Extended Training

 “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?.

Academic Expectations (Commission)

 David had been accepted into one of the countries most prestigious universities. It was like a dream for him as he had been given a full ride scholarship.  David left his old life to start anew at his new dorm. There he met his roommate, Mark, and together they managed to hit it off and become quick friends. Campus life was exciting as he got to hang out with the cool guys who were all model students,, but most surprising of all was the amount of gorgeous girls walking around campus and how flirty they all seemed to be, David was in high heaven. It was all going well right until midterm season rolled in, David had spent so much time enjoying his new campus life that he had forgotten why he was there to begin with. The school was very demanding so failure meant that David’s full ride was going to be cut short and get him kicked out.  Thankfully the university had been willing to offer David a second chance, as David sat down in the Dean’s office, he got offered to be part of a special program the school had designed especially for students falling below expectations, one that was meant to make the campus life easier for them while ensuring that the school morale remained high. Of course, David agreed without even bothering to read the paperwork in front of him.

However, as soon as David had signed the necessary paperwork he knew something was amiss, his hands looked tiny and delicate and his arms were smooth, rid of any hair. Long strands of hair fell covered his vision like a curtain as he placed his feminine hands over his face, feeling his skin smooth out, his nose shrink and his lips puff out.  Pressure built on his chest as two perky breasts spouted out. His waist pulled in and his ass expanded to girly proportions while his legs became longer and lost all their hair. Then, Gavid felt a tug over his groin and a sudden void between his legs. David remained seated for a moment still confused and trying to catch her breath.

“Now, Daphne, it's time you go and keep your roommate in high spirits, he is the school’s pride and i'm sure he needs to relieve some stress”, said the Dean

David spoke in his new girly voice and stood up, “Yessir! I will make him like, so happy” the new girl bit her lip as a heat grew between her legs. David panicked as he saw and heard his body move on its own, he tried to but he just couldn't get back in control, instead, he began thinking about how good Mark looked, how it would feel to have him on top while she spread her legs, about his thick rod entering her…by the time Daphne made it back to the dorm, she was already on her knees, begging to have a cock in her throat. That night Daphne learned what it felt to be creampied, but it stil wasn't enough, whatever the Dean had done to Daphne had made it so that the new girl only seemed to grow hornier and hornier, so it wasn't long before she went out and started visiting other dorms and assisting other guys in “letting out some steam”. Daphne would suck and fuck anywhere, be it the library, a dorm, frat party or even a lone classroom, she was the go-to slut for every guy looking for a god time

Now with the school year coming to an end, Daphne rides Mark’s cock like her life depends on it. Mark was set for another year of full ride scholarship thanks to his grades. David has agreed to be part of the special program until the end of the year, but thanks to Daphne’s great performance she had just earned a full ride scholarship inside the program. David tried to protest somewhere inside Daphne’s mind, but the feeling of another orgasm quickly washed those worries away. She was sure to keep up the school morale for a long time. 

Sister's Punishment

 

Will leaned on the wall, away from the rest of the party. He tried to catch his breath but the tight corset around his waist made it difficult. His feet burned, having been stuck in high heels all day. 

Just hours earlier Will had been enjoying some chips at his house. His older sister, Alice, had brought Liz over so that they could doll eachother up before heading to some party. Will wasn’t really interested in anything besides Liz, whom he had always found attractive. Of course, being a slim guy and shorter than his sister meant that Will had never built up the courage to talk to Liz for more than a couple of minutes, yet he’d always steal glances of her when he could. Perhaps that is why, when Will was going through the laundry and found one of Liz’s bra that her sister must have thrown in too, he couldn't resist the urge to pull it closer and embrace it, it was warm and smelled just as sweet as Liz. That was when his sister burst in and caught him red handed. 

They two girls had been furious. They overpowered poor Will and sat him on a chair with his limbs strapped to it and his mouth taped shut. “You know, Alice, I think that if this sissy pervert wants my clothes so badly, he can have them!” had said Liz in a fit of rage. Will had never see the two women in such a frenzy. His sister forced him into an impossibly tight corset that threatened to break his ribs. Liz then placed the very same bra Will had been using earlier over the boy’s chest along with matching panties. The main piece of the outfit was Luz’s black latex mini-dress, which Alice put on Will after coating the inside with a generous amount of what he assumed was lubricant. Liz then did the same with a pair of latex gloves and thigh highs while Alice began working on the makeup. Will’s eyelashes turned long and wavy while the dark eyeliner gave him a sexy look. His lips were decorated with lipstick the taste of which lingered in his mouth, The girls finished their rush by slipping Will’s feet into a pair of black heels and fitting a brown wig with a pair of cat ears over his head. Will was wondering why they had also been covered in the lubricant, until he caught a glimpse of himself in the mirror: whatever aspect of his maleness had been hidden under the guise of what he could only describe as a smoking hot babe, the corset did a lot to give his frame the much needed curves of a female, while also making sure he had to speak softly and move slowly. 

“Well, aren't you a hottie?”, said Liz before spanking Will’s rear, “fortunately for you, the adhesive we used will make sure you look pretty for a long time, months at least!”. 

Will went pale, adhesive? months? He had a job and college to attend to! His horror was evident on his face, so Liz spoke up once again, “but don't worry girl, we aren't monsters”.

“If you can get through the party tonight without your cover being blown, and get a guy to bring you home, we will give you the solvent you need”, said Alice, “what do you say, ´Willow’, up to for some fun?”. 

That had been hours earlier, they had dragged a feminized Will into the car and dropped him off at some random party all alone. Trying not to stand out, Will kept mostly to himself, but the girls had made too good of a job dollying him up, because “Willow” just couldn't seem to shake off the attention of the guys. As the party progressed, everyone grew drunk and more confident, Will had already felt more than a couple guys “accidentally” grab a handful of his latex encased ass. 

The worst part was when he had been dragged to the dance floor and felt the guy grinding up against his rear, desperate not to blow his only chance of getting the solvent, Will had grinded back on the guy’s crotch, feeling the outline of his hard-on. Once the song was over he had ran away and leaned on the wall, away from the party to try and catch his breath. It was barely past 12, and he could already see a few couples starting to passionately make out. Knowing it wouldn't be long before Will was forced to mimic them, he hoped that it wouldn't go further than that, but the hungry stares of the guys combined with a couple girls getting down on their knees shattered any hope of keeping his male pride. It was going to be a very long night.

Guilty Pleasure