Originally Posted By Mistress Tissa
[quote=bdsmlover]I just finished a little intro guide to anal play, which may help you:

https://bdsmlog.mistresstissa.com/a-bit-about-anal-play/


This is an excellent primer. In my many years of sessions I've never really been a fan, but I've had some funny experiences. As a college kid in my second session the legendary Mistress Belle de Jour ordered me to be a training sub. While I was worshipping Belle's fingers (yes, fingers) she was barking orders to the trainee on how to put a tampon up there. It felt like I was about to have a movement. Anyway, after a while the trainee was dismissed, Belle and I did roleplay which distracted me from my discomfort. At the end Belle told me, "Don't take that out until you get home!" I disobeyed when I freshened up in her bathroom, wrapping up the tampon and throwing it away outside.

A year or so later I saw an ad for roleplay. I called and mentioned the "Amazon/jungle" thing and this other Mistress loved the idea. When I got there the Mistress said the Amazon would "rape" Tarzan. Naively I thought I was to be the Mistress' stud. But as the session unfolded I was on the receiving end, being taken digitally... with that same uneasy feeling that something was going to come out. Anal was off my list.

Fast forward to a few years ago. I caught up with a Mistress I've known off and on for a couple of decades. She seduced me into worshiping her strap on orally (with all the precautions). She always wanted to take me "inside out" as she put it and one day took matters into her own hands without much warning. She did it digitally, nice smooth strokes... Soon after I bought my own butt plug and she's used that on me on occasion. But that's as far as I can go. At my age I'm not too flexible down there.