Addicted to Womanhood 1

by Zoe Brown

  “Oh, shut up, Ashton,” the beautiful woman lying beside me moaned, reaching out to me with both hands and pulling me by the wrists over and on top of her yet again, “And show me again how you do that… that thing you do with your cock, that one thing that made me scream…”

  “Mmmm… yes, ma’am.”

  ✽✽✽

  I’d picked up Jade from the main entrance of the Eden’s Lounge at about five minutes after 2am, right about the time she was walking out the door, sauntering sexily atop her tall, black heels as she fended off some last-minute overtures from numerous lads and ladies who were hanging about the entrance as things inside the joint began winding down for the night. I pulled up alongside the red-carpet, velvet-rope-lined walk-way in the sleek, sexy, gently-thrumming European automobile that I’d promised the young woman I would deliver, to the shocked and staggered reactions of the various people milling about on the sidewalk outside, and slipped out of the driver’s seat, leaving it running as I stepped around the rear of the vehicle and took the beautiful young bartender by the hand, helping her down onto the street and into the driver’s side seat before I leapt into the passenger’s seat beside her. There were no more offers for the lovely lady’s company once I appeared – everyone lingering about outside hoping that the prettiest girl in the lounge would elect to go home with them at the end of the night seemed to feel that they were hopelessly outclassed once my Ferrari pulled up outside the entrance and the hot, handsome older driver (me) with the shockingly sexy good looks and soft, silver locks appeared. They all melted away as we buckled ourselves into our seats and revved the engine up again.

  Jade was ecstatic, nearly beside herself with giggling glee as she took the wheel of the expensive, souped-up automobile in her small, delicate feminine hands, and ran her fingertips reverently over the molded surfaces and fancy controls. “Oh, it’s absolutely beautiful,” she purred, wrapping her arms around the steering column and pressing her breasts into the wheel, “and it feels so…” she pressed down on the break and the accelerator simultaneously and laughed with delight as the thrumming vibrations of the powerful F140 V12 engine flexed and roared under her touch. “Ohhh, it’s so powerful!” She was basically cooing at the car.

  “You want to take her for a blast down highway 101 before we head back to my place?” I suggested to her as the engine idled away beneath us. Jade’s pretty face came up with a surprised, excited look on it, but there was some conflict in her eyes as well.

  “…You sure you’re okay with that?” She questioned me, carefully solicitous. “What if we get pulled over?”

  I smiled and shrugged. “You’re a beautiful woman and not the legal owner of the vehicle. I’m one of the richest men in the city and a prominent donor to many of the string-pulling politicians that run the place. We’ll be fine.”

  She returned my smile with a slightly muddled, worried-looking one of her own, but less than twenty-minutes later we were racing down the length of Highway 101, and the road was just flying away beneath us. The windows were down, the wind was in her hair, and Jade looked more on fire and alive than I had ever seen her before. “WOOOOOOOOOO!” She screamed, loudly, as the car blitzed past a hundred miles per hour and climbed steadily upwards towards a hundred and fifty. At this time of night, Highway 101 was relatively deserted, but Jade still had to slip around and between a few slower-moving vehicles now and again as we shot across the long length of the Golden Gate bridge and raced northwards. At one point, a couple of young studs wearing a significant amount of bling and riding in a modified import car with an automatic gearshift drew even with us as we rocketed up the highway, blowing kisses at Jade through the window and shouting suggestive come-ons at her, but with a shake of her head the smoking hot gearhead piloting the rocket beside me smirked, poured on the speed, pushing the hot Italian-made automobile way up beyond a hundred and fifty, and left the two young posers swallowing her dust.

  We raced as far north as San Rafael before Jade grinned over at me and let her foot off of the gas pedal, allowing the car to coast slowly to a lower speed. Leaning across the gearshift, the hot, sexy young street-racer-turned-sweetheart pressed her trembling lips against mine in a frantic, needy kiss, and then whispered, hoarsely, “I’m so wet I feel like I’m about to start swimming in my panties. If I pull this car over, will you please fuck me until my legs are shaking and I scream your name?”

