Man to Woman

by Jane Futa

  I wasn’t sure what came over me. In one swift moment, I went from reluctant to fuck this half-boy, half-girl pop star, to ravenous. I was going to teach her a lesson she would never forget, and the thought of doing so only made me harder than before. Just before, I’d thought I was going to get to fuck the tightest pussy of my life. And now, I knew I would. There wouldn’t be anything tighter than that perky little starlet ass, and I was going to make it mine.

  My chest heaved as I grabbed Ashley’s mouth and pressed my lips to hers, tasting her kiss once more. She pulled back and moaned as I made my way down her breasts, rubbing my hands over each orb. I teased her navel and came down to the tutu, ripping it apart and off her legs.

  “Do you hear your audience cheering for you?” I asked, listening to the ambient sounds of the fans above us. “Little do they know their precious pop star is a dirty little twink, and about to get fucked by the biggest cock of his life.”

  I grit my teeth and watched as Ashley’s massive, pink cock bobbed back and forth in its hardness, wagging like a metronome atop her narrow hips. I grabbed her cock and felt the pulsing warmth in my grip. Her cock was big, but it wasn’t anywhere near my size, and I couldn’t wait to show her what she was in store for.

  My heart sped and I tried to comprehend was I was about to do. I started to stroke her cock, watching as her balls jumped up and down. The sight, though it certainly hadn’t ever done so before, made me hornier than ever. I lowered my lips down over her massive tool and felt the spongy, crested cockhead filling my mouth.

  “Oh!” Ashley cried out as her red cockhead sank into my mouth and back towards my throat. I sucked as I pulled back and sank back again. It was as if I’d done it a million times.

  Somehow, it seemed natural.

  I didn’t even think of it as a cock, so much as an extension of this crafty little slut. In that moment, it wasn’t much different than eating her out after all. I knew I was going to have a hard time explaining to myself later on, how I’d sucked off another cock. But at that point in time, it was only bringing me closer to climax as I watched Ashley’s face tighten and wince from the unbearable bliss.

  “Oh fuck!” She cried out and pulled her hips down. She tried to pull her cock from my mouth, but I grabbed it and held it there, making her endure the edge of her climax until she screamed out for mercy.

  I pulled back and wiped my mouth. “I’ve got other plans for your big finish,” I said with a grin, before grabbing Ashley’s hands and pulling her up. As she sat in the beanbag chair, eye level with my jeans, I undid my pants and pulled the zipper down.

  “Time for you to make it up to me,” I said, looking down. Ashley reached inside and grabbed my cock. The familiar bliss surrounded my girth as her lithe, warm fingers caressed my cock and pulled it out into the cool air of the dressing room.

  “Oh my god…” she gasped. I couldn’t help but grin proudly as the pop starlet flashed an expression of sheer horror at my nine-inch cock.

  “Um… shit,” she said, laughing nervously. She stroked my cock in a trance as her wide eyes remained glued to it. At one point, Ashley brought her wrist up beside my dick and compared the two, shaking her head. “It’s as big as my arm.”

  “I hope you’ve been practicing with that dildo,” I warned.

  “Um, I’ve never used that dildo. There’s no way I could fit that or… fit this in me,” she said.

  “Where there’s a will, there’s a way,” I said with a shit-eating grin. I grabbed Ashley’s pink wig and pulled her in toward my cock. “Now, what does the little pop star slut think about her body guard now?”

  “Are you going to apologize for setting me up? Did we learn our lesson?” I asked.

  Ashley nodded obediently and wrapped her fingers around my cock, stroking it as I sighed in delight.

  “You thought you would get to have some fun tonight but… turns out your going to be screaming your lungs out both on stage, and off,” I smirked.

  I pulled Ash’s head in and watched as her lips parted, sliding over my cock and just an inch or so down, barely past my head. I moaned, feeling her tight, warm wet mouth envelope the end of my cock. There was nothing sweeter than having that sneaky little tongue brushing against my cockhead.

