Allison M.

Thoughts on life, fashion, fabulousness, and (oh yeah) dressing up from a full-time male who's a part-time female

#ThrowbackThursday: My first night out as Allison

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Brace yourselves and avert your eyes if you’re squeamish, because I begin this post with a younger, perhaps not-so-flattering photo of yours truly from many years ago.

December 26, 2004 Photo 1

Yep, that’s me, sporting a leopard print shirt, awesome leather pants, and a really weird pose on my first night out in public as Allison.  I remember the date: December 26, 2004.  That Christmas weekend was a pretty busy one for me.  I spent the holiday as I usually do with my family out-of-town, staying Christmas night with them and headed back to Madison the next morning.  At that time, I had lived in Madison for 2 years and, recognizing that this city is pretty open-minded, got the itch to start expressing my feminine side a little more.  I had already conducted frequent conversations with fellow crossdressers in chat rooms and the like; though those I conversed with did not hail from the Madison area, they did offer words of advice and encouragement.

One member of that online group stepped up and offered the chance to get together, dress up, and attend a drag show at an LGBT club here in town; I accepted, and we agreed to meet up on the night after Christmas.  Before then, I had to start making plans to make my feminine side presentable.  I mean, this would be the very first time someone else in Madison would see my feminine side.  The first thing I had to do was purchase a decent wig; no, not one of those cheap ones you find in a department store every Halloween, but one with more quality than that.  I wasn’t sure if any shop in Madison that specialized in wigs would be welcoming to a girl like me, but I did find a selection of wigs at an intimate/exotic clothing shop on Madison’s east side, a shop that, sadly and coincidentally, would close its doors a few months after my visit there.  I was upfront to the clerk there that I was buying a wig for myself, and she was so understanding and accepting.  I was unsure as to what wig style would be perfect; all I was sure about was I wanted a style that flattered my face shape and was easy to maintain.  The clerk picked out a sandy colored short-bob wig, and we went into a back dressing room where she offered tips on trying it on.  Putting on the wig and looking at myself in the mirror, I immediately loved how it looked on me.  So, off my head and into the shopping bag the wig went (the clerk also threw in a wig head for free).  I also went to the department store that evening for a leather jacket and purse.

The afternoon of the outing, I still hadn’t purchased another important ingredient: Makeup.  So, after I returned home from my sister’s house, I headed to Target, went through the sliding doors, and headed to… the electronics department, where I was just in time to catch Peyton Manning of the Indianapolis Colts break the NFL’s single-season touchdown pass record. (It was the last day of the regular season and, what can I say, I’m a sports nut?)  After that was out of the way, I made my way to the makeup section to snap up some lipstick, eye shadow, etc.  Back home, I gave myself the full treatment: Shaving the face, shaving the legs (even though I would be wearing pants that night), makeup, and wig brushing.

By 9PM, I was all dolled up and all ready to go.  I met up with my evening’s companion at her house, where we chatted briefly and I talked her ear off about my background (I didn’t mean to go on and on).  While I had my wig on, she had long enough natural hair to put in a feminine style, a .  Both of us all good to go, we went together to Club 5, a long-time LGBT club on Madison’s south side just off the Beltline Highway. (I will talk more about the club later in this post, and it’s pretty important.)

Our time at Club 5 was simple enough: We sat in the back of the club, watched the drag show (raunchy and awesome performances, by the way), conversed a little bit (or tried to over the loud music), and headed to my companion’s place to chat a little more before I headed home. (Luckily, I took the next day off from work so I could sleep off the long yet fun night.)  Of, of course, I had my just-purchased digital camera in my purse since my first night out as Allison was, to me at least, a momentous occasion, so I asked my companion to snap a couple of pictures.  The pics, as you can see above and below, were a little bit blurry, and I posed rather awkwardly, but they are tangible proof of my first venturing out as Allison.

