Man to Woman

by Jane Futa

  “Oh!” She cried out. Her face tightened as the sting swelled from her ass and down her long, shaved legs. Edward was coming into his own now, handling her like he would any other girlish slut.

  He grabbed his ass and pulled it open for Edward. The alpha grinned with amusement and grabbed his cock, coming up to the edge of the bed.

  The blonde inhaled deep and, as his heart sped, lined his cock up with the tight little ass. He shoved slowly and watched in sheer bliss as the slut’s little ass munched his cockhead in. The sensation of her warm, wet little canal made him weak as her ass split open around his girth and she gasped with shock.

  “Oh!” Chelsea cried. Her eyes shut tightly and she tried to comprehend just how this giant cock was going to fit inside her. But there was no difference in her comprehending it or not; it was happening whether she could stand it. Edward was too hungry, now. His cock dove deeper and Chelsea felt the slow, sore burn in her core as she opened up around him.

  “Fuck,” Edward said, chewing his lip in ecstasy as the tart’s tight little ass gifted him the most incredible, warm sensation of his life. He sank his cock deeper still, unable to fight his own impatience to claim every inch of her ass.

  “Oh!” Chelsea cried again, as Edward came down and kissed along her shoulder, before moving down to her nipples. There, he bit each of them, quick and without warning. He smiled each time the deceptive little sissy cried out in reply.

  “This is what you wanted all along, isn’t?” Edward asked in a growling whisper. “But you didn’t think I’d fuck you if I knew the truth. Little did you know that I’ve got no problem fucking a femboy pussy like yours.”

  “Mm,” Chelsea moaned, rolling her eyes back and writhing with bliss as Edward’s thick cock drove all the way inside her, stretching her to her brim. As his girth massaged against her prostate, she felt the tease behind her cock. She was going to explode if he continued anymore.

  As if he could sense it, Edward pulled his cock back, before driving it inside her again, faster and harder than before. He smiled in delight as the bliss swelled around his own cock and his balls slapped against the edge of the bed. He felt his body growing tense and ravenous for release, but he wasn’t about to act until his fuck toy came first.

  “I’m going to make you shoot like a geyser,” Edward said. “That should be a fitting punishment for being such a little whore.”

  “Please,” Chelsea cried, balling the bed sheets in her fists and writhing. Her breasts pushed into the air as she gasped for breath. She hadn’t once touched her cock, and yet the build continued anyway, as if she’d been stroking it nearer to climax.

  As her ass tightened intensely around the blonde stud’s massive tool, she felt the uncontrollable fire pushing from her core. The power thundered down her shaft and rocketed out, leaving the sissy slut contracting from head to toe as she shot one white rope after another over her breasts and face.

  Edward slammed his cock mercilessly as he saw cum, as if each pounding thrust were squeezing every little drop from the teen. “Fuck!” Chelsea screamed out, as cum drizzled over her tits and even hung over the edges of her opened blouse.

  Her body was thrust back and forth as Edward leaned over her and slammed his hips into hers. He’d tasted her pleasure and was hungry for his own, now.

  “You gorgeous fucking whore,” Edward said, grabbing Chelsea’s jaw and pressing his lips against hers as he slammed his cock deep into her asshole. The base of his cock slammed against her balls, each time eliciting a hum of pain from Chelsea’s throat. He didn’t care – it was his turn. He pounded over and over, driven by the sound of their sweaty skin slapping together and parting, only to repeat.

  He inhaled her warm, tropical scent before biting down on her nipples and thrusting as deep as he could into her ass. “I’m going to fill you so full you’re going to need the morning-after pill, you dirty little whore.”

  “Fill me,” Chelsea breathed. Her body clenched as Edward thrust and felt the burn swelling throughout his body. The sweet, arrow of weakness slid up his thighs and settled at the base of his cock, before he felt the explosive pressure marching down his shaft.

  “Oh fuck!” He groaned as his legs grew weak and his cock pumped an endless stream of seed deep into the sissy teen. “Ah… fuck!”

