Man to Woman

by Jane Futa

  “I can’t,” I said, pulling back.

  “What’s wrong?” He asked, setting on the edge of the bed.

  “You would never forgive me if I told you – trust me,” I said, sitting beside him. “I’m not really what you think I am,” I continued, expecting to be shot at any moment.

  Why didn’t I just come clean before he kissed me? I thought.

  “What do you mean?” he asked.

  “Do you think I’m like, some hot chick, or whatever?” I asked.

  “Yeah, I do,” he said with a grin.

  “Um, well, I’m not entirely a girl,” I said, hoping that this would get the point across well enough.

  “What do you mean?” He asked, furrowing his brow.

  “Um, well, I have something most girls don’t have,” I said, drawing my eyes down toward my jean shorts.

  “I’m not really following,” he said.

  “Ugh,” I strained, shaking my head. “This is so ridiculous. Um, I don’t have a pussy… I have a… you know… because I’m not entirely a chick,” I said, struggling.

  “Funny,” he said. “You look like a really hot girl, and you feel like a really hot girl.” Fred put his hands on my bare thighs, along the tops, and started toward my ear as he continued, whispering. “You taste like a girl, and I’ll bet those lips suck just like a girl, too, don’t they?”

  I said nothing, and instead I only felt my body aching with desire as his warm breath pushed against my cheek.

  “It would be a shame to find out that I brought a guy back here to my bed. But so long as you look and act like this gorgeous girl, I have no reason to think that. I guess the question is, what are you going to do to convince me you’re the hot girl I thought you were when you walked up to my garage?”

  “Well,” I said, hesitantly. “I don’t know,” I bit my lip, and drew my hand down along the inside of his thigh. I had no idea what he wanted at this point – did he still want me? Was he seriously fine with my little secret? There would be only one way to find out. Now that my confession was out in the open, I only had one saving grace – to be the hot girl I wanted to be, and the more convincing I could be, the better, apparently.

  So, I came down on my knees, between Fred’s legs, and looked up toward him with a quiet, curious expression, as my hands ran along the inside of his thighs. “I don’t know a hot girl in town who doesn’t suck the first dick she gets her hands on,” he hinted.

  “And you’re a hot girl, so I imagine you’re the same way, huh?” He asked.

  “I am,” I said, biting my lip as I eyed down toward the mound in Fred’s uniform.

  I wanted nothing more than to taste his cock on my mouth. I didn’t know what. I didn’t know what was wrong with me, or what had happened to the straight guy I was only hours before, but I didn’t care. The only thing I cared about was being the sexiest version of myself, which just so happened to be sitting on her knees in that dark bedroom, with a stud before her, unzipping his pants.

  The breath was stole from my lungs as his pants loosened and he pushed them down, along with his boxers, letting his massive cock spring out – fat and tanned with a chiseled, helmeted head sitting atop it and a set of equally heavy balls just beneath it. I couldn’t believe it. I didn’t know if it was simply the perspective – I’d never been this close to a cock before – face to face. But as I nervously brought my hand against it, wrapping my fingers around the pulsing, soft warmth, I realized just how giant it was.

  How am I going to fit this in my mouth, I suddenly thought with a shot of fear.

  I started to stroke the fat cock and watched with immediate addiction as Fred’s eyes fell slightly and he sighed with delight, before letting himself recline over the edge of the bed. I stroked firm and intent, but tried to remain calm and patient. I watched as my hand stroked up and down his shaft, and tried to comprehend that I was actually stroking another man’s cock. Yet, it didn’t feel like I was stroking another man’s cock. Rather, I was a girl, stroking a guy’s cock. There was only one male in that bedroom, as far as I felt in that moment. And I wanted to make him feel that very way.

  I felt Fred’s hand against my cheek as he turned his eyes toward mine and whispered, “Why don’t you show me what those lips can do?”

  I took a deep breath and looked at the massive cockhead only a foot from my mouth. This was it. I parted my lips and brought my mouth ever closer, until before I knew it, the clean, salty cock was filling my mouth and stretching my lips with its thickness.

