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Mistress Monique Pt. 02

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This wasn’t even my fantasy, I thought as I purchased the clamps, butt plug, heels and maid dress online with expedited shipping.

The next day I brought the items in a backpack to Mistress Monique’s apartment while she was at work. I put everything on then placed the butt plug in my ass and tightened the nipple clamps painfully so they wouldn’t fall off, then looked in the mirror. With the hair and makeup applied I looked like an ugly woman. This wasn’t my fantasy, but my locked up cock was crying in frustration as I beheld the sissy in the reflection. I took a selfie and sent it to Mistress Monique as she commanded me to do every day before beginning the list of chores she had assigned. I walked clumsily and painfully between tasks. It was degrading and humiliating, yet I felt I had never been hornier than when I was washing Mistress Monique’s underwear and scrubbing her toilet with a locked up cock, wearing heels, and no hope of relief when I left. After a week of being unable to sleep from sexual frustration, and also being ignored by Mistress Monique while keeping her apartment spotless, I finally received a text from her that read “Come over tonight at 7pm sharp.” I was elated and also looking forward to both some relief and quality time with her. I hoped she hadn’t been going over to Ben’s, or anyone else’s for that matter.

When I arrived, Mistress Monique was wearing a black dress with a tight low cut that showed off both her amazing chest and the key to my chastity cage between her high, curvaceous breasts. “Come in,” she invited, and “follow me,” she instructed as she led me to the bathroom, her high heels leading the way under her swaying hips. I was unsure of what we were doing. She led me to the toilet then took a piece of tissue paper and wiped it behind it where man-spray can accumulate – other men who aren’t caged and don’t have to sit down to pee. She displayed the dirty piss-covered tissue with a disappointed expression on her face.

“I’m sorry.” I began. But she placed a finger on my lips.

“I can’t accept your apology. If you’re truly sorry, go into my bedroom and use the cuffs you’ll find there to secure yourself over the chest in front of the bed. Tonight I’m going to show you what being my slave is all about.”

I was hopeful she wouldn’t beat me too badly and might even unlock my penis afterward for some much needed attention and maybe even some hot sex. I saw the cuffs and first secured my legs to a couple rings set in the chest, then looked and saw that the cuffs for my hands were already attached to rings set in the poster bed and managed to get the second one locked on using my mouth. My cock struggled in its prison, forced downward by the cage resting against the chest.

After what must have been fifteen minutes, Mistress Monique came in the bedroom. I tested my bonds and found myself completely helpless. Why did I let her do this to me?!

“It’s scary isn’t it?” Mistress Monique asked, running her hands through my hair and breathing into my mouth, yet not quite kissing me. I nodded my head, afraid to speak and make my punishment worse. She reached into a drawer and pulled out a ball gag and an imposing whip. “See?” She teased, “You’re not the only one who’s been shopping. I’m taking my role seriously as well.” Next, Mistress Monique reached over my head and locked the ball gag in my mouth, strapping it in place. “I have neighbors” she explained which made me even more fearful. Then she walked behind me and my world lit up in flames as she administered my punishment with the whip. I screamed. I danced and tried to hop from leg to leg, but the restraints wouldn’t allow it. I shouted my old safeword unintelligibly into the ball gag, but the whip kept falling until I could barely struggle. I never got used to it but I eventually gave in to her and the punishment. Finally, the whip stopped and the ball gag came off me. Mistress Monique, now full of loving sympathy came into my field of vision and asked me if I had anything I wanted to say her.

“I’m sorry!” I sobbed. Then Mistress Monique took my head in her hands and told me that now she could accept my apology and asked me if I would like any relief since I had been locked up for a week. I nodded vigorously. Mistress Monique went back to the drawer and pulled out a strapon that was much larger than me, even if I had been allowed a full erection, and began buckling it on. She looked so intimidating and amazingly sexy that I didn’t question her, and couldn’t even had I wanted to. Then she pulled out a bowl and placed it under my caged cock, climbed onto the bed and beckoned me to give her strapon head. I didn’t know it would turn us both on so much, but the humiliation of going down on her cock after that whipping was absolute, and we both gave ourselves to the act.

