This was requested by 27. There's a bit of a background, and if you want to skip ahead I'll put a *** where the good stuff starts
I met him in a bar, drowning his sorrows in cheap beer. The man wasn't drunk, but the bartender had cleared enough bottles away for you to wonder. It was probably his size...he towered over everyone, even sitting down. In the button up flannel he wore, he was intimidating as hell.
But his face...oh man. He had long brown hair - how could it be so perfect? - that framed a sculpted jaw. He had small side burns, just enough to be charmingly handsome in a rough-and-tumble way. There was a facial structure like a model on steroids and deep, deep brown eyes that were soft and kind but had seen too much. I swooned when I saw him.
Approaching the bar I sat next to him, confident even in my young age. I introduced myself simply...got him talking. His voice was low and strong and I wanted to hear it say my name over and over again from the first time he opened his mouth. We talked about his brother and how they had just lost an uncle or something. Then he asked about me. I told him the usual...drifting through town, hanging at the bar, just looking for some fun.
At this the man's eyes had flicked up and down my body, and I noticed his jaw work slightly.
"Do you want to..." I urged him on with my eyes, but his phone rang before he could ask me to spend the night with him. He spoke quickly and gruffly, then excused himself. Funny that things would end up working out between Sam Winchester and I.
I met the second one later, in the same bar. It was a day after Sam, and he looked promising. Nursing a scotch, he had on multiple layers of clothing, an old leather coat covering a flannel and a grey tee shirt. His face was narrow with a firm jaw and a mouth set into a pursed line. His hair was light brown, cut short and modern. The man's eyes were a sparkling blue that was too deep to tell anything other than he had a bad attitude and a good sense of humor. I drooled as he winked at the hot bartender. I made my move. He didn't have much to say...we talked about music and family. I was complimented a lot. In the end, Dean offered to take me home. I sat in his car, a sexy Impala, biting my lip and trying not to attack the hot piece of ass next to me. Instead of taking me to a house or an apartment we arrived at a motel on the outside of town. I wasn't complaining. He parked the car in the empty lot and we strode to room number 7.
"Home sweet home. Ain't much, but good when you're on the road." Dean said as he unlocked the door.
We stepped inside to find a room with two beds that was obviously occupied by boys. A familiar flannel shirt was draped over one of the chairs in the corner, but I paid it no mind as Dean whispered in my ear.
"Come on baby girl let's have some fun..."
He laid me on the bed, softly at first. Then he shoved me against the headboard, pressing his lips harshly to mine. There was a desperate heat between us, as if he was starving for me. Who was I to deny him? Dean bit my bottom lip, begging for entrance so I let his tongue roam around my mouth. I grew wetter and wrapped my legs around his waist. His hands found my thigh, climbing higher and higher and I placed my hands on his neck and chest to eg him on...then a key turned in the lock to the motel room.
I tensed up, embarrassed at being caught 'in action'. Dean just rolled his eyes and planted a kiss on my lips.
"Sorry baby girl. Hold on." He got up and went to the door.
"Sammy..." He hissed. I tried not to listen to the conversation. The person on the other side of the door said something in a low voice...a low voice that I recognized. I stiffened, assuring myself it was just my imagination. Then none other than Sam Winchester pushed Dean out of the way, letting himself in.
"Amy?!" Sam said in shock when he saw me on the bed.
"Sam?" I threw right back at him. What was he doing here?
"Sammy? You know her?" Dean interjected. I flushed as I realized what had happened: the boys were brothers.
"I was...we were going to...we were talking in the bar when you called last night. What about you?" Sam said, jaw locked in frustration.
"I met her tonight in the bar you told me about. Great minds think alike, eh Sammy?" Dean said, looking just the tiniest bit defensive.
"I found her first Dean." Sam spit out. I scoffed at the word 'found'.
"Well she got away. And now I have her. So why don't you take a walk or something and I'll call you when we're done?" I blushed at Dean's bluntness.
