Daphne Rosen's Bitch Ch. 01

She again ordered her usual drink, smiling broadly as I called her Miss Rosen, then took her seat. When I brought her drink over I thought she might have me sit with her again, but she instead ignored me. Unsure of what to do, I turned to leave and was shocked when a firm hand smacked and squeezed my butt from behind.

"Thanks for the coffee sweet cheeks, go ahead and put it on your tab."

I was mortified, but the rest of my shift passed without incident. When Mistress Rosen got up to leave my heart broke a little. I'd thought that maybe after being such a good boy the night before she'd let me out of my cage. It turned out that I drastically misunderstood our relationship.

That evening I came home to a new email with a new set of links to work though. I dutifully setup my webcam and my shot glass and set to work on my homework. Again video after video of my beautiful mistress in all manner of scenes blurred together, some new to me and what I could only assume were personal footage and others classics I'd masturbated to a hundred times. But like last night I never came, just oozed into my shotglass which I cleaned out between videos. The final link was to an audio only file with instructions to listen as I slept. As I slipped my headphones on I heard Mistress Rosen's soothing voice, praising me for serving her so well. After the firm instructions and domineering tone of her voice overlays in the videos it was like being wrapped in a warm blanket after trudging through a blizzard. I rested my head on my pillow, imagining that it was her lap, and swiftly feel fast asleep as her gentle voice continued to shape my mind for her purposes.

The next week continued in the same pattern. Every morning my beautiful mistress would spend a few hours in the coffee shop teasing me, and every night she'd send me a new set of homework. She came up with all sorts of minor humiliations to put me through while I was working. Any time I walked away from her she took advantage and either groped or swatted me from behind. I felt a sudden sympathy for waitresses back in the 50's. Sometimes she positioned a thumb to slide between my cheeks and prod at my cherry. other times she swung low and gripped my swollen balls, which made a perfect little target thanks to the cage she never let me take off. I knew I should be angry, but instead I felt flattered.

One day she turned her laptop around to show me what she was working on. I was shocked to see the view of myself in my webcam, staring vacantly as I tweaked my nipple with one hand and stroked my chastity cage with the other. When I slammed her laptop shut to try to prevent anyone else from seeing it, I knocked her coffee to the ground, spilling it all over. I held my breath, unable to believe what I'd just done and trembling at the thought of how my mistress might punish me. But she merely smiled at me like the cat who ate the canary.

"Well barista bitch, get down there and clean up your mess."

I dropped to my hands and knees, whipping the towel out from my apron as I frantically started to wipe up the spill. I was taken entirely by surprise when I felt her bare foot slide up my leg. Not daring to turn around, I could only try to stifle my moans as she slid her toes higher and higher and began to brush them against my aching balls and throbbing caged cock. Pleasure and pain swirled together intoxicatingly as she pressed hard, crushing my package against my body. I frantically worked to wipe up the last of it as her foot slid even higher and her toes began to prod at my ass. My cheeks parted for her as she began to force her toe into me. With a shuddering gasp that must have attracted the attention of the nearby patrons I came hard, pumping stream after stream of pent up cum into my pants.

She pulled her foot back then, sliding it back and forth through the cum seeping through my pants, torturing my sensitive cock.

"Hmm, I think you missed a bit on my foot."

I turned on my hands and knees and stared up at her, at the same time feeling like I was right where I belonged and wondering how the hell I had gotten here. I moved to wipe her foot off with my towel, but she viciously kicked it away.

"You'd use that filthy thing to clean the divine body of your goddess? No. Use your tongue you sad little bitch."

I'd like to say that I refused. Or that I at least hesitated for a moment. Or that I even thought about the small crowd that must have been watching the spectacle. But I didn't. I practically lunged at her foot, mouth wide open as I licked, kissed, and sucked every square millimeter of it with the fervor of a thirsting man in the desert finding water and the passion of a man on his wedding night. Her voice commanded, and I obeyed. I wasn't even ashamed as I savored the sweet taste of my submisson, I was thrilled. This was the first time she'd allowed me to touch her in such an intimate way, and the whole world seemed to disappear as I made love to her feet. Once I'd fantasized about sex with Daphne, of kissing her sweet full lips, or of worshipping her amazing tits or ass. But here on my knees I instinctually felt that I was right where I belonged. To worship my goddess' feet was honor beyond imagining as I could almost hear her voice in the back of my mind telling me over and over again.

I have no idea how much time had passed when she finally pulled her foot away. I was bereaved, and felt for a moment as if the light had gone out from the world. I felt like a puppy left home alone by its master as they'd gone out for work. The world slowly came back into focus as I looked up and saw hear beatific face beaming down at me.

"Sit with me, you've earned it."

