It’s a busy life being a crossdressing advertising executive.

Fiona Dobson
3 min readMar 13, 2023

Just yesterday I had to run into the office, which I generally avoid these days, but there were two or three meetings I had to attend. The agency handles a number of pro bono accounts for charities, and I often oversee these.

Called into the boardroom I listened to the new ideas for the Eczema fundraising campaign. Call it my sensitive nature, if you like, but when I get a good idea in my head it really is like an itch I have to scratch, which is why I keep such a tight handle on the accounts I run. I like to keep a close eye on the way the our clients are represented. I really don’t know why Desmond, one of the young account executives, would think that a scratch and win card would be an appropriate fund raising campaign for that particular account.

I was cornered at the watercooler between meetings at one point, by one of the boys in Creative.”

Fiona,” said Jeff, “you remember the lady that did that presentation on ‘Sexual Harassment in the Workplace’?”

“Which one,” I replied. “There were two of them. The tall one or the short one?”

“The one with the great rack,” said Jeff.

“Oh, that would be Joan,” I replied as I slipped away thinking that the workshop was lost on some of the boys in Creative. There was a smell…

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Fiona Dobson

The trans blog you’ll love even if you’ve never tried on your sister’s panties. http://FionaDobson.com