My Master is a very patient man. When he started stretching me out he began very gradually beginning me with slightly larger than average toys and working me up to those butternut squashes over nearly a year.
He guided me through task after task challenging me to push myself when I thought I couldn’t manage them or wasn’t seeing the progress in the same way he was. He gave me the direction and orders and left me to do the work which is exactly how I like it.
So having tightened up a bit recently I was disappointed to have gone backwards slightly but that turned to pleasure when my Master started giving me step by step stretching tasks again as I’ve missed the submission as much as the stretching.
First he gave me a thirty minute task the other day along with videos of him flogging Princess and ordered me to make myself come with the John Holmes toy. It definitely got me started but I was still a bit disappointed that I couldn’t take the toy deeper than I managed.
So last night when he gave me a forty five minute order with the same toy, I had high hopes that it would get me back on my way. I was to make myself come after 20 minutes, 30 minutes and 45 minutes and send him photographs at each stage to show how deep I was taking the toy.
I was determined to please him and show improvement so I started myself gradually with the inflatable toy. A minute each at 10 pumps, 15, 20, 25 and right up to 30 and I was ready to take the John Holmes toy.
I struggled to begin with needing a lot of lube to get it in and only being able to fuck myself very shallowly. But after about 10 minutes, it started sliding into my cunt which began to enjoy being fucked steadily as it stretched. By the time I came at 20 minutes, toy looked much more at home.
This time my cunt wanted fucked hard and fast for the next ten minutes so the toy made me wetter and hornier imagining my Master getting the messages. I enjoyed the feel of the toy stretching me out and filling me up and I actually came nine minutes later I was so ready for another orgasm.
At 30 minutes I had my perennial problem: my cunt was more than willing and my arms had given up being able to fulfil it. I stuck the toy to the wall and fucked myself from behind with it, pushing back as deeply as possible onto and remembering that playing this way with it on my Master’s orders made me squirt for the first time ever.
But tonight it wasn’t enough to push me into an orgasm no matter how hard I pushed against it. I took the toy down and rode it hard until the bed and my legs shook and I played with my clit piercing and I came hard with the toy buried deep inside me.
I rolled onto my back holding the toy inside me and was amazed to see how deep it stayed after three orgasms and 45 minutes of play when the rest of me couldn’t barely function.
I definitely felt like I’d made progress at that point and my Master seemed to agree telling me I’d done well. Hopefully I’ll be ready for his fist again soon…