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You didn’t mind too much that you were usually left at the bunker when the Winchesters went off to cases. You were a researcher first, and then a hunter. It’s not that you weren’t strong enough for the job or capable – you were one badass chick – but you preferred the research, the books. If that meant the boys were away from you some nights, well…
Skype was a wonderful to keep “in touch,” as it were, and you weren’t going to deny that it was hot as hell to watch Dean & Sam play out little fantasies for you on the screen while you pleasured yourself with the dildos they’d bought for you for this exact purpose. The toys weren’t quite the same size as the brothers – “can’t have you not missing the real thing, baby girl,” Dean had whispered the first night you’d played with them, before pulling out the long, life-like (aside from the dark purple coloring) toy and slamming himself inside you, stretching you out that last bit – but they were close.
Lately, you had even been excited to have some time to yourself because it gave you a chance to work on a surprise you’d decided to give the boys. It had started one night several weeks ago when the three of you were watching a porno Dean had picked up – it was a mmf threesome, and pretty hot even if the male leads had nothing on Sam and Dean. But then they’d both started fucking the woman at the same time and you’d felt Dean’s breathing change while he watched. The hand he’d been using to lightly tease your breast had tightened, twisting the nub. Sam had reacted, too, both men responding eagerly to the sight of the woman bouncing between the two cocks on screen.
That night had been fun, to say the least, so it was no question that it stayed in your memory. But you really remembered how they’d reacted to the double penetration. And so you set about doing a little research on the side when the boys were gone.
You’d felt just a little silly the first time you’d googled “how does dp work?”. Surely all you were going to get were links to porn – which, you figured, couldn’t hurt either, but still. You kind of wanted something a bit more educational. It wasn’t that you and the boys had never done anal, but it wasn’t a common thing. Dean usually preferred to have Sam fuck you good, get you soaked and stretched and full of his cum, and then Dean would take you. To your surprise, there were several good links about anal sex for women and first time DP. Reddit, of all places, was the most helpful and you’d devoured the information.
The first time you’d worked the longest of your toys – all the advice said to have the longest dick in the back and the widest go in the front – and then begun to work it in and out of you, you experienced what most of the websites had said. There was pressure and a feeling of fullness – not unpleasant, but not like being fucked normally. It felt a little odd, awkward. Some of that was the angle, but once you’d figured that out, it became easier. You figured out that relaxation and flexibility were the key.
Dean had laughed at you when you’d started doing yoga with Sam in the mornings, but he’d soon stopped when you showed off your new flexibility by essentially doing the splits on top of him – one knee bent back around his waist with the other leg stretched out & up over his shoulder – allowing him to fuck into you deeper than ever before. And then you’d almost done a back bend to suck Sam’s cock where he was kneeling at the foot of the bed. After that, he’d simply watched you and Sam stretch and go through your routines in the morning, occasionally jerking himself to hardness and then having the two of you come over and suck him off, telling you both how good you were for Daddy.
The yoga helped in more ways than one. You were able to bend better and fix the angle, but the breathing also helped you relax and stretch yourself open easier. It still wasn’t the same pleasure as being properly fucked, but it wasn’t uncomfortable. With this accomplished, it was time to move on to step two – orgasming with the cock in your ass.
Most of the time you’d played with the toy, your orgasm had come after. You had played with yourself while stuffed full of fake cock, but never to the point of cumming. Part of that was that the feeling just never felt quite right. You would rub your clit and lightly slap at your empty pussy, getting aroused, but that made you tighten up and bear down on the toy in your ass, which made you lose focus. Eventually, you’d pull it out and shove the second toy into your pussy & orgasm that way.
Now, though, you felt more confident. You were comfortable with the toy and the thought of what you were working yourself towards was becoming more and more desirable. Still, you were apprehensive. You knew you weren’t quite ready to stick something else inside you while the one toy was already held tight in your ass – but you were still nervous about taking the next step.
You’d worked yourself up to the point where you’d normally take the toy out and chase your release, but this time, you held the toy firmly inside you, not letting it slide out. You groaned as you squeezed it, continuing to work at your clit until the full feeling was a part of your pleasure instead of a distraction. You’d felt a little sore after the first time when it was done, but you’d also felt excited to try it again.
After that, you made sure to cum at least once a day with the toy lodged in your ass. You couldn’t cum from that alone, but you’d started finding ways to heighten your pleasure – twisting the toy inside you when you flicked your clit added an unexpected burst of sensation. When you started using your vibrating wand on your clit with the dildo in you, your orgasm was unexpectedly strong.
And then came the week where you knew you were ready for more – it was time for the next step. To actually put something else inside of you while the toy was in your ass. You read through your research again and waited for the boys to head out on another hunt, giving you the privacy you’d need. It wasn’t that you didn’t want to tell them, and more than once you’d thought about how good it would feel to have them be the ones helping to stretch you out, get you wet & relaxed… You even knew that if this had all flopped at the first step they wouldn’t have been anything but supportive of your efforts. But you wanted it to be a surprise. You wanted to see their faces, see Dean’s face, when you told him about how you’d been working to be so good for Daddy.
Finally, the boys left for a regular salt & burn in Nevada. You’d sent them off with a teasing goodbye about staying out of the brothels and then quickly went to your room to get started.