December 26, 2004 Photo 2


As for that evening’s companion and I, we got together just a couple more times, though not for drag shows.  She was part of a Milwaukee-based transgender/crossdresser group, and she invited me to attend their monthly meetings.  I went along with her for a couple of trips, along with one I took by myself.  The groups were, naturally, eye-opening, welcoming, and supportive, not to mention lots of food: Pizza at the end of the meeting for everyone, while a few headed up to Bakers’ Square for desert.  Though I do note that the meetings were informative about the struggles of TG’s, I didn’t feel as comfortable as I hoped going there.  Please don’t misconstrue that statement as being unappreciative or anything; I did enjoy my visits there, but I imagine it was either my shyness, my sense of unsureness about my feminine side’s place in my life, or even the long drive from Madison to Milwaukee (much more likely the shyness, since I still consider myself a socially awkward person) that led me to fall out of touch with my first night’s companion and her group.  I do hope, though, that the people I encountered there continue to live life as their true selves.  Though I did not completely share the journey with that particular group of TG/CD sisters and brothers, I take heart (and I hope they do, too, if they ever read this) in knowing that even my little bit of time with them helped contribute to my gradual maturity and confidence as a crossdresser.

Oh, and just as I had photos from my first night there, I also had a couple of pics from my time with the Milwaukee support group.  They met at a LGBT community center just north of Milwaukee’s downtown.  (Oh, and yes, I do wear eyeglasses, though if you frequent my Flickr gallery, I usually go without; even though I have to squint at the camera to see where the lens is, I feel I look more feminine without glasses. I think it’s because those are my everyday glasses, and though they are unisex frames, I still get the sense that I look like an everyday male with them on.  Oh well.)

GGG January05 2 (updated)


Oh, I mentioned above that my first night out as Allison was at Club 5.  Indeed, the club has been a mainstay in Madson’s LGBT community.  The club started out in 1998 and for a while was pretty easy to spot from the beltline with its pride rainbow-colored triangle on the north side of the building (it was removed several years ago).  After the original owner passed away in 2008, Club 5 was sold and eventually rechristened FIVE Nightclub.  I think the timing of this post and my mentioning of FIVE is a little bit fortuitous as it coincides with this sad news:  The owner of FIVE, citing in part a steep rent (I know that feeling) and a little bit of a desire to do other things, has decided to close FIVE for good after Sunday, April 26.  If you want verification, here’s the message on the website (if that no longer works by the time you read this, here’s that same message on Our Lives’ Facebook page).

In his message, the owner mentions his nervousness when he first ventured into the club 13 years ago.  He still went inside and met the then-owner of the club, which he cites as a life-changing experience.  He uses a gracious tone in talking up FIVE’s role in the Madison LGBT community, and I want to highlight this paragraph from his message:

What I was in store for was the most AMAZING time of my life. To watch the kids from the other side of the chicken fence turn into leaders of our community, get engaged, get married, have children…Wow! To ALL the incredible employees current and passed I worked with …Thank You from the bottom of my heart for your efforts, hard work and providing an awesome environment for our community…..

Yes, though there are still naysayers and whatnot, “the kids from the other side of the chicken fence” sure have become a big part of the Madison community as a whole:  Open-and-out citizens committed to relationships and families, business leaders, community leaders, government leaders (even a United States Senator).  Big, momentous events that affected the community, including the right of same-sex couples to get legally married in Wisconsin.  All that, and FIVE was there to see it.  Though I am still the shy type, and though I’m not really a nightclub person (and though I’m not sure if I’ll have the chance yet), I hope to go back to FIVE one last time before it closes; I owe it to them as it was the place where this awkward crossdresser first felt welcome.

Now, to borrow a famous line from “In Flanders Fields,” FIVE is ready to “throw the torch” from its “failing hands” to other LGBT-friendly clubs, businesses, etc. in Madison.  Here’s hoping that, though FIVE will be fading into the history books, Madison’s LGBT community will continue to carry the torch of LGBT pride that FIVE helped lit and held; may it be ours “to hold it high.”

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Author: Allison M.

Full-time middle-aged male. Long-time overworked office drone. Part-time female fashion plate. Amateur fashionista (emphasis on "amateur"). Admirer and supporter of those who are fashionable, fabulous, and friendly. A little bit silly. Absolutely nowhere near perverted. I am a real human being, just like you. Able to share thoughts about my life experiences, fashion sense, and the world at large despite middling grades in high school creative writing class (but at least I do look cute when I'm writing, so that has to count for something).

5 thoughts on “#ThrowbackThursday: My first night out as Allison

  1. Pingback: Allison’s random stuff (4/27/2015 edition) | Allison M.

  2. Pingback: #TBT follow-up: Going (way) out (and doing it again?) | Allison M.

  3. Pingback: Allison examine “La Cage au Folles” | Allison M.

  4. Pingback: An addendum to my Saturday night | Allison M.

  5. Pingback: Random stuff (6/17/2016 edition) | Allison M.

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