Master Richard Trains Me
Copyright© 2021 by CD_Pauline
Chapter 2
BDSM Sex Story: Chapter 2 - An Introduction to Master Richard training me, a submissive cross dresser
Caution: This BDSM Sex Story contains strong sexual content, including Ma/Ma Consensual CrossDressing True Story BDSM DomSub Humiliation Spanking Oral Sex
3 Second visit
Master Richard trains me – 2nd visit
Following Master Richard’s first visit we messaged each other several time and He said that He had enjoyed using me in the way that He had done, which pleased me, and that He intended to push me further in the future, which made me feel a mixture of: gladness, because He wanted to visit again; apprehension, because I didn’t know if I could live up to what He planned to do and excitement.
Mater Richard told me that for His second visit He wanted to be able to secure my hands above my head. He suggested a hook in the lounge ceiling, this was not possible for me to do, but I found a way that He could secure my hands above a doorway between the lounge and the hallway, I hoped that Master Richard would find this acceptable.
We arranged a second meeting less than three weeks after Master Richard’s first visit to me. For this visit He told me that He wanted me in my black leather skirt and red top. Again I prepared myself for His visit, putting on a red basque and panties with black stockings with a red seam under my leather skirt and red top. Red heels and my brown wig finished my attire off. I felt far less nervous than for Master Richard’s first visit as He wanted to return, but still apprehensive as to how Master Richard would use me for His pleasure.
I greeted Master Richard with a curtsey I again lead Him into the lounge where He collared and cuffed me. Then He put a ball gag in my mouth secured by a harness. He told me to get on all fours so that He could use me as a foot stool while He drank a drink that I had made Him. Once again I felt very humble and He had re-enforced His position over me.
His drink finished Master Richard stood up and told me to remain where I was. He lifted my skirt to inspect my panties then, to my surprise He lowered it.
Master Richard set up His camera and took out His three tailed leather strap. With my leather skirt still covering my bottom He began to strap me. I was surprised at how little protection my skirt gave me from His strap. With a ball gag in it made counting the ten strokes difficult and I was soon gurgling into the gag.
Satisfied with the initial strapping Master Richard removed the gag and told me to undress Him, reminding me that I knew what to do. I slowly removed each item of His clothing kissing His body working down to His feet which I kissed and sucked His toes. I spent a long time worshiping His feet, sucking each toe separately and licking between them before Master Richard instructed me to work back up to His lovely cock. Master Richard videoed my licking and sucking the head of His cock before taking it deep into my mouth, and looking up to the camera to tell the world how much I enjoyed sucking His beautiful cock. I told the camera how much I love sucking Sir’s beautiful cock, because it gives Him pleasure; that I love licking down the side, licking the shaft and licking the end, giving Him pleasure; and when I take it right in my mouth, He loves that. As I spoke each phrase to the camera I demonstrated the actions, and as I took all of His beautiful cock into my mouth, I could hear Master Richard moan with pleasure, that truly gladdened me.
Master Richard stopped me pleasing His cock orally before He climaxed and told me to kneel on the foot stool with my hands on the floor. I knew that in this position my bottom was well presented for whatever He was going to use to punish me. Master Richard lifted my skirt and lowered my panties before I heard the swish of His flogger. He swished it in the air several times before He landed the first stroke across my bare backside. I had counted and thanked Master Richard for seventeen strokes before He paused. Then I heard the familiar whooshing sound of Him rotating His flogger and knew what to expect. Master Richard was swirling His flogger in such a way that is was going upwards towards my exposed bottom cheeks and perineum catching me with just the fast moving ends of the sixteen, thirty centimetre long tails adding to the sting and heat making me moan with the pain. He stopped then I heard the whooshing sound even louder as Master Richard swirled His flogger even faster, the anticipation of the sting was excoriating. Slowly He moved the tips of the tails closer to my exposed upturned bottom whipping and stinging me even more and extracting even louder gasps from me. Three more strokes, all of which I thanked Master Richard for, across my already warmed cheeks finished the flogging.
