Halloween Outings

As you may have noticed, it was Halloween recently. Halloween was not traditionally a holiday we celebrated much in South Africa when I was growing up, but in recent years it has become increasingly popular, especially with middle class kids and their parents. All the dressing up is thus all a bit alien to me, but my daughters love it. Additionally, I have never been invited to a Halloween party before, so it just is not a thing in my life. Then this year I was invited to not one, but two such parties.

For the last 5 years we have had a neighbourhood ‘trick or treat’ get together where the kids and parents meet early in the evening and we walk around shouting ‘trick or treat’ at houses who have indicated their willingness to participate. This is very popular, especially with my eldest daughter, so I politely declined the invitations I received. Then my daughters were invited to a party held by one of the eldest’s school friends and my amazing wife suggested that she would take the children to the party allowing me to attend my party. This opportunity was accepted with both hands. Not only was it my first ever Halloween party, but it was also the first time I would be out and about in my home town without my wife… I was more than a little nervous.

My wife’s offer was made in the week leading up to Halloween, so I desperately spent a few days deciding which party to attend, deciding on what to wear and planning the day. I played with all sorts of ideas for a costume but eventually decided to bite the bullet and go and purchase one as none of the stuff I could cobble together at home worked for me. I found a cute ‘vampiressa’ costume consisting of a black dress with flared ‘skirt’, and a snake-skin effect bodice with matching high collar complete with ankh choker. All quite nice. My wife bought me a pair of lovely fish net stockings. I was unsure of whether to finish the ensemble off with a pair of black shoes or my stiletto-heeled knee-length boots. I tried both but eventually went with the boots. I hope it was the right decision. I managed to get some pictures of the outfit with shoes and boots. Please let me know which you think are the best overall effect.

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I was now presented with something of a conundrum. When I dress I do so in an effort to properly express my femininity. I deliberately do my best to be sincere and real and to not in any way ridicule women. I was very concerned that by dressing in costume this was the effect I may convey. But after some introspection I decided that as my intention is always to be honest and to reflect femininity as long as I followed my usual process I would probably be ok. This was of more concern than usual because of the nature of the events that I had been invited to.

I was very privileged to have been invited to two events, one at our usual trans friendly bar cum nightclub, Trouble, and the other an event hosted by Sharon of Lola Montez. This was an area very much outside of my comfort zone. Whilst I expected the majority of the guests to be ‘sex positive’ and thus hopefully more accepting of non-conforming gender identities, I was also aware that I was likely to be the only transgender person there, that I may be the only transgender person many of the guests had ever (knowingly) met and that not all ‘sex positive’ people are necessarily accepting of non-conforming gender identities. Indeed, some swingers (especially the ‘straight men’) can (I am told) be rather homo- and transphobic, perhaps more so than the general population? These are all concerns based more on hearsay than my experience so please do not take issue with the opinions. They are the concerns I had based on what I have been told rather than actual experience. I was not sure what the make-up of the crowd would be and wanted to make sure I presented myself and the community in the very best possible light. I was therefore a little nervous and did not want to do anything that may upset anyone. Not knowing anything about the guests added to my nervousness. I had decided to attend the Lola Montez event as it was something new and I am always up for something new. Going to the Lola Montez event meant that I would have to drive past Trouble on the way home and I could thus pop into Trouble, see my friends and so on. I could therefore get to attend both parties on the same night. What a win!

I dressed as soon as the girls were out of the house and managed to get from the back door into my car without seeing any of the tenants on our property. My heart was racing and I really battled to get the car out of the driveway, but I managed in the end. Heart racing I drove to the Lola Montez event. It was quite far away from home and it took me about 45 minutes to get there. On arrival I checked my appearance as best as I could and walked into the restaurant where it was being held. As I crossed the parking lot I was aware of more people than usual looking at me. Whether this was because of my own concerns, the fact that I was in costume or because I looked like a hideous ‘tranny’ I was not sure but I had come this far so I could not chicken out now so I boldly walked into the restaurant and was directed to the semi private area where the party was happening.

Here are some pictures of my look for the night:

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I was worried that I was late but I was one of the first people to arrive. Sharon wasn’t there yet and that made me a bit anxious but she must have briefed her co-host Juanita as when I introduced myself she immediately remarked that Sharon had invited me. I confirmed this and she welcomed me very sweetly. At this point it is worth noting that Juanita looked amazing. She is a pole dancing champion, pole dancing instructor and judge. If pole dancing gives you that kind of athletic, sensual and generally amazing figure, I think I must sign up, immediately. She was wearing a cat suit that showed her toned muscles off beautifully. In addition to the very athletic body, being a dancer, Juanita moves so gracefully the overall effect is astounding. Plus she is a really nice person… Anyway I was given my welcome drink and an angel card that actually did have a rather meaningful and pertinent message even for this old skeptic. I sat down and nursed my drink.

