Man to Woman

by Jane Futa

“Now, pucker them like this,” Kelly instructed.

  “Oh, what a pretty little whore he is!” Vanessa giggled.

  “And so obedient, too,” Kelly said, with a harsh spank against the frat boy’s tight ass. “Oh!” He called out as the pain settled into a pinkish welt against his pale ass cheek.

  The girls laughed and Kelly again, grabbed Jake’s head, forcing him down. Jake parted his lips and took in the brunette’s cock. His own cock throbbed wildly. Being so submissive sent a wild fire throughout his entire body that he never could have expected. As he slid his mouth up and down the thick cock, he saw small blushes of his lipstick against the girl’s massive tool, and he felt like a perfect, submissive girl.

  The urge struck him, and Jake reached back, grabbing his cock. Kelly quickly pulled at the frat boy’s hand and reprimanded him. “No!” She said.

  “What do you think you’re doing? Do you think this is supposed to be fun?” She asked.

  “Just for that, you’ll get a little added punishment,” the blonde said, before forcing Jake’s mouth down farther than before, until he felt the hard cockhead burrow down his throat for just a moment. He quickly pulled off and gasped as his throat flared.

  “Fuck,” he breathed. He tightened his eyes and felt the urge to cum right at the edge of his cock, before he finally controlled himself. He knew that if he dared shoot ropes of cum across the bed, he would be in for something far worse.

  “Ok,” Vanessa moaned. “Time for the best part.”

  “Get your crotch less panties,” Vanessa told the blond. The blonde’s eyes widened and she darted to the closet, before returning with a pair of silky, red panties. She pulled on Jake’s feet before he realized that he was the one the panties had been fetched for. He felt as the cool silk slid up his thighs and over his ass, leaving a draft right over his opening.

  The brunette came around and gave Jake’s ass a hard spank, before sliding a tongue just inside the pantie’s opening.

  “Oh fuck,” Jake moaned as the wet tongue slid over his ass, teasing him to submission.

  “So you wanted to eat pussy, huh?” Kelly asked, as she hopped on the bed and spread her legs. She took her own shorts off, along with her panties, until her wet, pink pussy was unfolding right before Jake’s face.

  “You can eat my pussy under one condition,” Kelly said with a mischievous grin.

  Jake’s eyes flared with want as he looked at her sexy little peach. “What?”

  “Tell me how much of a little sissy whore you are, and how much you want to get pounded by Vanessa’s big cock,” Kelly said.

  Jake darted his eyes from side to side, short on words, as the brunette rimmed his ass. Struggling between moans and heavy breath, Jake started. “I want that big cock deep inside my tight girly ass.”

  “Oh, yes!” Kelly moaned, kicking her long legs as she rubbed her pussy.

  The blonde placed one of her feet right against Jake’s forehead and continued.

  “Tell me how much you love big cocks,” Kelly said with a patronizing tone.

  “I love them,” Jake said.

  “Tell me,” Vanessa chided, slapping Jake’s ass.

  “I love big cocks. I love them deep inside me!” Jake said, struggling as he felt Vanessa’s finger slide inside his ass.

  “Fuck!” He cried out. As he moaned, Kelly grabbed the blonde frat boy’s head and brought it down over his pussy, demanding him to eat her out.

  As he did, the brunette grabbed her cock and pressed it against Jake’s asshole. She watched in delight as his tight ass split open around her massive cockhead and the blonde frat boy cried out wildly.

  “You love it, don’t you?” Kelly asked.

  “Mmhm,” Jake moaned against the blonde’s pussy.

  “Do you want it deeper?” She asked, as Jake returned a nod of agreement.

  Vanessa thrust harder and watched as her cock disappeared inside the college boy’s tight asshole. She felt the snug warmth choking her shaft as he sank deeper and deeper toward his core. She loved breaking open the freshman college boys; it was a novelty that never lost its glean. Jake seemed to be the best one yet.

  She smiled toward Kelly, who was moaning wildly. “This little sissy is pretty good at eating pussy,” she gasped as her hips grinded against his face.

