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My First Halloween As A Girl – Part 2 – Dressing With My Wife

April 16, 2012

Go read part 1

UPDATE: Hello, you are visiting one of my most-visited blog posts.  Apparently, a lot of people search for “halloween crossdressing” and “crossdressing with wife”.  Thank you for the visit.  Hi, I am Joey.  I am just some guy who likes to wear women’s clothes as part of my man life.  The event covered in this blog post happened a long time ago when I was very nervous about going out.  I still crossdress secretly, but now, I go grocery shopping, get haircuts, eat at a restaurantgo to the eye doctor, fly on planes, and completed a course at a local community college; all in a skirt or dress as a man.


So, I had my costume put together.  My wife was willing to go out with me crossdressed.   However, I had nowhere to go.  But we were definitely going somewhere!  One big problem was that my wife did not have a costume.

I talked her into wearing my suit and dressing like a man.  I started the long process of getting myself ready.  Shower, and shave my legs.  Do my makeup.  My wife was a little uncomfortable with all of this, and did not want to do my makeup.  I did my own (for the first time).  It turned out OK.  I am very tall, I am not passable.   I made false breasts out of rice in the legs from some hose and stuffed my bra.  (I owned a bra!  It was my first.)  I put on my sheer skin-toned pantyhose.  I put on my dress and jacket and wig and black 2 inch heels.

I got my wife into my suit and shoes.  I think we had to stuff the toes to make them not flop around.  I put her hair into a ponytail.  I had to roll the legs of my suit inward.  I tied a tie on her.

Now what?  We went next door to our neighbors and presented ourselves.  They were amused, and suspicious.  The wife asked me, “Who did your makeup?”  Busted!  I confessed it was me.  She marveled at how well I did.  I probably looked too good to be a disinterested guy.  I had on new, pretty pantyhose with heels that fit and shaved legs.  I had a wig and a dress that fit me.  My wife had a baggy suit on.  I think any smart person could figure out that this was not a fluke for me.  Anyhow, we talked and laughed for a few minutes.

Then, we went to a movie rental store.  Since it was Halloween, I had an excuse, right?  Some people saw me in the store and moved to get a second look.  Maybe they were seeing my wife’s amusing costume, but I doubt it.  We laughed it off and looked around.  It was hard to stoop/squat to look at movies from the bottom shelf.  The dress was probably not long enough for someone my height.  Normally it was OK, when I was standing.  It came to just above my knee.  (Nowadays, I only wear things that go below my knees.)

I noticed several guys taking a glance down toward my legs.  It was so obvious!  The movie place had lots of lighting, so perhaps my hose were shiny.  I don’t know.  I cannot say whether I have seen the same glances since then.  But that night, I was very aware of these glances that guys were giving my legs (or maybe my shoes).  They would quickly look up so that I would not see them looking.  I did not see women giving my legs these looks.  I wonder if these were guys who love pantyhose.  Perhaps they just like to see women wearing them and do not wear them themselves.  Regardless, of whether they like them or not, I wonder if women notice me glancing down at their legs.  After all these years, have I just learned something very important?!?

One interesting thing that happened was that one of the girls working in the movie rental store was from that gay/straight club of which I attended a meeting.  She and I were very formal and conducted our business like strangers.  But it was less social than when you talk to a cashier who is a stranger.  I think we were both concerned that the other person might reveal some secret about ourselves.  (My wife did not know about the time I attended the meeting.)

After renting a movie, my wife and I drove around a little and then went home.  A dull ending to an evening that could have had so much potential.  I was so nervous to talk out and make plans with my wife that I never did it.  If she had a lot of time to change her mind, I guess I feared that she would.  She knew that I intended to dress up, but that was the only discussion we had.  When the day came, I did not have anything better than renting a movie to do.  Lame…  I know…  But it was some of the best lameness I had ever had!

But… in some ways, it was a non-event.  I LOVED being out in public, but it was no big deal otherwise.  No one cared how I was dressed other than that they looked at me.  I was on display, I suppose.

From → True Stories

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