Man to Woman

by Jane Futa

  As if he’d been made to suck dick, Raymond bobbed back and forth on my length, gifting me the delicate, intense bliss of a warm, wet mouth. The athlete pulled back for a moment and gasped, asking, “How is that?”

  “How is this for an answer?” I asked, before pulling his head back down over my cock. “That’s it. Suck that dick like a good little sissy boy.”

  The college running ran his hands over the tops of my thighs as my knees buckled. I moaned and eyed the door, hoping that none of my fellow nurses would pop in to make sure the appointment was going well. My heart raced, but it only made my cock throb more as I grabbed Raymond’s curly hair and pulled his mouth as far down on my cock as I could, before he pulled off and gasped.

  “Stroke it,” I insisted. “Show me how much of a man you really are.”

  Raymond slid his hand over my cock, wet with his saliva, as I pulled him up and bent him over the exam table. “What are we doing now?” He asked.

  “It’s the last exam I need to do, just to make sure you’re good to get back on the track field. This is an anal exam of sorts,” I said, as I slid a finger down and teased his ass crack. The running tightened his legs and moaned, throwing his head back.

  “Mm hm,” I hummed. “I knew you weren’t being honest with me. Here you were acting like you were a ladies man when the only thing you are is a lady man.”

  “This asshole is so tight,” I said as I slid a wet finger just inside him, and listened for his moan. As the teen breathed heavy, I grinned mischievously.

  “You’ve already experimented here yourself, haven’t you? What did you use? A carrot? Or maybe a cucumber?” I drove my finger deeper inside the sissy boy and smiled. “Oh, I know that moan,” I added as the college athlete sighed with delight and grabbed the exam table edges.

  “You’re going to make a nice little fuck toy,” I said. “That’s what you’ve been wanting all along, isn’t it?”

  “Yes,” Raymond moaned in confession. His ass continued to flex around my finger, but as I massaged, I felt him give way. It wasn’t my first time, and I knew exactly what the closeted sissies loved.

  Giving his ass a hard spank, I grabbed my cock and stroked it. I could hardly wait to watch it disappear inside the snug, warm hole. I had to be patient, however. The tight, lean twink needed some special preparation to take my thick cock.

  “Fuck,” Raymond moaned. “Just like that.”

  “Oh?” I asked, cocking my brow. “So the truth comes out, does it? You have a special spot right up inside that tight little asshole? Why am I not surprised?”

  I shoved another finger inside and spanked the sub once more. “I’m going to make you cum all over that exam table for grabbing beneath my skirt.”

  “I’m not gay, though,” Raymond added again.

  I leaned over and whispered in the cute college stud’s ear. “Your secret is safe with me. And like I said, I’m all woman – I just have a little extra. And you’re about to feel it for yourself.”

  I grabbed my cock and rubbed the head against the track star’s tight little opening. “Now, do you want this to split you open or not?” I asked.

  “Please,” Raymond begged in a loud, stifled moan. “I knew it,” I grinned.

  “You’re about to learn the rules of the exam room,” I said, shoving my cock against his opening and watching his asshole open around my cockhead.

  “Fuck,” I breathed, watching him gobble up my cock ever slowly. The heat surrounded my cock and I felt the million or so stings of bliss crawling up my body. This was going to be a fucking neither of us would ever forget.

  “Oh… fuck!” Raymond cried out. I felt a special satisfaction watching the submissive grab harder at the exam table as my cock split him open. I knew that lovely soreness that was swelling his ass about then. And I knew the sensation that would follow it, would have him begging for every inch.

  “Oh, does the little track star sissy like getting a cock up his ass?” I asked, slapping his cheek.

  “Yes,” Raymond sighed.

  “I didn’t realize you were such a girly little slut,” I said, thrusting my hips fast and watching his ass take my entire length. The track star moaned out loudly and I pulled back, before watching in amazement as Raymond pushed his ass back onto my cock.

  “Oh, you really like this big cock, don’t you?” I asked.

