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Summer of 84-The Slippery Slope
Written by Tonya St.Clair

In the summer of 1984 my parents left to go on a book tour. As anthropologists, they had published a book that they wanted college professors to start using as their official class text. Rather than drag me and my brother cross country, they farmed us out to the family. While my brother got to stay with our grandparents and therefore got full time access to their pool all summer, I was much luckier getting to stay with my Aunt.

Aunt Christy

Aunt Christy worked at a bank and was gone from 8am to 5pm. But to make up for leaving me alone during the day, she tried to do fun stuff in the evenings like playing games and renting movies for us to watch. One night after dinner early on in my visit, she announced that she had picked up a movie at the video store for us.

“I’ll make some popcorn while you put on your pajamas and we can make it a movie night.”

“Ah, Aunt Christy, I’m a little too old to wear pajamas to bed. I just usually sleep in my underwear,” I said somewhat embarrassed.

“Well,” she replied, “we can’t have you walking around here in just your tighty-whiteys.”

Then she sent my up to her room to get one of her t-shirts from her dresser. I protested a little, but she assured me that it was no big deal and that no one was going to know. I still wasn’t convinced. So she told me how in the old days, everyone wore a nightshirt to bed, and that pajamas were a recent fashion invention.

Finally she made a deal, that if I went and changed for bed like she asked, that she would change and wear one too while we watched our movie. That way I wouldn’t feel underdressed. In the end, I did as she said and found a zebra stripped t-shirt (it was the 80’s!) to wear.

It felt breezy since I’d never worn anything dress-like before, but it also felt odd-like I was naked under my clothes. I know that sounds funny, but if you’ve ever cross dressed you’ll know what I mean.

When I came back down she smiled and told me that we’d go find me some manjamas (said in her deepest manly voice) at the store later in the week. For now I could just keep wearing her t-shirts to bed. But things got busy for my aunt, and I hung out with my friends a lot, so we never made it out to the store to do our clothes shopping.

One evening I went to Aunt Christy’s dresser and there were no more clean t-shirts for me to wear. When I came back down still fully dressed, she was sitting at the table with a Monopoly game all set up. She asked why I wasn’t changed and I told her.

“Oh, well just grab something from the next drawer up.”

I went back to her room and discovered that the next drawer up was one of her lingerie drawers. Was she kidding?

“Here, use this one.”

I didn’t know that she had followed me up to her room, and I jumped when she spoke as she reached past me and in to the pile of satin and lace. She handed me something purple and held it up for me with a smile.

It was a nightgown. “Just think of it as another oversized t-shirt but made from different material.”

In her defense, it was not terribly different than just another t-shirt. Only the lace at the collar and on the sleeves, and the cool silky material gave it away as anything different.

“Here, I’ll wear one too.” She grabbed a similar nightie in bright blue. Then she turned her back to me and pulled off her shirt and bra. She slipped the nightie over her head and turned around.

“Go ahead,” she urged as she reached up under her nightie and slipped out of her jeans. I copied her actions and changed in the same manner.

We played our board game and I spent the whole night in her nightgown. I was distracted by just how different but amazing it felt on my skin. I was also distracted by seeing my aunt dressed in her nightie. I was in the full swing of discovering the female form, and seeing her body move, her unbound breasts swing under that nylon did nothing to help me win the game.

The next night, I didn’t need any encouragement to go back to her dresser and pick out another nightie to wear. In fact I kept wearing them even after she had done laundry and there were the more mundane t-shirts available in her dresser.

That first night wearing a nightie might have been my initial step in to 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 erect excitement with a warming smile. After that, nothing more was said about my wardrobe choice or my hard-on for the rest evening.

In the morning after everyone (and everything) had calmed down she sat with me and we had the Birds and Bees Talk. Then she pointed to a laundry basket she had set in the corner of my room.

“In there are some other clothes that you can use to experiment with. There’s a blouse, a skirt, a dress and some shoes you can try one as well as a bunch of different lingerie. Let me know if you have any questions on how to put any of it on.” Then she patted me on the knee and left me alone for the whole day.

The summer progressed from there, and that was only the beginning of my crossdressing with Aunt Christy. It was the summer that Todd discovered his inner Tonya.