I Was Caught Crossdressing

My roommate caught me wearing lingerie

Highonheels · 51-55, M

The roommate I live with now knew about my dressing up before I even moved in with him , when I moved in I brought all my male and female clothes with me at first I would only wear my female clothes under my male clothes , one day while he was at work I wore a dress , tights and heels around the house all day well he came home while I was in the bathroom and I didnt realize he was home when I came out of the bathroom he saw me and he could tell I was a bit embarrassed / shameful he said man don't even worry about it its all good , whatever makes you comfortable just make yourself at home, I said thank you so much , I was a bit worried about whether seeing me dressed up would make you uncomfortable he said no not really well maybe a little but I'll just have to get used to it I guess so go ahead and don't don't be ashamed of who you are.
So now he let's me wear anything I want except lingerie in around the house.

Highonheels · 51-55, M

@silkydrawers well the kind of lingerie I have is quite revealing and I would be quite embarrassed to be seen by him Wearing it

CDisOKbiMe · 70-79, M

@silkydrawers Morning Silky! I got a similar survey in an email from Hanes. It was a simple boxers or jockies question and I responded that they should at least have "other" as an option and a place for comments, that I hadn't worn male underwear in over forty years. I didn't get a response; not that I thought I would.
As a long time lingerie lover I'm sure you remember when Vanity Fair was top of the line and my personal favorite, but hard to find now and not the same. It grew into VF Brands that included Lee (Just Below the Waist shorts and jeans are my favorite) among others. When Warren Buffet bought Fruit-of-the-Loom he also bought Vanity Fair from VF Brands. Now Vanity Fair lingerie is being made by Fruit of the Loom and the original Vanity Fair company doesn't make lingerie. That just doesn't seem right to me. I guess it's only a matter of time until I buy a pair of panties and discover it's made by General Motors.