You’d already decided to start small, even before reading the helpful Reddit page again. It made sense. So you picked the smallest vibrator you had and set about working yourself up. Before long, you were writhing on the bed, dildo clenched in your ass, pulse wand pressed to your clit. You came once, the pleasure coursing through you. You set the wand down and rubbed slowly at your soaked pussy, feeling the lips flutter at the desire to clamp down on something, but only pulling at the odd pressure the dildo in your ass caused.
After a few moments, you steadied your breathing and reached for the small pink vibrator. It was barely wider than one of Sam’s long, thick fingers and smooth silicone – no bumps or knobs. You were just trying to see if you could stretch and take two at once. You played the end of the toy against your clit, hissing at the stimulation and aftershocks before you slowly drug it down your wet cunt. You focused on your breathing again, hips spread wide, and closed your eyes as you rubbed the length of the toy over the top of your mound and then slowly, ever so slowly, began to push the tip inside of you.
You winced at the oddness of it. The toy in your ass made your pussy feel tighter, smaller, and you shifted on your back trying to alleviate the pressure. It took several small, slow strokes before even half the vibrator was inside you, and you had to stop to breathe again. Your body was tense, the skin feeling too tight all over, even in your toes. You made the smallest of movements with your wrist as you focused on relaxing.
Eventually, you had both toys fully seated inside you and you lay still, concentrating on how your body felt. It wasn’t painful as such, but it wasn’t the screaming orgasm of pleasure the woman in the porno had been selling, either. You winced again as your pussy contracted around the toy, wanting to do something about the foreign presence in your body. So you started stroking it in and out, slowly. The more you worked, the more the feeling of pleasure started to build. You shifted your hips again and gasped as the tip of the toy grazed your gspot and your entire body tensed. The toy in your ass was drawn deeper into your body by the clench of your muscles, pushing the vibrator more firmly against that spot.
“Fuck,” you spit out as you came. The orgasm wasn’t the best you’d had, but it was the most intense in how quickly it had arrived and how it left your legs shaking. You slowly pulled the vibrator from your body and then the dildo and curled up, pressing your legs tightly together at the feeling of emptiness inside you. After a few moments, you reached for the wider dildo – the one you always called Dean in your head – and pressed it inside your aching cunt. Your pussy fluttered wildly around it and tears leaked from your eyes as a third, less intense but more pleasurable orgasm flooded your system. You pulled the toy from you and fell asleep.
When you woke up a few hours later, body sticky and sore, you set about cleaning your toys and then allowed yourself to soak in a steaming bath. You paid attention to your body, cataloguing what hurt and why. When the water started to cool, you got out and dressed in a fluffy robe before heading to the kitchen to make a late lunch. After you were finished, you curled into a chair and started reading again. The entire experience hadn’t been 100% pleasant, but the way your body felt now, the orgasms you’d had… you could only imagine what it would be like to have Sam and Dean, their cocks hard and pulsing, pushing in and out of you at the same time. The thought alone was enough to remind you that you hadn’t bothered to put on panties under your robe and reinforce your desire to try again.
That first morning after had been a sore one, but over the next few days, you slowly got more and more comfortable with the experience, your body quicker to accept the second toy. By the end of the week, you had even fucked yourself to a mind-blowing orgasm with one of the mid-sized toys with the dildo in your ass, while Sam & Dean jerked each other off on the small computer screen. You were careful to keep yourself turned just so from the camera so they wouldn’t see it. They’d both been turned on as hell by the sounds you’d made and you had to admit that some of the excitement on your end was knowing that they had no idea what you had done.
It was another few weeks, however, before you had the chance to do the next to last step, which was fucking yourself with the dildos Sam and Dean had bought for you. They were the largest in your collection, and even though the boys were slightly larger, you figured if you could do this, then you could take the real thing.
When Sam and Dean left to check out a possible poltergeist in Enid, Oklahoma, you were both excited and apprehensive about taking this final step. Your brain panicked at the thought of what would happen if you couldn’t take it, couldn’t stretch to accommodate the largeness of the toys, of Sam and Dean. It took you several tries to regulate your breathing and you actually had to just wait until the next morning after your daily yoga before you felt settled enough to even attempt it.
You laid back on the bed, your skin still sweaty and elastic from stretching. You pulled off your sports bra and threw it in the corner atop your discarded yoga pants and underwear, leaving you naked on the cool sheets. More slowly than usual due to your nerves, you worked yourself up, getting the long dildo in your ass and rolling your hips to get it seated properly.
You lay there, breathing & biting your lip against the now familiar pressure beneath your hips. You slowly dropped a hand between your legs, rubbing long, thin fingers over your mound until your hips were rocking up into your touch, your skin now shining with your efforts. You grabbed the pulse wand and held it to your clit as you sunk two fingers into your wetness. You eventually brought yourself to orgasm with a medium-sized vibrator pressed deep into your pussy, your hips shaking with the pleasure of it.
When the last zings of heat began to die away, you pulled out the vibrator and cupped yourself, feeling the gaping stretch it left behind before your lips began to flutter and contract. You closed your eyes and reached over your head for the lube, squeezing more into your hand and warming it with your touch. You groaned as you slathered it over yourself, adding to the slick slide of your cum. You knew you’d need it.
