Revealed to My Roommate Ch. 01

Paul watched the clock on the office wall with rapt attention. He'd finished his work hours ago, the truth was doing the minimum at this dead-end office clerical job didn't take more than a couple hours of hard work a day, and since then he'd tried everything to distract himself. He'd been to the water cooler a suspicious number of times, taken several bathroom breaks, made the round of the cubicle and even stepped out with the smokers. Thirty minutes ago he gave up on distracting himself and settled in for a good stare at the clock.

It had been a long day, really every day at work felt like a long day and every Friday, like today, felt even longer. Most folks were excited about weekend plans or going out as a group, like everyone else in the office seemed to be planning too tonight. Paul had been invited by several folks but had turned down every offer. He had other plans for the evening. Plans that arrived in his email inbox about 10am and had made the day drag by even slower than usual. He'd gotten an email from HER.

You see, Paul had never been much of a ladies man, he'd been on a few dates and made out with a few of them, even having a couple of unfortunate and unsatisfying sexual experiences. Paul had, like many unfulfilled young men, turned to porn. And there, he found a wonderful panoply of experiences. He'd watched incest, interracial, gang bang, lesbian and fetish, but he'd really discovered himself when he found femdom humiliation videos. At first, he'd watched some of the stuff with porn actors in it, but it was the POV videos that really changed things for him. His interest in other forms of porn dried up like a creek during a drought and he searched for the newest and most exciting videos. And then, one day, he happened upon his first video of HER: Jane St. Claire.

By the time he saw the first video Paul had become a connoisseur of mistress videos. He could usually tell from looking at a new face if he'd enjoy the tone, the set-up the acting work and the plots the domme would come up with. Seeing Jane St. Claire for the first time, a still image on Clips4Sale advertising her new studio, he felt a buzz start inside him mirrored by a hardening down south. She had dark brown hair and light, even pale skin. She had thick lips always covered in red lipstick and dark searing eyes. Hey breasts were a full and round 36 D and she had a lovely perky ass. She always wore matching lingerie, usual bras with full cups and thong backed panties.

Paul quickly bought a selection of videos from her - SPH (small penis humiliation), JOI (jerk off instruction), CEI (cum eating instruction) and sissy training were his go-to categories and for a new domme she already had several up. Over the next several months he bought almost every new video she put out and then, for the first time ever, he sent in a request for a custom video using his name. She delivered and he followed up with another request a week later, two the week after that. Miss St. Claire, as he'd taken to calling her, even in his head, ate up most of his disposable income but Paul didn't care. And then, something amazing happened; when sending one of his custom videos she asked if he would like to chat sometime.

He quickly agreed and later that week they were chatting on discord. She explained that he was her biggest supporter and that she just wanted to know more about him so she could make the videos he was ordering more enjoyable. After this they fell into a bit of a pattern. Paul continued to pay for videos and for items off her wish list on Amazon. She would email photos of clothes he had bought her and items decorating her house he had purchased. As they got to know one another better Miss St. Claire began challenging Paul a bit. She used the videos to give him direct instructions, he rarely bought generic clips anymore he so loved hearing her say his name- not Paul, but the name she had given him: Prissi.

"Prissi sissy," she would say, her voice making the hiss of the 's' sounds send pleasurable waves through his body. Miss St. Claire knew he had a selection of panties and underthings he had bought online. She soon insisted he must buy some in person. The first time she let him do it quietly, without making a fuss. Then she made him return a pair he had bought that didn't fit correctly and ask the sales woman for help. The woman he'd run into first nearly had a fit when he asked but he was saved from her wrath by another clerk popping up and offering to take care of it. Marcy, he discovered her name was, delighted in the task set before her. That first time he shopped with her they took a deliciously humiliating tour through the delicates selection before she let him slink away with his purchases. That evening, Miss St. Claire had him recount the entire thing for her before insisting he video himself telling the story and send it to her so she could listen to it over and over again as she plotted his next steps.