The boys continued to argue...over me? I couldn't believe it. It was all slightly arousing. I watched Sam and Dean - the Winchesters - bicker, Dean clenching his fists and Sam waving his hands wildly. My hands crawled into my tight jeans, finding damp underwear and desperation. I fingered myself, getting off on the tension between both hot men.
When I let out a low moan, the Winchesters stopped talking. I looked up, bringing my hands to my sides and blushing even harder. Dean eyed the spot where my fingers had just left and bit his lip. Sam and his brother shared a look.
"Aw, Sammy look what we've done to poor Amy here," Dean purred, eyes scanning me up and down.
"Yeah Dean. What will we do?" Sam answered, hands in his pockets.
"M-maybe I should just go-" I stuttered.
"Now Amy, that's not necessary. We could share you know," Sam said, smirking at Dean.
"Hmmm...what do you think baby girl? Me and Sammy?"*** Dean walked to the bed, not waiting for an answer, but Sam beat him there. I nodded to him as he took me into his arms and kissed me passionately. My fingers found his hair, and I entwined them as we were pressed closer together. Sam's big hands went to my torso and held me tight. I felt a bulge as the younger brother pulled me on to his lap. One couldn't help but wonder if Sam's dick was as big as the rest of him...mmm. I shifted my butt creating friction and Sam threw his head back, moaning.
I went to kiss Sam again when Dean jerked me backwards, capturing me against his chest. I let out a squeak of surprise and he chuckled. His breath from behind was soothing and he ran his fingers through my hair lovingly. Dean's mouth found my neck and left kisses up and down, before he started biting and sucking. My head rolled to the side as his hands held me close against him. His sculpted chest was hard against my back even through our clothing and I relaxed against it. I shuddered when Dean's lips tickled my temple and sucked on my ear lobe.
Sam sat across from the pair, a bit of jealousy flaring up in his chest. More importantly he was now hard and he knew he and Dean should work together on this one. So Sammy reached forward as Amy's eyes were closed and nodded to Dean while he unbuttoned the girl's jeans. Without changing position she unfolded her legs so he could slide them off. How cute.
I felt my jeans being tugged down and happily let them be pulled away from my heated body. Dean's hands rubbed up and down my thighs and I let my head fall against his chest as he and Sam shared a look.
"Baby girl Sam and I both want you tonight. And neither of us is willing to wait. So I'm going to fuck that pretty little pussy of yours, and Sammy is gonna fuck you from behind. Okay baby girl?" I nodded, excited at the new concept.
Dean pushed me forward, so I sat freely in between two hot brothers, each facing me. The older brother guided my arms above my head as Sam - now shirtless - reached forward and pulled my shirt away, blowing air on my exposed stomach then taking me from Dean's arms.
I hooked my arms behind Sam's head and kissed him fiercely until he pulled away. I pouted up at him and he laughed, gorgeous hair waving.
"Mmm baby girl," he said, adopting Dean's nickname for me and leaving me with chills. I heard Dean's shirt being thrown to the floor behind us. "Has anyone ever fucked your ass before?" I shook my head no and he smiled comfortingly.
"Alright baby girl, I'm gonna prep you. Hands and knees." I complied, climbing into position facing a bare-chested Dean. I bit my lip as Sam grasped my hips in his large hands and slid my underwear down. I shuttered at the cold air and looked up. I blushed when I heard Sam throw my panties through the air to Dean, who deftly caught them. He bunched the fabric up and pretended to smell it, making me giggle.
Dean threw the underwear away and bent down to kiss me in my position. He had taken his jeans off and I took a sharp breath at the sight of the tent in his boxers. Only a funny looking brassy pendant hung on a leather cord and boxers were keeping me from him. I grasped his neck and wrapped my arms around him as he scooted closer so he was holding me up. Then Dean kissed me, tongues twisting together. He brought his hands to my sides and braced me further so our eyes could meet.
"Ready baby girl?" He said. I nodded once more and he lifted his chin to Sam who was still holding my hips.
