by Zoe Brown
And oh, god, but the waiting was hard. The first week of September was the worst: I couldn’t concentrate at all, at work. I kept thinking of the weekend which had just preceded, of my time in Venice with a beautiful, sexy young woman, and of how desperately I’d wanted to be able to switch places with her, to be ‘the woman’ in her place, to have her breasts, her curves, her flat smooth pelvis, her ripe thighs, her wide hips, her round bottom, and her wet, welcoming womanhood. The arrival of Barb Markham’s newest Executive Assistant, Amy Cho, that same week only made things worse. Not that it in any way negated the extreme skillfulness with which she set about taking up the tasks of her new position, but in person, Amy Cho turned out to be one of the most exceptional specimens of womankind that I had ever had the pleasure to lay eyes upon. She was elegant, and feminine, and beautiful beyond compare, and she walked and comported herself with an air of confidence and self-assuredness that was deeply sexy. I wanted to be her with a desperate intensity. The first week that she was worked for the company, I found myself getting distracted by an intense yearning, aching desire to have a copy of her curves, her femininity, her sexy womanhood for myself, whenever the two of us were in a room together, working: during a board meeting, or a shareholder’s call, or an afternoon coffee and suggestions ‘jam session’ with the brightest and the best of our young new Executive Assistants. I had to escape to my office to relieve that particular, yearning desire on more than one occasion.
But taking the opportunity now and again for a little bit of ‘executive time’ wasn’t enough to stave off all of the consequences from my growing, deepening desires, as it turned out. Miss Cho, it seemed, had picked up on the interest that I had been paying towards her, however unintentional it may have been, and misinterpreted it: one afternoon, the Friday of that first week in September, when I retreated to my office for a bit of ‘executive time,’ I found my CFO’s hot, capable new Executive Assistant waiting for me. She was sitting on the edge of my expensive, mahogany desk, long, pantyhose-clad legs crossed sexily at the thigh, leaning back, her chest prominent, and her hair down and loose around her shoulders. An extra pair of buttons on the top of her blouse were undone, revealing two inches of white, soft, perfect breasts and lacey creame-colored bra, her hair was slightly tousled, and her eyes were glazed over with faint excitement as she turned towards me. I was fortunate that day in that I caught sight of her before fully entering my office! Coming up short, I stopped in the doorway – the as yet open doorway, thankfully – of my office and asked the young woman sitting on my desk how I could help her. With an excited, yearning expression of her own, the beautiful, dark-haired girl quickly uncrossed her long legs, sauntered across my office towards me atop a pair of elegant, three-inch high heels, and pressed herself against me, wrapping her arms around my head and brushing her lips eagerly against mine.
“I’ve been looking forward to this,” she whispered into my ear after pulling away from the kiss.
“Oh?” I quickly and gently tried to disentangle myself from the beautiful young woman, discreetly slipping an arm through the open door of my office and waving my own Executive Assistant, Brendan, on over so that he could help me out of the sticky situation that I’d accidentally gotten myself into.
“You’ve been watching me ever since I first arrived,” Amy purred at me, only belatedly starting to protest as I slipped out of her grip. “I was waiting for you to call me in here—all the girls are always talking about you, I was sure…”
“I’m sorry, Miss Cho,” I finished unentangling myself from her embrace and removed myself a few feet away, wincing apologetically and shrugging one shoulder at her. “I don’t sleep with my employees. Ever.” She wasn’t completely wrong, though: it was true – I did feel that aching need, that desire to sleep with the beautiful young woman in my office who was all-but throwing herself at me, but I knew – the more obvious reasons aside – that losing myself in the lovely young Miss Cho’s physical charms would be a bad decision: it would only but further aggravate the even more insistently most aching, yearning desires that lay concealed within me. I might finally, really lose control, then. And then how would Miss Cho respond when she came home one afternoon to find that I’d masturbated into a pair of her sexy, lacey panties? Or that I’d finally given in and taken a Werewoman pill and was now trying on her sexy lingerie while I thought she was away. Or if I got drunk and accidentally confessed my true desires to her? It seemed totally implausible that such revelations could go any other way than horribly wrong.
