Punishing is one of my favorite parts about having such a dedicated sissy boy. I actually hate calling her a sissy boy because she is more feminine than I am.

Sissy boy or not she was not behaving in accordance with our agreement. It was simple, no masturbating and cumming unless she requested. Now, I’ll admit I slacked off a bit so the fault is partly my own. Most submissives regardless of gender or association with test the boundaries. This needed to be rectified immediately.

Last week she came to me admitting she had masturbated and came after I gave strict instructions not to. Because I am in a D/s relationship in real life I have had exposure to some uncomfortable punishments. Being that it is phone sex and I am not there in person to correct poor behavior, I dug deep. She would do what I asked no matter what.

If I learned anything, she thrived on being punished. My sweet tone went to stern and assertive when she called. Since she broke the rules I gave her a list of items to purchase, one being a ginger root, stockings, panties and matching garter. I told her to peel the ginger root and shove it into her man pussy.

20 minutes was the length of time she had to wear it. I wanted photo evidence that she had complied with my orders. Sure enough, she had! The ginger root was lodged into her ass and she was to masturbate and cum if she could. Little whore did cum in record time. She told me how much it burned and didn’t want that punishment again.

If she acts out of turn again her punishments will grow more daring and difficult. Threats of painting each fingernail a pretty pink every time she fucks up. From baby pink all the way to hot pink. Because she is a dedicated sissy boy to me I would even go as far as purchasing a cock cage if she cannot control her masturbating.

It’s simple really, do as you’re told if you are my submissive phone sex slut. She did do as promised and I am now doing as I promised. Using her pictures in this blog to humiliate her and show her I mean business.

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Sissy Boy

I do have her permission to use them*