Got emptied out the other week.

For the past year or so, I've been trusted to "empty" myself, but masturbating, with my cage on, every 1-3 months. Generally I rely on having gone 4-8 weeks in general, and frantically rubbing the base if my shaft. If that's failing, I grab my wifes vibrator to help. This time, my keyholder told me she wanted to watch me do this. With live getting in the way, we didn't get time alone for about 10 weeks.

She had me on her bed, while she watched from her comfy chair, and drak tea. After 20 minutes of her mocking me, I was ready to give up. She got out her Hitachi wand and told me to get going. This helped, but it was still another 10 minutes work till I finally managed. She sent me to the bathroom to clean up "My disgusting mess"...

The next week she was over and we were going to run errands for her. She decided that I'd gone over 2 months, and should empty again. This time she ordered me to strip and go into the bathroom. She sat, clothed for going out, on the edge of the tub, and told me to jerk off like I used to. It had been nearly 2 years since I'd stroked myself, and that time I'd had to do it with several needles in my cockhead. This was a real mind f*ck, and really difficult for me, as we'd drilled into me, just what a gross, dirty habit this is, and broken my masturbation habit years back. She watched me as I sat on the toilet, and she told me how she can't believe that guys waste so much time doing this every day, and how self indulgent and childish it looked. Again, I had great trouble cumming. Being locked so much, it was really sensitive to the point of being uncomfortable, and I was really self aware of being watched in the act. More insulting, some very hard nipple pinching, and back to watching, when I finally, mercifully, managed to cum for her. She said it looked like a decent amount, and to clean that shit up, get locked and ready for the errands. I know I came both times, but I honestly couldn't tell you anything about how they felt, other than I was glad it was over.

This was all really unexpected, but with time to gather my thoughts, it's really good to reinforce her feelings about male masturbation and reinforce my training and our roles.

Anybody else have emptying/masturbation treated as a nasty habit? Is orgasm a reward, or more of a necessary duty and part of a maintenance schedule? How do you guys treat the process?

 

I wish I could! 30 years of Crohn's disease and my ass is not good for much. Way to scarred up and painful, which is a huge shame as I'd love to make the switch from pitching to catching, and see what that's like!