  His rhythm broke up until he could only thrust himself as deep as possible and let each muscle in his body give in to the chemical bliss. Chelsea smiled as the alpha’s massive tool flared deep inside her, depositing his warm release. She had brought the strong stud to his knees and gifted him to pleasure of a lifetime and, if she were to be honest, he’d done just the same for her.

  Edward kissed between Chelsea’s breasts and caught his breath as he pulled from her ass slowly. As he pulled out, his powerful tool continued shooting. Chelsea couldn’t help but laugh with satisfaction as he slapped her ass and collapsed next to her on the bed.

  “Fuck,” he breathed. His wide chest rose and fell with each long gasp and the dark-haired teen curled up in his large biceps. She had never felt so at home.

  “So, you won’t tell on me to your sister?” Chelsea asked.

  “What? About earlier? No way,” Edward said with an expression of exhausted bliss. “I think I can let it slide.”

  Chelsea laughed and asked, “Did you enjoy yourself?”

  Edward nodded. “I don’t know why I was so hesitant at first,” he said, before reaching down and grabbing Chelsea’s dick. “This is way more fun than any other girl has given me.”

  Chelsea couldn’t help but smile proudly at this. She felt a sense of worry overcome her though, before asking, “So I can still stay here for the next few nights?”

  “I don’t know about that,” Edward said. This response left Chelsea panicked for a moment, until Edward clarified. “That is unless you can somehow convince me otherwise.”

  Edward laughed as Chelsea playfully slapped his chest and he wrapped his arm around her. Suddenly, Chelsea had felt at home for the first time.

  Tennis Trans Trio

  “Sophie, for the last time; I’m not about to get involved.”

  I sighed and I scrolled through my phone, trying to ignore my girlfriend’s glaring green eyes as they shot daggers at me from the next desk.

  “Brad, she’s cheating; I just know it. I don’t know if it’s steroids or what, but she’s such a phony, and she’s running my chance at a team captain,” Sophie continued. Her indignant voice twitched in frustration as she explained for the millionth time, how the new girl on the girl’s tennis team had been outperforming everybody.

  “The Swedish girl, right?” I asked, taking a passive interest.

  “Yes,” Sophie said, brushing a hand through her red hair and huffing. I turned to look at my sweet girlfriend. She always looked so damn cute when she was angry; her freckles and her green eyes always got the best of me. This time was no different.

  “Fine,” I relented, setting my phone down. “I’ll talk to coach tomorrow.”

  Sophie reached over and gave me a giant hug, as our professor cleared his throat and turned toward us.

  “Mr. Stevens, Ms. Benedict; is there something you would like to share with the rest of the class?”

  I sank into my chair as students chuckled behind us and shook my head, before turning to Sophie, who now flashed her apologetic eyes at me.

  “What am I supposed to say, though?” I whispered, watching back towards the front of the room to make sure our professor hadn’t checked in on us again.

  “Just, I don’t know. Make everybody do a drug test or something,” Sophie suggested.

  “Sophie, I’m the assistant coach on the college tennis team; I’m not a dictator,” I reminded her. I exhaled as my heartbroken girlfriend started to drag her finger sensually over my arm, running it up my long black sleeve and settling it at my chest. She ran her fingertip in circles against my chest as she leant over and breathed warmly against my ear.

  “I would make it so worth your wh
ile, Brad,” she sighed with a slight moan.

  Fuck if that didn’t get my cock hard from zero to sixty. Although Sophie and I had dated for well over four months, she still hadn’t so much as given me a peek at her pussy. The closest I got was a quick flash of her cotton panties, which gave the slightest hint of the trimmed red bush just beneath them, along with a subtle camel toe just beneath it. The sight always left me hard and howling for more, but Sophie always cut me off. She was dedicated to making team captain of the tennis team.

  “When I do that, then I can relax a little,” she would tell me, each time I ran my hand over her naked thigh and climbed inside to feel the warmth pulsing between her legs. She would grab my hand and halt its journey inside her yellow tennis skirt, and my balls would practically throb with pain. She was the first girl in fifty that I hadn’t fucked since getting to college, and I was growing seriously impatient, especially considering she had joked that she originally took an interest in me because she thought it might help her tennis career.

