“You’re so pretty.” The words had escaped me.
What had possessed me to say such a thing? We were alone in my office, Allison and I, having a work meeting. As we were discussing our latest design, she had stepped closer to me in order to draw on the whiteboard, and, at that moment, I could not hold the words back any longer.
I was so engrossed with her. “Pretty” does not begin to cover it, she is an apparition. Lithe, and so graceful in her every move. Her face, framed with wavy cascading brown locks, looked chiselled by Hephaistos himself, with an aquiline nose, high cheekbones and doe eyes surmounted by arched eyebrows.
She is also brilliant, our joint designs always improving on previously established standards. I was so taken with her. We were on friendly terms, but our relation had always been strictly professional.
So, my awkward compliment was quite unexpected. She looked so surprised. My tone had been explicit, this was no disinterested compliment, but a clear admission of desire and longing.
“I thought you were gay! I thought of you as my friendly gay colleague!”
She thought I was gay? I had been pining for her for years, and she thought I was gay? I guess it was my fault, never making a move, always admiring her from a distance. Well, that stopped now. In one bold instant, I kissed her. She broke the kiss and stepped back. This time, she was visibly angry. And for good reason, that was very inappropriate.
“Damian!,” she shouted. “How could you do that! Explain yourself!”
“I’m sorry. I shouldn’t have kissed you like that, but put yourself in my shoes: I’ve had a crush on you for more than 2 years, and still you thought I was gay. I was trying to be bold and confident, but I misjudged my course of action.”
“That you did,” she said, her ire softening somewhat. She stayed silent for a few moments, then continued: “tell you what, I’ll forgive you, but you’ll have to atone for this.”
“How?”
“Well, you invited me to walk in your shoes, how about you walk in mine? Both figuratively and literally.”
“I don’t understand, you want me to wear your shoes?”
“Yes. But not only my shoes. All my clothes. For a whole week. That’s the price to pay if you want to remain on good terms with me, and if you want to avoid me going straight to HR.”
Pleading ensued, but I was always going to accept. Truth be told, the threat of involving HR was unnecessary, I could not bear the thought of her remaining angry at me. I still didn’t know the specifics of her proposal, but I could just take time off that week, no one but her would know.
“Ok, I’ll do it.”
“Alright. Next week, you’ll be wearing my clothes.” As if she had read my mind, she added “and no taking time off. You’re wearing them at work, or the deal is off.” She had me. This occurred on a Tuesday, so I had time to mentally prepare, but could not wiggle out of this.
The rest of the week went by uneventfully. Allison and I barely talked, working on separate projects.
By Friday, I was wondering whether she’d go through with this. Maybe she had forgotten, or maybe she had cooled down and decided against it. But, as people were starting to leave, she came to my office and handed me a bag: “your clothes for Monday.”
In the bag, conservative, professional women’s clothes. A blue shirt barely distinguishable from the one I was wearing if you weren’t paying close attention to the cut and the side of the buttons. A pair of black slacks, again relatively neutral. I was relieved. Maybe people wouldn’t notice, maybe I could get away with this relatively unscathed.
As Allison was leaving my office, she instructed: “there are two other compartments, for shoes and underwear. Wear it all, and nothing else.”
I checked out the rest of my Monday outfit: the underwear was not conservative at all: red panties in some glossy material with lace inserts and the matching bra. Still, the panties would be hidden and I could hope the non-padded bra would be similarly undetectable under the shirt.
The shoes, on the other hand, would be in plain sight. They were black ballet flats. A clearly feminine design, but not eye-catching. People don’t look at plain black shoes, right? I closed the bag and left for home. Once there, I pondered: was I really going to go through with this? This was insane! I’d be a laughingstock!
But I had to. As I was resigning myself to that notion, a thought occurred: maybe the clothes wouldn’t fit me! I was slight of build, but surely not enough to fit into the clothes of a woman as gracile as Allison.
