Anna's true story

My first memory of transgender fantasies goes back a long way. I must have been around five or six when I showed my mother that I had painted my nails pink with a felt tip pen. She wasn't particularly shocked, as I recall, just told me that only ladies do that. I didn't insist either, it was just a game and I felt no further desire to do it.


However, not much later, maybe when I was six, I became fascinated by the idea of wearing panties. Since I did not have access to any panties, I used plastic carrier bags to make my own panties and wore them under my normal clothes for a while, it was not a very comfortable kind of clothing, and I soon stopped.


I remember clearly that I was seven years old, when I started having fantasies of life-style bondage. I fantasized I was forced to wear only girls' clothes and serve a man. There was no sexuality involved, not surprisingly, since I had no idea about what sexuality was. But I remember the exhilaration of the idea of having to wear girls'  clothes, in particular feminine underwear (I would only be allowed to put on a skirt as a special reward, otherwise it would be only pantyhose and lingerie). My chores would be to wait on my master, serving tea or snacks, holding his newspaper for him while he read it, and so forth. The important point for me then was clearly the idea of humiliation. I am fairly sure that the idea of being tied up was also involved, although I do not remember the details.


I cannot for the life of me imagine where such fantasies could possibly come from. I had never seen any bondage magazines, I had never even seen any porno magazines at all. I had never heard about any of this, and needless to say, my family was quite normal in every sense of the word, and it cannot have come from there. It is as if I already felt that there were three gender roles in nature, female, male, and effeminate submissive, and I felt I belonged to the third category. Or was the submission a way for my subconscious to avoid the responsibility of feeling that I would prefer to be a girl? There is no way of knowing, but perhaps the new generation, growing up in a more tolerant gender-fluid society, will be a test case. If submission is simply a pshychological defence mechanism, it should not be part of the fantasies of our successors in the skirts of the future. Time will tell.


Did I ever start accepting femininity as part of my role model? Perhaps for a while. At Catholic school (a boys only school) we had to sing in the church choir and serve as helpers at Mass. This was just a chore. However, wearing the church cassock was a great thrill for me, since it felt like wearing a dress. And it implied wearing a dress in public, in fact in front of the altar, for the whole congregation, including my family, to see. I think there here I felt some of the innocent excitement that a girl might feel when appearing in public in a beautiful dress, being admired by everyone. I looked forward to Mass, every week. I did not want Mass to end, ever. And when it ended, I hung around at church, always being the last to remove the cassock. I also volunteered to help out at evening Mass. I am sure my parents wondered quite a bit about my sudden upsurge of Christian piety!


Otherwise, I was extremely embarassed about the idea of wearing anything effeminate in public. I have never ever worn a kilt (for Scotland this is very unusual, given that the kilt is a common item of clothing at many official occasions). Ironically, I have often, in private, worn skirts which look like kilts (I just LOVE pleated skirts!). But never a kilt in public.


When I was about nine or ten, I would lie in my bed, wrapping the sheet around my legs, and imagining that it was a tight, long dress. I had a stash of old movie magazines with pictures of beautiful filmstars in evening gowns, and I would imagine myself as one of them. I used to fall asleep dreaming that my body would change over night, that I would be a girl instead. I willed my body to become slender and feminine, imagining each limb, each muscle and each square inch of my skin slowly metamorphosing into Claudette Colbert, Ginger Rogers or Barbara Stanwyck. Again, sexuality was not involved, since I had no idea what sexuality was.


When I was approaching puberty, I fell in love the first time. She was in my class in primary school, a pretty young thing, not very striking, perhaps, but with a nice smile, and a bit shy. But what first drew my attention to her was not her smile. It was the pleated green skirt she used to wear. Somehow, that fascinated me. And I recall one day when the girls had gone to the Physical Education class and left their clothes is the classrom, her skirt was hanging over her chair. I was spellbound, looking at it, imagining that I would put it on as a way of showing her what I felt. Of course, I did nothing. And nothing came of us either. I left primary school with just a vague memory of her. But since then, every time I have fallen in love with a girl, it is always her skirt that has first drawn my attention to her. Every single time. My interest in how a girl wore her skirt became projected onto a romantic interest for the girl herself. This probably has its roots in this first encounter.


