How I started becoming a sissy girl.

Growing up I was some what of an adventurer when I would go out on the town. I have tried more sexual things than most people would ever dream of doing. One of my favorite things was driving to the big city which was two plus hours away. One day I wore my short white shorts and matching crop top, red and white with white tennis shoes. I went into the city for the night to check out porn shops. Dressed the way I was, I figured I would get a few Men who would take an interest in me. I looked very hot if I do say so myself. I was thin and in fairly good shape.

I needed gas so I stopped at a town on the way into the city. I could see one female behind the cash register. I felt excited being in public dressed like I was. By time I had finished filling the gas tank and went to pay for the gas, their were three females watching me from the store. She must have told her friends working in back to come and check me out.

When I entered the store the two who originally were not in sight when I pulled up, were smiling at me as the cashier took my gas money. I knew they were checking me out dressed like I was so I figured I would strike up a conversation with the cashier. I asked, how much farther to the city? About an hours drive she answered. Nothing more was said and I was starting to feeling uneasy so I left. When I turned around as I was getting into the car, I could see the two were still smiling as the cashier was saying. I am sure it was something about me and the way I was dressed.

Arriving in the city I went to one of the two adult book stores I always visited when in town. The person behind the counter barely looked at me when I entered. I looked over some of the magazines than went to the counter for some tokens for the movie booths. I spotted and older guy looking at me as I looked over the board to see what shows were showing. I gravitated towards the shemale shows which I found only one. I had no more put a token in and selected a show, when some ones cock poked through the open hole in the wall. I was not surprised at all, however I was impressed at the size of it.

I hesitated for a minute as I thought about going down on it. Than I figured I wanted some kind of sex and I knew it was going to be with a man tonight. I licked the head as it and it twitched at the touch of my tongue on it. Than I went down on it as far as I could before I started to gag on it. Than sucked it until he ejaculated into my mouth filling it. My cock was hard now and I wanted relief. I took my cock out and started beating it when I saw some one looking through the hold watching me. Funny thing, I could not ejaculate while he was there.

Next thing I knew the door opened and a guy came in with me. There I sat with my cock in my hand as he took out his cock. Suck it boy! That is all he said and I did as I was told until he also erupted in my mouth. Once I was done he zipped up and left leaving the door open. I quickly pulled up my shorts and exited the booth when a Man said, hay boy. I turned around and saw a well groomed man walking towards me. My thought was he wanted his cock sucked off also. Once he approached me he asked, Would you like to go some place more comfortable and privet? I answered, sure. He told me to follow him and we left the book store.

Once outside he introduced himself as Donald. He asked my name and I told him Billy. He asked if I would go with him back to his place? I told him I would follow him to his place, so we drove off. Arriving at his place we went inside. He must have had a lot of money because it looked like a mansion it was so big. We went into a large room with a desk and he sat down behind it. Would like a drink he asked? Sure I answered, I will take a beer. He looked at me with a smile saying, I am sorry I do not have any beer. I have hard liquor and wine, which would you prefer?  I answered nervously, wine would be good.  He pushed a button and said, Melissa bring me a glass of chardonnay and a glass of scotch to my den.

Then he said I looked very nice and I should have a seat. When I sat down the door opened and a pretty young girl entered with the drinks. I could not help but notice something was up since her maids dress was so short it only covered the very top of her panties. She delivered the wine to me first than walked to the front of the desk and handed the drink to Donald. I could see her panties had several rows of ruffles across the rear. Thank you Melissa he said as she curtseyed to him. Is there anything else sir, she asked? Yes, stay a bit.

 Billy this is Melissa my personal servant. She curtseyed as he said her name. Notice how she is dressed, and isn't she pretty? Yes, I answered taking a gulp of wine. Than he told me Melissa is a sissy, do you know what a sissy is? Yes, I answered. Are you a sissy he asked? I don't think I am I answered. Turning to Melissa, he nodded and said show him. She dropped her panties and stood reveling she had a cock.  I could not take my eyes off her, she was so feminine an girly looking other than her cock she was totally a girl. Do you like what you see Billy, he asked? Yes, she or he is very pretty I answered. Melissa is a she aren't you homey he said to her. Yes sir I am, she answered.

 

Donald asked if I had ever thought of becoming a sissy girl?  I answered, No. He told me he was sure I was already a sissy even if I didn't want to admit it. He went on to point out no man sucks cock only gay males and sissies. Are you gay he asked? I don't know I answered again. You like to suck cock don't you? Well maybe or I guess so I stammered with my reply. I know you like sucking cock because I seen you doing it in the book store. Not just once but several times and you swallowed their cum when they filled your mouth. Billy you made no attempt to spit it out. Dressed like that I can only assume you were looking for cock, am I right? Well yes I guess so I answered. Now you dress kind of gay but I believe you really a sissy who likes cock. I can make you look just as pretty as Melissa here. Have you ever cross dressed? I did not want to answer that so I sat not saying anything, I just looked down.

 

Donald went on saying he was sure I had at least worn panties before. He figured I was a sissy but just was to embarrass to admit it. He said if he had Melissa bring some pretty lingerie in here would I put it on. I answered no. Everything went silent which seemed like an hour before Donald told Melissa to take me and put me in some sexy. Melissa reached out her hand for me to take. With out saying a word I took her hand and got up. She turned to Donald and said give us twenty minutes.  I following her to another part of the house which I assumed was her room. She dressed me in pink panties with black lace trim, Pink garter tank top with black nylons. About twenty minutes later Donald came in. He said I looked very sexy dressed like a girl. You look very nice but your erection shows me how much you actually enjoy dressing like a sissy girl.

  

 



Would you be interested in becoming a beautiful sissy for me like Melissa is? Your erection is telling me you like the idea and I right?  My cock was throbbing so much it started to leak pre-cum. This did not escape Donald's attention. I see your leaking pre-cum, Donald pointed out. Melissa please take care of his erection. Melissa came over and deep throated my cock with out hesitation. While she gave me a blowjob that felt wonderful, Donald continued to ask me questions. Would you like to be a pretty sissy he asked again? I was in such a lusty, mind blowing orgasm I blurted out Yes, Yes, I would like that OH YES sir, as I shot my load into Melissa's throat. 

 

 

Donald said, very well I will have Melissa line up your training and you can start right away. I told him I could not start right away I had things I needed to deal with first. He was not happy with that but we came to an understanding. He gave me some money to pay up my bills and I had to give him my drivers license in exchange. I had one week to get my affairs in order and than I would need to be under his care after that.

 

I did what I had to do  to get all my affairs in order and while do so I was having second thoughts about what I had agreed to. When I arrived back at Donald's estate I was feeling nauseated thinking maybe I was to hasty in agreeing to this.  After all I was having an orgasm when I blurted out I agreed to it. I walked up to the door and rang the bell. Melissa answered the door and was a sexy as ever in her light pink short dress.

 

 

I was taken immanently to a bathroom and given a bath after all my hair had been removed. My assistant gave me lotion to rub all over my body to make my skin softer. than I was hit with a dab or two of perfume and given some lingerie to put on. I was escorted to Mr. Donald's den where he was sitting enjoying a glass what I am guessing was scotch. I stood in front of him and he told me he now expected me to start acting as feminine as I can. He told me he had a mistress who will be teaching me everything I needed to know to be as feminine as Melissa.

 

 

That is how I started becoming a sissy girl.