Sharon arrived shortly and I was very happy to see her. She looked very good in a ‘pirate-ess’ costume with some very impressive thigh high boots that she moved in with considerable ease (green-eyed monster alert). I stood up to say hello and I was immediately made aware of the perils of flared skirts. The ceiling fans were on (providing some welcome relief from the heat) and the downward draft of air was ‘bouncing’ off the floor and it blew my skirt up. Oops. Anyway we all had a bit of a laugh and that, paradoxically, helped to calm my nerves a bit. I think Sharon saw that I was a tad nervous and quickly ordered a tequila for each of us. She also very sweetly made light of the whole thing and we had a bit of a giggle at each others’ expense.

The evening got off to a slow start as we were waiting for some latecomers. I was somewhat surprised to realise that apart from an unaccompanied man (who I believe was the restaurant manager) I was the only non-genetic female there. I felt a bit awkward upon first realising this but then I thought, hang on, I am a woman (at least for tonight) and I have every right to be here, a point of view that was shared at least by Sharon. Nobody had anything to say (and Sharon confirmed that she did not hear anything said about me either) so all was cool. As Lola Montez is a ‘sensuality emporium’, the evening’s entertainment was themed around sensuality and sex. As an ice breaker, we were all asked to (anonymously) write down our ‘scariest’ (well it was Halloween) question around sex, place the paper into a hat and our knowledgeable hostesses would then try to answer for us. It was interesting what questions were asked. Frankly, openly and with no embarrassment. Clearly everyone felt very safe in the environment. I am fairly sure that if you had tried the same thing with a group of men you would have got a lot more bravado and far less value. The questions were all interesting and I think were  mostly of relevance to a few people in the room.

We then had something to drink (I ordered a more than acceptable cosmopolitan) and to eat (I had a lovely salmon salad). The next bit of entertainment was a lot of fun. We were each given a piece of paper and we were asked to each write a word or phrase (depending on the specific instruction each round) on that piece of paper before folding it over and passing it to the person to our right. The type of word or phrase (adjective, noun, verb etc) was given to us by the leader but the only other request was that it had to be ‘sexy’. We thus wrote a collaborative erotic short story. The results were hilarious… The only trouble was that after the last phrase was written we were asked to read out the story on the piece of paper we were left with. Terror! My feminine voice is not ideal and I typically try not to speak as much as possible when in non trans company as I am terrified of being laughed at. But I had no choice so I did my best. Nobody blanched, nobody laughed at my voice (although the story was a different matter) and everybody was polite and relaxed. I did do my best to be as theatrical as I can be and that may have helped me. This was a huge relief and has given me a lot of confidence for the rest of the evening and indeed the future.

After some chatting and socialising we had our last bit of entertainment for the night. It was announced that Juanita was going to teach us how to lap dance! Oh. My. Word. When I heard this I seriously contemplated leaving FAST. Not only was I terrified I was going to be the laughing-stock for just being me, but I was also very much aware that I make middle-aged white men dancing at a wedding look positively rhythmical. But I was there, I was enjoying myself and I was unlikely to ever get a free lap dancing lesson ever again, so I put on a brave face and participated with enthusiasm.

Juanita is an excellent teacher she showed us some very basic moves that even I could approximate and off we went. Don’t panic, we did not actually give another person a lap dance, we used our chairs as a dummy or prop and worked with that. What fun! I actually think I could do a half decent lap dance (even in my stiletto boots) for someone after that… Certainly a number of the other women were very proficient. I think I need to show my wife what I have learned some time. Although I will admit that climbing onto the chair nearly proved my undoing. But other than that I think I did OK. I may even consider asking Juanita for some lessons on how to move more gracefully as that can only help my presentation I think.

After the lap dancing we had a brief chat before I decided to leave as I wanted to meet up with my friends at Trouble. I had a lovely time meeting a number of the usual crowd, catching up on the gossip and meeting one or two new people as well as meeting for the first time in person a long time Facebook friend. Everyone was very surprised to see me out on my own as I am nearly always out with my wife, and as I arrived so late were all convinced I had snuck out of the house, possibly having drugged her and the kids. I tried explaining that I had come from elsewhere, but I am not sure I was believed by everyone. After about two hours I decided to call it a night as it was now nearly 2 am and I am usually in bed by 10 so I said my goodbyes and returned home safely.

I was deeply touched by the invitation to Lola Montez’s party but felt especially privileged to be allowed in to that environment and to be treated as ‘one of the girls’ by everyone. I certainly had a lot of fun and I hope I represented the community well. If invited to a similar party again, I would certainly like to attend and I think I will feel more at home and more confident. I was a little concerned as a number of the ladies were friendly to each other but were less so with me. I later found out that many of them were friends as they did pole dancing together with Juanita so it was purely that that was going on. Anyway a big thank you to everyone who made it a special night. I hope that I will get to see all my friends from Trouble soon and for longer.

One Comment

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  1. Not a fan of boots and see them as a necessary evil in winter. So by that you may gather that I would vote for the photo with the shoes. That is just me.

    Glad you had such a good time and well done on being brave on your own and for being outside of the trans * and also the gay scene clubs.


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