  I stuck my tongue out and my lips stretched around his girth, as I sank as deep as I could and pulled back. My own cock flared with hardness as Fred’s moans set me ablaze with arousal. I loved every delighted sound he ejected – I wanted to hear him moan louder and louder, until he was under my total spell. I wanted to feel his addiction for my body, and driven by that, I worked my mouth into a rhythm and brushed my tongue against his cockhead before driving his shaft toward my throat, until I could barely stand it, and I pulled back.

  “Fuck yes,” he moaned, grabbing my wig and gently forcing my mouth down even more. I didn’t know if I could handle it, but the thrill only made me more desperate for his domination.

  I grabbed the base of his cock and stroked as I continued to suck. I couldn’t believe women could be so good at such an act – I felt as though I must’ve been terrible, but he seemed to enjoy it. I reached down and felt his heavy balls in my hand – they felt like sheer power. If he could have felt my own small equipment, he would have laughed at just how irrelevant it was, which made perfect sense, now. I was his girl, and every sound he made only confirmed it more, even though I didn’t know what I was getting myself into with every suck I gave around his cock.

  I gave one final, deep thrust of my mouth over his cock until I nearly gagged, and I felt him tense. “I want to make you cum,” I gasped as I pulled back and stroked his cock.

  “Oh, you’re going to, but not there,” he said, pulling up from the bed.

  “What? Then where?” I asked.

  “Well, you’ve got such a perfect little butt – it would be a shame not to fuck it,” he growled.

  “You want my ass?” I asked. The thought alone worried me, but it made my cock harder than ever. The thought of being dominated in that way left me so weak I thought I was going to faint. I loved the idea and bit my lip hard, even though I was nervous as hell.

  Fred reached down and grabbed my ass, before pulling me up and pushing me down over the bed, until I landed on my stomach with my butt in the air, fully on display for him and ready for taking, just like the hot little slut I had become. The cool sheets brushed against my body and left me exhaling with bliss as I anticipated him coming up behind me. I didn’t know when it would happen, until I suddenly felt his strong hands yanking my shorts right down.

  “Oh!” I yelped as I suddenly felt my bare ass against the cool air of his bedroom. I was now exposed for him. The paltry, small thong was now the only thing hiding my ass, and its tiny string left nothing to the imagination.

  “Fuck,” Fred groaned before coming down and planting a kiss against my ass. His soft, warm lips against my skin sent a thrill up my body.

  Am I seriously about to do this? Am I going to get fucked by a guy? The thought was almost too much to handle, but my body wanted it more than anything. I couldn’t believe myself, but I wasn’t going to stop – I wasn’t going to give in to any reservations. I was in the middle of nowhere – I was a stranger. I could be whoever I wanted to be, and now I was Melissa. And Melissa wanted Fred deep inside her.

  I sighed as I felt Fred’s fingers dig into my ass cheek and grab firmly, before pulling back and giving a hard spank. “Oh!” I jumped, pushing my ass higher into the air.

  I suddenly felt his fingers grab the string of my thong and pull it to the side, before he licked his finger and dragged it over my ass. “Oh fuck,” I cried, as his finger tip circled my opening like a shark circling its prey.

  “I knew you were
a dirty little slut. You were so worried that you weren’t woman enough for me. I think you’re going to fuck better than all the other hot girls I’ve had,” Fred groaned, before sinking his finger just inside me.

  As he broke me open, I felt the slight bruise and I bit my lip and groaned into his clean bed-sheets. The scent of them mixed with the scent of Fred’s musk, leaving my senses dizzy under his spell as I turned back to see his shirtless body. He’d stripped, and standing just behind my ass was all muscle – ridges and mounds of pure strength, flexing and hungry to take the perky little as I’d admired in my car window’s reflection. I wasn’t the only one who’d decided they would happily fuck my ass.

  Fred’s slid his finger deeper, delighted as I cried out. “You like that?” He asked.

  “It’s so big,” I wailed in my high-pitched tone.

