Maiden Voyage

Note to the reader – this is not a work of fiction. It is the story of how one woman found herself, in spite of the odds, and in spite of being born with a male body. It is entirely autobiographical, sometimes painfully so. But having read many tales of transsexuals, which end up being, in most cases, little more than tales about the cross-dressing fetish, and having been encouraged on numerous occasions to write about my experiences, here it is, to set the record straight. One woman's story of how she found herself, and how, in reality, transsexuality, is not a fetish, but a physical trait – as is brown hair or being straight or gay. I hope you find it enlightening, but above all, I hope you enjoy it. Most of the names have been changed to protect the innocent.

***

Jessica hung up the phone, put her head on her arms on the desk at which she sat, and bawled. All her frustration, all her fears were encapsulated in that moment. She had just spoken to her mom 4,500 miles away to tell her mother that she, Jessica, was a lesbian. Her mother had not taken it well, especially given the fact that, as far as her mother was concerned, she had given birth to a son, not a daughter.

"What do you mean, you're a lesbian? I don't get it. Lesbians are women."

"I know Mom. I am a woman, a transsexual woman, and I like women. So, I'm a lesbian."

"Don't be ridiculous" her mother had retorted. And the conversation deteriorated from there. Jessica and her mother had both ended up in tears, Jessica because she fervently did not want to lose contact with her parents, though she knew it to be a distinct possibility; her mother from utter, unmitigated shock.

As Jessica slowly recovered her composure, her mascara, mixed with her tears, leaving black streaks down her cheeks, her thoughts ran back to what had brought her to this moment.

***

Jessica was born in Slough, a town on the outskirts of London. She was the elder of her parents' two children; her brother, Peter, was born almost eighteen months later. Growing up, Jessica was remarkably unremarkable; just another shy kid, afraid of her own shadow, never quite fitting in, but unremarkable all the same.

Although to the rest of her family she was a boy - she had boy parts, did boyish things, attended cub scouts, played soccer, badly – to her, something just hadn't seemed quite right. Although she was never able pinpoint it, she knew she was different. And she wasn't alone...

Every Sunday after church, Jessica, her parents and her brother, would visit their grandma and granddad. Her grandma clearly saw something in Jessica that the others didn't; she encouraged her grand-daughter to play with her pots and pans, giving the young girl buttons to 'cook' for the family; she had a toy kitchen, and a stove. Once she was done 'cooking' the food, little Jessie played mom, serving up little bowls of buttons to the rest of her family. When it came time to leave, her grandma fussed over Jessica and her beautiful, curly hair, applying hair lotion, brushing it, primping in; Jessie loved it.

Jessie's parents and grandfather tried to discourage her grandmother from encouraging Jessie's 'girly' behavior, saying it just wasn't right. But her grandma would simply smile, asking them, "Where's the harm?" However, Jessie's parents' concerns won out, and by the time she was nine or ten, her grandmother had put the pots, pans, and the toy stove, away for ever.

At home too, Jessie's parents tried to discourage her. Clearly, they just wanted their little boy to be happy and 'normal,' to not be teased or bullied at school; and as far as they knew, they had two sons. But Jessie was simply confused. When she and her mom washed the dishes, for instance, and her mom applied hand cream afterwards, Jessie asked her mom why she did this. "To keep my hands soft. All that hot water would harden up my skin otherwise," explained her mother. Jessie's earnestly asked question, "What about my skin?" was met with gentle laughter from both her mom and dad. They explained that 'boys' don't have soft skin.

By the age of ten, her desire to do girly things, and to play with the rest of the girls, was growing stronger. This was magnified when a new pupil, Helen, arrived at the school.

Helen and her older sister, Sarah, came to the school for maybe a year, in 1975. Jessie and Helen became inseparable during that summer; they would play horses together, skipping, or, in their young minds, trotting and galloping, around the playing field, neighing and what have you. Of course, some of the boys thought this was hilarious, and taunted Jessie mercilessly. She found herself torn between not wanting to be taunted so by the boys, and yet wanting to play with the girls. For the most part, she chose to ignore the taunts, and was in heaven to be free to play with her new playmate and her friends.

