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Crossdressing in the Office

Crossdressing in the Office

My name is Daniel and I have been crossdressing for as long as I can remember now.  It started with me wearing my mom’s dresses and now I have a wardrobe full of women’s clothing. I live all by myself in a tiny apartment and I dress up quite often. I have also went out in public few times  and it was amazing. But I am still not very confident about crossdressing in public since I live in a very busy neighborhood and there are always people passing by.



I have been working for a Software development firm since the last four months.  There are around 20 employees in our office and I have my own little private space. Since dressing up at home had somehow lost its charm for me, I kept having this urge to dress up at my office. I knew of the risk of being humiliated if I was caught crossdressing at work. I had a good position at work and I didn’t want to lose that either. So I kept trying to not think about it but the urge kept getting stronger. 

It is quite usual for staffs in our office to work till late night because there are deadlines for different projects coming and going. So I decided to plan for the right moment to stay back at the office while everyone else have left and pretend to be working. Usually, the one who leaves the office last has to lock the place up and drop the key at the security center near our office. 

I planned to finally crossdress at work on a Friday evening as my office had meet most of the deadlines and all the staffs had less work to deliver. I cross-checked everything to make sure things would go according to my plan.

I had this intense desire to dress up as a hot secretary. So when the day finally came,  I packed a lovely printed blouse, padded bra and panties, black miniskirt, my favorite hair wig, sheer black pantyhose and high heels. I also packed a small makeup kit, some makeup removal tissues, a lovely bracelet and clip-on ear rings as I really wanted to dress properly. I was really excited leaving for work that day. 



When I reached the office, I went straight to my office and put the bag in my cabinet and locked it. I was having such a rush just thinking I was really going to be dressing up in my office. I simply couldn’t wait to dress up and enjoy my time.

I had already mentioned to few of my co-workers that I had to stay a little late to finished some work. They brought it and I was relieved that things were going as planned.  After 5 pm , most of my colleagues had already left and others were finishing up. It felt like an eternity waiting for the rest of my colleagues to leave. Our boss was out of town that week and that made it quite perfect for me as well.

Finally, after all the people had left, I waited for some minutes just to make sure nobody was hanging around. Then I went to the main entrance and made sure I was alone in the office. Then I locked the entrance door and went back to my office. I closed the door, took out the bag from the cabinet and started to take all the things out of the bag. While I was doing so, I could feel my heart starting to beat faster. It was so exciting. 



Then, I removed all my clothes and started to dress up. I was having such a rush putting on the outfit. I was a little scared too. Even the slightest of sound I heard from outside made my heart stop and I would just freeze wondering if someone was there. I finished dressing up and also put on the high heels. I couldn’t believe it that I was really dressed in my own office like that. Now it was time for me to put on the wig and some makeup. 

So, I opened the door slowly and walked out. I could feel my legs shaking as I walked towards the wash room. Just as I reached the wash room, I heard a car outside and I just dived to the floor. It was just some car driving by but it really scared the hell out of me.

I got up and then rushed inside the washroom, locked the door and took some deep breathe. After I felt a little relaxed, I put on the wig and adjusted it in place. I could feel the intensity of the moment and my body was trembling with excitement.



I knew I couldn’t use too much makeup incase I had to remove it quickly so I just applied some light makeup using foundation, eyeliner and lipstick. Then I put on the ear-rings and bracelet. I was happy with how I looked and I felt so cute & feminine. After some final adjustments, I stepped out from the wash room and it was so lovely to step out all dressed up. I felt like I really was a hot secretary at the office.

I walked around the office in my new attire and it was quite exciting than I had imagined. I just can’t express how thrilling it was for me to be all dressed up and walking around inside the office. I pretended I was a hot secretary at work. I took quite a lot of pics & videos posing at my co-worker’s desks and at different spaces of the office. It was so much fun. I was really having the time of my life. Then I went back to my office to take more pictures & videos there too.

When I finally looked at the time, I couldn’t believe that I had already spent more than 2 and half hours. I decided to take some more pics quickly and then change back. How I wished I could stay dressed for a few more hours but I had to avoid any suspicions.

So, I changed back, removed all the makeup, put everything back in the bag and double checked it. Then I went around the office just to make sure everything was as it was and finally closed the entrance door. I left the key with the security and drove home. It was one of my most amazing moment as a crossdresser. Looking at the pictures and videos now still brings back so many wonderful memories.

The End.

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5 Comments

  1. If i could look as “Hot” as you I would come out to my boss & co-workers about my fantasy of be being a “Hot Secretary.” IF They had no objections of me dressing as a woman & I could stay employed but as a secretary I would do it. Turn a fantasy into reality.

    1. I know how you feel, I love wearing skirt suits (miniskirt of course) & 4″ stilettos, dressed as a secretary I’d have no objections been given a good f$3%ing either.

  2. Thank you. U should write a book for me to read. Love Lew

  3. This title “Crossdressing in the Office” by Daniel reminds me of a similar encounter. I was not ‘Marie-Madeleine’ but myself as a male CEO of my micro-corporation, when I met a co-tenant of our office building. The said office building of the ‘Young Upwardly Mobile Individuals’ Mission Bay District is of the trendy loft-type, with an irregular floor plant, stairs and cul-de-sacs, indoor gardens and cosy little lounges with comfortable sofas for the guests to discuss “business”. A charming office building for all venues of operations, ranging to small studios-photos towards start-up in the game-industry (SEGA was down the street), which in fine, was the ideal place to meet anyone of special interest. This was on a Saturday early afternoon, and obviously I was all alone in the entire building. All was quiet, when suddenly, I hear the tap tap made by the high heels of a woman who walked fast. The noise approached the indoor garden, then, the woman appear. She was surprised to see me, when facing the large armchair where I sat, since it was partially hidden by in-door plants.
    A pretty girl! She stopped sort. I saw her taking a little breath. Her bare legs under a polka-dot blouse dress betrayed a hesitation, as if having been cornered into an unexpected situation. She looked at me in the eyes for just a quick second, then lower her eyes, as most women do. She was cute. A brunette, vivacious and intelligent looking. She then realize that this ‘stranger’ was harmless, so she said hello to me in a deliciously shy manner, but then she gave the give-away: She introduced herself: “Hi, I am Kristina”. I say give away, because having been a tranny and having lived among trannies in San Francisco, I identified Kristina as such, because bio-girls are never that agressive as to right away give their name to a stranger. However, this girl looked so good, and so natural in the following conversation that we had that I returned to my own first impression: that Kristina was a ‘real young attractive woman’, whom I’d like to date “as a male”.
    I had never seen Kristina, because she had just open shop as a photographer at the lower floor of the building. She had a boy-friend, so we remained in polite semi-distant terms for months. It is some times later that I had the confirmation of my initial impression. It occur at the nude beach (Baker Beach) when I saw Kristina in her ‘Eve’s’ suit. She was still very feminine in spite of being a bio-man. I nearly got fooled, and I am a cross-dresser myself.
    So Daniel, we have a somewhat similar story as crossdressing in the office, only seen from the other side.

    Have fun Daniel.
    XOXO, M-M

  4. I too dress up at work after everyone has gone home. It’s easy for me because we are a small company with only a few employees, so when everyone has left (and I am certain that they have no reason to “pop” back to the office) I grab my bag from the car and spend hours dressing up and dancing around to my favourite tunes. I have also dared to step outside the building but I have to act as though I am in a crime movie because other businesses have security cameras and I need to stay within their ”black spots” so that there are no recordings or sightings of me.

    Good luck pushing the boundaries but keep doing it, one step at a time.

    Steph-is-me x

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