I had been dressing in private for years and never have tried to be passable, as I get my thrill out of being all man to the world, yet so girly just underneath what everyone sees. I decided that I wanted a thrill, so I went to the local Target, with my leopard panties, matching leopard camisole, black garter belt and with stockings on, under my man clothes. I picked out a pair of Dockers and went to the fitting room, stripped down to those things and just stood there looking at myself in the mirror. All the while I knew someone might look through the crack in the door, under the door, or push it open, not knowing someone was in there. As I stood there, I felt so vulnerable and naughty, loving every minute of it. After a minute or two, I heard someone clear their throat and turned to see an eyeball looking through the crack in the door. As soon as I saw it, it was gone, so I quickly put on my man clothes and hurried out of the fitting room.
Now I was scared to death, yet also thrilled, as everyone I passed in the store could be the one who saw me. I continued to look through the mens clothing, but soon was approached by a security guard. I thought this was it, that I had been reported and was now in big trouble. The guard asked me if I would please come with him to his office, as he needed to discuss something with me. I agreed, as I did not want to make a scene and have him out me there in the store, if he knew what had happened. Once in his office, he shut the door and locked it, telling me that he had been in the fitting room and saw who I was just below the surface. I did not know what to say, but asked him if I had broken any laws. He just smiled and told me no, but if I did not want him to tell everyone in the store what I was wearing, I would do as told.
Well, I must say I was both thrilled and scared to death now, as I had no idea what he wanted and I had not been with a man anally yet. He told me to strip down, which I did, then he just stood there looking at me for what seemed like an eternity. I was so uncomfortable, but what could I do at that point? He then started to unbutton his pants, all the while with me standing there. When he had them down around his knees, he sat in his chair and told me to come show him what a girly bitch I was. I told him I had not done this before, which was a bit of a lie, as I had sucked a few cocks. I came around, got down on my knees and started to lick the head, which was pretty big and getting harder by the lick. He started to moan and tell me what a whore I was, which turned me on more. I eventually started to lick up and down the shaft, making his cock jump and twitch even more. I then slid as much as I could fit into my mouth and started going up and down the shaft. He grabbed the back of my head and started to hold it in place as he fucked my mouth, calling me a fucking sissy boy the whole time.
This went on for about 5 minutes and I thought he was about to cum and this would be over, but I was wrong. Just then he told me to get up and lean over the desk. I told him that I had never been fucked before, which made him laugh and tell me that he could care less about that, as I would not be able to say that anymore when he was done with me. Feeling I had no choice I did as told, then he grabbed my hands and tied them to two of the legs of the desk, then tied my feet to two of the other legs. There I was all dressed girly, tied to a desk in the security guards office. I felt him come up behind me and start to rub his ROCK HARD cock against my panties, telling me to beg him to fuck me, which I did. I felt his fingers go inside the elastic of my panties and slowly pull them down, just to my knees, to make me feel really cheap. I then heard him open up his desk drawer, but could not see what he was doing. I then felt a moist finger start to go in me, which had lube on it, so I was somewhat relieved. After a few minutes of him finger fucking me, I heard him ask if I was ready to become a real woman, which I moaned yes to, making him laugh at me.
I then felt the head of his cock start to pressure against my willing manpussy, but it was having a hard time getting in. This did not stop him as he kept pushing, until the pain was getting a bit bad, which I told him, but he just laughed and pushed harder. All of a sudden I felt the head pop in and I let out a squeal, making him laugh even harder, as he bent over and whispered in my ear that I was now a woman and his bitch. He then slowly started to push it all the way in, until I felt his balls hit my ass cheeks. After holding it there a few moments, he slowly started to fuck me slowly, picking up steam with each thrust, until he was pounding me and making the desk move with each thrust. After what seemed like forever, I heard him tell me he was going to cum and I was going to take it. With that he grabbed my ass cheeks, pushed one last time and let out a huge moan, as I felt a warm sensation deep in my manpussy. He held it there for a minute or two, then pulled out.
He untied me, told me to get dressed, without letting me clean up, and told me that I was not to mention this to anyone, or he would show the pictures that he had taken, which I did not know about. I then left, with his seed dripping into my panties as I walked to my car, got in and rode home.
This is how I became a mans sissy bitch and now I want more.
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