Company Girl Ch. 02

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Matty slips deeper into his transformation.
4.4k words
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Part 2 of the 5 part series

Updated 06/13/2023
Created 02/07/2023
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Matt barely slept that night. Avery's words rang in his head endlessly. He wasn't sure exactly what she had in mind for the future or how long he would be in chastity at home and it worried him deeply, but what worried him more was how turned on he was by the situation. Even after Avery stopped touching him, his whole body felt awake in a way that it never had before. His skin was more sensitive, he was more aware of every little touch, the feeling of the silk sheets Avery always used sliding past his thighs. And the thought of Avery having this much power over him...well, that turned him on too, and if he was honest with himself, it overpowered the fear by quite a wide margin. Sure, maybe Avery was taking that control in a direction he wasn't entirely comfortable with, but she had been open to exploring his kinks, why couldn't he do the same for her? If being called a girl in the bedroom meant that Avery better accessed her dominant side, that was a price Matt was very much willing to pay.

These thoughts were still on Matt's mind as he walked into work the next day. He managed to find his way through the maze of hallways back to Sloan's office after a few wrong turns and saw her already working steadily at her laptop. When he entered, she looked up and smiled.

"Matt, glad to see you're on time. Today the real work starts, but before that we have one more piece of business to attend to."

Sloan stood and motioned for Matt to follow as she led him out of her office and down the hall, into what looked like a large walk in closet. However, all the outfits in the closet were the same. They were identical uniforms like the ones Matt had seen worn by the incredibly attractive group of women the day before. Most of the uniforms were identical to the ones they were wearing, but a small section consisted of a variant that looked like they were for men. There were only 3 or 4 of these, as opposed to dozens of the ones for women.

"You may have seen other assistants wearing these yesterday. All assistants are required to wear them so they can easily be identified by anyone in the building. You see, though you are my assistant, your job also requires that you help out anyone else in the building should they need it. Your first priority will always be my needs, but we find that having a communal staff of PA's helps productivity and boosts morale for everyone."

She took one of the male assistant uniforms off the hanger and handed it to him. It consisted of a shirt and pants which, while obviously male, had a feminine quality to them. He couldn't put his finger on what exactly about them made him feel this way, perhaps the cut of them.

Matt began to undress. He was a bit embarrassed to do so in front of Sloan, but seeing as she had seen him completely naked the day before, he figured this wasn't that bad. As disrobed, he asked, "All the assistants I saw wearing this uniform yesterday were women. Very attractive women I might add. I'm guessing that's not a coincidence."

Sloan laughed. "No, it's not. Most of my colleagues who are at the level to have their own assistant are men. Men tend to want...a particular kind of person working under them. It doesn't bother me as much as you might think. All our assistants here are very talented at their jobs and having more beautiful women around the office isn't something I'll complain about anytime soon."

Matt thought he detected some subtext woven into her last statement, but didn't want to pry too far into his boss's personal life on his second day.

"Avery always said, 'Sloan is the biggest advocate for other women I've ever known.' and I can't deny it after what you've done for her." Matt finished buttoning his shirt and looked up just in time to Sloan plant herself right in front of him.

"Kneel," she said. Matt knelt, compelled again by invisible hands. "I told you yesterday, you are to call me Ms. James. We are not equals and I expect you to understand that."

Matt shivered, a chill spreading throughout all his nerves. He felt his skin tighten and tingle. He recognized the feeling as arousal, but it felt different from anything he had felt before, even last night. He desperately tried to hide any signs of his sudden horniness, simply replying, "Yes, Ms. James."

Sloan helped him, and while moving Matt noticed hard fabric pads sewn into the chest of the shirt he had put on. They were positioned directly over his nipples and felt uncomfortable scratchy as they moved over his body.

Sloan saw him examining them. "Ah yes, those. Our uniforms are very tight fitting and for the wearer's modesty, they put those in so that your nipples won't show through."