When Brendan appeared in the open doorway, I sighed with relief. “Take a few minutes to straighten your clothes if you like, and then Brendan here,” I said, louder, loud enough so that a handful of the young men and women working outside my office could hear me, “will show you how to get started on those files.”
“Files, right, Boss,” Brendan nodded comprehendingly from the door, shooting a friendly smile at Amy and pointedly ignoring her half-unbuttoned blouse. Amy took another a moment to glance back and forth between my young, smiling EA and myself, then quietly adjusted her clothing, smoothed down her hair, pulled it back into a quick ponytail, and slipped out of the office, nodding at me. “Thank you for clearing that up, Mister Rhodes,” she clipped out at me as she exited.
I slumped down into the chair behind my desk once she and Brendan were gone. Brendan had helpfully closed the door after the pair of them. Then I remotely locked the doors and shuttered the blinds so that I could finally relieve myself of the even-yet-more-inflamed secret desires that I had originally been making for my office to take care of anyway. Once again, a fantasy about becoming the Miss Cho’s hot, sexy, gloriously-female twin got top billing in my imagination that afternoon. I even tossed Brendan in towards the end, for a double-helping of naughty, kinky eroticism, imagining myself posing as Miss Cho and seducing my attractive, handsome young Executive Assistant without him ever guessing that the girl who was coming onto him, the girl who was climbing on top of him and undressing him and riding his big, hard cock was really his middle-aged male boss in disguise the whole time…
Chapter Nineteen
Timestamp: Friday, Twenty-Eighth of September, 2018. Now.
At the same time that my hand was becoming smaller, softer, more youthful and, yes! More feminine, in the mirroring reflection looking back at me from the elevator doors, I could see that other changes were also beginning to kick in all over my middle-aged male body. The rich, immaculately styled silver-grey locks on the top of my head were beginning to change color. The roots of my hairs began to darken, turning even silkier and softer as new color started creeping down the strands of my hair and my hair began to flow down the sides of my head and over my ears. The new, dark tones continued to deepen, with dark brown roots that began to shoot out of the top my skull and through the rest of my rapidly growing hair. Meanwhile, I could both see, and feel my prodigiously lean, muscular frame begin to shrink in on itself.
Pop-pop-crack! Snap!
“Unnnnnhhhhh…” Pleasure-filled groans floated from my lips as I squirmed in the grip of the invisible force that was molding and reshaping my body, the feelings racing through me every bit as pleasurable as the sensation of having a woman run her hands firmly up and down my erect shaft. As a man, as Ashton, I had been slightly on the tall side of average, at around six feet and an inch (two in some good shoes), but as I started becoming Ashley I just started shedding inch after inch of that height, and quickly. I grunted and groaned repeatedly in time with the slow but steady shrinking of my entire body. In the reflective surfaces of the elevator all around me, I could see that inches were absolutely falling away from my shrinking body, three, maybe four, maybe even five, maybe even more! And not just in height but also in the width and diameter of my chest, and my shoulders, once broad and thick, were slimming down in on themselves, shedding muscle and bulk by the second. There were a few soft, barely audible popping and cracking sounds as my shoulder bones compressed in on themselves, each of which was a
ccompanied by a burst of orgasmic, sensual squeezing sensations across my body and an echo of the same in my groin as my cock suddenly – ‘AHhhhhh! Fuck!’ – began cumming, shooting a load of my ejaculate into my boxer shorts without any warning whatsoever.
