My new job

I had just started a new job as personal secretary to an executive in a holding company, and after my first day I decided to celebrate and bought myself a drink in a bar around the corner from where I was working. The place was quiet and small, on the television behind the bar was some fashion show for men’s clothing. I sat and stared at the TV and drank my beer all by myself, when a guy sat beside me. We starts chatting about this and that nothing too deep when he asked what I thought about one of the outfits on the TV. I looked up and it was a guy wearing a dress. Not knowing the man I commented that it was different then down the rest of my beer. As I sat the bottle down and was getting ready to go another beer soon arrived. One is normally my limit and it was today since I hadn’t gotten paid and had very little money.
‘Oh I didn’t order that’ I told the bartender but the men said he bought it for me. I thanked him and started to drink it. ‘What do you think of that’ he asked me once again nodding towards the TV again. I looked up and saw a guy wearing a spanking dress with stockings walking the cat walk. ‘Well that’s almost a turn on’ I said. The man introduced himself as Greg Shane and we moved to a small table near the back of the bar. The table was against the wall and we both sat on the padded bench. Greg was honest and told me he was gay. When he asked me if it bother him I said no because it didn’t. As the conversation continued somehow he asked me if I had ever had sex with a man and I told him the truth that I have and enjoyed it very much, but added that it was twenty years ago as well.
After my fourth beer I told Greg I was feeling the effects of the beer and had to go home. I thought that would be the end of ever meeting Greg. The next day I showed up at work and found out that my boss who recently hired me was just let go. Personnel came to see me and said I was reassigned up stairs as personal assistant to one of the Vice Presidents and on a side note was told that he hates everyone that was the reason there was an opening. I packed up my few things and took the elevator up to the top floor where the personnel lady walked me to my private office. She was going to introduce me to my new boss but he was out at the moment. I was to make myself at home until he arrives.
After waiting for over three hours lunch was at hand and I called the lady in personnel and ask to take lunch. I sat quietly in the cafeteria by myself. When I returned to my office Greg sat in my chair. ‘Hey how are you?’ I said with a smile. Greg looked up over his glasses and smiled back. We chatted for a bit when I asked what he was doing there ‘I’m your new boss silly’ he replied. He had me follow him into his office and asked me to take a few notes for him. He wanted me to sit next to him on the couch so he could see I was taking notes properly. After half an hour his hand was on my leg, squeezing my thigh and getting closer to my crotch.
‘You know that I am gay and I know you have had sex with other men so let’s make this a mutual benefit for both of us and be good to me and I will be good to you’ he said gently rubbing his hand across my crotch that was now hardening before his eyes. He leaned over and kissed me and gave my crotch a good hard squeeze. ‘No joking but you will have to work late tonight’ he said standing and walking back to his desk. ‘I have strict rules of what you can and cannot do, and what you are to wear and not to wear. If you really want this job you will do whatever I ask of you OK?’ needing the job I agreed.
As I finished typing up Greg’s last notes I saw that everyone had already left when Greg sat on the corner of my desk. We are going out to a place I know, I think you are going to learn to love it.’ Soon after that we were in a cab heading to this place he knew. We arrived and Greg paid the driver and put his arm around my waist and guided me into this seedy bar. A place where all the men wore leather, kissed openly and some men sat on the floor with collars around their necks and the leash hanging to the side. Greg led me to the back or the place and we stood facing the wall with our beer on a shelf. Greg spent no time making his move on me. His hand was grasping my ass and his fingers rubbed across my balls all though my pants.
‘We have to go over some ground rules’ he started. ‘At work you will call me Mr. Shane. If I call you to come into my office you will come immediately. If I tell you to suck my cock you will suck my cock and if I want to fuck your ass I will’ he stopped and waited for an answer. I was so horny at that moment I agreed. ‘You will wear panties and stockings under your pants from now on. As I get to know you I will put more on your plate and you will climb the latter in the company in no time’ he said turning me towards him and undoing my pants. He held my pants open and looked at my underwear. ‘Open your underwear and show me your cock’ he ordered. I reached down and pulled my underwear open for him to see. ‘Good now look at my cock’ I undid his pants and he wasn’t wearing any underwear. His cock was hard average size and circumcised, just by looking at it I was turned on.
The next day I was working away when he asked me into his office and asked to see my underwear. I undid my pants and showed him I was wearing panties and stockings as requested. He ordered me under the desk and then I gave him a blow job and loved every inch of it. He made me swallow his load.
After a few months this went on and now he wanted me back at his place this evening. He told me he had a surprise for me. I arrived at his place for ten as ordered; I walked in as he opened the door. He was wearing a leather outfit that showed off his magnificent cock. We went up stairs and he had me dress totally as a woman, hair makeup the whole nine yards, I became incredibly horny and aroused. He had me walk around in stilettos and then down the stairs where he made love to me making me cum three times and swallow his two loads.
The next day at work he called me into his office, sitting on his desk was my personnel file and the lady from personnel. ‘I just wanted you to know that I have talk to personnel and you can go ahead with the gender change’ he said with a slight smile and a wink towards me. Speechless I smiled and thanked him. After the lady left I walked back into his office, he threw up his hand and stopped me from talking. ‘From now on you will come to work dressed totally as a woman, you will walk and talk like a woman from now on. Your name will be Contessa, I have an appointment for you to get hair extensions and the company pays for it. No talking back to work’ he said and motioned with his hand to leave.
That night much to my surprise I went and got the extensions was fitted with a whole new wardrobe and even a doctor looked me over and had all my body hair removed. I felt naked but sexy as well.
The next morning I arrived in a short mini dress long hair and hornier than I have ever been. Men now stopped and checked me out; women stopped and asked me questions about makeup and clothing. Greg called me into his office where he for the first time had me bent over his desk as he fucked my ass as deep as he could.