny little soft pecker down along the inside of one leg so in panties or a skirt I have the exact bearing of a woman. In time I opened my eyes while he was laying on top of me, fucking me, and he smiled at me, and we kissed. I told him I loved him and loved him fucking me and loved sucking his cock. He said he loved me too.

Dave said that his slut would need to suck him off twice a day and fuck his dick once a day now that I was his awakened little bitch. I smiled and gladly agreed. He said he would train my cunt to get fucked more easily, and that he most certainly achieved. I keep a little tube of lube and with just a dab he slides into me as easily as any vagina was ever entered. Dave taught me to fuck him from on top, his favorite positon. With him sitting in a chair I sit on his lap and sliding my cock into my ass - my cunt - I use my legs to pump up and down as he enjoys squeezing and teasing my newly grown little tits. I love my man. I love his big beautiful cock. I love fucking my man. And my man loves fucking me. Chantal is a very well fucked bitch indeed. I am so glad that I found Dave. He is the bestest friend I have ever had. My friend. My lover. The man who's cock I exist to satisfy and to whom I freely offer every aspect of my body. Not the life I expected. But the life I am so very happy to have found.