A renewed anal focus

As will occasionally happen I have recently been experiencing a few personal issues that have caused a bit of stress in my life. Ms Lee has been very supportive, once again demonstrating her unique approach of caring dominance. Understanding my situation she has allowed me some latitude, but has made it clear that this is not an excuse for me to slack off in my devotion to her. I have continued my duties as her faithful panty washing boy, carefully cleaning the panties that caress her everyday. I also continue to assist her in other ways. I am not sure if it is intended to address my recent stress, but she has also introduced a renewed focus on my anal submission.

During a recent conversation Ms Lee had asked me about my fantasies and I admitted that due to my relentless, extended chastity I have frequently found myself thinking about anal stimulation. Ms Lee’s expectations seem to deviously lead me in this direction. While I am not allowed to touch myself in a sexual manner she does allow one ‘exception’ – I am always free to stimulate my prostate using an anal plug or dildo. The longer I am in chastity, the more desperate I become for any sort of sexual stimulation. But anal stimulation does not provide me anything close to the pleasure and release that I used to derive from wanking like a teenage boy. Instead it leaves me more frustrated than ever, increasing my desperation in an endless cycle. While I do not derive any real complete satisfaction from my anal stimulation I do hope that my desperate attempts please Ms Lee.

One evening after Ms Lee reintroduced the focus on my anal stimulation I inserted my anal plug before I went to bed for the night. I thought I was going to go straight to sleep but I soon became badly distracted by the plug in my rear. I found myself clenching my rear and enjoying the pressure against my prostate. It was quite maddening as I desperately desired a release but the plug did nothing more than tease me. I continued to press against my plug for quite some time before I finally slipped off to sleep, with thoughts drifting in my head of being taken by Ms Lee’s strap on.

I woke a few times during the night and each time I immediately began clenching my rear and pressing against the plug. When I woke in the morning I was so frustrated and excited that I immediately got out my Bigger Tool and proceeded to attempt to milk myself. I was not able to produce anything, but I certainly enjoyed trying. For those who might not be familiar with my Bigger Tool, it is a large, 8 inch long dildo of the sort that a woman would ordinarily use. I had initially began my anal stimulation using one of the slim anal massagers that are popular, but it amused Ms Lee to have me graduate to a ‘bigger tool’. A tool which is much more substantial than my own inadequate member which has been shrunken further as a result of my constant, extended chastity.

Ms Lee now expects me to experiment with different sized and shaped anal toys. I currently have a few standard butt plugs as well as my two anal stimulators. If anyone has any suggestions I would be interested to hear about them.