Crossdressing for Halloween is probably the ultimate fantasy for every crossdresser at least when they first begin anyway. I think like me everyone thinks it would be the safest way to venture out for the first time crossdressed in public. Although I thought of it I went out dressed for many years before finally going to a Halloween party. It was safe given by a crossdresser and her wife in their home. I got ready in my home and my wife sneaked me out the door keeping watch for neighbors.


After many years one of the CHIC members threw a Halloween party last weekend, Of course everyone was crossdressing for Halloween. My wife talked me into wearing a “Queen of Harts” costume. She was not attending with me so I was to go alone. That is not a big deal other than I was not staying at a motel. Motels often let you park right outside your door so you only have a few steps to get in the car. I was staying in a high rise Marriott hotel on the 7th floor.

Crossdressing For Halloween


I have stayed in this Marriott many times and am comfortable with it. The staff knows me and I think they are always interested in what I will be wearing each night I am there. I am always overdressed and I think the ladies approve of my taste.

Saturday night was different because my wife goaded me into getting dressed in my costume at the hotel. That meant I was going to be driving to the party dressed in it. I wanted to rent rent a second room just for that night to get ready but had trouble selling her on the cost.


All dressed and ready to go I ventured out of my room and down the hall to the elevator as the Queen of Harts. I was probably only 20 feet down the hall when I heard a door slam behind me. I would have company in the elevator going down and he showed up 2 seconds behind me. Fortunately he asked if I was going to a party and I said yes, to which he said well you look great. I thanked him and we got into the elevator.

Lucky me!

The usually quiet lobby was full of people checking in for a big wedding that night so I gave them something to talk about and left.

The party was about a hour away and was great fun but I left a little after ten. after changing into a more contemporary jacket, skirt and heels.

Another great crossdressing adventure.

Micki Finn


  1. Hi Micki,

    I agree Halloween is a Fantasy/Fun filled opportunity to dress. I love your story about once out the hall and in the elevator The experience I’d like to share for those going out dressed for the first few times, is make sure you’ve walked in the shoes you are wearing for the evening (pun intended) before you spend a long evening out & away from your Hotel/Home etc. My first time wearing Cat Woman costume years back… I decided to wear Sexy, Black, Platform Boots… unbeknownst to me,, I was not used to walking in those at all… Lol… had a rough time at first 100 ft out of my Hotel. But, I wasn’t turning back… good thing, event was short distance from Hotel.. otherwise, I would have had sore calves, feet, etc… From now on, I take another comfortable pair, in case walking/Dancing is involved (or tuck Ballet Slippers in a purse) You are smart in having your “Contemporary Jacket Skirt & Heels.” nearby, for adapting to an ever changing evening!


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