This became part of their pattern, a piece of the game. He would complete her challenges and then come back and report on them to her, sometimes she'd even masturbate while he watched or command him to do the same. Always, he had to record a video afterwards retelling the story (usually with some requirements to highlight certain sections or explain certain details) so that she could file it away. He sat in front of his computer wearing a matching pink bra and panty set and a face full of makeup as he described asking the woman at a Macy's to help him choose foundation and then a full kit. He modeled women's clothes she sent him out to buy, a variety of garments from the practical to the obscene. He had a chest full of women's costumes for Halloween - again ranging from sexy nurse or maid to a quasi-professional set of Disney princess dresses. He had leggings and sports bras, skirts and heels. Then she'd decided to step up the challenge again.

He'd bought several videos of dildo worship when he first came to find Miss St. Claire but never ordered a personal video with that focus. She once inquired why and when he explained he didn't own a dildo she gasped, "Well, that won't do for a frilly sissy like you!" And there was the next challenge. He drove nearly a state over before he went into a store, and he bought 5 different kinds of dildos, various sizes and colors, to make sure he had one his mistress would accept. After the purchase she, of course, wanted him to test them out, all while she watched and laughed. Soon he was deep throating dildos and even riding them on occasion. Recently, she'd had him cum on one and lick the cum off.

Through all of this Miss St. Claire always kept pushing him, she searched out his deepest darkest fantasies. He knew very little about her but she knew a whole lot about him, she might have known him better than anyone else on the planet. And, like he had an extensive library of her videos, she had plenty of him too. The most recent chapter of the game had been all about blackmail and this video was meant to be the payoff piece. This morning the latest custom video he'd ordered had arrived. He'd been instructed to go home and watch it there - that there would be a package waiting for him on his arrival.

The clock finally ticked over and Paul leapt out of his chair and nearly sprinted down the hall. He tried to control himself going down the stairs but ending up taking the last flight two and three steps at a time. Getting to his car he forced himself to take deep breaths, he couldn't afford to get a ticket right now. Breathing heavily he navigated his way home and finally arrived at his house. Well, he and Dean's house. His roommate Dean was a co-worker and the primary organizer of events like tonight's all staff bar crawl. They'd started at the office at the same time but Dean was a rising star while Paul was stuck in place. Dean was gregarious and popular, outgoing and charming. Paul was generally just there. Or not, as the case may be. He tended to avoid those crowds of people.

Where Dean was tall and fit, Paul had always been short and slender. His mother often referred to him as petite, one of many reasons Paul spoke to her as rarely as possible. Paul worked out at home, mostly cardio aerobics assigned by Miss St. Claire, so he was actually in pretty good shape. That shape just happened to lean decidedly feminine. He had always had wider hips so as he toned his body and 'blasted' his ass, as one video politely put it, he ended up with a very lady-like lower half. His topside would have been lady-like but was missing two very obvious pieces to that puzzle. However, his back and stomach also looked feminine. His long blond hair was one more challenge from Miss St. Claire. She delighted in requiring him to wear it fully down or in a high ponytail. He'd learned a number of ways to style it as part of a challenge, even able to braid it while deepthroating a dildo, a skill he didn't expect would come in hadn't.

Tonight, Paul was just glad the bar crawl meant Dean wouldn't be home for hours. He hustled to the front door and scooped up the package with his name on it. He didn't open it, former experiences had taught him that Miss St. Claire would bail if he broke her rules and then the night would be wasted. He logged into his computer and pulled up his email and downloaded the zip file she had sent him. It extracted into a word file and an executable file. He opened the word document first.

Paul,

This is a new game for us, I hope you trust that I always know what's best for you. If you don't run this piece of software then you'll never hear from me again. If you do, the game goes on forever. Before you choose, open the package you received and read the letter.

