A little bit about me


Thank you for visiting my site. I’m not really called Mrs Benn – my name is Karen Smith, and I live in the city of Sheffield in South Yorkshire in England. This site has to do with being transgendered, and this is the story of my journey from a confused boy, who used to wear his Mum’s clothes and play with his sister’s dolls, to a slightly less confused adult.

There are some moments that mark our lives; like milestones or triangulation points: my wedding day, the births of my children, and July 11, 2012. Stepping out of the hotel into the light drizzle of a Manchester evening, reaching into my handbag for an umbrella and walking first up to Piccadilly station and then down towards Piccadilly Gardens in a skirt and ballerina pumps (and a waterproof mac; this was summer in Manchester after all!), out in the wide world for the first time. I thought I might feel afraid, or nervous, but there was a curious serenity, a feeling that my whole life had led to now and this was somehow meant to be; the sense of something long hoped-for that might never have come to be realized and made concrete at last; something yearned for and yet always in jeopardy: I was me.


For somebody born female it would be an utterly unremarkable occasion but for a genetic male in his mid-forties, this public manifestation of another, feminine persona was momentous. I was nervous as I stepped into the corridor from my hotel room and, as I rounded the corner to the lifts, my heart missed a beat as I heard the lift stop and the voices of young men; a group of burly blokes in high spirits emerged through its doors but to my relief they simply walked on past without paying me the slightest bit of attention. It was as if they didn’t notice I was there. My first port of call was Debenhams; in I trotted, and took the escalators to the first floor to look at Ladieswear. I saw a dress that I liked, and held it up to myself in front of the mirror to get an idea of the length. Nobody noticed! Of course it’s a perfectly natural thing for a woman to do, but to somebody who has always had to judge the length of a dress entirely surreptitiously, by estimation, past experience, trial and error, to do something so simple was wonderful. My overwhelming experience of the whole evening was one of simply passing unremarked, of blending in.

You’d have to be transgendered, of course, to appreciate how not being noticed would be a triumph, or how a stroll around the shops that was entirely uneventful could be the cause for elation. On my way back I stopped at the Co-op to buy a bottle of water. This necessitated my first conversational encounter en femme; I had to fish my purse out of my handbag with trembling fingers, find the money, pay and say thank you. I realized in a panic that my voice was very much a work in progress. I’d practiced softening it a little, but I was very under-prepared. I just spoke softly and did my best. Nobody seemed to notice.

There was one moment of recognition, near Piccadilly Station, as I walked back to the hotel. Two lads looked long and hard at me as we approached each other. Frankly, they looked far longer and harder than good manners really allowed! As they passed, I heard one of them say to the other, “That was a bloke!” Of course, if they had to look that long and hard, and get that close to read me, then I probably wasn’t doing too badly.


But more importantly, and to my astonishment, I realised that I didn’t feel the slightest bit of shame or embarrassment at having been read; I simply didn’t care. I am a bloke, whatever I might be wearing and however carefully my make-up has been applied. I am a transvestite. I used to hate the word, it sounds like a disease. But it’s just an adjective; it’s what I am. I’m a man and I like wearing ladies’ clothes. No, it’s not that I like doing it; it’s that I have to do it, that my identity is somehow tangled up with this way of self-presentation that has been, for the past four decades, an urge that has been largely suppressed. ‘Transvestite’, to me, represented a whole world of sensations, feelings and modes of expression that for so many years have been hidden, a source of embarrassment, secrecy and self-reproach. Finally, in my forties, I have come to terms with what I am. I am a transvestite, not as a lifestyle choice, but simply because it is what I am.

Strictly speaking, Karen first stepped out into the wide world at Leeds First Friday (LFF) at the start of May, 2012, a few days before her 47th birthday. Why it took her so long to emerge from her closet is of course a complicated tale. For a week beforehand, sleep came only with a struggle. I can’t remember being so excited about Christmas as a child. Eventually, I stood in front of the mirror in my hotel room, ready to step out into the corridor, not entirely sure what to expect. I remember walking down the stairs at the hotel in heels, and going into the bar to buy a drink; I remember cold air on my legs, the breeze up my skirt, cobblestones under my heels. LFF is a lot of fun. But stepping out onto the streets of Manchester felt like a more significant beginning, because I was walking away from safety, from a crowd of other folk like me, and into the rest of society and I had no idea what they would make of me. For me, transvestitism is not about partying, or posh frocks but about identity. I have found that being out and about among ordinary folk doing ordinary things is what really connects all the shattered pieces of my self; then I can feel, even if only for a day, that I am whole, that it is OK to be me.

