Hmmm…could this be the one I bought?

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 wanted to make sure that ass was primed and ready!  I felt safe and comfortable doing this because it’s not like he’s really an anal virgin.  His training was more remedial, just getting him used to having that back door filled up!

Accelerated Ass Play

This week, we went with overnight wear.  Just before he went to bed, sometimes before play time, sometimes after, I’d bend him over and slide one of the anal dilators home.  Then in the morning, I’d have him take it out and wash it.  Each day during the week, we used a larger size, so that, by the end of the week, he had that 2-inch wide, 5-inch long plug deep inside him all night long!  On the weekend, we went for 12-hour sessions – switching to the next larger size every 3 hours.  I gave his ass a workout!

I Think he’s Ready For That Strap-On

He hasn’t seen it yet – but it’s there, packed away in our bags.  We’ll we’re away on our trip, after he celebrates his birthday, I’m going to take him back to our room – where the real fireworks are going to begin!  I’ll slide into that strap-on harness, and get that cock all secured in there.  Then I’ll get him down on his knees and….

Well, you’re just going to have to wait until we’re back to hear the rest of the story.