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..."