Ms Dare's Femdom Anal Slut Pt. 02

Ms Dare and I were on a flight home. She had just finished a week of negotiations, and I had assisted her, organising the logistics and generally ensuring she didn't have to worry about anything but her executive work. For about six months now, I had been her live-in housekeeper and her assistant at the office. And, of course, I continued to be her fucktoy. My chastity cage remained on, except for the times it had been replaced twice with a smaller one.

"Have you had any serious relationships before?" She asked me.

"Well... yes. No, not really..."

I explained that I had had a close friend called Laura, who I had supported when she was low on money or needed a ride or a place to stay. She fell in love with me, but I rejected her. Then, somehow, the script flipped. I fell in love with her, and I spent the next two years trying to win her over. She didn't reciprocate, and eventually we drifted apart.

"Well, that sounds fucked."

"Yeah. It was."

"Do you still think about her?"

I paused.

"Sometimes. To be honest, I think we could have been together if things had worked out differently."

Ms Dare let out a mock sympathetic sigh. "So sad! Life is a tragedy. You could have married her and had little children running around! In fact, maybe one day you still could!"

I rolled my eyes at her teasing.

"It sounds like you're still in love with her," she went on.

"I don't think so," I wasn't entirely sure.

"Maybe you should figure it out."

...

So I called Laura. I wished her well, and we met up. She was the same as ever- bubbly and sweet. Confident. When I had first met her years ago, I hadn't found her beautiful, but flat chested and plain. Over time, I had fallen in love with her doe eyes and the subtle curve of her mouth, and her angel's hair, perfectly straight, a deep honey color and medium length; and her ass. She was a modest dresser, but I came to realise that her butt had an incredible shape and was far bigger than it had any right to be.

I introduced Laura to Ms Dare and they got along well. Ms Dare became a kind of mentor for her, a woman encouraging another woman to succeed, and over time Laura became closer to Ms Dare than to me. I didn't mind. I enjoyed occasionally seeing her and being around her again. Once or twice, I might have imagined sleeping with her, but that was strange territory given my situation with Ms Dare.

Ms Dare had trained me to orgasm only from being fucked with her strap on. She fucked me at least weekly, and I found it so pleasurable that I didn't think about using my cock anymore. But a while after she had become friends with Laura, Ms Dare stopped letting me orgasm altogether. She would sit on my face and run her fingers lightly over my body, or she would tie me up and spank me, or straddle my hips with her thick milf's thighs and position her hot pussy, shaved except for a neat strip above, right on top of my stiff caged dick and rub herself off, but she would not fuck my ass and she did not let me cum. It was agonizing and I developed a near constant feeling of sexual pressure.

I was in this state when the three of us were sitting around the coffee table, and I learned that Laura was sexually frustrated, too. She told me that she hadn't been with anyone in a while, and although there were a few a nice guys who had been trying with her, they just didn't make her excited.

"She wants to do something a little more interesting." Ms Dare told me.

Laura agreed. "That's right."

They had clearly planned something.

"I'm arranging something for Laura. I want you to be involved. It will help to clear the air between the two of you." Ms Dare smiled.

"What do you mean?" I asked.

"A special activity. A session of sorts. It will be super hot. You're going to love it."

She stroked my cheek, and a hint of glee flashed on Laura's face.

***

Ms Dare and I arrived at the establishment. She was dressed up in black, with tall high heels that exaggerated the luxurious shape of her legs and see through long stockings suspended under a black coat that stopped halfway down her thighs. I was told to be ready but knew nothing about what to expect, so I was recently waxed, clear and smooth all over, and desperately looking forward to some form of orgasm.

The two of us were led through by a busty blonde, and beautiful, half-naked dancers walked past us. Our room resembled a fine hotel suite and had a low king-sized bed and an open floor space with a sofa and coffee table to the side.

Ms Dare unpacked her kit and took off her coat revealing a lacy black bodysuit that provoked her mature curves. It was cut low on her chest, highlighting the defined roundness of those massive tits. Her thick, womanly thighs made my mouth water.

"Everything off."

I stripped quickly and Ms Dare tapped the wooden bed-end. I leant my hands onto it and stuck my ass out as I had been trained to.

"Lower."

I arched my back and leant down onto my forearms, and my lust skyrocketed as Ms Dare fastened the choker around my neck and bound my hands together. She held onto the end of my leash as I kept my position. Then, Laura entered.

