Sweetheart, we threw all your boy clothes out months ago.
You look fine.
A nice pair of sheer black pantyhose, a very pretty pink skirt and a black lace top.
A little bit sexy, but elegant.
I know it’s your high school football team reunion, and as former team captain, you feel apprehensive about turning up in girl clothes.
But we went through this at the time.
It’s going to be hard living full time as a sissy.
You will get stared at.
There will be whispers and smirks and sniggers.
You discovered that already.
It’s extra hard when it involves family and friends - especially in a masculine environment like a football team, where you invested a great deal of time in establishing a strong alpha male perception of yourself.
But I thought we’d discussed all that and you’ve accepted that it’s a charade, and that, whilst you born with a male anatomy you are too girlie to be a boy or a man.
Precious, you’ve been dressing up in girlie clothes since you were a boy.
That urge hasn’t gone away. It’s got more powerful.
But you don’t want to go back to pretending to be a boy and living in fear of exposure; that people will find out you’re really a sissy.
Being a sissy isn’t easy. The shame will always be there.
But if you embrace it, it’s easier than living in constant fear of being found out.
Look, you family have accepted it, albeit reluctantly. They don’t like it - it’s hard for them to comprehend- but they’re getting used to it you living in girl clothes and living with an older man.
Some of your friends have accepted you - uneasily at first, but they’re coming round.
Those who have shunned you aren’t worth it anyhow.
But isn’t it such a relief not to live in fear of them finding out and worrying about how they might react.
There are still some of your friends who don’t know, but they’ll find out eventually.
It’s best to get it out there early, on your terms.
The guys from the football team, and their cheer leader girlfriends will be hard.
They’ll have some fun with you at first, but they’ll get used to it. I’ll bet at least one of them tries to run his hand up your stockinged thighs under the table before the night is out.
Standing before their girlfriends - some of them pretty young things you used to go out with, pretending to be a boy, when you’d rather just have been wearing their clothes - dressed similarly to them in pantyhose and a sexy skirt and high heels.
It will be awkward for them too. A guy - or what they though was a masculine guy, who they’d actually had inside them suddenly minces in, as a sissy dressed in girl clothes.
They need to reconcile it in their own minds as well, but once they do, you’ll feel a lot more comfortable as one of them than one of the boys.
And if you need to have a good cry when you get home, that’s ok too. It’s natural.
Now run along and get it over with.
You may even enjoy yourself.