  Raymond moaned, and I smiled. “You’re such an obedient little sissy slut. I can’t believe you wasted your time chasing those college girls, when you should have strutted that ass around the real women like me.”

  I slammed my cock back inside the track star’s little ass, before pulling back and repeating. The tightness in my core swelled, and I knew it was only a matter of time before I would explode. As my skin slapped against Raymond’s, I watched his face wince.

  “I’m going to… oh fuck!” The tight teen cried out, grabbing at the butcher paper and moaning wildly. I took that as my signal to slam my cock mercilessly into the snug ass, watching as the cocky little athlete had every last drop of cum fucked out of him by a giant cock up his asshole.

  The image of white streams, drizzling down the side of the exam table, was too much. Coupled with Raymond’s tight ass contracting around my cock, I couldn’t hold on any longer. The dirty little sissy boy had gotten the best of me.

  “You little slut,” I growled. “Your asshole just has to have this cum, doesn’t it?”

  “Give it to me!” Raymond cried out.

  “You want every last drop of a real woman inside you?” I asked one last time.

  “Yes… teach me how to take it!”

  Without any further ado, I thrust my hips deep against his ass and felt the raging, merciless bliss as it thundered through my body, up my legs and exploding from my balls.

  “Fuck!” I cried out, gritting my teeth and tightening my eyes as the impossibly forceful load shot into the airtight space. I thought I might collapse from the intensity and I pushed, balls deep, into the sissy’s ass, making sure he took every last drop of my seed into his backdoor womb.

  “Oh!” Raymond cried out as our cocks each shot each last, weak load and dirtied everything in sight.

  “Fuck,” I moaned, gasping for breath as I collapsed against the sub’s lean back.

  “I can feel it inside me,” Raymond whispered.

  “As you should,” I said, panting with breath. “You like it don’t you?”

  Raymond nodded and with a blush admitted, “That was amazing.”

  “What are you so embarrassed about, honey?” I asked. “You wanted to fuck the hot nurse, and you did; maybe not in the way you imagined, but you did.”

  “You’re going to be a bit sore for a while though. The sports medicine should help with that, though,” I said, remembering his prescription as my cock continued to swell deep inside his warm ass.

  Finally, I pulled out and listened with delight as the track star sighed and moaned. His ass pulsed and he turned around to face me. “Fuck,” Raymond breathed, smiling as his cock hanged, limp and tiny again.

  “I didn’t want to have to do that today,” I noted. “But you can’t just go reaching up a girl’s skirt like that, digging for the gold inside her thong. Who taught you those sorts of manners?”

  Raymond shrugged and hinted that his father might have had a hand in it.

  “He wants you to be a big ladies man, doesn’t he?” I asked. Raymond nodded.

  “But you’re not cut out for that at all. You always wanted to be a little sissy boy, didn’t you?”

  Again, Raymond nodded and I grinned.

  “Well, maybe we’ll have to increase your visits for the next few weeks. Let your coach know that I intend to see you here in my office every afternoon for physical therapy.”

  Raymond nodded happily. “You won’t tell anybody, right? It’s just going to be our secret?” He asked with a sudden expression of concern.

  “Of course not, so long as you straighten up and stop treating women like garbage
. Maybe soon enough you’ll learn how a man is supposed to treat a lady.”

  “I think I just learned,” Raymond grinned.

  “Oh, there’ll be plenty where that came from. This exam isn’t finished in the slightest,” I said, before popping my head out of my office door. “Julie, cancel my appointments for the afternoon. Raymond is going to need some seriously in-depth therapy.”

  The track star bit his lip as I walked back toward him with my hips strutting.

  “Now, why don’t you show me how you clean a woman’s cock off after she’s made an example of you,” I instructed.

  Raymond nodded and knelt onto his knees. I could tell that this was the beginning of something big. Raymond wasn’t just going to be a track star any longer.

  With any luck, he was going to be the best sissy in town!

  Femdom Sorority

  This is so stupid. Jake shook his head and balled his fists, determined to press on.