  “Maybe that’s because he has a nice little pussy of his own,” Vanessa said, slamming her cock all the way inside and watching the base of her cock push against the frat boy’s ass.

  She pulled back as Jake cried out over the blonde’s pussy, and just as her head nearly pulled out of the warm, inviting ass, she slammed it right back inside.

  “You college boys are all the same; you’re so clumsy with your cocks. You just want to pound and pound and pound,” Vanessa said, thrusting hard and fast, as if to mimic her description.

  “But it takes a special kind of girl to enjoy that. It takes a really little slut to love it hard and fast. Isn’t that right Jakey-poo?” She said with a little giggle.

  “This little slut is going to make me cum all over his mouth,” Kelly cried out, tossing her head back.

  She balled the bed sheets in her fist, and grabbed a pillow in the other, bringing it against her mouth and screaming into it as the blonde frat boy brushed his tongue hard and slow against her little stiff clit.

  He lapped his tongue obedient and rhythmic as Kelly grabbed his head and held it down against her mound, making sure he didn’t pull up until the task was complete. Jake wanted to pull up and scream, as the brunette slammed her cock harder and faster than he could comprehend. He felt his entire body split open and stretched over the massive cock, as the girth massaged his prostate. He knew that he couldn’t take much more and if Vanessa didn’t stop, he would cum.

  The brunette was merciless and pounded harder than ever, as Jake cried out onto Kelly’s pussy and felt the hard ropes rocketing from his small cock. The warm seed shot forward and past his belly, landing onto the bed sheets and even grazing the blonde’s pussy. He felt the warm ropes against his chin and his lips as he finished bringing the blonde sorority girl out of her mindless bliss.

  “You rotten little whore,” Kelly said, lifting her eyes and looking down.

  “What happened?” Vanessa asked.

  “He almost came on my pussy!” Kelly cried in horror.

  “Sorry,” Jake breathed.

  “That’s no good,” Vanessa said, shaking her head.

  “There is only one thing that will make up for that,” Vanessa said, spanking the blonde’s ass. “And I think you know what that is.”

  Jake felt his cock still throbbing with orgasm as he nodded and begged in the midst of his ecstasy.

  “Fill me!”

  “Oh, you would love that wouldn’t you? Does the little sissy want his asshole filled with a real woman’s seed?”

  “Yes!” Jake begged.

  “Say please, you dirty little girl slut!” Vanessa said, spanking his ass harder than before.

  “Please cum in me!” Jake cried out as the last few drops of cum drizzled from his limp cock. His entire body tensed with soreness as the sorority girl’s massive cock tore deep inside him, stretching him open and preparing him for the ultimate finish.

  Vanessa slammed her pelvis against the frat boy and threw her head back. She cut the moans of the bedroom with a rippling scream as the explosion of cum rocketed through her body and flooded the tight space inside the frat boy’s tight ass.

  Jack tightened his eyes as the brunette slammed her cock all the way and he could feel each rope pushing inside him as her shaft flexed and throbbed. He finally knew what it was like to be a perfect little submissive.

  The girl pulled out quickly as her release drizzled from the frat boy’s ass and onto the red silk panties.

  Jake felt the void deep inside him and collapsed onto the bed.

  “Now,” Vanessa said, huffing.

  “Go back to your dorm,” she demanded.

  The blonde, quick not to step on the
toes of the sorority girls any further, rushed toward the closet and grabbed his clothes.

  “Did I say you could take your clothes?” Vanessa snapped, as Kelly laughed with exhausted bliss.

  “You don’t actually expect me to walk outside in nothing but a pair of cum-soaked, red crotch less panties, do you?”

  “Kelly, get the dean on the phone,” Vanessa snapped.

  “Ok, ok,” Jake pleaded, rushing out the door as his wet ass pulsed with soreness.

  The frat boy felt his legs wobble from the relentless fucking. He smiled as he struggled down the stairs and felt the sorority girl’s seed spilling from him. He’d lived out his darkest desire with two gorgeous women.

  And best of all: he left with a pair of their panties.

  Jessica’s Secret

  “You’re good,” I said with a small laugh as I shook my head in disbelief.

