“Goddammit!” muttered Sean as he held onto the desk for support. It was the third time today he had almost fallen over thanks to the stupidly high heels he was wearing, not to mention how his short skirt often rode up his ass and exposed his bottom to everyone else in the office. Sean just felt so done with everything, but of course, he knew there was no one to blame other than himself.
He had never intended to come off as rude or insesitive, when his female co-worker started to complain about sexual harassment in the office, he just felt her had to step in and clarify some points.
“Women often call it sexual harassment, but I mean, if they didnt like it that much, they could just switch jobs or maybe wear something other than skirts and heels right?”, he had said, thinking himself to have been as polite as possible. Of course, the ladies of the office didnt think like his comment in the slightest. That made itself evident when Sean was called by HR, his funny comment had now put at risk his comfortable job position and the promotion he had been working for over the last year. Sean of course was outraged, but seeing as how the HR manager was a woman, he didn't want to further hurt his chances.
“Now, Mr. Sean, outside of you tactless comments I do know you have been a very productive part of the team recently, this is why I have decided that instead of letting you go, we can try something else, a little sensitivity training”, Sean wiggled uncomfortable in his seat. He knew what the woman was referring to, it had been a new tactic developed by many companies that they used to avoid any scandals, as the mere idea of it often kept transgressors at bay.
“2 weeks of sensitivity training with a progress review at the end should do good enough for you”, said the woman. Sean weighted his options, and while the training wasn't appealing, neither was unemployment, plus, it was only 2 weeks he reasoned, it would be over before he even knew it.
That had been 3 months ago.
Sean had thought that just by coming in looking slightly androgynous he could play around the system, but was quickly shot down by HR, if he was to do the sensitivity training properly he would have to look and act like a full woman in the office. That is how he ended up using a large part of his salary on office trousers and blouses along with a makeup and hair treatment at a beauty salon. By the end of the first week, Sean, or Sasha, as his co-workers had started calling him, looked like a tomboyish woman to much of his frustration. His frustration only grew at the end of the second week, when HR had deemed his performance “unsatisfactory” and extended his training a further 2 weeks. It was ridiculous, he thought, but there was nothing he could do, as the weeks rolled by, Sasha was tasked with classical secretary level tasks while HR made sure he truly dived into looking like a woman. Sadly for Sean, his nasty attitude got him an extension again while also getting him a stricter dress code: Now he was only allowed to wear heels and 3 inch pumps, as well as having a minimum hair length. When he failed to abide by those rules, his training was extended into a full 3 months.
3 months in, Sean had long stopped bothering on changing out of his female clothes when he got home. The hassle of managing two pairs of wardrobes was just not worth it to him anymore, not to mention the hair extensions he had gotten in hopes of satisfying HR made it next to impossible to go anywhere looking as a man. His waist had cinched in noticeably thanks to wearing a corset daily which combined with his smoothed out legs made his womanly facade totally convincing, if not for one thing. In all his time dressing and acting as a cute secretary he still had not mastered walking on high heels! Such a simple thing is what had cost him his latest performance review and earned him another 3 months in training! “Sasha” was going to need to put in a lot more effort to ensure he wouldn't falt next time. At the very least, breast augmentation surgery was always reversible, right?.
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