Halloween and Cross Dressing in San Francisco

 

Halloween and Cross Dressing in San Francisco

Mark - Louanne - Me

As a young adult I loved Halloween. I used it as an excuse to be decadent, to do things I would not generally do. It was a night of outlandish behavior that could include drugs, alcohol, and smoking cigarettes. I smoked when I was young but quit for the last time when I was 25 and moved to Eugene. However I would allow myself to smoke on Halloween. I rarely dressed up as anything specific but rather would just select a hodgepodge of things that might suggest something interesting. I was never much of a planner so I would usually be stuck with whatever I had laying around or more likely whatever my friends had laying around at the time.

In the fall of 1978 I had recently moved to San Francisco and was working down the peninsula in Burlingame. October came around as it seems to every year and that meant Halloween was coming up. Lacking any imagination for a costume, I decided to dress as a woman. We, my roommate Mark and I, were invited to a party by our other roommate Louanne. I was at Louanne's friend Candy's house in Pacifica. Pacifica is a coastal town roughly 7 miles south of San Francisco. When I think of Pacifica, I remember the long pier that jutted out into the Ocean. It was a great place to hang out, smoke a joint, and watch the waves roll in especially at night. It was even better if it was a bit foggy, which it almost always was.

Mark dressed up as my unsavory/sleazy date and Louanne as a roller derby queen. With SF having such a visible and significant gay community I had little reason to suspect that my cross dressing would be particularly unusual. I never considered that I might cause anyone discomfort. We arrived at Candy's and I immediately received quite a bit of attention from most of the women at the party. Other than maybe Candy, who I had met before, no one really knew either Mark or myself. It soon became apparent that the guys did not know what to make of me and were a little uncomfortable. I realized that even though I was just a recent resident of SF the people at the party only knew that I lived in San Francisco and the combination of me cross dressing and SF's reputation well, you get the idea . Mark and I played that we were dates, even initially dancing with each other. I noticed that the other guys stayed away from us, especially me. They were non too anxious for me to approach them. Of course that resulted in me eventually doing just that. I even asked one or two of them to dance at some point. They all backed way off. Maybe it was kind of mean, but I was having fun. As I recall Louanne and Candy were not happy with their reaction, but then they knew me. The party itself was more sedate than most of the Halloween parties I had attended in the past. However, all was not lost as the female attention I was receiving for dressing as a woman was fun. Given that as a single heterosexual male, a major draw of any party was meeting women, this was a costume worth remembering.

Candy's party was on Friday but my friend Larry had a party on Saturday itself. I needed to come up with another costume. I reused the tights, the heels, and the fake string of pearls from the previous night. I swapped the dress for a pair of cut-offs and I slit them up the side. I put on a simple solid colored long sleeved tee shirt and added a leather vest, a frilly scarf, and a cowboy hat. I don't know what I was but it was unique and the general consensus seemed to be that I was a gay cowboy. I got lots of positive feedback at Larry's party. As it got close to midnight the party decided to head down to Castro street, one of the gay sections of SF. I was hesitant given the way I was dressed, but I decided to go along, although I at least swapped my heels for some sneakers.

We got there and started walking around. It was a big party scene. The streets were filled with people drinking, smoking, and more. There was even a parade. I was getting lots of looks and more attention than I was prepared for from almost exclusively those of my own gender. We decided to go into a bar and get a beer. I ordered a beer and before I could get out of the bar I was fondled a few times, received a number of suggestive comments, and finally was the lucky recipient of a big full on the mouth kiss. It was a little more than I was comfortable with. I made a beeline for the door. I managed to make my way back to the street without further incident. I decided I should refrain from entering any more bars, just depend on one of my friends to buy me a beer next time. Out on the street I was still getting attention but not to the extent I had been in the bar. I decided to lose a few of my items like the pearls and scarf. Still I had to be on my guard and it wasn't long before I decided to just head home. I hadn't dressed appropriately and shouldn't have joined the group going down Castro. It was an experience that I will always remember, and it was my first real kiss with a guy. I did go down to Castro Street on subsequent Halloweens but always made sure to dress conservatively.

The next fall I was dating a woman named Joy. Joy was a tall (5' 11”) redhead. It was Halloween time and we were invited to a party at her friend's house. I was trying to come up with a costume when I realized that I probably could fit into most of Joy's clothes and she had a whole closet to pick from. I thought “When will I ever get a chance like this again?” So I decided to dress up in women's clothing for Halloween a 2^nd time. There was enough to pick from that I could find things that were reasonably comfortable to wear. The experience of dressing in women's clothing made me appreciate how good us guys have it. There's those shoes with heels (who came up with that?). There's the stockings and tights. Even the dresses are often restrictive not to mention that they are not all that easy to put on and take off. This is all before the make-up thing. Sheesh! Still, I thought I may never have an opportunity like this again. So I took the plunge.

We got to the party and just like last time I got tons of female attention during the party. I had lots of fun. Joy? Not so much and she was none too pleased about me and my behavior. Like I said, I had fun at the party but there was no fun to be had after the party with Joy. She was furious with me and didn't want to see or talk to me for a full week. I guess I should not do that with a date but hey, Mark didn't get upset with me after Candy's party...

I cross dressed on Halloween one more time after that. A few years later I went to a Halloween party at Larry's again. This time I dressed as a homeless bag lady. That was actually the most fun. The clothes were comfortable and I could act grouchy and obnoxious. (I want apologize to all you bag ladies out there I'm sure many of you have a very pleasant disposition.) Even as a belligerent slovenly old woman I still received plenty of extra female attention. Of course I am comparing this to the amount of female attention I normally received at parties. Looking back, perhaps I should have dressed in women's clothing more regularly. Or maybe I just look better in women's clothing. I had no idea cross dressing was so much fun. Hmm, you know, I often say that “Some Like it Hot” is my favorite movie...

Somewhere in my mid to late 30's I lost interest in Halloween and with that I think it's safe to say that my days of cross dressing are over, but my life isn't over and like the song says “Never say never”.