  The tall, buxom blonde woman standing before me in my own kitchen had been playing me all along and I had only just now found her out.

  “What can I say? I like to be sneaky,” Jessica giggled back as she leant over the tile island counter and eyed me. As her emerald green eyes sparkled against the low-lighting, I tried to place any hint of remorse or guilt on her part – there was none. She had probably planned everything from the moment she’d moved in.

  And even though I then knew the truth, I couldn’t help but wander my eyes down below her pretty little face. How could I help it? Jessica was gifting me an immaculate view of her incredible cleavage, made possible by the two giant breasts pressed together in her little pink halter top.

  “You’re so naughty!” She squeaked, catching me in the act.

  “What? I wasn’t doing anything,” I said with a touch of defense.

  Wait a second; what the hell am I doing? She’s the one who should be defending herself. She’s lucky I don’t press her up against the fridge and fuck her brains out for what she’s tried to pull, I thought to myself. I wondered if she could read my sentiments in my wandering blue eyes.

  “So, what do we do now?” Jessica asked, shifting her eyes curiously and coupling it with a mischievous smirk. She teased her blonde curls and I swallowed hard. My heart sped just a bit, along with my breath, as I came slowly around the island and stepped beside her.

  “I think you know exactly what we do,” I growled, inching closer to this tall, drop-dead gorgeous woman in my kitchen. “You’ve got some explaining to do; but that can all be forgiven, I suppose,” I hinted.

  “Oh?” Jessica asked, feigning innocence.

  Am I seriously about to do this? I thought to myself. But I couldn’t help it. She’d teased me long enough, and drawn me into her sexy web. I couldn’t escape even if I wanted, and as conflicted as it had made me, I wasn’t sure that I even wanted to escape at that point.

  Just as I’d fantasized more than a few times before, I grabbed Jessica’s lithe arms and pushed her back against the counter. She gasped in surprise, but her eyes grew wild with life as she squeaked a mousy laugh and grinned.

  “Yeah, you like that, don’t you sneaky little slut,” I growled.

  “This isn’t about what I want anymore; it’s about making things right and settling the score,” I explained as I felt her fingers climbing up my forearm.

  “Let’s not kid ourselves, Jack. You want to know what it’s like, don’t you? Don’t tell me you aren’t the least bit curious.”

  Jessica whispered toward my ear as she grabbed my hand and pulled it down over her tight denim shorts. As she set my hand on her, I felt the firm bulge and inhaled, ready to take the dive.

  I looked into her cool, icy glare and without any more warning, pressed my lips against hers, tasting her sweep mouth before it could emit another giggle or squeak of surprise.

  My heart raced, and I tried to recall just how I had gotten myself in this situation…

  It was hard to believe it had only been two weeks since I first interviewed Jessica for the vacant room I was trying to rent out in my house.

  She had replied to my online advertisement, without any real mention of her gender. I was partial to renting the spare bedroom out to another guy, considering I was a man and figured it would just work better that way. I certainly didn’t want to make some college girl uncomfortable with the prospect of renting a bedroom in a big house occupied only by one other person, who happened to be a thirty-something male.

  When Jessica had replied, she was direct and to the point.

  “I can meet Thursday afternoon, 3 PM,” she had written in her email, before adding her phone number and instruction for me to text her.

  She had seemed to me the sanest responder to my ad. Before her, I’d fielded replies from recovering crack-addicts and a cult that needed ‘a quiet place to lay low for a while,’ as they put it. I was more than a little surprised; I lived only a few blocks from the University, and figured the room would be an easy sell. The rate was way lower than other places, and who knows, perhaps that scared most people off.

  Jessica was unfazed, even after I’d made it clear that I was a man. And by the time she was knocking on my front door that Thursday afternoon – her figure vague and unspecified in the frosted glass window of my door – it was too late to control the situation.

  Opening the front door, my eyes grew wide. My jaw hung a bit low and I instinctively ran a hand through my dark hair. My expression must’ve been obvious, because Jessica gave a small delighted laugh and a courtesy, before extending her hand.

