Written by AJ1959

29 Dec 2013

Master N started my training gently enough. He encouraged me to masturbate and when I had cum to take photos and send them to him. To describe to him the pleasure I had experienced. Soon he told me to apply a peg to each nipple and then to masturbate. As I rubbed my clit my arm would catch the peg on my right nipple. Not only that, as I have rather large breasts and nipples, the act of masturbating would make my breasts jiggle as I rubbed my clit and so the pain from the pegs on my nipples was shooting through to my pussy. As I became closer to orgasm I was physically squeezing the pegs to induce the pain, even twisting them and it felt so good. I wanted to have something inside my cunt though at the same time. I sent my report to Master N with the pictures. Soon Master had allowed me to progress to more than one peg on each nipple, and the pleasure this brought me was exquisite. Each time I would send Master photos and a report. If my report was not sufficient, Master would punish me to make me think about the experience. My training progressed to applying pegs to my labia AND my nipples. This hurt so much - at first I didn't think I would be able to take the pain at my pussy, especially as I was to masturbate with the pegs in situe. Now it wasn't just the pain from my nipples as I rubbed my clit, but the pain of the pegs on my labia. However the orgasm I experienced was mind blowing. No longer did I want to put myself at risk by meeting other men, I was happy to wait for Master N to contact me and give me my next task. I was allowed by Master to masturbate and use my vibrator with the pegs attached to my pussy lips. Oh wow - I really just wanted him here fucking me with my vibrator as I was tied spread-eagled to my bed, but that wasn't to be. It did add to my pleasure though to be thinking of him doing it to me. My orgasms were fantastic.

Master knew of this and so he never instructed me to do anything anal. However, one day Master told me that my training was near completion but if I wanted to really experience the pain/pleasure there was one final area I needed to receive instruction in, but it would have to be my choice. The area was anal. I agreed and he started my training. I had a smaller vibrator that was to be called his thumb and I was to fuck my arse with this one. Using some anal lube proved to make this easier than I expected and I loved the feeling of having the vibrator shoved up my arse, turned on whilst I masturbated. Pictures and reports were sent to Master. Unfortunately Masters thumb broke and I didn't have enough money to purchase another. Now I had to use my larger vibrator. The pain was undescribable as I tried to insert this large vibrator into what had recently been a virgin arse! Master allowed me to use some lube, and instructed me to send pictures. The pictures I sent only served to prove I had not inserted it all the way in! Master replied as a punishment I was to push it all the way in and then send photographic evidence.

I always complied, not because of fear but because Master had always been good to me and kind with me, except when punishment was needed. However, whenever Master delivered punishment, he was always very careful to ensure I fully understood why I was being punished and what I had done wrong. Always I was to provide a full written report of how I felt when I was carrying out his instructions, how I felt during punishment and afterwards. I was also to provide photos and I loved doing this for him. I had never met him, seen his picture or even hear his voice, but I loved and respected Master and knew he only ever had my best interests at heart. His training was ALWAYS thoughtful and caring and NEVER cruel or vicious. Any training I undertook was always with my consent - he always gave me the choice of what I would or would not do.

In my next part I will tell more of my anal experiences and my ongoing training with Master N whom continues to allow me to be his sub.