I Wore a Skirt to Work

OK, it was Halloween.  But I did it!  But first, let me mention the previous Halloweens.  If you have been following my posts, then you know that I wore a dress one year for Halloween.  The following year, I was working at a new job and I dressed up like a male cartoon character.  Then the subsequent year, I wore a skirt to work.  In between all of these events, I cannot remember having very many significant dressing events.  I know I would underdress (feminine undergarments) occasionally, but that’s all I remember.  It might be because my wife and I were trying to have babies at this point and wearing restrictive underclothes was counterproductive.

Somewhere in this period of time, I must have purged.  (Purging is when a crossdresser decides to quit dressing and gets rid of all of their clothes.)  I no longer had those heels that I had from the previous Halloween.

My plan was to wear a black skirt, dark pantyhose, and heels with a men’s shirt and tie.

I started shopping.  I visited that store where I found my dress from the other Halloween.  I do not remember where I found the skirt I wore to work, but I am sure I wore pantyhose under my pants and tried on outfits with help.  But I honestly cannot remember.  It might be that I had bought the skirt weeks or months earlier and I just wore some old thing from my closet to work.

My wife and I went shoe shopping.  She was with me at the store where I found my shoes.  There were other people in the store.  But since it was for Halloween, it wasn’t too scary.  I “had an excuse”.  The sales person was friendly and helpful.  I had shopped quite a bit for shoes.  The Payless stores that I visited did not have any basic black heels.  That is where I have done my shoe shopping previously.  That’s why I ended up in this full-price shoe store.  I ended up paying over $30 for the shoes (which is not too bad for women’s shoes).  They were not pretty to me.  But they would have to be sufficient.  Halloween had almost arrived.

Halloween morning, I got up and shaved my legs.  I put on my skirt, and off black Leggs Sheer Energy Active Support pantyhose.  (I did not like their color.  I wanted jet black.)  I put on my 2 inch sling back heels.  My shirt was a men’s white collared long sleeved dress shirt.  My tie was one my wife made for me with a Halloween theme.  My head was my normal man head.  Before I left for work, my not-so-supportive wife got out of bed and said, well, let me see you.  She laughed politely and sent me to work in a skirt.

I got to work early.  I was avoiding people.  People at work knew I was going to dress up because I told them to also dress up.  I did not want to be the only one in costume!  I did not tell them what I was going to wear.  The office secretary came to my cubicle to see what I had on.  I told her I decided not to dress up and spun my chair around.  We had a fun laugh.  Word spread quickly.  It seemed like 30 people visited my cubicle for the next hour.

Another lady in the office dressed like a witch.  She and I and a couple others went up to the accounting office.  Going up the stairs, I commented that my slip was sliding against my hose and shooting lightening up my back side!  The secretary laughed quite a lot about this.  The accounting girls were great.  One was dressed like the “Scream” character.  She ran up to me while masked and rubbed my leg.  My skirt was just below the knee.  I pulled it up for them to show more leg.  They roared with laughter.  This was GREAT!  I confessed that I liked how pantyhose felt.  I was with a bunch of women who knew me and respected me and I was talking about the pantyhose I was wearing.  Why can’t life be like this all the time?  😦

All of us who dressed up ended up going around the office door to door handing out cake.  I had to ask the others (all women) to slow down.  I could not walk in the heels.  One older woman in her 50’s exclaimed, “You wore pantyhose!”  Then she declared, “You shaved your legs!”  It was kind of awkward for some reason.  I felt like I wanted her to back off.  She was drawing too much attention to me or something.  There were other people whom I did not work with in the room.

Everyone who came to work that day saw me in a skirt and heels.  This was the best workday of my life.  I was crossdressing, I was in public, I was with people who know me, and I was not creeping around doing something weird.  I was sitting in my desk trying to pay attention to my work (it was difficult) and being normal.

I did not think to bring a camera.  Someone did some archaeological digging and found a prehistoric camera and took the following picture: a picture.  (It appears that I need to do some archaeological digging of my own to find it.  I am sorry…)  If I find it, I will add it later.

Lunchtime came.  I brought a lunch as a backup, but I intended to go out to eat with my co-workers.   I was SO stressed out.  We got to the restaurant and walked in.  I could not tell if anyone even noticed me.  I seem to remember a couple waitresses laughing together.  Then it was a non-event, except that my muscles were getting tired of holding my knees together.  We sat and ate and talked like normal.  My boss told us some stories from when he dressed like a girl for Halloween.

When we got up to leave, we all lined up at the cash register.  I was much more relaxed, now.  But there were two men eating at a table beside where we needed to line up.  I was uneasy about it.  Then one guy said, “If I was as big as you, I would dress like that too!”  He probably stood a foot shorter than me.  I did not expect to have a man complement my manly size while I stood in front of him in heels.  It made quite a difference for him to say something nice to me when I was so exposed.  (I wonder why he said that…)

I worked the rest of the day and loved it.  I sat for a while in the witch’s cubicle talking.  I sat in the rocking chair she had.  I worked on crossing my legs.  She gave me advice.

For weeks after that, and perhaps for the entire time I worked there, I could talk to the women about clothing and fashion in a new way.  The topic of pantyhose was not off limits.  It was like I was on the inside.  I could ask, “What color are your pantyhose?  They are pretty.”  We could talk shoes, leg shaving or whatever.  Of course, these conversations did not happen often, but they did happen!

Let me interrupt the story at this point to say that the best part of crossdressing at work like this was that it was completely non-sexual.  I was just a guy who loves to wear these soft fabrics wearing the fabrics and doing what I normally do.  That is what makes this one of the very best crossdressing experiences ever!

Years later, I stopped in at that job to say hello to all of my old friends.  In the accounting office, the first question posed to me (in jest) was, “Have you been wearing pantyhose?” or something like that and they all laughed.  There was a new guy working in the office.  I remember the look on his face after that lady said that.  I never had a chance to explain that it was due to a Halloween costume.

I loved that job.  Sometimes I miss it.  They were great people.  We had fun.  I have not had a job since then where the people were such a family and where we could joke and tease in such a friendly way.  Also, I have not had a job since then where I felt comfortable wearing a skirt to work.