I stood and reached for the chair across from her, but Mistress Rosen instead slid over in her booth seat and patted the space next to her. I wordlessly took my place and rested my head on her shoulder while she slipped an arm around my back. She opened her laptop again and began shopping online as she continued to rub my back and pat my head, periodically sliding her hand down to give my ass a little love-squeeze. I watched as she browsed through couture lingerie, marveling at the cost as I imagined what it would look like on her. Then she continued shopping for stranger items, including herbal supplements that promised to "make you cum buckets", a home enema kit, a set of sparkling jeweled butt plugs, and finally a large black dildo similar to the one I'd watched her masturbate with in her private videos. I was so engrossed in imagining her using all of her new purchases that I completely missed something she said, and could only stare dumbly as she held out her hand expectantly.

"I said give me your credit card barista bitch. After all, most of this shit is for you. And you should be happy to buy me some pretty lingerie. Maybe one day I'll even let you see me in it."

I handed her my card and tried not to think about how I'd manage the unexpected bill. She punched it in and finished all her purchases, but instead of handing it back she slid it down her cleavage, nestling it against the key still dangling there. The message was clear. Another piece of control had just been transferred into her tight grasp, and I doubted it would ever be returned.

"Well sweet cheeks you'd better get back to your shift. Don't be afraid to flirt a bit, you'll need to earn a lot of tips."

As she left I returned to work with the hardened cum strains on my pants mostly covered by my apron. I did my best to ignore the stares from coworkers and customers alike, thinking only of how sweet it would be to lose myself in my Mistress' voice as soon as I got home.

A couple of days later a few boxes showed up at my door. Mistress Rosen must have had tracking notifications turned on, because her email assignment that day told me to open one of the herbal supplement bottles and put it by my PC and to prepare the dildo as well. I obeyed, setting aside the remaining box and eagerly starting up the first video. When I came to it was dark out. The dildo wobbled in my hand as layers of drool ran down the thick shaft. My aching jaw and throat told me exactly where that saliva had come from, and I vaguely recalled that montage of videos I'd just watched of Mistress Daphne deepthroating monster cock after monster cock. I checked the supplement bottle and saw that it was nearly half empty. Surely the claims of quintupling cum production were just a load of hogwash. but I couldn't help but cringe recalling the price of each bottle and knowing that Mistress Daphne still had my credit card. My computer dinged as an email came in.

"I was so happy to see you take all your medicine and pump it down with a nice thick cock. Now you need to get ready for bed. Use the kit I sent you to get all cleaned out, then use the smallest plug. It's time we began training your body as well as your mind."

Although I'd never done anything like it before, I went to the shower and followed the instructions on the kit, washing out my ass until it was clean as could be. Then I inspected the butt plugs. they were each made from shiny metal and capped with a faceted glass heart. There were six in all, a rainbow that spanned from a dainty little red hearted plug up to a monstrous gleaming impaler nearly the size of my dildo and topped with a cute little purple heart. Taking the red plug in hand I knelt and instinctively lifted my ass high in the air. I couldn't help but think of Mistress Rosen's toes exploring my nether regions a few days before, and I tried to imagine that the cold metal plug was her soft warm toe as it slipped inside of me.

The next morning a new email instructed me to clean again and to wear my new jewellery to work. When she came in to the shop, mistress seemed to enjoy watching me awkwardly wobble around as I tried to get used to the relentless invader massaging my insides. Several times she signaled me to come over, pretended to have forgotten what she wanted, then squeezed a hand between my cheeks to fondle the jeweled cap. I couldn't help but squeeze down on it as she wiggled the plug in my bum, sending waves of unfamiliar pleasure up my spine. It was all I could do to stifle an audible moan, and the oozing strain that appeared on the front of my pants made me wonder whether those supplements actually worked as advertised.

Soon I grew more used to my new accessory, prompting a command from Mistress to upgrade to the yellow plug. I was surprised at how easily it went in after days of training with the red one, but I couldn't imagine that any amount of training would every coax my ass into accepting the largest of the set.

I wasn't sure if it was the supplements taking effect or the new plug pressing on my prostate as I ground my hips into my seat while finishing my homework, but it seemed like I was leaking more and more into my shot glass with every video. What had once been a dribble of clear precum was now a solid shot of creamy white. I never felt the release of an orgasm, but after each video I found a load of cum at least as big as those I used to pump out while masturbating had leaked from my caged dick. I was slowly becoming more attached to my dildo as well, associating it with the pleasure of watching Mistress Rosen and listening to her hypnotic voice for hours at a time. Feeling inspired, one night I tried pouring my shot of milked cum over the head before sucking it off. The next day Mistress giggled in the coffee shop as she loudly asked me if I'd enjoyed sucking the cum off of that big cock last night. Then in a quieter voice she instructed me that I should eat my cum that way from then on. I was utterly embarrassed and turned beet red as every eye in the place was glued to me. But I knew that in spite of my shame that evening I would be licking load after load of cum that dribbled out of my sad little locked up cock off of the dildo I'd been forced to buy for myself all because in one moment of distraction I'd called my crush my mistress and she had made it come true.

