We were always taught to never shame the family. As we were poor we still had respect and everyone did their part to bring in some money to the family. At 17 years old I had just been fired from my third job as a busboy in a restaurant. As we sat around the table eating our rice father yelled out “You have shamed the family again. If you don’t start bringing some money to this family by the end of the month then you are out.” I began to cry and went outside to wallow in my sorrow. Mama came out and put her arm around me to comfort me. After I stopped crying she said she could help me with a new job but I would have to do exactly as she said. I respected momma and trusted her so I agreed. I knew she started my sister in the business of being a call girl and that she made a lot of money for us by going to bed with all the horney soldiers in the nearby camp. She explained that the call girls were more respected and treated better than the local barroom girls because they were more selective and demanded a higher price. I thought about it, how I idolized my sister and how I secretly wanted to be like her so I agreed. Mama hugged me close and said we would start in the morning. In the mean time she gave me a pill and said it would help me sleep. I took the pill and went to bed thinking about what I had just decided.
The next morning momma told me to get a bath and that she had to get some things and would be back soon. When she came back she said it was time to teach me about my new profession. She explained that she was going to turn me into a beautiful call girl and that the fact that I was a boy dressed as a girl I could possibly make more money than my sister. Momma asked me again if I was sure I wanted this as once we started there would be no turning back. I quickly thought about it and said yes. She told me to get undressed and bend over. As I leaned over the table I felt a sharp sting on my butt. After that (I learned it would become a routine) she told me to get back in the bath. In the warm water she started to teach me to shave my legs, under my arms and around my crotch. Once finished she rubbed oil into my razor burned skin, I now felt smooth and soft as a babies butt. Mama told me I had a lot to learn and to pay attention if I wanted to be good at this. She brought out some under things and some surgical tape and said time to teach me how to dress.
First she showed me how to tape my penis and balls up under between my legs so they wouldn’t show a bulge when I had my panties on. As I looked down I couldn’t believe how it looked like I had a vagina, there was nothing protruding from my flat tummy except my pubic hair that had been trimmed into a feminine “V” shape. Next she handed me a garter belt and some stockings. She explained that if I put my panties on first that I could not take them off because the garter belt would be in the way. I slipped the lacy belt around my waist and with a little help got it hooked. I sat down and momma started to trim my toenails. She said I must keep them trimmed to prevent getting a run in my stockings. Next she showed me how to roll the stockings and put them on. The feel of the nylon on my soft legs was incredible. She handed me a pair of panties and I stepped into them. Before I pulled them all the way up she showed me how to put a panty liner in them explaining that it would not get my panties dirty when my penis leaked. With the liner in place I pulled my panties up. I couldn’t believe how much it looked like a girl, with no tell tale signs that I really had a dick. She handed me what looked like a bra and explained that it was a training bra. This was to get me used to wearing one when my breasts grew. She showed me how to adjust it for the most comfortable fit and how to fill it with tissues to look like I had small tits.
Sitting there in my new under things I looked like a little girl sort of. “Next comes the make-up.” She said. Momma told me to pay close attention as I would be doing this myself in the future. She taught me all about the foundation, blush, eye shadow, lipstick and perfumes. She said I learned fast and was pleased with the way I looked. Momma handed me the rest of my new clothes and I got dress in a skirt and blouse. She spent the rest of the afternoon teaching me how to walk, sit, talk and act like a lady. The afternoon went quickly and soon it was suppertime. Father came in and took one look at me and shook his head. “This is your last chance. You better be at least as good as your sister at this or you are out. There will be no dead weight in this family.” He said. My sister was more sympathetic; she gave me a hug and offered to help with the business side of this but warned me not to steal any of her clients.
