Jack Gets Pegged
I Got Jack A New Strap-On Well, you know where the whole Jack’s Anal Adventure was leading, didn’t you? I had told you I was going to re-pop his cherry on his birthday, and that day had finally arrived. We were heading back to the good ol’ US of A, so we had the...Cuckold Anal Play
I Popped Jack’s Born-Again Anal Cherry! But, you’re going to just have to wait until I get back from my vacation to hear all about it. I’m such a tease aren’t I? I know you love it, don’t tell me you don’t. Anyway, while I’m away, let’s talk about cuckold anal...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...
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