After some time she said, “Now it’s time for some relief for your poor aching balls.” Mistress Monique got off the bed and walked behind me, then slowly worked her cock into my ass. The fucking antalya escort was assertive, deep and rhythmic. I could feel my penis emptying something despite the cruelty of being fucked while in a chastity cage. I also experienced a new kind of orgasm that felt like profound full-body waves of pleasure that washed over me again and again, but provided no reprieve from my horny need.

After a thorough fucking on the heels of the whipping, I felt utterly spent but would still have done anything to cum. I hoped I would get that chance. Then, Mistress Monique removed the strapon and lifted the bowl of slightly white pre-cum. I knew what I had to do and ate it greedily as she held the bowl to my lips.

After feeding me my pre-cum, she removed her clothes and crawled onto the bed on all fours with her ass raised in front of me and instructed me to eat her asshole and pussy. With my arms screaming in their restraints and my tongue in her ass, I tasted and inhaled her musky backside as I shamelessly served Mistress Monique to an earth shattering orgasm.

She laid there for a while in post-orgasm bliss, having had a good workout on my ass. I knew better to complain though my limbs were strained and painful. Then Mistress Monique got up, took a key out from her drawer and unlocked my cuffs, saying I was free to go. It dawned on me she really wasn’t going to reach between her breasts and use the key hanging there to release my cock.

Following my gaze, she said, “It’s so funny; you’re so much bigger than me that I’m sure you could overpower me, take the key to your chastity cage, pin me down and take out your frustration by forcing your cock into me. It would be pretty hot if you did. But I bet you won’t, because you need to worship me, and you need me to do this to you. I hope you’ll do a better job tomorrow. Good night.” She said; sweat standing out on her body as she excused me from her company.

I knew she was right. I wouldn’t take the key and I did need her to do this to me. “Good night Mistress Monique. I’ll do a better job tomorrow.” I left, still shivering.


Two wall-crawling, mind bending weeks later Mistress Monique again texted me, “Come over tonight at 7pm sharp.” My cock jumped in my cage, but fear also jumped in my throat. Was she going to punish me again? I really hoped she wouldn’t, but couldn’t help be turned on by the thought. The only part of me un-conflicted was my penis, struggling again in its chastity tube by the promise of torment from its mistress. Despite my fears I knew I would be there. It had been three full weeks since I last saw my penis or had an orgasm. And besides, I devotedly loved Mistress Monique with all my heart.

When I arrived the door was cracked. I peeked my head in and Mistress Monique was sitting on her high backed chair engaged with her phone. “Chains, bedroom” she commanded, not looking up from her phone to greet me. I was angry that I had been ignored for two weeks, and then to be so off-handedly talked to, but I dared not show it and obediently walked into her bedroom, stripped and not thinking of a way to escape my predicament, chained and cuffed myself over the chest in front of her bed, then waited for eternity until Mistress Monique walked in. Her high heels and shapely legs moved into my field of vision as she looked down on my exposed body. I gazed up at her chest and my chastity key to find her beautiful eyes. “My panties weren’t folded properly today.” She admonished.

Any hope about escaping from pain vanished as she again placed a bowl under my caged penis to catch pre-cum and hefted her whip from the drawer.

Mistress Monique moved behind me and told me that I had to ask her for this punishment, saying, “If you want out of that cock cage and out of my life just let me know right here and now since you aren’t holding up your end of the bargain and cleaning my apartment perfectly. Or, beg me to correct your behavior and we can begin. It’s up to you. I don’t want an unwilling slave.”

It was almost too much, but I made myself speak, with gritted teeth and closed eyes. “Please, Mistress Monique.” I begged. “Please correct me to be a better slave for you.”

Then, this perfect woman began to rain her whip on my backside, searing the skin in pain. This time she hadn’t used the ball gag, but I knew I mustn’t cry out loudly. The effort to hold back my screams seemed to make the whipping even more painful as I swallowed my sobs.

After Mistress Monique finished thrashing my ass she again placed a bowl under my chastity cage, retrieved the strapon and put it on.

With my ass on fire, I was only aware of pain and desire for her, and it felt like that’s all there was in the world, when there was a knock on the door, breaking the spell.

“Oh, that’s Ben! He’s early.” Mistress Monique walked past me, to the door. I could hear their hushed voices, but couldn’t see anything since I was restrained and couldn’t move. Mistress Monique sounded kemer escort excited, while Ben doubtful.