However, something in me was changing. That summer, the year I was twelve, was the occasion when it all started.  One day I went past the laundry basket and saw my mother's pantyhose lying there. Suddenly, on impulse, I decided to try them on. I quickly took off my male clothes and pulled the pantyhose up my legs. I stood there, for a brief moment, electrified by the feeling of femininity, my heart pounding and the blood rushing in my ears. The skin of my thighs was tingling with exhilaration, and I noticed a twitching feeling starting between my legs. I could not control myself, and started mincing about in the laundry, breathing heavily, when suddenly I exploded into the first orgasm in my life. At first, I had no idea what was happening to me, nor did I care. I just knew that I wanted to wear these pantyhose, now and forever and ever.


This was the first step. I repeated it regularly, becoming bolder and bolder as time progressed. I would take calculated risks, walking in the garden wearing only pantyhose from the waist down, feeling the wind on my legs. I took to wearing pantyhose in bed while I was sleeping, dreading to be found out, but secretly longing to be found out. I started rifling through old clothes in the wardrobe, and found a lovely summer dress that my mother must have had during her youth. It had a tight bodice (not really tight for a twelve or thirteen-year old) and a full wide knee-length skirt, held out by a taffeta petticoat. It was white with a delicate flower pattern in blue, and with lined with blue ribbons. It was simply divine! I fell in love with that dress. I would have given my life to spend the rest of my days wearing that dress!


I would go out in the evenings into the garden, or take a walk in the fields near the house, wearing the dress over white pantyhose. It was like a romantic midnight walk with my lover. I relished the feel of femininity, the cool wind caressing my thighs and the fluttering of the dress against my legs. I was happy, completely and utterly happy! I sometimes walked around for more than an hour, or two hours, and if the house was dark when I came home, I would go straight to my room, wearing the dress, and lie down on my bed, wearing the dress, without even trying to cover myself with a blanket. I lay there, waiting for sleep to come over me, imagining that I would be woken by my mother in the morning, and confronted. It was not even a calculated risk: it was sheer madness. I longed to be caught and confronted. It would give me the opportunity to perhaps live out my dream openly. I did not have the courage to grasp the initiative of confessing, but thought that if I could only manouevre myself into a situation where I could not avoid being caught, I would not need the courage. As I lay there, waiting for sleep, I rehearsed in my mind what I would say when I was found out. Phrases like "Honesty is the best policy" came to my mind, or "I am sorry, but this is what I am really like", or "I have lived this dream for years, and have realized I cannot live without it".


But I was never found out. Once, my fate was almost upon me. My mother was coming to wake me up, she called my name through the door, and I saw the handle turning. She was coming! I closed my eyes and waited for my fate. Then, before the door opened, the handle turned back again, and I heard her saying to my father that "perhaps it is too early to wake him up, it is only eight o'clock". My enormous relief was mixed with a deep, bitter disappointment. I almost wept. I had so hoped that the hours of secrecy were over. But they were not, and I was never found out. More's the pity.


But that dress became a special friend: late evenings would see me wandering through the garden, or through woodlands close to my home, being a girl for myself and for the summer evening. I learned to associate the smell of summer night with the swishing of cotton fabric against pantyhose, with the caress of the evening breeze against my legs. The evenings were really too cold for wearing a dress like that, but I was not going to cover it up with a jacket. I would rather walk around shivering, not knowing whether it was the result of the cold or of the exhilaration of my thumping heart.


I took to retiring to bed early, to my parents' amazement. I would lie in bed, en femme, reading classical literature (in particular Jane Austen and Emily Brontë). Most of the classical literature I have read stems from this period. So does, in part, my world view. I became rather conservative in taste and manners.


