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Chastity Stories: Male Chastity and Anal Play #1

Working from home has numerous benefits. You can watch a full Netflix series in a day or as much porn as you like, take long lunches, get up late to start working and generally dealing only with the rules that you put in place yourself.

Today was much like any other Friday. I woke up, jumped on the computer and sent a few emails. Then the overnight orders were packed up ready to be sent later the same day. The weather outside is sunny and I looked forward to a quiet evening in. Then my phone buzzed.

"Put your cage on and leave the key on my desk" was the order I received from my Mistress. Immediately I dropped everything. I pulled out my clear Holy Trainer from our toy box along with a bottle of water based lubricant. Getting the cage on is always the most difficult part as I get very excited and usually get an erection. After taking some time to calm down and let my cock get flaccid I pushed my cock and balls through the ring, lubed my cock and put the cage on. The lock slid perfectly into the hole in the cage and with the turn of the key I was caged. My order had been completed. I messaged my Mistress back with a picture of the key on her desk ready for her return.

"Good boy" was the response I received. "Now make sure my gloves are clean". The anticipation for what was in store for my evening started to build knowing that she wanted to penetrate my ass with her latex clad hands. She might even pull out her strap-on and fuck me if I please her. My cock tried to get hard thinking about her, but the cage quickly put an end to that. I quickly washed her short black latex gloves and left them to dry.

With 4 hours till she arrives back home and walks through the door I had plenty of time to kill. I quickly got all of my outstanding work done, shower, washed the dishes and tidied our bedroom. Mistress demands a clean boudoir to play in.

Whilst I'm doing all of this Mistress sends me teasing messages aimed at causing me discomfort in my cage. They all work. She tells me about the tight latex corset and lace underwear she'll put on to abuse me in and the shiny black fuck me high heel pumps she'll have on to tower over me. Each message ends with an instruction to get another new item out of our toy box and have it placed on the table next to our bed. A cane, a ball gag, rope, handcuffs, my metal collar, an inflatable butt plug and finally, 30 minutes before she was due to walk through our front door, the strap-on and harness.

"2 minutes" is the final message I receive. I've waited all day for this moment and she never disappoints. I wait patiently for the knock on the door and open it without hesitation. She walks in, I remove her full length black coat and hang it up for her before handing her a glass of champagne.

"Kneel" Mistress orders pointing to the floor. I drop to my knees and she places her heeled foot on my thigh, slightly digging her heel into my skin to remind me she's in control. I remove her shoes one at a time and place them neatly next to me.

"You're not going to like what I have in mind for you this evening" she says with a hint of joy in her voice. My cock twitches and I soon feel it straining inside the cage. I know better than to respond without being instructed to do so, instead bowing my head in acceptance. Mistress then walks up the stairs and leaves me on my knees.

I can hear her inspecting the items I was ordered to get out and she walks slowly back down the stairs. She lifts my chin with two fingers and asks me about our safe words. I respond with our usual safe word, places the circular metal collar in her hand around my neck and locks it shut. "Follow" is her instruction as she walks back up the stairs. I stand up and start to follow her, but she stops dead, turns around and points to the floor. "I didn't instruct you to stand up. Crawl. You'll be punished for that".

Once I crawled on my hands and knees up the stairs behind Mistress she closes the door to our bedroom and leaves me sat by the door. She opens it again after a few minutes and forces a shining red ball gag in my mouth, pulls the strap tight and locks it with a padlock behind my head. A blindfold is then placed over my eyes. The next sound I hear is the bathroom door shutting and the shower being turned on. The anticipation is making my cock really ache against the hard cage and the pain is unbelievable.

I hear the shower turn off and hear her drying her sumptuous body through the door. The door opens and she lightly brushes past me before shutting the bedroom door. The next 20 minutes are unbearable. She knows that the wait is torture for me. I can hear Mistress opening her wardrobe door and the sound of high heels on the wooden floor. Again, my cock strains against my cage and the pain makes me bite down on the gag.

