encouraged-transformation
FETISH STORIES

Encouraged Transformation

Encouraged Transformation

by crissyribbons
19 min read
4.7 (20100 views)
adultfiction

Chapter One

Rob was feeling his life slide into a kind of routine. It was pleasurable in the short term, but he was not at all sure about what might come after, or how it was affecting his long term plans -- professionally or personally.

He worked in a large office -- large enough to get a bit lost in, as long as he met his deadlines and kept his supervisor happy. But it was also large enough and the work specialised enough that he found himself getting bored with it. At first, he overcame the boredom by just filling his off hours with fantasies and porn, but that was starting to leak into more of his time as things went on.

It used to be he'd head home, picking up some dinner on the way and devouring it while his computer started up. His evening would be a blur of stroking himself to a river of porn, in between or while chatting with others who shared his interests or led him on to theirs.

He looked at all sorts of porn, starting off with the 'normal' stuff, but sinking deeper and deeper as he explored on his own and was led down other paths by the men he found himself chatting with. Maybe it was because of the almost exclusively male community, or maybe it was just remembering those long-forgotten dreams and fantasies, but he found himself looking at more and more sissy porn.

He'd always been a bit slight, physically. He was never the star athlete, and swimming was the only sport he'd come close to succeeding at. He'd look at himself, having taken to getting more and more naked as he watched and stroked, in the privacy of his apartment, and think of himself in the position and predicament of the sissies and submissives in the videos he watched.

It didn't take a lot of encouragement from his online friends to order some lingerie for himself. He was so thrilled when the first packages arrived that he was rock hard before he even got upstairs.

It set up a whole new routine for Rob. Once home, he'd strip completely and re-dress in lingerie. Only then would he sit down to sink into his porn fuelled stroking and fantasies. Stockings, garters, panties, girdles, bras and corsets... his collection just kept growing. He would stroke and chat to these men. He even began, at their encouragement, to start sharing photos of himself while dressed up. The arousal was like a drug for him, and in that high, he dared to do more and share more than he might have otherwise. There were mornings he woke up with regret or fear, but he'd be back online the very next night.

That lasted for a while, but soon his dreams and lusts were calling out to him during the day as well. The hours spent at work, never mind commuting there and back, just seemed far too long to spend away from it all.

His friends online had an easy solution. Some of their chatting sites had mobile apps, and he could take them with him. He could also start tossing out that ugly and boring male underwear and start wearing his pretty things to work. They tempted him with how good the fabrics felt against his skin, and how sexy it would be to have this secret during the long dull hours in his cubicle. How much more interesting meetings would be, when no one else would know he was tucked into panties just a few feet from them.

They were right. It was an incredible feeling. On the subway, walking down the street, and every moment in the office... he was aware of the bits of lingerie he wore under his outer clothes. Panties and stockings under his suit, with no one knowing a thing. No one but his online friends, who urged him on and teased him just the way they knew would affect him most.

Soon, they suggested toys to add to his experiences. Rob was very new to that, and it worried him perhaps as much as it excited him. Not enough worry to stop him, no, but he started slow. Just a small butt plug at first. It felt so strange going in those first few times, along with the cold slippery feeling from the lubricant. Rob got used to it quickly though, and started to feel those sensations become part of what made his pleasure more powerful and complete.

He knew his productivity was slipping, but he was sure he was still getting by. His every spare moment was spent on his phone, checking in, giving updates on how he was dressed, what toys he was using, and even about the situation around him. He'd tell them when he was going into meetings, and they'd tease him with comments and suggestions.

It got even more intense, once he purchased the vibrating plug that could be controlled online. He'd turn the thing on and post the control link to his friends... and from then on, he'd never know when it would start to hum and shake inside him. They would often choose times during meetings and presentations... but of course, they only knew his schedule because he told them, so they tormented him with the knowledge that he was asking for all of this.

He knew he was offering up more and more to them, to feed their enjoyment of his compliance and his play. He hadn't shared full images of himself sissified publicly, but he had sent them to a couple of them whose enjoyment of him really resonated. They were more than friends. They were starting to take some control.

