Crossdressing With Aunt Christy-A True Story

Story by the pretty and witty Tonya St.Clair.

That first night wearing a nightie might have been my initial step into crossdressing, but it was what happened next that firmly put me on the path for good.

I went to Aunt Christy’s room to discover that all of her regular nighties were gone (in the laundry I assumed). Rather than revert back to wearing her basic cotton t-shirts I fished around in her lingerie drawer until I found what I now know was a poet’s shirt. It was white and totally sheer except for satin trim at the edges and pockets. I put it on and came downstairs only to meet with a raised eyebrow and stern look from my Aunt.

There was a long, silent pause. I think she was trying to scare me out of my choice when she said, “If you’re going to wear that one, then you must wear the underwear that goes with it.” She disappeared upstairs with a purposeful gate and came back just a few moments later with a pair of white satin panties in her hand. “Here!” she said, thrusting her hand out. “Put these on.”

She turned her back and I slipped out of my boy briefs and in to her panties. When she turned around she asked sternly, “So do you like those?”

She looked me up and down and I stood there sheepishly, head down looking at my toes. But then her voice softened a little. “Hmmm, it looks like you do,” noticing my excitement with a warming smile. After that, nothing more was said about my wardrobe choice…


Crossdressing With Aunt Christy

Crossdressing With Aunt Christy

10 thoughts on “Crossdressing With Aunt Christy-A True Story

  1. Hi, Miss Teresa. I love the story. Specially because it also helps to learn, understand and imagine. As you said, is so much fun.

    I learned about wardrobe, words, ways and so much. Love about measures. I’ll try that. And of course, now I admire and respect women much more. Being a lady is not easy and much less looking always great.

    Was a great experience, once more, reading you. Thanks.
    Lovely, June, Miss Teresa.

  2. Pingback: They Made Him a Prissy Sissy Schoolie Slut | Strapped In Silk Forced Feminization Fantasies, Fetishes and Stories

  3. Can I just say what a comfort to discover someone who genuinely understands what they are discussing online. More people need to check this out and understand this side of the story. By the way I’m a big fat sissy.

  4. Howdy. This article could not be written any better. Going through this article reminds me of my previous roommate. He continually kept preaching about this. I am going to send this post to him. Fairly certain he will have a great read. I appreciate you for sharing!

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