Be brave. Take risks. Nothing can substitute experience.

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I wonder how many submissives have been tasked by their dominant with anal stretching?

Both of mine required this of me during my time with them. It was a task that I relished because anal play is a particular weakness for me…. It was my first step outside of “normal” sex at the tender age of….um….16. I have always loved it, and since beginning to stretch and train in that area play has been even more satisfying. Since learning to cleanse myself the prospect of ass-to-mouth has been an achievable fantasy, and I had shared this perversion with MrN. Because I was pushing against my hard limit of scat the risk felt really taboo, but I knew that I would never have to go there if it was dirty.

So far so good, no mishaps with my cleaning routine, and a gradual increase in the depth and girth of stretch.

MrN was happy and I was happy. Things were progressing nicely. And then we both had an impromptu evening; his partner was out for the night, and my children had a surprise overnight with their dad. He asked me to be available for him at 7.30. He told me he would be pushing me further, and I should prepare myself for all eventualities. There was the problem… I was working until 6 and had an hours drive home. There would not be enough time to clean thoroughly, and doing half a job was worse than not doing it at all. After checking if there was any way out of work sooner and realising there wasn’t, I sent him a quick email outlining the problem I was facing.

His response was that if it came out dirty he expected me to clean it.

“I’m sorry but, as discussed, that is a hard limit, I will not be doing that” was pinged back immediately, and he acquiesced. If it was visibly dirty I wouldn’t need to suck it clean. There had been a brief moment when I thought I should not have said anything, just gone along with his request. But the reason I (we?) have fixed limits is because we know what we are not willing to do, under any circumstances. And making myself heard was a new skill which I had been working on, with both P and H. Now that I had enough self-confidence to speak up, I wasn’t going to stay quiet if I needed to.

The drive home was good, my mind filled with impure thoughts about the approaching session.

I still didn’t know what it was going to be: a plug? a vibrator? a selection of pens?Wondering about all of the possibilities for the evening it is amazing that I got home in one piece! After freshening up and having a quick bite to eat it was time to catch up properly. I already knew that it would be an anal training session, but I was not expecting him to request I find one thing larger than my largest plug which I would be able to insert without damaging myself. Frantically searching my home I found my way to the kitchen and rummaging through my utensil drawer I found my rolling pins. I had two, one with corners at the end, and one with curved knobbly ends. The former would damage me, if I could even get it past the entrance. The latter was a winner. I chose to sheath it because… well… health and hygiene!

My choice went down well with MrN…

…and with lube, patience and a firm hand I managed to exceed my expectations. But then came the withdrawal. Oh dear! I’m sure you don’t need me to elaborate further than it not being clean. Safe in the knowledge that I had fought my corner and I could just rip off the condom without repercussions I decided that it was now or never. And how could I say that it was a hard limit if I had never tried…. It may end up being an amazing experience, in the same way that pee play had been, maybe? With my eyes raised to the ceiling with an all too familiar smile, questioning my sanity, I did it.

I cleaned the rolling-pin!

Actually, I didn’t fully clean it, but I did enough to cement that hard limit into place. As always I had pushed myself past what I was comfortable with, exceeding my expectations and pleasing MrN in the process. He had respected me and my limits, when I had reminded him of them, I had found it in myself to try something which I had would never have done but… I’m a curious girl.

The next week P decided he needed a rolling-pin… Guess which one he took. 

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If it scares you it might be a good idea to try.

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The saying “Be careful what you wish for” comes to mind as I continue on with my memories.

Actually the exact phrase that comes to mind is Be careful what videos you save to an xHamster account that you share with your Dominant, but it doesn’t have quite the same ring to it. I have mentioned before that MrN wanted me to set up a shareable page on the popular porn site xHamster and that I had one already set up with videos of things I was curious about. When we had our next scheduled evening there was part of me which wished I had cleared out the account before sharing the log-in details, started with a clean slate with him. While I was trying to maintain concentration on the conversation, with a medium butt plug in place, he brought up one of the videos I had saved a while back…

It was a lady who was fisting herself, and she looked like she was really rather enjoying it.

He asked what had inspired my choosing that one, so I came clean. When I had started on my journey with Sir he had asked about fisting, and I said I would try but was scared as I didn’t think it would be possible for me. I may be a mum of two, but they were both born by caesarean! So I had taken to the internet for research and inspiration, following a trail of filth through stretching and fisting, anal fisting and rosebuds, finally ending up on self-fisting. The video I had saved (and watched over and over to make sure it was real, obviously) was of a young lady getting into an uncomfortable looking position, and actually managing to insert her whole hand into vagina. The faces she pulled while the video went on were not particularly alluring, but the fact that she could do it made me excited that one day I may be able to do that too. And if I could do it to myself…? Well, someone would be able to do it to me.

Why don’t you get started then? he asked me.

He made a very good case, I could take the time that I needed to gain flexibility and also to stretch myself. He didn’t mind if it took a while, but he would like to see that I was trying. The facts were that I had saved it myself and wanted to do it even though I was scared that I wouldn’t be able to. These made a good enough reason for him to ask. Not including his desire to watch me in my very own video for him… complete with those faces, which were unattractive to me but had the opposite effect on him.

That was all the incentive I needed.

At the time I was slim and fit, with very little excess tummy and a decent level of flexibility and strength. I worked out that if I wore my killer heels and perched on my bed the angles all made sense and I could reach where I needed to. It helps that I am partially double-jointed, the only use I have found for this oddity of my body (aside from being able to win hands-on-the-floor competitions at the pub.) Confident that I could reach I started working on stretching myself so that my hand would fit. The reading I had done focussed on fisting someone else. Did you know there is a Facebook group for fisting, complete with safety guidance and technique discussions??!! Because of the angles I wouldn’t be able to fully twist my wrist at the halfway point…

I was just going to have to work it out for myself, google just wasn’t ready for my curiosity!!

It took me a couple of weeks, with regular stretching and attempts, to get to the point where I thought it may be possible. I had been keeping MrN in the loop as per my progress, and he was encouraging in the face of my scepticism. I still didn’t believe that this would work. So I set up the camera, got my heels on and perched on the edge of my bed. Using my wand to moisten me up a little I used insertables to stretch myself open, and once I had an orgasm there seemed little else to do but go for it. I lubed my hand up and started.

Feeling the ripples from the preceding climax around my bunched up fingers was quite arousing in itself.

Getting to the knuckles I started to pull my fingers into a ball and managed a slight twist in my wrist. It had the desired effect of drawing the rest of my hand in, like a corkscrew. I was so surprised that I had managed it. And I was so full, I could feel my arousal all over my hand now, as I clamped down on myself. It is an indescribable sensation, and had I been more comfortable  I would have stayed there longer, but I was starting to get cramp in my side and had to remove my hand. Taking a deep breath and feeling my overstretched muscles return to size I was left with a sense of calm. The kind of peace that I associate with deep sexual satisfaction. And while the video was uploading for sending to MrN I enjoyed the company of my Doxy for a little longer, and floated off in my little bubble of joy.

The feeling of achieving a long-held goal is powerfully erotic for me, and knowing that I had pleased someone else as well… I was one happy submissive.

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