Donated a black dress, ran home in nothing but heels

Throwaway for obvious reasons. Just got back from doing a bucket list dare I’ve sat on for a while and my legs are still trembling.

I literally just got upstairs and started writing, still a bit scattered and still naked. I should go back a bit.

Context, I’ve always enjoyed a bit of streaking. Nothing extreme or provocative, just the urge to occasionally test the limits. I’ve done a few WNBRs, been to clothing optional bars and done a couple of drunken nude runs through fields late at night. In all those I was at least surrounded by other people, usually also naked. At least at those I was always covered in a way, usually by other naked people.

This one was different, solo, and also included another element I’m into. I have a crossdressing side. Mostly confined to home, no wigs or makeup, just the clothes and the shoes. Feminised while still looking male. Crossdressing and streaking don’t usually mix naturally, but I’d had an idea in my head for a while and tonight was finally the night.

I’d bought this cheap little black dress ages ago. It felt cheap and uncomfortable, I never wore it. It wouldn’t last long, but someone could definitely get a few wears out of it. So instead of throwing it out, I decided to donate it.

The idea was simple. One block up across the street is a clothing donation bin. I’d walk over to it in the dress, take the dress off, put it in the bin and walk home.. naked. Simple right?

Alone, very late at night and no turning back after the critical point. I honestly wasn’t sure I’d manage the second part. I waited for a warm night.

The dress was black, short sleeves, white collar and well above my knee. Before the dress I put on socks and a pair of Dr Martens Marlena heels I was very pleased to find in my size a while back. I’ve never worn heels outside the house, still takes a bit of getting used to.

I stood there naked in front of the mirror for a moment, in high heels, and contemplated what I was about to do. I tied my keys around my neck with butcher twine (no pockets) and slipped the dress on.

I tried twice, both times closing my front door then immediately running back at the sound of engines in the distance. I realised the keys around my neck were slowing my re-entry, so I tied them around my wrist, clutching them in my hand, and went out again. This time I made it across the street.

Once across the street I just had to walk a block, between parked cars and trees. I was passed by a car and a cyclist, but in the shadows, they couldn’t have seen what I was wearing.

Finally I made it to the donation bin. Unspotted and no one around. I slipped the dress off with some tugging. Finally I put it in the chute and closed it. I wasn’t sure I’d actually get this far, but now I had no choice. I was a block from home, in heels, naked.

I saw a car turning a block ahead and ducked in the shadows. Then I started my walk back. At first I cupped myself for modesty instinctually. But after a few steps I was felling cocky. This whole thing has gone off perfectly, so I moved my hands to my side.

I counted the parked cars. I just needed to make it to the black one at the end, cross the street and I’d be home. Then halfway down I saw someone in the distance. It was too dark for them to see what I was wearing, or wasn’t wearing, and they were staring at their phone. Still, if I carried on in the same direction we would cross paths, so I bolted.

I slipped between two parked cars, then sprinted diagonally across the street. I don’t know if they saw, but the definitely heard my heels running on the asphalt, ungracefully.

After that I was at my front door. I hid behind a bin for a few moments, making sure I hadn’t been seen.

I just got upstairs and started writing. I’m still naked and haven’t taken the heels off.