Reflecting On Being Discovered Wearing Panties By My Supervisor ...

Several years ago (long before I got to dress en femme for my current employer) I was working for a design/build construction company the primarily worked on high end boutique like mini malls. Actuall back in 2002 through 2007.

Our work had us travelling fairly frequently, but I spent many hours late in the office as well, reviewing plans and pricing projects.

As a crossdresser with the opportunity to travel on the company's dime, I was always packing two wardrobes ... one for work and one for after hours. But I always wore my fancies (bra, panties, occaisional OBG, and hose of course) under my regular work clothes no matter where at work.

One month when I was back at the comapny headquarters I found myself working with a small contingent as most of our folks were travelling to out of state work sites.

In fact there were only three of us in the office during the day, and I found myself working into the late evening for much oof that month.

So as soon as the others were out of the office and I was pretty sure they had no reason to return until the following morning, I would slip my shoes, jeans, and shirt or sweater off and slip into a more feminine top, skirt and some heels or flats.

This was wonderful for the first three weeks or so. And my supervisor complimented me on the success of my work. (Little did he know that the reasons were I was a happy worker attired as I preferred.)

Then on a Monday morning as I was bending down to open the breakroom coffee cabinet door to get some dark roast to brew, I heard him behind me say "mmm what have we here?"

I was startled and jumped up. I asked him what he was inquiring about.

He said nothing, other than I made a great pot of coffee and kind of smiled mischeviously while adding "I can see you have a taste for other things more traditionally feminine in nature."

I protested mildly until I noticed that my sweater had risen on my back and my panties were showing over the top of my slacks. He smiled as I was reaching to feel my back ...

Well I could feel my face getting warm and my stutterd response of "Oh can we keep this between us?"

He smiled and suggested we chat about it over drinks later that night.

Needless to say, I was a nervous wreck. I was not upset so much that someone had discovered my secret of wearing my fancies to work under my regular clothes, but my supervisor was a bit of a right wing type. And at the time I was not really interested in getting either fired for no good reason, or becoming the butt of jokes around the office.

I met him a local restaurant/hotel and we sat at a booth kind of out of the way of the crowd. He seemed a little uncomfortable but his demeanor was still a bit bossy-like.

He ordered drinks for both of us ... for himself a strong brew and for me a glass of chamapgne, stating as the waitress walked away that he figured from seeing my "panty tops this morning, I assume your taste buds are a bit more delicate."

I turned completely red as he pointed out to me. But then the surprise.

"Listen Henry," he started with, "I am not going to embarrass you. I do like having a happy team of people working for me. And you got to understand that a guy like me can't help but tease a bit ... just between you and me."

I must have looked all at once relieved and shocked and desperate to find out what his agenda was, because as soon as we were served our drinks he ordered dinner for us both.

I just sat there and squirmed a bit and tried to relax. Then he surprised me.

"I find it intriguing that you wear those panties. Anything else pretty you are wearing tonight?"

I stammered, "Do I really have to answer that?"

"No, but I would appreciate your honesty. I know you might think I am being a bit of a teasing bully here, but I really am keeping this between us. And I am curious ... but be assured that it's not because I am expecting you to do anything for me or with me ... I am not gay or bi or anything like that!" he stated rather quietly but firmly.

I was relieved but also still plenty nervous.

He went on about how he wanted his team to be happy as they are friends and aslo they produce more for the company if they work in a friendly environment.

As we had another drink I finally decided to open up a little bit.

I explained that I had been wearing panties, bras and hosiery to work for almost as long as I had worked for him, and thought I had kept it a good secret. He said he would have never noticed had I not been bent over to reach inot the cabint that morning ... and then he also told me he figured out I was wearing a bra as well as he looked at my shoulders and could see the straps ... damn I thought I was being cool about things, and I wondered if anyone else had noticed that afternoon.

He suggested that I need not change my habits and that he would not mention it to anyone as long as I wanted it that way. He also said I was probably his most productive colleague, especially over the past few weeks and wanted me to be happy at work.

I then got brave enough (after the thrid glass of champagne) to explain to him about my working late the last few weeks and how I got more done during my 'later hours' and finally explained, a bit hesitantly, that 'Henry' was increasingly more productive when attired as 'Henrietta' during those late evenings. I held my breath.

Then after he expressed surprise at my explanation of dressing en femme at the office when all alone, he suggested that while he did not personally approve, he thought Henrietta probably ought to become a 'partime' employee of sorts to help out Henry when he was alone in the office.

With that I got to occasionally dress en femme without being afraid of being fired.

I ended up working there until the market turned south, but was the last member of the team to be laid off.

dustywhitney dustywhitney
51-55, T
13 Responses Dec 13, 2012

How fantastic to have the support of your manager. That is the dream that most all of us share.

all the times wearing my fem items on under my work clothes never got caught your story was great and please add me

Thanks Girlfriend. Will add asap. Always a bit challenged with the menu here, so don't give up on me, please.

BTW what lil ole frillies do you like to wear under your street clothes?

Hey there Stephine. Thanks. BTW ou have a great name. I finally settled on Dusty, after several 'aliases.'

I had a great time working for that company. It turned out near the end I had the office most to myself as and could dress en femme
most of the week.

My boss got used to me being dressed as Henrietta when he came in from field work. I still am in touch with him occasionally and he teases that he misses the efficiency of Henrietta with his new team.

I think he had a secret curiosity as I caught him stealing glances of my legs on several occasions ... But never wanted to embarrass him as he had been so sweet to let Henrietta have a job.

please add me


go to my profile and request to be friends

Very nice story!

Very cool..need more people in the world like that.

Wonderful story and I am so happy for you

i like your story you had a very nice boss

I love your story! What a fantastic person your boss was! To accept you, and not abuse you! Wonderful!

Wow! Just goes to show that you and Henrietta worked very well together and were valued employes, or should I say was a valued employee.

Wonderful article, thank you for sharing. Feel free to add me as a friend here on E P.

Hello Sherry. Thanks sweetie. I will definitely add you as a friend as soon as I fihgure how to do that.

You're welcome Sis.

Cool boss and it must have been a great place to work too. Thanks for sharing that story and hopefully your new employer is as great.

Thanks. Yeah, my new bss s actully a lot of fun ... but strictly flirtatious.

Sounds like a new story in the making, Dusty. Do tell ... ;-)

Lovely story and a great boss

Thanks for your note. By the way, I love the dress in your photo.

Thank you,it was taken quite awhile ago,but it got left behind when I split from my wife

Lovely story, I too work in construction and often wear female attire under my work clothes. I've never been caught though........yet!
Fancy being friends?

Hello there. Sorry it took a fews days to respond to oyur question ... but have been away for the weekend. Just getting ready for work right now but would enjoy hearing from you. I always wondered if other of my construction colleagues had similar undies as pretty as mine ... now at leat I know someone else does. My email is:

Feel free to send along something we can chat about!


I've been working in construction and manual labor since 13 and have been wearing at least panties under my clothes at work on and off for th majority of that time lately (past 3 years) i almost never wore anything other than panties and sometimes more under my work clothes