Addicted to Womanhood 1

by Zoe Brown

  Or was I just burned out, and in need of a break, and it was just that this – this whole gender-bending obsession of mine – seemed like a perfect, sexy way to really get away from it all for a while?

  “And, also, it just occurred to me,” Jade’s eyes got wider and more insistent as she kept on giving me reasons why I should consider that I might actually want to give the whole gender-bending thing a try. “You also don’t seem to get along really easily with other guys, you know?”

  I frowned. Huh? What would have ever given her that impression? I wondered.

  Jade must have seen the confusion on my face, because she quickly answered the unasked question. “Do you have any close guy friends? How do you know them?”

  “Well, yeah, of course,” I held up my hand and started counting off on a couple of my fingers. “Justin Haley, over at PRATech – we play racquetball at the club every other Tuesday; he’s one of the most talented negotiators that I’ve ever had the fortune, or the misfortune, of dealing with. And, um… Byron Bender, he’s one of our big investors and an old fraternity friend from college, we get together a few times year to hit the clubs and meet beautiful women, just like in the old days… um…”

  Jade nodded. “Go on,” she encouraged me, a fetching smile tugging at her lips, as she turned the car off of the street and down into the parking lot beneath my building, “you must have more than two, right?”

  “Right, right. Well, uh…” I tried to think. “Ben Nguyen, he’s CEO for ReinPower, we were in business school together; we get together for dinner and drinks whenever one of us in town, and um, Sergei Sokolov, we were street fighters together in our thirties, and now he shoots me an e-mail whenever he discovers some new thrill-seeking adventure that he thinks we should try—”

  “—okay, but you do hear yourself, right?” Jade cut me off with while I was still speaking, laughing at me as she coasted into one of my three reserved parking spots beneath the building. “These are all men that you compete with. Can you talk to any of these men? The way you love to talk to women? The way you’re talking to me right now? Do you ever just enjoy being around them, relax with them, the way you love to relax with women? Do you feel like you can really be yourself around any of these men, or do you always have to put on some big, badass, masculine front?” Putting the powerful foreign automobile into park, the pretty girl with the dark-brown hair wriggled around in her seat so that she could cock her head to the side at me and raised two delicately arched, femininely-shaped eyebrows in my direction.

  I frowned back at her for a moment longer. I had a strange, sinking feeling. She’s right, I conceded internally.

  “No,” I said at length, reluctantly.

  Jade reached out with one hand and gripped one of my own, giving it a little squeeze. “You’ve been trying to out-compete all of these guys your whole life, using your success in business, and with women, and in your ‘thrill-seeking’ to convince yourself, and everyone else, that you’re really, really masculine, and it’s worked, up until now. But now… it’s starting to feel a little hollow, and you’re looking around and wondering… ‘okay, if not this, then what do I really want?’”

  I sighed, running my hands up into my hair and over the back of my head, reluctantly conceding that she might really be onto something. I was still gritting my teeth, but as much as I didn’t want to believe it, as much as I just wanted my sexy, fetishy fantasies to stay sexy, fetishy fantasies, once Jade planted the idea, I couldn’t shake the suspicion maybe there really was something… more to them. I felt the defensiveness inside of me starting to recede as I let that possibility really settle in. But the shame of giving in to my emasculating, effeminate fantasies and the fear of being found out were not as easily extinguished. “I still can’t,” I muttered, sighing heavily. “If anyone found out, I’d be ruined. No one would ever do business with me again. The whole company could go under. I could never take that sort of risk.”

  “Oh, come on,” Jade rolled her eyes and slipped into Spanish for the second time this evening, her eyes flashing darkly at me as she growled into my face, “Tu tonto culo! You’re one of the richest people on the planet! You’re trying to tell me you couldn’t arrange get away for a little while, find some way to experiment in secret, without some else finding out about you? Mierda! No! You’re just being chickenshit right now. You’re afraid of taking one of those ‘little pink pills’ because you’re scared that if you do so, that the big, tough, manly-man parts of you might not come back afterwards. You’re afraid you might like being a ‘soft, sexy, sensual girly-girl’ a little too much! That’s what you’re really afraid of!”