"Breathe," Sam said as he placed a kiss on my butt. "You have such a cute ass, baby girl but this is going to hurt okay? Just breathe." Sam sucked on a finger and spread her cheeks a part, sliding it into her virgin asshole.
"Aaahhh...Sam..." I bucked at the pain when Sam slid his finger into me, stretching me out. Dean kissed me and whispered reassurances into my ear. He kissed my head and then my sweet spot, sucking it and making me moan as Sam began to move his finger in and out of me. My face scrunched up, but I found the pleasure after a few more thrusts.
"Sammy?" I pleaded when one finger was no longer enough. He chuckled when I used his pet name and added another finger.
"Mmmm..." I groaned against Dean's shoulder, biting down as Sam began to scissor me open, curling his finger.
"So good baby girl, you're being so good." Dean said, tilting his neck so I could suck harder.
"One more okay? You gotta be ready for me baby girl." Sam promised adding his third finger before I could protest. I cried out when he pulled his fingers in and out of me at a fast pace. This time it took longer for the pain to subside, but when the pleasure took hold I sighed into Dean's hair happily.
When he thought I was ready, Sam pulled all three fingers out of me. I whimpered at the empty feeling and Dean pulled me forward as Sammy shed his pants.
"We're gonna fuck you baby girl and then you're gonna suck Sammy and I off okay? And if you're good, we'll eat that pretty little pussy of yours out," He explained and I nodded eagerly. "Alright. Sammy first."
I lay down on my side and Sam brushed my hair with his fingers from behind. I bit my lip and got damper when Dean threw a condom to him behind me. Shedding his own boxers Dean rolled one on and held on to me.
I felt Sam grab my waist again, with Dean holding my stomach and the two lowered me on to Sam's erect dick.
"Ooooh, Saaaam!" I said loudly, not having been prepared enough for his large cock that now filled me up.
"Baby girl so tight you're doing a great job." Sam said, kissing the back of my head and smoothing my hair as I squeezed my eyes shut. I felt fingers brush my jaw and I opened my eyes to see Dean kissing my head.
"I'm gonna put it in you, and then you tell us when we can move okay?" Dean said, spreading my legs and kissing my inner thighs. Sam shifted underneath me and I whimpered, until Dean slid into my wet heat. I felt so full...of both my boys. It felt so good.
"Move," I commanded.
"Which one baby girl?" Sam asked, kissing my neck some more.
"Both of you!" I said through clenched teeth.
The boys went for a rhythm, Dean starting with a slow thrust into me. I shuddered. Then Sam went, gingerly pulling out and sliding back into me. A moan of pain and pleasure bubbled out of my lips when they did it again, and again. Dean rubbed his hands up and down the curves of my body, leaving trails of icy sensitivity and fiery passion. Sam reached his hands around to my front as he thrust a little harder into me, fingering my clit while Dean picked up the pace.
"Baby girl you feel so good taking my cock like this," Sam whispered in my ear, his voice leaving me with even less breath than I had to begin with. "You're so tight, my little virgin baby girl."
Dean tensed, watching Sam whisper in Amy's ear like that. He couldn't help but feel possessive of her, and since when was little Sammy one for dirty talk? The little flame of jealousy surprised the older Winchester, and Dean used it to channel the lust.
Dean slammed into me quicker, causing ripples of pleasure to wash through my core.
"Feel good baby girl? Like taking both of us? You look so pretty, my little cock slut." I gasped at his words, thrusting on to him in response.
Sam's fingers distracted me as well, flicking and rubbing my clit bringing me nearer and nearer to the edge. All the pain had gone now, and I just wanted more of Sammy inside of me. He was still taking it slow, taking me slow, watching out for my tight little virgin baby girl ass. I loved it. More.
"Sam...Sammy faster." I gasped, rolling my hips harder onto the boy. I felt the muscles in his lower stomach tense and his cock twitch at my request, but he held back.
"Are you sure? I don't want to hurt you..." He replied, eliciting an eye roll from a very happy Dean.
"Of course she's sure, idiot. Right baby girl?" Dean said. I nodded, eyes closing.
