The Mistress Files Ch. 02

Mistress files chapter 2

This is the follow up to a previous story, The Mistress Files part 1. You don't have to read part 1 for this part. There might be a part 3 if I get enough feedback and inspiration to write it!

As per our previous sessions he had emailed in advance and thrown in a few ideas that he wanted to explore. This time he was really getting a bit deeper and darker and I loved it! My mind spent a couple of evenings prior to his booking thinking over what I was going to do with him.

Eventually Friday evening rolled around and I got ready for his booking. As usual I wore my black shiny thigh high pvc boots as I knew they were his biggest fetish. Next came my black latex corset pushing up my cleavage and some long black latex elbow length gloves followed by some simple black lacy knickers. Some dark eye make up and dark red lipstick and I was done. In the bedroom I had carefully laid out all the toys I intended to use on him.

Right on time the doorbell rang and I let him in. As usual he was dressed smart and immediately asked how I was. The only signs of what he was thinking or any excitement was his eyes looking me up and down and taking in my outfit. Taking the envelope off him with my payment inside I offered him to follow me up the stairs as per usual so he could get a good look at my boots and latex covered bum. Once upstairs I showed him into the bedroom and told him to strip off fully naked and wait for me on all fours and I would return within five minutes.

After the five minutes in the bathroom touching up my make up I walked back into the bedroom to find he had followed my instructions. There he knelt, his dark muscular body waiting naked for me on fours, all his power about to be in my latex covered hands. Even better he was wearing the butt plug that I had commanded him to in the email. Such good subs are hard to find for any pro mistress and this one was my favourite due to his abilities to follow my rules.

I leaned over him making sure my boots were directly in front of his face on the floor. I ran a gloved hand over his back and over his arse cheeks. He didn't even flinch when my hand went over his cheeks, he was learning well with me and becoming comfortable in his submission to me. I carried on down and over his thighs. The muscles firm to my touch from his working out. He was an impressive man but right now he was mine to play with.

I grabbed hold of the collar and leash and firmly attached it around his neck. Now the collar was on him the session could properly begin. I pulled on his leash hard, much harder than I had done in previous sessions. It wasn't his fault I was pissed off but having him on the end of a leash gave me a good way of letting out my frustrations of the day. He crawled towards me, head bowed. I told him to look up at me, to take in my boots and to then look down at my feet.

I told him to start licking all the way up on my boots like he does every session. He threw himself into licking my boot like he always had done. I enjoyed looking at him doing it. Occasionally pulling on the leash to bring him up higher. Once he reached the top of my boot he stopped and looked up to me. I told him he had done a good job and as a reward he was to lick up the inside of my thigh.

He gently ran his tongue around the bare skin at the top of the boot making me moan a little at his soft wet touch. I let him lick up higher until he got near my pussy.

"You may lick my knickers only slave." I commanded him.

"Yes mistress."

His tongue ran over my black lacy knickers making me moan in pleasure. The pressure of his tongue pushing the lace against my clit was delightful as was his hot breath against my pussy. I knew he could smell my pussy and sense how wet I was but at the moment I wanted to keep teasing him, leaving him on the edge and denying him full access to my pussy.

"Stop!" I commanded. "I think you are enjoying this way too much!"

I pulled on his leash making him stumble and gasp a little. He immediately took his position on his knees without prompt. I smiled a little to myself at this then commanded him to get on all fours with his ass up on show. It delighted me to see this well built and well toned man submitting to me and naked on all fours in front of me. His arse was pretty much perfect and his whole body was incredibly fit yet here he was paying me to abuse, use and make him submit to me.

I took hold of the leather paddle on the side and slowly ran it over his arse cheeks. He didn't even flinch such was his submission to me. Quickly I pulled my arm back and gave him a slap of the paddle across his cheeks making him grunt.

"What do you say to your Mistress?"

"Thank you Mistress." He whimpered.

"Good boy! That was just a teaser." I laughed.

"I'm going to give you 10 of these and you will count every one and say thank you. Understood?"

"Yes Mistress." He replied.

I struck the first strike of the 10 across his arse and he grunted again, counted out the number and said thank you. We repeated this perfectly for all ten strokes with me striking him that little harder everytime.

"Well done, you have impressed me with that." I said to him as I ran a latex covered hand over his now tender cheeks.

Before he had a chance to answer my fingers found his butt plug and push on it a little making him moan.

"I know what you have really come here for today." I whispered into his ear.

