You never, not once in your entire life, expected to be in THIS kind of situation in your life. Being the girlfriend of two men. Not just any two men. Two brothers. Two brothers who had no problem with threesomes and loved to torment you sexually any opportunity they got. It was all a fun game to those sick, sadistic bastards. The fact that you enjoyed it immensely didn't help their egos.
They knew just how to team up to cause you the greatest torment too. Like today. This was the worst torture they'd ever come up with. Being a trio of hunters meant that sometimes you had to do undercover work.
That morning, Dean had cooked a big breakfast. Sam asked you to help clean up but you kind of hated doing cleanup work so you tried to get out of it by excusing yourself to shower.
"Not so fast," Dean said. "Clean up the kitchen first, shower after. Then we can take off for the case."
"C'mon!" You said. "Sam's got it, don't you Sam?"
"Help me out here," he said, trying to get you to join him by giving you a sweet puppy look. You weren't going to fall for it. You had done the dinner dishes, surely you could skip out this one time?
"No, I don't want to," you don't know where your random petulant mood came from. Normally you weren't this childish but sometimes when you were tired out or content, a little bit of a devilish side came out.
"Dean?" Sam turned to look at his brother. "Did you hear that?"
"I believe I did, Sammy," Dean said, a smirk blossoming on his face. "It sounded like she said she wasn't going to behave herself."
"Interesting," Sam said, an identical smirk crossing his features. You gulped. Never a good sign when the Winchesters began to act and think in synchronicity. You stood your ground though. You didn't want to do the dishes and you weren't going to be bossed about by a pair of tall boys.
"Fine, you don't have to do them," Dean said. You smiled slightly, victory in sight.
"If..." Sam said, trailing off. A blush crossed your features. You could sense where this was headed and it wasn't going to end well for you.
"If you take your punishment like a good girl," Dean finished, crossing his arms and tilting his head, waiting for your response.
"Oh...kay," you said slowly, not knowing what kind of punishment they would cook up but knowing it wasn't going to be any worse than having to do the dishes.
The rest of the day proceeded normally. You all went to your respective rooms to change and prepare for the hunt. You showered like you'd wanted and packed your things while Sam did the dishes and Dean readied the car. The hunt looked like a normal salt-and-burn but it was several hundred miles away and would take you half a day to drive out.
Eventually you forgot about punishments and disobedience, getting into the spirit of the road trip, jamming out to Zeppelin with Dean, helping Sam research more about the case, generally enjoying the freedom of the open road with your favorite boys.
Despite the freedom and enjoyment that came from car trips with the boys, it was still nice to get out and stretch your legs when you reached Boone City.
"I need to go," you mumbled as you made a beeline for the motel restroom. Part of the reason you escaped was to change into your FBI attire in peace. You didn't mind changing in front of Sam and Dean but it was kind of distracting for them and could lead to fun that would sidetrack all of you.
Shimmying into the tight black skirt was a chore. You preferred the freedom of jeans and loose, flowy tops to the FBI suits. At least the boys enjoyed seeing you dressed up. They'd be thinking about you all day and by the time you all got back to the hotel, they'd be ready to jump you there and then. Worked out in your favor.
You exited the bathroom and as predicted, Sam and Dean's eyes were drawn to your figure in the tight skirt, heels and pinned up hair.
"Later," you promised with a wink. Dean pulled you close for a kiss before Sam tugged your arm to kiss you as well. They kissed differently. Dean was all heat and tongue and tasted of whiskey and cinnamon. Sam was gentle and soft but you never forgot who was the dominant one when he kissed you.
You left the room, settling into your usual seats in the car. Sam always rode shotgun and you took the seat right behind Sam.
Your case took you to the home of Annabelle Winterbourne. She was the wealthy widow of a large estate and had 3 maids die in her employ in the last month. She was a smart woman who believed something was amiss with her manservant.
She insisted that you come to her dinner party that evening and observe Andrew for yourselves. He had been away on estate business during the day so you'd have the perfect opportunity to see if he was indeed possessed.