The beginning

Like most transgendered folk, the roots of the way I am go back deep into pre-pubescent years. I can’t say exactly when it all began. I was always different as a child. I was a bit of a softy, happier doing handicrafts than playing football, and mystified by the competitiveness and aggression of other boys. I had Action Men and built Airfix models like other boys, but I was always at the periphery of the male world. A few things do stand out. I remember being sat with my class on the carpet at school when I was ten. My teacher wanted me to do something (I can’t remember what). So she asked me, “Karen, would you…” It was a simple slip; there were several Karens in my class. I should have been surprised, put out, but instead I remember thinking how lovely it was to be called by a girl’s name. Of course everybody laughed, and so did I, and there was a little embarrassment, but mainly a feeling that it was lovely to be treated like a girl, even in a trivial way. Years later, when I started interacting with other transgendered people over the internet and needed a feminine name, Karen was an obvious choice because the memory made such a strong impression.

I remember dreams about being dressed as a girl as I approached puberty; I remember waking up with vivid afterimages in my mind, and being disturbed by both the intensity of the memories and the growing sense that I wasn’t “supposed” to feel such intense pleasure at being feminised. As puberty set in, and my developing body began to differentiate itself as masculine, my conscious thoughts began to be flooded with urges to cross-dress, and whenever I was home alone I began to experience the urge to borrow items from my mother, or sister, and experience an hour or two of feminine bliss, before later being wracked with self-reproach for my peculiarity. In those days there was no internet, and the only sources of information were books, magazines and TV. The only transvestite regularly on our TV screens was Dick Emery; as far as I was aware, there was nobody else in the world who had this peculiar desire to dress as a member of the opposite sex. Although I can’t remember talking about transvestitism with anybody, Dick Emery’s cross-dressing personas were the butt of humour, and in adolescence, young people are keenly aware of gender distinctions. While I did not understand my urges, it was clear that they were peculiar and reprehensible – at least to society at large. But try as I might, I could not stop myself and if anything, the urges grew more intense. I remember, at the age of eighteen, my parents going on holiday with my siblings and leaving me at home alone. I had a job for the summer, and spent a substantial part of a week’s pay on lingerie in Marks and Spencer before going home, shaving off all my body hair, and then getting dressed. My sister had a couple of beautiful floral cotton dresses from Laura Ashley, bought for weddings; I picked one in pink and blue, and remember standing in front of the mirror feeling like a perfect princess.


Just as I began to develop a more determined sense of self-expression however, I also began to wrestle with the sense that it was deeply peculiar to do this. In the 1980s, our world was much less liberal than it is now. In my teens, I had no knowledge of anybody else who experienced these peculiar urges. I became determined to cure myself. By twenty-one, I felt the job was done, and all urges to cross-dress were firmly consigned to history. The following year I fell madly in love, and two years later was married. If I had thought about cross-dressing at that time, which I didn’t, it would have been merely that it was an embarrassing developmental phase of adolescence that was firmly in the past.


It was a terrible shock when the urge to cross-dress emerged again two years into married life. With the benefit of hindsight, of course, it is clear that I was being hopelessly naïve to expect that something that had been with me – consciously at least – since before puberty could be so quickly dispatched. What is perhaps very hard to imagine, if you are not transgendered, is the adeptness that an adolescent transvestite develops for self-deception. Each time he is home alone, and the urge to dress sweeps over him, there immediately follows, as the borrowed items are returned with meticulous care to their places (he quickly becomes agile at covering his tracks, for a fear of discovery develops early), a sense of stinging self-reproach and a firm decision that this will be the very last time. Time and time again the same ritual repeats itself. The urge is hopelessly overwhelming, and yet afterwards, the transvestite tells himself with complete confidence that this is the very last time. A deep-rooted capacity for self-delusion develops. Not surprising, perhaps, that after several years without any dressing or, indeed, any urge to dress, one might actually begin to believe the habit broken.

