My fantasy is to be a crossdressed secretary. I want to wear a tight skirt suit and feel it rub my pretty lingerie. I dream of being pawed by hands reaching under my skirt and taken into the office to deliver some personal service.
Officestyle Officestyle
36-40, T
4 Responses Sep 9, 2012


Seems like quite a few of us on here share this fantasy - not surprising really as it is just so hot.

For me I love to slip into my navy blues (Skirt, nylons and heels) and white blouse and play the subservient secretary. It's not just the look that does it but all the connotations that accompany both the look and the role. Soooooooo sexy.

I also like to add OTK which adds that extra bit of spice to this fantasy.

Take good care and be careful what you wish for.

It sounds hot. What did you wear?

This is also one of my top fantasies! I have actually gone into my office on the weekend and dressed, it was unbelievably hot!

When doing paper work in my home office more often than not I am dressed as my secretary, with my wife’s approval. We have had many memorable while she has “caught” me being my secretary. I have posted stories about this.

That must be delightful to slip into a skirt and play.