Crystal's StorySite


My Job as a Crossdresser

by Beata Bockman


I have been looking for a part time job that I could dress at. I was for the most part unsuccessful but then I met Bill. Bill was tall attractive and married. We dated off and on for a while behind his wife's back. One day when we were on, Bill mentioned that they were having a hard time finding a girl to work on Saturdays.

"I am looking for a job" I said.

Bill said, "Emily, you know that I don't mix business with pleasure"

"Aw come on what harm could there be."

Bill thought about it for a bit and said, "Sure why not, could be good for the guys."

Bill then told me about the job. It would be on Saturdays, I would be answering the phones and doing some typing and some filing, I would have a few special projects of my own. I would be expected to be dressed all the time. I asked about the special projects.

Bill said, "We are having a bit of a morale problem and I am trying to get the guys to come in on Saturdays to get the work done. Do you have any ideas?"

A devilish grin came over my face. "Are there any limits to my morale program".

"I'll listen to anything. Pay would be fifteen dollars and hour and bonuses would be dependent on how many hours I could get the guys to work on Saturday".

I said, "Sounds good when do I start?"

"Can you start this Saturday?" asked Bill.


It was Saturday morning. I shaved my legs and laid out my best business attire. I decided to wear my black suit that had a short skirt with black pantyhose and pumps. My makeup was perfect and I applied my fake nails and a coat of red nail polish, I put on my pantyhose and a black bra to hold my breast forms. I then put on my suit and pumps, I looked and felt great.


I got in my car and drove to Bill's office. This was the first time that I had ever gone out dressed in daylight. I did not realize this till I got halfway to the office. I wondered how I would pass. I decided that if I worried about it I would never pass. When I arrived at the office park where Bill's business was, I saw that there was only a couple of cars in the lot. I parked my car near the door got out and walked in. Bill was expecting me and greeted me at the door. First Bill introduced me as Emily to the crew. There were three guys that showed up and Bill explained that two more did not come in today. They all seemed nice even if they could not keep their eyes off my breasts or legs. Bill then showed me where everything was, including the ladies room and my own cubical near Bill's office and next to his secretary. She only worked during the week so no other women were there. I was getting settled in when Bill asked if he could see me in his office. I followed him back. Bill outlined what he needed me to do today and then we talked about my special assignment.

"Emily, do you have any ideas for improving morale?"

I said, "I was still trying to find out what was going on here."

"Well if it involves your legs or breasts then that would be a great start."

I laughed but Bill then said "I am serious, I think these guys need to get laid."

"I see where this is going," I said.

"Is this a problem?' asked Bill.

"I thought you wanted to get some more work done."

"Well we will need to put up some limits but its up to you. Get a proposal on my desk by lunch." said Bill.

"Ok Boss" I said and I left to get my assignments done.


I first worked on the filing and then the typing. While I was working a few of the guys came by for some small talk. Seems that Bill had told them that I was a crossdresser and that seemed to fascinate them. That's when I had an idea. I went back to my cube and started typing it up. At about eleven I went back to Bill's office to outline my plan.

I said, "If you need the guys to come in on Saturday then why don't we have some incentive to "cum" in."

Bill agreed with my plan and said that we would try it out next Saturday. He figured that the ones that came in today would tell the others and then all five of the crew would be in next Saturday to check out the new girl. I went back to my desk and I finished the rest of the work. By four o'clock everybody was gone except for Bill and myself. I went back to Bill's office. Bill said that he really appreciated what I was doing for him and that he thought that all the guys were looking forward to coming in next Saturday. Bill and I kissed and then he said, "see you next Saturday" and gave me a pat on the butt.

I drove home with my panties wet with anticipation for what was to happen next weekend.


The following Saturday I got ready. I put on a black garter belt and stockings, over that I put on a leopard print thong and then my black bra over my glued on breasts. Next I put on a short black skirt and a white shirt with shear sleeves. Then I put on a black double-breasted jacket to complete the businesswoman part. I wore my black open toe pumps that showed off my red toenails and had a four inch heel. I looked in the mirror and boy did I look great. I quickly got in my car and drove to the office. Bill and I had decided that the guys needed to get some work done in the morning but the afternoon was mine to "improve morale"


In the morning, work was uneventful, Bill had the usual filing and typing for me to do. During a smoke break one of the guys named Tom came by for some small talk. I think that he liked me. About noon I answered the door for a cute guy that brought lunch. As I paid him I noticed that he could not keep his eyes off of me. Too bad that he does not work here I thought.


After lunch we continued working. Tom again came over for some office small talk. We exchanged pleasantries then I decided to put my plan into action. I got up and pulled him close to me and gave him a kiss. To my pleasant surprise Tom kissed me back. Things quickly progressed to where I had pulled down his pants and sat him down on the desk. I then proceeded to give him a blow job. As Tom was about to cum I heard noises behind me, I figured that it was one of the other guys. Tom shot his load into my mouth. I turned around saw that the other four guys were standing there. Swallowing Tom's cum, I took off my suit jacket and skirt, I said, "Who's next?"

I then said to Tom "since you got the first blow job you get to fuck me first."

Shawn was next for a blow job. I kissed him and undid his pants. While on my knees I started licking Shawn's cock. Tom got behind me and pulled down my thong. While blowing Shawn I fumbled for my purse, finding a condom and a tube of lubricant I handed them to Tom. I continued working on Shawn's dick and Tom started to grease my ass. While Tom worked his rod into me I continued to work on Shawn's cock. Before I knew it I was on all fours giving a blow job while getting fucked in the ass. I had never been with more than one guy at a time so this was a totally new experience for me. It felt great to be the center of all this attention. One guy was fucking me while I was blowing another with three more watching. When the last guy finished fucking me we all noticed that Bill was standing there. Some of the guys looked at Bill with a look of terror in their eyes. I just had a devilish grin on my face.

Bill said, "don't worry she is part of the new incentive program. On Saturdays you will turn in your progress reports to Emily. She will go through them with me. If you are meeting the goals that I laid out for you, Emily will have sex with you. If not then you will spend Saturday afternoon working on your project while the ones that are getting their work done will be having sex. None of this can be mentioned to anyone outside of this group. If you talk then you will not be able to participate in this plan. So what do you think of the new incentive program?" All quickly agreed that it was the best plan that they ever had.


Now my Saturdays consists of spending the morning reviewing the progress reports with Bill and then having sex with five guys in the afternoon. I wear very sexy clothing and even some platform shoes and leather cat suits. The guys buy me clothing and jewelry trying to gain favorable treatment but it is not necessary. All of them are performing above plan. This will only last a couple of weeks then maybe we will have to come up with something else, but that is part two...




2004 by Beata Bockman. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.