The build up to last weeks session had its ups and downs. The original session booked had to be cancelled (for very good reason), but it’s cancellation had left me feeling disappointed and a bit down. That is a very selfish response I know, but when you look forward to seeing Mistress as much as I do the feeling is inevitable. We agreed another session date and I got on with normal life.
It was a couple of days before the session that I started to get texts from Miss Deelight. They seemed innocent enough to start with…
How was I? How was her cock? Was I looking forward to the session?
Have we ever tried anal?!!
The truth of the matter was that I had never tried anal with Miss Deelight, or anyone else for that matter. I guess for me it was the final step into total submission that I had never been willing to take. But now Mistress was asking about it. I know from past experience that what Mistress asks about, she tends to get. I responded as I knew I must and told her that I was now willing to take this next step.
This was obviously the opportunity that Mistress had been waiting for. I started to receive a series of pictures and texts about what she was going to do to me that sent me into a pre-session tailspin. Her cock which is now locked in its chastity cage came back to life and at night sleep came only fitfully between thwarted attempts at erections. I was now firmly back under Mistresses control.
The day of my session arrived. This was to be my longest session ever. We had originally agreed that I would be at the HOD for 2 hrs but then agreed that I should actually arrive an hour and a half early to be restrained whilst Mistress prepared for the day ahead of her. This would be the first time that I had been restrained and left for a period of time in advance of session. It sounded like heaven to me and so I looked forward to experiencing it.
I entered the HOD when instructed to do so and locked the front door behind me. Mistress had informed me that I would find her in ‘scruffy’ clothes as my proper session wasn’t due to start for another hour and a half. The site that actually greeted me was Mistress looking gorgeous in tight jeans and an even tighter fitting top. For me this was as teasing an appearance as any pretty lingerie could provide. I have to confess that I desperately wanted to wrap my arms around her and hold her body next to mine. But I knew that this would never be allowed and so I would just have to control myself for fear of the punishment I would otherwise receive.
In a way therefore I was relieved when Mistress instructed me to put my hands behind my back in order to secure them. Today she used a metal device that I had not seen or experienced before. Mistress knows that I can’t resist trying to escape from any restraint she uses. Today she seemed absolutely confident that escape was impossible, and she was right. Any attempt to escape was met with the pain of cold steel digging into my wrists and the restraint just clasping more securely. I was ordered to lie on the bed whilst Mistress secured my ankles together and then to the bottom of the bed. And this was how I was left for the next hour and a half. Totally helpless and alone except when Mistress came in to check that my circulation was ok. I found myself longing for her footsteps on the stairs so that I could enjoy the sight of my captor, even for just a moment. Each time that Mistress walked into the room I had to cope with the torture of knowing that I could look but not touch. The cage that I was still wearing was by now was causing me much discomfort as my cock tried to break through it. I asked Mistress if she would remove it for me. She just laughed and ignored my request.
Eventually Mistress appeared at the door again but now she had changed and I knew that things were about to get serious. She was wearing black lingerie and a silk top and my normal pre-session fear returned. She informed me that we were going to play a game. It would involve me rolling a dice. She had prepared a list of 6 tasks and activities. The number rolled would determine what would happen for the following 15 minutes. Mistress informed me that there were two activities that I would enjoy and four that I would not. The odds were not in my favour it seemed! I nervously rolled the dice for the first time. Mistress looked at her list and looked mildly disappointed. Apparently I had got lucky. The first activity was for Mistress to tease my cock for 15 minutes. Mistress told me to remove my chastity device in order that she could undertake the task.
I was instructed to stand in the cage with my arms above my head, Mistress secured my wrists to the top of the cage applied lotion to her hands and started to work away at my cock. This is what I had been dreaming of whilst locked in my cage for the previous two and a half weeks. It felt sublime. In no time at all Mistress had me on the edge of orgasm and longing for completion. But each time she would stop and allow the urge to briefly recede before building me up yet again. Over and over this happened until my cock felt as if it was going to explode. It was almost getting too much to bear and I was close to begging her to stop when Mistress declared that it was time to roll the dice once again.
