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Bittersweet	By : whitemonarch Category: Supernatural > Het - Male/Female Views: 3946 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: This a work of fiction based off Tv's Supernatural. I don't own Supernatural, and I make no money from this story. This is only for fun!

Chapter List
- 1-Bittersweet
- 1
Bittersweet
Sam could see him now. Spotlighted under the bar lights, surrounded by a nicotine fog, Dean sat with his back to the pool tables and his boots pointing toward the door. A harlot; hair painted in shades of red and brown with nails the same hooker shade as her lipstick, was speaking with him. Dean looked like he was just on the edge of intrigued and bored to death. The woman in front of him could be a good lay but getting her in bed might not be worth the trouble.
Sam snorted at the scene and his fingers twirled faster in the new ringlets of his hair. With a sigh he tucked his legs under him, small skirt inching up and framing his muscled thighs. Being turned into a girl had its perks. The curse said Sam would be ‘Samantha’ for around three weeks. It worked out well enough for him. Stanford was on break, Jess would never know, and Sam had ample amount of time to put his plan into action.
They hadn’t played this game before. It was too dangerous. He knew Dean though, knew how his brother used to watch him as they moved around, play fighting in the afternoon sun until they were both drenched with sweat and panting into each other’s ears. He knew then that Dean liked to get manhandled. Sam also had a feeling that it was something Dean didn’t know about himself. He planned to change that tonight.
Downing the last of his whiskey, Sam stalked over to the hunter. With his arm wrapping around Dean’s middle he flashed all his teeth at the woman before him. “Why don’t you take a hike darling? I think he’s looking for a little more than what you can give him.” Sam leaned against the muscled body beside him and let his painted lips slide into a wolfish grin. Dean spared him a startled glance.
“I think she’s right sweetheart.” He finally answered, throwing the girl an apologetic smile. Dean turned back to Sam as the woman left, defeated. “A little more?” He questioned, reaching to grab a swallow of his beer. Sam grinned and leaned forward, new, soft breasts resting just on top of the counter, inviting Dean to give them a good long look.
“Oh yeah,” Sam smirked, watching as Dean hesitantly met his eyes. His brother was either creeped out or turned on. Sam was betting on both, but Dean had done worse for himself. Pushing it a little he laid his hand on Dean’s knee. When his brother didn’t move away Sam began slow slide up the inside of Dean’s thigh. “How about you and me get out of here? I have a motel room up at Langston Lane. We could get comfy…I could tell you my name and then make you scream it.” Ok, so maybe Sam was going a little far but Dean seemed to be eating it up.
Threading his finger through one of Dean’s belt loops Sam tugged, hard. He noted Dean’s sputtering, clumsy response with satisfaction. His brother was half on his bar stool, half off and there was a blush creeping up his collar. Embarrassed and turned on, Dean nodded his acquiesce. With a small smirk, Sam continued to tug Dean up and into his arms. Slender hands rested on Dean’s hips as he rose up on tiptoe for a kiss. His brother met him for it. “Come on,” Sam whispered against the shell of Dean’s ear, delighting in the shiver that ran down his spine. This was going to be a fun night.
***
“You’re driving” The girl called from in front of him. Dean couldn’t believe his luck. Tired, interested eyes flashed up again to the bouncing skirt before him. It was her aggression and confidence that hooked him. He’d never come up against that kind of thing before and it had him ready to go before they’d even gotten started. Normally he was the one whispering sweet nothings into someone’s ear. Who knew he would enjoy it just as much? Ok, he probably should have been worried, but Dean had done stupider things.
“Like the ride?” He asked as he crept up along side his baby.
”Like the breathing one better. Bet you don’t purr as well as she does though.” Unsure of the correct response to that Dean directed his attention to getting in the car and getting it out of the parking lot. He was trying really hard to ignore the faint blush creeping up his cheeks.
“What’s your name?” He finally asked.