One in particular was good at taking charge in ways that left him feeling so aroused and downright helpless to do anything but obey. He was so often the first to take control of the remote control toy in his ass, or to give him suggestions on what lingerie to wear any given day. Rob started to communicate with him privately, more and more. With this one man he would share everything. Rob would pose for the photos he wanted, even showing his face.

One day, the man he knew only as 'Master' asked even more of him.

"I want you to stay at work late tonight. If anyone asks you can say you're behind on a deadline, or you can just hide in the washroom until everyone else has gone -- it doesn't matter. But I want a photo of you, in nothing but your stockings, panties and bra, up on the boardroom table of your office. I want it tonight. No excuses."

What could he do? It wasn't just that Master had all these images of him, that he was afraid of the implications of disobedience, no... He wanted to please his man. He wanted to make him happy. He wanted to turn him on.

Rob lingered at his desk as time slowly slipped to 5:30, and then to 6:00... One by one, his colleagues left and headed home. One or two asked him about his late hours -- obviously a rarity for him. He made his excuses and lies, blushing and squirming the whole time.

He went to the washroom for a while, teasing himself under his pants but over his panties. He didn't want to cum, not yet, not here. He didn't want to lose his nerve.

Rob went back to his desk, and it truly felt like he was alone now. He strolled around the office, so very quiet and empty. He took a deep breath and made his way to the maid boardroom. All looked clear still.

He texted Master, letting him know it was about to happen. He slid inside and closed the heavy wooden door behind him. He walked around, and figured out where he could set his phone to get the full view of his body.

He stripped quickly, kicking off his shoes and peeling out of his suit. Jacket first, then tie, and shirt. He opened up his belt and stepped out of his pants. He left it all in a half folded pile by the door and put on his bra... the one he hadn't dared wear as it was just too hard to hide under a white dress shirt.

Dressed, or undressed, He climbed up onto the table. His phone is propped up, set to take a photo every five seconds, and so he began to pose for it, and for Master.

He knelt, legs spread. He caressed himself, running his hands over the lingerie.

He turned and raised his ass, moving to all fours. He arched his ass out, and lowered his head down, raising his panty-clad ass higher in the air. He reached back, to tug the panties aside, to show off the base of the plug buried inside him.

"Well, I wouldn't have fucking believed it if I hadn't seen it," a voice bellowed from behind him.

Rob felt the blood rush to his head as he jerked his body around. There in the doorway was Michael James, one of the project leads on his team. Rob tried to cover himself with his hands, but was useless. His clothes were on the floor at Michael's feet.

"It's... I can explain... I'm sorry..." Rob rambled and mumbled... scrambling off the tabletop and wrapping himself with his hands.

"Oh this is just too fucking rich. I can't wait to hear that explanation."

It was only now that Rob realised that Mike had his phone out, and was recording everything. Who knew what images he'd already recorded. He stood there, frozen.

"I thought there was an explanation? Well, go ahead. Explain." Micheal actually moved to put a foot on top of the pile of Rob's clothes.

"Come on... just let me get dressed and we can talk."

"Fuck that. In fact, get your hands down, and give me a few more of those sexy poses. Otherwise all of this gets emailed to HR right now."

"Come on..."

"I'm going to count to five..."

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Rob gave in, feeling totally defeated and terrified. He dropped his hands to his sides and posed, showing himself off from head to toe.

"Good boy. You know, you're not half bad like that. I think you're made to look like that," he laughed. "Turn around, show me some more."

Rob turned and posed again. Mike started to give him instructions, telling him how to pose. To put his hands on his hips, to raise one heel, or to bend over.

After an eternity, Mike tells him that it's enough. He throws his clothes over at him. Rob quickly gets dressed, not even taking time to take off the bra.

Once he's finally covered up again, Rob finally feels a bit more like his old self.

"Listen, Mike, are we okay? There's no need for anyone to know about this, right?"

"Well, there's no reason, as long as you do what I fucking tell you to."