Matt hadn't noticed before, but the outfit was tight fitting, almost wrapping around his form like elastic. He examined himself in a mirror on the opposite wall. He normally wore an undershirt and bought his buttons up a size big, so as to try and hide his smaller than average frame, but this outfit emphasized it. He realized that not only did it make him look a little effeminate, it also highlighted the size difference between himself and Ms. James. He felt another slight shiver run through his extremities.

"Come now, we need to get the day started."

The rest of the day was surprisingly normal, at least compared to his previous time at BioProl. He sat at the corner desk in Ms. James office and got acquainted with her calendar, files and projects. He would hop on any call she took, taking notes and compiling them for her. He attended one meeting with some of her colleagues and this turned out to be the only odd spot in the day.

"Everyone, this is Matt. He's my new assistant. As always, if you need him he is available, but he's also new, so maybe give him a week or two to really soak in some of the company culture before giving him more than he can handle."

Everyone chuckled at this, except Matt, who didn't really see it as a joke, more just a statement of fact. If this was the company culture, he didn't see himself "soaking" up much of it. He had never been very close with other employees anyway. His life was outside here, with Avery and his friends.

Throughout the meeting, Matt would catch one of the men staring at him. He supposed they were technically his bosses and maybe just wanted to size him up, but he caught more than one looking him up and down, like they were examining his body. The outfit he was wearing was revealing and odd, he had to admit. But wouldn't they be used to seeing assistants in this outfit? Then again, he hadn't seen any other male assistants so...

He mentally shook himself and scribbled down the notes he missed. He was determined to do a competent job for at least the month trial period, no matter the odd circumstances. "I can stand anything for a month," he thought, refocusing himself on the meeting. "I've worked much worse jobs for longer. The salary is better than any job you've had before and you're helping Avery. That's what matters."

However, it was during the meeting that he first really noticed how annoying the pads in his shirt were. Anytime he moved, they rubbed on his nipples until they were hypersensitive. It went from uncomfortable, to distracting, to unbearable over the course of the day. He also noticed that they were beginning to feel wet. On a trip to the bathroom, he unbuttoned his shirt to make sure there was no blood, which was the only explanation he could think of. But he found that the wetness was from a clear liquid that covered the whole of both pads. He tried to wipe it off, but was unable to get them dry. He went back to the office confused and agitated. The second half of the day was a desperate fight to stay focused on his work, but found that the agitation on his chest was slowly being replaced with another sensation: pleasure. He figured it was from his nipples being overly stimulated, but every time his shirt brushed over them, he felt a feeling similar to when Avery had touched the head of his dick. Of course, it wasn't nearly as intense but that wasn't saying much considering. It got to the point where he feared Ms. James would notice his constant arousal and he decided he needed to get ahead of it.

"Ms. James, I know the day is nearly finished and I hate to complain, but this uniform is very uncomfortable. Is there any way that I could bring my own clothes tomorrow? I have some that look fairly similar."

"Hmm, well I'm sorry that the uniform hasn't been working out for you, but unfortunately we need assistants to all dress the same. We want you to be visible and accessible and for other employees to know who in the office they can use if needed. I'll have an alternative worked out for you tomorrow."

Matt left wearing his new uniform, unable to locate where his old clothes had gone. He got a number of strange looks from other passengers on the bus, but barely noticed. His attention was solely focused on his chest, where two perky nubs of pleasure resided. He found himself shifting back and forth in his seat to move the fabric across his chest. He had never really paid attention to his nipples before, but now they occupied a space in his mind that used to solely be focused on his dick. His arousal built and built, but his dick never even attempted to get hard, much to his frustration. He felt captive to the feelings flowing through him, unwilling to end the soft pleasure he got from contact with his nipples, but desperately angry at his inability to make these feelings go further. He practically ran home, only stopping when running caused too much pleasure for him to bear and ducked into an alley, slowly rubbing his chest in small circles. The wonderful feelings increased, but so did his desire to cum. He made it the rest of the way home and beelined for Avery as soon as he stepped in the door.

"Please, you have to remove my chastity. I have to get off right now."