Jessie bade Helen a tearful farewell at the school gates at the end of the summer. Helen had explained that her family was moving to Reading, a large town about twenty miles to the west; but, being eleven, it may as well have been at the ends of the earth. On the last day of school at the end of the summer term, Helen's parents drove her and her sister away from the school for the last time. As Jessie waved goodbye, tears running down her cheeks, the two sisters' equally tear-streaked faces looked back at her for the last time from the back seat of their father's car, waving their friend goodbye. Jessie ignored the taunts from one of the boys nearby, and ran home, crying.

As puberty hit, Jessica's male hormones took over, and pushed little Jessie deep into her subconscious. She remained very self conscious about her body in the school changing rooms, however, and about her genitals in particular. She desperately wanted her pubic and facial hair to grow, to somehow prove to those around her, and to herself, that she really was a boy. But it seemed that the more she tried, the less she succeeded. Still deemed a 'sissy' and a 'poof', eventually, she gave up trying, and went in the opposite direction, becoming anti anything that was popular or fashionable. And she became a life-time member of the outsiders' club: that group of students that just doesn't fit in anywhere else, all circles when squares were in, or squares when ovals were now hip.

As part of her self-defense mechanism, she developed the ability of picking up just enough information about soccer to be able to maintain a semblance of respectability during conversation with her male friends, and to give credence to the male façade that she had built up. More often than not, though, when she expressed an opinion about this or that soccer team or player, she was merely repeating someone else's overheard comment.

Her school days passed by eventually without major incident as she did her best simply to get through and to fit in as best she could. In the fullness of time, she started work for a big pharmaceutical and cosmetics-based department store, where she was one of probably a hundred or more employees. Retail, high street retail, at least, is a female dominated industry, and Jessica, now a young woman, though outwardly still male, enjoyed the female company. She found that she could much more readily identify with and be accepted by them.

She had male friends, too, of course, and Jessica met a number of friends at work, including two, Frank and Marc, who would become life-long friends. The world still saw her as a young man, and she was still doing her darnedest to fit in; she enjoyed her friends' company, individually or in groups, and because her group of friends was mixed, so were the groups in which she would typically hang out. But it was becoming more obvious to her that, in general, she just didn't like the company of men, in groups especially, and had little in common with them. The bigger the group, or the more rowdy they were, the less comfortable she was.

One area that bothered her particularly was sex talk. As the male groups she found herself in became rowdier, and often, more drunk, their talk would often turn to the female of the species; openly leering at other women in the bar, making crude comments about what they would do to this or that woman, talking about them as mere objects. Their boasts disgusted Jessica, but more, it bothered her because, while she readily acknowledged being attracted to women, and insanely turned on by the mere thought of a naked female body, the idea of being with a woman terrified her. On the one hand, she didn't know what she was supposed to do with this thing between her legs, even though the merest breath of air was enough to stand it on end like a flagpole; on the other, it seemed all wrong somehow. Her boy parts embarrassed her. Not just because it seemed overly small to her, but also... also what? She still didn't know. Nevertheless, she was anxious to lose her virginity. At 20, she was still a virgin, and this status was becoming like a mill stone around her neck. She had to do something about it, but what?

She dated two or three girls over the course of the next few years, but remained a virgin, and although she fell in love, or at least in infatuation, with each one, none of these relationships led to anything serious or to her resolving her dilemma. And so it was that, shortly before her 24th birthday, she was still a virgin when she met Sonya.

Sonya worked with Jessica and, after talking to each other about music a few times, Jessica found herself invited to the younger woman's home. That night, Jessica entered Sonya's bedroom for the first time, and entered Sonya too, though she was terrified at that first encounter.

