by Zoe Brown
Timestamp: Friday, Twenty-Fourth of August, 2018. Thirty-five days ago.
Jade and I made plans to meet up again the following weekend, once again eschewing the formal dinner-date and arranging to just hook-up after she got off of work on Friday evening, instead. As before, I picked her up outside the Lounge in the Ferrari, with a freshly-baked pizza riding on the passenger’s side seat and a six-pack of her favorite soda drink, Coca-Cola, wedged into an uncomfortably tight corner behind my shoulder. Also as before, I prepared to give up the driver’s seat for the hot, tight-leather-pants-and-pink-bustier-wearing goddess when she emerged from the Lounge, waving a somewhat frantic farewell to the several persistent admirers who had followed her all the way through the joint and out the front doors, trying in vain to persuade her to go home with one of them, instead. When the Ferrari’s engines gently rumbled to life out in the dark, parked along the curve, waiting for her, the throng dispersed, and with a laugh and a grin and a giggle of excitement, the dark-chocolate-haired, cocoa-eyed vixen had dashed across the remaining distance in four-inch high-heeled black leather boots and then literally thrown herself at me, crushing my body back against the car and wrapping her leather-clad thighs and arms tightly around me as she pressed her hungry lips against my equally passionate own.
“Fuck, I missed you!” She groaned, when she finally tore her mouth free of our hungry, desperate kiss, softly panting for breath and beaming up at me.
“I missed you, too,” I laughed, surprised and delighted at her enthusiasm for seeing me again, although somewhat taken aback by the intensity of it. A slight niggle of concern wedged itself into the back of my mind as I helped the beautiful young woman off of the sidewalk and onto the cobbled streets outside the club, then into the driver’s seat of the car. Had I misjudged the nature of Jade’s interest in me, I wondered? I had thought that it was primarily about the sex and the openness with which she could interact with me, but the shining eyes with which she looked at me as I slipped into the passenger’s seat beside her seemed to suggest that there might something intensely emotional at play as well, and that began to worry me. As much as I had fervently denied the truth of the matter to her over the past several weeks, and as much as I continued to cling to my defensive masculine insecurity to both inwardly and outwardly front that I had no real desire to become a woman, as Jade had done, and as Brianna was doing, a façade that was far easier to maintain while I was able to get plenty of vicarious gender-bending kicks from being in a sexual and intimate relationship with a gender-bender like Jade, I knew in the back of my mind that my particular house of cards with regards to the security of my gender identity and lack of desire to explore gender-bending for myself was a bit… fragile, and I was afraid that it might not survive an attempt to move our sexually intimate connection towards a more emotionally intimate place.
With the Ferrari’s powerful, playful engine roaring to life beneath Jade’s skillful control, we blasted up north across the Golden Gate bridge again, although this time we didn’t stop for a quickie in the parking lot of an office supplies depot before turning back. This time, we kept heading up on north, cruising along at a deftly-manageable fifteen miles above the legal speed limit as we burned towards the Sonoma drag strips. I put up the entrance fee that allowed us into one of the later heats of the evening, and Jade remained behind the wheel for the action, positively purring with excitement as I whispered into her ear that this time she didn’t have to put on the pretense of being Giuliano as she tore down the race way in a souped-up import that could otherwise have been traced back to her male alter-ego. Tonight, she could just be the incredibly sexy young woman that she really was underneath that old disguise, whipping the pants off of all the brash, over-confident young men who crowded around our car as we taxied into position in the starting blocks, alternating between playful taunts and aggressive come-ons aimed at the hot girl behind the wheel. She could whip the pants off of all of them, driving a hot-rod Italian elite import that only a handful of people in the world could get their hands on, and then, once the race was over and she’d collected the prize money, she could ride my cock in a victory celebration that would last all night long.
