Ms Dare's Femdom Anal Slut Pt. 01

"Stop fucking me around, Tom. It should have been done by now. It should have been done a month ago. I need progress on this by Monday."

Ms Dare slammed the phone down and looked at me.

"You. I'll see you once I've cleared this mess up."

I went back to my desk and killed some time while I waited for her.

Ms Dare was my boss's boss. She's an executive, significantly older than me. Back then I would watch her walk around the office, her massive tits bouncing with each high-heeled footstep. She caught me staring a few times, and she would always smile, her stern lips moving into a knowing red curl every time it happened.

And one day, we were in the lift together, and she said she wanted me to have dinner with her. I went to her place, a very nice place, and she ordered something in, and we talked and laughed for hours. She amazed me -- her mind swung and flashed from one thought to the next, her neat black hair fell above her textbook milf's body. I listened to her unrestrained abuse of the comically dysfunctional staff, always pretending to have done things that weren't done, coming up with excuses for why things weren't done, or taking unearned credit for completing something that they didn't realise had been done wrong. They were mostly good people, but they needed a lot of help.

We hung out about once every two weeks after that and it was something like friendship, but a friendship where you think about the other persons thick, mature thighs and huge breasts all the time.

After a while my phone buzzed: "All done. See you soon."

...

I drove to her place and knocked on the door, a bag of clothes etc under one arm. She had told me to stay at hers for the weekend since my apartment was being renovated.

When she let me in, she was still in her work clothes, but she'd undone a few buttons and my eyes lingered on her lightly freckled cleavage.

"Hey!" she rolled her eyes. "Come on. I'm starving."

We had dinner and as usual she vented about work.

"My days are getting busier. I'm spending too much time on stupidity. I need an assistant. In fact, I was thinking. I want you to do it."

I agreed very quickly.

After we ate, Ms Dare told me I could shower and change. I was sitting fresh and clean in a warm hoodie when I heard her coming from upstairs. I looked up and saw her foot make the first step, her robust calves tensed, and my eyes slid up to see her wobbling, thick inner thigh unconcealed by her robe. Just a glimpse, then she was halfway down the stairs, smirking at me then reclining at the other end of the couch.

We relaxed for a while, winding down for the night.

"You look tired. Come here," she motioned for me to lay in front of her.

I lay back, my head directly by her breasts as she lounged on her side. She continued talking about something, I don't remember what, but she soon fell into silence and my heart beat restlessly. I noticed she was watching my face and I met her eyes, then I looked away, and she laughed.

"You alright?" she asked.

She shifted, and her robe moved, showing some of the expanded pink circle around a nipple which remained only visible as a swollen shape beneath the cloth. Each breast was immense, bigger than my head. She put her hand on my jaw and steered my eyes back up to hers. Her laughter had turned to an amused intensity, and her fingers moved across my lips, then pushed into my mouth. She swirled them, pressing the inside of my cheek, then pushing deeper. I salivated, anticipating something more. She stroked my face gently, and then --

"I'm off to bed. I'll see you tomorrow. Have a nice sleep!"

And with that, she went upstairs.

...

I woke the next day to an empty house. Ms Dare was out until mid-morning, and when she got back, I was on my laptop trying to square away some tasks. She was done up in business-formal perfection, sleek black and white. I looked up and greeted her, and she sat down opposite me.

"Good morning. Just met with the lawyers. I'll have to give you access to my calendar. I want to finish some things off this afternoon but before that, lets formalise your new role."

"Ok, Ms Dare," I said.

She laid a document on the table- Role Description: Executive Assistant.

We went through the dot points. It was straightforward: scheduling, correspondence, reviewing, briefing. Errands and other duties as required. I assured her that I was very comfortable with all of it.

"Well, that's settled. Congratulations, you're my new assistant." She paused. "Now... There's another aspect to this I want to discuss."

She stood, took off her cropped blazer and shook out her hair.

"We have a bit of a... thing going on."

"... we do."

I swallowed, my mind picturing her half-nipple once more.

"This is separate to work... kind of. I want to make things very clear for you. It's obvious that I excite you, and you are very submissive to me. It's perfect. I need you continue to do the things I want."

My stomach fluttered, and I nodded.

"I think for now we can leave it at that. I've got to finish some things off for the rest of the afternoon, but I've arranged an appointment for you. It fits into the category of "things I want". Understood? I'll see you later."

"Ok". I said, "Thank you."

...

I had a long shower after my appointment. It had been something of an ordeal- a kind young woman had waxed my entire body. She had told me I was booked in again for two weeks' time and gave me a kit with some creams and tools to maintain my skin. I looked in the mirror -- I was completely smooth and surprised at how good it felt.

I dressed and found Ms Dare in the living room.

"I am done for the week. I will not engage with any of those vampires until Monday, no matter how much they claim to need it. How was your appointment?"

"uhh.. unexpected? But good."

"Good. Let's have a drink."

