Son Crossdressing as a Queen

“Daddy, I’m going to be in a school play.”

“That’s good, son.”

“Erm, not really….they want me to play the wicked queen. I need to dress as a woman!”

I begin to smile.

“Dad, it’ll look stupid!”

Wider smile.

“I’m going to need to wear a wig, woman’s shoes, and a dress.”

I’m really smiling now, but trying to suppress it.

SO chimes in…”well you could borrow some of my stuff.”

It’s like that feeling of “if only you knew”…..which of course the kids don’t!

“Nothing wrong with that” I add.

Further protests from my young actor son.

“But it’ll look weird!”

“Son, I’m sure you’ll make a beautiful queen.” I’m now clenching my teeth in order to stifle the laugh. I look pretty good myself when crossdressed……..but only the wife and I know this.

“We will help you look amazing.”

Then another thought hits me……hey, not my stuff!

I mean, it would be great to help him out with the costuming….but then I’m open to being busted by the kids. But, I don’t want him to feel intimidated by theatrical crossdressing, so I need to be positive and support him, but not overdo it in front of all the kids!

The experience, thought quite amusing, has shown me how comfortable I have become about crossdressing. Accepting who I am, on this occasion, brought laughter and joy.

I hope it made you smile too.


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When I'm not busy teaching, kick boxing, or looking after a household full of offspring, I enjoy exploring my feminine side with a new degree of freedom since coming out. I crossdress whenever possible with no desire to transition.

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Cookie JessicaLynn (Irish)

Such a touching story. Hope his night went well…..

skippy1965 Cynthia
Trusted Member
7 years ago

I love the story REnelle!! It is such a shame that we can’t all share our entire selves with the ones we love for fear of the world’s reactions! When we CAN do hat, we will know that we have been accepted completely. thanks so much for sharing this story!

7 years ago

Great story. I find it interesting that the school cast a boy as the Wicked Queen. Was that just to give everyone a go or was it perhaps because they figured a boy would naturally make a ‘woman’ look ugly and evil?

Either way, I’m sure you both made sure he truly was a beautiful, if wicked, queen.


Monika Sweet
7 years ago

When my sin tries his mom’s top or jacket or shoes, my usual reaction is.. Stop it. Then I look inside and tell him… Is this what you like to wear… And he says “No… Not really but just like that.." I get confused and the subject is closed.

My wife knows and she does not want me to encourage the boy to dress up… The girl however is quite cool with him although she comes and tells me everytime he puts on his mom’s stuff… Hoping I would be angry on him…!!! Poor girl.

jessica humphrey
jessica humphrey
7 years ago

Hi I am Jessica and I have been out since a very young age and I have to say I am so happy and dress as a woman 24/7 and I have felt that way since I can remember.

7 years ago

Nice that you are both supportive of his theatrical Cross Dressing, though we all know it may be the first step of a life long love of doing it.
My first time was with help of the most popular girls of my Senior class as they made me over as a Powder Puff Cheerleader

Rosaliy Lynne
Rosaliy Lynne
7 years ago

great to see supportive parent even if you were still hiding your femme side at the time. Congrats and good luck.

7 years ago

Its better if you and your wife help him get dressed for the play than having him watch Monty Python videos to learn how it’s done.

Active Member
6 years ago

My adult daughters have borrow from me some times. One even stolen a pair of my knee high boots. Saying she looked better in them. As for me I didn’t care. I didn’t really like them anyways.

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