Joanna Tranny Prostitute
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She was hanging outside my place of business all day long looking like a hooker but afraid to solicit money for sex from a stranger. Obviously she was new at it. I had seen a few prostitutes on my corner over the years but she was just a kid.
Finally I walked outside and asked her if she wanted something to eat and drink. She said yes and I invited her inside. I asked her what she liked to eat and then I ordered a pizza for us to share and a couple of sodas.
We had twenty minutes to talk. She was a runaway from Ohio, she was just sixteen, and she was scared and alone.
I asked her why she had left her home and discovered that it was her mother’s latest live in boyfriend. He raped her and her mother refused to believe her side of the story. After that he could rape her as often as he wanted too and get away with it. She took it for a month and then she left home.
Her name was Debbie and she was pretty. She was wearing very tight pink shorts that exposed as much of her ass as they covered. She had a tiny bikini top on and huge earrings. She had on too much makeup and too much cheap perfume.
I made her an offer to work for me and in exchange she could sleep in my guest bedroom and eat with me. As to pocket money I offered her a hundred dollars for a fifty-hour week. I work five eight-hour days during the week and a ten-hour day on Saturday. Debbie said that she would try it out for a while.
When I drove her home I asked to see what clothing she had with her. Everything was slutty looking. So I took her shopping and bought her five outfits that she could wear in my store. We compromised on no bras and thong panties. Then we compromised on button up shirts and miniskirts. She could also leave the top three buttons undone.
That night she went into her own room to sleep and I heard the door lock and a chair being placed under the doorknob for added protection.
In the morning I knocked on her door and started to fix breakfast. Debbie came down in her new outfit and she looked pretty and she looked sexy. She had left four buttons undone and I could just barely see a hint of breast flesh. When she reached for her plate I saw one of her tiny nipples. It was pink, hard, and surrounded by a tiny pink areola. When I told her that I could see her nipple she smiled and said that she didn’t care.
That day at work she made it a point to show me a nipple once in a while or her panties when she bent over. Debbie was quite a little tease. She would giggle whenever I would get hard.
She would be the perfect little angel whenever a customer would come in. She was respectful and very courteous to both the men and to the ladies. I actually think that she helped make a sale to one man that was looking for a nice gift for his wife. She did not push the higher priced item she just said what was pretty to her. So he bought it for his wife.
After he left and I told her that she had done a good job she asked if she could unbutton another button on her blouse. I had to laugh and give my approval wondering what would happen when she ran out of buttons.
Just before closing time a well off woman came in. Debbie offered to help her and the woman looked her over pretty good. I smiled when the woman kept looking down Debbie’s blouse. I was about to take her aside and say something when the woman asked Debbie to show her the restroom. Debbie said that it was for employees only however if she didn’t mind going through the backroom to get to it she could use it. The lady said that she would follow her. I looked at the clock and noted the time. In a couple of minutes I locked the front door and put the closed sign in the window.
I waited a couple of minutes more before heading back toward the bathroom. As I approached I heard them talking.
Debbie said, “Did I do good?”
The woman replied, “Oh yes, you did great. That was a terrific orgasm, one of the best that I have had. Will I get you in trouble with your boss?”
Debbie replied, “Not if you buy something expensive on your way out.”
I slipped back to the sales floor and waited for their return.
Debbie showed the lady a selection of our best watches and helped her pick out an expensive one. The lady paid for it with her credit card. I asked to see her driver’s license too so that I could compare the signatures. Actually I confirmed her name, age, and birth date too. I wanted to know the woman that just had sex with my employee.
I placed the watch in a nice case and unlocked the door so she could leave. When she was gone Debbie told me what they had done in the bathroom or more precisely what she had done to the lady. Then she asked me if I would buy her some thinner shirts to wear, maybe ones that she could tie under her breasts. She mentioned micro miniskirts too and maybe no panties. I just smiled.
However, on the way home I let her pick out five sets of very sexy clothing to wear at work.
That night I did not hear her lock her bedroom door or shove a chair under the knob. Maybe she was starting to trust me.
The next morning at breakfast she could not stop talking about how good that woman’s pussy had tasted in the bathroom. I could not help but stare at her. All she was wearing was a tiny little skirt and the bikini top that I had first seen her in. I was pretty sure that she wasn’t wearing any panties but to prove it she opened up her legs for me. I though that all girls shaved their pussy but Debbie didn’t. It was nice and hairy like it should be.