Suddenly everything goes quiet. The bedroom door opens and I can feel her looking at me through the blindfold. "Stand" is the command. I rise up to my feet. She walks straight passed me and enters her office. I hear the jangling of keys and she returns to the door way. The blindfold over my eyes is removed and I get to see Mistress for the first time. She has sexy red lace underwear on, her 8 inch black high heels, sultry red lipstick and her hair is tied up in a neat ponytail.

"Remove your clothes" she instructs as she walks into the bedroom. I quickly remove my clothing and stand awaiting my next command. She returns with the black latex underbust corset around her waist that she knows I love. She spins around and I pull the cords to the corset together before tying them in a bow. Her shapely figure turns again and I feel a shot of pain from my cock. The tease and pain caused by seeing her dressed like this nearly drops me to my knees.

Her hand raises and with her index figure she beckons me to follow her into the bedroom. I stand perfectly still as she closes the door behind me. I hear the slow click of her heels on the floor behind me and she swiftly pulls my boxer shorts down to the floor. I'm completely naked except for the tight cage constricting any movement from my excited cock. Mistress circles round in front of me and looks disapprovingly at the pre-cum dripping from the tip of the cage.

Mistress reaches for the metal handcuffs on the table next to her and locks them to my wrists behind my back. She then slowly bends her knees and pulls out a leg spreader from under the bed. My ankles are then locked in place using the cuffs attached to each end of the bar with my legs wide apart. I wasn't expecting this and I immediately realise just how vulnerable to feel. The realisation of what Mistress can do to me makes my legs start to tremble slightly. Recognising this, she forces my head down onto the bed so that my upper body rests on the bed with my legs still planted to the floor.

Mistress walks over to the table and I hear her putting the black latex gloves on. I then feel a tight grip around the handcuffs and Mistress slowly lifts them up behind my back. With one gloved hand she spreads my ass cheeks and inspects my puckered asshole. I feel a well lubed finger penetrate my ass and work its way inside me. "Filthy slut" she purrs. I take it so easily she adds a second finger, then a third. Her smooth fingers slide in and out of me in preparation for what's to come. Soon after she removes the fingers I feel the inflatable butt plug sitting on my asshole. "Deep breath" Mistress mocks before slowly forcing it inside me. My eyes roll in excitement and I bite down again on the gag. It feels incredible when it's all the way inside me. She then pumps it up a few times and I feel it expanding. I cry out each time she inflates it and I hear her laugh with each murmur I make. She then drops the pump and I feel it dangling between my ass cheeks.

The next sound makes my eyes bulge. The sound of a metal cane being lifted is unmistakeable. Mistress places it next to me on the bed and grips my ass in her hands. "This punishment is for disobeying me earlier" she says. She raises her hands and starts to spank me. The latex gloves strike my ass over and over to warm me up. Then she picks the cane up off the bed. 10 strokes to start. I try to scream after each stroke but the gag prevents me. The muffled noises seem to anger her and the next 10 strokes are much harder. The only thing I can do is bite down on the ball gag and take it. My legs are trembling much more now and I do all I can to take my knees from buckling. "Good boy" she says once it's over. I try to thank her but the gag subdues my response. "You don't seem very grateful" she proclaims and proceeds with another 10 harsh strikes. "Thank you Mistress" I scream when it's over. "Better" she says with a raised voice.

Before I have a moment to catch my breath I feel a gloved hand wrap around my exposed ball sack and grip my balls tight. The pain is instant and I drop to my knees. "Up" she demands. Slowly, I rise back up and extend my legs. This time she digs the end of the cane into my balls and I do everything I can to not drop again. I want Mistress to be pleased with me and for her to do exactly what she wants to me without failing her. A few light taps with the cane on my balls invoke an involuntary response and I drop again. Her sadist laugh makes me smile.

My heart's racing and I have a few moments to catch what breath I can with the gag on. The rope from the table is soon wrapped under my arms a few times and around my chest. It's then tied behind me and Mistress checks that it can be gripped from behind. I hear a very familiar sound; the tightening of leather straps.

