Flying Solo and Getting into Trouble

After our fabulous retail therapy session my wife drove us home. We returned home without incident although I am convinced at least one of the tenants saw me walking from the gate to the back door. Oh well, such is life. We had a cup of tea and chatted for a bit before I made us some tuna salad for dinner. We had planned on going out together but, due to her illness, she was feeling in need of a rest so she suggested I make the most of the opportunity and go alone.

I thanked her and tried to see if any of our friends were doing anything. Sadly there have been a few family related health problems in my circle of friends (just 18 months ago having a circle of friends who knew me, as well me, would have been completely unthinkable, how cool is it that I get to say that I now have a circle of friends?) so no one was going out. Then a friend said that she would like to meet up but that all her femme clothes were at another friend’s house. She said she would go there to get dressed which was cool, but by the time all this was arranged it was getting late, so she sadly abandoned the plan. Lesson learned, trans people need lots of fair warning and spur of the moment decisions are tricky!

I was not to be deterred and after attending to the patient and making sure she was comfortable and well enough for me to leave her alone I did a quick wardrobe change and touched up my makeup. This was something of a revelation. In the past, when doing a daylight and night time en femme excursion on the same day, I have always washed off all the makeup, shaved again and started from scratch. This is a drag and leads to all sorts of facial problems the following days. But despite having last shaved some seven hours previously (it was however a very close shave)  it all seemed fairly good. I hope my interpretation was shared by the poor souls I ran into later that night. I did not pester my wife to take pictures, so I do not have any of my actual outfit, but here is a picture of the dress I wore.HPIM0051This picture was taken over a year ago and my hair style has changed and I wore a different pair of shoes (the second pair of shoes, black platform sandals, that I had bought earlier that day) but the overall idea is there and I think you have a good enough idea of how I looked on the night.

I left the house without incident and headed to Trouble our local gay and transgender friendly bar. On the way there I noticed that there was a general power failure affecting much of the north western suburbs of the city. All the way to the club I noticed that the power was out but I was quite sure that they would have a generator. I arrived at the parking area and it was in total darkness. The service station was pitch black as well,  as were all the shops. Only a restaurant had some light and the place was practically silent. I was tempted to return home but as there were a few cars in the parking lot, I decided to at least take a look for myself. I fully expected Trouble to be closed but it was open! They had obviously been affected by the power failure and whilst they do have a generator there were some technical difficulties and it was not yet running.

The Trouble staff had put candles on all the tables and whilst there was no music, Hilton Smith (Trouble’s main man) is an excellent host and greeted me as soon as I walked in and invited me over to his table where a group of guys were chatting away amiably. It was almost eerily quiet (well eerily quiet for a bar anyway) but the drinks were cold and plentiful and we were able to chat away merrily laughing, joking and generally having a good time. I was (hopefully)  able to educate some people on some transgender issues and explain my personal points of view as well. I also got some insights into what gay men experience, some of which I was not fully aware of and I felt enlightened and educated. We also engaged in some light hearted banter, so all round the conversation was good.

After some time the generator kicked in and we had light and some music. We suddenly realised that the bar was actually busier than we had realised and that there were more than a few occupied tables. I think Hilton’s spirits improved a little as he had been fearing a very bad night and whilst it was not going to be a great night (from a commercial point of view) it was at least better than he had feared. Suddenly the power came back on and the DJ booth roared to life, the smoke machine started up and we were able to party.

Our group moved into the main bar area where there is a small dance floor and some pool tables. Initially I took up station at the bar next to a man and a woman at the bar. Heterosexual couples are not exactly common at Trouble but they are also not unheard of either so I thought they were just that. After a few minutes of me watching the pool game the woman next to me engaged me in conversation, complimenting me on my dress, which was nice. She asked where I had got it and I explained I had bought it from Zando (an online retailer) and I suggested that she should give them a try. I established her name and that she was out with her brother as they were celebrating a new job that one of them had been offered. We chatted some more, I complimented her on her very nice tan handbag and she then remarked on how toned my legs were. She seemed surprised that I only run and that I do not train at a gym, I decided not to go into my long sporting career which I believe has helped my legs look as they do.

It was at this point that I started getting concerned with the direction the conversation was going. I have always been incredibly naive when it comes to ‘dating and meeting people’. I am amazed to this day that my wife and I actually manged to connect at all. Thankfully she is less shy than me otherwise I think I would still be single. This naivete has not exactly been helped by nearly fifteen years of marriage. I did not want the woman at the bar to think that I thought she was ‘hitting’ on me if in fact she was not and I also did not want to lead her on if she in fact was hitting on me. The word ‘awkward’ springs to mind. I tried to subtly flash my wedding (real) and engagement (fake) rings that I always wear out, but she was not really paying attention.

I then had a very good opportunity to extricate myself, with some elegance, from what was starting to feel like a tricky situation. She asked me who I was with. This led me to to be able to say that I was in fact alone but that I normally came with my wife. I think this made it clear who and what I was without being weird about it. I was quite proud of my self, especially compared to how I handled being flirted with the last time it happened. I guess I am learning some social graces. Sadly this revelation seemed to draw the conversation to a close, so maybe she was flirting after all. Or maybe she just realised exactly how much older than her I was (I am guessing she was no older than 23) and decided that old fogey’s like me are best left to their own devices.

I was enjoying the music and felt like dancing. As I may have noted before, I am not much of a dancer, but as soon as I throw on a pair of heels I suddenly become  a bit less shy and self conscious and the desire to dance may come to the fore. I started moving as rhythmically as I can and even dared a few little shuffles and shimmies. I was a little self conscious dancing on my own but frankly I did not really care. I was there to have fun and so I determined to have fun.

After  a short time I seemed to attract the attention of one of the guys at the bar. He had been sitting at our table previously so I had some previous interaction with him and he had seemed a really nice and friendly person, but sadly I have no idea what his name is. We did a little dancing and shuffling around and he then asked me if I knew how to rumba. I replied in the negative. I have sadly never learned how to dance. He was a real gentleman and said ‘with legs like those you should’. It is always nice to be complimented and I must say I really enjoyed that. He then proceeded to give me an impromptu dance lesson right there. He was a great teacher, but I am sadly a poor learner. He was wearing sandals and I was terrified that I would step on his toes (possibly breaking them). This added to my anxiety and whilst I had a lot of fun dancing with him the stress got to me and after some time I beat a hasty retreat leaving him to get to know another fellow at the bar better (which I think suited them both far better as they were clearly quite keen on one another).

It was now getting late and I paid my tab before heading home. I arrived home safe and sound. My wife was sleeping soundly and I cleaned up before collapsing gratefully into bed. I had had a lovely day thanks primarily to my wife, but also in no small part thanks to the amazing people (Hilton, staff and clientele) at Trouble who are so welcoming of us transgender people. For anyone looking for a fun and accepting place, whether  to just hang out or even party, I can heartily recommend Trouble.

About the post

crossdressing, entertainment, reviews

One Comment

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  1. Congratulations on your solo outing. As I read your account I was fully expecting you to tell us of a negative experience due to your use of Trouble in the title, though it is the venue name. Also as I read I was amazed at a lone female entering a nightclub and then proceeding to dance, I assume initially alone. I suppose your environment was reasonably safe in this regard being a gay venue. As for the tennant you thought that seen you, they probably thought it was a friend of your wife, not you.


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