NO! I thought. Not him! This is our time: mine and Mistress Monique’s. I knew she fucked him but what is he doing here now? What if he sees me like this, chained naked with a chastity cage and a red streaked ass? I couldn’t fathom that level of humiliation and struggled to free myself so I could get dressed like nothing was happening, but was unable to budge against the restraints. I was still helpless and felt very exposed. I could hear footsteps approaching.

“See?” I heard Mistress Monique say.

“Holy shit.” Ben commented. “You weren’t kidding, this is pathetic, Mona. And he’ll just do whatever you say?” Ben asked, as he tried to wrap his mind around the naked male chained over the chest in front of the bed.

“That’s right.” She confirmed, nuzzling her lips under his ear. “Would you like to see? This will blow your mind.”

I was horrified, speechless, betrayed. My eyes sought Mistress Monique’s for explanation, and found only playful cruelty.

Mistress Monique moved behind me, and rubbed my ass with the tip of the strapon and said, “ready slave?”

Ben relaxed on the bed, looking at me with a sneer of superiority. I briefly considered playing the brat, but knew I had to answer Mistress Monique or I would be punished severely. “Yes, Mistress Monique.” I replied, and Ben laughed at me, apparently in disbelief that a man would ever be in my position. I looked away from him.

Monique entered my ass with her strapon as Ben continued to absorb the scene playing out in front of him. I followed his gaze above me to my mistress rhythmically thrusting into me with her hips. Ben reached down his pants for a few minutes then asked, “Is he gay?”

“He’s as gay as I tell him to be.” she replied.

“OK then.” Ben said. He undressed. I couldn’t help noticing when he pulled his pants down how much larger of a cock he had, even if mine were out of the cage. No wonder Mistress Monique loves him to fuck her, I thought. Ben moved in front of me leading with his huge erection.

“OK sissy” Ben commanded, “time to suck a real cock.”

“Slave.” My mistress soothed. “I would love to see you suck Ben’s dick for me.”

Each of Mistress Monique’s thrusts against my whipped ass sapped any will to negotiate. Ben’s cock must have measured nine inches, and was imposingly thick. It was close to my face and I could smell his musky scent. I had never done this before so didn’t know what to expect. I opened my lips obediently and Ben entered my mouth. His cock was so much more alive and firmer and hotter than I expected. We adopted a rhythm between the three of us, as Mistress Monique thrust into my ass, I went down further on Ben’s shaft that was fucking my face in turn.

“That’s it.” she said. “Worship that cock.”

And I did. I devotedly sucked and kissed Ben’s dick with abandon. First, for my mistress and then a new kind of lust took over and all I wanted was Ben’s cock in that moment.

I began to feel his throbbing increase and his balls tighten, then he suddenly removed himself from me and I felt disappointed not to feel his orgasm erupt in my mouth.

“Get up here, Mona. I want to fuck a real pussy.” Ben commanded.

I felt the strapon fall out of my ass and heard her remove it onto the floor.

“I’m going to fuck Ben in front you.” Mistress Monique said to me. “But don’t think your punishment is over yet just because I’m letting you witness something beautiful.”

With that she pulled the bowl out from under my chastity cage and squatted over it. Mistress Monique looked me in the eyes as she peed into the bowl, filling it half way with her urine, mixed with my pre-cum, then placed it between my restrained hands and in front of my mouth. Ben shook his head, again smiling at the slave’s predicament.

“I want you to lap this up while you watch a real man fuck me. I want the humiliation to be total tonight.” She said.

Mistress Monique then climbed up on the bed, her shapely, firm body facing me on all fours and her eyes just a couple feet away. Ben mounted her from behind and thrust his huge wet cock, which I had just finished sucking into her, making her moan and squirm with pleasure while my chastity key bounced between her breasts with every thrust. She leaned forward and kissed me passionately, while Ben fucked her. “I love the taste of Ben’s cock.” She teased. “Now drink” she commanded.

I lowered my head and began to lap up my goddess’s pee with my tongue as the fucking couple watched. My penis and limbs were still restrained helplessly, while Ben’s cock claimed Mistress Monique as his woman with every gyration of his powerful hips.

I had nearly finished licking the bowl when Ben’s rhythm became faster and each thrust harder.

“Cum in me! Please cum in me!” Mistress Monique begged, though I had never had the privilege. And with konyaaltı escort his final thrusts, Ben held himself inside her and moaned deeply, filling her.