A few days later the next set of online purchases from my Mistress showed up on my doorstep. I tried not to think about my growing credit card bill as I rifled through the contents. My first thought was that there must have been some mistake. None of the shirts were long enough to go much past my midriff, the shorts were all super short, and beneath those there was a tangled pile of thongs. Then I saw the note at the bottom.

"Time to get working on earning those tips sweet cheeks. Try on your new uniform and sign in for your homework."

I was sure I'd look totally ridiculous, but I was still curious to see myself dressed in what Mistress Rosen thought would look good on me. After some struggling, I myself into one of the shirts. As I'd expected, it stopped a couple inches above my navel, but the right fabric did feel kinda sexy on me. Choosing to skip the thongs, I tried on a pair of shorts next. They were just as tight as the shirt and extended a mere inch down my thighs. The stretchy fabric wrapped tightly around me, prominently displaying my locked cock in enough detail that a close examination might reveal the metal rings. In the back I felt a slight wedgie as the seam slid between my cheeks, lifting my ass while also spreading it ever so slightly.

I walked over to the mirror to check myself out, expecting to look totally ridiculous, but to my surprise I was kinda hot. With my slight build I looked like a sexy twink. Or maybe even a tomboyish lesbian. The only thing that looked out of place was my boxers sticking out above and below my shorts. I turned from my reflection to pull out a thong to fix that, then suddenly stopped.

What was I doing? Sure, Daphne was a stone cold fox with the body of a goddess and an icy blue stare that pierced my soul, but what on earth did she have me doing? She had my credit card, was probably going to get me fired from my job with the scenes she kept making, had me licking my leaked out cum from a massive dildo, and for over a month she hadn't even let me have a proper orgasm. I'd always made fun of pussy-whipped guys, but at least they were getting pussy. I was gooning for hours each night without any chance of even jerking off. And now she was dressing me up like some femboy twink slut?

I slowly peeled off the shirt and shorts, dressing in my old clothes. I thought about pulling out my jeweled butt plug, but honestly I'd grown to appreciate the feeling of fullness as it constantly pressed against my prostate. Knowing that Daphne would see if I logged in to watch my nightly videos, instead I curled up in bed, hugging a pillow close to my body and trying not to think about what she had done to me. But night after night of routine had trained me like a dog. My balls ached, begging for even the oozing release I got from watching her videos. I looked at the pile of empty herbal supplement bottles, no longer doubting their effectiveness as my trapped balls were plump as plums with backed up cum. In desperation I tried humping the pillow I was holding, slowly at first but soon with frantic energy.

It was no use. Even imaging Daphne being there with me I couldn't squeeze a single drop of cum out without seeing her. My computer regularly dinged with notifications of new emails. I knew she must be wondering where I was. I knew that she was the only hope I had for relieving the pressure in my balls. But most of all I knew that if I gave in now I might never have a moment of lucidity like this again.

I lasted five more minutes before I leapt out of bed, frantically stripped down, and pulled on a thong, booty shorts, and crop top. Opening my email I saw message after message from Mistress, ordering me to turn on my webcam and get to work. When I finally switched on my webcam a notification instantly popped up inviting me to a video chat. When I accepted I saw my Mistress there on the screen, looking me up and down as she judged my new look.

"Was that so hard?" she teased. "You look like a real slut now, and a total sub. Don't worry, before long you'll feel better. Our outside should always match the inside, and it's time for the world to know that you're my bitch."

I nodded weakly, not sure how I felt about that, but immensely relieved just to be staring deeply into my Mistress' eyes once more. With a moan I felt the cum already starting to ooze out of me.

"Sounds like somebody is eager. Listen, I know I've been asking a lot of you, and I want you to know how proud I am of all the work you've done to please me."

"I love you Mistress Rosen," I sobbed out before I could stop myself. "I love you so much."

"I know you do, thank you," she said with a smile. "So tonight lets do something a little different. No links, no videos. Just lean back in your seat and listen to my voice..."

I remember very little of the night after that. I was so used to going into a gooning trance at the sound of her voice that I slipped under quickly. But this was a thousand times more personal. Instead of hearing her while watching her in various sex scenes, now she was right there, softly smiling as she told me over and over what a good boy I was, how hot I looked in my new clothes, how proud she was to be my Mistress.

When I awoke the next morning, my balls no longer ached. I have no idea how long it took through my cage, or how much of my own cum I'd licked off my dildo, but my Mistress must have spent hours helping me to ooze it all out. It made me feel so grateful to her as I slipped into a fresh set of my new clothes. She loved me, I was sure of it. I mean, she hadn't said it, but just look at how good she is to me. Maybe not quite as much as I love her, but she must love me, right?

Right?