  I leaned back away from her explosive outburst and put up my hands defensively, palms out towards her. “Hey! Why are you getting so angry about this?! Why can’t we just keep on doing what we were doing before!? We were having fun, weren’t we? I mean, I know I was.”

  Jade sighed at me, folding her arms over her chest and pouting out at the front window. “I don’t want to be your ‘gender-bending hookup,’ Ashton. I don’t want you to use me for the ‘feminizing kicks’ that you’re too afraid to get for yourself. It’s nice being able to be open with you about who and what I am, and how happy I am to be this way, but I didn’t become a woman so that ‘guys’” she made a pair of big, exaggerated air quotes when she said the word, “who can’t make up their minds about whether they might want to try being girls or not can ‘experiment’ with me and fuck with my feelings until they make up their minds to do it one day. And I know!” she held up a hand again to cut me off when I started to object, “that neither of us mentioned feelings when we started getting into this, but what can I say? Apparently, I was more ready for the ‘right guy’ to come along so that I could take another stab at being someone’s girlfriend again than I thought I was. I’ve really enjoyed myself with you that much. But I can’t be yours…” she shot me a look, a significant look, “not unless you take some of those pills for yourself, get all this gender-bending shit out of your system, and then decide you’re happier as a guy afterwards.”

  Jade leaned across me, opened the passenger side door, and waved for me to get on out of the Ferrari. “I’m keeping the car while you think it over. I’m sure you won’t mind, it’s not like you don’t have enough money to buy yourself another.” She stuck out her tongue at me. “Look, it worked for me, so maybe it’ll work for you: I dare you. Take a few pills. Try shit out with ‘a pair of tits and a vag’ for a while. ‘Woman up,’ for fuckssake, and then get back to me, and we can talk things over. And who knows?” She flashed me a brief, flirtatious smile, “I might actually be even hotter for a guy who could take a stab at being a hot chick for a while and then come back from the experience confident of his manhood and secure in his masculinity. Some dude who didn’t need me for gender-bending kicks. Now get the fuck out the car so I can leave.”

  I hesitated for a moment, frowning at her and not entirely convinced that I was willing to just let her leave with my car, but then a moment later I shrugged, deciding it really wouldn’t make any difference to my life if she kept the car for a day, a week, or a year, and did as she told me to do, sighing in resignation as I slipped out of the vehicle. “I can’t believe you’re just taking my car,” I muttered at her as I closed the door behind me.

  “Well, come on now, look at me,” Jade grinned at me through the lowered window and waved down at herself, at her hot sexy body encased in the sleek, sexy pink dress she was wearing. “I look way too fucking hot tonight not to have some dude’s cock all up in my pussy.” She wiggled her eyebrows at me. “And with a ride like this, I bet I can find some hot stick to chase me around the city for a while before he pins me down and makes me his woman for the night.” She winked at me when she saw the slight stir of arousal that the fantasy image her words inspired in my imagination caused in me, and then grinned. “Now go on, ‘girl,’ get in touch with your feminine side for a while. And hey, if you need some help with that, you can look me up – b
ut until you’ve had at least one hot stick of your own up in your own gender-bending Werewoman pussy,” I sucked in a breath and shivered, and she grinned even more broadly at me, enjoying the effect that her words were having on me, “I keep the car.”

  Then with that, she threw the car into reverse, revved up the engine and backed swiftly out of the parking spot in the garage, reversed gears again, and then peeled out of the underground lot with a squeal of tires, waving at me out of the driver’s side window as she roared up onto the street, and out of sight.

  Chapter Sixteen

  Timestamp: Sunday, Twenty-Sixth of August, 2018. Thirty-three days ago.