After I'd poured our glasses for a second time, Ms Dare brought up my appointment again.

"So you liked it? I knew you would. I bet it suits your body perfectly."

"I hope so."

"Show me."

I hesitated... Ms Dare crossed her arms with a flash of sternness. I began to undress.

"Mhmmm".. Ms Dare nodded her approval. "Everything off please."

My last piece of clothing fell to the floor.

She stood up and walked around me, looking me up and down.

"I like this." She said, "You're in good shape. Great legs. Great ass. It could be bigger- let's work on that." She slapped it and squeezed roughly.

"Ok, Ms Dare."

I acutely felt the sensation of being fully nude while she was fully dressed.

"You know, it's kind of hot in here."

She undid a shirt button. Her breasts popped outward as the constraint was released. As I stared, my cock began to harden. She put her hand on my chest and slid upward, laying it across my throat.

"Kneel."

As I did, she sat back onto the lounge and undid her skirt. Her transparent black stockings were thigh-high, and above them her bare thighs widened to present her milf's pussy, shaven except for a neat strip of short hair above. I paused, breathing in the strong sweet smell that hit my senses, and she ran her fingers through my hair and pressed my face toward her cunt. She held me there, and I looked up to her, begging. Then she let me go. I lapped at the taste of her wetness desperately.

...

The first week of my new role was charged with energy. I kept Ms Dare's schedule running smoothly throughout. She had told me I wasn't to touch myself, and to discourage me from doing so, she had locked my penis in a small chastity cage and taken possession of the key. She also insisted that from now on, I would exercise my butt daily. Paradoxically, Ms Dare was highly encouraging at work. We worked well together.

The next two weekends, Ms Dare was away. I found myself becoming restless with arousal and eased the tension with intense workouts and losing myself in tasks. Ms Dare kept me eager with her wicked smiles and obvious teasing, and I endured. I kept my next waxing appointment and noticed an even smoother finish than the first. I was completely blemish-free.

Toward the end of the week, she told me to be at hers again on Friday night.

...

Not long after I arrived, Ms Dare told me to shower and meet her in her bedroom. Naked, please. I entered on fire with anticipation and took in the sight of her. She wore a black silk nightgown over nothing but dark stockings and black lace panties and was refreshing her lipstick as I went in.

She looked me up and down. A smile flickered.

"Turn around a little," she ran her hand down my side and felt my ass.

"You've made some progress on that butt, haven't you?" she said as she slapped and squeezed.

"Yes, Ms Dare."

She slid her nightgown sideways, exposing her breasts. I witnessed them fully for the first time. Two huge spheres, firm, falling halfway down her torso and protruding well past the curve of her side. Her swollen nipples surrounded by large, lovely pink circles in fine proportion to her enormous bust. She smirked at my reaction and reclined onto the bed, bringing me with her to bury my face in her tits. I sucked on her nipples as she squeezed my ass. My cage throbbed as I felt her incredible body, lost in excitement, and I felt her fingers stroke my taint and touch and feel my ass hole.

"That feels good, doesn't it?"

"Yes, Ms Dare."

"I have something to show you."

She got up, slipped her gown off and deftly clasped on kind of belt, and I saw a long, thick cock had become part of her. She watched my eyes as the heavy strap on swayed, lifelike with veins and a perfectly shaped head. She stroked the side of my face, looking down at me, and slid the big, black head across my lips. She slapped it against my cheek, and in response I opened my mouth.

"You are a slut," she said as she guided her cock between my lips.

"I knew you would love this."

She pushed my head down the length until she met the resistance of my throat. I salivated and she pulled me back. Then down again, thrusting as she did, and this time I gagged. Slick spit coated the dildo. She pulled me off the bed to kneel in front of her and hummed deeply as I took the shaft in my hand. Looking up, I saw again the huge and flawless surface of her tits and still she stared down at me as I worked her dildo harder, and I realised that she could feel the sensations of through some trick of the mind. She fucked my face more forcefully, both hands holding fistfuls of my hair, pumping my head back and forth. My cock was straining hard as she pushed deep into my throat. Amazingly, she built to a climax and began to shudder. She held herself in, then pulled out and I gasped, ropes of saliva hanging from my jaw.

I recovered my breath as Ms Dare slowly masturbated her dildo.

"Get up onto the bed and show me your ass."

I crawled on and she slapped my ass, harder now, and chastised me.

"Stick it out. You're my slut, act like it."

She slapped me again and I sank my back into a low curve to present myself to her.

I was completely lost in slut-like feeling as she lightly ran a finger up my smooth taint -- my muscles contracted and a string of precum fell from my cage. I breathed heavily as she spread my ass hard and I felt her enjoying my humiliating position. She reached down and squeezed around my little cage, her fingernails digging in, and as she did so she smacked my ass three times, so hard and sharp that I gasped. Her hands gripped my hips, and I felt her heavy cock slide lazily over my ass, then beneath. Her body press against me, and she jerked my head back and slipped her fingers into my mouth from behind, hooking my cheek and slapping the other side of my face, quick, stinging taps.