Master Richard ran His hands over my bottom assessing the warmth before telling me to get off the stool and to kneel on the floor with my legs apart. I Heard Him go to His bag of toys, but knew better than to look at what He was doing. Then sensed Him moving behind me. He took hold of my balls that were hanging exposed between my legs and attached His parachute ball stretcher to me and gave it several hard tugs stretching my balls back and down. This was another first for me as I had never experienced this sort of punishment before.
Master Richard decided that it was time to try securing my hands above the door way. He seemed pleased with my efforts to provide Him with somewhere to fasten my hands to and soon had my wrist cuffs secured as high as He could facing into the lounge with my naked backside towards the hallway. I knew that in this position He would be able to flog and punish my already warm bottom without hindrance of the doorway. Master Richard then lifted my skirt up to my waist exposing my backside and aroused cock and balls with the parachute harness in place and the chains from it hanging down. I felt quite helpless in this position and knew that I just had to trust Mater Richard. He took a couple of photos of me like this before He put a blindfold on me, so that I could not see what He was going to do.
Master Richard decided it was time to add some weight to the chains of the parachute ball stretcher and I felt my balls being pulled down. It was only later; when I saw the photographs Master Richard had taken, that I saw that He had attached a one litre bottle of water to the chains. I had never had my balls punished before and this was a new source of pain for me, but was not a pain I could not endure.
I felt Master Richard move past me from the lounge into the hallway. Being blindfolded and having sight removed heighteners all the other senses and I could hear Master Richard moving around behind me. I had no idea what to expect. Master Richard seemed to take His time increasing my apprehension, then with a whoosh I felt His flogger land across my naked bottom. I gasped a “one thank you Master Richard, Sir” before a second stroke landed on my unprotected backside. Master Richard delivered 10 strokes, each one harder than the previous one, all of which I counted and thanked Him for. Then He stopped. I pricked up my ears expecting to hear the whooshing of Master Richard swirling His flogger around, but it didn’t come. Instead just the sound of His feet and His breathing as He moved close to me. Then, suddenly and without warning, I felt a slight prickling sensation on my by now hot bottom. I had no idea what was causing this new feeling, it wasn’t like the pain of the flogger or the paddle. I felt like many small ant bites as He moved the source of this new sensation slowly across my bum cheeks. Master Richard told me that He was using His pinwheel on me. It felt as though He had covered all of my bottom with the wheel before He stooped.
I felt Master Richard go past me into the lounge, so He was now in front of me. I could hear Him moving around, but again I had no idea what He was doing. Suddenly I felt something sharp at the base of my cock as He began to use His pinwheel on my aroused member. He slowly moved the wheel up towards my cock head, videoing it as He went. Then He ran the pins over and around the head of my cock. Again this was something I had never experienced before, it was that strange mix of pain and pleasure that is so difficult to explain as Master Richard proved His skill with the instrument recording the action in close up.
Master Richard stopped running the wheel over my cock head and removed the weight from my balls. Then I sensed Him move away from me. Then nothing, I could not hear Him nor feel Him. I had no idea what He was doing, I tried to listen, but nothing until I felt Him move past me through the door back into the hallway. I could hear Master Richard doing something and I was expecting to feel the sting of one of His instruments, but NO, Instead I felt Him press something cold against my bum cheeks, just one something on each cheek. Then I felt Master Richard move back past me into the lounge. I thought that maybe Master Richard had forgotten something and I was expecting to feel Him move back past me, but He didn’t.
Suddenly I felt my bum cheeks twitch, but without any control from me. The feeling became stronger and more painful as the twitching increased. Master Richard was using His E-stim on bum. Several times He stopped and started the machine using different settings giving me different sensations of pain and making me twitch in different ways. What I couldn’t see was that Master Richard was recording my actions for Him to view for His pleasure and to share on His Flickr page ( https://www.flickr.com/photos/145970285@N02/ ).