Daphne Rosen's Bitch Ch. 05

I was all alone in Mistress Rosen's mansion with nothing but my thoughts to keep me company. After I'd laid out her lingerie and dress she'd dismissed me from the bathroom, telling me to return to my room for the evening. I heard her moving around, and I imagined her wearing the lacy couture lingerie she'd bought herself with my credit card, and walling around in the skimpy clubbing dress I'd chosen for her, but I didn't see her again. Then she left me.

She'd never mentioned a boyfriend before, and I had kinda just assumed that we were exclusive. I mean, she'd said we were in a relationship, but I guess she never actually called me her boyfriend. Maybe it was just a casual thing with this guy? But she had said she wouldn't be home today, so did that mean they were... fucking? But casual sex doesn't mean as much as a committed relationship like ours. And to be fair, she let's me fuck around with lots of men and women, so it's not like I'm being one hundred percent exclusive either. Well, maybe I'm not exactly fucking them, I thought as I rubbed my aching clitty through my cage, but my mouth is getting tons of action. And maybe now that Mistress has popped my cherry, she'll let me take men's cocks in my ass too?

My ass. Thinking of it brought an avalanche of feelings down on me. Mistress Rosen had fucked me. I mean, she had really fucked me. I reached a hand back, popping out my plug and fingering myself as I remembered it. The way she'd forced in inch after inch. The way she'd pressed my face down, forcing my ass high in the air. The power of her thrusts, sending shuddering waves of pain and pleasure through my body. My fingers weren't enough. I needed something more.

I'd been allowed to bring so little, it only took me a moment to find the dildo Daphne had bought me. It was maybe a bit smaller than her strapon cock, but it would do. I balanced it on the floor of my room and lowered myself onto it, sighing with satisfaction as it slid deep within me. I lifted myself, then squatted back down even deeper. Before long, I was bouncing up and down wildly. My hands roamed over my body, trying and failing to simulate my flopping caged clitty, before settling in on my breasts. My nipples had grown so tender lately, and as I rolled them between my fingers and began to experimentally pinch them I found new avenues of pleasure opening before me.

Frustratingly it wasn't quite enough to bring to climax, but it felt good nonetheless. I knew that girls didn't always orgasm, at least that's what I'd read online, so maybe that was okay. Eventually I grew to tired, so I laid on my side in my bed with my dildo still stuffing my backside. With a pillow behind my back it almost felt like I was being spooned, so I didn't feel so alone. I reached behind myself to grab the base of my dildo, slowly fucking myself to sleep as I wondered what my Mistress was doing.

The next morning I rose and set about preparing for my day. Daphne didn't look to have come home in the night, so I found a shower, cleaned myself up, and got dressed for our morning yoga class, hoping I'd see her there.

My spirits lifted when I entered the studio and saw her standing there, surrounded by a few of the other women listening to her tell a story. She was positively glowing, and I listened eagerly as I approached.

"...not too serious, but a girl's gotta get laid, right? And let me tell you, he could really lay some pipe. I mean, he was..." she looked up and made eye contact with me as I got close to the circle. "Well it's about time you showed up, Brandi was wanting a pre-workout warmup, and class is about to start. Chop chop!"

I hurried over to Brandi, rolled down her yoga pants, and started in on eating her ass, trying to hear the rest of the conversation over her contented moaning and occasional instructions, and managing to catch snippets.

"really knew how to hit all the right spots"

"nickname is Rod"

"hours and hours"

"of course I let him go there"

Ask through class as I was passed from client to client, I heard bits and pieces. Apparently her date had gone well. Really well. So well that they headed back to his place early. And then it has apparently gotten even better. I knew from watching her videos that Mistress Rosen had a thing for big dicks, and from the sound of it she'd taken full advantage of this one last night. I was... happy for her? Being in a relationship meant wanting your partner to be happy, right? And she'd looked positively radiant this morning. Whatever 'Rod' had dinner for her had clearly made her very happy. I tried to hold onto that thought instead of thinking back to my evening cuddling with a pillow and my dildo. Finally class ended, and I forced a smile as Daphne approached me.

"Did you miss me last night? Well come on bitch, I really need a good cleaning this morning."