  “Girl, you’re in trouble if this is too big,” he laughed and gave me another spank.

  “I’ve got something else that might be a little bigger, but you’re going to love it once you adjust,” he said, and I suddenly felt his cockhead spanking against my asshole.

  Fuck, can I handle this? I thought to myself. But it didn’t matter. I would handle it, because I wanted it, and I wanted to hear the sound of the stud mechanic cumming deep inside me. I wanted to know what it felt like to make a man feel pure ecstasy. I knew I would be the hottest girl in town the moment I left Fred empty and exhausted.

  His mouth suddenly came down over my ass, rimming and brushing his tongue around and around, leaving me squirming and writhing my legs uncontrollably. Luckily his strong hands held me in place, like a prisoner of pleasure.

  “Your pussy is so tight,” he said excitedly as he slid two fingers into me.

  “I want it to be tight for you, babe,” I breathed.

  I turned back to see Fred lathering his thick, hard shaft with a few drops of lube, before I felt the cold sensation of him sliding a small amount of it over my opening. This was it. There would be no turning back. My incredible, couple-hour transformation from college guy to slutty college girl, was about to be consummated with what would probably be the biggest dick I ever had, even if I continued my new identity forever.

  I winced as I felt Fred’s cockhead press against my opening. “Relax,” he said, as if I could even do that in the moment.

  And it didn’t matter. He broke me open anyway. I suddenly stretched around him and the wild soreness overtook my core as his thick cock forced its way inside my tight little backdoor pussy. I reached down and grabbed my cock and balls, pulled them as far forward as I could, so that there was no hint of my manhood. From Fred’s view, there was only a pussy covered by part of my thong. I was a certified girl getting her anal virginity stolen away.

  “Fuck!” I cried out, gripping the sheets as his cock continued to split me open, inch by inch as it sank inside and headed toward my deepest point. I couldn’t believe the sensation of being so full; being so stuffed with a warm, hard cock. I felt that I immediately knew what that indescribable sensation was that women would simply smile at when they talked about big dicks. I felt me entire body stretched open and stuffed by his thickness, and after only a moment, the pain subsided and I was left with a pleasing tickle that quickly swelled in my body and left me feeling as though I was going to cum at any moment.

  Fred pulled back and just as his cock slid out slightly, I pushed my ass back. I was too addicted to the sensation – I wanted him to fuck me hard, already.

  “I don’t need you to be gentle,” I whispered. And with that signal, Fred grabbed my ass and I was his. I felt his cock thrust in and out wildly, each time leaving me a desperate mess – wanting him deeper and harder.

  I suddenly realized he must’ve been pressing against my p-spot. Each time he did, the pressure inside me built and I smiled harder and harder, clenching my teeth as I screamed through them with ecstasy and exhilaration. Fred’s moans and breath grew heavier and heavier as he pounded my tight little female ass, and I wanted more than anything for him to cum as deep inside me as he could. For one brief moment, I even forgot that he couldn’t impregnate me. I even wished that he could have. I felt like his. He’d been a stranger, but in that moment, he was everything my life had been leading toward. He was the signal of a new purpose in my life. And I wanted the experience to match the feeling I had deep inside – for every moment of blissful transformation I harbored in my mind, I wanted him to fuck me that much harder, as if to confirm in reality what I felt in my mind.

  “Fuck,” he groaned. “I’m going to cum soon,” he said, after fucking my steadily and grabbing my ass.

  “Cum for me babe,” I moaned in my high-pitched exasperation. As I said this, I cried out and felt my own cock pumping rope after rope of warm cum against my thong. I hadn’t so much as touched myself the entire time, but Fred’s cock had pounded my ass right into orgasm – I couldn’t believe I could feel like such a woman.

  “Deep inside me,” I cried out, through the hazy, dark euphoria of my mind. I could barely speak coherently enough for him to understand. But I knew all too well when I heard him groan louder and lower than ever.