But two years into married life, its reappearance was a crushing blow. There followed two decades of awful turmoil. For the vast majority of the time, I managed successfully to exclude all thoughts of dressing from my mind. Significant amounts of time would be spent wrestling the urge, and resisting. But inevitably I would succumb and the relapse would be followed immediately by self-loathing. Now I had a wife, a woman who I loved dearly, around whom my whole life revolved. Each time I fell, I had a guilty secret from her. My self-loathing was not just for succumbing to my disgusting weakness; it was for secretly doing something that I did not want to share with the person closest to me. Why not tell her, speak to her about it? I do not know what would have happened if I had done, but the thought seemed incongruous. Not only was cross-dressing bound up with feelings of deep self-reproach, it was also at odds with the person I had become. The softy at primary school moved on to a very tough comprehensive school; with determination, he got stuck into sport, and began to learn to survive a masculine world and, indeed, to do well in it. Whether the adaptation was a positive one, in the long-run, I am not sure. However, by the time I reached university, I was strong, self-sufficient and generally able to look after myself. A few years post graduation, I could pull off a pretty convincing impression of an alpha male.

Accepting Myself


In my mid thirties I had an extended period (several months) during which I kept a secret stash of female clothes and my first pair of falsies. I kept them in a suitcase in a secret place, and I think they were quite unlikely ever to be discovered. During that time I practised hard with make-up, and being able to work at home regularly, was often able to spend half a day en femme at home. Being able to dress more completely and at leisure I was able to reflect for the first time in a more considered way about what it meant to me. Having leisure to dress, and apply make-up carefully, I was more aware of the sensations provoked by being dressed, and much less focussed on the need to quickly satisfy a need to dress and get cleared away before being discovered.

I had always assumed that my cross-dressing was a sexual fetish of some sort. What astonished me now was that I could spend hours dressed and fully made-up without the faintest glimmer of any kind of sexual arousal. In ‘The Lamb Lies Down on Broadway’ Peter Gabriel sings, “I’ve got sunshine in my stomach, like I just rocked my baby to sleep.” That sunshine in my stomach was the overwhelming effect of being dressed: a sense of deep inner peace. It appeared not to be sexual at all. Being dressed brought a kind of serenity, a sense that everything was right with the world.

At the time, this realisation was a shocking one, because the logical consequence seemed to be that I was transgendered in some way. This led to a purge of all my feminine things, after some six months of building up a substantial collection. I couldn’t deal with the prospect of being transgendered; it was much easier, psychologically, to write myself off as a pervert. For a further eight years I waged the same awful, futile war with myself. There would be lengthy periods where I didn’t think about dressing and then one day I’d see something in a display in a clothes shop and unbidden the thought, That would look nice on me, would burst into my conscious. I would tell myself firmly, I’m not a transvestite, but the tension would build, often over a long period in the face of sustained efforts to resist, but eventually there would be a trip to the shops, the delicious experience of browsing for clothes, the release of mental tension and then almost instantaneously the rush of guilt.

By my mid-forties I began to realise that I was not going to change. I had been searching the internet for advice, information and encouragement. It was clear that I was stuck in a vicious circle familiar to many others. Slowly, I began to open myself to the possibility that I was a transvestite, and that it was not a perversion, nor even a cause for self-reproach, but simply an aspect – however unusual in our society – of my person. On reflection I realised that when dressed, I never felt guilty or ashamed of being dressed. It never felt dirty or wrong. I feared the consequences of being discovered – the condemnation and approbation of family and colleagues – but being dressed itself simply brought me sunshine in my stomach. I began to try to countenance the possibility that the notion of “gender” was blurred for some people and I was one of those. I had no desire to switch genders permanently, but I had an urge, a need, to be able to express myself, to present myself to the world in a non-masculine way. I began slowly, but surely to accept that being a tranny was not something I had chosen, but something I was.

Telling My Wife

But now I had a moral dilemma of major proportions. Could I accept myself, and countenance expression of my transgenderism, even on an occasional basis, as a normal state of affairs without telling my wife? I think that the idea of secretly keeping a frock tucked away somewhere – of hiding something from my wife – was the most difficult aspect of this throughout the previous two decades. But in the past I always told myself, as the items were disposed of, that this was the last time. As it would upset her to know, and I was never going to do it again, I didn’t need to say anything. To accept my feminine self in perpetuity meant either talking to my wife about things, or keeping a permanent secret. After some months of heart searching, I decided to tell all.