"What... what do you mean?"

"I would think that's pretty simple, but I'll try to lay it out for you. I own you. You're going to do what I want, whatever I want, or I'm going to use these photos to end your career and probably your life as you know it. But it's not that bad. If you do what I tell you, if you're a good little sissy slut for me, then I'm going to be the best friend you've ever had."

"What... What do you want from me?" Rob stammered.

"No need to worry about all that right now. I've got plans, but you'll find out about them all soon enough. For now, why don't you get your slutty ass home, and I'll see you tomorrow."

Mike turned and left with a satisfied laugh.

Rob finally realised that his phone was still sitting there, taking photos. He sighed and picked it up. He sank into a chair and looked through them.

He finally got the energy to compose a message to Master.

"Master, something terrible happened. I got caught taking the photos for you."

He wasn't even done typing the next message, when Master replied.

"Send them. Now. Then tell me the rest."

In a daze, Rob selected all the photos from before his discovery and sent them off.

He continued to type then.

"This man from my work, he found me and he took pictures of me. I think he's going to blackmail me or something."

"Did you like that?" was the reply.

"No... I didn't want that at all. I wanted to take these photos for you, but I didn't want to get caught. I didn't want to ruin my life or lose my job."

"But you still sent me the photos after that?"

"Yes. Because I trust you. Because I have known you here for months now."

"I'm glad. I'm glad you trust me. Good girl."

Even now, those words made Rob smile.

He got the notification that Master was sending him a photo. Soon enough, it came through, clear and bright. It was a photo of him, bending over, his hands on the boardroom table, showing off his ass. A photo taken by Mike.

"Now, be a good girl and go home like I told you to. Tomorrow is going to be a big day for you. -- your Master, Mike."

His mind felt like it was melting, and he just couldn't decide how truly and totally fucked he was.

Chapter Two

The ride home was a daze, and Rob didn't sleep much.

He didn't have a clue what to do. It was late by the time he got home and for the first time in forever, he hadn't logged in once he got there. He couldn't get over how his Master was Mike, and had been all along. Had he been watched this whole time? Led down this path... and now what was he to do?

Eventually the clock meant he had to haul himself out of bed, into the shower, and to make his way to work. He paused while getting dressed. By now, dressing panties and stockings under his work clothes would have been a given, but things were different now.

Overnight, he'd come to think that maybe the fact that Michael was the real face behind Master wasn't the worst thing. At least it meant that he'd been into some of this. He wasn't just some man who was disgusted by what he'd discovered. With that sliver of hope, he chose a red lace thong and dark thigh-high stockings, then finished getting dressed.

It was hours before Robert finally heard from Michael. Just before noon, there was a message on the inter-office messaging system, asking Rob if he'd like to get lunch. It all looked normal and professional, as it should on the monitored forum, but Rob knew that saying no wasn't an option.

Precisely at 12:30, Rob arrived at the designated cafe, just a block down from the office. Michael was waiting. Rob walked over and was about to sit down when Michael stopped him.

"First things first. Go to the washroom and take a picture that shows me the panties you've got on under there. Then you can sit down."

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Rob paused, but decided to comply without argument. It wasn't like one more photo was going to sink him further. It took only a moment, and then he was back and given the okay to slide into the booth.

"Good sissy. It's a good habit for you to get into, to just obey without hesitation or complaint. I trust you realize just how fucked you are. I clearly have all the photos you've ever sent me of you dressing up in lingerie or posing with toys and all the rest of it, which is potentially very embarrassing for you. The photos from last night, of course, are what really take things to a new level. You being a little pervert in the middle of the main boardroom is more than enough to get you fired from this job, and keep you from ever getting another job anything like it. You understand that, right?"

"Yes, I understand."

"You understand, what?"

Robert blushes.

"I understand, Master."