There was nothing about my proposal that Jade didn’t relish the opportunity to enjoy, and she proved it so, thoroughly roasting the competition as she blitzed past them towards the finish line, with the Ferrari roaring eagerly away under her cool control, and once she’d collected the prize money – to the appreciative wolf-whistles and cheers (and a few boos) of the track crowd – she drove us just far enough away from the tracks to get us the barest screen of privacy behind some thin trees and some bushes, then pulled me out of the side passenger door of the Ferrari, backed up onto the hood of the car once more, stripped out of her tight leather pants and excitement-dampened white lace panties, straddled my hips on top of the hood, and rode my cock for well over an hour before she was spent enough to drive us back into the city.
✽✽✽
We made love several more times that evening, experimenting with some positions that were new to her and a couple of things that she’d always wanted to try from the female side of the sexual equation, before finally dropping off to sleep in one another’s arms. Then again, twice more the next morning, before we finally rolled out of bed together and started puttering around in the kitchen, putting some donuts and bits of fruit and cheese together on a platter for us to pick from and brewing up some caffeinated beverages for the both of us. We were both looking forward to another fun-filled weekend together. Jade wasn’t technically scheduled off work for Saturday night, but she was off for Sunday, and with her sparkling-eyed, grinning permission, I called up her manager and offered to make a considerable donation to the on-going renovations at the Lounge if he’d find someone else to fill her spot for Saturday night.
“Well, he accepted,” I hung up the phone a few minutes later with a smug and satisfied look on my face. We were curled up on the couch together again, picking through our breakfasts and taking pleasure in one another’s body warmth. Jade had on the Oxford shirt that she’d ripped off of me as we stumbled our way into the apartment and up to my bed the night before, wearing it unbuttoned over the black satin and lace chemise that she’d wriggled into last night after the last of our sexual exertions. There was a glazed donut in her right hand, and a mug of piping-hot, expensive-smelling Italian coffee in her left. I was still in my pajamas, scrolling through the morning news on my tablet and sipping at some coffee myself.
“Mmmmmmm, someone just can’t get enough of me…” Jade purred playfully, batting her long eyelashes at me and munching on her donut. Her lips widened into a smug smile of her own, “And, now everyone at work is going to know I’m screwing a hot, handsome multi-millionaire. I will not mind their envy in the slightest.” She was still smiling, but she was winking at me at the same time. “A millionaire who is so fucking into me that he called my boss to get me out of work for an evening so that he could have his sexy, sexy way with me alllll night long…”
“Yes, well, exceptional women call for exceptional measures,” I retorted, smiling back at her and then leaning in to steal a bite out of her donut.
“Hey!” She swatted at the empty air where my mouth had been after I sat back again, then laughed some more. “Well, speaking as a semi-permanent member of the female sex, let me assure you, ‘exceptional measures’ like that are hot, flattering, …and they make our pussies wet,” She wiggled her eyebrows over her donut at me and twitched her sexy ass from side to side. “And, also… thank you.”
“You’re welcome, beautiful lady,” I leaned in and kissed her again. We both had a mild case of morning breath after sharing a bit of late-night takeout pizza dinner the evening before, but neither of us seemed to mind. Increasingly, we actually seemed to be behaving more and more like a couple the longer that we spent around one another. It was nice, but for all of the reasons that I had contemplated the night before on our ride out of the city towards the Sonoma dr
ag strips, it also felt a little… troubling, for me anyway. I could feel a small, black cloud of anxiety beginning to build on the edges of my mental horizon. I wasn’t sure just what it represented quite yet, but I was sure it would come to me.
“So, what would you like to do today?” I asked the vixen beside me once we both came up for air again. “Sightseeing in the world of the rich and the famous? High-end, luxury boutique shopping? Visit some art galleries and workshops together, maybe play with some clay? Candlelight dinners, tickets to a show…?”
