We all (all the mistresses, that is) have our favorite customers or clients. Some of us love the sissies the most, some adore the cuckolds, for some it’s the chastity sluts. For me, it’s a combination of all sorts of kinks and fetishes. But, I do have favorites. This particular favorite has been my customer for almost 16 years now.  I have grown to adore her, and we speak weekly if possible.

I have taken Michele from a chronic masturbation slut to a chastity slave and then transitioned to a panty wearing, cock riding (dildo riding) and eventually even a dildo sucking sissy. I have had help from other mistresses along the way, and I enjoy showing Michele off to other mistresses.

Michele has become a legend in our circles; her transformation is often discussed during private gatherings. Her moans of pleasure and ecstasy are admired by all who talk to her.

When Michele first reached out to me, she was struggling with a compulsive masturbation habit. She found it impossible to stop. She needed my help.

She was masturbating several times a day, and she admitted it was getting in the way of her work. But she couldn’t seem to control her urges. So, we started slowly. First, she had to go an entire 24 hours without touching her cock. Then it was increased to a few days. Slowly but surely Michele went from being a chronic masturbator to being the ideal obedient chastity slave. Her name was not Michele at this point though.

We didn’t discuss the idea of her embracing a more feminine role for quite some time. However, one day I brought up the topic of her wearing panties and asked her how she felt about that possibility. She reacted with breathless excitement. It was clear this allowed her to express her sexuality more fully, so we continued exploring it.

Naturally, we started with a simple pair of soft silky panties. Michele was instructed to wear those panties to work and to start masturbating and edging regularly. NO ORGASMS were allowed, not without my permission. This is when she made her first mistake.

Becoming a chastity slave involves a lengthy and challenging process, often fraught with obstacles. When I told Michele that a “release” was coming up, she was thrilled. By then, she had gone several weeks without one. Unfortunately, I was unable to keep our scheduled release appointment, leaving Michele to her own devices. She decided to arrange her release with another mistress, which led to quick and severe punishment from me. Admittedly, I hadn’t explicitly forbidden her from doing so, but I hadn’t given her permission either. Michele quickly learned not to disobey the rules or her mistress. Her punishment included writing my name on her body with a permanent marker and wearing her panties for an indefinite period. I believe there was also spanking involved but this was many many years ago. Additionally, her chastity was strictly enforced, and any release was no longer an option.  For a LONG time.

I will continue to tell you more about Michele and how she has become a full fledged cock sucking and dildo riding sissy.  But, you’ll just have to wait til the next installment.