Finally, you opened your eyes and turned your head, reaching for the wide, purple dildo. You gave a shaky sigh as you coated it with lube, your fingers catching on the realistic veinwork and flared head. You rubbed the now slick tip across your nipples and let it slap down on your belly the way Dean liked to do when he was kneeling next to you. Then you moved so that the head was pressing against your clit, the vein on the bottom sliding easily over your sensitive nub.
“Fuck, Dean,” you groaned aloud. You imagined him between your legs, rubbing his cock over your mound, telling you how proud he was of you – what a good little girl you were for Daddy. Your body clenched at the imagined praise; the way his voice dropped whenever he called you his “baby girl” never failed to make you shiver.
Slowly, so slow it was almost painful, you pushed the head of the fake cock against your pussy and began to press with intent. Your body tightened at the unknown stretch, and you arched your back, both chasing and trying to move away from the feeling of fullness you knew was in store. You wrapped your free arm around your waist and held tight, imagining Sam’s muscled body beneath you, holding you steady for his big brother to sink into.
“Shit,” you cursed as the head was finally seated inside you and you stilled. Your body was trembling, slight jolts of pain from the stretch racing up your nerves. You brought a hand up to your breasts, palming and pulling at the nipples to give a counterpoint to the feelings at the center of your body. You pushed slightly again, hips spread wide as another inch disappeared inside you.
That was the way it went for the next few minutes – a slow push-pull-stretch-slide. You kept imagining Dean’s crooning “so good, baby girl – so good for Daddy,” whenever the toy moved further inside you. You moved your free hand around, pinching at your hips, your tits, your stomach, the way you knew Sam would do. Imagined his voice in your ear, his chest heaving beneath you as he told you how good you felt on his cock.
Finally, finally, both toys were all the way inside you and you didn’t dare move. Your skin felt too tight again, but this time, it felt like it might explode and break into tiny pieces. When you finally pulled at the dildo in your pussy, you did explode. Your orgasm was instant and unexpected. Even more unexpected was the flood of slick that came out of you, coating your hand and soaking the towel you had spread out beneath you.
“Oh Jesus, oh Christ, oh fuck!” you shouted, legs clamping down on your wrist as another orgasm hit on the heels of the first. It was like you couldn’t stop them as long as the toy was buried inside you. You pulled it out as quickly as you dared, your pussy clamping at it as your body cramped and shook. When both toys were out, you lay there shaking and limp, your body twitching like it was hooked up to a live wire.
“Son of a bitch,” you breathed. When you could finally sit up, you were amazed at the wetness that soaked the towel, your thighs and you could even see a few droplets glistening on the floor a foot or so from the end of the bed.
“Son of a bitch,” you said again. You’d never squirted before. Ever. You laughed shakily and curled up on the dry part of the bed to sleep. You’d strip the bed & do the laundry later.
This pattern continued the next three days. As soon as you tried to move the second dildo inside you, you’d cum – hard, fast, and fucking debilitating. If you didn’t squirt on the first orgasm, you were almost guaranteed to do so before you could pull the toy out. And it didn’t seem to matter if you’d cum before achieving the full double penetration or not.
You did more research, once again finding yourself on Reddit, and felt better when you read that many (although not all by a long shot) experienced this same thing. It was something about the added pressure and fullness that triggered it, combined with the intensity of the experience.
It did make you worried about how Sam and Dean would react, though. All of your reading on the subject hadn’t been all good – several comment threads had been full of guys complaining about how messy and gross they thought it was. Even though some journal articles you’d read had assured you that it wasn’t the same as peeing, most of the negative comments hadn’t been so sure. You didn’t want to upset either Winchester with your uncontrollable reaction.
The lack of control was another hitch you hadn’t counted on. When the three of you played, Dean was in control – and you and Sam loved it. Cumming without permission would disappoint Dean greatly, and you didn’t want that. Didn’t want to make him upset with you. You bit your nails you were so nervous about it. If you couldn’t stop yourself from coming with the two of them inside you…
You tried, but it seemed like the added pressure of wanting to hold off made you cum harder than ever.
“Damnit,” you said when you could breathe again two days later. You lay there panting, body covered in sweat and goose bumps, the soaked toys on the towel between your legs. You gulped in air, trying to calm your body when your cell phone rang beside you.
“Shit,” you said, reaching for it and seeing Dean’s name flash on the caller ID. You took several deep breaths before opening the phone.
“Hey baby girl,” Dean said, and you could hear the smile in his voice. You shivered at the term of endearment.
“Hi Dean,” you said quietly, hoping he wouldn’t hear the tremors of your orgasm that still hung in your voice.
“We’re on our way back. Probably won’t make it in before tomorrow night though since Samantha here insists on getting a room tonight.” You could hear Sam bitching in the background.
“Okay,” you said, biting your lip.
“Everything alright, baby girl?” Dean asked. You swallowed hard. “You feeling okay?” You heard Sam ask what was wrong. There was a click that told you the phone was now on speaker and Sam asked his question again, this time his voice louder.
“I’m good,” you answered. “I just… I’ve been... working on something. A surprise.”
“A surprise, huh?” Dean’s smile was evident in his tone.
“Yeah, a surprise.”
“We love surprises, don’t we Dean?” Sam asked.
“I’m all tingly with anticipation, baby girl,” Dean said and you felt that flutter again. “Still wanna get that room for tonight Sam or just drive on through?”
