Man to Woman

by Jane Futa

  I squinted as I grabbed the tiny denim shorts in my fist and inspected them. How the hell did they end up back in my trunk? My tight expression of confusion broke into a smile as I shook my head and laughed. I recalled when my friend climbed into the passenger seat of my car that night. I had sworn he was a hot chick getting into my car – that was a nice two seconds. He laughed and said, “ta-da!” with outstretched arms, as if some game-show eye-candy displaying a washing machine that the contestant could take home if they won.

  “You’re kidding me, dude,” I laughed.

  “Holy shit, Jason - you really thought I was a girl, didn’t you?” Bryan smiled.

  “What?” I shrugged, and compulsively adjusted the rear-view mirror. “No way,” I dismissed.

  Are you fucking kidding me, I thought to myself as I snuck glances over toward him during the ride when he was scrolling through his phone. I had no idea that a guy like him could just transform so indiscernibly into a hot chick. If I hadn’t known it was him – if I had seen him at a bar or a party – I totally would have hit on him. The weirdest part was that, I still kind of wanted to; even though I knew full well it was him. The weird thoughts and feelings might have had something to do with eh amount I went on to drink that night – and for good measure. I hadn’t really thought of that night until the remnants were staring me down from the trunk of my car. I was alone in the desert with that skimpy little outfit.

  I grabbed the thin blue cotton fabric of the camisole and held it up against my chest, as if I were trying it on. I quickly thrust it back into the trunk as I saw a car come barreling down the highway. As it neared, I saw two dudes about my age, decked out in sunglasses and baseball caps, careening their sports car right down the road, ready to pass me by at any second.

  I jumped from the trunk of my car and toward the shoulder of the road, waving my arms and with a hopeful expression, tried to make eye contact as best as I could. I was all alone in the desert. Maybe if I were near civilization their conscience would let them ignore me, but surely they would help me out even if just by making a phone call.

  “Hey!” I yelled, when I saw them start to slow down and roll their window down.

  The guy in the passenger seat gave a half-smile through a strong jawline and said, “Car problems?” as the car came to an idle for a moment.

  “Yeah. Dude, am I glad you stopped. Do you guys think you could help me?” I said, nearing their car.

  Both guys looked at each other before the driver leaned toward the passenger side to see me hanging over the window and said, “There’s not really anything we can do. Sorry bro.”

  My expression turned stone-faced with shock. “Dude, I’m all out here by myself. Can I just use your phone or something? Or like, could I just ride with you guys to the nearest gas station? Maybe I could call somebody there.”

  “Oh, um,” he started, fumbling over his words. The car started to inch forward slowly as he continued. “We’re um… we just can’t, bro. Sorry bro.” Suddenly the back tired spun and I pulled back from the window, only to watch my only hope for rescue speed off down the road.

  “Fucking pricks!” I shouted and dug my shoe into the sand. I looked over to see a lizard eyeing me passively, before dragging its belly across the road, lazy and uncaring.

  Whatever, I thought to myself. That’s fine. It didn’t take too long for somebody to show up, maybe somebody else will come by.

  And in fact, only a few moments later, a pickup truck came down the road. But the guy inside only gave a half look toward me and without so much as slowing down, sped right past my desperation.

  Every car that passed by had been commandeered by some uncaring male asshole who seemed to have a million better things to do than help another guy in need. I balled my fists and sat back against the trunk. The opened door provided more shade than anywhere else. And again, I saw the girl’s clothes. Somehow, even in the middle of total defeat and frustration, I couldn’t stop imagining my friend dressed in the clothes. This is the last place I need to be thinking about that, I thought to myself.

  I tried to grab the clothes and put them in a small backpack that I’d left in my trunk, to put them out of my sight, when I noticed a thong just under the shorts and cami. My cock swelled at the sight of the lacey white thing. I picked it up and studied it. Bryan had gone all-in, apparently, even leaving a pair of open-toed shoes and his makeup in the trunk.

