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Short Story: Pegged After 3 weeks in Chastity For My New Keyholder

As her slick PVC thigh high boots slid across my bare skin my cock throbbed getting harder by the second. I’d been locked in my chastity cage for a week and I lay naked and tied spread eagle to my four posted wooden bed. Minutes earlier, Mistress H arrived at my house and led me upstairs to my bedroom. I was immediately ordered to strip naked and lie on the bed, which I did without hesitating. She then took several lengths of black rope from her shoulder bag and with expert precision had me spread helplessly on the bed. Finally, a blackout blindfold was placed firmly over my eyes.

“You’ve now been in chastity for me for three weeks. I told you at the end of week one that I’d continue to assess your performance on a weekly basis and I’d decide if you’re worthy of a release during my next visit. Do you think you’ve earned a treat, slut?”

“Mistress, that decision is yours and yours alone. I’m at your mercy and here to please and serve you.”

She inserted the key to my locked cage into the sliding lock and pulled it free. Mistress very slowly slid the cage off my cock followed by the tight back ring.

“Three weeks in and no orgasm. Is that correct?”

“Yes, Mistress,” I replied.

“Good. I’m pleased, but this won’t end here. You know I keep my slaves in long term chastity, which is the reason I accepted your application to serve me.” Her sharp manicured nails dug into the head of my cock as she gripped the tip and kept squeezing. I cried out in pain and my Goddess used her free hand to cover my mouth.

“Hush. I didn’t give you permission to make a noise!” she snapped then grabbed my throbbing shaft. A few light strokes of my erect cock quickly settled me and my breathing calmed instantly.

“See. Good slaves get rewarded. Slaves who disobey me get severely punished until they learn from their mistakes. You disobeyed me during week one and you received your corrective lesson. I can still see the marks. I hope they serve as a reminder not to screw up again.”

“Yes thank you, Mistress. I learned my lesson and won’t do anything to upset you again,” I said sincerely.

“I don’t think you will either. Continue to perform correctly and you’ll earn that collar that I know you crave so much.”

Over a month ago Mistress H and I had a discussion about me becoming one of her collared slaves. She’s a Goddess I’ve admired and wished to serve for years and when she mentioned this opportunity I begged for the chance to prove myself to her.

The powerful dominatrix pushed her knees apart, which forced my legs wide. A thick lubed rubber dildo pressed against my exposed arsehole and slowly entered me. She kept one hand on my cock and stroked it as the dildo moved deeper and deeper.

“Can you feel me, slut? That’s my cock you can feel violating your hole. It’s attached to me, so in a few moments I’m going to start thrusting. I know you have anal experience, so I’m not going to treat you like a beginner. I’m going to have some fun with you and you will not cum until you’re given permission. Do you understand?” I nodded keenly and with a beaming smile on my face responded “Yes, Mistress. Thank you.”

I heard the sound of a rip coming from the end of the bed and a condom was expertly rolled over my cock before the first deep thrust of her cock took my breath away. Her thick rubber cock penetrated my hole and stretched it wide open. With each thrust the cock teasingly tickled my prostate sending euphoric pulses through my entire body. Mistress H softly rubbed the length of my shaft and, combining the anal play and weeks without ejaculating, I soon started to feel the urge to release.

“Don’t you dare cum. I’m far from done with you,” Mistress H shouted as she continued to thrust her hips driving her hard cock in and out of me. She instantly released her grip on my cock and slapped my jiggling balls harshly with her open palm. The pain, although excruciating, actually helped me a lot. The building uncontrollable desire to cum vanished in an instant before she edged me some more with another minute of cock teasing.

The playful dominant lifted my thighs up with both hands and thrust into me again. The change of angle drove the strap-on directly into my quivering prostate and my breathing quickened again. Quickly noticing this, Mistress H gave me permission to cum.

“Come on, slut. I want to see cum fill that condom. Cum for me.”

As she pounded my arse harder and harder I succumbed to my body taking control against my own desire. I wanted her to keep having her way with me, but a few seconds later, thick warm cum shot out of my cock and began filling the condom covering my cock. With each thrust she forced another shot of cum out of me until I had nothing left to give.

“Good slave.” Mistress purred. “I’m not finished with you yet though,” she said as she pulled her cock out of my trembling ass. She angled my cock to the side and slid the full condom off me.

“One final task. Open your mouth nice and wide.” Expecting her to pour the contents of the condom into my mouth I parted my lips and struck out my tongue in anticipation.

“Oh, no, it’s not going to be that easy. I told you when we first spoke of your servitude to me that I’d challenge you. Let's see how you handle this.” Mistress H pushed a rubber coated steel dental gag into my open mouth and adjusted it until my lips were held apart. She removed the blindfold and as I opened my eyes she replaced the used dildo with a clean one. She was wearing a shiny black latex underbust with her large breasts hanging free inches from my face. As I took a moment to appreciate the stunningly beautiful Goddess now straddling my chest she poured the contents of the condom over her new cock.