“Get the room,” you said quickly. You wanted the time to really pamper yourself – shave, clean up, and be ready. “Come home safe and well-rested tomorrow.” There was a pause as the brothers pondered over your phrasing. “And no Skyping tonight,” you added.
“Fuck, baby girl,” Dean groaned and you heard Sam sigh.
“You can play with each other,” you offered. “But nothing from me until tomorrow.” You paused. “Is that ok, Daddy?”
“Yeah, baby girl, yeah,” Dean said, voice breathy and you imagined him hard, cock pressed against his zipper. You knew as soon as he hung up with you he’d be pulling over so Sammy could lean over and suck him down.
“Ok then. Let me know when you leave tomorrow,” you said.
“It’ll be early,” Sam told you, anticipation heavy in his voice. The three of you said your goodbyes and you lay back on the bed again.
Now you were committed. Some of the tension left your shoulders. You’d just have to tell them before you got started about the mess and the uncontrollable orgasms. Maybe they had more experience and could help, you thought.
“Tomorrow,” you said quietly before getting up and going through the process of cleaning your toys and running a bath.
***
The next morning you were up early, your excitement and nerves not letting you sleep in. You were already finished with your morning yoga when Sam texted to let you know that they were leaving the motel & would be home sometime around mid-afternoon.
You sat on the bed after taking off your yoga clothes, anticipation tingling through you. You automatically reached for your box of toys and began to stretch yourself out, sliding the long dildo into your ass and grunting with pleasure as your fingers danced over your clit. You teased yourself for almost an hour, never letting yourself cum and never actually working your way up to both large toys inside you. Around mid-morning, you finally brought your pulse wand out and held it to your clit, shuddering and screaming as the tension of your play was allowed to crash over you.
After cleaning up your toys, you took a shower, stretching out against the wall as you shaved your legs and underarms. You had waxed your pussy yesterday, not wanting yourself to be too tender for tonight. You washed your hair and lathered your skin with the eucalyptus and mint scented body wash that Sam had bought for you. He loved smelling it on your skin.
You ate a light lunch and drank a full bottle of water. One of the articles you’d read about women who squirted had stressed the importance of hydration, so you’d upped your water intake. Throughout the early afternoon you prepped – making sure the mattress cover you’d bought was on the bed & covered by the soft cotton sheets. After another session of stretching yourself out to be sure you stayed as loose as possible – this time without allowing yourself to cum – you put your cleaned toys in a box on the bedside table with a full bottle of lube.
Around 2pm, you put together the fixings for an easy supper of sandwiches – you had good reason to hope that the three of you would be ravenous later but also too fucked out to make much of an effort. You drank more water before going to your room to change as Sam texted you to let you know how far out they were.
You stripped out of the casual clothes you’d been wearing and slid a pair of pale pink panties on, the lace sheer and sensual against your skin. Your fingers danced over the smooth skin of your legs, dropping small touches of aromatic oil – a blend of eucalyptus and sandalwood – at the crook of your knee, the small of your back, just below each breast with a line drawn down your belly, and behind each ear. Sam and Dean both loved smelling you, running their faces over your skin.
You pulled out a lacy, white baby-doll cut top and pulled it on, leaving your breasts free and braless. Normally, if you were going out, you’d wear this top with jeans or a skirt, because it just barely covered your ass. You turned and looked in the mirror, seeing the barest hint of pink lace across your cheeks as you stretched. You bit at your lips to make them red and slightly plump, not bothering with makeup because you knew that once you got started, you’d simply sweat it all off. You finger-brushed your hair, leaving it looking a little wild and untamed, knowing how much Dean liked it that way.
When everything was as ready as you could figure to make it, you went back out and sat on the couch, hugging your knees up to yourself under a light blanket to keep warm. Almost exactly when you expected, you heard the grumble of the Impala’s engine as Dean pulled into the garage. You sat and waited for the boys to come in, getting up and tossing the blanket to an arm chair when you heard them coming down the hall.
“Baby girl?” Dean called for you, dropping his bag in the kitchen. Sam followed, calling your name. Both of them turned at the same time and saw you leaning against the back of the couch, your long bare legs spread slightly & your breasts thrust out as you leaned back on your arms.
“Hi Sammy,” you said, not moving. “Daddy.” Sam and Dean’s breathing deepened, & you could see them shift as their bodies reacted to you. As one, they moved in your direction. Dean pushed Sam to you first & you eagerly accepted the kiss he gave you, smiling as he inhaled deeply, nose pressed behind your ear.
“You smell amazing,” he whispered before turning you around and holding you around the waist while Dean walked up. “Doesn’t she, De?” Dean made a show of leaning down to sniff your neck, nuzzling at the skin before biting at it slightly.
“Smells good enough to eat,” he said, his grin predatory as he moved in for a kiss. You felt his cock, hard in his jeans, nudge at your belly. When Dean pulled back, you took his hand and Sam’s and led them around to sit on the couch.
“Are you ready for your surprise?” you asked as they sat down, one on either side of you. Each man put a big, possessive hand on your thigh, their callouses raising goose bumps on your flesh as they stroked you.
“Been thinking of nothing else, baby girl,” Dean said. “Sammy here practically creamed his jeans all the way home.”
“What have you been up to?” Sam asked, his hand squeezing down your thigh to rest over your knee.