  Ashley sucked my cock obediently, back and forth, each time bringing her mouth deeper and deeper down my shaft until I watched on, mesmerized as her effort. I caressed her breasts and looked down. I kept forgetting that she had a cock of her own swinging between her thighs. I couldn’t shake the conflict of having a beautiful little slut like her suck my cock, and yet have a giant dick swinging between her legs.

  I tried to tell myself that I was doing this purely to dish out some discipline, but I knew that it wasn’t true. I wanted her tight, clean asshole from the moment she’d popped up in front of the door. And something about the fact that I was going to exact revenge while I did it, only made it all the more pressing. I let my eyes shut as I felt her wet mouth glazing my cock and pulling me closer to climax. Finally, I pulled back and pulled Ashley’s wrist.

  “On the beanbag chair, and on your belly,” I insisted.

  Suddenly, we both turned as a knock came crashing against the door. The older woman was screaming from the other side.

  “Ashley? What the hell is going on?!” She cried, banging on the door.

  “I’m…” Ashley started to answer as I spread her legs apart and sank my mouth onto her tight little asshole.

  “Oh fuck!” Ashley screamed out.

  “Ashley? I didn’t hear you; what did you say?” the older woman shouted from the other side of the door.

  “I said… I’m about to come,” Ashley cried back. I didn’t know to whom this little remark was directed at. All I knew was Ashley’s sweet little asshole tensed as I rimmed my tongue along it, tasting her skin and growling with hunger as I ran my finger closer and closer to the little hole.

  “Oh!” Ashley moaned. The older woman finally gave up and there was silence again, save for Ashley’s gasps of pleasure.

  I grabbed her cock and brought it back toward her ass until it was pointed straight down, as I slid my finger inside her. I’d seen a few porn videos before, suggesting pulling the cock down when fingering someone’s ass – not that I’ve ever gone looking for that sort of thing.

  I stroked Ashley’s cock and slid my finger deeper into her warm ass as it opened up around me. When I couldn’t take it any longer, I grabbed my cock and rubbed the head against the slick little asshole.

  As Ashley finally caught wind of my act, she turned back and cried softly, “Fuck me. Show me how bad I’ve been.”

  “As you insist,” I growled, spanking her ass harsh as I thrust my cock just inside her ass. As the warm opening parted around my girth, I threw my head back and tried to process the unbelievably tight hold the little slut’s ass had on my dick. I thrust slowly and watched in delight as Ashley’s body tensed and she balled parts of the beanbag chair in her fists.

  I shook my head, unable to believe that I was fucking another guy’s ass. Only, I wasn’t. Ashley was all woman, and just as she’d explained to me, she simply had something extra. I’d never considered it before, but it made enough sense to me. And with her tight, warm ass wrapped around my cock, I would have believed anything she told me. I pumped slowly toward her center, watching as she writhed and listening as the pop starlet’s sweet voice rang out with cries of bliss.

  I had to believe her when she said she hadn’t ever practiced with the dildo, as tight as she was. I rammed my cock deeper, still; this was punishment, after all. And ever little moan and cry was like music to my ears.

  Again, suddenly, there was a loud and impatient banging on the dressing room door.

  “Ashley, come on; the crowd is getting angry,” the large man from earlier called in a low, authoritative tone.

  “Just a moment,” Ashley said, faking a tone of composure as best as she could. I shoved my cock deeper inside just then, eliciting a loud cry from the p
op star, and grinned devilishly.

  “What’s going on in there?” He called through the door.

  “The body guard is helping me fit into something,” Ashley called, as I thrust my cock balls deep and watched her tight little backdoor pussy split around the base of my thick cock.

  She cried out loud, throwing her head back, as I pulled my cock back and pumped mercilessly. “I’m going to…. Fuck, I’m going to cum!” She cried out. She hadn’t so much as touched her cock, what with me pulling it down and out of her reach.

  Yet as I pounded her ass, I felt her entire body tighten and pulse around mine. Ashley’s sweet, high tone came crying out as her cock shot hot, white ropes toward the floor and against the side of the beanbag chair.

  “Fuck me!” Ashley cried out as her pink wig tossed to and fro. I reached forward and grabbed her hair, pulling her head back. “You want me to fill you with a real man’s cum?” I growled into her ear.

