Man to Woman

by Jane Futa

  As the soft panties slid up his thighs and tightened around his waist, he adjusted his cock, shoving it inside, just as the thong string slid between his ass cheeks. Jake winced as his cock swelled and started to harden.

  His cock had chosen the perfect time to betray him, and hardened inside the tiny panties.

  “Did you hear something?” One sorority girl asked the other. Both of them stood up from the bed, their blonde and brunette locks bobbing as they remained still, trying to hear for any additional sounds.

  “I swear I heard something, Vanessa,” the blonde girl said.

  “Oh my god, Kelly; what if there’s a serial killer in the closet?” The brunette said, with an overly dramatic gasp.

  “Cut it out, Vanessa,” the blonde said, shoving her.

  “Stop!” Kelly cried, as both girls shoved one another. They laughed for a moment as the noise returned and they heard a thud against the bottom of the closet door.

  “Fuck, fuck!” Jake whispered as his chest heaved. The lean stud reached down to grab the shoe that he had accidentally kicked, just as the girls pulled the closet door open.

  “Oh my god!” They screamed. The girls darted their wide eyes up and down the eighteen year old college stud that had somehow ended up in their closet, wearing nothing but a tight white t-shirt and a silky purple thong.

  Almost immediately, the shock and horror turned to uncontrollable laughter. The blonde and brunette could barely stand as they pointed and laughed at Jake, who was trying to keep his cock from popping out of the tiny satin thong.

  “Fuck,” he sighed, rolling his eyes.

  “What the hell is going on? Who are you? And why… oh my god… why are you wearing… wait a second,” Kelly called with her arms outstretched, before stopping and leaning forward.

  Her eyes squinted as she pointed and shouted, “Oh my god, Vanessa! Those are your panties!”

  The brunette’s brow furrowed as she huffed and stepped toward the short college boy, who was all but cowering in the closet.

  “Get out here, right now!” Vanessa demanded.

  Jake swallowed hard and stepped out of the closet, one foot at a time. He bent down to grab his jeans and his shoes, before Vanessa and Kelly quickly shrieked.

  “Don’t move a muscle!” Vanessa cried.

  “Get out here now,” Kelly added, tapping her foot against the floor.

  Jake’s heart raced. He was busted in the absolute worst way, with two gorgeous women eyeing his package as it sat snugly inside a tiny pair of women’s panties. He kept his hands over his crotch as he came out into the light of the bedroom, standing before the two girls, who proceeded to step in toward him.

  “Well, well, well,” Kelly said. Each girl stood at his side, and, like so many other Phi Beta Transa girls had, towered over the frat boy freshman.

  His heard sped, and his fists shook as he bit his lip and tried to figure out just how crazy it would look if he’d took off out of the bedroom, down the hallway and out the front door, all while in women’s panties. Worse things had probably happened on Sorority Street, after all.

  Ultimately, he decided against it. But he knew that if anything got too crazy, he was making a run for it.

  “So, you’d better start explaining before we call security,” Vanessa said. The brunette looked over Jake. Her cool brown eyes matched her long, shoulder-length dark hair. She was tall, perfectly curvy and big-breasted. She seemed like the star of a dominatrix film, which didn’t make Jake feel much better, given the road he was on. And yet at the same time, he felt his cock twitch as he kept quiet and sealed his lips. He knew he was bound to secrecy.

  “If you get caught, you’re just a random pervert,” one of the frat brothers had ordered him. He would be out if he spilled the secret, and so he remained quiet and simply eyed straight ahead, staring out the window, and wishing he was right outside of it in that tense moment.

  “Well? Do you have anything to say for yourself?” Kelly asked.

  Jake shifted his eyes from side to side. Though his heart raced like a hammer, he remained still.

  “You know, this isn’t a bad look for you,” Vanessa said. The brunette ran her finger down the front of Jake’s shirt, and the frat boy felt a wave of goose bumps as the sensual touch travelled slowly down his chest and navel. Her finger continued, veering right for his crotch, as the blonde girl laughed and nodded.

  “We know a thing or two about sissy boys, and you look like a real specimen,” Kelly added.

  “Sissy boy?” Jake asked, finally breaking his oath of silence.