Oh shit! I thought with a sudden burst of alarm. I had forgotten about the cum. In all of my planning, I’d overlooked that tiny detail – or maybe not so tiny. Both Brianna and Jade had been experienced Werewomen when I’d met them and witnessed their transformations – they were old hats at having a solution on hand to prevent the mess that their cocks would have otherwise made as they emptied themselves, and their balls, of every last drop of sperm that remained in their testicles prior to the transformation turning their male genitalia into its female equivalent. Me, on the other hand – well, it was my first time, and I hadn’t realized until just that moment just how violently and overwhelmingly the non-stop orgasms caused by my transformation were going to ruin the very expensive, fancy male clothes that I still had on.
“Well fuck,” I panted, bracing myself again against the sides of the elevator as I continued to shrink, “Okay!” If soaking my pants and my boxers in semen is the price I have to pay to become a girl today, then fucking BRING IT ON, Werewoman, I’m ready for you!
✽✽✽
Timestamp: Saturday, Fifteenth of September, 2018. Thirteen days ago.
I’d spent each of the first three weekends of September in Violetta’s company, at both her suggestion and insistence. I accepted, not only because it was delightful to spend time with my oldest and dearest friend, but also because it was the easiest way to avoid any more of the sexy, sensual liaisons like the one which had nearly ended in disaster for me the weekend before. We stayed in the city, chiefly lounging about one or another’s loft or hotel suite, sharing some quiet dinners and catching up on twenty years’ worth of ongoing conversations. Surprisingly, at least to my mind, there was nothing sexual between us on any of those occasions, other than a few jokes and turns of conversation. In our twenty-odd-years of friendship, Violetta and I had been lovers on several different occasions, the most recent of which had only been a couple of years ago, a few seasons after her late husband’s death. We seemed to fall into one another’s beds and one another’s arms as easily as other people… bought groceries, or ordered desert. It had become almost a nonevent for us, and yet… in the wake of my coming out to her about my secret gender-bending desires, the physical and romantic chemistry between the two of us seemed to almost entirely vanish, replaced instead by a warm and friendly intimacy that no longer had to tiptoe around the various desires and insecurities that were usually in play. We just relaxed together. She told me about her work, her business, her artistry, the new boutique, and I told her about my secret longings, my urges, my fantasies, which seemed to get ever more complex and more elaborate – and more intense – as the weeks went by. Surprising as it might seem, Violetta found my fantasies endlessly fascinating.
To compensate for my growing urges, however, I also kept myself busy planning my coming feminine get-away, my first excursion out as a woman. Violetta offered repeatedly to help with that, wanting as much to be a part of my first time gender-bending experience as she did to make sure that I didn’t come up with any more reasons to keep putting it off. So on a Saturday night just two weeks before my planned debut as a hot, sexy young woman, with Violetta’s help I went through a long list of luxury resort locations that I kept on file on my phone to find one that would be a perfect place for my hot, young, sexy, college-age female alter ego to make her entrance upon the world. For reasons of secrecy, security, and safety I decided to limit my search to the Californian coast: somewhere within a day’s drive of San Francisco. Given that this was to be my first experienced in a hot, young, sexy female body, I didn’t know how safe it would be for me to try and drive my way across the country, alone (Violetta strongly discouraged the idea as well.) I also didn’t want my destination to be anywhere out of the country, because I didn’t yet have the real, legitimate ID documents for the fictitious young woman that I’d be posing as, and didn’t want to book the flight in my own – Ashton’s – name. I’d already made the decision that, for financial reasons, my female alter ego would have to assume an identity related to my own (some sort of familial connection) so that I could justify adding her as a secondary user on my credit accounts. If those ‘family connections’ ever came to light in any serious way, eyebrows would start going up, but I couldn’t think of any other way to get legally-valid credit cards for a young woman no one had ever heard of before. Any more connections between ‘her’ and myself were to be avoided wherever possible. If, after my first adventure out in the world as a beautiful, sexy young woman, I decided that I wanted more of that experience, then by that time my female alter-ego would have some ID and some credit cards of her own to take her overseas, or wherever she wanted to go.