"You want to be my little anal slut don't you?" I continued as I pulled this time on his butt plug.

"Yes Mistress I do." Was the only words he could get out.

I pulled again on his butt plug and it popped out leaving his dark hole wide open and gaping for me. I stood up and learned over to my dressing table and took hold of my strap on.

"Turn your head and watch me."

He turned and watched intently as I carefully and slowly buckled the harness of the black strap on around my waist and positioned it until it was perfectly positioned sticking out like a real erect cock. I slowly gripped hold of it and started to wank it running my gloved hand up and down the hard rubber shaft as his eyes widen at the sight of this.

"Come here."  I demanded of him.

He crawled over to me and I took hold of his leash and roughly tugged on it pulling his head up level with my crotch. My strap on bobbed obscenely in front of his face his eyes widening at the size of it, this would be the biggest strap on I had used on him so far.

"Come on it's no good just looking at it. You know what to do. I'm sure you've had many women in this position before?"

I laughed as he slowly opened his mouth and I pushed the strap on forward against his lips.

"Lick it first before sucking it."

He slowly and reluctantly stuck his tongue and lick the end of the strap on. I giggled as I watched him try and lick around the head. I pushed forward a little bit forcing the head of the strap on into his mouth.

"Come on suck it properly." I commanded him.

I looked down as this powerful businessman with nothing but a collar and leash on him tried to suck my plastic strap on as quickly and deeply as possible. He slowly bobbed his head up and down the strap on as if unsure on what to do.

"Come on you can do it better than that. I bet that's how you don't have your own cock sucked isn't it." I scolded him.

He took the fake cock a little deeper in his mouth but not far enough for my liking it pleasure. I pulled hard on his leash pulling his head further down on the strap on. He gagged and spluttered around the cock making me laugh at him even more.

"You've got to suck it to make it wet enough to slide into your tight arse." I laughed at him.

I tugged hard on his leash pulling his head up and his mouth away from my strap on. He looked up at me, his wide with lust and submission, his mouth wide open and drooling. I looked down to inspect my strap on.

"Look at your spit on my strap on!" I exclaimed. "You've not taken it very far down your throat at all have you! I think in the future I am going to have make you practice your deepthroating skills!".

"Yes Mistress." Was his only reply.

"Turn around on all fours and head bowed down."

He quickly turned around and got into position. Grabbing a bottle of lube off the side I liberally coated two gloved fingers and rubbed them around his open bumhole making him moan and shake in anticipation. I quickly and gently slipped in both fingers making him groan. I worked them in slowly opening him up some more ready for the strap on. I loved watching his body quiver as I moved my fingers around in his ass as deep as I could get them. I slowly pulled them out admiring his open dark pink opening and stood behind him and squatted down.

I slowly rubbed the head of the strap on over his bumhole. Teasing him with the cold hard plastic life like cock.

"Do you want it in your arse?"

"Yes yes." He begged.

I pushed forward a little, the head slipping inside his lubed up anal ring. He groaned out loudly at the invasion. I pulled tightly on his leash as I pushed a bit more filling his tight arse some more. Despite this being the largest object he had taken in his arse I knew with the right technique and skill by me and his willingness he would be able to take my strap on.

"Come on relax and breathe deeply I know you want this."  I encouraged him.

I pulled back gently and pushed a little harder and deeper. I kept doing this pushing harder and deeper everytime and despite his moans and groans I knew he was loving every part of it. Eventually I manage to work all of the strap on fully into his arse and held deep in him as my thighs pushed up against his arse cheeks.

"Oh my darling sub do you feel full? You have done so well! Can you feel it pushing against your prostrate!"

He could only moan in reply as I moved in and out deeply deep inside him stretching him open.

By now I was really fucking his arse, pushing a little further and harder with each thrust. He was panting hard trying to relax to take it all in. I sensed he wanted it to stop but his mind was not letting him due to the sensations and his submission. With every thrust of my strap on into his arse it rubbed my latex corset more against my clit making me moan in pleasure myself. By now it was all about me and my pleasure and as I pounded hard into him.

I sensed the pleasure he was getting from me fucking him was getting too much and that he was getting close to ejaculation. I slowed down my fucking of him to a slow deep fuck.

"Are you wanting to cum my little strap on slut?"

"Yes please Mistress." He stuttered.

I slowly eased my strap on out of his tight arse marvelling at the way it was left stretched open as it popped out.