I undressed and stared at the contents of the bag. I grabbed the panties and pulled them up my legs. They were a bit tight, but not excessively. The bra was next, and I fumbled a while to clasp it behind my back before resorting to clasping it in front and then turning it around. It compressed my chest, but its cups remained empty. Trousers next. Again, they were tight, but again, I would be able to wear them. The shirt fit strangely, given my lack of breasts, but well enough.
I looked at myself in the mirror: my bra was hidden from some angles, but gave the illusion of small breasts from others. I would have to constantly be on vigil to keep it hidden.
Finally, I tried on the shoes. To my dismay, they fit decently as well. Despite being alone, knowing that I was wearing women’s clothes made me feel very self-conscious, and knowing these were Allison’s clothes aroused me slightly.
I decided to keep the clothes on for the rest of the evening to get used to them. If I was going to wear women’s clothes at work, I should first be comfortable with wearing them alone in my own home. In fact, I would wear them all weekend.
By Monday morning, I had gotten used to the clothes, but still had reservations about going to work in them. Nervously, I put them on. Nervously, I stepped outside and locked my door. Nervously, I climbed into my car. Nervously, I drove to work. In an advanced state of panic, I entered and rushed to my office, where I hoped I could hide most of the day. I was wearing Allison’s clothes at work!
I tried to focus on my work, but I knew people had seen me. Stan had stared at my chest inquisitively as I was greeting him, perhaps glimpsing the shape of my bra. I had overheard Janice and John talk about me.
I was mortified. Allison came into my office. I stood up, so she could see I was indeed wearing the whole outfit. “Show me the bra and panties.” I showed her a glimpse of my bra strap and lifted the side of my panties. “Good.”
The day went by relatively uneventfully. There was the odd whisper, but nothing more. Some people noticed, others did not seem to or pretended not to. Gradually, I began to relax a bit. A week would not be easy, but I could bear this, I thought.
At the end of the day, Allison gave me another bag. My clothes for Tuesday. I opened it immediately. Grey slacks, not too dissimilar from the ones I was wearing, but the top was a lot less neutral: a black satin blouse. I protested, but Allison wouldn’t hear it.
A new set of underwear (black) was included, but no shoes. I was keeping these on, apparently.
Once home, I reflected on what I’d done. I’d spent the whole day at work in women’s clothes. I still couldn’t believe I that had, and that I’d probably do it again the next day. I resolved to immediately try the new blouse, and rushed to my full-length mirror. It was undeniably more feminine than the one I’d worn all day, but there was still a chance, albeit slim, that it’d be confused for a man’s satin shirt.
And so, the next day, I was once again at work in women’s clothes. This time, the comments were not only behind my back: “hey, Mark, nice shirt,” said Alex, his words dripping with sarcasm. Anna similarly complimented my blouse on a separate occasion, but she seemed sincere. Later, on my way to lunch, I overheard the sniggers of some of the warehouse staff I passed. One of them even wolf-whistled me, eliciting great laughter from his friends.
Still, I focused on my work and the rest of the day went by quietly. As was quickly becoming a ritual, after most people had already left, Allison delivered me a bag of clothes. I opened it and brought out the first item: “a skirt? Allison, you can’t be serious!”
“I am. You accepted to wear my clothes for a week. My clothes include skirts. Did you really think you’d get away with a week in somewhat androgynous women’s clothes? Tomorrow, I want to see you in that skirt. I provided pantyhose to wear with it.” With those words, she left and I examined the contents of the bag in more detail. The skirt was a black pencil skirt. Holding it beside me, I determined that it would just about reach my knees. Alongside the skirt, another satin blouse, white this time. The promised pantyhose were there, with a new set of white satin lingerie. A new pair of shoes was also provided: another pair of black ballet flats, but these came with bright white satin bows on top.