None of the guests knew you were "FBI" so you were going double undercover as friends of Annabelle for the dinner party. Sam and Dean would be able to get away with their FBI suits but lucky you, you were required to find and purchase a dress for the party in 2 hours. You grumbled and groaned but didn't mind too much because with the nature of your lifestyle, you didn't get to go shopping very often. You had to work quickly though so you headed out with the car while the boys stayed at the hotel.
Finding a dress was surprisingly not as difficult as you had expected. You picked out something that complimented your skin tone, wasn't too tight but looked good on you and hurried back so you could prepare.
When you entered the room, the boys were sitting at the tiny motel table drinking beer and they looked at you at the same time.
"We figured out your punishment," Dean announced. You gulped. You'd forgotten all about the punishment situation.
"Here," Sam held up a tiny device in his palm. Your recognized the little silver thing instantly. It was a pocket vibrator, YOUR pocket vibrator, in fact. It was something that Dean had gotten you as a birthday present a few months back and you cocked your head, curious as to what was going to happen.
"You get to wear this tonight," Dean said, smirking. "All night."
"And we get to hold onto the remote," Sam added. "All night." Their identical, self-satisfied smiles spoke volumes. They'd clearly been plotting this while you were out shopping.
"Sounds like fun," you said with a smirk back at them. As far as punishments go, this didn't seem as bad as you expected.
"You can't give yourself away," Dean added. You nodded, naturally. "And you can't orgasm until we're home." The rules seemed simple enough. Sam ushered you into the bathroom. Part of their rules was that one of them had to insert it, to make certain you weren't faking.
You felt Sam's strong hands grip your waist as you lowered your panties. You were embarrassed that was all it took for you to start becoming aroused. Your cheeks heated up and you hoped Sam didn't notice.
He may not have noticed your arousal at first but he did when he slid the vibrator between your legs, feeling how you were already beginning to become slick with need. He smiled and took longer than necessary arranging things, fingers brushing against your entrance as he teased you slightly.
"Comfortable?" Sam asked. You nodded, staring up into his eyes with lust. Your hips twitched towards his involuntarily and he chuckled.
"Well it looks like the party is getting started," Dean said, pushing the door open to watch as Sam slowly slid his fingers out from between your damp folds.
"She's all ready," Sam said, nodding his head towards his brother. Dean tilted his head, watching you carefully as his hand disappeared into his pocket.
You jerked in shock as you felt the flutter of vibrations against your clit. It was just a low thrum, barely any pressure at all but it was still enough to increase your arousal twofold.
"Still comfortable?" Sam asked, smirk widening. You let out a carefully controlled breath and looked up at their expectant faces. You weren't going to give in easily. You nodded defiantly.
"Yup," you said. Dean walked out of the bathroom, leaving you alone with Sam for a moment.
"You're going to do this," Sam said quietly to you. "You're going to be a good girl and take your punishment, aren't you?" It was less a command and more a moment of reassurance. You knew Sam well enough. You nodded again and he left as well so you could get dressed in peace. At least, you thought that was why they had walked out of the room. It seemed Dean was merely testing the remote though, because the speed picked up and you jerked again in surprise. It was only a notch higher but that was enough to make you start questioning your resolve at enduring this 'punishment'.
"Still working?" Dean called.
"Yup!" you called back. Abruptly the vibrator shut off and you felt a twinge of disappointment but you had to get ready.
Dean crossed the room to follow you into the bathroom. "I just wanted to tell you that tonight, if you manage to get through this unscathed, I'm going to enjoy fucking you into oblivion for wearing that damned skirt today," he said, giving you a wink before disappearing to let you get ready.
The boys waited an hour for you before Dean was making noise about leaving. Dean was the worst at waiting for you to finish dressing. Sam had a modicum more patience but barely. They headed out to the car and you rushed the rest of the curlers off your head and sprayed Big Sexy Hair liberally around before grabbing your ridiculously tiny clutch and rushing out the door.