“Well,” you said softly. “Do you remember several weeks ago… we were watching that movie Dean brought back. The one with the threesome? It had the two men and the woman?” You watched their eyes darken, their chests expand with their breaths. “The one where they shared her? At the same time?”
“I remember,” Dean said, voice deep. You licked your lips.
“You both seemed to really enjoy it,” you said. “Like maybe you wanted to do that. Share a woman, both of you inside her, at the same time.” The tension in the air was palpable. You reached out and lay your hands, so dainty in comparison to theirs, on each of their thighs. “Like maybe you were thinking about sharing me… at the same time.”
Sam turned on the couch, bending his leg up to face you. His hand started traveling back up your thigh now, heading towards the junction of your hips. Dean’s fingers moved up to trace your bare arm, just above the elbow. When they didn’t say anything, you swallowed and continued.
“So, I started doing some research,” you admitted. You saw the smiles on their faces and blushed. “I’ve been learning how it works, and...” Here you paused and looked over at Dean. “I’ve been practicing.” Both men froze.
“Practicing, baby girl?” Dean asked. There was an edge of danger to his voice now. You were quick to move your hand up to his chest, turning to face him.
“Not like that, Daddy, I swear!” You felt Sam scoot up closer behind you, felt him nuzzle at your neck and breathe in the scent of your hair. “I used the toys… the ones you bought me for when you’re gone.”
“Jesus,” Sam said into your hair. You could feel him rocking his hips behind you, getting little nudges of friction from his jeans. Dean licked his lips, drawing the bottom one in to worry with his teeth.
“You been practicing taking the two of us with your toys, baby girl?” he asked. You nodded.
“I wanted it to be a surprise, Daddy,” you whispered, crawling into his lap and straddling his hips. His hands naturally fell to hold your waist, his pinkies dipping down to play with the edge of your lace panties.
“And since you’re telling us about it now,” Sam said, scooting closer to the pair of you. He alternated between nipping at your bare arm and running a hand over Dean’s thigh, his thumb brushing against your ass on the upstroke.
“It means I’m ready,” you confirmed quietly. Dean rolled his hips up into you and Sam groaned, biting harder at the back of your arm just near the shoulder. You let them push against your body, covering your arms and neck with kisses for a moment before you brought a hand up to Dean’s face. He pulled back.
“What is it, baby girl?” he asked, rubbing a thumb across your lips.
“There’s some things you need to know,” you said, ducking your head. You felt the blush coming, unable to stop it. Your hands tingled with nerves. Dean met Sam’s eyes and then suddenly you were in the younger man’s lap, your legs spread out over Dean’s as they lay back in the corner of the couch.
“Salt?” Sam asked quietly. You looked up at the use of your safe-word. Salt meant wait, stop. You bit at your lips but shook your head.
“Matches,” you answered. Matches was the yellow word – go slow, caution, pay attention. Dean’s hand was a warm, safe weight on your ankle.
“What is it?” he asked again, looking at you carefully.
“It’s about what happens when I’m full like that – with the toys.” Sam and Dean nodded, Sam’s fingers lightly scratching at your scalp at the back of your neck. “It’s never happened to me before, but when I have both of them in me and I start to move one of them, I…” You shook your head. This was ridiculous. You were a grown ass woman who had beheaded vampires and was in an adventurous sexual relationship with two brothers. This should not be embarrassing. “I squirt,” you finally said.
“Son of a bitch,” Sam whispered and you felt his cock hardening again under your thigh.
“A lot,” you added, smiling wryly at him. He grinned back and then you looked over at Dean. “I’ve tried not to,” you said quietly when he didn’t speak. “That almost seems to make it worse.” Dean’s hand on your ankle tightened.
“Baby girl, are you afraid I don’t want to be soaked by you?” Your breath hitched and it was a second before you remembered how to breathe again. You nodded.
“I know some guys don’t like it,” you whispered.
“I love how wet you get for us,” he answered back, just as quietly. “The idea of you cumming – drenching us – is not a problem.” You drew in a deep breath and relaxed a bit.
“There’s something else,” you said, eyes on Dean. This time you felt more confident, less embarrassed. “When I put them both inside me, I can’t control it, even if I just came. I can’t stop myself from cumming. It’s almost instant, and I just keep cumming while they’re in me. I…” You stopped. “I’m sorry, Daddy, but I don’t think I’d have time to ask your permission.” Dean stood and pulled you to him, catching your lips in a deep, smooth kiss.
“Tell you what, baby girl,” he said against your lips, his eyes sparking with lust. “How about as a reward for being so good for me and Sammy… You don’t have to ask permission tonight.” You felt Sam stand behind you, and you sighed at being between them.
“Ok, Daddy,” you nodded.
“So,” Dean asked, easing a thigh between yours. “Salt?” he asked. You shook your head.
“Matches?” Sam asked, mouthing at your shoulder. You shook your head again and smiled as you slipped out from between them to head in the direction of your bedroom.
“Gasoline,” you finally said, giving the green word. You heard them following behind you – all systems go. You danced ahead of them on light feet, keeping just out of their reach until you were in the hall and then you heard Sam’s heavy strides get longer and you giggled as you ran for your door.
“Gotcha!” Sam hollered as he grabbed you around your waist and slung you over his shoulder. Your feet kicked out as he slapped at your ass playfully and started walking to Dean’s room.