  “Oh, so he can talk,” Vanessa said, eyeing her sorority sister.

  “Care to tell us what you’re doing in our room, now?” Vanessa asked once more, and brought her finger up to Jake’s chin, grabbing it and shaking playfully.

  Jake’s heart sped, his legs tightened and, as he looked down, his cock swelled; once again choosing the worst time possible.

  “Mm,” he moaned just beneath his breath. The girls looked down and saw the growing tent in the frat boy’s panties and laughed with approval.

  “Oh my,” Kelly said, her green eyes wide and excited. She leaned down for a closer look and after a moment, her face was only inches from the frat boy’s small cock. This only made his cock swell more, each time gifting the girls a nice little pulse inside the thong.

  Kelly reached her fingers over the thong, stroking just over the fabric, and Jake let out a soft sigh.

  “Oh yeah; this boy has sissy written all over him,” she said, eyeing the brunette.

  “Well, he’d better start talking soon, or he’s going to find out why nobody sneaks into the Phi Beta Transa house,” Vanessa said with an indulgent grin.

  “You don’t mean…” Kelly asked with a small gasp.

  “What else could I mean? Look at him; he’s just ripe for the picking,” Vanessa giggled, tapping Jake’s lips with her finger. Her purple-painted finger nails wagged against his face as she gave the frat boy a little playful slap against his cheeks.

  Kelly came around behind Jake and giggled. “You’ve got to get a look at this perky little ass, Vanessa.”

  The brunette stuck her head around Jake’s body, and smiled. “My goodness; you’re made for thongs – that’s for certain,” she said with a flair of satisfaction beaming in her eyes.

  “Please,” Jake started. “Don’t turn me in. I’ll… I’ll do anything,” he pleaded with his hands clasped together. The blonde got to his knees, as if begging for his life.

  “Hmm,” Vanessa said, cocking her brow. “Anything?”

  The tone of the brunette’s voice left a churning in Jake’s stomach. What could she possible have had in mind? He was, after all, already wearing women’s panties. What could they possibly do to demean him any further?

  The blonde hadn’t been initiated to his fraternity yet, though. Unfortunately, the frat brothers knew the Phi Beta Transa campus secret, and part of Jake’s initiation, was to learn the secret for himself.

  “He’s definitely a pledge,” Vanessa noted, pacing around the frat boy and inspecting him from head to toe.

  “How did you know that?” Jake asked.

  “Well, I didn’t. But now I do,” she said with a grin.

  “Get that t-shirt off, right now,” she demanded.

  Jake quickly obeyed, pulling the soft white shirt up and over his head. As he felt the cool air of the bedroom against the skin of his lean, bare chest and abs, he looked down in shame as the two tall sorority sisters giggled and pointed at him.

  “He’s so small,” Kelly said with a laugh. “He looks like my little sister!”

  Jake shook his head in disbelief. He tightened his fists and tried to figure out just how he’d ended up in such a mess. Though he’d thought that he could keep his true mission secret, he didn’t realize that the Phi Beta Transa girls were well aware of his intentions.

  “Truth be told; you’re far from the first freshman boy to end up in our closet wearing our panties,” Van
essa explained.

  Jake cocked his head with confusion. “Seriously?” He asked.

  “Oh yes,” Kelly added. “We know why you’re here. The frat on Elm street sent you, didn’t they? This isn’t the first time they’ve doomed one of their pledges to a failed mission at our house.”

  “To be honest, we’re all good sports about it,” Vanessa said. “But actions aren’t without consequences.”

  The girls paced around the lean college freshman. His chest heaved with breath as he tried to predict their next move. Unable to, he felt the twang of anxiety wash over him. And yet because the girls were so gorgeous, he knew that whatever his punishment involved, it would be far from miserable, so long as they found any joy in it.

  He felt a swell of desire in his panties as the girls both looked down and decided to inspect his bulge. Something deep inside him swirled with uncontrolled lust. He bit his lip and moaned as he realized he was a prisoner of the domineering women. Never before, would he have expected such a situation to leave him hard and horny. But as the girls both eyed his crotch, he felt himself throbbing hard.

