“If I recall correctly, I’ve been practicing solo chastity since my wife isn’t quite as keen on it as I am. We’ve definitely gotten into more BDSM activities and even some anal play, but she still doesn’t fully grasp the concept. Part of that is because I’m a bit of a rule-breaker without a KH or Mistress to keep me in line and punish me properly, so I haven’t really stuck to the ‘program.’ That was true up until about two weeks ago.
Lately, my job and schedule have kept me from having sex or masturbating much. This gives me plenty of time to watch porn and read materials to get myself aroused, but there’s nothing physical to do with that energy. Tonight, while browsing some femdom/sissy content, I decided it was time to try milking again since it had been a while.
I grabbed this and used a couple of dowel rods taped together as an extension handle for the dildo. I lay down, played some media to get in the mood—it was my first attempt—and managed to locate the spot, feeling those sensations many articles describe. I held a small shot glass over the head to catch the release without paying too much attention to it, just letting it happen for about 30 minutes.
When the time was up, I checked the cup and was pleasantly surprised to see nearly a teaspoon of cum at the bottom. Usually, once I’ve really come, I can’t bring myself to do this again (even though I’ve had worse fluids in my mouth after finishing), but I took the chance to clean up.
I’m sitting here pleased that I succeeded and managed anal play without resorting to masturbation. In the past, doing anal would frustrate me until I just masturbated to completion before cleaning up.
This feels like a huge milestone for me!:) I’m typing this with the plug in place for the first time long-term (I can’t really walk around comfortably with such a large plug and its cheap base). Hopefully, this is the official reboot I needed.”,