Aunt Turns My Crossdressing Husband Into A Precious Little Sissy

Dear Enslaved,

Bob and I got married right out of college, and I thought we had a perfect marriage. That is, until a few months after we walked down the aisle, I discovered the macho man I’d thought I’d married loved dressing up in women’s clothes. Naively, he managed to convince me it was just a harmless pastime, which I tolerated, letting him come to bed in one of my nighties and panties.
However, it only got worse from there…nylons, garter belt, and high heels followed. Then skirts and dresses, and I caught him trying on my makeup. The final straw was when he wanted me to call him Barbara.
In tears I went to my closest confident, my Aunt Julia, who is in her late 60’s and wealthy beyond belief.
“I told you there was something odd about him when you married, dear. So what do you want to do?”
“I’ll give him one last chance. No dressing up or acting girly. Then I don’t know what I’ll do,” I admitted.
“Well, if you can’t cure him, I think I know what will,” she declared with a twinkle in her eye.
Putting my foot down lasted all of a couple of weeks. I caught him trying on one of my best dresses, and ripping it up the back. I immediately called my Aunt to have tea and discuss my situation.
“I don’t know what you’ve got up your sleeve, Aunt Julia, but he’s all yours,” I said in disgust.
“Just bring him to dinner and I’ll take it from there.”
Part way through dinner he fell asleep. Without warning or dozing or anything, he just passed out in his plate of casserole.
“You can leave now, Victoria dear. I’ll give you a call when I think ‘she’s’ ready to be presented in public,” she smiled.
I didn’t miss her referring to him as “her,” and I couldn’t wait for her to tell me what she had planned. Two months went by without a word, and then a few weeks into the third month Aunt Julia called and “she” was ready to be presented.
“Oh my god.” was all I could say as one of the maids brought her in.
“May I present your niece, Miss Betsy Sue. Come over and say ‘hello’ to your Auntie Victoria, properly, as you were taught. Rebecca, you know what to do if her manners aren’t perfect,” Aunt Julia said sternly to the maid who was holding a fierce looking hairbrush.
I’ll admit I was still speechless, for what Aunt Julia had done, you see, was to turn my skirt loving husband into the most frilly girl I ever saw. He–or she–had on the most dainty, white sissy dress. If he wanted to wear skirts then he was certainly getting his fill now! It was literally dripping with ruffles and lace everywhere. The short skirt showed off his girlish legs and the petticoat he was wearing, while the lace edged, white anklets and shiny, black strapped baby doll shoes added the perfect juvenile touches. As did his now blonde, long hair done up in pigtails of all things. Plus, his face now looked more like a doll’s with absurdly long lashes and pink cupid’s lips.
When he saw me he started to run over to me, crying, and in the most startling, squeaky, girlish voice pleaded, “Victoria, please don’t let her…” Which was as far as he got when the maid bent her over a chair and spanked the living daylights out of her.

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This entry was posted in Letters.