  “Please,” Ashley begged in a whisper. I felt my skin against her warm, sweat-sheened back as our bodies slapped against one another. I slammed my cock deep inside her one last time as the familiar fire built impossibly strong in my core.

  “Oh… fuck!” I growled. My voice split through the cool silence of the dressing room as my cock pumped endless ropes of hot seed deep inside the pop star’s dirty little ass. I couldn’t stop, pounding over and over until I felt as though my mind had rocketed a thousand miles above the Earth, right into outer-fucking-space. The mindless ecstasy rippled through my body like a wildfire, leaving my legs useless as I collapsed against Ash’s hot little frame.

  With my cock still deep inside her, pumping the last few weak loads into her sweet pussy, I tried to catch my breath. I leant down and whispered, “Maybe I’ve made myself clear, now.”

  Ashley’s sweet vanilla scent was hinted with her sweat as her lungs inhaled and exhaled wildly. She nodded and kept quiet as I pulled my cock from her.

  “Now,” I said, spanking her ass, “get back on stage and finish your show.”

  Ashley hurried over to her mirror and dressed herself as she made small glances back toward me. “I need somebody to escort me back to the stage,” she said.

  “I guess I could do it,” I said, as I fanned myself with a towel. Ashley laughed and apologized for trying to set me up.

  “You understand why I did it though, right? I mean, you almost didn’t touch me when you found out about my little… surprise.”

  “True,” I said. “Good thing you tricked me into it.”

  I zipped my pants back up and turned to Ashley. “So, do I have the job as your regular bodyguard?” I knew the gig was only for that one show, but to my amazement, Ashley nodded.

  “You’re coming with me on the rest of my tour,” she smiled. “But be warned, I’m kind of wild.”

  “That’s fine,” I said. “I’ll just have to keep you in line somehow,” I said, tapping my finger on my chin as we both laughed and patted ourselves down on the way to the dressing room door.

  Her Little Secret

  “Pretty please!”

  Melissa pleaded into her smartphone’s tiny camera screen. “She just needs a place to stay for, like, a week tops,” she added. “I’ll make it up to you – I swear.”

  Edward sighed with frustration and looked at the grainy image of his sister stretched across his laptop screen, as she sat in suspense. Though they were twelve-hundred miles apart, Edward could somehow feel the tension circulating in his sister’s room.

  Edward stroked the stubble on his jaw and shifted his dark eyes from side to side as he tried to decide whether to let a complete stranger crash on his couch for the next week.

  “I don’t know. I’ve never even met her,” he answered.

  “Chelsea is super friendly, I swear. And um,” Melissa continued with a mischievous grin, “she’s really pretty, too.”

  “Melissa, please,” Edward said, brushing his hand through his golden blonde hair. “I’m not hurting in the dating department – not that I’m about to divulge any details to my own sister or anything.”

  He laughed, but Melissa remained stolid. She was dead set on finding a place for her friend to stay, even if it meant groveling at her cocky brother’s feet.

  “Come on! You live in that giant house, all by yourself,” Melissa said, growing frustrated with Edward’s hesitation.

  “Hey, it’s my house. I can keep it as empty as I want,” he shot back. He couldn’t deny the defeated expression in his little sister’s face, though. He already knew from the get-go that he would let the girl stay with him for the week, but he wanted to let his sister dangle for a little longer.

  “I just don’t see what’s in it for me,” he said with a devilish grin.

  “Does there have to be something for you? Can’t it be because you love your sister that much?” Melissa asked with a doting smile.

  “Fine,” Edward said, shaking his head. “I can’t believe I’m agreeing to this. This is crazy.”

  “You act like she’s a serial killer or something,” Melissa argued.

  “Well, you never know. Didn’t you see that show on TV the other night?” Edward started. “Hell, I forget what it was called; it was playing in the background at the pool hall or something. Anyway, this guy let’s a stranger shack with him for the week and bam, next thing you know, he’s sleeping with the fishes.”

  “He’s… what? Sleeping with the fishes?” Melissa said, squinting into the camera on her phone.

  “Never mind,” Edward dismissed. “Look, I’ve got a date tonight. I was supposed to leave like an hour ago. When can I expect this weary traveller on my doorstep?”

