Crossdressing Stories


Jims Office Adventure Crossdressing Story

It had been four years working as an administrator within a typical manufacturing company. Apparently our company made something to do with automobile engines, but it was all beyond me. Just get the job done well and people saw me as professional and hard working.

In the modern world it was accepted that guys could be administrators just as much as girls could be mechanics and to tell the truth, so long as I got the work done I was pretty much off everyone’s radar. Just ‘that guy in the admin team’ I suppose. If I thought about it I guess I should have known that it would all come out eventually, but I never imagined anything quite like what I’m going to recall here.

I was the only guy working in the administrative department with five other women under Lucy, the head administrator. We all got along, but that’s about as far as it went towards me. I still didn’t feel part of the collective, but didn’t feel any animosity from the other girls either. They were friendly enough, but, let’s say, I wouldn’t expect to be asked out on the town with them. I had been cross dressing for what now seemed like a very long time.

Initially it was shifty rummaging through female relatives drawers, longing glances through lingerie catalogs as a teenager, ending up with a rather extensive wardrobe of clothes, shoes and underwear now.

Living by myself allowed me the privacy that I liked to practice my fetish. I never really wanted to be a woman, but just loved the sensuality and power I felt dressing up as one. It always seems so unfair that women had all the glamour and fun! And I always felt a new confidence when I went out dressed up that I didn’t have in my ‘regular’ life.

My physical appearance helped a lot. Partly it was down to luck and my genes, but also diet and exercise that maximized my physical assets. I was naturally tall and skinny: 5 ft 11 in my bare stockings. Regular work outs at the gym kept me toned, avoiding bulking out too much! This left me with slender, shapely legs and kept my body and shoulders slim.

At 23 years old I looked young and fresh, and my mother’s genes had blessed me with a boyish delicate face and appearance. As a result I normally found that I had to try to ‘butch’ up for my daytime persona with crisp white shirts and shapeless trousers!

Like a lot of crossdressers I’d tried to give it all up, bundling all my clothes into bins and swearing to stop it all (usually after some near miss…), but it always seeped back into my life. At the time I was happy and comfortable with my lifestyle. I had a nice steady job during the day and an alternative female persona for evenings and nights out.

Each existence was separate and never crossed-over except for really extra-ordinary circumstances. But then this is all about one of those occasions, which led on to so much more… Work officially finished at 12:00 on a Friday, but I had too much work to finish and had to carry on into the afternoon. Tonight I had other plans though.

Tonight I was meeting up with some of my ‘girl’ friends (my crossdresser friends) in town and had a weekend break planned. We’d booked a minibus for us all to go down to London for the weekend, spending some relaxing time in a posh 5 star hotel and evenings in some of our favorite alternative clubs. I couldn’t wait to get dolled up ready for our mini-adventure.

The big problem was that I needed to be ready at 4:00 pm, which didn’t give me time to get home, change and get into town. That meant breaking my major ground rule of mixing business and pleasure. I had to get ready and dressed at work, and I had to bring in my weekend clothes to work. They were sat in my weekend bag, which I had brought in early and stashed out of sight under my desk. By 2:00 almost everyone in the building had left for the weekend.

There were a still a few engineers and executives about, but I was sure I hadn’t seen any girls around. I was planning to make a break for it to the ladies, so once I was inside there I was safe. A lot of the lights had already been turned out and the day was turning to winter dusk outside. I finished up my work and now it was time for me to get dressed up.

Handily the women’s toilets were located just out of sight from the office door a little along the corridor. By now I hadn’t seen anyone pass our office door for 20 minutes. I was certain there was almost no one else left here, but I felt a little tingle as I got up with my weekend bag to sneak to the ladies. With my heart beating hard I left the office and turned left down the corridor, pausing at the water cooler to take a slow drink and pretend to read one of the company’s motivational pieces on the news board. “OK, this is it,” I thought after no one had left the ladies for a good 5 minutes, “All the admin girls have left, it’s now or never”.

Confidently I picked up my weekend bag, slung it over my shoulder and moved quickly and quietly down the corridor, past the men’s room, and with one last cautious glace over my shoulder slipped into the sanctuary of the ladies toilet. My heart was still pounding as the automatic lights flickered on. No one in here — phew! Just to be sure I went into the second to last cubicle and locked the door. Now I could relax a little and get into my dressing routine. I quickly stripped off and filled the carrier bag I’d brought along with all my day clothes.

Last night I had spent a luxurious evening bathing, waxing, shaving and moisturizing my entire body. Now I stood for a moment enjoying the feel of my hands gliding over my soft smooth body. Sitting down on the loo I pulled on a pair a silky hold up stockings, the light fabric gliding easily up my freshly waxed legs. And with my pair of black leather boots that went up to just below the knee zipped on at least now I would appear ‘normal’ from under the toilet door in an emergency.