I followed her back to the bathroom, where she stood waiting for me to kneel in my usual spot in front of the mirror.

"I'm waiting. Are you going to let me sit on your face, or do we have a problem here?"

"No problem Mistress Rosen, " I replied quickly. "It's just, did you and your... your..."

"My boyfriend?"

"Yes, your boyfriend. Did you two make love last night?"

"Make love? Did we make love? What is this, a medieval romance? No, we fucked. All over his apartment."

"But, I thought that. Aren't we in a relationship?"

"Of course we are. I'm your pimp, and you're my sweet little bottom bitch. Who's supposed to be cleaning my ass right now, not asking me inappropriate questions about my personal life."

"I just thought that maybe I was your boyfriend?"

"You? Are you fucking kidding me? Look at yourself. Really take a good hard look. You're a sissy girl. You're a nice set of tits and ass that can't keep cocks out of her mouth and whose limp little clitty is locked away because it could never satisfy a real woman like me. Now, any more issues you'd like to bring up?"

"Did you shower after you and your boyfriend.... I mean... I can't."

"Seriously? That's what your hold up is? If Rod was here right now you'd be begging me to let you suck his cock and swallow his cream. But don't worry slut, I saved some for you."

Daphne pushed me down to my knees and rolled down her yoga pants and panties. As she did, sticky tendrils of splooge stretched from her body to the crotch of her panties. Before I could protest anymore she grabbed my ponytail and forced my face into her, grinding up and down, smearing my face with a mix of stale cum, pussy juice, and sweat. I tried to hate it. I tried to stand firm and not enjoy licking up the leftovers if another man having sex with my divine Mistress. But I failed. In under a minute I was lapping eagerly at her ass and pussy, trying desperately to suck out every drop.

After that I never questioned my Mistress' other relationships again. If she was happy, then I was happy. I just hoped that she'd never decide that she was done with our relationship. I tried to make myself useful around the house, cooking and cleaning and always making sure she had what she needed, at least when I wasn't working. Whenever my chores were done Daphne would let me serve her in more personal ways. Giving her massages and pedicures became common, and when she was watching a movie or browsing Tinder she'd often let me eat her ass or pussy as long as I wasn't too distracting. But the best was after her dates when she came back and let me clean her holes while she told me about everything they did together. All those other guys thought they were on the inside track, but little did they know that in the end I was the one she always came home to.

Of course, the other thing we did was train my ass. I asked Mistress if she could find some clients to really fuck me now that she'd claimed my anal virginity, but she insisted that as my pimp it was her responsibility to make sure that I was really ready to give my clients a high quality fuck before she could allow that. So every day she made time to put on her strapon and ride my ass. She put me through every conceivable position, pounding my prostate from every angle, but I found that my favorite was always the classic doggystyle, just like our very first time.

Our anal training sessions were also the perfect time to get in my audio training. Mistress bought me the cutest set of pink headphones with fuzzy cat ears on the top, which was perfect because every time I put them on it made my brain feel all pink and fuzzy too. Mistress' sweet voice echoed in my empty mind, coaching me on how to squeeze and open my pussy in time with the thrusts to give my partner the most pleasure possible. At the end of each session, Mistress would heft my violet-jeweled plug, the largest in the set she'd bought me, and try to seat it in my gaping ass. It took weeks, but one day as she pressed down on it with enough force that I thought I'd split in two, it finally went in. I stood, balancing unsteadily from the sheet mass of steel filling me, then looked up at my Mistress with pride.

"That'll do, slut. That'll do." She said with a broad smile. "I'll see if I can't find someone willing to take your ass for a spin now."

The next day at the coffee shop I made my way to the back room where I did my business and waited. I hoped Mistress would find me a good man to give me my first real cock in my ass. Someone handsome, and hung, of course. And I wanted it to be romantic. Mistress Rosen owned me, body and soul, but a girl could dream about a strong, tall man sweeping her off her feet and making tender love to her secret place. Someone like...

The door opened, and in walked Steve. He was the one! It was just like I'd dreamed, Steve and I would make sweet love and...