Her hair was in pigtails, and she had light makeup on, and a tight white top that left her slender stomach uncovered, and a tiny plaid skirt that barley contained her thick ass. Her long, smooth thighs ran bare down to knee high white socks and shiny shoes. She looked much younger than her age.

"Laura. You look amazing. Don't you agree?"

"Yes, Ms Dare."

I was torn between my submission to my Mistress and my longing for Laura. I wanted to hold her and kiss her and feel her body.

"Thank you!" Laura giggled with excitement. "My gosh. Look at you two."

She approached and inspected my body, pausing when she saw my cage.

"Look at that tiny cage! How does anything fit in there?"

"I ask myself the same thing. Look, he's excited."

It was clear that I was. My cage protruded slightly as it constrained the pressure inside. Ms Dare gave my ass a firm slap.

"Does Laura excite you?"

"Yes, Ms Dare."

"Kneel."

I sat back onto my heels.

"Does he even use his cock anymore?"

"No. He cums like a girl now."

Now I felt humiliated.

Ms Dare turned to me. "Look at her."

I looked up. Laura posed seductively, teasing me. She turned and bent forward, bracing herself on the bed-end, and I saw her amazing, round ass up her skirt. Ms Dare led me forward, and Laura arched herself more dramatically. Now, I could see everything -- her fine, smooth pussy and her asshole, a sweet pink star were right in front of my face.

Ms Dare squatted down beside her, facing me, and reached around to spread Laura with both hands.

"You are very lucky. We shouldn't be letting you do this. You may touch her asshole only. Understood?"

"Yes Ms Dare."

"Go on. Disgrace yourself."

I ran my tongue over her anus. I lapped again, feeling its edges and tasting the skin, and Laura gasped.

"Keep going." Ms Dare said.

I began eating her ass eagerly, pouting my lips and suckling and working my tongue into her. It was heaven. Ms Dare watched intently as I desperately worked Laura's asshole with my mouth.

"Anal pig." She muttered.

She took hold of my head and pressed my face forward.

Laura gasped again, laughing and saying, "I can't believe he's enjoying this."

Ms Dare wrenched my head back and forth a few times, her aggression building.

"He fucking loves it."

Ms Dare let me go on a while longer, watching with disgust, but soon it was over.

"Enough."

Laura regained her composure and sat down on the bed. Ms Dare pulled me up off my knees hard, choking me with the leash, and bent me over the bed-end once more. Then, she brought a chair directly behind me. She ran her fingers along my taint, and I felt the excitement of lubricant on my skin. Laura watched, bemused, and I felt embarrassed and desperately aroused.

"Please, Ms Dare."

She slapped my ass, aggressively.

"Thank you."

Ms Dare turned to Laura. "Are you ready?"

"I'm ready." She took a deep breath.

"Come in!" Ms Dare called.

The door opened and two well-muscled, tall black men entered. They wore masks, like those in an ancient theatre, and dark, loose cloth pants. Apart from that their bodies were bare.

Laura watched them approach her. She sat cross legged, sweetly looking the picture of innocence. As soon as they were within reach, she reached out and ran her hands across their abs. My Laura. I felt my choker tighten as the men went onto the bed and began to feel her body. They felt her flat stomach, one quickly sent his hand up under her top and massaged her breast, the other had his hand on her inner thigh, feeling up higher and higher. Quickly, she took off her top. Her chest moved with excited breath, her small tits were firm gentle mounds with hard, perfect nipples, now covered by rough dark hands.

Ms Dares hand was now under my chin, around my throat, the other squeezing around my cage, and she whispered.

"Oh Dear. Look at that!"

She smacked my face.

"Your little cock is rock hard, I can feel it. You can't wait to see her being fucked while you sit here like a cuck. Isn't that right?"

I breathed out heavily. "Yes, Ms Dare."

She lazily slipped her finger into my mouth, hooking my cheek, holding my throat from behind with the other.

Laura was kneeling between the two men now. She pulled down one of their pants -- they slipped down easily and the man's cock sprung out from beneath his waistband. Laura gaped at the size in disbelief. The other man had taken her hand and put it onto his own cock -- she felt it through his pants, then pulled them down too. Hungrily, immediately, she opened her lips onto its massive head, then turned and did the same with the other. She had both hands around their thick black shafts and took each cock into her mouth in turn.