"Jerk." Sam muttered and slammed into my ass, filling me up all the way. My eyelids fluttered and my nails found Dean's back, curling and scratching as I saw stars. Dean winced and said to Sam over my shoulder:
"Bitch."
"Dean...Dean keep going..." I mustered out, hoping he would continue to escalate the pace. He stiffened and I realized he hadn't been getting the attention he deserved for the night. Since his face was so close to mine I raised up and enclosed his lips in my own, getting a growl from him. He slammed into me harder, twisting so he hit my clit.
"Aaaahh..." I groaned at the feeling. Not forgetting my Sammy, I bounced a bit, relishing the sinful pleasure it gave me. He brought his hands around to my breasts in response and cupped them, then unclasped my bra. Dean took it from Sam and slid it off me, throwing it away and sucking at my breasts. Sam wasn't having it and slapped his brother's face away lightly, replacing mouth with hands and pulling and plucking at my nipples. I leaned back into him and rode the boy harder.
"Baby girl you've been such a good girl..." Sam let out, breathless.
"Such a good slut for us baby girl," Dean continued, still pounding into me.
"Taking both our cocks like this baby girl so good." Sammy went on.
"Wanna cum for us baby girl? I know you're close."
I nodded, then let out one more request:
"Harder."
Sam and Dean rammed into me, forgetting all patterns and rhythm. I jumped in between them, twisting and writhing until Dean had to hold my waist down onto Sam, and Sam crossed his arms over me. I felt the warm sensation bubble up and over the top at last, and I spilled over Dean with a shout.
"DEAN oh my god SAMMYYY," I yelled. "Sam...Dean..." Their names tumbled from my lips.
"That's it baby girl, that's it." Sam said.
"So good for us baby girl, here we come," Dean spoke. Sammy came first, pooling into the condom and coming to a stop. Dean thrust lazily a few more times, following until he was still too. Sam bit my neck, up and down sucking praise into the soft skin and gripping my waist possessively. Dean took my torso in his grip and attacked my mouth, biting and sucking and muttering thanks against it. When then had both calmed down, Dean slid out, then gently helped Sammy push me off him. I felt so empty now.
"Not done yet baby girl..."
I lay on the bed, looking up at both brothers with wide eyes, chest heaving.
"You want me to suck you off?" I said, a smile playing at my lips. I barely noticed the throbbing in my ass and raised my eyebrows at the boys' worried expressions.
"Not...not if you don't want to..." Sam stuttered. "If you're too tired-"
I laughed at his loss of confidence now that he was standing up. He was cute, blushing and all. I knew he was dirty though, just had to loosen him up a bit.
"No Sammy. Just wondering who wanted to go first?" A hungry expression returned to Sam at that point, smiling now that he knew I was alright. Dean interjected before his little brother could even open his mouth.
"Come her baby girl. Show me that pretty little mouth of yours," He said, shedding the used protection and tossing it away. "Try not to get too horny Sammy."
Dean opened his arms as I stood up off the bed. I kissed him, deeply, and his strong arms melded us together. Then I seperated our lips, smirking, and I sank to my knees slowly.
Bringing my hands up, I grabbed the base of Dean's shaft, twisting my hands a bit. Then I licked his tip, sucking slowly. Playfully, I nipped it, and Dean jumped. He exhaled and his cock twitched. I pursed my lips and blew a kiss to Dean watching me, then took him into my mouth, slowly. I sucked and hollowed my cheeks, going deeper onto him. Then I took my mouth away.
"Baby...baby girl keep going you're doing fine." Dean said. Ha. I knew.
I watched precum leak out of his dick, and then observed as it grew painfully hard. Dean tensed, hands in fists at his sides. I smiled sweetly, pretending to go down slowly...and then I swallowed his whole dick up, quickly.