Behind him man after man stepped into the room. I recognized them as many of my regulars, and by the time the last had shut the door behind him there must have been nearly twenty. I gulped nervously. I'd wanted a real man to fuck my ass, but I'd thought it would be something special and intimate, at least for my first time. Just Steve and his strong, gentle hands, bending me over as he slid his meat into my eager backside.

"Daphne said you had something new on the menu," Steve said as he approached. "It seemed only right that I get the first taste."

He spun me around and bent me over the table, his touch gentle, but irresistible. My skirt was so short that bending over exposed my entire ass to the roomful of eager men, showing no panties, just a purple-gemmed plug embedded in my plump ass. I panicked at first as he pulled on it, clamping down hard. But Steve leaned in and whispered in my ear, telling me that he knew I wanted this. I breathed deeply and relaxed, allowing him to force the behemoth out of me. I felt him maneuver into place behind me, firmly pinning me in place with a hand on each hip, and I held my breath in anticipation of what was to come.

Steve's first thrust hilted all seven glorious, warm, throbbing, veiny, living, pulsating inches of his cock fully into my sissy pussy. The air was blasted from my lungs by the force of his impact, as my well-stretched ass needed no warmup before handling any man alive. As he started to pump in and out I could hear Mistress' voice in my mind, directing me to squeeze and release on his cock at all the right times to make it feel like I was sucking him into me and trying to never let him go. With my body pinned to the table by his, Steve's hands moved up from my hips, tracing along my sides until he was cupping my sensitive breasts, squeezing and kneading them under his strong fingers. It was too much, and I felt a warmth within blossom into an earthshaking orgasm. My convulsing ass was apparently too much for Steve too, because at the same moment I felt the delicious warmth of him depositing his load deep inside me.

I wanted to lay there forever, or at least until Steve was hard again and ready for another round, but he stumbled backwards and in an instant a fresh cock filled me. My moment was gone, and my dream of a romantic first time was dashed, but with a cock in me I couldn't resist my Mistress' voice instructing me to use every tool she'd given me to give him the ride of his life. Man after man stepped up behind me, and man after man deposited his warm, salty cum in my eager ass. I lost focus, and lost all track of time, continuing to milk the cocks inside me by sheer instinct and muscle memory. Finally I must have satisfied them all, because I felt Mistress Rosen's unmistakeable touch as she spread my ass and reinserted my plug.

"Wouldn't want your hard-earned reward to drip out, now would we? What do you say to me for finding all these hard cocks to fuck your ass?"

"Thank you Mistress Rosen," I managed to murmur, barely coherent.

"You're welcome, bitch. And you made me a couple thousand bucks while you were at it, so I'd say it worked out okay all around."

Just then the door opened and another man walked in. It was my manager.

"Look," he said awkwardly avoiding eye contact with me, "This isn't working out. I know we had an arrangement, but you just can't work here anymore."

I was shell shocked.

"But, you said it was alright before! The customers love me, and I take care of you first thing every morning."

"I know, but it's just not working out."

"Is it because I let all those guys fuck my ass? Do you want that too? I'll let you. I'm really good, I promise!"

He looked genuinely torn, and from the corner of my eye it looked like he was making eye contact with Daphne, who was gently shaking her head.

"I'm sorry, I really am, but you're fired. Clean up and go home."

Daphne was so sweet, consoling me on the way home and assuring me that she'd find a new place for me to meet my clients. I just didn't understand why my manager had fired me, when it seemed like he really just wanted to keep our arrangement going. Maybe someone from HR talked to him. But whatever the case, I was now out of a job, and as Daphne reminded me I needed to do my fair share to cover my rent in her home.

"You know, I think I know just the thing for you. No need to look elsewhere for employment, you can start work as my maid."

"Your maid? Isn't that a little weird?"

"I mean, you already handle most of the cooking and cleaning around the house anyway, and technically your bedroom is the original servants quarters. Besides, I like the idea of always having you around in case I need you. Your place is here, in my home, at my side, and under my foot."

The thought was captivating. Mistress Rosen's personal servant, focused wholely on serving her.

"And as the cherry on top, I have the cutest little uniform for you to wear!"