“I didn’t give you permission to look at me, did I slave?” Mistress H glared at me then lifted one of her thigh high boots over my shoulder to get a better position and in one quick motion thrust her hips up and forced her cum covered cock into my mouth. With my head flat against the pillow behind my head I had nowhere to go and was entirely at the mercy of my devious domina. She fucked my open mouth relentlessly, the thick cum coating my tongue, her cock preventing me from swallowing. My sweaty hands gripped the rope around my wrists and I kicked my legs helplessly. I felt completely violated and used, my happy place.

“Let's see just how you can take my cock. If you’re lucky I might just invite you to my next forced-bi party if you can take my cock deep into your throat. Some of the guys that usually come to have their dicks sucked by my slaves have huge cocks, and you’ll need to be able to take every inch if you want to attend. Would you like that? For me to chain you up naked in the corner of the room with a gag holding your mouth open for anyone I want to fuck your face like I just did to you? I’d order them to cum all over your face and in your mouth then line the next one up to do the same thing until you're full of their cum. If you manage to earn your collar I’ll make you the centre of attention at my next party. They’ll all want to get their hands on some fresh meat. I might even get you in the stocks and fuck your ass while they fuck your face. That’s what I want for you and I don’t think you’ll resist my orders, will you slave?” I shook my head from side to side, my movement still limited by the thick cock in my mouth.

“I thought so. We still have a lot of slave training to do until you earn that honour, but this has been a very positive step,” she said as I opened my throat and her cock edged deeper into my mouth.

“Well done. You’ve earned that release. Now, let’s get that cock locked up again until next time.” She pulled the dildo out of my mouth and released the gag. Her fingers scooped the last remaining drops of cum from her cock and ran them over my tongue. I licked up every drop, swallowed and presented my clean tongue. She smiled, nodded her head and got off the bed to pick up her shoulder bag.

“I think a heavier steel cage is in order for this week. The previous cage was a little too easy, so I want something a little less forgiving this time.”

She pulled out a dense stainless steel chastity cage from her bag and positioned herself on the edge of the bed. Her nimble fingers comfortably pushed my cock and balls through the cold back ring then stuffed my shrivelled cock into the cage. Once the two were perfectly aligned she slid the lock into place and turned the key before putting the necklace holding my key around her neck. It joined 6 others jangling against her chest.

“I’m going to release you from your rope restraints now. Once I’ve released all four you’ll bow down on your knees on the floor. Do you understand?”

“I do, Mistress,” I managed to reply. Her calm and assured manor was utterly mesmerising and I nearly forgot to reply. Thankfully that didn’t happen as I didn’t want to screw up so close to the end of our short session.

With the restraints released I hopped intently off the bed and bowed down on my hands and knees with my eyes facing the floor. Mistress H walked slowly towards me, her thigh high heeled boots now directly in front of me.

“Lick and kiss my boots before I leave. I want them to shine before my next session.” Without any hesitation I knelt forwards and flicked my tongue over the shiny patent leather making sure I didn’t miss any dirty spots. I paid close attention to her heels then kissed them both on the top to confirm that I’d finished.

“Very good. Stay there and don’t get up until you hear the front door close. I’ll return in a week. Slave P will be over on Thursday for your weekly clean. Continue to complete your daily tasks as normal and you’ll be well on your way to earning your collar.” She knelt down and kissed my forehead before standing up and walking out of the room. Her heels clicked on each stair as she descended then left through my front door.

The moment I heard the front door close behind her I stood up and looked at my new chastity cage. A heavy stainless steel fully enclosed cage looked back at me. It was slightly smaller than the last one, but at that moment it didn’t feel less comfortable. I would find out over the next week how easy it would be to clean, but with slave P visiting in 3 days for my supervised clean it would be fine.

Mistress H sends one of our collared female slaves to me once or twice a week (depending on the type of cage she has me locked in) to do a supervised clean. Mistress H video calls me when slave P arrives so that she can monitor the visit. Slave P comes into the house, makes me strip naked, handcuffs my hands behind my back and releases my cock from the cage. She then puts on a pair of latex gloves and makes me get into the shower for a thorough clean. If I start to get excited (which happened on my first supervised visit) Mistress H instructs slave P to turn the water ice cold and forces me to stand in the cold shower until I shrivel up. I’m then told to step out of the shower, the chastity cage is locked onto my cock and slave P leaves.

I got into a warm shower to wash the cum and lube from my face and ass then got into bed. The adrenaline that shot through me like lightning earlier in the evening had subdued and I quickly passed out.

My journey continues.

Lock and key page break

This is the first in a new series of short stories that I've started to write. If you enjoyed reading it please do leave a comment below. You can also read some other chastity stories that I've written here.

I want to say a huge thank you to those of you who have emailed us with compliments for the stories that have been written so far. Mistress K passes on every one of them to me and I really do appreciate it. I'll do my best to write some more soon.

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