Man to Woman

by Jane Futa

  “Woo,” Rachel shouted. “We’ve got a stripper here.

  Sam quickly bellowed out, “Show us!”

  “Show you what?” Derek asked, cocking his brow.

  “Strip for us,” Sam said with an excited smile. “I mean, I’ve already seen it all, but these ladies haven’t.”

  “Um… no way,” Derek said, self-conscious of his lean and less-than hulking body.

  “Ahem,” Sam said, clearing her throat. “I’m your boss, and I’m ordering you to strip.”

  Derek couldn’t help but feel intimidated by this. And yet the power play left him hard in his shorts. He didn’t know what Sam was all about. From the first day he’d arrived at the farm, she had been a complete riddle to him. She was wild but strict, careless but obsessed. Everything she said and did, seemed to be a contradiction. This was certainly no different. Derek looked around as the breeze worked through his loose shirt.

  “This is ridiculous,” he dismissed, waving his hand.

  “Come on!” Rachel shouted, with the girls joining in.

  “What do I get in return?” Derek asked, laughing and loosening up.

  “I’ll make it worth your while,” Sam said with a devilish grin.

  “What’s that supposed to mean?” Derek asked.

  “It’s a secret; just trust me,” she said.

  “The other guys aren’t going to pop out of the corn field or anything, are they?” Derek asked, overcome with a sudden suspicion that he was being pranked.

  “Fuck them – they’re no fun,” Rachel said. “They’re too busy trying to out-man each other,” Megan said with a laugh.

  “Come on already,” Sam said, egging Derek on. He stood there, his breath short and his heart racing as he balled his fists and tried to feel the sensation in his hands. His head was light and he couldn’t believe what he was about to do, but he was about to do it. There was no longer any question about that.

  Derek slid his tongue to the corner of his mouth and grinned as he started to unbutton his shirt, one button at a time. What was at first awkward and slow, worked into a proper rhythm at Sam’s insistence.

  “You call that stripping?” Sam yelled. “Move those hips. Shake that ass!”

  The girls laughed as Derek obeyed and continued unbuttoning his shirt, all while swaying his hips. He felt like a woman in that moment, oddly enough. Rather than a man stripping for four beautiful women, he suddenly felt as though he were the woman and the girls were boisterous famer boys watching him and whistling in approval. He didn’t know what to think, and his mind became somewhat hazy, especially when Rachel brought out her phone and started to play a country song, blasting it from the tiny speakers as the girls laughed.

  Derek swayed his hips and unbuttoned the last of his shirt, letting it fall behind him as his lean torso and chest was revealed in front of the warm fire. His sinewy muscles tensed as he slowly undid his shorts. Each of the girls cat-called and whistled, as Sam simply watched in complete satisfaction. Derek didn’t know what she could possibly be gaining from the experience; after all, girls weren’t supposed to be the raucous ones, eh thought. Girls were proper and reserved, and the last thing they would want to see was a guy as skinny and lanky as Derek, stripping in front of them. Everything he knew was quickly getting turned on its head that evening.

  With one quick yank, he unzipped his shorts and let them fall. He stepped out of them until he was only in his boxers, and his boots. Upon Sam’s urging, he kept his boots on, and swung his hips around wide as the girls whistled.

  “Take it off!” Rachel called as the others joined in.

  “Come on, show us that dick!” Megan said as the other girls looked at her with shock. Sam pushed her playfully and nodded in agreement.

  Fuck… no time like the present, Derek thought. In one swift motion he turned away from them and yanked his boxers down. The girls whistled as his ass flashed before them, perky and tight, and he tossed the boxers to the side. The cool summer breeze working its way through his legs and around his balls was liberating but terrifying all the same.

  Finally, he turned around and covered his manhood with his hand. He wondered how weird it would look that his dick was hard, and if it might be off putting to them. Sam jumped up and came over, pulling his hand away. The girls cheered, watching Derek’s hard cock hang down, along with his taut sack.

  She gave his cock a little pat. The unexpected act left him nearly ready to cum.

  “Come on, shake it,” Rachel urged as the girls continued to jeer. Derek, completely immersed in a state of shock, shook his hips and felt his cock bobbing from side to side, until the girls had enjoyed their fill of him.