  “After a while I realized what a cute jerk you were, after all,” she said with a teasing smile.

  A quick slap on her ass would send her squeaking and smiling, and telling me just how wet she was. But she would always return with something like, “I need these loose legs out on the clay.”

  But after begging for me to investigate the suspicious performance of her new teammate, she decided that it was time to make it worth my while.

  “Fine, we’ll do drug tests next week, I guess,” I said, offering to talk to girl first.

  Sophie bit her lip and scrunched her brow. “I don’t know,” she whispered. “She’s so pretty. I don’t need you eyeing another girl.”

  “Come on,” I shrugged. “It’s the only way.”

  “But you haven’t even see her; you don’t know,” Sophie said. “Maybe if you’d been here this past week to see for yourself, instead of running around Europe,” she added with a slight nag.

  “Babe, I was on tour with the men’s team,” I reminded her. “For the last time; I wasn’t sleeping around. I’ve told you a million times, you’re the only girl for me.”

  I tapped my pen against the desk, admittedly losing my nerve just a bit. I turned my mind to the girls I’d seen in Europe; there had been some seriously beautiful women. And when Sophie mentioned that her new tennis rival happened to be a nineteen year-Old Swedish blonde girl, well, I knew I wouldn’t need too much convincing to pay her a visit on the court.

  “So when are you going to go talk to her?” Sophie asked, breaking what had been maybe three minutes of concentration on the biology lecture.

  “Sophie,” I said, turning my head and exhaling. “I’ll go this afternoon, if that will make you happy?” I said.

  “You should. And don’t fuck around. She’s kicking everybody’s asses on the court and I’m set to play her next,” Sophie reminded me.

  Turns out, the Swedish girl was good. I showed up to the court that afternoon, to find the rest of my coaching staff watching the girl in amazement, as she outperformed one of our best players.

  “She’s our new secret weapon, Brad,” Coach Collins said. The sixty-year old approached, his grey eyes beaming with excitement as he placed his hand on my shoulder.

  “We’re winning regionals this year, at the very least,” he said with a quick laugh of enthusiasm.

  “No kidding,” I said, rubbing the back of my neck as I squinted in the afternoon summer sun and watched the tanned girl jump from one end of the court to the other. She owned the clay, dancing about and not letting a single serve pass her by without smacking it hard across the net. She was the real deal, but something did seem a bit off about her.

  “She’s tall,” I said, noticing the girl stood probably close to my own height of over six feet.

  “Tall, strong, focused. You name it, she’s got it. I’ll bet she could kick every one of the boy’s asses, too,” Collins called before stepping onto the court and blowing his whistle.

  “All right ladies, that’s thirty-love. Julia; nice hustle. Tammy, I wish I could say the same.”

  I watched the court. My eyes studied the blonde girl from behind my sunglasses. She bent over and grabbed her water bottle, spraying it against her mouth. Every damn movement of hers was both graceful, and assured. She had zero insecurities, it would seem.

  As I watched her, I saw her suddenly turned toward me. She shifted her cool blue eyes across the court, right to my own, and let them sit there. After a moment, she cracked a grin and flashed a small little wave toward me.

  “Brad? Come on over here and meet Julia,” Coach Collins said, calling from across the court as he neared the tall Swedish girl.

  I stepped over, and to be honest, my heart jumped just a bit. The girl pulled the band from her hair, and let it fall out of its pigtail, into a long flowing mess, before retying her hair and putting it back up. She shook her hair from side to side and with a quiet motion, turned her eyes to watch me approach her and Collins.

  I looked over to the stands to see Sophie as her own green eyes glared with jealousy.

  “Brad, this is Julia, our new Team Captain. Well, I mean, our new Team Captain, pending the try-outs next week, of course,” Coach Collins said with a wink and a smile.

  “She’s still got to beat Sophie, Coach,” I reminded him as I kept my eyes on the blonde girl.

  Somehow, her complexion was even more other-worldly from up close. If she’d been terrible at tennis, she could have found more success as a super model, anyway. And yet, she was the best girl on the team.