When possible, I would at least try to wear feminine lingerie and pantyhose under my male clothing. But it was not always possible, for practical reasons. But I discovered a new approach. If I had to wear male clothing, I would at least not try to "pass" as a male. I determined to see myself as a girl cross-dressing as a boy. I started adapting my behaviour, became gentler in my manners and tried to cultivate a softer voice (before my voice broke this was easier). I adopted a few feminine mannerisms, never so much that my parents would notice it explicitly, but enough to give a general air of effeminacy. This way of confonting my situation really empowered me, I felt much better than I had previously. It earned me some ragging in school, though, although in all honesty, I was never seriously bullied. (I suspect that most of the potentials bullies subconsciously read me well enough to understand that to bully me would have been almost like bullying a girl, which in the "Age of Chivalry", back in the 20th century, would have been completely unthinkable, at least in Scotland. For instance, it is significant that nobody ever picked a fight with me, which was also quite unusual.).


In school I spent a lot of time with the girls. I never had any close friends among the boys (the way boys socialized was generally standing in groups and competing in toughness and masculinity when it came to behaviour, often resorting to violence to establish their pecking order). It was amazingly boring and silly, and I could never have been a success at that anyway. So after a few failed attempts I quickly decided enough was enough, and starting being with the girls instead. Girls are nice. They were generally more friendly and sociable, and they actually appreciated that a boy wanted to spend time with them. So I was more or less OK as a hangaround, and very few, if any, realized that I really was a wannabe. (One girl in my class did, I think, and she teased me quite a bit, but I of course denied everything, coward that I was. If I met her today, I'd tell her that she was right all along.)


Interestingly, being with the girls was not taken as a sign of being feminine at school. Rather, I was viewed as rather mature and civilized. After all, this was the age when the boys were making their first fumbling attempts at getting to know girls, and I was already there before them, in the midst of the fray. I discovered that I could easily protect my reputation at school by refocusing my interest on the girls in a new light. I would select one young lady as the center of my attention and flirt with her, hiding my more general effeminacy behind a veneer of romantic interest. And this was not lying. After all, I was seriously, and honestly, in love with one or another of them.  My experience from Jane Austen and Goethe certainly helped me to express what I felt to the lady of my choice.


It was a partial success. I was never, ever, seriously considered as a potential boyfriend. But I was accepted in the group, and was given privileges which in retrospect completely amaze me. One of the prettiest girls in the group, the object of my attentions for about a year, completely rejected me as a boyfriend. But she did allow me to stand beside her when she was sitting in her favourite position on the window sill, with my hand on the calf of her stockinged leg. I would spend every recess in her company, being her special friend and attendant, with my hand on her leg. I don't know if I ever found out who she finally selected as her boyfriend, nor do I care, since I am sure that I got much more quality time with her than any of her first boyfriends.


I could not ask for more. I relished the role I had been given. I was always very gentle and soft-spoken with her and her friends. Never noticeably effeminate, but rather gentle in an androgynous kind of way. I never tried to misuse the privilege by allowing my hand to up towards her knee, or my actively caressing her leg, I just took this opportunity of silently expressing my devotion. She must have been very flattered, I suppose. But I was simply grateful. I still see every contour of her leg in my mind's eye, draped in a fairly tight knee-length navy skirt, and below that, a stretch of black stockinged leg ending in a high-heeled shoe. And my hand, resting gently on the instep of her foot.


I often heard, "You are different", and it was said appreciatively. Girls didn't find me interesting as a boyfriend, since I was not masculine, but they did trust me, and like me. But my experiences from school were making me more and more interested in having a straight relationship with a girl. I didn't stop dressing, but it became less important to me for a while. I projected my interest in femininity onto romantic interest in a single girl. On the surface, I became a fairly ordinary boy (or so I thought).