You flung yourself into the back-seat with all the grace of a newborn giraffe. "Sorry, we can leave now," you said. The car took off down the road towards the Winterbourne Estate. The vibrator pressed against you more now that you were seated. You tried to ignore it though. It was easier now that the device was off.
As you approached the gate, you tried to focus on the case. You were prepared with your own gun safely holstered on the outside of your thigh underneath your dress. A vial of rock salt sat dangling from a chain, in between your cleavage.
The gate opened and Dean drove the car down the winding lane to the front drive. A man approached the car and opened the door for you. Sam hustled out and grabbed your arm before the other man could. It was kind of cute how possessive the Winchesters were of their girlfriend. Sometimes.
Dean came out of the drivers side, whistling low when he caught sight of you in your dress. "Wow," he said. Sam nodded his head in agreement.
Based on Annabelle's insistence, your 'cover story' was simple. Dean was your husband and Sam his brother. The boys were relatives of Mrs. Winterbourne on her side, visiting from New York City for the first time since you two had gotten married.
Dean took your arm, palming something into Sam's hand before walking with you up the steps of the house. You almost didn't even notice what had transpired until the moment you stepped foot in the house. A low vibrating settled against your core and you whipped your head around to glance at Sam who just gave you an innocent look and shrugged.
So it had begun.
The first twenty minutes were alright enough. They had drinks in the lounge and Sam nosed around the house while you and Dean made small talk with boring socialites and self-indulgent millionaires.
You had just gotten used to the low thrum of the vibrator when an intense jolt forced you to almost yelp in shock while you talked to Mr. Whatsit-the-Financial-Man. He glanced at you with mild concern but you put on your best smile and distracted him with details of your wedding.
The vibrations were intense and insistent and you were suddenly so aroused you could hardly keep focused but you gritted your teeth and bore through it with false cheer. When this evening was over you were going to fuck them both until they couldn't walk straight tomorrow. That was going to be your revenge.
The vibrational intensity increased again and you almost fell out of your chair as you felt the change.
Sam returned, shaking his head slightly to indicate he had yet to find anything significant in the house. It was Dean's turn to snoop around while Sam stayed behind. Dean excused himself and suddenly the vibrator was on a low setting again. You relaxed slightly, feeling a touch better at the lowered setting.
Relaxing was a mistake though because the next second you were jolted alert by the fact that it had gone to what was undoubtedly the highest setting on the vibrator. You squirmed in your seat trying to pay attention to the conversation, make sure that no one could hear the intense vibrations coming from your knickers and also not give away the fact that you were helplessly trying not to orgasm with every part of your being. Sam stroked a light feathery touch against your inner arm, causing you to shiver.
"Cold?" he asked you sweetly. You tried hard to keep your composure and NOT glare at him but it took everything you had. Your entire body was alight with sensation. You clenched your teeth together, trying not to let a moan escape your lips as you rocked against the vibrator in your chair. Sam put a hand on yours, stilling you. He was reminding you to keep control and you felt a helpless anger at him. You didn't know if you wanted to rip his clothes off right there or slap his face for tormenting you. Or both.
Sam coughed and kept his hand on your thigh. It was a form of reassurance, it was a sign that he knew you were struggling to obey but he believed you could do it. A reminder of the fact that he wanted you to succeed.
It was difficult but you stopped squirming as hard. The intensity began to lower and you breathed through your nose, feeling your resistance grow stronger.
Dean came back in the room and glanced at you and Sam. Sam was sitting there chatting with some kind of mustachioed diplomat with a nonchalant expression while squeezing your thigh. Dean came and sat next to you on the other side. Just when you thought you could do it, when you thought you were on the verge of conquering their stupid punishment, the vibrator began to pulse again.
The settings were changing too fast for you to keep up. You continued to breathe evenly but the resistance you had was waning. You felt the orgasm begin to build.
"What do you think of the situation on Wall-Street then, Mrs. Plant?" Mr. Whatsit-Financial-Guy asked.
"Hmm?" you tried to keep your composure.
"Yes, what do you think of it, darling?" Dean asked. Sam intoned his head towards the conversation as well, curious to see how you handled this conversation as you started to sweat with the effort of keeping yourself calm.
