I worked at a big advertising company in New York City. I was not married do to my crossdressing. My crossdressing was one of the most important things in my life. I would come home from work and get dresses in my skirts or dresses. I would cook, clean, have sex with guy and go out and have fun.
I stared to dress when I was an early teen. I would go into my mom’s or sister’s room and steal there clothes and put them on when they were gone. Started out wearing panties and bras, then after some time moved to wearing skirts and dresses. After some time at wearing there clothes I was hooked on crossdressing. At times I would even go to school wearing my sister’s panties. One time I even went to my Halloween dace with a girl I know. What a great night. I had on a short skirt, low cut top and a lot of make up to make me look like a hooker.
I was one of the big wigs in the company. I would have to go to the customer to sell them your advertising plans for there company. I would have to go all over the world. That would give me lots of time to dress when I was on the road. I would bring my clothes with me and dress in my room. If I went to a city I have been to before I would go out. I would find out were to go on the internet. I would to gay bars for a few drink and look around for nice gays to have fun with.
The first time having sex with a guy dressed was on a trip. This guy came to me at a bar and told me how good I looked and he wanted to take me home and have fun with me. I know I wanted to have sex as Heidi that night, so I went home with him. When I stepped though the door I turned around and wasted no time and quickly knelt in front of him and started unbuckling his belt and unbuttoning his jeans. I finally pulled his cock out and it was the first time I had a close and personal look at someone else's cock. It was long, smooth, and not too thick. As if by instinct I opened my mouth, stuck my tongue out and started licking his cock like a lollipop. It was such a weird sensation and feel in my mouth.
I was so turned on knowing that I was finally doing what a girl does. I started really getting into it and started bobbing my head up and down his cock and slurping at it as if I was starving. I licked and sucked and jerked him and eventually I started to taste a familiar taste, it was his precum. I had tasted my own precum before and knew what it tasted like. Being so turned on and this guy being so cute and nice I was determined to have him be my first fuck.
In between mouthfuls I asked him if he wanted to fuck me. And he nodded yes with eagerness. I got up, danced over to my purse and grabbed a condom. I went back on my knees and rolled the condom on his cock.
After making sure the condom was on he lubed his cock with my mouth. He turned me around to put some lube around and inside of my virgin asshole with his fingers sliding in and out. When done I knelt on my hands and knees on the over the couch and lifted my ass up in the air. He lifted up my skirt and moved my black thong aside and started slowly easing himself in. It took a little bit of time but even that was turning me on. He was rubbing the tip of his cock up and down my hole.
Then it happened. I felt his nice mushroom shaped tip slowly parting my man pussy. With a small push his head was in. I've practiced with smaller dildos before, but never the real thing. I was so excited but I knew I needed to breathe and relax. As soon as his head was in, she started slowly pushing his full length into me. He was so gentle, telling me to relax and stroking my back. He had such a nice cock for my first time. It wasn't too thick and it was nice and long. He slowly glided into my ass. And when I felt his full length into me as his pelvis bumped into my man pussy, I finally felt like a woman!! What a great lover he was.
I was getting bolder in dressing. I was even starting wear panties of all kind to work. When the other workers were gone and I still had work to be done I would lock my door and change in to a skirt and top. At times when I know no one was around I would leave work and drive home dressed as Heidi. This went on for mouths. There were a few times the cleaning crews caught me walking out my office and did not say anything. I even looked back and a few guys were looking at me. The times I would drive home I would apply my make-up and put on my wig so I looked like a lady that was working late.
There was this one time I was carrying two big boxes home. I most have looked like I was having problems walking with them in my heels because one of the cleaners asked if I needed help carrying out the boxes. I would wear 2 to 3 inch heels from work. When he started to walk away I know I had to thank him the right way. I called him back to the car. I told him I want to thank him for helping out. I got close to him and reached down to touch his cock and found it to be hard. He jumped from my touch and tock in a deep breath. I know he wanted me, so I push him in my car.
I knelt down and unzipped his paints and what jumped out at me was a big hard cock. I licked his mushroom head just like I did the first time I ever had a cock in my mouth. I started to bobbing up and down on his nice hard cock. After a few minutes I know he was going to cum because of all the precum that was pumping out and the hardness of his cock. It just took two more times going down and gaging myself for him to cum. When he finished filling my mouth and throat I zippered him up and thanked him for helping me with the boxes and the snack.