That day at work, things were a little slow but every now and then some man would see Debbie through the windows and come in. She knew what they really wanted to look at, but that didn’t stop her from trying to sell them a gift for their wives. She would bring a tray out for them to look at and then Debbie would untie her bikini top and retie it again to make sure it was on tight. I had to smile knowing what she was doing. I must admit that she made a sale each time.
I had sent her down the street for lunch when the rich business lady came in looking for my young salesgirl. I explained that she would be right back and the woman told me that rather than keep buying expensive jewelry that she didn’t need that it would be easier to just rent Debbie for fifteen minutes and offered me a hundred dollars. When she put the money in my hand I stopped to think about it and at that moment Debbie walked in and said hello to the lady. I told Debbie that the woman wanted fifteen minutes with her in the backroom. She smiled and too her back.
Sure enough fifteen minutes later they returned. I watched as the lady kissed Debbie, squeezed her butt, and told her that she would see her on Monday. After the lady left I gave Debbie the money. She was surprised that the lady had paid for sex and even more surprised that I had prostituted her out. She didn’t mind at all she was just surprised that I would do such a thing. I was too.
After work on our way home Debbie kept telling me how horny she was. I watched as she fingered herself as I drove. She took a bath right away then came down in one of her new almost transparent shirts and nothing else at all. There was one button attached at her belly button but it didn’t cover much.
Debbie told me that she was still horny, that she had masturbated throughout her entire bath but that she didn’t scratch the itch between her legs. Then Debbie asked me to make love to her. She had been raped and she had been fucked but no one had ever made love to her before. She wanted me to be her first.
She had kept me sexually excited for a few days so I was also about ready to pop. Anyway of course my answer was, yes. What sixty-two-year-old would pass up a sexy willing sixteen-year-old anyway?
I took her to my bedroom where I had a king-size waterbed. She was impressed and bounced around on it showing me her pussy, her ass, and usually one of her tiny perky breasts. Her one button came undone and that shirt were sailing across the room leaving her naked, excited, and still bouncing around on my bed as if it were a trampoline.
When I was naked Debbie whistled and said, “Not bad for an old dude.”
I assumed it to be a compliment even though I wasn’t too sure about the old dude part. I had gray hair on my chest, a slightly rounded belly, and at the moment only a half-hard penis. I remember the days when I would have been hard just thinking about having sex with a woman and here I was with a naked woman and only half-hard.
Debbie crawled over to the edge, grabbed my hand, and pulled me down with her. She didn’t seem to know where to start so I hugged her to my chest and kissed her softly as I ran my fingers through her hair. Apparently she was not used to kissing but she sure took to it quickly enough. I rubbed my hand down her back to her butt cheeks and caressed them as we kissed. When I pulled my hand closer and started up her body toward her breasts I found out that Debbie was quite ticklish. She squirmed in a cute little girl way and rubbed her hip and thigh against my cock causing it to rise to attention finally. I moved down to kiss her breasts, squeeze them slightly, and to suck on her nipples. Debbie was a full A-cup and growing into a possible B-cup at that point. I started fingering her pussy and found that it was wet and wonderful. She liked it when I touched her clit. She really liked it when I sucked on her clit and ran my tongue all over it. Soon I was poking my tongue into her hole and giving her an orgasm.
Debbie cried out, “Now I know why that lady likes me to lick her pussy. It’s wonderful. Keep doing it, your fifteen minutes isn’t up yet.”
I laughed and told her that I was only doing it because I wanted too and that I would stop when I wanted to too. However, knowing how much she liked it made me stay there longer than I would have. Finally I had to get some satisfaction out of it myself so I slipped my cock into her well used pussy and found it to be very tight, almost virgin like.
Debbie cried out, “Oh my God, you’re so big. My mother’s boyfriend must have had a tiny dick.”
I was only average at about six inches but to her I was Superman. I must admit that my ego got a boost. We were both enjoying our first time together. She told me that she never knew that sex could be so nice. She said that she wanted me to make love to her ever day. Then she said that she wanted to sleep in my bed too. I had no objections to any of it.
Debbie became very important to me, both in my personal life and in my business. She continued to prove to me that sex sells. It sells jewelry and it sells itself. She never slept with any of the men but she continued to take care of her ‘lady’ friend once or twice a week. That ‘sex’ money went into a special bank account just for college and it built up nicely.
My lawyer was able to get a copy of Debbie’s birth certificate and all of her school reports. He also get her emancipated to be an adult at sixteen. From there I had her attend high school, graduate, and then go on to college. She majored in business and took over the store when I finally retired at seventy. To this very day Debbie sleeps in my bed.
The End
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