I Was Caught Crossdressing By My Boss
I got caught cross-dressed by my boss. It was a Saturday night in March (2017). I had decided I wanted to go out and have a drink at a local bar where other crossdressers go. I had gotten completely ready and was dressed very sexy, short dress garters everything. When I went to leave I realized I had forgotten and left my cell phone at my office. I decided since it was late and a Saturday night no one would be there and I would just pick it up on my way to get a drink. I arrived at the building and the parking lot was empty as I had expected. I parked and went inside to get my phone. When I got to my office I had a note on my door from Diane saying a friend of mine had called and wanted me to call him. I was not in hurry so I decided to call him. I had been talking to him for about 20 minutes when I decided to say goodbye and leave to go out. As I opened my office door to leave I nearly ran over my boss. He had come in for something too. I just froze and could not even talk. He stood back and looked at me. I tried to say something, but he told me to not talk. He just looked at me. Then he said that he could not believe what a convincing woman I was. He told me to sit down and “We need to talk”. I was totally caught and knew I had to do as he said. He started to ask if I came to the office dressed after hours often. I assured him this was just a onetime thing and I was never going to do it again. He laughed and told me he could see I shaved my body and had noticed my plucked eyebrows for quite some time. He said there were a few other guys there who had commented on how feminine I looked. I knew he was probably telling the truth as I am only 5’9″ and weigh less than 150lbs. I also do have a very girly butt that several times I have overheard the other guys kiddingly remark that they wished their wives had a butt like that. He said that maybe he could find me a job as a secretary if I wanted to show up in a dress every day. I started to get emotional and he said not to cry. He got up and got me a Kleenex from the desk and brought it to me. Then he started to wipe my eyes and say don’t cry girl. I looked at him and he leaned down and said he was going to kiss me. I did not dare say no so I just let him do it. It started to kiss me a lot and was French kissing me. I started to react to his kissing when he started to push me onto my knees and told me to suck his Cock like a good girl. I unzipped his pants and started to suck his Cock. He was calling me nasty names like Sissy, Slut, Cunt, and Whore as he held my head and used my mouth. After a few minutes he pulled me up and pushed me onto my back on top of my desk telling me to spread my legs like a good company Whore. He pushed my legs apart and pulled my panties to the side. He used his saliva to make me wet and started to finger me. Soon I was slippery and was unable to stop myself from moaning. He then pulled me to the edge of the desk, putting my legs over his shoulder and pushed his Cock inside me. He Fucking me hard calling me names and making me tell him how much I loved getting Fucked and admit to him over and over that I was a Whore. Finally he pushed hard into me and moaned loudly, filling me with a huge load of Cum. He pulled his Cock from me and got dressed. I pulled my panties back in place and was leaking his cum from my well used Pussy. He told me he would talk more about this with me on Monday and left. I did not know what to do but felt glad he was not going to out me to everyone.
On Monday I went to work and things seemed normal. Just before lunch my boss came in and told me he wanted to talk to me in his office when everyone had left after 5pm. I was nervous and it was hard to work the rest of the day. Finally when I thought everyone had left I went to his office to see what was to happen. When I knocked on his door he came and let me in. I sat down and he started by telling me he had enjoyed fucking me the other night and asked me if I had enjoyed it as well. I admitted to him I had. He asked if I liked being a girl and if I would like to get fucked more often. I admitted that I did like being a girl and yes I would like to be fucked more. He smiled and said good. I have something in the bathroom for you. He took me by the hand and walked to the ladies bathroom with me. Inside was a complete outfit from wig to heels for me to put on. He had bought complete makeup for me as well. He told me to get ready for him and come to his office after I had gotten dressed. I told him I would and he left me to get dressed for him. I was feeling Extremely girly as I put on the makeup, new lingerie, and a very nasty dress that made me look like a Whore. I finished put on the high heels and went to his office, my heels clicking on the floor as I walked. When I got to his office I knocked and said his girl was here for him. He told me to come in. I went into his office where he was waiting. He had me dance for him a little and then said he wanted to me to wait there. He left the office and shut the door. I heard him come back and he opened the door. Then I see 2 other of the guys who worked in the office walk in behind him. I did not know what to do. I was Caught and I had nowhere to hide. He said not worry that both of them knew about me and wanted to see what a Sexy Girl I was. They all started to walk around me and asked me to dance for them. I felt completely vulnerable and started to dance. They all watched and was telling me what a nasty girl I was. This only made me feel more slutty and girly. Then my boss took his Cock out and started to jack off. Soon all 3 of them were stroking their Cocks and talking dirty to me. Steve, my boss said to show the boys what a good little Whore I was and how good I could suck Cock. He motioned for me to come over and suck his Cock. I went over to him and got on my knees and started to suck his Cock in front of the other 2 guys. He told them not to be shy, that I love being a girl and would do whatever they wanted. Soon I had all 3 Cocks in front of my face and was being told to be a good Whore and suck them all. I took turns sucking them until they were all hard. Then Steve said to get on my back so they could Fuck me. I did not resist and lay on my back across his desk. He started to Fuck me as the others used my mouth. He kept asking the other 2 guys if they agreed that I needed a promotion and new job description over and over. They just kept saying he was right. Finally Steve filled me with his cum and then the other 2 guys took turns fucking me until they too had filled me with their Cum. I was completely drained and had cum leaking all over the desk top. Steve told me to make sure to be a good Whore and use my mouth to clean up the Cum. I got off the desk and could feel their cum running down the inside of my legs as it leaked out of me. I did as he said and licked up the mess on top of his desk. When I had finished I asked him if I was done and if I could get dressed. He looked at me and asked me if I wanted to know about my new promotion and the raise in pay I was going to get. I was more than curious and told him yes. Steve told me that they had agreed that the company needed a full time Whore that could be used by the guys in the office and also would take care of keeping other potential clients who may want to fuck me happy as well. He said I would get a nice raise on my check and that I had no choice in the matter so I had might as well agree. I looked at them and thought about it for a moment. I knew I liked the way I had just been used and thought about the money. I agreed and asked if there were anything else he wanted me to do. He then told me I was to start taking female hormones so my breasts would develop. I had been wanting to do this any way so I agreed. He then told me that within the next year he was going to pay to have me receive breast implants, and any plastic surgery necessary to completely feminize me. I agreed and also told him that if after a year should want me to have a sex change I would also agree to that. He told me he would have a legal contract giving him the right to do these things on my desk in the morning and if I still agreed I was to show up dressed as a girl and sign it. On Tuesday morning I got ready for work as Sherry and went to the office. Steve had told everyone of my lifestyle and that they were to refer to me as Sherry and to treat me like the girl I had chosen to be. Everyone was supportive and I have had no problems. The hormones are starting to work and Steve has paid for me to have a private trainer at Curves to help feminize me. I still am used by all 3 of them at work and have also been on several dates with men Steve has lined for his new company Whore. He has also made sure I have been paid well for my extra hours work. I love my job and I am so happy I was Caught.
Sherry
Just a little update to my readers.
Today one of the girls at the office had Steve ad her to the list of people that I am to service. He had me eat her Pussy and she also used a strap on to Fuck me while Steve watched and cheered her on. Being the Good Whore I Am I made sure she was satisfied several times. She said she is sure that she will be using my mouth every day. She said her husband does not do oral.
Sherry
Tags: sissy