  “Considering how tiny that thong is… you must not be working with much,” Vanessa said.

  Jake moaned as the brunette slid her finger just inside the band. Her curious, lithe hand ran against his trimmed bush and just grazed the base of his cock, before hooking back up and pulling at the band of his panties. She pulled them out, as both girls leaned in and looked inside the purple thong, helping themselves to an eye-full of the sissy’s small cock.

  Kelly burst into laughter, followed by Vanessa. The humiliation should have sent a wave of pain throughout Jake’s core. And yet, the sheer attention left his legs weak and his balls full of anticipation. He didn’t care – he was aroused, merely at the fact of being the girls’ spectacle of amusement.

  “Wow,” Vanessa said, letting the panties seal back against Jake’s lower abs.“I’ve seen some small frat guy dicks but that is pretty tiny.”

  “I know how to use it,” Jake said, defiant.

  “Oh, do you?” Kelly asked with a curious smile.

  “Maybe he should show us,” Vanessa said to the blonde sorority sister.

  “I like that idea,” Kelly replied.

  “Ok frat boy – strip,” Vanessa demanded with a snap of her fingers. “Get my panties off right now!”

  Jake swallowed hard and looked at both girls. Were they serious? He ran the demand over and over in his mind, unable to believe that they were honestly asking him to strip, until Kelly broke his concentration with a nice, hard slap on his ass.

  “Come on sissy boy; get naked!” The blonde growled with a furrowed brow.

  Jake slowly grabbed the band of his thong and started to pull it down. As he did, his cock sprang up, hard and full, followed by his small, taut ball sack. He slid the panties off his legs until they became a loose bunch on the hardwood.

  Jake covered his crotch instinctively, until the girls pulled his hands away.

  “Turn around; model for us,” Vanessa insisted.

  Jake obeyed and turned his body, before the brunette chimed in with another request.

  “Come here; on the bed,” Vanessa said as she patted onto the pink bed sheets, as if instructing a dog. “Rig here. Get on all fours and put that tight ass in the air.”

  Jake bit his lip and moaned. The demands were making him hornier than ever, much to his own surprise. He’d come to college to fuck women, not be ordered around by them. And yet, here he was, a complete fool being bossed around and humiliated by a pair of drop-dead gorgeous girls.

  Jake hesitantly climbed atop the bed and felt the silky cool sheets beneath his knees as he turned away from the girls and bent over.

  The girls laughed and stepped toward him, until he suddenly felt them playfully spanking his ass and tickling just between his balls and asshole.

  “Oh,” Jake moaned as Vanessa’s finger softly teased at his opening. Vanessa watched, wild with attraction as the sissy boy’s tight ass puckered in response.

  “Oh, this is too good. You’re the perfect little sissy slut,” Vanessa said, coming around and sitting on the bed. She came around and sat against the headboard, splaying her legs open just in front of the frat boy’s face. His eyes lit up as he looked down at the tight little pair of shorts in front of him.

  Vanessa grinned and stroked Jake’s chin.

  “So, you have two options here,” she started. “You can do as we say, or you can take a trip to the dean’s office and explain why you were stealing sorority property.”

  Jake knew the decision was easy, but was hesitant at just what the girl’s had in mind. He swallowed hard and nodded. “I’ll do anything.”

  “Good,” Vanessa said. She slowly unbuttoned her shorts, and Jake licked his lips.

  Kelly smiled behind the lithe frat boy and gave his ass another spank as the brunette started to slide them from her body.

  “You’re going to do anything? Did I hear you correctly?” Vanessa asked, one final time.

  “Yes – seriously anything,” Jake nodded.

  “Excellent,” Vanessa said. “Then if I ordered you to… I don’t know… please me and Kelly, you would do it without a single objection?”

  Jake felt his body tighten with lust as he imagined the wild things he might do to each of the beautiful teens. He nodded his head happily, ready to feast on the juicy pussy that the brunette was only moments from showing him. He licked his lips, waiting to taste the little red slit that was waiting just inside her shorts.

  The brunette slid her shorts down, and immediately, the frat boy cocked his head, trying to figure out what was wrong about the girl’s panties. There was something he couldn’t put his finger on.