In a single swift movement Mistress released the valve on the anal plug and pulled it out of my ass. I was breathless for a moment but quickly gained my senses. Her gloved fingers then pressed against my asshole and opened me up, stretching my loose hole. I could feel her cock behind me on my spread legs. She was teasing me and I loved every second of it. Sensing that I was maybe enjoying myself too much she backed away and took another piece of rope in her hands. She tied one end tightly around my balls and the other end around a ring in the middle of the leg spreader bar. Mistress tested the tension in the rope and my eyes watered.

The feeling of her strap-on cock pressed on my asshole soon made me forget about the pain. She loves fucking me and I love being fucked by her. "I'm going to enjoy this" she declares as she slides her hard cock inside me. I clench my cuffed hands and lock my jaw around the gag. The first few thrusts are slow and shallow, then she grips the rope tied around my body and forces her way in hard and deep. It rise up to my tip toes and scream. It feels so good. I can feel my arsehole clenching around her cock and she thrusts ever faster. Each time she hears me yelp with pleasure I feel her heeled foot tug the rope tied to my aching balls. My yelps of pleasure quickly turn to screams of pain and she laughs with amusement.

The thrusts get harder and faster. I can feel my cock dripping in the cage and the newly formed bruises on my buttocks smarting. Mistress spanks me as she fucks into me to remind her submissive who's in control. She groans with each deep thrust and pulls on the cord connected to my balls again. Her cock rubs constantly against my G-spot and I can feel the anticipation building quickly inside me. With a few more hard, deep penetrative thrusts I can't hold it any longer and cum hard. The cum pours out of the hole in my cage and Mistress pulls out of my arse immediately. "Did I say you could cum?" she barks. "No Mistress" I whimper through the gag.

The striking pain inflicted by her hand on my now empty ball sack is indescribable. The first impact was an open palm before she digs her hands into the flesh containing my shrivelled balls. She jerks the rope around my balls down hard and I howl. Drool flows out of my mouth and drips endlessly from the shiny gag. A quick knee from behind to my balls takes me completely by surprise and winds me. I sink to the floor in agony. "You never, ever cum without my permission!" she squeals. "That's my cum and my cock, not yours. Do you understand slave". I'm speechless and manage only a nod of the head. "If you're to submit to me you'll abide by my rules or face the consequences." Out of the corner of my eye I see Mistress take her gloves off, removes the condom from her cock and put on a pair of disposable gloves. She wipes the cum from the bed covers and smears it all over her cock. "If you make a mess you'll clean it up. Filthy slut". Her hands grasp behind my head, unlock the padlock on my gag and pulls it from my mouth. "Now, clean my cock" she ordered.

Without giving me a second to think she pushed her cock into my eager mouth, thrusting it in and out of me with her hands gripped tightly around my head. The cum from her cock swirled around my mouth and down my throat. "I want you to swallow every last drop" she demanded. Once she'd suitably fucked my mouth dry she pulled out and told me to stick out my tongue to be inspected. "Good boy" she proclaimed.

As she sauntered away from the bed, her heels clicking on the floor getting quieter as got further away, I collapsed on the bed. She returned soon after to remove the leg spreader, unlock the handcuffs and turn me onto my back on the bed.

"Thank you Mistress" I managed. "Could you please take my chastity device off?" I asked. She started laughing savagely. "Absolutely not" was her reply. "You came without permission. Your punishment is to have my cock locked up for as long as I see fit. Once you've earned your release I'll unlock you. Not before". "Yes Mistress" I sobbed.

I had no idea how long I'd remain caged, but this was the start of a long personal journey in chastity for me.

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We hope you enjoyed the story and you can buy your own Holy Trainer here.

Comments

missylouise:

wonderful times
thank You for sharing

Apr 17, 2017

Bullcucky:

Awesome story….so hot and perfect!

Mar 15, 2017

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