A Walk on the Wild Side

At the end of May, my wife was getting ready to return from Australia, and Michelle’s dating interest was working, so we both had motivation to get together on a Saturday night. 

After texting about what we could do, I took a stab at the Google machine. It turned up an interesting possibility–a Kink Ball at the same club we saw the burlesque show about a month earlier (when I wore my Won-Dee Woman dress, to multiple compliments). 

A look at the FAQs for the event (the website showed similar events in Las Vegas and Detroit) increased my interest. 

Here was the first.

How should I dress for your events?

There is no enforced dress code, but we encourage guests to dress in fetish and costume attire for the events. Be creative and don’t be afraid to dress kinky. Fetish attire is strongly suggested but not required. Private parts on men and women must be covered (men do not have to cover nipples).

And the second? 

Is cross dressing ok?

Yes cross dressers and TG are allowed and encouraged. You can feel comfortable to dress whatever way you like. This is a very open minded crowd so dress to impress!

I was sold after the first; the second was the icing on the cake. I was game, Michelle was game–and I bought the tickets.

The only other decision is one I often face: what to wear?

Recently, an online friend from a crossdresser forum, Sandi,sent me a large box of her stuff. Given her personal circumstances, her dressing–best described as often bold–was going on hiatus, perhaps permanently. Sandi had reached out to me, asked if I was interested in inheriting some of her stuff (yes, absolutely). Part of the collection were three corsets (which increased my collection from zero to three), a set of forms (several sizes larger than my existing forms), and numerous larger cup bras to accompany the larger forms.

I chose one of the newly gifted corsets, a bra, and the larger forms. Over the bra and corset combination I wore a black Akira mesh top (worn once), red fishnet stockings, and a pair of black bikini swim bottoms. I thought about some higher heels, but in the end settled on a pair not quite as high, but more comfortable. 

Michelle chose something more adventurous–a corset top (although see complained about her boobs being squished, a problem I did not have, because hers are real), along with a pair of mesh stockings, some fake leather leggings, and otherwise nothing underneath her (very cute) backside. She also wore a pair of heels I gave her, ones that I thought about wearing (we have matching heels, mine a size larger). 

FWIW, I wore those same stockings and heels when we went out for Halloween 2021, although my backside wasn’t quite as exposed as Michelle’s.

We took a few pictures before we left. Needless to say, I didn’t take a lot of pictures at the club itself, because the other patrons deserved their privacy.

We parked near the club, and the walk into the club was uneventful. We entered, found seats, and ordered drinks (I buy and Michelle flies, which is why I was able to get the fun picture of her backside, which she did allow me to publish here). Michelle usually posts pictures of our outings on Facebook, sometimes with a smidgen of me, sometimes with my picture (as Michelle and I  have only one common Facebook friend–my friend Ms. Dee-ism–I don’t worry about those posts), but there was no Facebook post from this night (I’m sure you understand why).

The patrons were about 50/50 men and women (at the burlesque show there were more women than men), most in various forms of kink wear. There were a lot of fun outfits, many latex and some leather. Obviously from my perspective, the women’s outfits were a lot more interesting. There was a stage in the front, and events on stage, but I couldn’t hear or see them well–and I was more interested in crowd watching anyway.

A married couple next to us at our shared table–I’m guessing mid-thirties–with three kids, from about an hour away in rural Missouri (rural Missouri is not the most progressive of areas). I asked the wife about who was watching the kids (one of the grandmothers), and whether the grandmother knew the reason why the couple was in St. Louis (a hard no). She in turn asked questions about my dressing, and as I always do, I answered honestly. I always offer to answer any questions someone might have, so that person can better understand why I like to go out dressed. The husband was definitely interested in Michelle (not hard to understand why), but TBH he came across as a little creepy.

There was also another area upstairs, so Michelle and I decided to venture upstairs. Between the stairs–somewhat steep–my two margaritas, and my heels (I usually say alcohol and heels don’t mix well for me), I carefully climbed the stairs to see what was happening there. There was some mild kink equipment–including a bench for spanking–and a woman doing some minor rope bondage on a couple of other women.

I took a seat along the wall and again went into observer mode. There was a married couple, probably mid-forties, with a similarly aged female friend. The wife was seated next to me. Both the wife and friend were wearing black latex outfits and eye masks. The friend volunteered to lie on the spanking table, facing us, or more accurately, facing (and eyeing) Michelle. The friend started getting spanked by a guy, but was seemingly bored. After a few minutes Michelle walked over and began spanking the woman, which Michelle seemed to mildly enjoy.

At the same time, I was talking with the wife. In the small world category, she went to my high school, about twenty years after I did. I was wondering why she, her husband, and the friend came to an event like this.

I read and listen to sex advice columnist/podcaster/author Dan Savage, and he always says that half the people you meet at events like this are kinky, and the other half are people who fell in love with the kinky person. He also says that women often grow into their sexual identity later than men do. I have found that women are usually more inclined to talk to a guy dressed as a woman (me), than if I was dressed as a guy. I’m curious, and I’m willing to ask questions, because I am interested in the answers (all while trying to have them understand I am not hitting on them, as that would indeed be creepy). 

Often, couples hide sexual interests from their significant others (several crossdressers I have met have never told their wives about their dressing). My wife knows I dress, but she would have no interest in going to an event like this, much less going out with me dressed. I am curious to know how the people overcame those secrecy obstacles in order to both end up at a kink ball, dressed in latex and eye masks, and coming with a friend. The discussion with the wife was more interesting to me than the idea of spanking (or getting spanked).

My GG friend Renee–who helped me dress many moons ago, and loves seeing me dressed these days–and I have shared fantasies about going together to a sex club (in a previous lifetime, we were what would be described today as FWBs). 

Her husband would not be interested, nor my wife, but Renee and I would like to go. Given thousands of factors, it has a .00001% chance of actually happening, but fun to contemplate. In the meantime, going to a kink ball in (semi) kink gear (my outfit was pretty mild compared to most of the others) will need to suffice.

As to my sexual interests and dressing, it’s somewhat complicated. I’m not sexually attracted to men, only women, but dressing as a woman to try to attract women probably isn’t the best strategy for success in trying to attract women! 

Also, for me, the IDEA of dressing is far more sexually stimulating than the dressing itself–or the idea of someone wanting or ordering me to dress (although I am very willing to do it on my own). However, I Dee-finitely can feel sexy in a dress and heels. 

Like I said, it’s complicated. 

By asking questions of others–and women are a lot easier to ask than men–I’m trying to better understand my own sexual interests.

By this time, Michelle and I were ready to go. I carefully made my way down the stairs–pretty much sober at this point, so the only issue was stairs and heels.

The exit was through an adjacent room, with a DJ playing some sort of (what I perceived to be) Arabic music to a group of about fifty men and women of middle Eastern descent (guessing; don’t know for sure, and I wasn’t going to ask), dancing and singing to the music. It was an interesting juxtaposition–the two of us dressed in kink gear, walking past a group of individuals more associated with very conservative modes of dress. Perhaps a fitting end to a fun night????

Would I go again if I had the chance?

YOLO. In the words of Renee, “Fuck Yeah”.