They laid like that for a while before Ben rolled onto his back, apparently spent for the moment. Monique reached down and began to unlock my arms and legs. I expected to be sent home but she laid back down on her back against the headboard and beckoned me to worship her. Ben’s cum was all over her mound and inside her, and I lapped it up as I devotedly licked Mistress Monique’s pussy. After about fifteen minutes of giving her head I noticed Ben was working his own shaft while watching Mistress Monique get off from my tongue. Without invitation, he moved behind me and pressed his cock against my ass.

“Do you want this little bitch?” Ben asked.

I was so turned on, frustrated, and knew what my answer had to be. “Yes Master Ben.” I replied obediently, making Mistress Monique moan with pleasure.

Ben forced his giant cock into my ass, filling me completely and fucked me with his hard cock while I continued to eat my mistress’s pussy. Their rhythms began to synch with me in the middle and my chastity cage bouncing against his balls, until I could feel Ben’s thrusts and Mistress Monique’s breathing both quicken. Then, Ben grabbed my hips and held his cock inside my ass and I could feel him shooting his cum into me. At the same time, Mistress Monique reached the peak of her orgasm. As they both came their hands reached out for each other’s and I could see that she was looking at Ben over me. I was experiencing bringing them both to orgasm, while being denied one myself and knew I would be called on to do this again.

Ben removed his cock from me and slapped my ass hard. Mistress Monique stroked my hair with my mouth still near her clean and orgasmed pussy.

“21 days down.” She said. “And if you’re really, really good I’ll unlock you at 90 days for your first ruined orgasm.”

I had gotten much more pain and frustration than I had fantasized about when I could still jack off, but I felt totally in love and absolutely devoted to Mistress Monique, and could not wait to do whatever she told me next to prove it. And looking up at her, I could tell she knew it.


Four days later, I was changing Mistress Monique’s sheets in the requisite maid outfit which included high heels, a wig, makeup, nipple clamps and butt plug, with my chastity cage still firmly in place, when the bell rang.

Mortified I realized I had forgotten to lock the door and heard it open. I froze in place and waited, hopefully for the intruder to leave. Instead, Ben popped his head in and looked me up and down then laughed at my predicament and asked if “Mona’s around?”

I replied that “Mistress Monique” was still at work, hoping he would go, but Ben didn’t leave. Instead, he sat down on the bed and opened his pants and said, “Well, I came over here to get some. You don’t want me to tell your little pussy whipper that I left disappointed do you?”

Fuck…I didn’t. However, the euphoria of that previous night having worn off, I again hated Ben for being the real man in Mistress Monique’s life, when I wasn’t feeling as a true slave should, happy for her.

“C’mon.” he continued, reaching over to Mistress Monique’s drawer and pulling out a pair of handcuffs. “Go ahead and put these on behind your back so you can say it wasn’t your idea.” Ben infuriatingly winked at me. I knew what I had to do. Even if Mistress Monique didn’t punish me for refusing her stud, he would probably just take what he wanted by force if I didn’t play along. I walked over to him in my heels and took the cuffs from him and clicked them around my wrists behind my back. I was now under his control and there was nothing I could do about it.

Ben leaned back and I knew what was expected. I clumsily approached his cock mouth first and began licking and sucking on his huge rod and balls as he moaned with pleasure. To anyone entering the room it would look like a man was receiving head from a maid, but it was me. I bobbed and sucked his cock and I could sense he was about to cum when he pulled out, pushed my head against the ground, forcing my ass high in the air. Then he roughly pulled out the butt plug and swatted my helplessly chastised cock and balls against my leg, snorting with mirth as I moaned in lust and frustration from him slapping my caged dick. With one hand gripping my hair and the other guiding his huge cock, Ben entered me slowly and confidently then began to fuck my ass. He fucked me hard, dominantly, and I felt utterly helpless since I was bent over in front of him, handcuffed, in high heels, and physically weaker than him. After a good long hard fucking he pulled out and whipped me around to take his erupting cock in my mouth. The smell and taste of my ass and his cumming dick was overpowering, but I sucked with all my enthusiasm until he was spent and clean. I wiped his cock clean and at his command placed it back in his pants and zipped him back up.

Ben tapped my cheek playfully and told me to thank him for his cock.

“Thank you, Ben” I replied from my knees, and he slapped me hard across the face. The world spun. Still in cuffs, I fell over from the blow.

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