My mind in turmoil, I drove back home. I couldn’t do it. I couldn’t go to work in a skirt! But I couldn’t disappoint Allison, either. And if I did, these two days were for naught. I did not know whether I would go through with it or not, but in case I decided to, I had to try this outfit on.
As I grabbed the clothes out of the bag, a note fell down: “look up ‘tucking’. You’re going to need it.” Mysterious. I made a mental note to do so, but first proceeded to put the clothes on.
I was wearing a skirt! Never thought I would, but there I was. And a problem was evident: a very unsightly bulge distended the front of said skirt. Was that the “tucking” mentioned in her note? I immediately opened my laptop and searched it. Yes, it was, and I instantly knew I was going to spend a frustrating evening trying to make it work. By late evening, I had found a setup that worked: no visible bulge at all, and it was finally secure and pain-free.
The image in the mirror was not as bad as I thought it’d be. I could almost pass as a flat-chested woman from the neck down. In fact, my skirt-framed and hose-clad legs looked quite good, I had to admit.
I set my alarm 30 minutes earlier than usual and prepared two sets of clothes for the morning: those Allison wanted me to wear, and one of my normal suit and shirt combos. 30 minutes would be enough to decide which clothes to wear and, if I chose the skirt, to tuck. On that thought, I took a much-needed sleeping pill and went to bed.
On Wednesday morning, my deliberations kept coming back to the fact that I had little choice. If I didn’t wear her clothes, Allison would resent me and I might get fired over the kiss incident. Both of those outcomes would be disastrous.
What’s a little ridicule compared to that? Tremblingly, I tucked and dressed. Getting into my car proved difficult, the pencil skirt making it impossible to enter leg-first, the way I usually do; I had to sit and swing my legs in. Thankfully, the skirt was not tight enough to impede my reach of the pedals.
I started driving. Driving in such an obviously feminine outfit felt strange. I was very nervous of being stopped by the police, or being seen by other drivers, even though only my blouse could realistically be seen. The time window during which I could still turn back, change and arrive on time quickly dwindled, then disappeared entirely. I was committed.
Everybody stared, few were composed enough to comment. At least my appearance took them by surprise. Most of the day passed by uneventfully. Most people ignored my outfit, even when interacting directly with me. I was still subject to some mockery, both behind my back and to my face, but it seems most people were indifferent to my rather sudden turn to crossdressing. A few were even supportive. In fact, Anna decided to walk with me to lunch, intent on making my trek through the warehouse more bearable. Allison, delighted that I was wearing the clothes she had instructed me to wear, joined us. The jokes, mocking wolf-whistles and outright laughter of uncouth idiots are a lot more bearable when engaged in pleasant conversation with two pretty women.
After lunch, I spent most of the day in my office until my latest bag was delivered by Allison. Unsurprisingly, this outfit was even more feminine than the one I was currently wearing. The usual satin blouse was pink, and the skirt was shorter. I estimated it’d reach about mid-thigh. A new pair of shoes was included, this time with kitten heels. I was surprised to find a razor. “For your legs,” she told me, “no hose tomorrow, just smooth, hairless legs.” For the first time, I did not protest. Sure, this was more feminine and the shaved legs would last even after the week was over, but if I could survive a day In a skirt at work, I could deal with two more. So long as Friday’s skirt was not even shorter.
Back home, I took a brief rest from my difficult day, then proceeded to shave my legs thoroughly. I then donned the heels, so as to get used to walking in them. As the heel was rather low, I managed to get the hang of it relatively quickly.
Thursday came and went much quicker than Wednesday. I was still an object of fun, maybe even more so, as my heels now advertised my arrival from further away, but I was better-equipped to deal with the ridicule. I also caught a few men staring lasciviously at my legs before looking up and realising their mistake. The first instance was somewhat disconcerting, but the next few times were just amusing, they seemed more embarrassed than me! Before I knew it, Allison was in my office, handing me Friday’s clothes. Satin blouse, as usual. This one is baby blue, with lace inserts, transparent shoulders and a plethora of little white bows everywhere. As I expected, another short black pencil skirt, but this one in satin, stretching the limits of appropriate dress for office work. The heels on the shoes were daunting: they were black pumps. Long gone were Monday’s androgynous clothes, she seemingly had assorted the most feminine outfit she could think of.
