Highway to Hell: One Shots: "Why Don't You and I"
Highway to Hell : One Shots
Why Don't You and I
Chapter Wordcount: 2075
Rating: NC17
A/N: Title from "Why Don't You and I" by Santana and Alex Band
Monte loosened her jaw, letting Dean thrust in with short shallow strokes, moaning around him as he circled his tongue around her.
Her leg hitched and she draped it over his shoulder, shifting her weight so she could bring her hand up to cup his balls.
Dean slipped a finger inside her next to his tongue and focused on her instead of the roll of his own hips, nipping at the inside of her thigh when she swirled her tongue around his head.
“Baby,” he groaned, sighing when she moaned around him.
He braced himself enough so he could look up at where she was sucking him and his fingers dug into her thigh, head resting on it like a pillow and tilted his hips into her mouth.
She sucked hard, tongue flicking against the head and he growled as his release shot through him, watching the underside of her throat roll as she swallowed.
She smiled lazily at him, dragging her thumb over her bottom lip to catch a bead of cum that had slipped and he closed his eyes and groaned again, shifting back around on the bed so he could focus on her.
She sighed, collapsing onto her back and draped one leg over his shoulder as he crawled between her legs.
“You okay babe?” he grinned, licking his lips as he pulled himself back up beside her.
“Shut up,” she laughed, smacking his chest half-heartedly as he bent to kiss her, hand sliding over her stomach.
“You know you love me,” he grinned, rolling onto his back and letting her curl up against him as she came back down.
“Uh huh,” she grinned.
He chuckled and tugged on her shoulder. “Love you too babe.”
“How much?” she asked a couple minutes later, her breathing finally back to normal.
“What?” he asked, cracking his eyes open from where he was dozing contentedly beside her.
“How much do you love me?”
He just sort of stared at her for a minute.
“A lot…” he said slowly, brow drawn down in confusion.
“You trust me?”
“Yea…Monte what…”
“How much?” she asked, sliding her leg over his waist so she could sit on his abs.
“With my life,” he said softly, hands sliding up her thighs. “Why?”
“Can I try something?” she said softly, but he could see hesitation in her eyes.
“Like what?”
“Something,” she mumbled, scooting herself down in between his thighs so she could stroke his cock back to hardness.
He shifted, widening his legs for her.
“Yea,” he grinned, putting his hands behind his head. “If it involves junior there, hell yea.”
“Promise me something?”
“What?”
“Don’t ever call it that again,” she grinned.
He laughed, “Alright fine, what ya got in mind?”
She slid her hand down his shaft, cupped his balls for a second before trailing her fingers underneath them.
His hips jerked from the unfamiliar touch and his eyes locked on hers.
She just stared at him in silence and he swallowed hard.
“Monte…”
“Think about it before you say no.”
He swallowed again and relaxed back down onto the bed, sighing when she went back to stroking him gently.
“You really want to?”
He’d had some girls in the past try to shove a finger in him while they were going down on him but most of the time he could just manhandle them onto the bed and fuck them senseless until they couldn’t remember that they had even tried it.
“I want to try,” she finally whispered.
He reached down and she let him lace his fingers with hers and sat in silence while he thought about it.
“Not gonna promise I’ll like it,” he finally rumbled.
“I know. But some guys do.”
He squeezed her hand in his and brought it back up to put behind his head.
“Go ahead baby.”
“Dean…”
“I trust you. You know that, and if there’s anyone that I’m ever gonna try this with it’s you. So…yea,” he swallowed. “We can try.”
She crawled back up to kiss him, sighing against his lips when he slid his fingers into her hair.
“You wanna stop and you tell me, okay?” she whispered, lips grazing his as she stared at him.
“Promise baby,” he rumbled.
He put his hand back behind his head and watched her as she grabbed the pillow next to him.
He lifted his hips without a word and let her stuff it underneath him and then closed his eyes and tilted his head back.
“Dean?”
“I’m okay,” he grinned, cracking an eye open at her. “It’s okay.”
She nodded and ran her tongue over her bottom lip before taking his cock in her hand again.