"I-I..ahh," you squirmed a little in your seat as you concentrated on your words. "I think it's really all about...." you trailed off as the setting went way back down once again. Sam, obviously. You took a deep breath and put on a better fake smile. "I really think that it's all about the market these days," you said pleasantly.
"Really?" the man asked.
"YaAAHH" you yelped as the remote must have been passed back to Dean who turned it to the highest setting once again and you felt yourself rock against the seat, your orgasm building again. You bit your lip, trying not to break down and cry at the table with effort from keeping it at bay.
"I am just so passionate about the market," you said insistently, in a louder voice than you normally might but not quite shouting.
"Really, I had no idea darling," Dean said, adjusting the settings to a medium buzz. He leaned against you, pressing a hand against your thigh to squeeze it tightly. The touch was almost enough to bring you crashing over the edge but you couldn't come yet so you forced yourself to think of the most unsexy thing you could imagine.
For some reason an image of a fat Crowley smoking a cigar like the bulldog in All Dogs Go to Heaven popped into your mind. It worked but you began to giggle, quietly at first but then louder and more raucous.
"She's just very excited," Dean told the man. "She's invested a lot recently and her stocks are soaring." The man nodded in understanding.
"Wonderful," he said. "What stock have you got? What should I be putting money into at the moment?"
"Ahhhh," you hissed through your teeth. You still had what felt like hours and hours to go.
"Excuse me," you say as you rise. You have to get away. Even if you can't orgasm yet, you have to get away for a moment.
"Sam, make certain Y/N knows where the facilities are at," Dean stage-whispered. He was really enjoying acting like a high-society frou-frou.
"I'll show you," Sam said, leading you away from the dinner table. He steered you by the elbow into the hallway.
"You're halfway through," Sam said as he pressed you against the wall and gave you a soft kiss. "You can do this."
"I can't," you said, voice shaky with emotion. "I can't do this anymore, please," you beg. Your eyes are tearing up with the thought of being forever on the edge of orgasm for the next several hours.
"You can," Sam said gently, but firmly. "I know you can. Now get back in there," he smacked your bottom lightly and you jumped and took a deep, steadying breath.
The rest of the evening passed in a blur. You could barely concentrate between rounds of 'let's see how crazy we can make Y/N". Somehow you managed to make it through this ruse of a dinner in one piece but you had no idea how.
You were punch-drunk by the end and stumbling out the door. The boys hadn't seen enough suspicious activity right then and there to make any moves so they decided to research more about the Estate first and they bundled you into the car.
You were trembling, sweaty and aching with need beyond the normal boundaries of human control. You had no idea how you were holding back.
In fact, as soon as you got in the car, the tears started. You didn't even realize it at first. Cresting on the edge of orgasm for 3 hours was just too much and you were overwhelmed by the emotional and physical sensations. You stared out the window of the back-seat, silent tears streaming down your cheeks.
Somehow the brothers, without even looking, have sensed you've reached your limits. As soon as you get out of the car, they're upon you, brushing away tears and tugging at your clothing.
The second everything is freed and you're naked before them, Dean goes to town on your mouth while Sam fingers you, bringing you quickly to the biggest release you've ever felt in your life. You slump against them, just relieved to finally feel something other than slow torment. They work you over again and again, bringing you to orgasm several times in a row until you're begging them to stop because you're too sensitive to go further.
The three of you lay in bed together, pressed together with you in the middle. You're in a Winchester sandwich and you're drifting off, tired from your adventures today. Sam is stroking your hair while Dean kisses your face gently, lazily, sweetly. They're telling you how good you were for them, how much you pleased them and how well you did. You accept the praise without responding, you're too tired and spent for conversation.
"So," Dean says just as you're drifting off. "What did you learn today?" he asked, nudging you so you're more awake. You just want to sleep though and you struggle to put words together and answer him. "Tell me and you can go to sleep."
"Do the damned dishes," you mumbled and the brothers laughed as you faded into unconsciousness in their arms.