“No, wait,” you said. “My room.” Sam paused and looked at Dean.
“You heard the lady, Sammy,” Dean said turning the younger man back to your door. Sam carried you in and sat you down, looking at the simply stripped bed – just a bottom sheet covering it – and the lube on the table.
“You are a master of surprises,” he said, smiling. You blushed and then stepped back, looking to Dean. The older brother grinned at you and nodded as he pulled his shirt off over his head and began to kick off his boots. Sam did the same, both brothers quickly working to strip themselves until they were completely naked, their clothes a combined pile in the corner of the room.
“May I, Daddy?” you asked, walking over to them, the light brush of lace between your thighs all the more noticeable because you were the only one dressed now. Dean nodded and you fell to your knees between them. You licked at your palm before taking Sam’s cock in hand, stroking it while you began to lick and suck at Dean’s. You alternated between them until both were rock hard and slick with spit and pre-cum. You stood and grinned, licking your lips.
“Let’s get you undressed, baby girl,” Dean said and you raised your arms. Sam knelt at your feet, hooking his fingers in your panties to pull them down your legs while Dean easily lifted your top over your head and tossed it behind him. Sam shifted more in front of you and lifted one of your thighs to rest on his shoulder. You grabbed at Dean for balance as he leaned down to lick at your breasts, tongue rolling over your nipples in time with Sam’s tongue rolling over your clit.
When you felt the first brush of Sam’s finger down the cleft of your ass, you groaned. He pulled back, chin shiny with your arousal, as he felt the lube around your hole.
“Have you already been playing with yourself, baby?” Sam asked, testing the stretch of your rim with the pad of his thumb. You nodded.
“I wanted to be r-ready,” you stuttered out as Sam pushed his thumb inside you. Dean stood up and brushed his fingers through your hair, watching your face as Sam went back to tonguing your slit while he pumped his thumb in and out of you.
“And are you, baby girl?” Dean asked, thumbs running over your closed eyelids. You nodded, gasping as Sam pressed his face deeper between your legs, tongue sweeping inside you.
“I can feel it,” he said, pulling back. “I can feel my thumb.” He made eye contact as he brought is other hand up and slid two fingers inside your pussy. You trembled as you felt him rub his fingers against each other through the thin membrane that separated them. Sam played for a few moments before pulling his fingers completely from you as Dean gripped his hair and pulled. Your leg fell from his shoulder and you stood watching as Dean licked your juices from Sam’s cheeks and chin.
“Get on the bed,” Dean said when he was done. He gave a small slap to Sam’s ass. “Both of you.” He walked over and sat at the end of the bed, stroking his cock as you and Sam climbed into the middle. He let his eyes rest on you. “What do we do first, baby girl?”
“Stretch and relax,” you said, reaching for the lube. You saw Dean’s grin as he figured out why you’d suddenly started doing yoga. You held the bottle out to Dean but he shook his head.
“Stretch her out good, Sammy,” he ordered. You shuddered.
“Yes sir, De,” Sam replied, taking the lube and laying you back on the pillows. He set it down by your hips and then lay between your legs. “I believe relaxation was also mentioned?” he said with a wink before diving back in to lap at your clit. A cry of pleasure was punched from you and you clenched around his tongue, automatically fighting off your orgasm before Dean got your attention by grabbing a toe and pulling.
“You have permission, baby girl, remember,” he said and you wailed as you let your release hit, feeling the tremors and tension from your teasing this afternoon and the heightened state of arousal that the brothers caused in you by just existing collide to wash over you. You slumped boneless, legs splayed wide around Sam’s shoulders. He smiled proudly and reached for the lube.
“Fuck,” you breathed as Sam slid a lubed finger in your ass, the soft squelch of the stuff audible in the room. The sensation wasn’t new by any means at this point, and yet it was totally different. The width of his fingers, the knob of his knuckles – it’d been so long since the three of you had done any assplay that it all felt brand new. It didn’t take long before Sam had three of his thick, long fingers working inside your ass, his tongue still playing with your clit occasionally, but more often than not he just licked at the edges of your pussy, sucking your labia between his lips, pulling back, and then letting go.
“Ok, ok,” you breathed as a smaller orgasm ran through you while Sam had your clit in his teeth and you felt Dean’s fingers on your ankle. “Ok, I’m ready.” You loved that the brothers trusted you enough not to ask if you were sure. Sam simply placed a kiss to the top of your mound, his lips sucking at the smooth flesh, before pulling his fingers from you. Your body instantly clenched at the loss.
Dean gripped your ankle again, grounding you, while Sam peppered your stomach with kisses.
“Sam,” you tried, swallowing to get your voice under control. “Sam goes on his back, up here.” You patted at the pillows beside you and Sam quickly moved into place. You got on your knees beside him, leaning down to lick at the lines of his abs, stroking his cock. You reached over and grabbed Sam’s hands, still slick with lube, and wrapped them around his length. You helped him spread the lube, adding a little bit more as you remembered that Sam was in fact bigger than the toy you’d been practicing with. You knew he would fit – he had before – but you were still nervous about getting this all right.
When he was sloppy and panting, you swung your leg over him, facing where Dean sat at the end of the bed, his gaze intent on what you were doing. You settled on your knees, Sam’s cock hard and thick at your opening.
