Confirmed bachelor, it’s a wonderfully old-fashioned phrase, the tacit tolerance of another age. While I wasn’t coy about my sexuality, or crossdressing, I had adopted the lifestyle the phrase suggests. Having a found a comfortable routine, I was content to keep life at arm’s distance, living vicariously through the books with which I surrounded myself. Turning forty exposed a few cracks in the edifice; the friends of my twenties began to raise families, or die. I didn’t know which I envied most. Forty’s about half way with my family, and while not particularly lonely, the prospect of an extended, solitary old age appalled me. Something needed to be done.

Basingstoke had little in the way of a gay scene, when London’s only two stops away on the express there was no great demand for one. I had travelled up to Town a few times when I first moved into the area, but Old Compton Street held no attraction for me, or I for it. The urge to develop muscles, had never taken me, diet and exercise kept me trim, any further would conflict with my transvestism. I took great pains not to parody femininity when dressed, something a sculpted parody of masculinity would make even more difficult. There seemed nothing to do, but fall back on those colleagues who had attempted to set me up over the years.

Carole in Customer Services had long seen me as a perfect match for her brother Jason, and was more than happy to pass on my telephone number, with the promise of a glowing reference. As I’ve something of a reputation in work for being a martinet, I was unsure how she would ‘big me up’, but I placed myself in her hands.

Jason was a couple of years older than I, and as camp as a row of tents. While I had been burrowing deep in my closet of shame, he had been marching to create a society where I could emerge when I wanted to. It wasn’t that I didn’t appreciate his efforts - my ‘coming out’ had been relatively painless - but he conformed to every gay stereotype, short of arriving for our date in full Tom-of-Finland regalia. Cargo pants and a too-tight, white T-shirt were however, as much of a uniform, he even had the moustache. Still, he was good company, so I invited him back for a nightcap.

“Have you read all these?” Jason gestured to indicate the bookcases lining two walls of my living room.

“Pretty much,” I picked up the copy of Genet’s ‘Our Lady of the Flowers’ he’d removed, and slid it back into its place. As guided tours go, my flat is a fairly boring subject, unless you’re impressed by row upon row of books — Jason wasn’t.

“Carole says you look great in drag. Want to show me your frocks?”

“It’s not drag as such,” I said, opening the closet door, “I just wear them around the house mostly.”

“Wow, how many pairs of black trousers do you own?” It had to be the least enthusiastic ‘wow’ uttered in human history, and hung in the air while Jason flicked through the rest of my female wardrobe.

At least I didn’t have to worry about sitting by the phone waiting for him to call. Carole told me that Jason liked me, but I wasn’t his type - too ‘straight acting’ was the verdict. It was a description I couldn’t deny with any great conviction.

Reserve had always been the keynote of my personality, introspection even, that only ever really slipped when I was dressed. Not that many had the opportunity to meet me then, dressing was something I did at home, especially when I’d had a bad day at the office. It was as much putting on another personality - not necessarily feminine - as another set of clothes.

Word spread that I had put myself ‘on the market’, as had Jason’s impressions, and finding a partner for me became the focus of office gossip. There were, I understand, several candidates, whose suitability preoccupied the smokers, bathroom chatters, and vending machine loiterers for weeks. Eventually, all the factions fell in behind Tina-in-Accounts’ next door neighbour, a bookish type, who liked classical music, and wasn’t too good looking.

Owen’s musical tastes were a pleasant surprise; ‘classical music’ meant Radio Three rather than ClassicFM, and his choice of books wasn’t too far from my own. We discussed lieder over the starter, Primo Levi over the main course, and swapped anecdotes about the ‘gay community’ while waiting for dessert. Things only began to turn sour over the sweet.

“I don’t see myself as a drag queen,” it hurt to have my own prejudices thrown back at me, “my transvestism has always been separate from my sexuality.” I had never had much luck explaining that to anyone, not least myself. They both became manifest around the time I reached thirteen, although since then, I had recognised a few resonances in my childhood years.
Owen left looking unconvinced, and I spent a fruitless weekend by the phone.

The general consensus in work was that I was a hopeless case, the matchmakers moved on to the homeliest of the modern apprentices, and I was thrown back on my resources, such as they were. Crossdressing seemed to be the main sticking point, yet even in the most liberal times few men would admit being attracted to anyone transgendered. If I was to locate a partner who didn’t object to my occasional desire to appear feminine, there was only one place to look.

A transgendered ‘networking site’ sounded more positive, or at least less grubby, than much of the internet alternatives, still, I had to filter a lot of inappropriate replies ‘admirers’. While I wasn’t looking to another ‘girl’ for a relationship, I did make some new friends, who weren’t exasperated by my quest, although no one who had been in a similar position.

Phil had been quite attentive, while not pushing for an early meeting as so many others did. We chatted online for a couple of weeks, before graduating to telephone conversations, and an invitation to my home. I’m a little ashamed to admit it, but I’m as susceptible to flattery as anyone, and slept with him that first night. Sex while dressed up — although ‘dressed’ is rather an overstatement — was a novel experience, enjoyable enough to repeat several times over the following weeks. The telephone conversations continued on our ‘nights off’, and I found myself growing closer to Phil than I had with any other partner I’d had. It was such a shame he had to spoil it.

“What are you doing this evening?”

“It’s eight o’clock already, so I’ll probably just have a bath and an early night,” I had a suspicion where this was going.

“Can I come round?”