  “Hello,” Julia said, in a soft voice. Her lips curled into a smile, and I cocked my brow. The girl had perhaps the deepest voice I had ever heard on a woman.

  “Whoa,” I blurted.

  “Uh,” Coach looked at me as if I’d made the faux pas of a lifetime.

  “Brad,” Coach laughed nervously, “You okay?”

  “What? Um, sure,” I said, returning to reality.

  The girl was surreal – unlike any I’d ever come across. She smiled and extended her hand, and I met her in the middle. As I enveloped her hand in mine, I was struck, both by how soft her fingers were, and how damn strong her grip was.

  “Hello; nice to meet you, Julia. I’m excited to have you on our team,” I said.

  “I am happy to be here,” she said.

  “Your English is very good,” I remarked.

  The girl seemed put off by this – almost insulted or at the very least, uncomfortable. “I have been here for a long time.”

  “Oh, I’m sorry. I was just… surprised, was all,” I said.

  “Well, I’m going to leave you two to get acquainted. We’re packing it up for the night, Brad. You’re closing up again, right?” Coach Collins asked.

  “Um, yeah. I’ve got the key. You guys go on ahead,” I said, waving.

  “So, listen, Julia. I was wondering if you had a moment to talk.” I asked.

  Julia laughed nervously and nodded. “I have anything for you, Mr. Stevens.”

  The response sent a wave of tension toward my waist; I couldn’t lie. Something about the girl’s assuredness left me hungry for domination. Of course, I was a coach and I was committed, first and foremost. I wasn’t a player, and I certainly wasn’t going to go hitting on my players anytime soon. As I reminded myself of this, I turned back to see Sophie watching from the bleachers, and remembered what I was there to do.

  “Well, that’s good. Because I need you to be honest with me about something,” I said. I turned and saw that most of the group had already left for the evening. The tall blonde brushed down her small tennis outfit, turning her tanned nose down and patting the small area of skin just above her cleavage. Her breasts were smaller, but round and inviting, perfectly accentuating her tight and subtle figure.

  “What is it?” Julia asked, starting to walk away from me.

  “Hey, where are you going?” I asked.

  Julia only laughed and flashed a ‘come hither’ motion
with her finger. “I must go to the showers, silly. You know that.”

  “Well, yeah, but I’m not coming in with you,” I said, eyeing Sophie.

  “Why not? You’re my coach,” the girl said with a curious smile.

  “Julia, I’m not sure how they do tennis in Sweden or anything, but…” I hesitated, rubbing the back of my neck and biting my lip at the images forming in my mind. The girl bent over and grabbed her water bottle, leaving her round, perky ass in full view of the setting sunlight.

  Sophie came down from the bleachers and started toward us as her long, red hair brushed in the breeze.

  “Hello Sophie,” Julia said.

  “Hi Julia. Have you met, Brad? My boyfriend?” Sophie asked with a hint of possessiveness in her tone.

  Julia giggled at this and nodded. “Yes. You’re a lucky girl,” the blonde said, keeping her eyes locked with mine.

  “Coach, I will be in the showers if you want to talk,” Julia said, sneaking away as Sophie grabbed my hand.

  “Well?” Sophie asked.

  “She didn’t give me a chance to talk to her yet,” I admitted.

  “Ugh. See? She’s hiding something big, I just know it,” Sophie stomped her tennis shoe into the clay.

  “Babe, the moment I asked to talk she took off to the showers. She wanted me to follow her,” I said.

  Sophie, to my amazement, was standing there with her eyes hanging on mine. “And? Why didn’t you?” She asked.

  “Babe, you know we don’t go in the showers with you guys. That’s highly inappropriate,” I reminded her.

  “Everybody is gone, and she’s inviting you,” Sophie answered, as her smooth lips curled into a disbelieving grin.

  “How is my lady’s man of a boyfriend not be rushing to the showers right now?”

  “Oh, so now you’re calling me soft for being considerate of your feelings?” I asked with a touch of challenge.

  Sophie snuck a hand down over my crotch as she lifted herself against my body and kissed my cheek. The moment her lips touched mine, her hand rubbed over my cock and send it into an uncontrolled rise.