  A hot shock of arousal pierced through me at her words, and I blew out a breath, kissing her back just as hungrily, “Ohhh, yes, yes, absolutely yes…”

  She pulled us off of the highway and into the empty parking lot of a Staples office supply store, parking in the shadow of some trees that screened us from passing cars. Then, pulling me bodily from the vehicle, she kicked off her heels, wriggled out of a pair of sexy, lace white thong panties (which were soaking wet, just as she’d said), and her black stockings, worked her leather skirt up around her waist, and then backed her full, round ass up onto the warm hood of the car, and had me take her right there, which I happily did. It was fucking fantastic. At the pinnacle of our mutual orgasms, I bent my head forward into her breasts and groaned her name even as she threw back her head and cried out “OHHHHHHH—! ASHTON! I LOVE BEING A WOMAN!”

  The return trip back into the city was less high-octane, but significantly more intimate. Jade took my hand as she skillfully steered us back into the city, cruising along at a far-less reckless speed of around 75 mph, shooting me the occasional flirty, furtive smile but otherwise observing a quiet, introspective silence as she wrestled with some conflict within herself. I let her have the silence, enjoying the intimacy and giving her the time to work out whatever she was grappling with, just as I was similarly grappling with a much more secretive conflict inside of myself. Although she had gotten back into her shoes for the drive back to the city, I’d carried Jade’s wet panties and discarded pantyhose back to the car once we recovered from our first sexual encountered on the hood of the car and was now holding them in my lap as we cruised back into San Fran. Beneath the pile of feminine clothing in my lap, my cock was hard – rock hard, and straining – and I kept wondering over and over what it would be like to be able to wear sexy, feminine clothing like this myself, with a body that designed for them and for the female role in the kind of hot, steamy male-on-female vaginally-penetrative sex that we’d just enjoyed and that I’d always loved. What would it be like to become a woman like Jade?

  Our hands were everywhere on each other’s bodies from the moment we parked the car in the underground lot beneath my building, and our lips were locked with one another’s for the duration of the elevator ride up to my penthouse at the top. We started tearing one another’s clothes off as soon as we made it inside the front door, and left a trail of high heels, a man’s suit jacket, a woman’s blouse, a man’s pants, a woman’s tight, faux-leather black skirt, a man’s undershirt and boxers, a woman’s bra, and a man’s pair of socks scattered across the floor of my apartment in a winding line that lead up into the loft above my living space, and right into my bed.

  As previously noted, we engaged in passionate sex two more times in that bed before we collapsed, spent, on top of and entangled with one another, into the comforting embrace of an unspeakably expensive mattress, and then a third time only a few minutes later after a couple moments of tender, flirtatious conversation. When we finally came and collapsed together again another fifteen or so minutes after that, panting side-by-side in the bed next to one another, we decided to call a halt to our sexual exertions for a little while so that we could both get something to eat. Jade pointed out that she’d been at work for the entire evening without having any opportunity to satiate her hunger, and I hadn’t eaten since grabbing a quick bite at the Y in the late afternoon.

  We both slipped downstairs into the living area of the penthouse. I delighted Jade with an unexpected present: a pair of expensive lingerie items that I’d picked up for her at Aricie’s European lingerie boutique – a Christie’s G
reta silk chemise and a matching silk sleep robe – while I was waiting for her to get off of work (a quick phone call to an already-occupied-but-willing-to-be-persuaded boutique manager and an offer of three-thousand-dollars for a ten minute look at her inventory had opened the closed shop for me), and then the two of us worked side by side in the kitchen – her in her new lingerie and me in an expensive pair of men’s satin pajamas – for a little over a half an hour, exchanging some small talk and whipping up some late-night chocolate frappés, a short stack of crêpes with some strawberries, whipped cream, and powdered sugar, and a pair of stove-grilled Kobe beef steaks.