  The blonde college boy knew he shouldn’t be sneaking into the Phi Beta Transa sorority house, but a dare was a dare. And the lean stud knew that if he didn’t return to the frat house with at least one sorority item, he was going to be the laughing stock of pledge week.

  Looking around the corner of the red brick house, Jake eyed a neatly manicured lawn. The lazy evening breeze glided through the trees and the lawn, silent and empty as any horror film. He’d chosen the end of the month, because he knew all the girls would be at their weekly charity event on the other side of campus, leaving Sorority Street a ghost town.

  Jutting his tongue against the corner of his mouth and clutching the key he’d swiped from beneath a little frog statue, the blond frat boy stepped one sinewy, long leg in front of the other, as he discretely snuck toward the front colonnade.

  “Shit,” he gasped in relief, as he made it up the steps and found himself mere inches from the front door.

  He peered out from the front porch as the dusk sky turned a deep shade of rust, covering the endless sorority street. He couldn’t even remember at that point how he had gotten himself in such a foolish mess. All he knew was that he needed to get into the sorority house and right back out, and his troubles would be far gone.

  Turning the key in the latch, Jake grinned as two dimples formed on each cheek. “Open sesame,” he whispered to himself in delight.

  As he entered the foyer, he eyed the wide stairway just before him. The Phi Beta Transa house was fit for a queen; much larger than the frat house. The girls had been a fixture on campus for decades, and their well-connected nature showed in the wealth that poured from every inch of the ornate sorority house. The sleek, widescreen television and the giant leather sofas in the front living area, almost made him wish that he were a Phi Beta Transa girl.

  “Ugh, no time to go thinking about that again,” he whispered to himself. His small cock hadn’t gotten the memo, however, and swelled slightly in his tight jeans. There was something alluring and perhaps even arousing about being in the domain of such gorgeous and powerful women. Here he was, a little twerp sneaking through their headquarters and hoping to come out unscathed, and the sensation left endless thrill crawling over his skin. He hadn’t been able to detect where this strange erotic fixation had developed, but he knew that it had been a recent change in him.

  Then again, Jake knew it probably had had something to do with the frat brothers making him dress up as a girl and pose for a secret calendar photo shoot. At first, the hazing ritual was entirely nerve-wracking. Despite the explanations by the brothers that it was ‘tradition,’ Jake wanted no part in it. But, if he was going to run with them, he had to suit up in the summer dress and panties.

  So, in the bathroom of the frat house as he tried to calm his racing heart, Jake slid the little cotton thong up his long legs, followed by the dress. The sensation of having women’s panties around his waist left his cock bulging hard. This of course, was the worst time for a hard-on, and his cock slid right out of the tiny thong and against his leg until it poked against the summer dress, forming a small tent in the floral patterns.

  “Come on, bro!” One of the brothers had called, banging on the bathroom door. “You’ve got two seconds to get out here or you’re disqualified,” another called through the door.

  Jake inhaled and stepped out. Tried as he had to hide the sprouted erection, the frat brothers detected it immediately. And when he was instructed to get on all fours and pull his dress up, letting the camera see the tiny thong riding against his ass and balls, he nearly came. He reviled and loved every moment, much to his own surprise.

  As he looked snuck up the stairs of the sorority house, he shook his head, remembering that night vividly. After that, he’d found himself fantasizing about buying a pair of panties for himself. The thought alone left him hard, and he quickly tried to block it out of his mind.

  “You’re a guy… a straight guy,” he reminded himself as he topped the steps and started down the long corridor of upstairs bedrooms.

  The hardwood creaked beneath his feet, even as he tried to be as silent as possible. Through a frat source, he’d been told that the house would almost certainly be entirely empty that night, but he was too skeptical to take that for gospel. Jake stepped to the first door he found, and inhaled.

  “Here goes nothing,” he whispered as his heart sped a million times over and he lowered his hand onto the old brass doorknob.

  He turned it and pushed it ever so slowly; to the point that his body could barely take the suspense by the time that a hint of the bedroom was revealed, leaving him confident that it was empty.

