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Those of you who know me will be aware that I am very much in the closet and only dress on trips away from home. In fact my first time venturing out as Sophie was on a solo cycling trip a couple of months ago.
A lot of my everyday life is dominated by spreadsheets and databases. Don’t get me wrong I love my job but it is sometimes missing the more aesthetic aspects of life. I find that my cycle trips down quiet English country lanes can help fill this gap. It gives me a reset from work, a chance to enjoy nature and to reassess life’s priorities.
For me being able to put on a pretty skirt at the end of a busy month at work is a very similar feeling to freewheeling my bike down a hill through a picturesque Cotswold village after a long climb.
Preparations for this trip started several weeks ago. I was determined to have a go at wearing high heels. High Street shops would be no good (size 11 mens’ UK) but I found I a pair of pumps with 3″ heels on Amazon. A few days later they arrived. I could just about manage to squeeze my feet in but walking on them was almost impossible. I suspect I looked a little like the scene in Cinderella where the sisters try on the slipper!
But there was still time for me to return them and order larger ones before my trip. Unfortunately the only ones I could find were sandals with 5″ heels. Being 6’3″ wearing such shoes is arguably ludicrous. But I got them anyway for the fun of trying them out in the hotel. I think in terms of dressing I am probably at the same developmental stage as a teenage girl, desperate to try out all of the “grown-up” things like bright lipstick and high heels. I suspect I will get that out of my system soon and start acting more my age!
Day 1
When I was researching my trip I found out that a group of CDs meet in a pub in the city where I was staying. I quite liked the line on their website “we don’t care if you are less convincing than a wrestler that has eaten a lipstick, you are still welcome here”. I identified with that and so asked if I could go along. I got dressed and made up in my hotel and debated with myself whether to walk or get a taxi. I wasn’t feeling overly confident and opted for a taxi but when after 15 minutes it still hadn’t showed up the decision was taken out of my hands. It was a sunny evening and so quite busy which meant a really nerve-wracking walk. But after twenty minutes I arrived at the pub.There were five CDs there and a man who I think was the ex-partner of a lady who had transitioned. They were all, I think, very experienced dressers and the conversation was more about politics and the news rather than girly things like the best places to shop and makeup tips. To be honest I found it a little bit gloomy and negative. I mentioned CDH at one point and one of the ladies said that she tried that but found there were too many Americans and Australians! (I think the geographical and social spread of the ladies of CDH is what makes it such a wonderfully special place!). That’s said, I was grateful for them including me and it was really interesting to hear their stories.
Day 2
My original plan was to go out dressed for dinner every evening of my trip. But it didn’t seem right at my next location. The hotel restaurant was a little too full of alpha male types. So I ate in my man clothes and spend a relaxed evening dressed in my room, chatting on CDH.Day 3
Wow what a day! This was the one occasion when I had to get the timings right on my cycle ride because I had an appointment for a make-up lesson! So after an early breakfast I set off over the spectacular Severn Road Bridge (with apologies for those of you in San Francisco, I appreciate that we have nothing to compare with the Golden Gate). I arrived in Cardiff, Wales with plenty of time to spare.I’d spent a long time planning this. When I made my initial enquiries I emailed as Sophie but I made it clear that I was not a GG. The last thing I wanted was to end up with an appointment with an artist who is not comfortable working with CDs. As it turns out I couldn’t have chosen better. The artist’s name was Victoria and she made me feel completely relaxed. Although she specialises in wedding makeup, she has a couple of regulars who are CDs. I told her to assume that I know nothing about makeup (which is about right!) And so she led me through the stages step by step. She did the right hand side of my face and I attempted to copy on the left. Her aim was to accentuate any feminine looking features to draw attention away from the more masculine ones. And so, for example, we spent quite a lot of time working around my eyes. I have quite long eyelashes for a man apparently and I was amazed what difference a little mascara made. She showed me how to contour using different shades to make my face look less long. And I have to say that given the starting point she did an absolutely wonderful job. I certainly felt so much more feminine at the end and we had lots of fun in the process.
With the new founded confidence that I had in my look I decided to go to a nightclub. It was a gay bar but with all sorts of people there. Initially I was just happy sitting by myself with a gin and tonic catching up with a bit of chat on my phone. But then a couple of Scottish GGs came over. They said I shouldn’t be on my own and they took me under their wing for the rest of the evening.
They were great! They treated me completely as “one of the girls”. We catted, danced (rather more than I would normally), touched up each other’s makeup after it was smudged by the drinks and rescued each other when we were getting a bit too much attention from a guy!
Wow, those girls certainly knew how to party … and how to drink! I don’t drink all that much anyway and still had a long way to cycle the next day. So at the end of the evening I made sure they were safely poured into a taxi before I make my way back to my hotel.
I am so grateful for the kindness they showed me. It was a proper “girls’ night out” that I will remember for the rest of my life.
Day 4
After a late night last night and a total of 180 miles cycled, I was too exhausted to go out but enjoyed another night in as Sophie.I find the cycling gives me a chance to think, such as about where I fit in in the wide spectrum of cross-dressing. I’m not sure that I am much closer to an answer but I do recognise that in most areas life I tend to err on the side of caution. Hence, for example, remaining in the closet. But just occasionally I think everybody needs a little bit of risk and excitement and I certainly have no regrets whatsoever about the two recent cycling adventures. I’m not what is next for me but I have plenty of really lovely memories to keep me going until then.
I liked your story! I have always said that we are on a journey. There will be positive thing, negative things, unexpected things and revelations. It is helpful to give some thought to these events and not let them get lost in a blur as they are bits and pieces of the entire picture.
Before I had a mild stroke about 3 1/2 years ago, I was also a road cyclist. I was good for 55-60 miles and the majority of my riding was spent by myself. I never did dress as I was unsure about what to do about makeup as I never go out dressed without it. Anyway, I agree that cycling by yourself is a great time to think about and process events in your life. There’s something about physical effort that seems to quiet the background noise and allows you to focus on one set of thoughts. Also, I find that sometimes when your thoughts are diverted, other useful thoughts or insights pop up. You just never know!
Regarding shoe resizing, there are one or two threads here about that issue. To recap, there are sprays for the inside of leather shoes. Once sprayed, either wear them or insert shoe stretchers. Alternatively, insert plastic bags filled with water into the shoes and place them in the freezer. The volume of frozen water is 4% larger than its liquid volume. The stretchers and water method also work on synthetic materials, but the spray only works on actual leather. The trick is to go at this in iterations as big moves may tear the glue apart. There is also at least one thread about walking, so that may also be of help.
You are right about developmental stages. We never got the advice and counsel of mothers, sisters, aunts, etc. so we have to work up on this knowledge in other ways.
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