  Finally, Sam shouted, “Get some clothes on you little bitch!”

  Derek laughed for a moment until Sam came up around him and gave his ass a nice, hard spank. “Come on, get dressed you little slut!” The girls laughed and surrounded Derek as Sam bossed him around.

  “Look at that tiny little dick,” Sam said, pointing. “It doesn’t even qualify as a cock. A cock is big and strong. That’s just a… a wiener!” Sam said with a laugh.

  The insult only made Derek harder than ever. He didn’t know what had come over him. He grabbed his clothes and darted out of the light of the fire and pulled them back on, as the girls continued to hoot and dance to the music. After a moment, he watched Sam say goodbye to the girls.

  “Come on,” she said, waving for Derek. The blonde finished buttoning his shirt and followed her. Sam tossed Derek the keys, which he nearly dropped, and said, “You drive.”

  He didn’t know what had come over him. Never in the city would he have let a girl boss him around. But this country girl was something different. Every order, every insult which left her lips, settled on his body like the touch of sheer pleasure. He only wanted more of her approval, more of her dominance.

  Derek drove them back to the bunk and pulled up in front of his room. Sam cut the engine and pulled the keys from the ignition and the two of them sat in the cab for a moment. Derek looked up at the starry sky.

  “You can’t see that many stars in the city,” he commented.

  “I’ve never been to the city,” Sam said with a little laugh. She shook her head and turned to Derek with a quiet smile. “You know, I was wrong about you. When you first got here, I thought you were going to be a real pushover – a girly boy.”

  “Oh, I’ve really proven you wrong, huh?” Derek said sarcastically. “I only have a tiny dick and do everything you tell me.”

  “So what? There’s nothing wrong with that to me,” Sam said with a wink.

  Sam extended her hand across the bed and ran it atop Derek’s shorts. He inhaled deep and felt her strong hands over his cock, rubbing lightly. She laughed and looked up.

  “Should I stop?” She asked.

  “Fuck no,” Derek breathed.

  “I mean, you’re my boss. I kind of have to do what you tell me,” he noted, reveling in the observation. The mere thought of being ordered around by the beautiful girl was enough to leave Derek on the verge of climax.

  Sam laughed and said, “Come on, then.” The two of them snuck back into Derek’s bunk, pushing open the door.

  “What are we doing?” Derek asked.

  “Well, I’m your boss, and I need you to prove one last thing to me,” Sam said.

  She shut the door behind them and the moonlight crept in through the lazy, dark bedroom. Derek grew dizzy with anticipation – what could she possibly want now?

  “See, here on the ranch, men are made. You’ve got one last thing to prove to me; that you can handle every order I give you,” she said with a mischievous grin. Sam tossed her dark hair to the side and smiled with cool eyes. She swiftly lifted her shirt over her head and shook her hair as her full breasts hung giant in the tiny cotton bra.

  “Fuck,” Derek whispered in a daze. He looked over Sam’s perfect, curvy figure. Her silky skin was radiant, and the more of it that she revealed, the more he wanted her.


  “See, I’ve got a secret,” Sam said, slowly unbuttoning her tiny shorts. Derek swallowed hard, watching as her lithe fingers undid the small beige shorts. She unzipped tortuously slow as she kept her eyes locked on him.

  “There’s a reason why I can outwork all the other guys,” she whispered softly. “And there’s a reason why I’m a bit hard on you. I guess I just have a more dominant nature,” she said.

  “That’s fine with me,” Derek said with an excited smile.

  “Is it? What if I told you I had something a little… extra, that made me this way?” She asked.

  “What do you mean?” Derek asked as his heart raced.

  “Do you want me, Derek?” Sam asked in a low moan.

  Derek only nodded happily as she stepped toward him and hung her arms around the back of his neck. Gazing deeply into Derek’s eyes, Sam searched for the right moment. She smiled and bit her lip, and Derek immediately pressed his lips hard against hers. He tasted her sweet flavor on his tongue as it tangled with her own.

  Derek pulled back for a moment and Sam shook her head. “Tsk, tsk, tsk, Derek. You were being so obedient.” Her mouth curled into a mischievous grin.

