The Women Who Love To Femininize Their Men — Ashley.

Fiona Dobson
3 min readApr 21, 2022

My current boyfriend happens to fit in many of my clothes. It’s been a thing with me since leaving home and going to university in Montreal, but I have this thing about having all my boyfriends dress for me.

It started out innocently enough. I remember clearly how one of my dates showed up while I was getting ready to go out one night. He was impatient and wanted to get moving, while I was still getting dressed. Even as I put on my make up he was whining about how long I was taking.

I said to him “You should try walking a mile in my shoes.”

I’d meant it as a rhetorical question, but it went over his head. This one wasn’t exactly the sharpest knife in the draw. It did give me an idea though.

Later that night, after we’d got back to my place I told him to try putting on a skirt and doing some make up — just to see how long he took to do it. He was a little reluctant, but eventually he did try on a skirt and smeared make up horribly on his face. He didn’t last long with me after that, but I did notice being made to do some make up and wear some of my clothes did make him a little more obedient.

As a psychology major you’d think I’d be able to explain this, but it didn’t make much sense to me, as undeniable as it was. ‘Obedience’ is an enjoyable thing to…

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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