There was no saying no to her, and in short order I was dressed in a classic, though particularly revealingly cut, French Maid uniform. Oh my goddess, it was so cute! I adored the little lace touches and the way it's flattering cut showed off my new body. Even better, Mistress Rosen seemed to appreciate it too. As I set about my chores she made a show of casual disinterest, playing the role of the haughty mistress of the estate, far above noticing the help. But when the bending and lifting that came with many of my tasks made my ruffled skirt lift above my plump cheeks, or have her a view down the low-cut top to my cleavage, she ogled me openly. Before long she had shifted her role from the haughty mistress of the house to the lecherous master, groping and swatting my ass at every opportunity. Finally she declared she needed to inspect the quality of my work, finding faults here and there which were handled with a disciplinary pegging, reminding me to be grateful that she was putting a roof over my head.

That night in my room while Mistress was off on her date, I imagined we were living in Victorian England, with her as the master of the estate and me as the poor servant girl. In my fantasy the domineering master gradually developed feelings of true affection for her servant, transforming their relationship from sex and servitude into budding love, finally culminating in marriage. One hand played with my breasts as I daydreamed, while the other tried unsuccessfully to play with my clitty under my skirts. Mistress still wore the key to my cage safely tucked between her breasts. She even said that some of her dates asked her about it. But she hadn't offered to unlock me in ages. So instead I caressed my tight little balls while squeezing the plug in my ass, imagining the powerful master of the estate taking me into her bed on our wedding night, making love to me not just as her servant but as her bride. Before long I had another mess to clean up.

While I loved the dynamic that came with being Mistress Rosen's live-in maid when it was just the two of us, things got a little trickier when others got involved. Daphne seemed to really enjoy hosting little get togethers for her friends and having me serve everyone. Inevitably what started as me serving tea and sandwiches turned into Daphne telling her friends all about how skilled of a servant I was, which turned into her friends asking her if they could take me for a spin, which turned into all of them watching and laughing as I was forced to put on a striptease, or serve them orally, or even lift my skirts and let them have their way with me as they borrowed Mistress' strapons. It was humiliating, and just didn't feel proper for a dignified servant. But serving my Mistress meant serving her friends as well, so I smiled and curtsied my way through it all.

Serving Mistress' friends also extended as to serving her boyfriends, as she started bringing them back to her place more regularly. At first I was just serving them drinks or dinner, popping in and out, trying to maintain my composure while watching their hands working their way up her dress. And seeing her eyes roll back as she ground herself into their exploring fingers. And hearing them kiss deeply. But Mistress decided that it was too much bother having to call me when something was needed, so instead she had me stand quietly in the corner of the room they were in at all times. And so I watched even more. Daphne fishing out their big cocks and sucking them off. Daphne climbing atop of them and guiding their throbbing meat into her pussy. Daphne crying out in ecstacy as they came together. Then they would leave, and I would do my job and clean up.

Something on my face must have eventually betrayed my discomfort, because Mistress eventually asked me if it was hard to stand there and watch her with her lovers. When I admitted that it was, she told me that she'd make it easier on me by letting me do more than just watch. The next time she had a man over, she waved me over while they were kissing, pulled out his cock, and put her hand on the back of my head, forcing me to blow him and get him ready for her. A part of me hated it, resenting that this man who would never love Mistress like I did was going to fuck her, but a bigger part of me was hungry for his delicious cock.

Ever since I'd started as Mistress' maid, I'd barely had a chance to see my old clients. She said that my first duty was to her, and that if I wanted to go whore myself out, I'd need to do it on one of my exceedingly rare days off. So while the blowjob started with Mistress forcing my head down, it ended with her pulling me off as I struggled to keep the yummy man-meat in my mouth as long as possible. After that I had no trouble with Mistress bringing her lovers over. It was so kind of her to share, and to let me suck on their cocks for her before helping her out while they fucked by supporting her legs, or licking her ass, or just cradling her beautiful head in my lap. Sometimes if they were the more adventurous sort, she'd even let her boyfriends fuck my ass.

All was well, until one day while cleaning the living room I saw a stack of magazines on the coffee table. Bridal magazines. I flipped through them in a panic. I could see in my mind's eye just how beautiful Mistress Rosen would look in a white dress, walking down the aisle to the luckiest man in the world. I wondered which of her lovers she had chosen and returned to my work, doing the best I could to stifle my tears.