  And I swore I felt deep inside as the warm load of his virile seed filled my ass. Suddenly I felt completely, entirely like the woman I found myself wanting to be that afternoon. I didn’t understand it, and I knew that I probably never would. But the moment I put on those clothes, it became more than a ploy to get out of a desperate situation. It was like finding myself, when I didn’t even know I was lost.

  And now, with Fred’s cock deep inside me, pulsing as he groaned and strained, I could only smile and laugh with sheer ecstasy. I was a certified “hot girl,” and there would be no going back.

  “Fuck,” Fred exhaled, and withdrew his thick shaft from my tight canal. I felt the void immediately, and was somewhat sad – another sign of my true identity. He fell next to me on the bed and cradled me in his biceps, warm and sheened with light sweat. I was surrounded by his masculinity. I couldn’t believe what had happened that afternoon.

  “So, you’re staying in town for a while, huh?” He said.

  “Well, I’m on my way to…” I started, before biting my lip. “Yeah, I was… I mean, if you’d have me for a ‘little while’,” I clarified with a little giggle.

  “I’ll have you again and again,” Fred said with a cocky grin.

  “Then take me – I’m all yours,” I said, teasing the blonde locks of my wig. I was lost, desperate and stranded no more.

  I seemed to have found exactly where I was headed all along, and I smiled.

  PUNISHED BY THE COWGIRL

  Derek rubbed the back of his neck as the summer heat stung his skin. He peered down the long dirt driveway, which led to the ranch where he would spend the next month helping out for some extra cash. He wasn’t exactly made for country life, having grown up in the city. But now he was a broke college student, and short of singing up to pole dance at the local gay strip club, his best bet was answering an online ad for some extra help as a ranch hand.

  “Shit,” he exhaled, looking around the picturesque hillside. The emerald mounds extended forever, meeting the bold blue sky in the horizon. A slight breeze tunneled over the grass and left him with a sense of temporary relief.

  Derek unbuttoned his shirt and strapped it around his waist, letting his topless muscles breath in the nice, cool wind. The sweat that sheened over his pores brought a cooling sensation through his core, as he tied the long sleeves of his flannel into a knot just above his crotch. He looked around and hoped he’d ended up in the right place. The address was right, but the area almost seemed abandoned, save for a small ranch house up the path.

  Not wanting to get shot or mistaken as a trespasser, he kicked the dirt at the entry and waited around until an old red pickup truck crawled past the broken gate. He felt a sense of relief and dread as the dusty windshield revealed the roughened face of an older man. The man pulled up and stopped, hanging out of the rolled-down window.


  “You wouldn’t happen to be Derek Mooreland, would ya’?” The old man howled out.

  “Yeah,” Derek said, before correcting himself. “I mean, yes sir.”

  The old man laughed and shook his head. “No need for any of that formality crap, son.”

  “Come on,” he said, waving his hand. “We’re just down the drive a-ways.”

  Derek came around to the passenger side of the truck and saw inside. The man’s blue eyes radiated from his wrinkled, leathery face. He was rough around the edges, but held a sort of warmth in his expressions. Derek couldn’t help but feel a bit trusting of the stranger, and hoped that if this was his new boss, he would be as kind as they come.

  “Not there,” the old man called as the dust swelled around his truck.

  Coughing and covering his face, Derek asked, “What?”

  “Back in the bed,” the old man motioned with a laugh of disbelief. It seemed as if it was commonly-held knowledge that one road in the bed of the pickup truck and not the passenger seat. Derek swallowed hard and jumped into the back, holding on for dear life as he did something he’d never done before.

  There’s no way this can be safe, he thought to himself as his ass bumped up and down with every pothole the old truck drove over on its way to the farm house.

  After five minutes that couldn’t have passed soon enough, the truck came to a halt. Derek looked around, noticing the same small farm house up close, along with a windmill and a weather vane. Behind the house was another building, along with a giant barn surrounded by several horses and men.

  “Home sweet home,” the man called as he crawled from the truck and slammed the old metal door shut.

  Derek re-tightened his shirt around his waist as he climbed down from the bed, stepping into the soft dirt of the road.