  I spent the following day after Jade drove away from me in my car alone, holed up inside of my penthouse apartment, staring at the half-empty baggie of little pink pills that I’d taken out of my bedside drawer and placed on the coffee table in front of my couch. I spent the day ruminating on the argument that I’d had with Jade the night before, on the fantasies and the desires that had been plaguing me ever since the little baggie and the gender-bending bartender had entered into my life, bringing with them the promise and the possibility of experiencing a taste of what life might be like on the other side of the gender divide, an experience that, to my profound surprise, I was deeply aroused to contemplate and deeply interested in having for myself. Jade was right! I found myself admitting, sometime past noon, as I sipped some French silk coffee and turned one of the pills over and over in my hand, I did want what she had! Last night when she’d grabbed her own breasts in front of me and run her hands down the swell of her curves and over the taut flatness of her tummy, I had ached to have those same swelling curves and taut, tight tummy and big, beautiful breasts for myself. I wanted to know what it felt like to be a woman like her, I wanted to experience womanhood for myself. The idea was sexy to me, it turned me on, and even if I didn’t entirely know whether or not Jade was onto anything when she’d guessed that ‘all my life’ I had been struggling and fighting and competing for masculine success and acclaim so that no one could accuse me of being anything less than the man that I appeared to be, so that no one could suspect that I might harbor an interest in trying out life as a soft, small, sensual young woman for a while, instead of a big, strong, powerful and successful man… her guesses did give me pause, and that made me stop and think.

  And even though I was afraid, afraid of being found out for my gender bending fantasies, and for my potential gender bending acts, afraid of being cast down from the pillar of masculine success and castigated for my effeminate fantasies and emasculating desires, and fuck, yes, Jade was right, even afraid that I might come to like the experience of gender-bending, of becoming a hot, young, sexy woman too much, and that I might not want to go back once it was all over, I couldn’t find a way to argue with Jade’s reasoning, in the end: the only way I was going to be able to prove to myself, or to her, that I didn’t really want to be a woman, after all, that my desire to be with Jade didn’t just have to do with using her as a safe conduit for my own gender-bending fetishes and fantasies, was to have that experience of using Werewoman to become a hot, beautiful, sexually-active young woman myself for a while! To fucking ‘Woman Up’, as Jade had said, and just do it! To stop hiding behind my masculine insecurity and actually put my gender identity to a test! Was I really a man, underneath it all, or was there something else I would rather be? Did I have the guts to try being a beautiful girl long enough to find out, one way or another?

  And fuck, I decided, sometime shortly before dusk, as I picked at a grilled chicken salad and slowly browsed a subreddit dedicated to Werewoman and gender-bending, slowly making up my mind to really give this whole crazy fantasy a try, It’s not like I won’t come back to myself after I’m done with it all.

  ✽✽✽

  Timestamp: Monday, Twenty-Seventh of Augus, 2018. Thirty-two days ago.

  The next day, although I returned to work promptly once the weekend was over and – ostensibly, at any rate – disappeared into my office with a stack of reports to review and a weekend’s worth of calls to return, in reality, once I got behind the closed shades of my private office, I threw myself down on one of the plush, enormous leather couches positioned in front of my desk and waited, only for as long as I thought it was polite to wait on a Monday morning, for an opportunity to place a long, long overdue call.

  At a handful of minutes past ten the line connected, and a soft and familiar-sounding voice answered the phone a moment later in a faintly-Valencian accent, with a delighted note of surprise: “Ashton?! Is that really you? Are you actually calling me, today?! I’m staring at this caller ID notification but I’m not sure that I believe it. Did you know I’ve actually been trying to get you on the phone for the better part of a month?! Your secretary kept telling me that you were unavailable.”

  “Yes, yes, it’s me… hello, Violetta.” I smiled into the phone and let the top of the device fall onto my forehead and rest there while I closed my eyes. Just hearing her voice drained some of the pressure and the stress of my warring fears and desires away. “I’m sorry, I’ve been…” I let a resigned sigh out and then copped a mea culpa. “I’m sorry, it’s entirely my bad. I’ve had a lot on my mind. I haven’t really been seeing anyone the last few weeks, aside from some…” How to explain Jade and Brianna? “… some other people with situations similar to my own.”

  “Ohhh!” Violetta exclaimed with some concern, and I could imagine her long eyelashes fluttering as she tried to think of something vaguely comforting to say. “Dear me, has something happened? Is everything alright? You’re not ill, are you?”