  If my problem needed to pose as a girl, I’d have everything I needed; I thought to myself and laughed. Too bad my problem is a piece of shit car.

  “I’ll bet those assholes would’ve helped Bryan if he’d been dressed in all of this. They would have tripped over themselves to help him out.”

  I shook my head in frustration, until the forbidden thought crossed my mind. No way, I thought to myself in response. There is no way I could pull that off… is there?

  Bryan had been the exact same build as me. And when I held the clothes up against my body, they seemed as though they would fit me just as seamlessly as they had fit him. But what was I going to do? Dress as some hot girl and flirt with a guy to get his help? There was no way I could do anything like that. The thought alone left me falling over laughing beside my useless car. But then, the longer I thought of it, I had to admit it sounded just the teensiest bit exciting – if for no other reason than to get a rush of justice in a world where guys were so driven by their cocks that they wouldn’t help anybody who they couldn’t fuck.

  And I started to wonder, if I had been in the position of the people passing me by on the road, would I have stopped either? It was something I wanted to believe I would do the right thing in, but I had no idea, to be completely honest. And regardless, as car after car of disinterested men passed by, I grew more frustrated and more desperate. The late afternoon sun started sinking toward the mountains, and I knew that once they hit the edge and ducked below them, things were going to start to get much more desperate.

  So I walked back toward the trunk and, with a speeding heart and short breath, I clutched the thong on my hand. I bit my lip and looked both ways, to make sure I was just as alone as I’d felt all afternoon. After all, the moment I stripped down naked would probably be the moment a tour bus or rescue helicopter would conveniently make an appearance.

  The coast was clear, and so I unbuckled my jeans and when the denim loosened around my thighs, I started to tug them off, along with my boxers. The thrill of feeling the desert air against my bottomless body became immediately palpable. I loved it. It was liberating, and just a bit naughty. I’d never known myself to be the sort of guy to like danger or excitement in that way, but the thrill of being naked in that moment left me clawing for the thong and ready to take a full dive into the risk of my life.

  I bent down and stuck my feet through the loops of the white cotton thong, and pulled it up toward my body. Inch by inch up my legs, the fabric neared my manhood, until the next thing I knew; the girly underwear was pouching my cock and balls snugly. They weren’t very big, which in this wildly specific situation actually helped my cause, I guess. I looked down and saw the small bulge in the cotton thong, and immediately started to wonder who the hell I was… or was becoming.

  I grabbed the little denim shorts and tugged them up my thighs next. They were tight, but they fit well enough, and as I stepped back to look at my faint reflection in the backseat window of my car, I couldn’t help but admire my own ass; it was cute and perky – more than I had ever realized.

  “Damn,” I whispered with surprise. If somebody had taken a picture of my ass right then, without my knowledge, and then had shown it to me? Well, I would have probably wanted to fuck whatever girl was in the photograph. The feelings that came from that realization were naturally, just a little bit conflicting. I wasn’t gay, and I had never been interested in wearing girl’s clothes. But something overtook me right then in the desert. My little act would be purely functional, but also seemed to serve as a test to see just what was hiding in beneath the de
epest waters of my sexuality.

  I had been ready to jump Bryan’s bones on Halloween, after all. I never would have told him that, but I had immediately convinced myself that it was okay so long as he looked like a girl. And as if that night were coming right back to me, I started to actually convince myself that it would be fine if I had to flirt a little more than usual, or even offer some sort of sexual compensation, because I would be a girl when I did it – a hot one with a damn nice ass, at that.