He sighed, letting himself relax under her hands as she stroked him. He did trust her and he meant what he said, Monte was the only person he’d ever allow try this. Ever allow himself to relax enough around to try this.
Her hands were slow and sure, pleasure rolling through him in a slow burn and he groaned, shifting his legs for her when she moved to lay on her stomach, her elbows digging into the mattress as her hands kept moving over his skin.
He wasn’t really expecting the hot wet heat of her mouth to close around his head and he groaned again low in his throat and pushed up into it.
She smiled awkwardly around him, looking up at him for a minute before sliding down, rolling the heavy weight of his balls in her free hand and he went boneless, just laid back and let her do whatever she wanted.
He felt her shift and cracked his eyes open to see her stretch over to the end table and grab the lube they kept there. He couldn’t help the reflexive swallow of his throat but he offered her a small smile when her eyes snapped to his.
“I’m good,” he rumbled, deep in his chest as he let his own hand trail down to circle his shaft and stroke slowly, the soft skin still slick with her spit.
Her fingers slipped beside his for a minute, slicking up his shaft and hand with the lube she had squirted on her fingers before laying back down on her stomach, lube-cool fingers dragging down over his balls.
He inhaled sharply at the sudden temperature change and she immediately pulled back.
He smirked. He was half amused at how jumpy she was, but the other half was left with this warm, hazy around the edges loved feeling, knowing that the second he even started to voice the word ‘no’ she would stop.
“It’s okay baby,” he smiled, taking her small wrist in his hand and bringing it back to cup the velvet skin between his legs.
She laughed nervously, dropping her head and he smiled at the red the burned up her cheeks.
“It’s okay baby,” he said again. “I’ll let you know if I need to slow down or stop, okay? Otherwise just…do what you want to sweetheart.”
She smirked, cheeks still burned pinked and nodded at him, fingers slipping into the crease where his balls connected to his body and he winked at her, leaving his hand around his dick and leaned his head back again.
The contrast between the cool lube and the heat of her mouth had him jerking when she bent to run her tongue over the soft skin.
Her tongue was hot and wet when she trailed it over his fingers where they were wrapped around the base of his shaft and it distracted him enough that he didn’t startle when the tip of her finger brushed against the tight ring of muscle.
His hips did jerk when the tentative graze of her finger was replaced with the heat of the tip of her tongue.
“Jesus,” he hissed, hips stuttering and he inhaled sharply when she paused.
Her free hand was resting on his hip and he slid his own hand over top of it and squeezed, silently letting her know he was okay.
He felt her shaky breath against his skin before she took another slow lick and he couldn’t help but groan deep in his throat, handing tightening around hers.
Encouraged by his reactions she swirled her tongue, sealing her lips around the ring to suck a quick kiss before teasing the entrance with the tip of her tongue.
“Son of a bitch,” he whispered, hips twitching up into the touch.
It was completely weird but damn if he didn’t like it and the fact that it was something new had a spike of heat shooting up his spine.
He was biting back a whimper, ‘cause like hell he was going to make a sound like that, when she pulled back and went back to sweeping her finger over the wet skin.
Her hand squeezed in his and she pushed, letting the tip of her finger breach his body.
He immediately clamped down, muscles fighting against the strange sensation.
“Sshh,” she whispered, “Let me in Dean.”
He inhaled sharp, trying to will himself to relax and gasped when he felt her finger slide deeper into him.
“Shit…stop, hold on…”
“No, trust me Dean, it’s better if you just keep moving,” she said softly, stroking in and out a couple of times, his body loosening around her finger and he sighed, chest heaving.
“God…this what it feels like when I do this to you?”
He felt her smile against his skin before she kissed the inside of his thigh.
“You okay?”
“Yea,” he mumbled, hand stroking his shaft slowly as she worked her finger deeper into him.
He felt her nudge a second beside the first and his body clamped down again.
He squeezed her hand in silence and inhaled again. He’d fucked her in the ass more than once and if she could take his cock he could damn well take a couple fingers.
She slid the second in beside the first and worked up a smooth slow rhythm. He let himself relax into the soft pressure. It was strange, but not unpleasant really, just…different.