I tugged on his leash commanding him to get up. I dragged him over to the full length mirror on my wardrobe and made him face it. He stood there, this tall and powerful man now broken into my submission and obeying my every whim. His erect cock throbbing and bouncing in front of him after all my teasing and fucking.

I went and stood next to him, my strap on jutting out obscenely in front of me. I took hold of it and waved it about.

"Your cock is impressive....but how does it feel to see my black strap on is even bigger than yours." I laughed.

Before he could even reply I moved behind him, reached around and grabbed his balls tightly in my latex covered hands. He groaned loudly and winced as I squeezed harder.

"Go on start wanking your cock."

He started to wank his cock with his right hand as I squeezed his balls with my left hand. His black cock looked so impressive twitching as he tugged on it. The sight of him wanking it in front of the mirror was a massive turn on for me and I put my right hand between my legs and started to rub my clit.

"Keep wanking your cock but don't dare cum yet." I whispered menacingly into his ear as I furiously rubbed my clit.

I watched our reflections in the mirror as we both masturbated. I noticed he couldn't stop looking at what I was doing rather than what he was doing. I smiled as I grabbed his balls harder making him wince. I looked down at his hand pumping his hard cock as I started to rub my body up and down his body. My own climax was building as I rubbed my clit harder and as it started to trembled through my body I gripped his balls even harder. I moaned loudly into his ear as I orgasmed as he obediently carried on wanking himself in front of the mirror.

I stuck my gloved hand underneath his nose telling him to smell it and then shoved two fingers into his mouth.

"Taste my pussy on my gloves." I told him as he sucked on my latex covered fingers.

I pulled my hand out of his mouth and stood back from him.

"Do you want to cum?" I asked him with a mischievous grin.

"Yes please Mistress." He pleaded.

"Stop wanking and put both of your hands behind your back."

He groaned in disappointment as I could tell he was desperately holding back his orgasm but he complied and put his hands behind his back. I snapped on a pair of handcuffs to keep his wrists in place behind him.

"Do you want me to make you cum?" I whispered into his ear as I took hold of his cock.

"Oh god yes please Mistress." He pleaded.

I started to wank his cock slowly at first then building the pace up whilst still gripping his testicles. I was intrigued to see the reflection in the mirror of my hand wanking his big cock as he struggled to hold his cum in. By now he was really breathing hard and quickly as his cum rose once again.

"Do you want to cum?" I asked him again as I really wanked him hard and fast.

"Yes please Mistress." He cried out as I suddenly stopped wanking him and just held his cock and slowly just rubbed my fingers over the head of his cock.

"You may cum now." I laughed as I gripped his balls and his cock jerked violently.

He moaned loudly as his cock shot out his cum as took my hand off his cock completely ruining his orgasm. All of his pent up cum spurted out of his cock onto the mirror as his whole body twitched with release. He cried out in a mixture of relief, pain, excitement and frustration as his cum splattered on to the mirror.

"Oh my look what a mess you have made of my mirror!"

"Yes sorry Mistress." He said apologetically trying to recover his breath.

In truth it had really excited me that not only had I ruined his longed for orgasm but that once he had shot his load the majority of it had landed on the full length mirror in front of him. Quickly my mind came up with an dirty and humiliating task for him that I knew he would secretly love deep down.

"On your knees." I commanded him, "I want to lick clean your mess of my mirror."

He knelt down with his wrists still cuffed behind him, took one look up at me and started to lick his own cum off my mirror. The image of this powerfully well built man licking his own cum off my mirror will stay with me forever. It was a massive turn on for me to make him do this. It's not often a Mistress has such a sub to work with like this. 

I watched his face in the mirror as he tasted his own cum as he licked it clean. I could tell he was desperately wanting me to tell him to stop but I wasn't going to do that. I wanted to see him lick up and swallow all his cum off my mirror. I laughed as I watch his face contort as his swallowed the first drops of the cum he had licked up. He was hating the taste of his own cum, he was humiliated at being made to lick it from the mirror but most of all deep down he was craving to be made to do this by me and totally turned on by it. Even though he was here in a professional context I was turned on by what I had made him do and watching him fulfil the task.

Eventually he had licked every drop of his cum from the mirror and swallowed it all and turned to face me. I bent down, unlocked his handcuffs and motioned for him to stand.

"Well done!" I exclaimed. "This has been the most wonderful session. You may now use the en suite bathroom and get dressed."

"Thank you Mistress." He replied as he walked off naked to begin to return himself to his normal life.