"Look how much she loves it", Ms Dare said pressing her cheek against mine as we watched.

My cock was aching as it swelled in its cage. Ms Dare tapped it several times with the flat of her hand, and I felt more pressure than before. I watched Laura sucking one cock then the next, staring up into their masked faces lustily. One of the men came down to feel her ass up under her skirt as she knelt, and she leant forward, bracing herself against the other who was holding her up by her cute, honey-coloured pigtails. She worked his cock deeper into her wide-open mouth. The hand under her skirt was now crudely rubbing at her pussy.

I felt the full impact of so many weeks without any kind of orgasm, and finally Ms Dare had attached her strap-on and was tying my leash to the end of the bed. I leant onto it with my hands still bound, and she was rubbing the head of her fat cock against my slippery asshole. I felt with relief the dildo pushing into me and I pushed myself back onto it. As I stretched to accommodate it, I watched Laura quickly unclip her skirt, and saw her thick, incredibly shaped ass as it stuck out while she went onto all fours. The man in front of her knelt as she continued to throat him, while the man at her rear now stepped down off the bed, placing both hands onto the cheeks of her ass. He squeezed her hard and spread her, and Laura looked back at him, biting her lip. He slid his cockhead over her wet, pure pussy, then pressed it in, and her flawless lips parted as he entered. Laura let out a breath that turned into a moan as the man pushed his cock into her. He began to fuck her, spreading her fat ass again and sliding in and out.

As I watched I moved myself, working my asshole up and down the length of Ms Dares dildo, and the pressure I felt in my cage shifted to become a quivering sensation in my core. Ms Dare leant down to my ear.

"You lucky slut," she whispered as she began to pump me.

Now I became lost in the feeling. The slide, in and out, and Ms Dare slapping against my ass. Wicked abuse came from my Mistress as she fucked me harder, working herself up to a fast, relentless pounding. My insides quaked and my ass began to spasm as precum dripped from me. I felt her heavy tits pressing into my back and felt stars fill my eyes and a warmth in my core as a slow wave came upon me.

My legs were shivering, and as the wave faded, Ms Dare unclipped the leash that had held me onto the bed end. She brought me back as she took a seat on the chair behind her, though her silicon cock remained inside me. One arm wrapped around me, the other at my throat, and me still arching my back, sitting on her cock as she held me in place to continue watching.

Laura was now chest-down on the bed. The man in front of her still held her by the handles of her pigtails as he slid his cock in and out of her mouth. The man behind gripped her tiny waist and fucked the living daylights out of her. Her ass was rippling as he smacked into her, and her face showed a drunk ecstasy. Laura began moaning higher and louder until she gasped and lost control. The man changed pace, fucking deliberately now, and then shuddered and pressed himself into her. He ejaculated his sperm deep inside her pussy.

There was a lull as Laura caught her breath, giggling. I saw cum dripping from her pussy as the man withdrew his long, thick cock from her. He moved away, turning, and exited the room. Laura rolled onto her back. Now, the other man stepped in between her open legs, and Laura looked up at him, then to the door as another man entered. He was the same as the first two -- muscled, dark, and with an enormously large cock. He took his place at her head, sitting with his thighs either side of her face and laying his cock on top of it, and he took her breasts into his hands and kneaded them. The man at the other end began to fuck her.

"Oh. There's a few more." Ms Dare said into my ear.

She rolled her hips, and my insides felt a fresh surge of pleasure, she took hold of my waist and I moved myself in time with her motion.

Ms Dare was content to continue like this for the next while, her cock moving inside me as I bounced lightly on her and watched Laura. She was doing her best to service the massive cock at her mouth, but the position on her back was difficult and her whole body was being jolted by the man who fucked her. There were loud, wet slaps coming from that end, and they continued as the man rammed his cock into her again and again. At a break in the pace, Laura shifted, sitting herself up and signalling for the owner of her mouth-cock to lay down, and she moved on top of him and gave him his turn, taking his cock into her pussy and riding it. The other, she pulled toward her, and he stood at her side, and she hungrily lapped up the layer of cum that had been in her pussy from the first cock that had blown inside of her.