I suppose that was the plan from the start, but had she given me these clothes on the first day, I probably would have balked and refused. Whereas after four days of gradually more feminine outfits, there was little point. Since I was already wearing a pencil skirt, a satin blouse and heels, why would I have refused this outfit? Because the skirt is shinier? Because of a few bows on the blouse? Because the heels are higher? Of course not. She had expertly manoeuvred me into ultra-feminine clothing.
Once home, I immediately changed into the pumps. I needed to quickly familiarise myself with them. For some reason, I also wanted to try out my new skirt. Although I had not immediately noticed it, distracted as I was by shame and worry, the satin blouses had felt very nice on my skin, and I wanted to see if the skirt would as well. The answer was an emphatic “yes.” Every step I took plunged my thighs in a world of bliss. A good incentive to practice walking in pumps, as I would all evening.
As Friday morning came, I was much less reluctant to wear the clothes than I had been the days prior. They felt so nice, and the feminine image in the mirror, at least from the neck down, was growing on me. I arrived at work more relaxed than I had been the days prior, too. Oh, I was still nervous and ashamed of being seen like this, but I was more self-assured. I focused more on my work and less on what people thought of my clothing. Allison and I spent much of the morning preparing for a meeting with James, our direct superior, in the early afternoon. We then went to lunch together.
The meeting went smoothly. James had looked quizzically at my outfit, but refrained from making a comment or questioning me about it. The awkward moment passed, Allison and I explained our new design, to a positive reaction from James.
After the meeting, I spent a couple of hours alone in my office. For the first time in this crazy week, I was glad of my outfit. These clothes felt and looked very nice. The enormity of my situation hit me again: I was wearing women’s clothes at work! And very feminine ones, at that! In fact, I hadn’t seen any woman wear a more feminine outfit than me: many wore trousers and those few who did wear skirts approximated my Wednesday or Thursday outfits more than today’s. This time, this notion elicited more excitement than dread, though.
The day over, I was preparing to leave when Allison once again arrived in my office. As I was starting to enquire as to the purpose of her visit, she cut me off: “you’re so pretty.” With those words, she kissed me. My heart beating faster than ever, I returned the kiss. At the same time, I felt her hands on my sides. They caressed their way down until she was fondling my arse through my satin skirt and pulling me closer. The kiss lasted a blissful eternity. When our lips finally parted, she said: “thank you for this week. This was important to me, you’ve really shown a willingness to see things from the perspective of women.”
“I had no choice. I couldn’t bear the thought of your scorn. Had I known I’d get such a reward at the end, I wouldn’t even have complained!”
“I have another reward planned: I took a reservation for two at Chez Pierre, tomorrow evening. My treat. I hope you’re available.”
“I am. I will gladly go to the restaurant with you!”
“You don’t have to, but I’d like you to wear this tomorrow,” she said, opening a small, white cardboard box she had been carrying. In it, a dress. A “cocktail dress,” she called it.
The dress was cyan, of the most shimmering satin I’d ever seen. Unlike the skirts I’d been wearing the past three days, the dress’ skirt was flared. It stopped just above the knee, so my legs would once again be exposed. As would my shoulders and arms, seeing the tiny straps that would hold the dress up. She also handed me a new set of pink underwear to wear with it. The label informed me the set was pure silk. The bra was strapless, which would help given the dress. A layer of foam inside held its cups in shape. The bottom piece was rather long, “French knickers,” she informed me. There was no doubt in my mind, no hesitation: I’d be wearing those clothes tomorrow… and I’d be enjoying it.