Jade groaned, unhappily, and leaned back and away from me a little bit, still munching on her donut with a glum expression. “NNnnggggg, that all sounds like so much fun… but, actually, I kinda have plans for later this afternoon, already.” She gave me an apologetic look. “And I would invite you along, but they’re the kind of plans that you really can’t show up to.” She lifted one shoulder in displeasure.
“Oh?” I blinked at her, briefly confused, but then I nodded, realization suddenly hitting me. “Ohhhhh. You have to visit your family today.”
“Mmmhmm,” Jade finished up with her donut and sipped some more of her coffee again, holding the mug in both hands. “My youngest brother is a senior in high school this year. He’s the first one in our family, other than our sister, who’s just a few years older than him, to finish school, and he’s playing his first basketball game of the season tonight. It’s an away game, so we’re having a little potluck dinner at five before he heads to the gym.” The pretty young woman on my couch leaned forward and brushed her lips against mine again. “I should be done by seven. I was planning to be at work at eight, after all.”
“It’s no problem,” I reassured her, returning the affection with a smile. “Where are you going to change back into… yourself, after you get away? Should I pick you up there?”
“Umm,” she winced a little. “Unclear? I was planning to go to work today, so I probably would have just stopped off at a family restroom somewhere – I have like, a giant map of those places on my phone – but, um…” she raised an eyebrow flirtatiously at me, “if you’re up for a little bit of a show, I could come straight here…”
I sucked in a breath and shivered slightly, blushing and biting my lower lip as I fought a smile. Jade caught the expression, and the shiver, and the minor tenting in my pajama pants, and she grinned wickedly up into my face, but then her smile slipped slightly, and she frowned. Her eyes darted thoughtfully to one side.
“What’s wrong?” I asked her, confounded by the sudden dip in her mood.
“Nothing,” she responded quickly, smiling brightly back up at me again and shaking her head to dismiss any concern. “Just had a little thought, but that’s…” She waved a hand and grabbed me by the lapels of my pajama top, scooting down onto her back on top of the couch and pulling me over and on top of her, “It’s gone now. Now I want you to make love to me again.”
“Already?” I laughed at her enthusiasm and let the change in expression go, “Jesus Christ, woman, your libido is nearly as insatiable as mine is.”
“Nnnnnnggg…” Jade groaned, yanking me on top of her and hiking the bottom of her chemise up over her hips, wrapping her full, feminine thighs around my waist and rubbing her already damp, slick crotch against the tented front of my pajama pants, “I wasn’t kidding about those ‘exceptional measures…” she growled playfully at me, kissing me passionately between panting for breath, “You wanted a whole weekend to talk, hang out, cuddle, and make love to me… let’s get back to it…”
✽✽✽
We engaged in passionate sex two more times together – once on the couch and then once shortly afterwards in the shower – before Jade reluctantly slipped out of the penthouse, wearing the much-more-disheveled, wrinkled version of the outfit that she’d worn into my apartment the previous evening back out of it again. It was a quarter past four when she left, and she said that gave her just enough time to hop on a bus and get to one of the public ‘family’ bathrooms that she relied upon for a place to safely change before the reversion back into Giuliano hit her, at which point she’d change into male clothing for the first time in several days and then head to her old neighborhood for a potluck dinner. I snorted at her, told her that sounded like a ridiculous waste of time, and tossed her the keys to the Ferrari instead. I could have sworn she squeaked.