Miss St. Claire

Paul felt his erection blossoming in his panties, yellow cotton bikini style with pink dots. She'd had him wearing panties all the time for months now. He tore open the package with his nails, slightly longer than most men's, probably not noticeable unless one really looked, complete with a natural manicure. Inside he found an item he had been longing and dreading in equal measure - a pink chastity cage. This one was not plastic like most he had seen online however, it was metal. It looked absolutely real and like it would be impossible to get off. He saw a card inside with a small padlock attached. He opened the card:

Paul,

The key is not in the box. It will be kept in safer, more reliable, more fun hands. So, my pet, put this on and lock it, then start the video.

Miss St. Claire

Paul pulled down his panties and got out his dicklet. He'd been forced to call it that so many times by Miss St. Claire that he thought of it that way even when he wasn't with her. She wasn't wrong, about this or anything he supposed. He couldn't call his meager one and a half inches a dick or a cock. It wasn't anything impressive at all, except for impressively small she once quipped. He slipped it inside the chastity cage, worried it would be instantly painful. Instead, the inside seemed smooth and while it was a snug fit it wasn't deeply uncomfortable. He ran the lock through the provided hole and, with a breath, locked himself in. Then he reached up and started the file.

As it began Paul realized instantly that something was different. Every video he had gotten before this was clearly marked as a domme's video - an opening package that included the scene title, the domme's name and website. This just opened on a place Paul recognized as Miss. St. Claire's apartment. He had a view of her office with her sitting behind a desk. Paul had long wished he could visit her and be laid out over that desk and spanked by her hand. Sadly, Miss St. Claire was incredibly sensitive about any personal information and so Paul had no idea where she lived. Another clue that something was odd is that his goddess was fully clothed. This wasn't unique, there had been other times when she would be dressed up to have something to take off but it was rare. And these clothes weren't a "sexy '' get-up. Instead, she looked like a woman who had been paying bills a moment before. As Paul wondered what was happening she began to speak:

"Oh Paul, my favorite ever fan. And, since I can now be fully honest, by far my biggest fan. I never wanted you to know that since I didn't want to give you any leverage -though you probably wouldn't have taken it anyway. You truly have been every bit as pathetic and malleable as I thought you would be the first time we met."

'That hurts a little,' Paul thought. She's said meaner things but always as part of a game. This seemed different somehow.

"Now, you couldn't have known this, but being a domme has never been my only iron in the fire. In truth, I have had several paths set up to my ultimate desire, relaxation and wealth. And, while it would have been nice to keep you paying away it turns out a different ship has come in for me."

With that, she held out her hand, showing off a truly immense engagement ring.

"I now, I never mentioned I was seeing anyone seriously. He, of course, knew about you - honesty is important in relationships. He was fine with all this in a girlfriend - the losers longing after something they couldn't have actually built up his ego a bit I think. But, he wants something different from a wife, and so it is time we say good-bye."

Paul blinked, unable to fully understand what she meant by all this.

"I'm serious Paul," she leaned into the camera, "after this you won't ever hear from me again. Hubby and I will be off, and we will part ways. But, as I mentioned in my email- our game doesn't have to end because our relationship does." She leaned back and a dark smile covered her face. "You see, Prissi, I've learned so much about you over the past year. And, I thought it would be a waste for you to have to start all over with a new domme - it would take them so long to get you this close to where you need to be. You might start back sliding, thinking that pathetic little dickelt was good for anything other than producing cum for you to slurp up by the handful. No, I couldn't let any of that happen to you. So, I made a plan. I started our blackmail game and found out lots and lots about you - including your roommate's contact information. I thought you would find that a stranger detail than you did, but i suppose one dildo down your throat and another in your ass served as enough of a distraction."

Paul stared ahead in shock, his stomach beginning to clench in fear as her words unfolded.

"You always said that you had a blackmail fantasy. That someone close to you would find out your sordid little secrets and have fun with it. Well, as a last give, or a last fuck-you depending how you react to all this - I can make the frist part happen. When you opened this file a notice was sent to another account to send a link to Dean, yes, your Dean. By the way, I looked him up on Instagram and he is even better looking than you described. I think he'll be perfect. Now, there is a chance he doesn't act on any of this. In which case your key will be delivered in a week and you can go on with your life. But, there's a chance he follows the link I've sent and finds every video you've ever sent me and decides to make you live out all your fantasies for real. So, Prissi, you just have to ask yourself one question: Which one are you hoping for?"