“Sam- Samantha,” The woman breathed into his ear. Her hand found his thigh again and he let out a gasp. Whether it was from the motion of her fingers on the inseam of his pants or the sound of her name Dean didn’t actually know. “You?”
“Dean.”
“A pretty name for a pretty boy.” She sucked Dean’s ear into her mouth, hand splaying across his groin at the same time. Dean let out a whine as he arched into the touch. What the fuck is wrong with me? He berated himself as he gulped in deep breaths to calm his nerves.
“You wanna know what I’m thinking about Dean?” The words ghosted over the moist shell of his ear, making Dean shudder at the tickle. He could only shrug and try and keep his attention on the road. “I’m thinking about this,” She breathed, rubbing her palm in a slow circle over his cloth covered dick. “Thinking about what it will look like wrapped up in a pair of my panties. Slick tip poking over the waist band, leaking into my hand as I stroke you through the silk. Would you like that?” Dean was really blushing now. He sped the car up. If he didn’t get to the motel soon he was going to blow.
“You’re really pushy.” Dean mumbled. His hips jumped up into her hand.
“You like it.” Sam gave him a squeeze and grinned. “I can see it written all over your face. You’d do anything I tell you to right now.”She leaned herself against him, perky breasts pressing against his rib cage. Dean couldn’t wait to get his mouth all over them. He licked his lips just thinking about it. About that time her hand dipped over his cock. Her fingers tugged down his zipper and slid the button from its hole. “Look at you.” She grinned.”So hard for me. You better get me home quick or I might just have to blow you right here.” Dean could hear the smirk in her voice. As good as that sounded, he’d probably kill them both if she sucked him down right now. Thankfully Samantha was quiet the rest of the way to the motel. Even as she kissed at his neck and pawed at his jeans, she let him try and concentrate. As he finally pulled into the gravel parking lot, panting and aching, he felt the first rumbles of nervous laughter bubble up from inside him.
Sam straightened her skirt and smiled. “Better button back up. You can’t be twitching and leaking all over the parking lot.” She chuckled and shut the door. With her skirt bouncing again she headed off to the room. Dean straightened up and scrubbed a palm over his face before following. He’d already decided he’d gotten in over his head; he’d also decided he was going to see this through till the end.
Dean had barely gotten in the door before his new friend was slamming him up against it. Strong arms for chick; was all he could think when she pushed herself up against him and began to rub his crotch. Dean let out a little moan as she squeezed him and slid a leg up between his. “Jesus,” He huffed out between red, bitten lips. “This is supposed to be my job.”
“Not tonight sweetheart. Tonight I’m going to take care of you.” Damn her for using his kind of endearment against him. She began assaulting his neck with her tongue. He was melting under the onslaught. His fingers clutched into her shoulders as she dropped to her knees and pulled him out. He got two strokes and a lick in before his breath caught on a gasp and he was coming all over her hands and lips his own fists banging the door behind him. Dean almost died when he looked down at her. Her expression was light, amused, but determined. With sparkling eyes she wiped her lips on the back of her hand.
“Sorry,” He tried, voice fucked out and edging on confused. He hadn’t come that quickly in years.
“No sorry,” She licked him and smiled. “You were a bad boy. You didn’t wait for my permission. Now you have to be punished…”
“What?” The word barely passed from Dean’s lips before Sam was up and pushing at his shoulders. His pants fell to his ankles and he kicked them off before landing flat on his ass on top of the bed. She was crawling on top of him before he even knew what was happening.
***
“Dean, Dean, Dean” Sam muttered, shaking his head. He closed his eyes, enjoying the feel of his brother’s body beneath him. “You just don’t know how to play this game yet, do you?” He reached up and tugged off the top he’d been wearing. A smirk spread across his features as he watched Dean’s eyes widen and land on his breasts. “I call the shots,” He continued. “And I get to say when you do what. If you do something right you get rewarded. If you do something wrong…” Sam trailed off and straddled Dean’s chest. He knew his brother could feel the wet silk sliding against him. “Hold your hands there.” He murmured, pushing Dean’s fists down against the blanket underneath him.