  “No, not ill,” I shook my head with another smile. “And, um… yeah. Yeah, everything’s fine—,” I started to reassure her automatically, already questioning the wisdom of my call, rethinking what I’d been planning to do, when some of what Jade had said to me the previous weekend, before storming out of my loft and slamming the door behind her, filtered its way back into my thick skull: ‘Sometimes you wake up in the middle of the night, and you look back on your past, and you wonder ‘what the fuck am I doing with my life?’ ‘Cause when you’re fucking honest with yourself, none of it feels real to you, does it? It’s all a big fucking sham! …Woman up!’

  “Actually, no,” I murmured softly, a moment later. Violetta was quiet on the other end of the line. Listening. I smiled again, in spite of my mood. She’d always been able to pick up on when I was bullshitting her. “No, things haven’t been alright lately. But… there’s a chance that they might be about to get much, much better,” I admitted, louder and more honestly. “It’s just… there’s something that I … deeply and desperately want to do, something… socially taboo, but which excites me and thrills me. But I’m afraid, Vi, that maybe I shouldn’t, because of what it might mean for me, if I do, how it might change me, and also because if anyone found out about it, I could be ruined.”

  “Oh, my dear friend,” the magnificent woman on the other end of the line whispered fiercely. “I’m both excited and terrified for you! What is it? What do you want to do?”

  I didn’t know how to explain it to her. I couldn’t go into details now, not here, not in my office. Even in the absolute, soundproofed privacy of my office space, I didn’t feel secure from the prying eyes, ears, and fingers of the rest of the corporate sharks that swam in circles all around me, even the ones that ostensibly worked for me. The sharks I’d cultivated, trained and honed for years. One hint of blood in the water, and they’d be all over me inside of a heartbeat. I knew that beyond a shadow of doubt.

  No, I couldn’t talk here. If I was going to talk at all, it had to be somewhere outside, away from the office, away from the workplace – the workplaces of the world. Somewhere where the noise of life and the city could afford me a few minutes of privacy. Time enough for me to have a talk with and get the advice of my oldest and dearest friend.

  “Actually, Vi,” I replied, “How would feel about me dropping in on you this morning?”

&n
bsp; ✽✽✽

  Blowing out of the office at a quarter after ten, to the stunned faces and wide-eyed disbelief of many of my subordinates, I had Brendan hold all of my calls until the afternoon but forward all pressing business to one of the managing execs – Sassani, or Hanna Kulczyk, Rhodes’ Chief Operating Officer. I didn’t usually pass off work onto my upper management in that way – as previously noted, I was notoriously fastidious about making sure that everything that came across my desk in my capacity as the Firm’s CEO was handled by myself and by myself alone (or by an Executive Assistant whose judgement I could trust) – but today I really didn’t care. I also let the young man at the desk right outside my office know that I’d be seeing an old friend for the duration of the morning. I was sure that the news would get ‘round the office in short order after that: Violetta d’Cardona was in town, after all, and I had no doubt that the office’s clerical staff was well aware of that. I expected that interested parties within the firm would put together their boss’ early, mid-morning siesta with the esteemed lingerie entrepreneur’s presence within our fair city and hatch some rumors about our ‘on-and-off-again’ ‘love affair’ being ‘back on.’ And then sometime later this evening society blogs would start publishing photos of Violetta and myself together strolling through the city, and in their minds my subordinates would feel that their suspicions had been confirmed. And it would all be wrong, of course, but it was a much more ideal alternative for them to believe that than for them to have any idea, whatsoever, about what was really going on with their boss.

  I called a cab as soon as I stepped outside of the building. There were usually a handful of yellow-checkered vehicles idling around outside, down here in the heart of the financial district, ready to whisk various high-level executives and middle-management-types away to luncheons, presentations, client meetings, and afternoon consultations. They didn’t usually ferry corporate bigwigs like managing executives and CEOs about the city, but today I wasn’t much in the mood for taking one of the company drivers along with me down to Union Square, however much more convenient it might have made getting around in morning traffic. I wanted to be alone with Violetta. I wanted to be able to speak honestly with her, and get an honest opinion in return. I couldn’t afford the possibility that anyone who knew me by name might be listening in.