Jack’s Anal Training – Final Week!
A Challenging Week For Jack’s Ass If you’ve read or followed my Anal Training program, you know that it’s supposed to be 8 weeks. With Jack’s business trips – which lead to his amazing promotion – and some other things going on, we had to ramp things up a bit. I...
Small Strap-on Dildo
As most of you know, Jack has been training for a new strap-on I am going to surprise him with for his birthday this month. He has been stretching out, and has reported on his progress so others could do anal stretching too! Well, after his third report, he had to...
Anal training Safety
Anal training Safety I am taking a break from Jack’s anal training reports for a couple of reasons. First, Jack was away on business, and his training schedule was thrown off. These things do happen. Life gets in the way at times, and these breaks can be a great time...
Jack’s Anal Training – Week 3
My Butt Slut’s Ass Is Opening Nicely Well my voyeuristic pegging pets, we’re onto Week 3 of Jack’s remedial anal training. I guess week 2’s butt plug opened him up enough that the 1.5 inch diameter of this week’s dilator caused him little issue, because he didn’t ask...
Jack’s Anal Training – Week 2
Let’s Widen That Ass So, Jack’s first week of anal training went pretty well. His horny hole hadn’t forgotten ALL the work I had put into it. For week 2, the plan was to move up to the next size, the 1.25 inch dilator. While he followed the 8-week anal training...
Jack’s Anal Training– Week 1
Why More Anal Training? As I mentioned, Jack is going back through my anal training program, using the new anal dilator set we got. I got some questions in email and IM. Mostly, they revolved around this… I thought Jack was ALREADY a butt slut? You’ve told us all...
Jack’s Anal Adventure
I recently blogged about an anal toy Jack had worked up to with his new anal dilator set. I got a few emails asking about the set and how he did it…and one asking if he would do more. In fact this slut was very excited to get his own anal dilator set to begin...
Valentine’s Day Anal Play
It has been my quest to find a toy to tease and please both me and Jack. Since he has been such a wonderful butt slut, and has been practicing really hard (no pun intended) with his graduated anal dilator set, I figured he was ready for a new toy, and honestly, I am...
Prostate Massager Fun
A Butt Slut With A Sensitive Prostate I have known for a long time that Jack has an extremely sensitive prostate. It’s what makes him my favorite butt slut! The other morning, after sitting on his face and getting my day started right – Mistress ALWAYS cums first! -...
Jack’s Perspective On Anal Training
I can tell you all about anal training, but sometimes, it’s more effective hearing it from the bottom… Read what jack has to say about his anal play experiences, good and bad, and what made them better! You Need An Anal Training Mistress Jack says... I had a number of...
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