Before long he was shifting his hips between the circle of his fist and the slide of he fingers, his stomach tightening against the slow burn of pleasure through his muscles.
She kissed the inside of his thigh again and his knee jerked as she crooked her finger.
“Jesus, wha…what the hell…”
She rubbed whatever spot it was inside him again, soft circular movement and he jerked, torn between pulling away and shoving down harder onto her hand.
“Fuck,” he hissed. “Monte…what…”
“It’s your prostate,” she said softly, looking up at him as she still swirled her fingers inside him.
“Shit,” he breathed, letting his head thump back as he squeezed his dick tighter.
“Oh god,” he groaned, stroking faster as she leaned forward to suck on his balls, fingers still moving inside him.
Her hand squeezed on his hip and he growled deep in his throat as his release tore through him.
“Fuck, fuck…god,” he hissed, fist squeezing as he tugged on his cock, hips stuttering on her hand.
“Shit…baby, stop…I can’t…” he said in between gulps of air.
She pulled out slowly and rolled off the bed.
His chest was still heaving when she came back a moment later with a soft wash cloth.
“Fuck,” he hissed, tossing it to the side when he was finished and shifted enough so she could curl up next to him.
“You knew about that didn’t you?” he breathed.
She kissed his nipple and smiled. “Maybe.”
He laughed and tugged on her shoulder, bringing her closer to his side.
She propped her chin up on his chest and stared at him with wide eyes.
He smirked and craned his neck to kiss her, his hand running through her hair when he pulled back.
“It was good,” he rumbled.
Her cheeks burned and she looked away with a grin.
“Oh come on,” he laughed, “It was your idea. I’m just saying…I…I liked it.”
She looked back up at him, arm wrapping around his waist.
“Maybe next time we could bust out one of you, um,” he cleared his throat, “toys.”
She just laughed at him.
“Next time huh?” she grinned.
He shrugged his shoulder and smirked at her.
“Told you babe, wasn’t bad,” he grinned. “So yea…if you want to, again, sometime…I’m game.”
She smirked and pulled him into another kiss.
Previous: Wrapped Up in You | Next: Catch the Horizon
Highway to Hell Master Post
Why Don't You and I
Chapter Wordcount: 2075
Rating: NC17
A/N: Title from "Why Don't You and I" by Santana and Alex Band
Monte loosened her jaw, letting Dean thrust in with short shallow strokes, moaning around him as he circled his tongue around her.
Her leg hitched and she draped it over his shoulder, shifting her weight so she could bring her hand up to cup his balls.
Dean slipped a finger inside her next to his tongue and focused on her instead of the roll of his own hips, nipping at the inside of her thigh when she swirled her tongue around his head.
“Baby,” he groaned, sighing when she moaned around him.
He braced himself enough so he could look up at where she was sucking him and his fingers dug into her thigh, head resting on it like a pillow and tilted his hips into her mouth.
She sucked hard, tongue flicking against the head and he growled as his release shot through him, watching the underside of her throat roll as she swallowed.
She smiled lazily at him, dragging her thumb over her bottom lip to catch a bead of cum that had slipped and he closed his eyes and groaned again, shifting back around on the bed so he could focus on her.
She sighed, collapsing onto her back and draped one leg over his shoulder as he crawled between her legs.
“You okay babe?” he grinned, licking his lips as he pulled himself back up beside her.
“Shut up,” she laughed, smacking his chest half-heartedly as he bent to kiss her, hand sliding over her stomach.
“You know you love me,” he grinned, rolling onto his back and letting her curl up against him as she came back down.
“Uh huh,” she grinned.
He chuckled and tugged on her shoulder. “Love you too babe.”
“How much?” she asked a couple minutes later, her breathing finally back to normal.
“What?” he asked, cracking his eyes open from where he was dozing contentedly beside her.
“How much do you love me?”
He just sort of stared at her for a minute.
“A lot…” he said slowly, brow drawn down in confusion.
“You trust me?”
“Yea…Monte what…”
“How much?” she asked, sliding her leg over his waist so she could sit on his abs.
“With my life,” he said softly, hands sliding up her thighs. “Why?”
“Can I try something?” she said softly, but he could see hesitation in her eyes.