Avery looked at him, startled but bemused. "Was there someone doing burlesque on the bus or is your company just making sexier shaped pills than ours?"

"No, its....it's these," he said, practically tearing off his shirt. This revealed two puffy areolas and nipples standing at attention. "They've been agitated all day. It's to the point where they're swollen, but it's not painful."

Avery inferred what he had left unsaid by the way that Matt subtly stroked himself while he held his chest to show her the problem.

"This is unbelievable. Sloan said some things might change, but I never expected this after one day."

"What do you mean? What changes?"

Avery tore her eyes away from his chest and stared at Matt before averting her gaze. "No, I just meant that I knew you would be horny with that cage on, but I didn't expect it to get to the point of you wanting nipple play after just one day locked up. It's very cute, seeing you so desperate."

Avery whisked him into the bedroom before he could voice any other questions. He knew that Avery was kept informed on all the treatments he was being given at BioProl, but was it possible she had requested one herself? Ms. James had said she could alter his hormones, maybe she could increase his libido too? Why would Avery request that?

Avery threw him onto the bed. She mounted him as she had the night before and gently pinched his alert nipple. He gasped, everything else forgotten. She stroked one with each hand, alternating light and hard until once again, pleasure radiated out within him, but this time from his chest. Matt lost himself in the feeling. His hand instinctively went between his legs, but stopped when it encountered the cage and his soft member. He groaned, only half in annoyance, and tried to focus on Avery and her beautiful body above him. He cupped her breasts, returning some of the sensations she was giving him. They continued like this for several minutes, with Matt mimicking the motions done by Avery back onto her own larger nipples. Avery then let up with one hand, reaching behind her for some object Matt couldn't see. Suddenly, he felt strong vibrations on his dick. Avery rubbed her vibrating wand up and down, causing his whole dick to tingle, when the parts encased within metal. She lowered herself down onto the other side, pressing it harder into him. From there she started to gently move back and forth, clearly enjoying the vibrations on her clit.

Matt was enjoying it too. The feelings coming from his nipples only intensified as the sensations in his hips grew. Just as he felt he might be able to finally cum, Avery turned around and positioned her pussy above his face. Leaning down, she pressed herself against his mouth as she took his own shrunken member into her own. Matt was frustrated that he had gotten so close to orgasm only to be denied, but he dutifully started to lick at her clit. Once again, he mimicked the motions she was making on the head of his own dick, as that seemed to get an extremely enthusiastic response from her. She ground into him, rocking back and forth until he felt her shudder and moan loudly. A second later, she turned around and kissed him deeply. He felt her push something into his mouth, which he swallowed instinctively.

"You were so drippy baby. I've never seen you cum that much."

"What do you mean? I wasn't able to cum." He looked down and saw a line of precum connecting his tiny dick to the sheets below. It was still flowing freely and Matt realized that this was what he had swallowed.

"Oh, well, you certainly seemed excited anyway. I love a girl who gets wet from giving pleasure."

"Could you take this off just for a minute so I can cum too?" He reached down and held his shrunken package pleadingly.

"I think you came enough for one day. I don't want my kitten getting spoiled." With this, she scooped up the string of ejaculate still oozing out of him and lay beside him. She slowly traced it around Matt's lips, until they were shiny with cum. "No one wants a pillow princess, and the more motivated I can keep you, the better." She kissed him deeply, their coupling slick with the evidence of Matt's enjoyment. "I look forward to playing with my little slut even more tomorrow. I know a lot is changing, but I think we are both going to be happier than we've ever been. I love you Matty." With that, she turned over to sleep and Matt settled in for what he knew would be another long, sleepless night.

The next day, Matt walked into work tired and a little out of it. As predicted, he got almost no sleep, as he had been unable to stop himself from endlessly rubbing his nipples and dick on the soft sheets in an attempt to orgasm and free himself from the prison of arousal he had been in for two days. He walked into Ms. James office and nearly fell backwards as she grabbed his arm, directing him back out.

"I have a replacement uniform for you. It's the best I could do on short notice."