I could write at great length about the consequences of that decision, but I will not. I think that morally speaking it was the right thing to do, but I cannot in all honesty claim that it has made my life a happier one. There are some women who are able to accept their partner’s cross-dressing, but my wife was not one of them. For a few weeks after I told all, we were closer than ever, because I think she realised how difficult it was for me to open up to her about the subject and because she realised I had bared all to her. But quickly, other factors took over. Our marriage was an up and down experience in the following eighteen months. We have children, and both of us take our commitments very seriously. I do not think we were likely to separate. But we became distant and that pained me greatly. In the last few years, the situation has improved – we are close again, and the hard work that both of us has invested in repairing our relationship has paid off.

However, my wife still finds my cross-dressing repellent. She knows very little about it, and has never seen me dressed. She cannot bear even to see an item of Karen’s clothing. She has accepted that I need to go out. But this side of my life is something that she wishes to know nothing about. Since telling all, I have discovered that I have a desperate desire to be known and accepted by my wife as Karen. It is something that is highly unlikely to happen, but pathetically, I hope against hope that one day I may no longer repel her and that she may even be able to love Karen – not sexually, but accepting her as part of me. Karen is a deeper part of me than I realised; she is bound up with a great deal of what people think is best in me, and rejection of her feels like a rejection of me. I imagined that years of hiding my urges would make it easy for Karen to live out of the way, but now the closet has begun to open, if only a little, she wants to be known and loved by the person she loves most. To be spurned by her is the source of deep pain.

Out in the Wide World


At least having told all I am at liberty to express myself, to feel that blissful sense of wholeness that I have as Karen, from time to time. And there is nothing I like better than simply trying to blend in, to go about in the world doing normal things. My second outing was on the Saturday morning following my first. I decided to take the tram from Piccadilly to the Lowry gallery. To be candid, I thought mainly about the Lowry, and not too much about the process of getting there. Stepping onto the escalator leading down to the Metro station I realised that there were an awful lot of people travelling by tram that day. The platform was crowded and I squeezed through to join a queue for the ticket machine. Nothing remotely secret about being dressed now, I thought. I was very nervous. Eventually my turn came and I fumbled for my purse, put coins into the machine and turned around to a platform where nobody, apparently, was remotely interested in me. Again, that blissful feeling of simply passing unnoticed!

A few weeks later I had a business trip to Glasgow, and took the opportunity to spend an afternoon wandering round the shops. I realised then how much the excitement of being out for the first time had carried me along in Manchester, because now I felt incredibly nervous. It was as if my conscious brain was beginning to take charge, alerting me to the fact that there was something deeply abnormal about a middle-aged, middle-class man getting dressed like a woman to go and wander around the shops. Once I was out I began to relax, but I knew I needed to challenge myself a little. I had avoided speaking to people where possible when I was in Manchester but I knew that if I was going to get out and about a lot I needed to stop avoiding them. My first port of call was a coffee shop. In some embarrassment I walked up to the counter, smiled as sweetly as possible and asked for an Americano. There was a really lovely girl serving, who smiled and chatted away as the coffee brewed. It was fabulously natural. I collected my coffee, found a sunny seat by a window and drank it in a state of shocked bliss. After shopping, I tried ordering dinner at my hotel. I had a very grumpy waiter. I thought perhaps he took umbrage with my being a tranny, but he was just as miserable during breakfast the next day so I suspect it was his personality. And I managed not to be bothered by it at all. The biggest challenge I experienced (as it was the first few times I ate out) was managing to eat my food without also eating my hair. Practice makes perfect, however…

I have been out many times now. The first few dozen times, there was quite a bit of nervousness; I wondered for a while if the state of nervous tension associated with going out was part of the attraction, subconsciously. However, I’ve now been out so often, that the nerves have more or less disappeared. I’m sure this is not about thrill-seeking. What remains is the wonderful sense of peace that comes from being able to be myself. There may be stress and anxiety because I’m in a strange city, or because it’s been difficult to make the time to dress. Occasionally I will ask myself if it wouldn’t be easier not to bother – to just put my feet up and relax doing something that requires a little less effort. As I start to do my make-up, however, I begin to relax. I always do my make-up first when getting ready to go out because I’m a very messy girl and otherwise there would be translucent powder over all my clothes like snow. The routine is very similar each time and right up until I start putting on my lipstick I keep saying to myself, You look like such a bloke; however are you going to walk the streets like that? And then, in the space of a couple of minutes, the lippy goes on, then the clothes and I’m stood brushing my hair in front of the mirror and a delicious feeling that all is right with the world is sweeping over me.

