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Halloween Party Crossdressing

November 5, 2012

My wife and I attended a Halloween costume party.  My wife is slightly tolerant of my crossdressing.  She can normally be described as being non-supportive about it.  However, she agreed to go with me to the party and with me dressed.  She is actively trying to stop shutting out this side of me.  I have tried to communicate that I do not want to keep secrets from her.  Regardless of all of that, my crossdressing makes her very uncomfortable.

For the party, she wore a men’s suit and I wore a black dress and heels.  I was in all women’s clothes, but I had my man head.  My wife was in menswear with her normal head as well.  Leading up to the party, she was very uncomfortable, but she and I managed to keep her from bailing out.  When we walked in at the party, almost no one reacted to us.  Most of the party-goers were in costumes.  I was the only crossdresser.  But we were just two more people in costumes.

Only a few of the people at the party knew us.  We met and talked to several people.  I ballroom danced with a few women.  My outfit almost never was acknowledged, except for when I mentioned adjusting to dancing in heels.  I do not think anyone raised an eyebrow.

Here’s the best part: My wife relaxed.  She started having fun.  In spite of my outfit, she was comfortable with me.  We danced and smiled and fell in love again on a date that was very overdue.  She has  not smiled at me like that in a long time.  I was so happy.  We were so happy!

Annoying part: I felt like I was just at a party.  I hardly knew I was crossdressed.  Granted, I had to do that thing to the back of my skirt when I sat down and I had to remember to not walk perfectly in my heels…  But I barely got to enjoy being dressed en femme.  I was always either dancing with my wife or talking with people at a table.  Some people who sat near me did not realize how I was dressed until we were near them on the dance floor.  It was almost boring to be in a dress in public with my wife for the first time.  That should not be true!

One more note. People at the tables at the party would make comments about my outfit or would joke about who was leading when we danced, but the various women I danced with did not care about being up dancing with a man in a dress.  They did not mention it.

After the party while we were at home, I asked my wife if I could try on one of her skirts.  She said yes like it was no big deal.  I tried it on and came out in front of her in it.  She looked at me and reacted about as unconcerned as the ladies at the clothing stores react.  In my opinion, that was a BIG change.

Summary of the evening: I felt pretty normal.  I was unusually comfortable both in the dress and also on the floor dancing.  My wife had fun with me even though I was crossdressed.  I love my wife!


From → True Stories

  1. Halloween is the socially-acceptable excuse for many of us to make our first foray into public crossdressing. It was mine, as well. I’m finding your stories to be interesting. How people react to you (and me) is never predictable.

  2. Chris permalink

    One year for Halloween my wife and her best friend who was going through a nasty divorce decided they just wanted the three of dress up and hand out candy. I suggested they dress up as slutty fight attendents, they werent real keen on this idea, but a few days later, they said they would do it if also dressed as a fight attendant. At first I was against it (kind of) but they were pretty convincing and I figured, why not after all it was Halloween. Two nights before, my wife had me shave my legs. The night before my wife’s friend came over, we had a few bottles of wine and they painted my toenails and finger nails. Then on Halloween my wife did my make up, had me put on a black bra and black bikini briefs. Next came Suntan Sheer Energy Pantyhose. I slipped on the navy costume, it said one size fits all, but it was definitely made for a woman and was pretty short on me. Once I put some black heels on you could see the bottom of my control top from the hose sticking out of the bottom of the skirt. A blonde wig went on my head and I was done. My wife said her and her friend would get ready next. They went into the guest bathroom and got dressed together, I was still in my bedroom too embarrassed to come out in front of my wife’s friend. Finally they said they were ready and chided me to come out. I did begrudgedly and to my surprise, they were dressed up as pilots! They got a big kick out of this and made me hand out most of the candy. They took quite a few pictures, and teased me most of the night. They kept asking me if I enjoyed wearing pantyhose and high heels and said it was good for me to know what they had to go through on a regular basis. All in all it was a pretty fun night, I would certainly do it again next year!

  3. For folks like you and me the very act of getting out of the house into the civilian world, even at a Halloween party, while dressed in hose, heels, dress, etc is exciting and inovate. For a woman to wear hose, heels and a dress is about as ho hum to them as your or me in chinos and a polo shirt.

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