  “Fuck,” he sighed, and stepped inside, closing the door behind him. He looked down and saw that there was no lock, and so his nerves would continue to plague him with every step inside the bedroom.

  Jake took in the room, eyeing the big queen-sized bed, which was covered in an appropriately decorated bedspread. The sheets were pink and silky, with a large Phi Beta Transa logo in the center, along with a few stuffed animals and heart-shaped pillows. Nearby was a small oak night stand and beside this, a large dark wood armoire. The entire room had the mixture of modern girl style clashing with the old-world conservatism of a hundred year-old sorority house.

  Jake eyed the armoire and quickly snuck over, pulling the doors open to reveal a series of small drawers just inside the large furniture.

  His lithe fingers grabbed at each drawer, pulling it just open and quickly appraising its contents. Each one contains several articles of clothing, but the more he searched, the more Jake started to crave darting out of the sorority house with a pair of panties. The final drawer pulled open, revealing dozens of little silky thongs, all various pastel colors. The sight immediately left Jake’s cock throbbing inside his jeans. He grabbed a pair of pale purple panties and shoved them in the tight pocket of his jeans, and started to close the drawer, when his own desires got the best of him.

  Jake reached in and stole a small pair of pink panties for himself, and tried to tuck these in his pocket as well. The tightness of jeans left the pink panties sticking just out in the open, and Jake continued trying to adjust the little cotton thong as he suddenly heard a noise that made his stomach churn.

  Adrenaline barreled through his veins as he heard the sound of several girls laughing. Their voices were dangerously close, perhaps just outside the door. Jake looked around, eyeing the window. “No way,” he whispered to himself, remembering just how high up that second floor was. As the voices continued to near, he looked over and saw shadows collecting just at the crack beneath the bedroom door.

  “Shit!” He gasped, and jumped toward the closet door.

  Jake pulled the doors open and ducked inside, just as the bedroom door opened.

  Shit, shit, shit, Jake thought to himself as two girls entered the bedroom. Jake watched them through the tiny horizontal slats in the closet doors. Though he couldn’t see anything from the waist up, he saw the long, silky legs of two Phi Beta Transa girls. The sorority was notorious for its Amazon-
like women. They always seemed to pledge tall, athletic women, who towered over small guys like Jake.

  It had been bad enough that he had remained a virgin when he stepped foot on campus for the first time. But running right into a Phi Beta Transa girl on his second day, had proven a disaster. Jake hadn’t been paying much attention, rushing to class with his books tight in his arms, and one wrong step led him right into the body of a Phi Beta Transa brunette girl.

  The girl towered over him, and with a hand on each hip, looked down and scowled. “Um, why don’t you watch where you’re going?” The girl said with an annoyed huff.

  “I’m sorry… I really am,” he said, looking up as he collected his books aimlessly. He couldn’t peel his eyes from the girl’s giant breasts, which elicited a flare of further frustration as she brushed her hair to the side and turned away. Another girl came over to her, and Jake could hear the brunette remark: “These freshmen boys are so tiny! They’re cute, but they’re such a pain!”

  Of course, the jilted comment left Jake smiling on his way to class. But he still knew not to cross the women of Phi Beta Transa. And now, he was inside their closet, holding their panties.

  He was screwed, big time.

  Jake nervously tried to shove both pairs of silky panties in his pockets, as the girls sat on the bed and talked rambunctiously. He kept quiet, as if his life depended on it, and tried to make sure he hid the thongs.

  “Fuck,” he whispered. There was only one thing to do to make sure that even if he were found out by the sorority girls, they wouldn’t see that he’d taken their panties. The thought was too ridiculous to bear, but he had to do it.

  As quietly as he could, Jake slipped out of his shoes and slid his jeans down his legs. He took a deep breath and followed with his boxers, sliding the pair down his lithe thighs and shins, before kicking them off his legs. For a moment in time, the cool air of the closet circled his cock and balls, leaving him sighing with delight. He swallowed hard and, with the thong in hand, pulled the tiny, silky fabric around his ankles.