Jessica loved the intimacy, and craved the touch, and the actual sex act itself had its appeal. But still, she was terrified, which was not helped by the fact that Sonya was a more experienced lover than she. Jessie found that she was happier sexually when she was flying solo; she couldn't, or found it difficult to perform for or with Sonya. Whereas she'd heard it said that women need to have a reason to have sex, men just needed a place, she found that she didn't fit this mold. Not for the first time, nor for the last, she found herself explaining that she just "wasn't like other guys." Nevertheless, she and Sonya's relationship developed and they were eventually married. Both women had remained at home with their parents until this time; Jessica was 26 when they married.

Married life seemed to suit her well, for the most part. Sonya had a fairly dominant personality while Jessica was meeker, and so, Sonya was the alpha in the relationship, to Jessica's omega. Jessica was more comfortable in the role of the 'wife'; her mom had taught her well, and so she took on a number of the stereotypically wifely chores. She enjoyed cooking and laundering especially.

This arrangement extended to the bedroom. Jessica's discomfort with her own body extended to anxiety over her ability to satisfy her new wife. Although not always the case, it was often Sonya who initiated sex, or made the moves, and it was not in the least bit uncommon for Jessica to either feign sleep or a headache in order to avoid it. It wasn't that she didn't love her wife; far from it. She did, very much so. It was just that she was just was increasingly uncomfortable with the sex act.

Occasionally, Jessica would be on the bottom while Sonya rode her, and she started to wish and fantasize that it was she who had the pussy, and that it was her who was being penetrated. She began to imagine that the situation was reversed, and she imagined she could feel her pussy being filled, of a cock deep inside her, filling her up, fucking her. Whenever this happened, she had the biggest orgasms.

Somehow it worked, some of the time, at least, since they conceived and gave birth to a son and became parents. Jessica found herself forced into the more typically male role of breadwinner, working two jobs, while Sonya stayed at home to raise their son.

Five years into their marriage, Jessica changed jobs and started working for a discount fashion retailer, even more heavily staffed by women. Whereas she had previously shunned all things fashionable, she now embraced it; she developed a major shoe craving and an interest in clothes and fashion in general. She made an effort to dress fashionably, albeit in male clothes, but was particularly taken with women's fashions. She managed the lingerie department, amongst others, which she adored. Until then, to her, lingerie was either purely functional at one extreme, or, purely sexual with almost no functionality at the other. Yet here were beautiful, pretty and functional lingerie sets; she loved the silky fabrics, the femininity of them, and loved merchandising them and making the department look spectacular. And her sales soared, beating out all the local competition, both other stores within the chain and competitors.

While there, she met many attractive women, and, aside from being attracted to many of them, she found herself thoroughly envious of their looks and their womanly figures, and wanting what they had, to look like them and be like them. Towards the end of her marriage to Sonya, Jessica found herself obsessed with lesbian pornography and erotica. She wasn't really sure what the allure was; it didn't make sense to her for a man, any man, to be interested in lesbian sex since, by definition, men were excluded. Gradually it dawned on her, however, that she wanted to be one of the participants, however daft or ludicrous that seemed.

A few years later, now working at a furniture retailer, she was told by a clairvoyant who also happened to be on the cleaning crew, that there are, or will be, two women in her life, one who she had yet to meet but whom she knew well, and another who she would meet, and that with whom she would emigrate to America.

Eight months after she and Sonya separated, Jessica found herself married again, to an American, and almost two years after that, leaving England to move to America. The marriage, however, was a disaster, except for the daughter that they bore. Seven years after they were married, when her daughter was just four, Jessica was divorced for the second time.

Alone now, she was determined to spend some time by herself to figure out what she wanted for herself, what she wanted in a partner, and what she had to offer a partner, but most of all, who she was, what she was, once and for all. It was a gradual process, but, it culminated in a vacation two years after the split, when it all began to fall into place.

While on vacation, Jessica read a short story about a young man who chose to grow boobs by taking female hormones. While she wasn't entirely sure about the feasibility, her reaction stunned her – without any hesitation, she immediately knew that she wanted the same. "Well that's just ridiculous! How could you do that, and why? What brought you to this?" she asked herself. She determined that she was going to remain a man, but with boobs; "I'm not about to become a woman." She even told her brother as much after debating and agonizing over it for some time.