"AH baby girl I swear..." Dean gushed as I bobbed my head. I relaxed the muscles in my throat, taking him deeper and watching in pleasure as he thrusted against me, fucking my mouth. Dean grabbed my hair, pulling and plucking then pushing my face closer to his thighs. I massaged and squeezed his balls, giggling around him as the muscles in his lower abdomen twitched. Then I wrapped my hands around to his butt, squeezing, and slurped my mouth off of Dean. I blew lightly, and Dean came, all down my front. I laughed.
"Ooohhhh..." Dean moaned. He didn't even have the strength to say my name. Shame, I might have blown him again. I felt sticky from the older Winchester's cum, and I felt a hand pull me up. Dean, out of his haze, began to lick me down, biting here and there until I was clean. Then he kissed me lightly on the lips and turned me harshly around.
"Good job. Go get Sammy baby girl." He instructed, pushing me forward and slapping my ass. Dean sat back down on the bed, heart beat slowing to it's normal rate again.
I turned to see the younger brother a mess on the second bed. His eyes were squeezed shut and he was jerking off rapidly, looking for a release. The sight had me weak at the knees, poor baby. I went to help him out.
I approached him quietly, watching for a moment as he tried to find pleasure with himself. Then I grasped his big hands, guiding them to his sides. I took his legs next - they were tight at his thighs so I pulled them down and layed his muscular chest down on the bed. I decided not to tease this one - he had been denied enough tonight. I simply kissed him on the lips and took his length in my hands. Picking up where he left off, I flicked my wrist a few times, pumping Sam, giving his hard on some relief. Smearing his precum over, I bent down, bringing my lips to his shaft.
I licked a stripe up and down him, grazing my teeth before wrapping my lips around Sam. His chest raised up but I pushed it back down with one splayed hand, dragging a nail down his contoured abs to his v-line. I hollowed my cheeks, mimicking my treatment of Dean before I decided to add something extra for patient little Sammy.
Snaking my hands underneath Sam's legs, I pushed on his butt to make him rise into the air slightly. The movement had me cringe as his significant size filled my mouth further, but I kept going. Keeping his pelvis in the hair with one hand, I used the other to find the boy's hole.
Sam sucked in a breath.
"What are you-"
"Payback Sammy." I explained, mumbling around his cock. I slid my mouth away, planting a kiss on Sam's tip and focused on my fingers. I found resistance, but pushed one in anyway. Quickly I added a second, ignoring protests. I curled and scissored Sammy's virgin hole and laughed inwardly at the irony. Somewhere from the other side of the room I heard a voice say "breathe Sammy" with a snort, but I ignored it. I thrusted my fingers harder and Sam came with a scream, on me again, but I didn't mind.
"Baby girl...what you do to me...I won't walk for a week." Sam joked, pulling me out from under him and sitting me on his lap. He kissed my hair, and then my mouth, sweet and kind after all the tension.
"Now we're even," I said playfully. I heard Dean come up behind me, brushing my hair back and kissing my neck as Sam placed a hand on my stomach. They picked me up, Sam carrying my arms and Dean with my feet. I laughed out loud as they swung me through the air and on to the bed.
"You're turn baby girl. Cum for us one more time." Dean said, crawling over me. Sam came next, spreading my legs.
Sam lowered his face to my wet heat, placing one tender kiss. Then Dean, nipping at my inner thighs. Sam again, licking up my slit...and Dean after, tongue poking at my clit. They switched out, teasing and biting and sucking until they were taking shifts plunging their tongues into me, poking and prodding at my nipples all the while. I came slowly and sweetly, and both boys stuck their fingers back in to get a taste.
Sam took me into his strong grip, scooping me to him so my head lay on his chest and my legs were draped over his arms. He shifted me up and Dean pulled down the covers of the bed, letting Sam lay me down. Dean climbed in after me, holding me softly to him so my face lay underneath that peculiar necklace of his. Sam joined us last, smoothing my hair and bringing one long leg over me, arms sliding around Dean and I.
"You're so good baby girl," Sam said, kissing the back of my head.
"Our sweet dirty baby girl," Dean agreed, pecking my forehead. They showered me with praise until I fell asleep in their arms, drifting away with the Winchesters.