She led him to the same room as yesterday and handed him another garment, which Matt was confused to see was one of the dresses from the women's racks.

"It's been tailored for you. Obviously they had to alter it a good amount, but I think it should fit fairly well. Before you ask, yes it may be a dress, but all the men's uniforms have the patches and I need you focused today. We'll figure out a better solution long term."

Matt wasn't an idiot. Nothing about Ms. James's explanation or reasoning made sense. Something wasn't right about this whole company for that matter, but he couldn't come up with a better solution other than quitting, which he wasn't ready to do just yet. That, combined with his fatigue, had him undressing and putting on the frilled garment without argument. The dress fit snugly and he was surprised to see that despite it being designed for women, it actually fit his shoulders and chest well. Besides the frilled skirt which ended just above his knees, it actually didn't make him look that much more ridiculous than his previous uniform. He had to admit, he looked pretty good, in a genderbent kind of way.

"Stockings too. Showing your legs around the office wouldn't be seemly." Sloan playfully slapped his behind, smiling. Matt turned bright red and covered his butt with his hands. Sloan directed him towards a chair and he sat down hastily. She brought over a pair of opaque black tights, which she deftly rolled up before sliding down Matt's outstretched leg. It was intensely confusing for Matt as the intimacy of the act, coupled with her speed and skill made it both arousing and uncontestable. She slid the stretchy material down his other leg, then instructed him to stand up so she could adjust the waistband around his hips. All Matt could do was stand demurely as she fidgeted with his clothes. The stockings seemed to have some kind of panties sewn into them and they pressed his already shrunken dick flat against his body.

"My, aren't you cute? Would you like me to use some makeup on you so you fit in with the other girls? I think with just a little bit, you might be able to pass for a, admittedly flat chested, woman. That might be easier on you than explaining why you're wearing this."

Matt just shook his head. Being handled so easily and thoroughly had left his head spinning and his body unable to move outside of the directions that Ms. James had given him. Matt knew that what he was experiencing was well outside the realm of normal, but on a subconscious level, he relished in having Ms. James take control. He had recurring fantasies about submitting completely to women, mostly Avery, and he was still unsure whether he was dreaming or it was really happening. Of course, he was pretty sure that he wouldn't have picked the outfit he was wearing if he was dreaming, but in that moment, all he cared about was that his fantasy continued.

'Alright then, follow me. We have a big day ahead of us."

The big day was a phone conference with inventors that it seemed half the company was taking part in. Matt prepped documents, gathered notes and helped Ms. James with a hundred other things before filing into a huge conference room with 30 or so other employees.

"No need to take notes today. You're in charge of retrieving whatever I or any other employee needs, whether that's a missing form or a cup of coffee. You and Chloe will working together, she can help you if you have a question about where to find anything. Understand?"

Sloan had pointed towards one of the other assistants in the room who Matt deduced was Chloe. Like all the others, she was very attractive, with soft features and big eyes that were now focused on the man she stood behind. Matt assumed this was her boss, which was confirmed when he beckoned her forward to whisper in her ear. Matt recognized the man as one who had eyed him extensively in yesterday's meeting. Chloe stood from a kneeling position and returned to her position behind her boss, but not before glancing towards Matt and giving him a mischievous look.

Matt didn't have time to unpack this before the meeting started. People dialed into the conference line and negotiations Matt didn't fully understand proceeded. Matt let his mind wander a little as he didn't need to take in every word for note taking. Matt ended up staring at Chloe without realizing it. She had her hands dutifully clasped behind her back, which combined with her black and white dress, gave her the look of a maid ready to serve. Matt realized with some shame that someone looking at him might see the same thing. He intentionally stood with his legs apart and arms crossed over his chest, trying to regain some masculine pride. He realized that Chloe's boss, who he had heard introduce himself on the call as Mr. Belleck, was looking at him and smirking. Mr. Belleck brought Chloe to him again and whispered in her ear. She stood up and walked towards the door near where Matt stood. She passed him, lightly tapping him on the arm and indicating that he should follow.

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