"You're going to fucking love this aren't you."

"Yes, Ms Dare."

She poured on a slick oil and began to prod and rub my rim with the head of her cock. The stimulation was so pleasurable, and I was so sensitive from my weeks of chastity, that I let out a high moan.

I breathed deeply as she increased the pressure, moving the cockhead up and down and in and out, roughly squeezing and caressing my ass and whispering abuse as she did. I wiggled my ass in a kind of frustration, and she slapped me, and pressed harder, and I gasped as a stretching pain shot through me. She held it there and continued to caress and squeeze my ass and inner thighs.

She pressed again and I felt the resistance give way. Her cockhead slid into me. She started small thrusts that grew longer each time. Another submissive moan came out as she violated my ass deeper and deeper, and the pleasure became stronger, and the discomfort dissipated. I started moving my hips in time with her rhythm.

"Anal whore", she said, and before I knew it I was accepting her full length and feeling nothing but pleasure at being fucked.

Ms Dare took my waist in her hands and began to fuck hard, her hips slapping against me. She moved over me, and both hands took my throat and she fucked me like that, choking me and slapping my face and shoving her fingers into my mouth. She was vocal in her abuse, calling me her filthy slut, her cunt hole, her useless cock whore. My legs began to shake, and she let her weight fall on me, pinning my legs beneath hers and holding me by my head and throat as she built herself to orgasm again, shuddering and thrusting her dildo deep within me.

She withdrew and caught her breath, resting back against the headboard and watching me with a satisfied arrogance as my cock leaked precum.

I waited for her command still filled with tense energy and unable to release. When she beckoned me, I moved to her and straddled her thighs. She shifted me so that my cage sat next to her fat strap on, and cruelly took it between her fingers and moved them up and down. She flicked it hard, and I flinched at the vibration, squirming.

"So tiny," she smirked.

She allowed me to feel her breasts and suck her nipples again, gently stroking the back of my head. They were engorged and filled my mouth as I suckled. After a minute, though, she cupped my ass and guided me to squat over her strapon. I lowered myself to have it back inside me and soon I was bouncing up and down on her lap.

Ms Dare watched me with disgusted glee, her hands on my hips as I arched my back and pumped mindlessly on her cock. My cage flapped uselessly. I felt the pleasure building and desperately tried to work myself to cum. I spread my ass, increasing the sensations, and I tried and tried, but I couldn't reach the point of climax, and collapsed back onto the bed, panting hard and staring at the ceiling. I felt spent.

A finger stroked the side of my face gently.

"Poor thing. You want to cum so badly, don't you?"

I nodded.

"Well, I don't think you're ready yet. But I do have one last treat for you."

She stood on the bed, directly over me, and I saw her cock was gone. Her beautifully shaped thighs and ass tapered to her slimmer waist, and I appreciated the view of her curves from below. She turned and lowered herself, putting her hands on my chest as she descended into a deep squat. Her pussy was wet with clear droplets running down her inner thighs, but as she approached my face, she gave me her asshole. I laid my tongue against the glorious shape and lapped at its primal taste, rolling my eyes back. I worked my lips and mouth to pleasure her.

She moaned smug and satisfied,

"That's right, anal piggy. Eat my ass,"

and reached back to take my head, pressing me into her. Her aggression built, and she sat her full weight onto me, and I was smothered, struggling to breathe while she rode my face. She spread her ass with her hands, and I worked my tongue as deeply into her asshole as I could. Then, she started to pleasure herself, moving off my face and sitting back with my head between her thighs.

She rubbed herself frantically with one hand and with the other she smacked my cheek, choked me, and shoved her fingers in my mouth to make me gag. She laughed and moaned and abused and degraded me, her fuckpig, her cockslave. Her breathing quickened and her body began to jerk, her hand tightened around my throat as she sat her sopping cunt against my face and launched into an explosive orgasm. As she grinded her saturated pussy on my face and mouth, my body raged with humiliated arousal, ecstatic at her ragged screams of pleasure.

.....

Following this climax, we lay in silence for a minute. Ms Dare took my hand and led me to the shower. We stood together in the steaming water and ran our hands across each other's soapy bodies.

"I really needed that. Thank you."

Ms Dare she kissed me gently. I spent a long time massaging her, feeling her massive tits and ass in a state of satisfied arousal. When she ran her slippery hand over my asshole again, I flattened against the glass and stuck my ass out begging, but she pulled me back to her and held me close.

"You still really want to cum, don't you."

I nodded.

She held my chastity cage, and turned it from side to side, inspecting.

"You were so close earlier. We can take a less strict approach in the future but for now this stays on."

"Ok."

She kissed me again, this time pushing her tongue deep into my mouth and sucking at my lips.

"This works for me," she said.

"Me too."

End of Part 1.