So when I moved to a larger town for senior high school, one might imagine I might have had a chance to live out my dreams. But the higher work load, and my newly found role as a young male hunting for a girlfriend led to my trying to lead a straight life. After all, life IS much easier if you are straight. So perhaps my transgender history was just my crooked path to a normal straight adulthood, or so I thought. I became more masculine in my manners, and stopped wearing dresses. I never wore pantyhose to school. I discovered that I could keep my feminine desires suppressed by masturbating often, so I did that as much as possible, trying to ignore the fact that my recurring fantasies, at the moment of climax, were not of a beautiful woman, but of me in a beautiful dress. After orgasm I could be tough and manly, and imagined I was slowly but surely getting cured. In other words, a couple of years totally wasted, while testosterone was slowly but surely irreversibly destroying what could have been Anna.


But transgenderism has no cure. A beautiful May day came, the smell of apple blossom and rowan blossom filled the air, and Anna was back, with a vengeance. I got hold of a dress, spent most of the afternoons in my room, en femme. I did my homework en femme, and wrote down my innermost thoughts in a notebook I called "Diary of a pantywaist". I glorified in the return of my feminine self. I was euphoric! I wrote pages and pages of self-confession, promising myself not to abandon my feminine persona, promising to to be honest about who I am. I wrote page after page of girlish gushings into my diary, which I then promptly burned in a masculinity-driven purge. I wanted to be cured. But there is no cure.


Then came university. This was, as far as I was concerned, the last chance for me to make my choice. A young adult, in a new environment, with good marks and a secure background, and in a university which considers itself enlightened and modern. I could have joined a support group (there is one now, and there probably was one then, too). I could have gathered the time and the energy and the courage to dress up properly, convincingly, and try to go out as a girl. I might have been read, but I would not have been hurt by anyone, I am sure of that. In fact, since I was not at all masculine in my physique, I might even have presented convincingly as a girl. I could even have tested the possibility of living full-time as a girl, and aiming for transition. The world was open to me.


But I did not take my chance. I did not want my parents to feel disappointed. I took the easy path out. Life is easier if you are straight, and I wanted an easy life. I tried to masculinize myself as much as possible, went out drinking with the lads, and almost came out as the result of a drunken conversation!


What happened was this: Someone was describing a fancy dress party he had attended, and mentioned that a whole group of guys arrived dressed as girls, wearing dresses. He laughed. And I took a deep gulp from my whisky, and blurted out: "Perhaps I should have been there too, to show them how to wear a dress." No reaction. The conversation continued. Perhaps my voice had been a bit too quiet. I took another gulp of whisky, and said, in a louder voice: "Perhaps I should have taken part, to show them how to wear a dress." Still no reaction. The conversation pointedly went off in another direction. They had heard, all right. But out of respect for me, or consideration, or kindness, they pretended that they had not heard it. They wanted to spare me the shame of realizing when I became sober what I had confessed when I was drunk.


Oh, misguided kindness and consideration! Of course I would have been ashamed. I would have been mortified. They were right there. But it might have been the break I needed to start turning my life in the right direction. I would have had nothing more to lose, and could start building up a new, open, honest life as Anna. (My message to you, dear readers, is: Do not assume that just because someone confesses something in a fit of Dutch courage, s/he wants you to forget it. It might be her/his only way of daring to come out.)


I am in no position to complain about their misguided kindness, though. I am fairly sure that I have my own history of fatally missing a cue. I am not entirely sure, but the more I think about it, the more convinced I become that I had the future of Anna in my hands, and let go of her once again. It was at a time when I was in a clear Anna phase again, spending most evenings en femme. I also used to go out as Anna late at night, walking through parks in the city where the lights were not strong enough for me to be read. And I was constantly underdressed 24/7, with at the very least panties and pantyhose underneath my trousers, regardless of whether I was a seminars, or classes, or going out with friends. Not only underdressed, I took to taking slightly greater risks: I also tucked back by male member between my legs, fastening it with tape to get a completely flat crotch. This was natural when I was en femme, but I wanted to at least display this level of effeminacy when I was wearing male clothing. It was visible if you looked for it, but hardly something that others would be commenting on.