The rest of the week momma kept refining my mannerisms, how to dress and basically how to be a lady. When Monday came around momma came in and told me it was time to start teaching me how to be a proper call girl. She said she would be back in a few minutes and left. I was wondering what was coming up when momma came in. She had Kim with her. He is a DJ at one of the local clubs and worked nights. “Kim has offered to help teach you the proper way to seduce a man.” Momma said. We started working on how to be held and kissed by a man. I must admit it was a little strange the first time he kissed me but I quickly grew to enjoy it and kiss him back passionately. Finally momma said it was time to learn how to satisfy a man with my mouth. She quickly told me how to seductively undo and take down a mans pants and underwear. I thought this would be easy but soon realized it was harder than it looked. It took about three or four times before I finally got momma’s approval on my technique. My anticipation of what was to come next grew every time I undid his pants and his cock sprang free. Momma told me to explore his penis and get used to the feel of it. I was excited the first time I touched another mans penis. I was amazed at the softness and yet hardness of it, the head glistening with precum. I leaned in and smelled the musky scent of his crotch. A drop of precum was forming at the head so I stuck out my tongue and licked it off. The strange salty taste was different but pleasing so I stuck the whole head into my mouth to get more. Kim moaned and then suddenly pulled my head off of him. Momma quickly explained about not letting my teeth get in the way, how to use my tongue and lips to suck him make it more pleasurable for him. I used these techniques on my second attempt and with more coaching from momma soon had him ready to cum. Kim grabbed the sides of my head and held me close to his crotch, I felt his penis grow and twitch in my mouth. He moaned as he filled my mouth with his seed. I swallowed as fast as I could but still a little leaked out of the corner of my mouth. When he was finished he pulled out of my mouth and laid back. With more of mommas coaching, and the taste of his cum in my mouth, I licked his now soft penis clean.
That was the first time I pleased a man with my mouth and as the week went Kim would come over every day for his free blowjobs. I sucked him many times and swallowed many loads while I perfected my techniques on him. I even grew to like the taste of his cum I drank. When Friday came around momma told me it was time to learn to please a man with the rest of my body. I knew what this meant and was a little scared but momma assured me that it would be done right and feel wonderful. Momma took me to the bathroom and explained to me the importance of keeping clean both inside and out. She produced an enema bag and showed me how to use it, and after two bags I was pronounced clean and ready. When Kim arrived we broke into the usual routine only this time momma came into the room. I was in my under things and on my hands and knees making love to Kim’s penis when I felt my panties being pulled down. “Go slow on him today, you have a lot to learn and we need him to last.” Momma said. I did as she said as she massaged and rubbed my behind. I could feel her rubbing some oil around my tight little hole when suddenly she slipped a finger in me. There was little pain as my hole opened to accept the intruder and soon it was pleasurable. I stayed that way for about an hour with Kim taking over. Soon I could take thee of his fingers with little or no pain. I was moaning with all the sensations racing through my body when momma said now it was time. Kim pulled his fingers out and got up behind me. I felt the head of his penis rubbing between my cheeks as he searched for what would now be my pussy. He found my opening and pushed forward. I groaned as there was slight pain as the head pushed through the opening and he relaxed to let me get used to the feeling. Slowly he started to push more and more into me and soon I had him all in me. He held still for a brief moment then started pumping in and out of me holding my hips to steady himself. My own penis was rock hard and I was moaning not from the pain but from the sheer pleasure of it. Kim was moaning too obviously enjoying it and I knew I wouldn’t last long. Then it happened, I started to have the biggest orgasm of my life. This must have triggered Kim because he pulled me close to him and I felt his penis twitch inside me. I swear I could feel each spasm as he unloaded his seed into me. When he finished he collapsed on top of me and we laid there for a little while with his shrinking penis still buried deep within me. Momma said that was beautiful and told me to keep him satisfied and clean his penis. As I got up and turned around to lick him clean I could feel some of his cum start dripping down the inside of my legs. Momma then reminded me to keep myself clean, both inside and out, so I went to the toilet and squatted over it. I realized the feeling of cum dripping out of me was something I could get used to and love.
Over the next few days Kim would come over for more lessons. I learned to please a man on my back, sides, knees and riding on top. I loved the feelings and there was no more pain, just sheer pleasure. Finally the day came that I would start my new profession. Momma told me that I was to meet a man at a hotel bar and be his date for the night. Remembering all I had been taught I nervously got ready for my date and went to the hotel. When I got there he was at the prescribed place and offered me a chair. After some small talk he took me to dinner and dancing. We ended up at his room where he made love to me several times. We fell asleep in each others arms. When I awoke the next morning I knew my duty and woke him up by sucking on his penis. He made love to me again and after taking another load of his seed he got dressed and ready to leave. He handed me an envelope and said he had a wonderful time and wanted to see me again when he was in town next. I cleaned my well used back pussy, got dressed and went home. Momma greeted me and asked how it was, I handed her the envelope and told her all about it. Father just listened and looked pleased as he counted the money, he finally said that it looked like I finally found a job I could handle.