“OK,” I said cautiously, “it’s just I’ve had a long day, and I don’t feel like dressing up.”

“Oh,” the line went very quiet, “I’ll probably give it a miss then, I have an early start in the morning myself.”

We repeated this conversation at least once a week from then on. I loved Phil coming around, loved the flattery, even began to love him, but he couldn’t bring himself to visit when I wasn’t dressed as a woman. Some weeks I made the effort to be what he wanted, whenever he wanted, but the sheer effort of transforming myself on a nightly basis began to take its toll. It really hurt to break it off, I’d had my first glimpse of a proper relationship, it was just that it excluded a whole part of my life. Love me, love my dog maybe, but I was fond of the dog.

Slipping back into my comfortable, confirmed bachelorhood held no surprises, I’d always had a knack of compartmentalising my life, closing doors behind me. Changes had wormed their way into my life however. I found myself dressing up more frequently, and colleagues complained that I had become even more remote than I had been before. As I said, I had a reputation around the office for being a bit terse — laconic, if they were feeling charitable — but I didn’t think I was acting any differently than I had before. Perhaps a softer side had crept in when I was with Phil, I was sure, however, I could rebuild bridges where I needed to. The company’s summer party was only a few weeks away, it had always been a good way to break any ice accumulated since Christmas.

My appearance en femme at company functions had began ten years before, as a bold statement of who I was. Over the years it had become something of a tradition, which I tried my best to uphold. There was always a new dress, new shoes and usually a new wig. Part of the tradition was my taking the afternoon off to get ready, sometimes the whole day if I was feeling insecure. Not everyone might appreciate why I did it, but they at least recognised the effort I put in.
As always there was a ripple of louder conversation when I entered the room, at a barefoot six feet two it would be difficult for me to make a quiet entrance, even without heels. I was pointed out to new staff, who had perhaps suffered the sharp edge of my tongue, while those with whom I’d crossed swords found it within themselves to compliment me on my clothes, my makeup, my bravery, and as always my legs.

“Aren’t you getting a bit old for frocks that short?” Susan had done my make-up for the first party I’d attended, and ever since had positioned herself to be the first to judge how I looked.

“Everything’s too short, Susie, when you have a thirty three inch inseam,”

“False eyelashes too, you tart!”

“False everything, apart from the nails,” my fingernails were the only obviously feminine thing that I carried into my everyday appearance, and much envied, “now let your old boss buy you a drink.” Wrapping an arm around her waist, I steered us towards the bar.

Our company parties had a natural rhythm; predictably one of the ‘modern apprentices’ had far too much to drink and had to led off to a taxi; the most staid of the older women, was offering lap dances, and a group of warehousemen were nudging each other into asking me to dance. From past experience I only accepted if I was certain their beer goggles were not in place.

“Do you remember the year the old CEO followed you around all night?” Susan giggled.

“Oh God yes, if I’d taken every drink he tried to get me I’d be on the board by now!”

“You would be too,” her expression was suddenly solemn, “if you hadn’t outed yourself so spectacularly.” I’d heard that before, and it was probably true.

“Oh that’s nothing,” I didn’t like solemn conversations at parties, and launched into a comic account of my recent romantic travails. That kept us giggling until the party broke up, when I suggested we continue chatting back at my flat.

Like many of my friends I came close to developing a drink problem in my twenties, for my part it was mainly a way of dealing with my ‘secret life’. The urge disappeared when I stepped from the closet, and I seldom drank alcohol other than occasionally at parties. Nevertheless I was able to rustle up a bottle of wine at home, which Susan and I began to demolish. In very short order my life story began to spill into the conversation.

“We all thought you were going to have a sex change, you know,” Susan was nursing a glass only a few sips from empty, “did you never think about it?”

“Quite a lot, when I was younger,” I was beginning to slur a little, “but I thought if I wanted to live as a woman, I would have known.”

“But you don’t really live as a man do you?” there was that solemn tone again, “You haven’t raised a family, you don’t obsess about cars or sport, you’re not even that concerned about your career.”

“Well...” I drank back what wine was left in my glass, “you’re smashed.”

“Good point, but think about it,” Susan slumped a little in her chair, “can you call me a taxi?”

“I’ll sleep on the couch,” it took a while for the invitation to sink in.

“Afraid I’ll ravish you in the night?” she broke into a fit of giggles, “I promise to keep my hands to myself, honest.”

“I’ve never slept with a man who offered me a choice of nighties before,” she was swaying quite dramatically, “hey where are you going?”

“Bathroom, I need to get this gloop off my face.”

“Oh God, keep it on you girl,” Susan slumped down on the mattress, “can you help me into this please?”
I awoke to the wholly unfamiliar sensation of being spooned by a woman, and an all too familiar morning erection. My fidgeting woke Susan in stages, her first reaction was to cuddle closer, her second was to run her free hand down my body from breastform to hip.

“Oh it’s you,” she murmured, “I thought I’d turned lesbian for minute there. We didn’t did we?”

“You should be so lucky,” I rolled over to meet her bleary gaze, dislodging her hand in the process and sending it sliding across my abdomen.

“Well hello,” she smiled, “someone’s perky.”

“Don’t flatter yourself”, I sat up slightly to plant a kiss on her forehead, “if you had one too then we might be in business.”

“Honestly sweetie, from what you told me last night, I think you’d be better off without the one you’ve got.”

author's note: bit of a strange one (then so am I, it's uncomfortably autobiographical in places), but I wanted to write something uncertain, and more than a tad different.