  “Chelsea is going to be there tomorrow afternoon around four. She’s got your number and I told her to text you when she’s out front.”

  “All right,” Edward sighed. He figured that four was late enough to avoid any awkwardness if his date had decided to stay the night.

  “Thank you, thank you, thank you!” Melissa said, gesturing wildly as the pixelated screen failed to keep up and became too choppy to make out.

  “Ok well, bye sis,” Edward said, closing his laptop and putting the obligation out of his mind for the next several hours.

  Unfortunately, he’d forgotten entirely that he was expecting company. The only reminder came when he woke the next morning to his phone vibrating endlessly on his nightstand.

  “What the…” he said, shaking his head lazily and stretching. As he went to reach his arms around the brunette from the night before, she pushed Edward off and laughed. “Ugh – morning breath!”

  “Kiss me,” Edward insisted. The girl instead shifted her eyes to his phone. “Shouldn’t you get this?”

  She picked up the phone and saw the words: IT’S CHELSEA. I’M OUT FRONT.

  “Um, who is Chelsea?” She asked, and sat straight up with the sudden scrutiny of a distrusting wife.

  Edward caught sight of the perfect tits that he’d waited a few weeks to taste, as they slid out from the bed sheet draped over her. He tried to place the name, but couldn’t come up with an answer.

  “You said you were single, you slime ball!” the girl said. She jumped from the bed, her naked, tanned body shimmering against the morning light of the large bedroom window, and dressed herself.

  “Babe, I’m telling you the truth. I don’t know who any Chelsea is,” Edward said. He shifted his eyes from side to side, trying to think of a face, until he remembered the conversation with his sister the night before.

  “Oh… wait a second,” he said, with an “ah-ha” moment of revelation.

  “You’re a pig!” The woman said, throwing her panties at Edward’s face.

  The blonde stud smiled and held them against his cheek, before the woman balled her fists and stomped her feet. “Ugh, I didn’t mean to throw those! Give those back!”

  “Wait just a second. You’re not going to hear me out; seriously?” Edward asked, annoyed.

  “I don’t want to know anything about t
his Chelsea woman,” she huffed, before snatching the silky pink thong from his hand.

  “Babe, it’s just some girl I’m letting stay with me for a while,” Edward said. His dark eyes widened. “Shit, I mean… Wait a second babe - that came out wrong.”

  “I think I’ve heard enough,” the woman said, grabbing her heels and storming out of the bedroom.

  Edward sighed and fell back onto his bed. He stared up at the ceiling as his naked, muscular chest rose lazily with each breath. The bedroom as silent and calm, and for a moment, he smiled, despite the events of the past few moments. “She’ll be back,” he whispered to himself and curled his lips into a grin.

  “I wouldn’t be so sure.”

  Edward turned to see a tall, pale, dark-haired eighteen year-old standing in his doorway. The girl was slender and propped on her hip as a suggestively short and red plaid skirt rounded her waist, along with a tight, black shirt that did little to hide her giant breasts. The girl’s blue eyes sparkled in the sunlight breaking through the window.

  “Whoa!” Edward said, clutching his bed sheet and pulling it from just above his cock, up past his hard abs and to his chest.

  “What the hell do you think you’re doing?” He called and sat up.

  “Hi, I’m Chelsea; Melissa’s friend?” The girl stepped into the room and smiled as she looked the stud up and down. Her eyes started at the end of the bed closest to herself and travelled upward from Edward’s feet, to his face. He noticed her eyes particularly slow to move past the mound between his thighs as it sat beneath the white linens.

  “I figured that,” Edward said. “I just… who let you in? You can’t just go barging into random people’s houses,” he lectured.

  He shook his head, realizing that he was showing his age. Though he was only pushing thirty, he felt as though he was living in a different world from the eighteen year-old.

  Amid his frustration, he couldn’t help but look over the gorgeous teen. His sister had mentioned that Chelsea was cute, but this girl was something else entirely. The girl seemed hypnotizing to him, so much so that he felt that familiar tension beneath the sheets, and quickly maneuvered to hide his swelling, thick girth.