"Good sissy. I'm not going to mess around, or beat around the bush. I intend to have you as my plaything. My sissy slut. Just like you talked about wanting so much. But instead of this just being some fantasy for you to stroke to, I'm going to make it real. Real in the way that I want, as your Master and owner. Sure, you have a choice to say no, but that choice will have real and very painful consequences for you. I am not at all above ruining your professional and personal life. The photos will go out to HR and everyone in management at the office, as well as your family and friends and your ex-girlfriends, just for fun."

Robert swallowed and took a deep breath. It was almost impossible to think with the sensation of his heart pounding in his ears and the feeling of his life crumbling around him.

"Do you agree, right here and right now, to be my good sissy slave, Robert? Will you obey me totally and completely?"

"I guess I don't really have any choice, do I, Master?"

"You have a choice. Your choice just has consequences."

"Yes, Master. Yes, I agree."

"Good. Your new life starts immediately. When you go back to work, I have a few things to set up, so I will require your keys and your wallet. You will also send me the passwords for your computer and email accounts at home."

"What do you need all that for, Master?"

"Sissy, it isn't your place to ask questions. You should just focus on obeying and making your Master happy."

He sighed, feeling the air let out of him again. He reaches down, fetching his keys and wallet out and sliding them across the table. Michael just smiles, pulls at $20 out of his wallet and then tucks them away.

"That should cover lunch for you. I've got some work to do. You can come home any time after 6:30."

With that, Michael slides out of the booth and departs. Rob just slumped into his seat, sent off the demanded information, and found something on the menu he could afford.

The afternoon dragged on and on, seeming to last forever. All Robert could think of was trying to imagine just what Michael was up to. When he finally did male his way home, he realised that his humiliation included having to get buzzed up from the lobby of his own building.

His heart was pounding as he made his way up. Michael swept the door open and invited him in. The changes were immediately evident, as even the furniture had been rearranged and changed.

"Welcome to your new and improved home. First of all, you'll notice cameras in every room. I want you to realise that I'll always be watching, ensuring your obedience."

Robert looks around, seeing the new devices in the high corners of the rooms, all around him.

"Secondly, regarding your wardrobe. I've discarded your remaining 'male' underwear. You are no longer permitted to wear anything but panties and stockings. You will wear them at all times, weekdays and weekends. When you are home, you will wear only lingerie. I want to see you around her looking pretty. That means a bra as well. You will also be wearing makeup, but you'll start with just lipstick, until you get the hang of more."

He looks around, using the updated settings to focus his instructions.

"Your lipstick is in the washroom. You'll also find Nair in there, as well as some ladies razors. You're going to be making sure that you are hairless from the neck down from now on. There are also some new toys in the medicine cabinet. I know you've gotten used to being plugged at times, but that is going to be every work day now. Your new plugs also have a wonderful feature that will allow me to trigger their vibration from anywhere. In fact, why don't you head in, strip out of these outer clothes, and get your plug in. I'll wait."

Robert's time in the washroom at least allowed him a moment of privacy to let this sink in. He stripped and adjusted his stockings. It wasn't that different from what he'd done before, he thought. He'd pretty much given up on anything but panties anyways, and he was mostly just in his lingerie when at home anyways. Now it was just maybe a bit more, with the knowledge of being supervised.

The new plug was certainly larger, but he managed to get it in with the help of lubricant and patience. He took a deep breath and returned to the living area.

"Excellent. What a pretty little slut you are. I'm proud of you this way. One more way I'm showing that is that I've removed your blinds. I want you on display. Do you have any questions so far?"

Rob thought for a moment... but he really couldn't think of a thing to say.

"Wonderful. So, for now, your life will mostly go on as it has before. It is just that your Master is taking a bit more active control. This isn't just fantasy anymore, and I'll be watching to make sure you understand that. The punishment for disobedience isn't going to be some playful spanking either."

"Yes, Master," he replied, signalling his understanding.

"Good. Now, I've got one more thing to help you with."

Michael moved and pulled out one of the dining chairs and set it in the middle of the living area.

"Have a seat," he instructed.

Robert sat down, a bit nervously.

Michael moved behind him and guided his wrist behind the back of the chair, and then handcuffed them together.

"What's happening?"

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