Karen7Trans-World Adventures

I could write at great length about the various things I’ve done, but I’d probably send you to sleep. There are certain things that stand out. I remember my first trip on a tube train – stepping onto the escalator at St Pancras, and feeling a blast of air lifting my skirt as it began to descend. Visiting places so familiar, so ingrained in my everyday existence, as Karen, is a really special delight.

The next day, I boarded a tube train packed with Arsenal supporters. I have to say that the sight of so many football supporters was a tad disconcerting. Perhaps they were too absorbed with Arsene Wenger’s fate to notice that I was a fake, I don’t know, but they treated me with perfect chivalry, politely shuffling up and allowing me space to stand comfortably when there really wasn’t much space at all.

I used to live in the US, and visit there several times a year on work. A great pleasure for me has been to get out and about in a number of American cities, and even to take a flight en femme from Chicago to Denver. My first American outing was in Philadelphia, shortly after my first outings in Manchester and Glasgow. A few blocks from my hotel I was surprised to discover an overturned car and men in FBI jackets. I was for a moment disconcerted, until I saw cameras and a giant turbine parked down a side road, presumably to create special effects. I milled around with the crowd. A woman caught my arm and said, “Great skirt!” in a very friendly way; I was flattered and a little bashful too, being still quite nervous about conversation en femme. Reminder to self – Americans are interactive! Disappearing quietly into the crowd may be less easy than at home!

Eventually I got to Washington Square. I slipped off my cardi and sat on a bench in my camisole enjoying the sun and watching the water from the fountain catch its light. A guy jogged through the park and didn’t take his eyes off me for pretty much the whole of his route. I was not (and am still not) entirely sure what to infer from this, but I had a good laugh about it afterwards. Maybe he was horrified at the sight of an Amazon on his local park bench. I ended up in a gay bar for a drink and the waitress told me they were recruiting extras on the film set (the movie starred Harrison Ford apparently). I nearly ran back and applied.

None of this is particularly remarkable, from one perspective – not to a genetic woman anyway – but to somebody who is transgendered and out and about in the world for the first time, the rush of new sensations and feelings is overwhelming – a pleasure ride of vast proportions!

Some months later, I visited Singapore. If you wish to blend in, I realised as I walked down Orchard Road, then being over six foot tall and white can be a limitation. But the warm tropical air around my legs felt heavenly. One or two people stared. I remember one older woman standing stock still, literally open-mouthed, as if she had seen an apparition. But even there, most people didn’t seem to notice me. I contacted a few Singaporean transgendered people before going, to see how safe it would be, and to be culturally aware before stepping out. It struck me that whatever faults the UK has, it is predominantly a very liberal place; by contrast, there is a great deal more fear among Singaporean t-girls about their reception in society at large. Wandering into Marks and trying on a bra would be out of the question in Singapore, if what I was told is correct.


By and large, my experiences being out and about in the UK have been astonishingly good. A few years years ago I would never have imagined walking en femme into ladies’ clothes shops, trying things on and chatting to staff in an entirely natural way, or going into restaurants and ordering meals, or any number of things that have become regular parts of Karen’s life. I have had occasional sniggers, and some people do stare, but by and large most people don’t notice and a surprisingly large number of folk I have met in shops and restaurants seem to go out of their way to be friendly. In fact, I’d say I’ve been quite touched at how hard many people have tried to make me feel welcome. Maybe it’s that British love of eccentricity, or just good manners, but it’s been a very heart-warming and entirely unexpected aspect of going out as Karen. I have certainly not had any really bad experiences out and about.

I think that one reason I eventually grasped the nettle and tried going out was the encroaching feeling of mortality I experienced as I reached my middle years. People say that as we approach death we regret not the things we did, but the things we didn’t do. I didn’t want to go to my grave a fractured self; I wanted to try to put the pieces together, to open the cage and let Karen spread her wings. My appetite for being out and about is undiminished, but I can die knowing I had the courage to try to be me, to be true to myself, to my beliefs and to the person closest to me.

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