“Go slow, remember” you warned him as you grabbed his cock and held it steady while you began to sink down. You gasped at the pressure, but didn’t stop as the head finally breached your rim. “Oh, fuck,” you whimpered. Dean watched you carefully, reaching a hand up to move your bangs off your now sweaty forehead. Your grin was measured and careful, but he saw the truth in your eyes that you were still good. He watched you sink, ever so slowly, his eyes admiring the muscles of your thighs and arms as you controlled the slide of Sam’s cock into you.
“How’s she feel, Sammy?” Dean asked, his hand now resting on Sam’s foot, thumb rubbing over the jut of Sam’s ankle bone.
“So fucking tight, De,” Sam grunted, his face strained as he fought his body’s desire to slam home. Dean whispered praises to the two of you, his voice soft and dark as you finally managed to take Sam completely inside you. The two of you panted for a moment and then you began to slowly bounce on his cock, leaning back to rest your hands on his abs. Sam placed one hand between your shoulders, the other at your hips to balance you as you rocked on him, your strokes slight.
“Daddy,” you breathed. “Touch me? Please?” Dean eased forward onto his knees, his cock red and swollen against his belly. He reached out and lightly stroked his fingers across the top of your mound. You groaned as he played with you, never quite pushing his fingers inside you. You were close to another orgasm and you weren’t even holding off for permission – you just weren’t there.
Suddenly, Dean reached out and slapped the tips of his fingers down across your cunt, barely catching against your clit. You arched your back and screamed as you came, pussy fluttering at the lack of something inside it, your body squeezing Sam’s cock tight within you. Dean slapped your pussy again and while you were panting through the aftershocks, he leaned down and took your clit in his mouth.
“Fuck, yes – yes, Daddy, please,” you begged. Sam groaned beneath you, adding his own movement, stroking his cock in and out of your body more easily now. You both froze as you felt Dean slip a finger inside you. He rubbed at the thick vein of Sam’s cock through the membrane separating them and Sam hissed.
“De, stop, I wanna hold on.” Dean instantly pulled away and reached under you to press at the base of Sam’s cock, effectively helping him come back from the edge. Sam’s hands shook on you.
“She has permission to cum whenever she wants,” Dean said against your thigh. “You don’t, Sammy. You gotta wait until I’m inside her, too.”
“Yes sir,” Sam gasped.
“Do you need a ring?” Dean asked.
“No sir,” Sam shook his head. “I can do it.” Dean leaned down and licked at the base of Sam’s cock.
“That’s my good boy,” he said. Then Dean pushed his finger back inside you, crooking it against your gspot and making your stomach tense with pleasure. He added a second finger. “You feel so tight,” he said. “You always feel good, but with Sammy already inside you… Damn, baby girl.” You nodded.
“Feels so good, Daddy,” you said. “More – give me more, please? Please Daddy.” Dean gradually worked with you, licking at your thighs and your stomach as he fingered you, occasionally having to pull out and grab Sam’s cock when the younger man mewled and begged.
“I’m ready, Daddy,” you said after what felt like forever. You hadn’t cum in a long time, holding off so as not to torture Sam when you would squeeze him, your arousal running down into your crack to coat his cock. Dean sat back on his hips, reaching for the lube again. He’d already applied what felt like half the bottle, but you knew it was necessary.
“Ready for what, baby girl?” he asked, spreading the slick stuff over himself once it warmed in his palm. You collapsed back onto Sam, your arms laying out to the side as the younger brother wrapped his arm tight around your waist, grunting at the new angle of his cock inside you.
“Ready for you, Daddy,” you panted, splaying your legs out as wide as they could go. You reached down and rubbed small circles over your pussy. “I want your cock in me, Daddy,” you said, throat tight with need. “Want you to fuck me. Want you and Sammy to fuck me together.” Dean inched forward and leaned down to press his face into your stomach under Sam’s arm. He smelled the salty clean scent of your sweat and the barest hint of sandalwood. He nipped at the soft flesh, just barely hard enough to bruise.
“Gasoline?” he asked when he was just outside you, the wide flare of his cockhead rubbing at your stretched, slick cunt. Both you and Sam responded accordingly and Dean slowly began to push inside you.
“Ahhhhh!” you cried out, hands coming up to pinch and twist at your nipples harshly. The sharp slice of pain helped focus you and you reached your free hand down to pinch at the tight skin over Sam’s hipbones. He grunted in response, dragging in huge lungfuls of air underneath you.
Slowly, ever so slowly – just as slowly as you’d been that first time with the toy – Dean sank into you. Once again, praise fell from his lips, bathing you and Sam in warmth and pleasure.
“So good, baby girl. Taking Daddy’s cock so good. And Sam – such a good boy, Sam – holding so still for me. For her. Feel so good, baby girl. Easy Sammy, easy – don’t cum yet, baby boy. That’s Daddy’s good boy. So good…”
When Dean finally bottomed out, you held your breath, your skin already stretched so tight. You knew it was coming, you knew you were going to explode.
“Remember, baby girl,” Dean said from somewhere above you – his voice was firm with his control to not just rut against you. He could feel the hard line of Sam’s cock inside you. He could feel how tight you were, like your skin was stretched to the breaking point. “You have my permission – don’t hold anything back.” And with that, Dean began to move.