She rode leisurely, moving like a wave, and black hands felt her ass and tits as she they fucked her face and cunt. The pace built again, and she was sliding her hands up and down the standing man's shaft, working the head with her lips and tongue then taking it as deeply as she could. At a climax, the man tilted her head back, grunting, and spurting a thick, hot load between her lips and onto her face. Laura was full of glee as cum dripped over her, and she began riding the cock inside her pussy with fresh enthusiasm. Her nipples were so stiff, and she was laughing and moaning with pleasure.

"Look at your Laura!" Ms Dare said to me.

"All she ever wanted was her cunt filled and her face covered."

The spent man left, another entered, and now Ms Dare started to fuck me hard again. She stood and bent me over in front of her and wrenched at my hair to force my head back, and shoved her fingers into my mouth as she pounded my ass. Pleasure. Pure fuck lust, as I felt wave after wave of submissive energy coarse through me and I leaked onto the floor. Being choked again, being slapped as I was being fucked. Her hand covered my face, my mouth, both hands held my head then choked me as she demolished my asshole, and she came, too, breathing heavily and shaking.

The third man was finishing now. Laura had raised herself so that he could drill her from below, and he had filled her pussy with a second load of cum. He tagged out for another, who began fucking her from behind. Cum ran down her inner thighs, and she was on a spit roast again. I sat back onto Ms Dares cock, and she tapped away at my cage again, holding my throat with her other hand. We watched as Laura moaned and sucked while the two men violated her mouth and cunt, and soon she took another thick splatter of semen on her face. It ran down her neck and onto her chest.

Now, the last man, the fifth, had her to himself, and he took full advantage. He lay on top of her, and she wrapped her legs around him. He fucked her into the bed with his full weight, plunging his cock as deeply as possible, and Laura quaked and writhed, but he held her in place and she felt the continued pounding of that final cock. And, after a last effort, a final minute of heavy pounding, he pressed deep inside her and filled her cunt with his semen while she orgasmed silently, her eyes rolling back into her head.

The last man stood and left.

Laura lay on the bed, panting, her face covered in cum, her legs still spread and her pussy dripping cream. She stared at the ceiling.

Ms Dare was finished, too. She moved me off her, and I felt the emptiness of her leaving, though as it is with anal orgasms, my insides were still buzzing with energy.

Ms Dare put on her coat, and following her lead, I dressed. Laura was still in a daze -- Ms Dare whispered something to her, and she nodded and smiled and put her hand up effortfully to wave us goodbye. And, together, Ms Dare and I went home.

...

That night, as I sat up on our bed after my shower, Ms Dare stepped into the room. Her body was naked and I fluttered at her truly massive tits, busting out of her chest with large, round, areolas smattered with sexy raised bumps. She approached and pressed my face into her. I suckled on her swollen nipples and she fingered my cage as I stiffened. She shifted between my legs and produced the key and smirked as she unlocked it. Slowly, she removed it, and took my hands onto her tits. I marvelled again at their feeling, firm and heavy, and my cock stiffened to full length. If felt a tingling, and Ms Dare dolloped oil onto the head. She began to tease me, lightly stroking with her fingers.

"Did you enjoy your day?" she asked.

"Yes."

Her light touches were electric -- I hadn't felt this in a very long time.

"What was your favourite part?"

Her hand fully gripped my shaft, and she gave it a long, full stroke.

"Uhh.. r... right now.." I managed.

She stroked again and I nearly came immediately, but she pulled away.

"Apart from right now."

She ran a finger up the centre of my underside, and I pulsed, a drop of precum spilling out.

"Fuck." I couldn't think.

She began to stroke me with two fingers, up and down, lightly.

"Laura had a nice time. She told me it was her ultimate fantasy."

"Uh huh.." I was trying to buck my hips, but at that Ms Dare stopped touching me again.

"She said, 'I've always wanted to be the centre of a gangbang.' And I asked what kind of guys she liked."

Again, Ms Dare stroked my cock properly with her whole hand, though very slowly.

"And you know what she said? She said she wanted five black guys with huge cocks to fill her with cum."

I gasped, and she stopped again, and I rocked my hips uselessly.

"Wasn't it nice to see her wish come true?"

"Y- yes Ms Dare."

And Ms Dare swirled one finger around my ass rim and ran the other slowly but purposefully up the length of my cock. As she reached the most sensitive part, right underneath the head, I began to pulse and spasm.

Ms Dare mocked a high moan and, without touching me, mimicked an enthusiastic hand job around my throbbing cock. A dribble of cum was released.