“Like what?”
“Something,” she mumbled, scooting herself down in between his thighs so she could stroke his cock back to hardness.
He shifted, widening his legs for her.
“Yea,” he grinned, putting his hands behind his head. “If it involves junior there, hell yea.”
“Promise me something?”
“What?”
“Don’t ever call it that again,” she grinned.
He laughed, “Alright fine, what ya got in mind?”
She slid her hand down his shaft, cupped his balls for a second before trailing her fingers underneath them.
His hips jerked from the unfamiliar touch and his eyes locked on hers.
She just stared at him in silence and he swallowed hard.
“Monte…”
“Think about it before you say no.”
He swallowed again and relaxed back down onto the bed, sighing when she went back to stroking him gently.
“You really want to?”
He’d had some girls in the past try to shove a finger in him while they were going down on him but most of the time he could just manhandle them onto the bed and fuck them senseless until they couldn’t remember that they had even tried it.
“I want to try,” she finally whispered.
He reached down and she let him lace his fingers with hers and sat in silence while he thought about it.
“Not gonna promise I’ll like it,” he finally rumbled.
“I know. But some guys do.”
He squeezed her hand in his and brought it back up to put behind his head.
“Go ahead baby.”
“Dean…”
“I trust you. You know that, and if there’s anyone that I’m ever gonna try this with it’s you. So…yea,” he swallowed. “We can try.”
She crawled back up to kiss him, sighing against his lips when he slid his fingers into her hair.
“You wanna stop and you tell me, okay?” she whispered, lips grazing his as she stared at him.
“Promise baby,” he rumbled.
He put his hand back behind his head and watched her as she grabbed the pillow next to him.
He lifted his hips without a word and let her stuff it underneath him and then closed his eyes and tilted his head back.
“Dean?”
“I’m okay,” he grinned, cracking an eye open at her. “It’s okay.”
She nodded and ran her tongue over her bottom lip before taking his cock in her hand again.
He sighed, letting himself relax under her hands as she stroked him. He did trust her and he meant what he said, Monte was the only person he’d ever allow try this. Ever allow himself to relax enough around to try this.
Her hands were slow and sure, pleasure rolling through him in a slow burn and he groaned, shifting his legs for her when she moved to lay on her stomach, her elbows digging into the mattress as her hands kept moving over his skin.
He wasn’t really expecting the hot wet heat of her mouth to close around his head and he groaned again low in his throat and pushed up into it.
She smiled awkwardly around him, looking up at him for a minute before sliding down, rolling the heavy weight of his balls in her free hand and he went boneless, just laid back and let her do whatever she wanted.
He felt her shift and cracked his eyes open to see her stretch over to the end table and grab the lube they kept there. He couldn’t help the reflexive swallow of his throat but he offered her a small smile when her eyes snapped to his.
“I’m good,” he rumbled, deep in his chest as he let his own hand trail down to circle his shaft and stroke slowly, the soft skin still slick with her spit.
Her fingers slipped beside his for a minute, slicking up his shaft and hand with the lube she had squirted on her fingers before laying back down on her stomach, lube-cool fingers dragging down over his balls.
He inhaled sharply at the sudden temperature change and she immediately pulled back.
He smirked. He was half amused at how jumpy she was, but the other half was left with this warm, hazy around the edges loved feeling, knowing that the second he even started to voice the word ‘no’ she would stop.
“It’s okay baby,” he smiled, taking her small wrist in his hand and bringing it back to cup the velvet skin between his legs.
She laughed nervously, dropping her head and he smiled at the red the burned up her cheeks.
“It’s okay baby,” he said again. “I’ll let you know if I need to slow down or stop, okay? Otherwise just…do what you want to sweetheart.”
She smirked, cheeks still burned pinked and nodded at him, fingers slipping into the crease where his balls connected to his body and he winked at her, leaving his hand around his dick and leaned his head back again.
The contrast between the cool lube and the heat of her mouth had him jerking when she bent to run her tongue over the soft skin.
Her tongue was hot and wet when she trailed it over his fingers where they were wrapped around the base of his shaft and it distracted him enough that he didn’t startle when the tip of her finger brushed against the tight ring of muscle.