“Fuck!” you screamed, feeling the head of his cock dragging over your gspot from where the pressure of Sam inside you pushed him forward. You came instantly, every molecule inside you feeling like it was exploding outward. And then Dean pushed back in and it was like a reverse reaction – instead of exploding out, your body drew in. All the atoms and nerves and cells that made up your flesh drew down tight inside you and forced pleasure out into the empty space they left behind.
“Oh, God!” you cried out, hands fisting in the sheets by Sam’s hips. Sam grunted in your ear and his arm was an iron band across you, holding you down while Dean sank into you. Gibberish fell from your lips as you felt that familiar wetness flow out over your thighs.
“Jesus,” Sam muttered as you squirted, your slick flooding out around Dean’s cock and down onto his thighs. He felt it run over his hips, some of it even running between your ass-cheeks to pool on his stomach.
“Oh, my sweet baby girl,” Dean growled, dropping a hand down to rub at the top of your pussy while he kept fucking into you. You tried to scream, but couldn’t, your breath all gone and your body only existing for the pleasure that was so strong it was almost pain. Dean shoved in hard and deep, holding himself still as he brought his fingers up, offering them to Sam over your shoulder.
“Want a taste, Sammy?” he asked and Sam dutifully took your slick from Dean’s fingers, moaning around the taste. Dean touched you again and you whimpered. “Did you ever taste yourself, baby girl?” You nodded – you’d licked it off your fingers and wrist the second day. Dean brought his wet fingers up and swirled them over your chest, dripping the wetness on your tits and rubbing it into the pebbled skin of your nipples. He leaned down and licked it off, smacking his lips.
“Daddy…” you mewled. Your pussy clenched and clamped down on Dean’s cock inside you, fluttering every time he shifted. You honestly didn’t know if you had another orgasm in you, but you knew you wanted to feel the final bit – the one step you’d never actually been able to replicate with the toys, no matter how lifelike they were. “Want to feel you cum in me,” you finally said, fingers clutching at his shoulders. “You and Sammy – together. Want to feel it, please…”
Dean leaned down and lapped at the skin between your breasts, teeth grazing the tender flesh as his fingers tightened on your hips.
“Please, De,” Sam begged, his voice hoarse. “Need to cum, please sir.” His body shivered under you. Dean nodded as he sucked a dark mark into the flesh over your ribs and then leaned down to bite at Sam’s forearm stretched over your waist.
“You’ve been such a good boy, Sammy,” Dean said, licking at the teeth marks he left behind. “Ok.” Dean leaned back on his knees. He took a firmer grip of your waist. “You can cum, Sam,” he said and thrust in hard.
Dean set up a brutal pace, his hips pistoning in and out of you while you screamed, tears leaking from your eyes. You felt more than heard Sam crying out beneath you, his hips stuttering up as he tried to fuck you at the same time.
“Shit, so good, so good,” he muttered. “De, I’m g-g-, I’m gonna…” Sam howled as he raised his hips up and used his arm to pin you to him when he came. Dean grunted as he felt Sam’s cock twitch inside you and you felt another bout of wetness soak over Dean’s cock as your body reacted to the feel of Sam’s hot cum filling you.
“Daddy, please,” you cried until Dean’s strokes faltered and he bit down on your ribs hard as he came, his cum splashing inside you and running out thin and watery as it mixed with your slick wetness and squeezed out around his cock to dribble down on Sam’s thighs.
You weren’t sure, but you thought you must have passed out because the next thing you knew, you were being carefully lowered into a steaming bath, with Sam and Dean carefully washing you with soft cloths, the scent of eucalyptus heavy in the air. Dean washed everywhere, between each finger and toe, behind your ears, across your breasts. His hand swiped between your thighs, but didn’t linger – his touch was caring now, not sexual.
Sam washed your hair, his fingers firm as he massaged your scalp. When it came time to rinse, Dean supported the back of your neck with one hand as you tilted your head back and formed a shield at your forehead with the other so none of the soapy water got in your eyes. You were boneless and empty, content to let them move you as they saw fit, all the while murmuring soft nothings and snippets of approval over you.
When they finally pulled the plug, Sam stood behind you and helped you stand, his arms a firm cage of support while Dean ran a fluffy towel over your entire body. He also ran the damp towel over Sam’s back, and down his thighs and legs, rubbing him down and massaging his muscles, telling Sam how strong he was and how good he was and how happy he’d made Dean.
After Dean was done drying himself off, he stepped up to take you, easily lifting you into his arms and heading out down to his room. Sam went ahead to open the door and pull down the sheets. Dean laid you out on the soft mattress and you stretched, feeling the sore pull of your muscles, but also feeling completely blissed out. Sam climbed in, spooning up behind you and wrapping you up tight against his firmly muscled chest. Dean turned out the lights and padded over, climbing in on the other side, reaching over your body to wrap an arm around Sam as he pulled your face into the crook of his neck.
A few hours later, the three of you woke, starving – just as you’d predicted. After lingering in the safety and contentment of being between them, you urged them up. Robes were donned and an easy silence followed you to the kitchen where the boys insisted on pampering you by taking care of putting the fixings together. While you sat on the couch, bodies sprawled out so you could touch one another, Sam looked at you and smiled.
“So,” he said quietly. “What do you think it would take to make you squirt every time?”
END