But try as she might, she just could not shake this thought from her head; that she wanted boobs. And she couldn't deny the memories of wanting a pussy, of being fucked by a cock, or better, to be fingered and licked by another woman, of feeling a woman's tongue in her pussy, on her clit, bringing her to orgasm. Still, she maintained, she wasn't about to become a woman. Even as she accepted that she wanted breasts, as strange as that was, she was adamant that she was not, and did not want to be, a woman. But those desires, feelings, urges, call them what you will, just would not go away - those desires to be a woman, despite her protestations to the contrary.

Over the next few weeks as she agonized, Jessica thought back over her life, over all that had happened, all the incidences, feelings of insecurity, of confusion, of her distaste of male company, of her wanting to look and feel like the other women around her. And she had to separate fact from fantasy, and, more importantly, sexuality from gender. Until then, she had no clue that they were different. A statement she had made to a co-worker one time came back to haunt her: "I don't understand these men who, want to become women, and then come out as lesbians. Why not just stay male if you like women?" She began to understand, and it began to sink in. There was a sexual aspect, but this was more than mere fantasy. This was an issue of identity, of who she was. What she was. Of her gender.

And two things gradually became clearer: that she could not hide from herself any longer. Now that it was presented to her so clearly, she couldn't pretend it wasn't so. And that she was, in fact, a woman. Just in the wrong body.

Jessica started to conduct extensive research. What did this all mean? What could she do? What are the implications? She was both ecstatic and terrified. "Are you absolutely certain about this?" she kept asking herself. In her research, she searched both for answers to her questions, and for all the reasons why she should not act on this, playing her own devil's advocate. But with each turn, every time she encountered a horror story, of occasions where men had undergone sexual reassignment surgery, or had lived as women without the surgery, only for it to go horribly wrong, she became more determined and more certain than ever.

She was advised time and time again that to come out as transgendered or as transsexual meant risking losing everything: her job, her home, her family and friends, access to her children, her health; even, potentially, her life. She clearly did not want to lose anyone or anything, but, she acknowledged, it was a risk she had to take. It was increasingly obvious to her that she could no longer go on pretending to be a man, trying to fit in; she was not a man, not on the inside. She was a woman, and therefore, the reason that she had not been able to fit in, that she was "not like other guys", was that she did not not fit in with herself.

So, since she could not change the inside - and did not want to - the only thing left was to change her outside, her body. She had to become a woman outwardly, to synch with the woman that was inside her.

One of the first steps Jessica took was to invest in an herbal feminization program, which explained the steps to take and the herbs to purchase, how to look, walk, talk, and act in a more feminine way. She started to deprogram herself of all the training, nurturing, parental and societal programming; all the mannerisms, body language, speech patterns, deportment, even handwriting, that she had adopted that all combined to tell the world around her that she was a man. And she started to relearn how to walk, talk, stand, sit, speak, write and act as a female, all the while trying not to become a cliché; she did not want to become a caricature or a stereotype, to act like a man pretending to be a woman. She started learning quite simply, to be herself; to be Jessica the woman, not Jessica the man, while retaining her essence of being, and her basic personality. And of course, she considered surgery.

She learned the difference between transgender and transsexuality, and in the course of her research, learned a lot about human anatomy, particularly reproductive anatomy. For days, weeks and months, she became consumed with wanting female genitals and to be beautiful; where she had previously felt uncomfortable with her male body parts, she began to hate them. She started abusing herself, trying to hurt herself, but acknowledged that she risked serious bodily harm if not careful, of being rushed to hospital with serious, potentially life-threatening bleeding and probable incarceration in the mental ward; she compelled herself, with an immense amount of effort, to quit abusing herself, having to remind herself that she wasn't anti-male; she was simply a woman, with the wrong body parts. Quite simple, really.