Set me free.

Fiona Dobson
7 min readJul 21, 2021

Set me free.

In the morning I groaned into wakefulness. My body ached from the previous nights exertions. As I came closer to wakefulness I found new pains. It had been a night to remember. If only I could marshal my thoughts.

And as I did remember I began to feel uneasy.

Sounds came from an ensuite bathroom, and I head heels on hard granite flooring. Then she came out of the bathroom already dressed and adjusting an earing, hurrying across the room to pick up her handbag. I struggled to remember her name.

“Good morning… you,” I said with a smile to cover up my oversight.

“Gotta run,” she said. “I’ve got a 9 o’clock.”

I groaned. What kind of pervert organises meetings for 9 am?

Memories of last night began to clarify. That’s when I noticed what I was wearing.

“Ouch,” I said as I moved. For the first time I was aware of the sharp pain in my back.

“I’ll call you,” she said as she headed for the door.

And then she was gone, patent leather shoes clacking away with her perfect ankles.

I am not what you call a morning person. I slipped back into sleep and it wasn’t until an hour later that I woke once more. This time things came together more swiftly.

What the hell was I wearing? This nylon thing felt unfamiliar, and then I noticed the other clothes scattered on the floor. Stockings, panties. And who the hell was that earlier leaving this hotel room?

I sat up in the bed. I was wearing a pink fluffy neglige. That was odd. And then the memories of last night flooded in.

‘Oh, my god,’ I thought.

I joined the dots and remembered the bar in the hotel. I’d fallen into conversation with… I still couldn’t remember her name… with her. Black hair. Well groomed and sophisticated in her appearance. Professional. Absolutely precise. She’d told the barman how she liked her martini and she’d been the picture of reserve.

We fell into easy conversation and she said she was visiting her company’s local office. I explained I lived across town, but my car had developed trouble and I’d dropped it in for a service, which was supposed to be ready at…

Fiona Dobson

The crossdressing blog you’ll love even if you’ve never tried on your sister’s panties.