  “Since you’re so eager, though, I think you should see what I’ve been hiding all along,” she whispered.

  She eyed down her body and allowed Derek to run his hand over her breasts, massaging and sending shots of pure bliss across her skin in the pale, dim lighting of the empty room. Derek inhaled her sweet vanilla scent and eyed down, following her.

  Unable to wait any longer, Derek ran his hand down her soft navel and inside her shorts, which were hanging loosely around her hips. He could feel the soft, trimmed bush just inside her panties and he inhaled. His search ended abruptly, as he tried to decipher what he’d run into.

  Sam laughed wildly as Derek ran his fingers down around the base of her fat, swelling cock. The warmth inside her panties left his fingers balmy and light. He looked up and scrunched his brow as she seemed unable to help from laughing indulgently.

  “Wait a second… um…” Derek started.

  “Looks like my little secret is out,” Sam said.

  “Uh, little? You’re kidding, right?” Derek said, trying to wrap his fingers around Sam’s massive girth.

  He knelt down and grabbed at Sam’s shorts, pulling them along with her panties down to her ankles. As he did, her giant cock came springing out, hard and accompanied by two giant balls.

  “Holy shit,” Derek said as the massive cockhead nearly swung against his face.

  He could only shake his head and laugh along with Sam, overtaken with disbelief. “There’s no way.”

  “Is it so strange? So I have a dick,” Sam said with an innocent smile. “It doesn’t make me less of a woman. If anything, maybe it makes me more of one.”

  “The only question is; are you still willing to prove yourself?”

  Derek looked up at Sam’s curled lips, as he gripped her cock in his hand and felt her pulsing warmth. “You’ve got one final test before you’re a true ranch-hand around here.”

  Derek’s mind flared with a million conflicting thoughts. I’m not seriously about to do this, am I? He thought to himself as the tip of Sam’s cock starred him down. He wasn’t gay, and had never considered himself the curious type. Yet as Sam stood before him with her massive tool hanging between her soft, lithe thighs, he wanted more than ever to stroke his first cock, knowing it would give her the pleasure she had ached for the moment she had first seen him.

  He had his reservations, and yet his only reservations came from the fact that he didn’t have any intention of stopping now that he’d the hottest girl he’d ever known totally nude before him. He was going to do everything she asked, just as he’d done thus far.

  And without any further answer, Derek parted his lips and sank his mouth on Sam’s warm, massive cockhead. As the spongy, crested head stuffed his mouth, he tasted Sam’s sweet, vanilla skin stuffing him to his brim. He couldn’t believe he was sucking his first cock, but his own rock-hard dick was the perfect indication that he was doing exactly what he’d always been destined for.

  “Fuck,” Sam moaned, letting her head fall back as she ran her hand over her breasts.

  Derek particularly enjoyed the surprise he’d gifted to her, and certainly had every intention of going the extra mile. He was no city slicker, if this was the litmus test for a true country boy. He sank his mouth deeper on her cock, wild with the realization that he was actually licking another dick. The moment he started, the shock and the shame ended. Suddenly, he was simply pleasing another human. He cared about Sam, and with every soft moan she gasped, he only sucked harder.

  Derek grabbed his own cock and stroked lightly, just inside his shorts, before Sam looked down and grabbed his head. “No, no,” she said, insisting he pull off of his cock. “That’s going to cost you.” The dark-haired vixen pulled Derek’s head onto her cock and he felt her stiff shaft drive deeper toward his throat, before he quickly pulled back and gasped.

  “Fuck!” She cried out. Her cock throbbed and the head flared as he grabbed her wet cock and stroked it.

  “My turn to return the favor,” she said, pulling Derek up and pushing him toward his bed. She yanked his shorts down to his knees, along with his boxers, until she caught sight of the same below-average cock she’d come to love. “Mm,” she moaned, licking her lips.

  Derek lay on his back on his bunk as Sam sank her mouth over his cock. She wasted little time, driving all the way to Derek’s base with a vigor that he’d never known. He moaned, tensing his entire body as he felt the instant pressure of climax building behind his balls.