  Without so much as a word uttered, I took her soft little fingers in my strong grip and gave her an honest but cautious shake.

  “Um, hello,” I said with a laugh of confusion. I looked around for a moment, expecting the hidden camera crew to reveal themselves. Why else would a complete knockout of a woman be standing on my front porch?

  “Can I help you?” I asked, with the question generating one or two dirty fantasies in my mind.

  “Oh, I think you certainly can,” she said with a wink.

  I have to admit; I swallowed hard at this and went to cover my jeans, as Jessica clarified.

  “My name is Jessica. I’m here for the available room for rent?” she said, batting her eyes. She seemed on the offensive, as if she figured the competition for the room were steep and she would need an extra incentive to dangle over the landlord.

  “Oh,” I laughed, shaking my head. “I’m sorry; I just, I wasn’t expecting a… woman.”

  “I wouldn’t worry about it,” she said. This of course, went right over my head until everything in this little mystery was solved.

  I squinted and cocked my head for a moment. “Are you fine with living with a man? I don’t meant to be intrusive or anything.”

  Jessica laughed and brushed down her tight-fitting red t-shirt. The top perfectly paired the even tighter blue jeans she had fitting snug around her perky little mid-section.

  “Of course,” she said. “I grew up with a few brothers. I’ve got no problems with that. And you don’t seem too dangerous.”

  The observation caught me for a moment, and all I could do was laugh. But Jessica’s eyes settled on me, looking me up and down. The expression implied she might have been doing much more than observing my clothing – perhaps even trying to figure out what was beneath them. I wasn’t about to make that bold prediction, however.

  “Well, ok,” I said, a bit nervous due to my not expecting a young woman. “Come on inside, then, and I’ll show you around the house.”

  Jessica stepped inside, her giant, perky breasts bobbing as she stepped over the doorstep and into the wooden-floor foyer.

  After giving her a small tour and trying to remain collected, I did everything in my power to keep from checking out her ass. I felt like a total asshole for being so damn attracted to her, but I couldn’t help it. I wasn’t a cover model by any means, but I’ve been lucky enough to bed many, many women. And yet I couldn’t say I had ever caught the eye of anyone as attractive as Jessica.

  I was clo
se to denying her the room, simply on the grounds that I didn’t want to deal with the prospect of having such a hot girl in my house. I was in the middle of an intensive research project at the University and I didn’t need the distraction. But, knowing full well that my own interest in Jessica was certainly not her fault, it seemed like a dick-move to discriminate on her simply because of her good-looks.

  “I’ll take it,” Jessica had said with a little giggle, after we left the room and headed back down the stairs.

  “It’s a cash thing and month-to-month, if that’s fine. I didn’t want to get too complicated with paperwork or anything,” I admitted, as we headed back to the front door.

  “Aren’t you…” Jessica squinted, her green eyes studying me endlessly. I had admittedly wondered how long until she might figure it out.

  “Are you Dr. Stevens? You’re not, are you?” She asked with an expression of disbelief.

  “Um… guilty,” I said.

  “Oh wow!” Jessica gasped. “I’ve heard about you. I saw you on that national news show a few weeks ago. This is so crazy,” she raved.

  “Do you go to the University?” I asked.

  Jessica nodded, but sighed. “I’m only taking one class at a time for the moment due to money being tight.”

  “Oh, of course; I totally understand,” I said.

  “I actually… I sort of work from home. Is that okay?” She asked with a concerned expression. Her green eyes flashed a look of vulnerability as she teased her blonde hair.

  In fact, it could have very well been a problem, depending on the type of work.

  “Well,” I started. Just then, Jessica primped her large breasts, pushing them up slightly, as if she’d been looking in a bathroom mirror before a date.

  “Um,” I said, with slight surprise.

  “What sort of work do you do?” I asked, “If you don’t mind my asking.”

  “I’m an entertainer of sorts,” she said, unable to keep from grinning. Her smile was devious and suggesting of something beyond conventional.

  “An entertainer?” I asked.

  “Yes, I… well, I review sex toys online, to be honest.”