  I knew Bryan had had a bra that night – he complained about it strangling his chest during the entire ride over. Yet, it was nowhere to be seen in the trunk. I wondered if the act was suddenly over before it had even launched from the ground. I decided to put on the camisole anyway, and as I dropped it over my bare chest, I was unsure. It wasn’t until I fit the long, blonde wig on my head that I suddenly became convinced. I looked at my reflection in the mirror and couldn’t see myself, no matter how hard I tried. I saw a cute, skinny, albeit flat-chested girl. It didn’t matter that I was maybe hiding a pair of A-cups under my cami – I was cute enough to pull it off. Well, at least I hoped I would be. I was still shaking my head with disbelief the entire time I sat in the driver side seat of my car and tried to manage a bit of eye-shadow and blush while balancing my face in front of the dingy rear-view mirror.

  I still had an impossible time believing that anybody was going to buy it. Sure, the moment their car came over the horizon and I was still several yards away, they would undeniable see a young woman stranded in the desert, but what about when they slowed down nearby?

  I looked at myself in the reflection of the window one more time. I couldn’t tell whether I’d done a decent job of the makeup, or a horrible one, to be honest. I could only go on my own judgment of whether I would have made a move on myself if I had seen myself at a party. I decided that I definitely would have, but that didn’t mean much compared to anybody else. I was practically a nineteen year-old virgin, anyway, so I wasn’t exactly picky with girls. This had particularly stung when during that drive to the Halloween party, Bryan and his friends had asked why I hadn’t joined them dressing in drag.

  “Why would I?” I had said with nervous laughter, gripping the steering wheel.

  “I don’t know, it just seemed kind of natural,” Bryan said with a guffaw.

  “Huh,” I said, before trying not to think much of it and turning the car stereo up slightly.

  “I just mean… I don’t know… you’re such a pretty boy, honey, everybody thinks so,” one of Bryan’s friends said, in a girlish tone as he batted his glue-on eyelashes.

  “Fuck you guys,” I said, rolling my eyes. I filed the remark away with the rest of the missteps that night, and was lucky to forget about it for so long. But now, the thoughts, the doubts and the mixed emotions returned as I looked myself over in the window and a hot girl looked right back at me.

  “Maybe I should just fuck myself, and then I won’t be a virgin anymore,” I laughed. The thought made me tense, though, in a way I hadn’t felt in a very long time. “Too bad my dick isn’t long enough – I could just fuck my own ass and be done with it.”

  Aside from the hilarity of that imagery, I was suddenly imagining a cock – other than my own; big and thick and powerful, driving right into the very ass I had just been admiring in the car window reflection. I imagined myself bent over the hood of my car, with some savoir mechanic pressed behind me and lining up his massive, chiseled cock, ready to shove it deep inside my tight, virgin ass. And suddenly my own cock started to flare. I wasn’t ready to admit just how hot this made me, despite the rock-hard cock now forming a tent in my thong. I shook my head and with denial, tried to place myself in the mechanic’s spot in my fantasy. I’m the mechanic fucking some damsel in distress… hot… I thought to myself.

  Only, my cock started to go limp again, until the thought came rushing back in, with some beefy, muscular jock grabbing my ass and pulling it down over his thick cock, splitting me open. My ass pulsed and my ball sack tightened with anticipation. I didn’t know, or at least didn’t want to admit it, but I craved that very thing. I wasn’t about to admit it – not in a million years. I decided that a little bit of small talk in my best girlish voice ought to be enough to score me a ride to a nearby gas-station, and then I could give the guy a fake phone number or something. That was the plan, at least. I wasn’t about to let myself be violated by some big, nasty strange guy, after all.

  “Shit,” I blurted. In the rear view mirror, I saw not just a truck coming up from behind me, but a tow-truck. It was as if my most specific prayers had been suddenly answered. I wondered if somebody had called a tow truck for me. It seemed unlikely, but who knew.

  As the dingy, beat-up old tow-truck came down the road like a white beast scouring the desert landscape, I stood outside of my car and propped myself up so that I jut my hips out a bit and crossed my legs; it probably looked hopelessly over the top, but it was my very first and very clumsy time of trying to mimic the sort of natural grace that so many girls are born with.