“What happens if I do something wrong?” Dean asked breathlessly, watching as the woman moved higher up on his chest and grabbed at the headboard.
“You get smothered.” She answered, lowering her panty clad crotch down to Dean’s face. Startled, Dean sucked in a breath. Instantly he was overwhelmed by her scent and thrown off by the feel of her juices soaking through the fabric and slicking his chin. He’d never been one to back down from a challenge though. Besides, he was beyond turned on and his dick was quickly twitching back to life.
Separate from the hot need flowing through him, he was still unsure of how to feel about this. Still, he took a deep breath and licked out. It took him a movement but he found her clit through the fabric and sucked her gently, tongue dancing out to pass over her entrance and lick over the skin peaking out from under the sides of the underwear. He slurped, sucked, and tongue thrusted until she was panting and moaning above him, grinding into his face, barely giving him enough time and space to breath. For some reason though, in spite of that feeling, Dean felt a glow of pride as she hit her first orgasm and let out a sigh. A memory kicked in. He knew that sound, but just as quickly he let it go. She was kissing him, praising him, and licking her own slick off his face. Damn if that wasn’t the hottest thing yet.
“Good boy…” Sam praised. Dean was responding way better than he’d ever hoped. “Keep your hands still.” He reminded Dean, shirking his panties and pulling Dean towards him. Slowly Sam slid the soaked fabric over his brother’s legs and up to clutch at his leaking dick. Dean thrashed a little at the feeling, eyes wide and questioning. Sam just smiled and kept his promise, licking Dean’s tip until his brother was moaning and bucking up against him. Dean was good through. His fingers stayed white knuckled in the sheets. Sam couldn’t help but wish he was himself. He wanted to know what Dean would do if he knew it was his little brother going down on him, driving him crazy. The thought made him redouble his efforts.
“I-I fuck! Can I come please?” Dean was shaking. His eyes were squeezed shut tight and his face was pulled into a grimace of pleasure.
“No.” Sam answered with a laugh, sucking him down again as Dean’s eyes opened wide and he let out a howl. His brother’s hips bucked into him and Sam just sucked harder.
“Please…Please. Fuck. Please let me come.” Damn Dean begged pretty. He learned fast too.
“Please what?” Sam asked, kitten licking the tip of his brother’s cock and the bundle of nerves just under it. With a smile he dipped his tongue into the leaking slit. Dean growled, throwing his head back and pounding his fists against the bed, kicking at the sheets.
“Please…mistress?” Dean tried. He shuddered as he said it. “Please Mistress! Let me come. I’ll be a good boy! Fuck I’ll do anything you want me too. Just please let me come.” Dean’s dick jumped in Sam’s hand and he let go with a little satisfied smile. His brother was made to do this. For all his swagger and natural dominance, Dean was made to beg.
“Fine,” Sam finally answered. “But you have to do it. Come on baby,” Sam said holding Dean’s thighs apart. “Show me how you like it.” It took him a second for him to get with the program, but before Sam could say anything else Dean was gripping his dick and jerking it. It only took a couple of stroke before he was coming all over himself with a cry. Sweat drenched and exhausted, Dean collapsed against the blankets.
“Holy shit.” He moaned, throwing his arm over his face.
“I’m not done with you yet.” Sam hissed dangerously, licking up the white blotches on Dean’s stomach.
“Fuck you. You’re going to kill me.” Dean answered, watching her, wishing he knew what she was thinking.
“No. Just going to ruin you for every other woman.” Sam winked and slid herself between his knees. “You’ve been a good boy, but now it’s my turn to play.” Dean had to shut his eyes whens he began to rub and pet his thoughs. The woman was being wonderfully gentle with him now and that made it all the worse when his cock began reacting again. Dean was sure he couldn’t take anymore. In all that contemplation of his own limits he wasn’t expecting what came next. A spit slick finger circled his asshole and spread his cheeks.
“Whoa! What the fuck are you doing?” Dean jumped and tried to wiggle away but Sam was having none of it. She shoved his hips down against the bed and gripped him.