  At a few minutes before four in the morning we opened up the balcony doors and curled up with our late-night dinner on one of the couches facing the city view, getting through our drinks and our fruit while the steaming hot steaks rested, and then pouring ourselves some delightfully smooth white wine and taking the first slow, tantalizing bites of the meat while we listened to the sounds of the city at night. Finally, once I’d had several bites of my steak and was relaxing with my wine, Jade leaning back against my chest as she took little nibbles out of the remaining strawberries and occasionally poked at the much-too-large cut of meat that I’d prepared for her, I got ready to bring up the questions that I’d been holding onto all evening.

  Chapter Ten

  “So, tell me,” I started, taking a deep breath and leaning down to kiss the top of Jade’s beautiful head, “how did a racing-obsessed street gearhead find his way into skirts, high heels, and the expensive beds of playboy millionaires?”

  “Only one playboy millionaire so far, as far as I know,” Jade corrected me with a quick smile and a twinkle in her eyes. “Couple of fairly ambitious up-and-comers who stood a shot of becoming millionaires here and there, but you’re the first bonafide rich guy that I’ve landed in the sack.” She glanced around herself with an appreciative smile and nodded. “I think I might have to shoot for this class of living more often in the future, though,” she glanced down at herself and the beautifully elegant lacey lingerie that she was wearing, poking at it with pleasure, “So far I like being pampered.”

  “Well, it’s certainly a pleasure pampering you,” I returned, sipping my wine and enjoying the sight of the way the lingerie hugged her sensuous curves. A small stab of envy went through me, though, in the middle of that pleasure. “But…”

  “But how did I go from proudly owning a stick-shift to riding them?” The pretty dark-haired girl finished my sentence in an… unexpected way, but she definitely knew what I was asking her. “Uhhhh, it’s kind of a long, and…” she winced, “not entirely pleasant story. You sure you wanna know?”

  “Absolutely,” I said, brushing the fingers of one of my hands down her right upper arm. “Even more intrigued now.”

  “Mmmmm, alright.” She still sounded reluctant, but she reached out to the table in front of her for her own glass of wine and took a hefty sip of it to steel herself, then dove right in without any further hesitation. “I grew up as Giuliano Giancola, inside of a small-scale mixed-ethnicity community in the Mission district. My mother was Mexican, my father was Italian, and they met in the sixties – free love and all that. I was the eldest of four children. My father, Dominick Giancola, was a soldier; he wasn’t around much when I was a kid and he died somewhere overseas when I was fifteen, but my mother, Rosalita, had a lot of brothers living around her in our neighborhood, so I grew up in a pretty intensely-masculine environment, and like most of the boys in my neighborhood, I got into cars, street-racing, and girls when I got older.

  “I never went to college or anything. By the time I got kicked out of high school, I already had a tiny rap sheet – running with the street racers while looking anything other than lily white meant getting picked up a time or two, and as we got older the guys running the races – including my uncles – would start to use us as lookouts or couriers for some underhanded shit, and that wasn’t great for my chances of staying out the way of the law. Not that I cared back then,” Jade took another drink of her wine and rolled her eyes, snorting at past self with derision, “I was infected with the idea that it was the height of masculinity to take stupid risks like that, to get in fights with other guys from other neighborhoods over whose turf this or that little street drag was, to try my hand at a little breaking and entering, stealing car parts and engine components out of auto shops all up and down the district so that the guys who ran our little racing crew would see me as one of the tough guys and so that girls would fawn all over me and melt into a little puddle before my dick.” She shook her head and sighed. “And the more I did it, the more trouble I got into, and the more macho I felt, so the more I risked.”

  “I had a best friend back then named Theo. He was a mixed-race guy, like me, though everyone always just looks at me and sees Italian or Latino. Theo’s father was Latin, but his mother was Vietnamese. I guess they met during the war, or something. They were a dysfunctional little family living down the block from me and my siblings while we were growing up, and after a couple of back-alley fist fights over who had the bigger metaphorical dick, Theo and I got to be friends and looked after each other as we started turning into adults. We both got kicked out of school at roughly the same time – Theo told me he was caught drinking in the bathroom, but I think he planned to get caught after I was expelled so that he wouldn’t have to go to school if I wasn’t going to be there.”