  The truck came closer and closer, and I just hoped that whoever was behind the steering wheel was even somewhat attractive. Out here in the middle of nowhere, though, it seemed like impossible odds.

  My blonde wig danced lazily in the late desert breeze, and my cami flapped a bit at the hem, but I felt comfortable enough to make a go of it. I cleared my throat and as the truck grew ever closer I said, “Um, hi,” in my best feminine tone.

  “I’m so lost!” I continued, frowning helplessly. “Won’t you please help me? I would do anything.”

  The truck neared closer, still, but the dusty glare of the windshield made it impossible to see who was driving, until they slowed near my car, as so many others had done that afternoon. But this time, I was a hot girl and my heart thudded with anticipation and anxiety to see just how I was treated this time around.

  The passenger side window started to roll down, and as I was met with the driver, I breathed a sigh of relief. The driver was a younger guy, maybe five or ten years older than me. He had short but unkempt greasy dark hair, and a medium sized build. His eyes were small and pale, and his skin was rough. He wasn’t prince charming, but he wasn’t awful to look at, either. In fact, he seemed like the sort of guy who might fall head over heels for a girl like me – I mean the sort of girl that I was dressed as.

  Obviously I’m not a girl, I thought to myself, laughing at my mistake. At least, I still seemed to think that I wasn’t.

  “Howdy,” the young man yelled over the diesel engine that left the entire front end of his truck rumbling quietly.

  His smile told me everything I needed to know about my odds – they seemed good. He had that very same indulgent grin that any guy got when they thought they had a chance with a girl who was out of their league. Not that I was so conceited as to believe I was a particularly hot girl. Ok, I did think that I looked super cute. But it was more like, I felt more comfortable and confident dressed as girl, than I had ever felt as a guy. I felt sexy the moment I saw myself dressed as this lonely girl in the desert. I was turned on by the sight, but what I was having trouble deducing, was whether I was turned on by the sight of the girl, or turned on by the realization that I was a girl.

  The moment I opened my mouth, it became evident.

  “Oh my gosh! I’m so glad you stopped,” I said in a high-pitched tone. I teased my blonde hair in my finger and smiled, batting my eyes. I didn’t want to seem like I was filming a porno or anything, but I knew I needed to come off as inviting and desperate as possible. I wanted to get out of that fucking desert, already.

  “Car troubles, huh?” The man asked, shaking his head and squinting. “Pretty bad place for that.”

  “You’re telling me,” I said with a giggle.

  “Is there any way that I could use a phone or maybe… I don’t know…” I started, before turning my eyes down to my feet and fidgeting my fingers together.

  “You need a lift?” He asked.


  What a surprise. I’ll bet this horn-dog would have driven right past me when I was a guy, I thought to myself with a touch of bitterness.

  “Are you serious? That would be, like, so amazing. You’d be my knight in shining armor!” I said with a laugh.

  “It’s about thirty minutes to the nearest town. I’m going there right now, so why don’t you come along. In fact let’s just take your car down there, too. I’ll take it to this mechanic who’ll get you fixed up.”

  The man smiled at my glee and started from the truck. Much to my surprise, he didn’t seem too interested in flirting or hinting toward anything sleazy. Had I actually come across a man who simply wanted to do the chivalrous thing? I couldn’t believe my luck.

  I watched hopelessly from the passenger seat of his truck as he hooked up my car. My smooth, bare thighs chilled against the cool leather seats. It felt so damn good to be in an air-conditioned space again. I exhaled and relaxed for a moment, until I saw him finish hooking my car up. I tensed up a bit as he opened his door and hopped back in. I now had a thirty minute performance to pull off as the hot girl that I appeared to be. If he sensed anything weird, he might just drop me off halfway to town with an angry scowl across his face.

  “How long you been out here?” He asked, as the front end of the truck jerked wildly and we started back on the road.

  “Um,” I yelped. “I don’t know. What time is it?”