  “Fuck!” He called out into the still air of the dark, cool bedroom. Sam’s beautiful little mouth slurped over his cock as she massaged his balls and suddenly ran a finger down toward his ass. The sensation opened up an entirely new possibility for the blonde ranch hand. He could only imagine Sam grabbing her massive cock and shoving it deep inside him. He never before had considered such a dirty, forbidden thing. Yet, with Sam, it seemed so appropriate – so perfect. He wanted to hear her moan and plead for release as she fucked him. He was her tool, her submissive, and he wanted to make his boss proud.

  Sam pulled Derek’s legs up into the air until his tight asshole was in her view. She moved her mouth down past his balls and teased around his opening, watching him writhe with bliss. Finally, she slid a finger just inside and sank her mouth back over his cock, bobbing back and forth until he winced with abandon.

  “I’m going to cum,” he cried out.

  With Sam’s finger sliding deeper inside him, Derek clenched his jaw and felt his abs contract as the fiery pressure barreled throughout his core and sought any exit possible. Like a ball of fire pushing down an impossible snug channel, he felt cum rocketing out of him and straight into Sam’s sweet mouth.

  “Oh… fuck!” He moaned as rope after rope shot toward the back of Sam’s throat. His body pulsed around her finger and he contracted endlessly.

  His chest heaved with breath before he felt the last drops delivered to Sam’s sweet, pretty throat. She pulled from his body and smiled as she happily swallowed his submissive, sweet seed. Derek loved watching her do this, especially as she followed with a loud gulp.

  “Tasty,” she said with a gasp of enjoyment.

  “Time to return the favor,” she said, motioning for Derek to move back down to his knees.

  Derek disobeyed his boss, though. Perplexed, Sam asked why he wasn’t moving to the floor. Derek only shuffled slowly until he was on his belly with his ass hanging over the edge of the bed.

  “I’ve got a better idea,” he said.

  “Derek, you don’t have to. The test is simply…” Sam started.

  “Fuck me,” Derek growled, looking back over his shoulder. Sam smiled mischievously and gave his perky ass a hard spank.

  “So you want to stand out, huh?” She asked. “I think that can be arranged.”

  Sam sank her mouth to D
erek’s ass and immediately rimmed him, teasing him as his entire body clenched. Soon enough, she grabbed her cock and rubbed the head against his opening. The blonde felt the hard fleshy head against his hole and he tried to imagine just how he was going to accommodate Sam’s massive cock. There was no trying – he would have to, no matter what.

  After a moment of pause, Derek suddenly felt Sam’s cock pushing against his opening. He winced and grabbed the bed sheets in his fists as Sam sank her cockhead right into his tight little ass. He opened up around her and gobbled her tool, and the dominant, dark-haired vixen watched in delight as the submissive twink ate her cock hungrily in the moonlight.

  “Fuck!” He groaned out, feeling the fat member split him open.

  Derek was her tool, now; a mere extension of Sam. There was no going back. He had crossed a line that he could never return. He hadn’t ever anticipated such a dirty act, but with Sam, it seemed only natural to let the country girl dominate his ass.

  Sam pushed down and sighed with delight as Derek’s warm ass enveloped her cock.

  “Oh my… fuck,” Derek cried out, gritting his teeth as the burn swelled through his body. Sam’s cock was fatter than any he had ever seen, and he couldn’t have imagined anything fitting inside his tight ass. He winced and rode out the nearly unbearable pain as it suddenly gave way to ecstasy.

  She buried deeper and felt the heat of his body around her tool as she pulled back and thrust again. Derek groaned and grunted as his boss fucked his tight ass, stretching him open for the first time.

  As he felt her thick cock press against his prostate, he could only fantasize about being fucked raw and filled with her dominant seed.

  And that was exactly what Sam intended to do.

  The raven-haired vixen pumped Derek’s ass as her breasts bounced. She thrust her curvy hips with each pump and greedily sank deeper and deeper with every reentry until she was balls-deep inside him. Sam then thrust harder than ever, pounding her submissive little bottom; her new ranch-hand girly slut. Derek wondered how long it would be before word got out about this to the rest of the girls. The thought crossed his mind that they might be interested in joining in, and this left him especially weak in his knees.