  Yet he waited still, in anticipation, as she grabbed at the band of her white cotton panties. She put her legs up and together into the air and pulled the panties over her feet, letting her giant cock and balls come hanging out.

  “What the… holy fuck!” Jake cried out with wide eyes. His jaw hung open in shock as the brunette woman splayed her legs out and let her massive, hard cock spring up, towering over her waist and her heavy balls.

  “Surprised?” Vanessa asked, as Kelly let out a raucous laugh.

  “Holy shit,” Jake said once more, shaking his head, as if he’d simply seen incorrectly. He opened his eyes again, only to see the same, thick, long cock.

  “You have a… you have a dick!” Jake shouted. “You’re a dude?”

  “Wait a second, wait. I’m not gay. When I said I would do anything,” Jake continued, shaking his head.

  “Um, I’m not a ‘dude,’ first of all. I’m a woman, clearly,” Vanessa said. With a curl of her lips, she massaged her full breasts, and pulled her shirt up and over her head, letting each heavy orb fall. Her silky smooth skin glistened in the evening sunlight of the bedroom. Jake couldn’t have felt any more conflicted, watching the perfect set of gorgeous breasts, and looking down to see a powerful, merciless cock, connected to the same body.

  “What do you think?” Kelly asked, coming around and sitting beside Jake.

  “Are you… are you a guy, too?” Jake asked, turning to the blonde.

  “Um, again, I’m not a guy. And neither is Vanessa. And no, I don’t have a cock like she does. I wish,” Kelly explained. “Some Phi Beta Trans girls have dicks, and some, like me, just get to enjoy the gifts of our sorority sisters,” Kelly finished with a smile and a wink toward the brunette.

  The blonde came over and grabbed Vanessa’s cock. As her fingers wrapped around the thick pole, the brunette’s hips writhed, and she moaned loudly.

  “See, you may not be in the frat yet. But you’re about to become the newest sorority sister,” Kelly explained as she stroked Vanessa’s cock casually. Jake watched, mesmerized, as the brunette’s giant balls jumped up and down with each tug.

  He couldn’t help but feel a pang of pleasure crawling throughout his body. Suddenly, he realized what his punishment would be, and though h
e never would have considered it before, he found his body swept with a desire for the brunette’s special gift.

  “You’re going to enjoy our initiation; I can tell just looking at you,” Vanessa moaned.

  “You’re first job is to get your mouth on this cock and make my sorority sister beg for mercy,” Kelly said with a sizzle in her voice.

  Jake hesitantly neared the massive cockhead. He slowly reached and wrapped his fingers around the wide shaft. As he felt the warm throbbing in his fist, he shook his head in disbelief.

  “What’s it like to stroke another cock? Or, is this not your first time?” Kelly asked.

  “It’s my first time,” Jake admitted.

  “But you’ve wanted to before, haven’t you? You’ve fantasized about dressing up like a little sissy slut and letting the frat brothers have their way with you, haven’t you?” Kelly asked.

  As Jake stroked Vanessa’s cock, he felt his own tool throb with delight as Kelly played out the image in his head. Deep down, in a way he would never confess to another, he had thought of this a few times. If he were free to pursue his most secret inhibitions, then perhaps he would have, given the opportunity.

  “Well, you don’t have to be ashamed. Because now, you get to know what it feels like with a couple of hot girls, instead,” Kelly explained.

  “Now,” she said, grabbing the back of Jake’s blonde hair and pushing his mouth down. “Why don’t you get a taste?”

  As the brunette girl’s massive, flared cockhead sunk into his lips, Jake tasted the warm, sweet skin of her spongy head, stuffing his mouth. The shaft filled him and pushed back toward his throat, as the blonde sorority girl continued to push his head down, slow but slightly merciless.

  Jake felt a slight gag and pressed back, before pulling back up and off. He gasped and wiped his mouth, as both girls giggled excitedly.

  “Hang on,” Kelly said, before rushing over to the night stand. She pulled a small shiny tool from the drawer and climbed back atop the bed. Before Jake could see what was happening, the blonde had held his chin still, and sloppily drawn a nice even shade of red over his lips.