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…