It was Sunday afternoon and I was done with the work I did over the weekend. Well I was dressed like I was all the time on the weekends so I was going to go back to the office and drop off the work. My boss Tim called me as I was steeping out the door. He told me that he wanted me at work early Monday because we had a big job coming up and we needed to start on it and he was leaving the office. I got to the office about twenty minutes later and looked around to see if I could see his car or any other co-workers car’s, finding no cars I went in.
I was in my office about ten minutes when my office door came crash in and it was Tim. Yelling what the hell are you doing in here and who are you? I did not know what to do so I just stood there being nerves. Well Tim was a male whore anyhow. Over the years his secretary’s would quit or just leave. He would hit on them and ask them out on dates. He was not getting any at home from his wife, so he would try to get some from the girls in the office.
When I did not say anything he walked up to me and spun me around to see my face. He jumped back after seeing my face. What the fuck john why are you dressed as a girl. Well I could not lie now to Tim. I am a crossdresser and I like to wear female clothing on the weekend and at night. John just gawked and looked me up and down me for a few minutes. Well John if I did not know you, I would think you where a real female. You know I do not get any sex at home and I am horny as hell. With that said Tim walked over to me and put his hand on my shoulder and pushed me down to my knees.
He told me if I wanted to keep my job with the firm I would do what I was told. Knowing how the job market was for the advertising world and the money I was making I would have to do what he told me. In the back of my mind I know I was going to be fucked hard and would be sucking him today looking straight at his crotch. Tim told me to undo his paints and pull out his cock and suck it.
I did what I was told and unzipped his paints and Tim’s cock just fell out. What fell out shocked me to see how big Tim was. He had a nine inch long and around 3 inch wide dick. Back in my mind I know it was going to hurt me if he wanted to fuck my pussy. I opened my mouth and started to lick his mushroom head and shaft. His cock being so big stretched my mouth and gagged me when I started to go down on him. Tim grabbed the back of my head and toke control on how I was sucking him. He would push his cock deep in my mouth and make me gage and make me breathless at times. He would pull my head back at times and told me I was a slut then slap me in the face with his cock.
What was coming next I di d not want. Knowing what with my mouth and making my jaw so sore I did not what that to be my pussy. He dragged me over to me desk and told me to bend over the desk. I could not help but do it because he pushed me face down. When he forced me down he lifted my skirt to show off my raffle panties that I had on then gave a hard slapped across my ass. I will love fucking you Heidi and you are going to be a great slut. He ripped my panties off my ass and told me his dirty slut do not wear any panties and just thongs. Then with another slap, that is what I will wear from there on.
With a few spits on my pussy hole Tim slowly started to move close with his monster cock. I know at this point he was not going to use any lube. I could feel his mushroom head entering me and with a forceful push he was in. It hurt so much as I cried out stop. It felt like it did when i had sex for the first time. He did not stop till I felt his balls against my body. He bent down to my ear and whispered to me, you are now my slut now, how dose it feel having me inside of you. With tears running down my face I had to say good. I was bent over the desk that felt for hours till he flipped me over and started over with me on my back with my legs over his shoulders. In back in my mind I was asking, how long can he last?
A few more minutes of getting my pussy ponded, I know he was going to cum soon. His cock was swelling with cum inside of me and his breath was getting heavier. He pulled out and placed his cum fill cock next to my face and told me to open. Next thing I felt was a warm and gluey cum falling on my face and in my mouth. I think he squirted galleons of cum on my face. When he was done he forced fed me his cum by sliding his cock over my face. As he was doing this he said that I was a good slut and to swallow every last drop.
Well Heidi as you now I need a new secretary and one that knows advertising, I think I just found her. You will take the next week off and come in next Monday as Heidi. Also you will go and get silicone breast put it from a doctor I know. You will come in to my office when ever I need you and do what ever I say or I will tell everyone and you will loose your job. The next week I cam in to the office in a skirt low cut top to show off my new 38 D breast that Tim told the doctor to use. That Monday I did not leave his office the whole day. He used my manpussy and mouth as a cum bucket. It has been over a year now in my new role in the firm.
Every week he has me in his office two or three times and uses me as a slut. In the same year I had to go out and service a few customers. They would ask Tim if he know anyone that he could send to escort them around for a few days. I was it, so off I went for a weekend of fucking and sucking guys from around the world. Some of them had small cocks and some had big cocks. I have not found as big as Tim. We signed a lot of new customers with we going out and being a slut.
The last time I came back from being an escort Tim told me his wife is leaving and I am going to move in with him. Dam I can not handle his cock every day. As it is I can not sit down for hour after he uses me now. I am going to be used every dam night I better like to stand around.