“Shhh.” she purred softly, small fingers drawing little circles on Dean’s leg. “You said I could do whatever I wanted. Now just relax. I promise you’ll like it.” Dean looked like he didn’t believe her. “What are you chicken?” Samantha asked, inching her fingers back up toward Dean’s ass.
“No.” Dean pouted expression hardening. He let his legs fall back open with a huff. Sure he was still nervous, but at least it was a start. Dean bucked but didn’t pull away when the woman leaned down and lapped at his hole. She spent a while licking him open and working in a finger. By the time Sam was finger deep in Dean, his brother was panting hard and clutching his thighs.
“You ok?” Sam asked, voice more gentle than teasing for the first time that night.
“Yeah.” Dean grunted, hesitantly humping down on Sam’s finger. “Peachy” He opened one eye and shot Sam his best smirk. “When are we getting to the good part?” He asked. Sam grinned and crooked his finger, drawing a gasp from Dean before pulling the digit out.
“Be right back,” He whispered, stealing a kiss and wandering to his duffle. Dean watched Sam’s switching hips, feeling himself twitch again. He was sore and exhausted, but good for at least one last round. He figured that was good because this woman just wasn’t letting up. He’d known he’d been kinky, but he was nothing compared to her. Dean watched the sway of her hips as she leaned down to pick up a small clear tube. She didn’t stop there. All her rummaging around was beginning to make him nervous again.
To be honest a lot of stuff in this situation had made him nervous but that was part of the reason he was so excited. He figured it was ok too. Samantha, Sam, hadn’t been lying. She was taking good care of him. He’d been seeing stars for the better part of an hour. Dean thought he’d reached his limit though when he looked up and saw her coming back with a tube of lube and some strange contraption in her hand.
“You sure about this?” He asked, fighting the urge to cover himself. Instead he rolled over onto his back and made room for her. He was not a chicken.
“You liked the finger right?” She asked, tracing his hole again. He nodded. “Then just let it happen. Promise it won’t hurt too much. Besides, you seem like the kind of guy who likes a little pain with his pleasure.” She shot him a grin and Dean had no choice but to watch as she slicked up two fingers and started working them in. It wasn’t long before his eyes were falling shut and he was rocking back onto them. “See,” Sam whispered. “Knew you’d like it.” When she added a third, Dean let out a little hiss and gnashed his teeth, reaching back to clutch his pillow.
“Mother fuck.” He grunted and shoved his ass back down on her fingers. ‘If you’re going to fuck me with that thing please just do it.”
“Ask nicely.” Sam commanded.
With a deep, put upon sigh Dean begged. “Please fuck me mistress. I want to feel you inside me.” He couldn’t help but laugh a little, but it was cut off when Sam’s finger’s grazed his prostate. A sharp moan ripped its way from between his lips before her fingers were sliding out of him again.
“On your knees.” Sam demanded. He was too far gone to do much more waiting. His cunt was soaked. His thighs were wet and rubbing together and it took a moment for him to get the back half of the toy inside of him. It was almost too slippery to stay, but once he finally got it situated he flexed and groaned. He’d be able to feel every single thrust into Dean’s tight ass, even if couldn’t feel the tightness around himself. This thing was definitely a good buy and he was totally taking it back to Jessica.
Creeping up behind Dean, Sam peppered a few smacks on the back of Dean’s thighs and ass. To his pleasure Dean let out a groan and presented himself farther. “Such pretty skin,” Sam commented, letting his hand smack down again. “All hot and freckly. I love how pink it gets. Wish I could keep you.” He rocked his hips down against Dean’s. Reaching between them he smeared some lube across the front end of the toy and started working the tip up and over Dean’s crack.
“Wish you could keep me too if this is how good I’m going to have it.” Dean joked, but Sam could hear the mix of lust and uneasiness in his voice. Planting a kiss on Dean’s neck Sam gently began to rock himself in, pausing every now and then for Dean to adjust to the feeling. He pulled out and slicked up some more before seating himself fully inside the man.