Mistress looked so much happier with the outcome this time. Apparently I was to put on the maids outfit, my ankles would be secured with a spreader bar and I was to do the dishes and vacuum the downstairs area of the HOD. My incentive? Do it well and I would retain the possibility of an orgasm at the end of our session. Do it badly and it was not going to happen! How did I find this experience? In all honesty it is not my thing. We are all individuals in this slightly unusual world that we sometime inhabit. It is just that, for me, it is not a turn on. The best thing I can report about it is that Mistress seemed to thoroughly enjoy the spectacle that I provided her with. Certainly she laughed a lot at my expense! Thankfully Mistress seemed to approve of the standard of my work and a happy ending to the session was still apparently a possibility. But the dice needed to be rolled a couple more times before this might happen.
The next roll of the dice produced the outcome I had feared most, anal. Another ‘first’ awaited me.
A mischievous grin appeared on the face of my Mistress as she ordered me to lie on the bench. I was strapped securely in place and Mistress ominously started to assemble the items she needed for the next 15 minutes. I had been instructed to collect a knobbly looking probe from the cabinet upstairs which now sat on the trolley alongside a condom, lubricants and gloves. My sphincter tightened involuntarily. I was instructed to relax and to allow Mistresses gloved and lubricated finger to penetrate my rear passage. She found her way inside and I gasped as I was violated for the first time. I felt confused at this new sensation. Mistress probed further until she found my prostrate and started to massage it. I experienced a sensation in my cock not previously encountered. It was somewhere between arousal and the desire to pee. On balance it was pleasurable. Happy at her progress I heard Mistress whisper that she would now use her thumb. Again she was happy with progress and so next she covered the knobbly probe with a condom, applied lube and gently pushed it inside me. I am still unsure of what happened after this. I do remember that I found myself whimpering in pleasure but strangely close to tears as Mistress manipulated the probe inside me. Whatever Mistress was doing to me it provided pleasurable sensations with an intensity that I had never previously experienced. I do remember that at some point whilst this was going on that Mistress asked me how submissive I felt. I have no idea if I answered her then or not. And so for the record, yes Mistress I felt very very submissive at that point. Thank you.
I rolled the dice for the fourth and last time. The next 15 minutes were to be spent strapped to the bed whilst Mistress enjoyed herself controlling my breathing with her gorgeous backside sitting over my face. Whilst I had enjoyed the sensation of face-sitting before this would be the first time that I had experienced it in this way. Mistress secured my wrists and ankles to the bed and climbed up over me and lowered her bottom onto my face. It was a lovely sensation as she wriggled herself into the correct position to prevent me taking a breath. And that is where she stayed until my convulsions told her that I needed to take breath. She would briefly lift herself allowing me to take half a breath before shutting off my supply once again. It was at this point I realised that the more she made me struggle the harder my cock was getting. I think Mistress must have noticed this as well as it just led her to push me further and further. It is at the point where you believe that you can take no more, and you feel Mistress push down still harder and tell you firmly that she is not going to get off until she is ready to, that you realise that you are totally helpless. My lungs and my brain were telling me that I needed Mistress to stop. My cock however was telling her in no uncertain terms to carry on.
It was at this point that Mistress decided that she should combine two activities at one time. Thank goodness she is a woman and can multi-task. She turned and faced the bottom of the bed, and whilst continuing to rob me of air with her backside she went to work on my cock. Following a period of fabulous edging she treated me to a wonderful orgasm – but there was one final ‘first’ for me to experience that I had not anticipated. Mistress gave me a brief but excruciating taster of what ‘post orgasm torture’ feels like. She then suggested that in our next session she should bring me to orgasm at the beginning of the session before torturing my cock for the remaining time. Personally I think this is a terrible idea. But then its not up to me.
The session concluded with Mistress clicking the padlock shut on the chastity cage safe in the knowledge that her property was locked away safe and sound until my next visit to HOD in a months time. I left with a smile on my face and the realisation that the next 4 weeks would pass by very slowly indeed.