Feeling much more relaxed now, I could really go to work on my female image. First I attached my wonderful C cup silicon fakes and blending in the edges with some foundation. I then got out my pocket mirror and starting to apply my makeup. Not too much, but enough to bring out some of the natural feminine look to my boyish face.

By keeping it low key I could normally pass without too many unwanted double takes. So, I applied some of my favorite foundation followed by a light dusting of blusher to bring out my cheekbones. Next I put on some dusky eye shadow to match my hazel color, followed by coal grey eyeliner to open up my eyes and the first coat of mascara.

My favorite subject at school was always art: who knew being so handy with a brush would come in so useful! The only real splash of color was reserved for my crimson lipstick, with a touch of lip gloss.

Tonight I was going for elegant and stylish, so standing up again I slipped on a delicate lacy black thong, followed by the matching bra. Then I wriggled into my killer Little Black Dress. I loved this dress and always pulled it out for a good night out. It hugged where it should, hid my worst bits and fitted like a dream.

I guess the way the hem line ended just below my stocking tops helped too! Next I applied some pre-prepared crimson painted nails and while I waited for them to dry I brushed on a second coat of mascara and fluttered my eyelashes to myself in my mirror. Finally I took my favorite brunette bob wig out of the box in my weekend bag and fixed it into place. It was a modern cut that angled forwards and down with a straight cut fringe.

It went very well with the young-classy-thing I was going for. With some luck I might make someone’s night in the bar tonight! Once I was happy with my appearance I gingerly opened the cubicle door to check myself out in the bathroom mirror and make any final adjustments. “Woh, cute honey,” I thought to myself.

I whispered another silent prayer to the cute gym instructor that had come up with the routines that had added shape to my cute ass. Just need a few tweaks to my blusher, tidy up a stray hair or two and I’m ready to hit the streets! I turned back to the cubicle and picked up my makeup bag off the toilet seat and put it next to the middle sink. I then leaned down to retrieve my day clothes and stuff them into my weekend bag.

Now fully dressed I was enjoying the snug fit of my clothes and as I bent to pick up my bag I relished the feel of my black dress’s hem inching up the back of my thighs to reveal a peek of stocking top and bare flesh. Mmm.. that felt good as I kept one leg straight and paused bent over double reaching for my bag.

Just as I was enjoying the luxurious stretch down the back of my leg, I froze mid bend as I heard the outer door suddenly swing open. Panicking I stood upright again, but didn’t know what to do. The inner door opened and I heard heels tap across the tiled floor. “OK… OK… keep calm and casual,” I thought to myself.

My heart was beating so hard in my chest I felt sure anyone in the same room could hear. Clutching my bag I returned to the sink where I had left my makeup kit. By looking down slightly I could keep the fringe of my wig concealing my face. With some luck she’d go to a cubicle and I could slip out without any questions or confrontation.

Flicking my eyes up to the mirror I saw that I looked good enough to pass, it was just a pity I couldn’t do a final touch to my makeup. With a feeling of dread I felt the presence of someone walk behind me and take up position at the next sink. “Why had I taken the middle sink?” I thought to myself. “Oh no, now I’ve got to stay and do something at least else it looks odd.”.

I took out my blusher brush and touched up my face, trying desperately to look calm and collected. Glancing to my left in the mirror I saw Helen, one of the senior executives styling her hair with her fingers and a small can of hair spray. “Idiot!” I thought, “Of course there was Helen as well as the office girls.

I’d forgotten about the one female executive who could be working late in her office!” “God, these long meetings play havoc with my hair!” she said. “I’m sure it’s the air conditioner, but I always come out of that room looking a mess.” “Yeah, I know what you mean,” I mumbled in my feminine voice, desperate for something to say.

“And I’m supposed to be going out tonight,” she said, “now it’s too late to go home and I’ve got to keep these stuffy work clothes on.” So far she seemed far too preoccupied to notice me much, so with gathering confidence I chanced a longer look to my left. She was wearing a modern cut navy blue skirt suit, with a white blouse underneath.

The suit suited her figure well and true to Helen’s form the skirt was that little bit shorter than necessary for business. I had to admit that she looked good, just as she always did. She was rather short, under 5ft I estimated, but her sensuous curvy body and larger than average chest more than made up for it.

Matching navy blue 3 inch high heels also helped disguise her height, with the added bonus of making the most of her heart shaped rear. And if she wasn’t eye catching enough there was the shock of fiery red hair which contrasted so well with her creamy white skin.

