I claimed my reward last night. My wife set an expectation for my behavior over the holidays, and I succeeded in earning an orgasm. Things are back to normal after the holidays (and the Rough Road a few days ago).

She arrived home from work to find me wearing a nice black and white winter-motif knit dress she bought me a couple of weeks ago. It fits me very well and I think I look really good in it. I had on knee-high black leather lace-up boots with 3.5 inch heels, matching earrings, a tight girdle, and my hair up in a high ponytail.

I had completed all the things she wanted me to do while she finished her late work day. As she walked into the house I started making her supper. I had already eaten so I served her as soon as it was ready, and then I cleaned up. She seemed pleased.

While getting ready for bed, she asked if I wanted to claim my reward tonight. “Yes!” was my enthusiastic answer. Later in bed she asked me how I wanted to do it. Oh, the thrill of having options! I chose to simply masturbate, and I asked her if she would “tell me a story”. She agreed, and thought for a few moments before she started her tale.

Her story focused on a wimpy husband with a puny, worthless cock. He was good for cleaning and other menial tasks, and deserved to be dressed like the slave and servant that he was. His wife was so sexually unsatisfied that she had to find other men to fuck, real men with big cocks that she could actually feel inside her. Muscular, black men with thick cocks that could really satisfy her need for great sex.

She went on about how the ridiculous, tiny, pinkish dick of this husband needed to be locked up in chastity because it wasn’t good for anything. His wonderful wife did allow him to masturbate on rare occasions. The last time she did, she decided it would be a month until his next orgasm.

This pussy husband, she continued, dreamed about other men’s cocks. She said he recently watched a movie and lusted over some of the black men in it, thinking about their big, dark penises. He fantasized about those manly dicks getting rammed up his sissy hole, fucking him long and hard, and how much he enjoyed that. Although he could not provide pleasure with his own dinky dick, he could provide pleasure to other men’s real cocks.

That’s when I came. She stopped her story, and I relished the orgasm. The imagery of her story lingered as I enjoyed the intensity, and then floated in post-orgasmic contentment. I noticed that I had no pain or soreness from masturbating, which suggests that my PA piercing may be fully healed now. Yay!

I cuddled up to her in bed and thanked her for the reward. She asked me if I liked her story, and I said that I really did. She pointed out that I didn’t seem to last very long, which sort of embarrassed me. She noted that her story had some similarities to our situation. I laughed. Then she said that there was one part that was true: the part about how long it will be until the next orgasm. I said “Yes, Mistress.”

This strikes me as a milestone. It’s the first time she’s decided on a period of time for me to be chaste. I wonder about things like time off for good behavior, or a longer sentence if I don’t meet her expectations. I guess I have several weeks to find out those details.

A bit later she asked me why I like to crossdress. We’ve discussed it before, but she seemed to want more details. I told her how I like the sensuality of the different clothing. Long ago it used to be taboo and erotic, whereas now it feels like it completes me in some way. I love feeling and looking feminine.

She complimented me again at how good I look lately. She said my choices about outfit combinations, accessories, and makeup is much improved. I thanked her for her help with that, particularly buying nice things for me. And I acknowledge that hairstyles are still my weakest point.

She said she wanted to go through my closet (of women’s clothing) and get rid of some things. She said she prefers me looking less slutty, unless of course it is her wish to dress me like a whore. “Yes, Ma’am”. I wish! She talked about buying more nice things for me at her favorite women’s clothing store. They know here there, and she said the staff probably knows that she’s buying things for me. That made me blush.

A while back she gave me some lavender women’s pajamas which I really enjoy wearing at night. Men’s PJs are so plain and basic. These have nice pretty seams and even a ribbon for the waist tie. She also bought me these fuzzy white and pink slippers with pom-poms. Sometimes I’ll just spend the evening in my girlie jammies; it feels so right.

Although I like feeling and looking female, I also like it when she calls me her sissy husband, or worse. Sometimes I wonder why her humiliation is erotic for me, but mostly I just enjoy it, particularly since I know she enjoys embarrassing me.

Tonight she teased me about dropping something off next door to where she works. This is where the black man works who she says is the “father” of our biracial children (our twin life-like dolls). I believe she really did talk with him in person today. And she teased me about how he looked at her (wanting her).

I’m glad we’re together.

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