“Fuck.” Dean panted, fingers tightening around the headboard. “That feels…”
“Good, right?” Sam finished the sentence and Dean nodded, spreading his legs further and breathing out. It was way better than he’d ever imagined. Yeah, Ok, Dean had imagined it, even if he was in denial about it.
“Fucking fantastic.” Dean answered. Testing it out, He lifted himself up and then sunk back down. His eyes squeezed shut again when Sam finally got the message and began thrusting up into him. “Shit.” He sighed, head falling down between his shoulder blades.
“Yeah,” Sam groaned, feeling the toy shift inside of him. It was weird to have a pussy, but this made everything better. He loved the feel of the bulb shifting inside of him. The gentle sway of the ridges against his clit wasn’t bad either. Slowly his thrusts got harder, faster, deeper, until Dean was moaning like a fucking whore and bouncing on his cock.
“Fuck yeah you little bitch. You like that don’t you?” Sam moaned. “You like taking my fake cock. Probably wish it was the real thing.” Sam breathed out, peppering bites down Dean’s back. “Probably wish I could come in you and mark you up, huh? Or maybe you want me to come with my toy pushing inside both of us. Maybe you’ll flip me over and just come all over and in me huh? Just waiting for your chance?”
“Fuck! Shit!” Those seemed to be the only words capable of coming out of Dean’s mouth. The rest were strangled gasps and grunts. With his head thrown back Dean’s neck was bared to Sam’s bites and licks. Sam’s pretty, filed nails were pinching his nipples and scratching his sides, moving oh so close to his weeping dick.
“So fucking close, aren’t you pretty girl? You’re going to come on my cock, just from me fucking you. I’m not even going to have to touch you am I?” Dean shook his head violently, thighs shaking as he moved with Samantha, dropping up and down on her cock.
‘Please Sam. Sammy, say I can come.” Dean bit off his high whine, dick twitching dangerously even as he thought about what had just come out of his mouth. This was not Sammy and he almost couldn’t believe he’d called her that, but then her hips were snapping and it didn’t matter. That toy was drawing squeaks and sounds from him, punching the air out of his lungs in short gasps. Her hand closed around him then.
“Yeah. Fuck. Good boy. Come for me. Call me that again. Come on Dean, Come for me.”
“Shit. Sam. Sam. Sammy, Fuck! Sammy.” Dean shouted, hips pumping and shooting out the last of his come until he was shuddering against her, coming dry and mewling as she gave a few more thrusts and felt her own orgasm wash over her. Sam clenched down around the toy and moaned. With her teeth still caught in Dean’s skin, she slid off the strap-on. It was still inside her partner and so she reached down and worked it out of him, smiling as he rolled over and collapsed onto the bed. He was beet red and covered in sweat, panting, shaking, and laughing in gentle rumbles. Sam tossed the toy to the foot of the bed and curled up around him, small arm sliding over the expanse of his stomach.
“Was it good for you?” She laughed, propping her chin on his chest. He just huffed and nodded. “Best sex I’ve ever had,” he admitted. “and I didn’t even get to get inside you.” Dean faked a pout and Sam replied with a smile.
“Maybe in a few hours…when we’ve had some rest.” Dean looked at her and shook his head.
“God I wish I could keep you.” Dean smirked and kissed her, arms wrapping around the girl as they settled into each other for a nap. Sam just smiled; Dean of course already had him. He just had to wake up and come get him.
***
The next morning, when Dean woke up, Sam was already gone. She’d left a note and some breakfast but that was it. Dean laughed about it later. He’d been played just as much as he played the girls he normally went after. And you know what? He fucking liked it. Dean finished the breakfast that was left for him, all the while wondering if she’d taken his car to go and get it. After grabbing a shower, he met back up with his father. They had a new case one state over and it was time to get going. He just hoped one day he’d get to have all that again. Until then, the sting in his ass was enough to remind him of an awesome night.
- 1
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Bittersweet