“No, you look great,” I replied “Just maybe lose a few buttons on your blouse and add some more makeup and you’ll be OK for bars.” I couldn’t believe what was going on here. I needed to leave and here I was having a conversation with one of the high level management dressed as a woman! I’d be lucky to keep my job if she realized.

“Oh, thanks,” said Helen. “Could I borrow some eyeliner? I don’t keep any at work.”

“Sure,” I replied, cursing myself for mentioning makeup. I rummaged in my makeup bag and passed her my eyeliner, without turning away from the mirror. I continued to tweak my hair and makeup while Helen concentrated on applying eyeliner. She finished what she was doing and passed me the makeup.

I turned to take it and fumbled it with the rest of my makeup back into my weekend bag. “Right I better get going,” I said, still trying to avoid eye contact with Helen. “OK. Me too, I’m about done in here. Thanks for the eyeliner again.” “No problem,” I replied. Turning to leave, we both made for the door and for an instant I looked straight at Helen.

There was a slightly quizzical look on her face, and then it was gone. I opened the door and pushed my way out into the relative freedom of the corridor. “Looks like you’re on for a big one,” she commented as she followed me out “What are you planning?” “Um… I’m meeting some friends in town and we’re going. down to London,” I mumbled.

“Uh huh…” she answered “… well you have fun” she finally said.

Still on edge I turned to go, but was called back after three steps. “Excuse me,” said Helen. “I hate to do this, really I do, but you do work here don’t you?”

“Sure,” I replied casually, screaming on the inside, “down in the finance office with Sue.” “Oh, just I haven’t seen you around much. Are you new?” “Yeah. I transferred from the Northern branch 3 months ago.” “Ah right I see.” There was another long pause, “sorry to do this, but can I see your ID? We’ve had a few security breaches recently and you can never be too careful.”

“No problem,” I replied. I squatted down next to my weekend bag and made a big show of rummaging inside searching for my ID. Desperately I thought “What am I going to do now? I can’t show her my card!” “Sorry, I must have lost it somewhere,” I said with maybe a little too much confidence.

“Right.” said Helen. She sighed and finally added, “Well, would you mind coming with me while we sort all this out?” “Sure, but I do have to go soon you know.”

“Yes, this will all get sorted quickly one way or another,” she replied ominously. Feeling like I was falling in a dream I followed Helen back through my office past my desk and towards her executive office along the far side.

I’d never ventured into her office before and I was surprised how nice it was in here compared to out in the drones section. There were large windows down one side of the office, looking out over the landscaped grounds our office block sat in.

A large desk dominated one corner of the spacious office, with a wall of books and files to the left of it. In the opposite corner to the desk was a low coffee table surrounded by 6 easy chairs. Evidently this was where the deals were made.

The only other furniture to be seen were a selection of large foliage plants dotted around the room, Helen’s black leather high backed office chair and a further standard office chair pulled up to the other side of the desk. She went behind the desk and sat before motioning me to sit opposite her.

“OK then…” she said, “sorry, what did you say your name was?” “Rachel,” I blurted out, “Rachel Stevenson” “OK then Rachel. We need to find your ID in a hurry or get you cross checked with Security. What’s it going to be?”.

By now I’d resigned myself to losing my job and life as I knew it, so it was either humiliation now with Helen or humiliation with Helen and a selection of security guards as well. I tried to swallow, but my mouth was too dry. I tried to think of something clever and then it hit me.

“I am sorry but the truth is I am just here to fill in for Jim. You see, he’s my close friend and he wanted me to finish some of his work. Since, he had done me a big favor a few weeks ago; I came in to help him. Apparently he had some personal work to complete today. I am really sorry.” I said timidly “I shouldn’t have done this. Please don’t call the security.”.

“Well, why didn’t you say it before,” Helen exclaimed, “I know Jim, not personally but I have heard a lot about him. He’s a good worker. He must have had something really important to call you in.” Stunned, I just nodded.

I couldn’t believe that she really said that. I felt a moment’s pride at the realization that she hadn’t recognized me and believed my story. Helen got up from her desk and eased down finally. “You can go now” she said with softness in her voice. “Thank you so much,” I replied. “Have a nice weekend,” Helen said and we both walked out of the office.

I held my breath until I was out in the corridor. After what seemed an eternity, I was finally out of the building. I checked the time and there was still time to catch up with my friends. What an afternoon it turned out to be.

The End

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  1. Thank you for this story, I loved to read you.
    It was really cute. All allong I was sure you would come out to Helen and she would go to London with you but it ended well.

  2. Love to hear a story about Daddy catching a young cross dresser

    1. you mean you’d love to catch a young crossdresser

  3. I’d love to see some photos!
    Anthony xx

    1. Me too, I’d love to see that killer LB dress

  4. Me too, I’d love to see that killer LB dress

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