It all happened when I was taking an advanced course at the university, and there was an exchange student in the same class, a guy a couple of years older than myself. We used to meet regularly to do our homework together. We both found the cooperation useful, and it was really fun when we managed to solve really complex problems satisfactorily. And one evening, when we had been struggling with a particular hard problem, and had solved it, he reached over and patted me on the thigh, or rather ran his hand up and down over my thigh. It was a simple gesture of solidarity, of celebrating that we had succeeded with our task. But the sound was unmistakable: he must have heard the pantyhose rubbing against the trousers, he must have felt the soft elasticity of my thigh encased the pantyhose. And why my thigh? Why not my shoulder or my arm? We had been sitting side by side for a couple of hours, so my guess is that he must also have noticed that my crotch was flat, and begun suspecting already beforehand that I was deliberately suppressing my masculinity.


So he rubbed my thigh. And I was so nonplussed that I laughed, and then he laughed, and it was a shared fun gesture, and we remained friends and co-students and everything was fine. Except that I have been wondering. What would have happened if I had reacted otherwise? How would I have reacted today? Given my understanding of myself today, I can easily imagine a more honest, and more beautiful, scenario. Something like this:


Bill (let's call him Bill) reaches over and rubs my thigh. With a sudden intake of breath (to make sure he notices), I close my eyes and start breathing calmly, leaning back my head, exhaling softly and quietly through pursed lips, perhaps with a slight trembling. Now two alternatives open up:


In scenario one, either Bill stops and removes his hand, because it was not his intention to make a pass at me, but even so he has clearly read me. I could of course make the situation clearer by saying in a pleading voice "Don't stop!". Now, whatever happens, I am outed. He can hardly ignore what has happened, and given that we were fairly good friends, I am sure that he would have asked me about it, and I would have told him honestly about myself. I would have come out, and he might even have been able to live with continuing with our homework routines, but with me en femme. Or not. But even so, the secrecy would be over. Anna would have come out.


In scenario two, Bill doesn't stop. Once his intentions are clear, perhaps I tell him "Bill, there is something about me that you should know", and I go out to the wardrobe and come back entirely en femme. And the rest would have been history. I can envisage all kinds of endings to this scenario, some of which involve full transition to be Bill's wife, others which at least involve living full-time as Anna. At the very least, it would have been a completely new, but logical, step for Anna to take. I see myself offering myself to Bill as a love gift. I am deliberately vague here for two reasons. One reason is that I am visualizing the symbolic act in itself, not any specific action by which it is manifested. I have no idea what such an action might have been. Or rather, I have a few ideas, but I do not feel it would be appropriate to be explicit about them, which is the second reason. So therefore, please just accept the rather corny description I have given, and use your imagination, if you must!

Strangely, I never stop to reflect whether I would have been physically attracted to him. I wasn't at the time, he was just a good friend. But I feel inside me that that would not have mattered so much. Attraction is a complicated thing (I will try to write about this elsewhere on this website), and his desire for me would quite conceivably have served the purpose of awakening my desire for him, or at least my desire for being his girlfriend. I do not know, and now I will never know.


If only I had had the presence of mind to let these alternatives course though my head and and taken that sharp intake of breath within the first few seconds of our moment! But I laughed, and he laughed, and the moment passed, and I have spent hours and hours during the past couple of decades wondering what might have happened!


Instead, I met a girl, and decided to become a normal man. We became lovers, and I thought this would cure me. But there is no cure for transgenderism, so after a while, Anna came back. I confessed to my girlfriend, and she agreed to meet Anna. What ensued still fills me with shame. I don't know what she expected, but it was all still so much of a fetish for me that what I did was simply dress up in her clothes and masturbate. And immrediately afterwards, Heaven forgive me, I went into remorse and self-disgust mode. Not suprisingly, she was quite disappointed, and did not want to have anything more to do with Anna. Can anyone blame her? I had claimed the need to express my "inner femininity" (i.e. in essence to be as like her as possible), and then simply expressed it by masturbating in a skirt, and afterwards being disgusted about my femme appearance (i.e. by the fact that I had been "like her"). In other words, it was a direct slur against her gender. I still burn with shame at the thought of how horribly offensive my behaviour was. If I could, I would today offer her my sincerest apologies, but that is all water under the bridge. Amazingly, she did agree to a "don't ask don't tell" policy which gave me the freedom to be Anna when she was not around.