And like that the file ended. Paul was having a bit of trouble breathing, 'This has to be a joke,' he thought. He tried to send her an email but got a bounce-back notice. He visited her online pages: clips4sale, myfans, even twitter, everything had been purged. Paul felt tears welling up in his eyes, his emotions overwhelming him and he brought his hands to his face and cried.

Over the next several hours Paul would go through cycles. He'd cry for a while, then take deep breaths and tell himself to get it together, he'd the try to come up with a plan to solve this, he'd devolve into random internet searches - "how to deal with blackmail", "cracking an email password", "removing a chastity belt". Each time he found nothing very helpful, and on the last one nothing that didn't seem pretty painful. Then, he'd be back to crying. He finally fell asleep several hours later, having splashed water in his face and brushed his teeth. He didn't know what he would do tomorrow and the most frightening part to him was that as he cried himself to sleep he was as hard as he could get in the chastity cage.

--

Paul woke up the next morning after a rough night of sleep but with a sense of hope, 'Maybe this is all just part of the game,' he thought. It was possible, after all, that this was just the next step in the intense game he and Miss St. Claire had been playing for years. The tug of his chastity cage, and something deep inside him, told him otherwise, but he held onto that hope. He cracked open his door to visit the bathroom down the hall and didn't notice anything different. Saturday morning seemed like any other. He visited the bathroom and the only change he noticed was the cage on his penis required him to sit to pee. He imagined that the key might arrive in a couple of days and this might all be over. He promised himself not to get so involved again online.

He walked back to his room and noticed Dean's door was closed. So, he'd come home last night and nothing unusual had happened. Okay, that was good. He threw on some sweats and a t-shirt in his room and went to the kitchen. He toasted a Pop-Tart and sat down at the counter to eat. A few minutes later he heard Dean's door open and froze. His roommate walked into the room, only wearing boxer briefs, his hair a mess and eyes squinting against the light of day. He grabbed a Pop-Tart and took it, un-toasted, back to his room, a single grunt the only evidence he even noticed Paul sitting there. As his door closed again, Paul let out a breath he hadn't even realized he was holding. He pulled out his phone and tried again to email Miss. St. Claire to see if it all had been an elaborate joke. The email still bounced back. And yet, it had been more than twelve hours, Paul glanced over at the oven clock, closer to 18 actually, he'd slept late after being unable to fall asleep, and nothing had happened. Maybe it all was a cruel joke.

Paul knew he had to occupy his time somehow so he went to his room and went through his normal wake-up routine. If his mistress suddenly reappeared she would ask if he had completed his tasks. He used teeth whitening strips to make sure his smile was perfectly white, applied his facial cream, checked the manicure on his fingers and touched up the polish, pink of course, on his toes. He showered and both shampooed and conditioned his hair, the tradition on Saturdays, and then put it in a bun upon his head. He pulled on a purple thong and then some jeans and a t-shirt and headed out of the house to get some groceries.

The trip to the grocery store helped Paul relax. He felt more and more confident that everything was just fine, the normalcy of the store reinforcing his surety that the world was just as it was supposed to be. He was only picking up the necessities today so he didn't take too long. While waiting in line he picked up a Cosmo, part of his "public humiliation ritual" for Miss St. Claire and leafed through the pages, paying special attention to any articles about "Pleasing Your Man" as he had been instructed. Packing up his groceries, he headed home.

He'd unloaded the groceries and put everything away when his world came crashing down. As he walked back down the hallway to his room he noticed first that Dean's door was closed, but then he noticed a sign on his own door. Moving closer he froze as he saw that it was a handwritten note that read, "Waiting for Prissi". Below those words he read:

Put on the clothes laid out on the bed and come crawling into Daddy's room