During the intervening hours between when Jade slipped out of the penthouse and when she was due to return, I lounged around the place on my own, picking up a little bit after our activities the night before, as well as cleaning up the remnants of our breakfast, then settling down again for a bit of reading while I had the time and the solitude to really dive in. But just as had been the case at the office throughout the previous week, I had trouble keeping my thoughts and attention fixed on the material at hand. Instead, every so often, my thoughts drifted away from the text that I was pouring over and slipped up the stairs into my loft, to the small, now-significantly-lighter baggie of pink gender-bending pills concealed within the drawer of one of my bedside tables. I’d begin absent-mindedly playing with myself as portions of my attention drifted off towards the persistent fantasies in the back of my mind – multiple different competing fantasies, actually, by now all differentially-developed and full of their own intricacies and exciting, naughty little twists that made my cock twitch with enthusiasm as they came back to me again – about what it would be like to take one of the sexy pills for myself, to experience the same sort of sensual transformation and intensely feminine introduction to physical womanhood that I’d seen both Brianna and Jade find so much delight in, to experience for myself just how fun it could really be to walk on the womanly side of things for a while. I still felt the shadow of shame and the defensive insecurity of my masculinity lurking around the edges of my subconscious, but as long as I didn’t allow myself to cum, half-heartedly reading the e-book on my tablet and absent-mindedly squeezing and stroking my cock while I let my fantasies play themselves out in the back corners of my imagination, I never had to confront them.
Of course, the problem with employing that tactic over the long term was that the longer I let myself linger over those fantasies, the more I tinkered with the details, imagining just how such and such a scenario would play out, and in what contexts, and how I wanted it to go, the more the lure and the insistency of those fantasies began to fill all of my mind, and the harder and more straining the twitching cock in my pajama pants and boxer shorts grew to become, until sometime in the late afternoon, around about five-thirty or so, I finally launched myself up off of the couch in the living room with a frustrated groan, setting aside the tablet and the book that I was reading (after trying and failing to read with any level of comprehension and absorption the same page for the third time in a row) and stalking across the limited floor space of my apartment to the bathroom. There I retrieved the discarded black satin and lace chemise that Jade had left lying on the grey marble vanity countertop when we slipped into the shower together, several hours previous. Squeezing my cock through the material of my pajamas and my boxer shorts, I carried the chemise back out to the living room with me, then threw myself down onto the couch and leaned back, groaning as I let my fantasies wash over me, unbuttoning the top of my pajamas and sliding the soft, satiny material of the chemise over my hard, well-groomed male chest, my eyes drifting closed as I moaned, rubbing my cock with my free hand hands, and imagined myself wearing lingerie just as soft and as sensual as what I’d purchased for Jade, only not as myself, as a man, but as a beautiful young woman, just like Jade! I let my imagination supply the images, the sensations, the sounds and the feelings of my body going through the same sort of sexy, sensual transformation from male to female that I had seen Brianna go through twice now, that I was going to get a chance to see Jade go through a couple more hours from now. As my breathing quickened, as my cock began to throb ever more insistently in my hand, I slid the bunched up, satiny fabric of Jade’s nightgown – one which I had purchas
ed for her – down around the shaft and head of my cock, and jerked energetically on my penis as I imagined it melting away, shrinking back up into the base of an otherwise smooth, sloping, wide-and-round-hipped feminine pelvis – the kind that I could only allow myself to imagine having in fantasy moments like these – until with a loud, lengthy groan I felt my cock finally spurt my kinky obsession all over the satin and lace material in my hands.
I cleaned up the ‘mess’ that I had made just as soon as I came down from that massive orgasm. The shame that I felt was intense that day. There was, of course, the fact that I’d given into my soft, effeminate, emasculating desires again, that I’d let myself fantasize about trading my masculinity away, that I’d cum to a vision of my cock melting away, being replaced by a soft, beautifully feminine womanhood, a receptive, penetrable expression of the gender that I longed to, ached to become in my fantasies of late. That I’d let those fantasies once more make an… imaginary woman out of me. But even worse than all that, I’d let my fantasies get so out of hand, let my urges get so strong, that I’d ruined one of the pretty nightgowns that I’d purchased for my new lover. There was no way I could return this nightgown to Jade now, not after I’d used it as a cum rag for my own feminization fantasies. Even if I washed it, it would still be the chemise that I’d used to help get myself off to fantasies of becoming a woman just like Jade, and here I was supposed to be the man that she fucked, the man that made her feel like a beautiful, desirable woman, the man who – well, a man!