Our relationship did not last so long. It did not have so much to do with my dressing habits, but rather with the fact that I did not feel masculine enough to be a good lover. I did try, but it was nothing that came naturally for me. In role play, I could be quite imaginative, but in taking the male role as expected of me by a woman, well, it just wasn't really what I was cut out for. Other problems ensued, and we went our separate ways.


Not long after, I met another girl. We became very good and close friends and enjoyed each other's company as two good friends would, with no idea of romance. However, the closer we got as friends, the closer we discovered that we were getting emotionally, and soon we were head over heels in love. This was the real thing! I was going to be cured! I wanted to be honest to her, and confessed everything to her, and she was horrified. I promised that I would stop, that I would be cured. And for a couple of years, it did work. We got married. I became a real man, adopted masculine manners and tried to forget. But there is no cure for transgenderism. So when the need returned, I did not want to hurt my wife, so I hid my needs, drowning them in other activities. Working overtime. Smoking too much. And dressing in the closet. And regretting past opportunities. I dearly love my wife, we have good times together, we have many shared interests and have a very good relationship. But the same problem remains, that I am not masculine enough to really be a good husband. If I could use drugs, surgery, anything, just to become a real masculine man for her, and forget about Anna, I would, without a moment's hesitation. But regardless of all the other debates about what causes transgenderism and what it really is, there is one thing that all the pundits are painfully unanimous about. There Is No Cure. No Cure. None at all.


For me, the opportunity to be Anna in real life is gone for good. I am old and ugly now, my physique irreversibly poisoned by testosterone, and I could no longer hope to become pretty, no matter what wonder hormones came my way. I can only dream of another possible life, where I could have taken different steps and gone in a totally different direction. I might just as well resign myself to being a man. But the thought leaves me with a feeling of sadness.

Coming out as Anna would simply reveal a man in drag, and would not show that my femininity is on the inside. So I am trying a new strategy. Yes, I am living a fully male life. But at work, I am often underdresed (i.e. wearing female underwear under male clothing). I also tuck in (any transvestite understands what that means, you others just check the literature!). This implies that my crotch is always flat, even with male trousers. I don't know if this is noticeable. It requires that someone actually look directly at my crotch, which is not all that likely. And even if they do, they can hardly comment "Excuse me, Peter, I notice you have a completely flat crotch. Don't you have a penis?". I don't see this conversation in the near future, somehow. It is a risk I am willing to take.

More importantly, I consistently try to speak with a soft, gentle, slightly effeminate voice. I am slowly adopting feminine manners. I try to gradually but consistently ease myself into a role where being feminine is normal, or accepted. I hope to be able to send a subliminal message "I am not masculine, so don't treat me as such", while not being so overt that my colleagues find it disturbing. So rather than coming out in women's clothes, and not passing, I allow my inner girl to instead cross-dress as a man 24/7, without not fully passing as a male. This is more natural for me, and more honest, too. Somehow, I believe that this can make Anna more convincing and easier for others to accept (and more difficult to confront directly). Since I am generally liked at work, because I tend to be helpful, cheerful and empathetic (and trying my best to improve in this respect), I also hope it will help to send to people around me a signal that effeminacy is a good thing. So if you think of me as a man in a skirt, there is a lot less man and a lot less skirt than you might imagine!

This is the road I will take. This will be my contribution to Anna and to the transgender community. If I can help to make the world a softer and gentler place, Anna will have done her bit. I will document my inner development on these pages (a diary of mental transition, if you like). So, although I would have made a different choice in retrospect, I am not bitter. I am at peace.

Physically. it is too late for me, dear reader. But you may belong to a new generation where tolerance is the order of the day. If that is what you desire, don't miss your chance! Don't wait until you are too old to be pretty! Release your Annas, and Marys, and Carolines, for the world to see! It will make the world a more beautiful place for us all!