His hips did jerk when the tentative graze of her finger was replaced with the heat of the tip of her tongue.
“Jesus,” he hissed, hips stuttering and he inhaled sharply when she paused.
Her free hand was resting on his hip and he slid his own hand over top of it and squeezed, silently letting her know he was okay.
He felt her shaky breath against his skin before she took another slow lick and he couldn’t help but groan deep in his throat, handing tightening around hers.
Encouraged by his reactions she swirled her tongue, sealing her lips around the ring to suck a quick kiss before teasing the entrance with the tip of her tongue.
“Son of a bitch,” he whispered, hips twitching up into the touch.
It was completely weird but damn if he didn’t like it and the fact that it was something new had a spike of heat shooting up his spine.
He was biting back a whimper, ‘cause like hell he was going to make a sound like that, when she pulled back and went back to sweeping her finger over the wet skin.
Her hand squeezed in his and she pushed, letting the tip of her finger breach his body.
He immediately clamped down, muscles fighting against the strange sensation.
“Sshh,” she whispered, “Let me in Dean.”
He inhaled sharp, trying to will himself to relax and gasped when he felt her finger slide deeper into him.
“Shit…stop, hold on…”
“No, trust me Dean, it’s better if you just keep moving,” she said softly, stroking in and out a couple of times, his body loosening around her finger and he sighed, chest heaving.
“God…this what it feels like when I do this to you?”
He felt her smile against his skin before she kissed the inside of his thigh.
“You okay?”
“Yea,” he mumbled, hand stroking his shaft slowly as she worked her finger deeper into him.
He felt her nudge a second beside the first and his body clamped down again.
He squeezed her hand in silence and inhaled again. He’d fucked her in the ass more than once and if she could take his cock he could damn well take a couple fingers.
She slid the second in beside the first and worked up a smooth slow rhythm. He let himself relax into the soft pressure. It was strange, but not unpleasant really, just…different.
Before long he was shifting his hips between the circle of his fist and the slide of he fingers, his stomach tightening against the slow burn of pleasure through his muscles.
She kissed the inside of his thigh again and his knee jerked as she crooked her finger.
“Jesus, wha…what the hell…”
She rubbed whatever spot it was inside him again, soft circular movement and he jerked, torn between pulling away and shoving down harder onto her hand.
“Fuck,” he hissed. “Monte…what…”
“It’s your prostate,” she said softly, looking up at him as she still swirled her fingers inside him.
“Shit,” he breathed, letting his head thump back as he squeezed his dick tighter.
“Oh god,” he groaned, stroking faster as she leaned forward to suck on his balls, fingers still moving inside him.
Her hand squeezed on his hip and he growled deep in his throat as his release tore through him.
“Fuck, fuck…god,” he hissed, fist squeezing as he tugged on his cock, hips stuttering on her hand.
“Shit…baby, stop…I can’t…” he said in between gulps of air.
She pulled out slowly and rolled off the bed.
His chest was still heaving when she came back a moment later with a soft wash cloth.
“Fuck,” he hissed, tossing it to the side when he was finished and shifted enough so she could curl up next to him.
“You knew about that didn’t you?” he breathed.
She kissed his nipple and smiled. “Maybe.”
He laughed and tugged on her shoulder, bringing her closer to his side.
She propped her chin up on his chest and stared at him with wide eyes.
He smirked and craned his neck to kiss her, his hand running through her hair when he pulled back.
“It was good,” he rumbled.
Her cheeks burned and she looked away with a grin.
“Oh come on,” he laughed, “It was your idea. I’m just saying…I…I liked it.”
She looked back up at him, arm wrapping around his waist.
“Maybe next time we could bust out one of you, um,” he cleared his throat, “toys.”
She just laughed at him.
“Next time huh?” she grinned.
He shrugged his shoulder and smirked at her.
“Told you babe, wasn’t bad,” he grinned. “So yea…if you want to, again, sometime…I’m game.”
She smirked and pulled him into another kiss.
Previous: Wrapped Up in You | Next: Catch the Horizon
Highway to Hell Master Post