  “What’d you get expelled for?” I asked the beautiful young woman lying against my chest, trying with some difficulty to picture her as a rough, tough masculine street-punk growing up.

  “Ummm…” She blushed a little bit and sipped some more of her wine. “Stealing a computer from the school library?”

  I raised an eyebrow at that. She saw it, and laughed at herself. “Yeah, well, color me for stupid. I was seventeen, and trying to put together my first street racer. I didn’t realize, or I didn’t remember, or something… but there were cameras in the library, and I got caught on video tape sneaking the computer out through an open window so that I could fence it for the money I needed to get a part for my engine. My mother, the poor, poor woman, begged the school board not to have me charged with a crime, but they expelled me from school for that, and Theo wound up getting expelled a few days later.”

  “Sounds like a good friend,” I ventured, stroking her upper arm again.

  “Yeah, he was a good idiot, just like me.” She flashed me another smile, and then ran a small, delicate hand through her long hair, taking a deep breath again. “Anyway. So, I was really into cars, and racing, and putting together my first street racer, which took me a little longer than I’d imagined once I had to give back the cash from the computer I’d fenced, but I was also really interested in racing girls back then as well. You know, the super-hot girls with the big booties in the short shorts and the big boobs in the skimpy tops who lean into cars and have mouth sex with their boyfriends before the start of a race and who drop the flags at the starting line and form up along the road ways to cheer and bounce” she jiggled her own chest and laughed, “up and down as their guys fly by, racing down the strip at well over a hundred and fifty miles per hour?”

  I laughed as well, nodding my head. I did indeed know that type of girl. I’d slept with several over the years. They were quite the draw at the street races in Romania, Hungary, Brazil, and other places where I’d participated. They were rarely as vapid and silly as the men who frequently bedded them liked to pretend they were – in my experience, they were often quite clever, using their sexuality and their femininity as tools in leveraging themselves into a more advantageous and prosperous position within their social communities, riding shotgun alongside a moderately wealthy, successful street racer who could buy them nice clothes, fancy cars, and set them up for years if they were careful – and they frequently were. Plus, they got to enjoy a helluva lot of hot, steamy, smokin’ sex with someone who knew how to use his hands. It wasn’t usually a bad deal, unless they got trapp
ed in an abusive dynamic with an insecure douchebag who wouldn’t let them go.

  “Yeah, well, let’s just say I took something more than an average amount of interest in the ladies who hung out at the races with us,” Jade offered, wiggling her eyebrows at me. “I loved the racing girls. I loved hanging out with them, loved being around them, I loved having sex with them, I loved talking to them… any of this starting to sound familiar, babe?”

  I rolled my own eyes, turning my face away from the top of her head and having a couple more bites of my steak before sipping some more of the smooth wine. “I get it. We had that in common. Go on the with the story?”

  Jade grinned wickedly at me, but then she did as I asked, “So, like, the problem was, it wasn’t considered super manly for a guy like me to spend all his time hanging out with ladies, even if I was sleeping with a bunch of them, so I got ribbed on a lot for being less than macho and having ‘lady-feelings’ and stupid stuff like that,” she waved a hand, airily. “I got called a bunch of names, and accused of being gay, so I had to prove my manhood in other, more… assertive and violent ways. I got in a lot of fights back then, in the late Oh-Ohs, defending my manhood, and ‘our turf,’ against a bunch of other local neighborhood crews that kept crowding in on our little community. And the cops, now and again. I wound up in the hospital more than once, and I sent plenty of guys to the waiting room looking to get stitched up.”

  Jade took a slow, shaky breath, sipping some more of her wine for a moment as she tried to calm herself. “Looking back now, I’m not super proud of who I was then. It might be part of the reason why it’s been so easy for me to shed his identity and move on with my life, as Jade.”