And speaking of ID, when Violetta pressed to find out exactly what sort of strings I was planning to pull to get my feminine alter ego some real, legitimate ID, I hedged around a bit before I finally revealed to her that I ‘knew a guy’ with tangential connections to the old Sicilian Mafia that still had an extensive network here in the city. For the right price, I was sure, I’d be able to order some ID cards for my, um… hmm… “My cousin,” I decided at last. “Second cousin. Daughter of a younger half-sibling my father barely knew…”
Violetta had expressed some concern about me turning to the Mafia for help acquiring ID for my ‘cousin,’ but mostly of the vague and non-specific kind. “What if they start asking questions?” She asked me one evening, over a glass of wine and some pasta, “Want to know who she is, where she comes from, why no one has ever heard of her before, why she cannot acquire identification on her own?”
“Why should they care?” I’d countered, genuinely surprised by the idea. “There must be plenty of people who go to the mob for help with their ID – illegal immigrants, ex-cons…”
“Perhaps, but, darling, you are a famous person. Your involvement… it makes everything more suspicious, no?”
I’d shrugged, not entirely convinced that she might not be onto something there, but chose to ignore her concerns. For the same reasons that I did not want to book my as-yet-non-existent female persona any airfare tickets under my own name, or with my credit cards, I had similar reservations about trying to pull any official connections in order to get some ID made for my… well, the girl-me. People were bound to start asking questions then, especially if their own bureaucratic jobs might be on the line, and while I might have the money and the influence to pull it off, I didn’t think that I could trust members of the official bureaucracy to keep things as quiet as I would like them to be with regards to these affairs. The mob seemed the easier, simpler option. Slightly less legal, perhaps, than pulling strings at the DMV and the Social Security Administration, maybe, but far less likely to be leaked to the press, or so I had always assumed about dealings with the Mafia.
“What if, some day,” Violetta had pressed one last time, taking another bite of her ravioli as she did so, “They want something back from you in return?”
Again, I shrugged. I had no real answer for that, but I also didn’t really feel like it was anything worth worrying about: I was paying them, after all. I did make a mental note to make sure that my payment was on the generous side, however. Perhaps if the men (or women) in question did have any particular notions in that direction, the extra remunerative might dissuade them?
“What do other, hmmm… what did you call them…?” Violetta scrunched up her face and stared at me, then jabbed her fork in my direction, “Ah! ‘Were-Women’ – ‘Werewomen’ – What do other Werewomen do about identification? Do you know? Have you asked?”
I’d winced in response to that question. I had not, actually, as it turned out, asked that question of either of the two Werewomen that I knew. In fact, I hadn’t even spoken to Jade, or to Brianna, in a little over two weeks at that point. It wa
sn’t exactly that I’d been avoiding them, really, but once I’d made the decision to try out becoming a hot, sexy girl myself, I’d started feeling awkward about revealing that decision to either of the two beautiful young gender-bending ladies that I’d been intimate with in the weeks leading up to that decision. I felt a little… ashamed, whenever I considered reaching out to them: embarrassed, I suppose, about my decision to try becoming a girl, like they had.
“But why should you feel any such thing?” Violetta had laughed, when I’d told her. I tried explaining it to her, and I made a bunch of noises about having been a ‘man’ to them when we’d been together, a handsome, charming, masculine man that they had enjoyed being pursued by, desired by, wooed by, and screwed by, and how I didn’t want them to feel differently about me, or was afraid that if I told them what I was planning, that they would feel differently about me, and that it would feel like some sort of confirmation that I really was a weak, effeminate, ‘failure’ of a man for wanting to become a woman, for making the decision to give it a try…
It all came out of me in a jumbled, rambling mess of feelings and fears, and Violetta had done her best not to laugh at or roll her eyes at any of them, but when I finally reached a breathing space amidst my ramblings, sipping some of my wine and trying to collect my thoughts and order my feelings, my dinner companion had abruptly rolled up her napkin and launched it at my head. I’d caught the collapsing cloth projectile on the rebound and raised my eyebrows at my friend. “What was that for?”
