Chapter 1: "Friday"
Your flight into the San Jose airport was just the way you liked it: uneventful. There was no turbulence, the weather was clear and sunny, and since you and your friends booked first class, there was plenty of room to stretch out and relax. You and your co-stars just started summer hiatus after filming the eleventh season of Supernatural, on which you played a hunter who happened to be taken in by the Winchester brothers, and Jared and Jensen had convinced you to join them for a long weekend at a private villa in one of Costa Rica’s premier resorts. You had been dreaming of going there for years, so you jumped at their offer. The three of you had gotten pretty close over the years on set, so being the only woman in the group didn’t faze you in the least. They were always perfect gentlemen, and that continued to be evident after you landed and they hoisted your bags into the back of the jeep that would transport you through the jungle towards your resort.
You sat between the two of them on the back of the jeep, your petite frame seemingly enveloped by their much larger statures, as the vehicle bumped up and down the winding, unpaved road towards your destination. It was humid in the jungle, and by the time you arrived at your resort, the three of you were drenched in sweat. As soon as you checked-in and got the keys to your villa, you planned on hitting the private plunge pool that was just off the living area to cool down.
When Jared unlocked the door, the three of you entered into the wide open common space. You immediately kicked off your sandals and walked barefoot along the cool, beige tiles that covered every inch of floor in the two-story accommodation. There was a large custom kitchen to your left and a sunken area in the center of the room with a large sectional sofa and entertainment center. Dark Mahogany stairs led up to the right and onto the long expansive upstairs hall, which was open to the floor below. There were two bedrooms up there, one with a king-sized bed and another with two queens. The boys very graciously let you have the king room, since you were the only girl there and you would probably want some privacy. Those two idiots were used to sharing digs up in Vancouver, so sharing a room didn’t bother them at all.
After setting your suitcase down on the bed, you pushed the door closed enough that the guys wouldn’t be able to see in, and quickly changed into the new red bikini you bought for the trip. Grabbing a towel from the fully stocked linen closet in your adjoining bathroom, you snatched a hair clip out of your toiletry bag and twisted your long hair up into a loose, sloppy up-do if for nothing more than to get it off the back of your neck. The air-conditioning felt great, but you couldn’t wait to get into that pool downstairs.
With your bare feet you padded back down the stairs and headed straight for the opposite side of the room, where a large, accordion glass window slid open to allow access to the small patio and pool just outside. The water was perfectly clear and cool, and the view from where you sat high up on the mountain was incredible. You stepped into the crisp water and leaned your arms up on the infinity edge to gaze out over the horizon. You could see the pristine, white sand beach through the tree line and you took a deep, relaxing breath. This was definitely the kind of vacation you needed right now.
“Seriously? How’d you get down here so fast?” Jensen’s rich, deep voice came from behind you.
You turned around to face him, standing there in his swim trunks.
“I was so overheated from that ride. I couldn’t wait to get cooled off.”
Jensen smiled at you as he set his own towel down on one of the lounge chairs. “I’m sorry,” he apologized as he sat at the edge of the pool and slid himself into the cool water, “I forgot the effect I had on you.” He winked as he leaned back against the wall opposite you.
“You’re so full of it,” you retorted, swatting a wave of water at him.
“Hey! Hey!” he protested with faux-anger, “Now you’re gonna get it.” Jensen pushed off the side of the pool to close the short gap between you, grabbing you by the waist.
“You promise?” you said, continuing your playful taunting.
Jensen’s mock-anger turned into that goofy, playful you’re-turning-me-on-now expression he usually reserves for the fans at conventions, or for that matter Misha when he is riling up the Destiel-shippers. “You know I’m always game for a little Y/N time.” He pulled you up against him and attacked your neck with kisses.
“J, stop,” you giggled as you tried wriggling out of his grasp, “Jared might see.”
He kept moving his lips across your skin, making his way across your shoulder. “So?”
You sighed, knowing that you had to finally make a confession that you should have made ages ago. “Seriously, J, stop,” you repeated gently.
Jensen pulled himself away to look you in the eye. “What’s the matter, sweetheart?” he asked sincerely.
Taking a deep breath, you placed your hands on his shoulders and let the truth finally come out. “You and I have been fooling around for awhile, but we agreed it wasn’t exclusive.” Jensen nodded in agreement, and amused smile on his face. You continued, “Well, I may have also had something casual going with Jared too.” You blushed and tried to look anywhere but in his eyes. There was no reason you should have felt guilty. It wasn’t like you were seriously dating either one, but it would be a lie to say that some feelings hadn’t developed between you and your two lovers. Just because no one admitted them aloud, didn’t mean they weren’t there, and you were afraid that even though it was made clear by all parties that what was transpiring between you was nothing more than a friends-with-benefits situation, you still didn’t want to hurt anyone.
Jensen shrugged, “Okay, I don’t care.” He went back to kissing your neck again.
“Seriously?” you asked, pulling away again to look at him, just to make sure he was telling the truth.
He smiled and tucked a stray hair back behind your ear, “We never said we couldn’t be with other people. I can’t exactly get mad at you for that.”
You smiled back at him. “Good, cause I would hate to think that you were mad or upset. I know he’s your best friend and I wouldn’t want to come between you.”
“Now, can we stop worrying and get back to business?” he asked hopefully.
“No!” you replied, “I don’t want Jared to walk out here and see us! I haven’t told him about you and me yet”
He pulled you close to him again, “Don’t worry about it. He went down to the market to pick up some booze for later. He’ll be a minute.” His lips were on yours before you could protest again, and if Jared had stepped out for a bit, then you certainly wouldn’t mind kissing J in the meantime. He worked miracles with his tongue. Pulling away from your lips he glanced down into the clear water below. “Is this new?” he asked motioning to your little red bikini.
You nodded with a smile. “Do you like it?” you asked.
“I love it!” he admitted brashly, “but I love what’s underneath it more.”
It was as if he had heard your thoughts just a moment ago, and in a blink of an eye, you were hoisted up onto the edge of the pool and Jensen had wedged his shoulders in between your thighs, spreading your legs open, his face in line with your bikini bottom. With a quick glance up at you and a smirk on his face, his fingers tugged at the elastic of your suit, pulling the fabric aside and exposing your lady bits. His lips suctioned themselves to your clitoris and you rolled your head back as you ran your hand through his hair, holding on to the back of his head as his expert tongue flicked over your pleasure button. Letting yourself get caught up in the feeling, you let out soft moans as Jensen worked up your arousal. His tongue dipped into your opening, swirling around your walls before laving at your clit again. Your heart began thumping quicker in your chest and you pushed his face closer, eliciting a guttural growl from Jensen. Taking your cue, and as always making sure you were fully satisfied, Jensen probed at your entrance with his finger and then slid two digits inside, pumping them in and out rhythmically in time with the ministrations of his tongue. Your fingers gripped and tugged at his hair, and Jensen buried his face further into your slick folds, his fingers pumping faster and faster while he sucked your clit between his full lips. It was as if he would gladly suffocate himself in your sex rather than stop for air, rather than halt your pleasure, and it didn’t take him long to bring you to the precipice before he crooked his fingers to press deeply into your g-spot sending you screaming off the cliff. “God yes, J, fuck!”
“Wow! It didn’t take you two very long did it?”
You gasped and spun your head around, looking up the long, lean frame of you other lover. “Jared! I can explain all this,” you began, frantically righting your bikini bottom as Jensen backed away to slide under the water, washing your orgasm from his chin. You stood up, legs wobbling a bit before you could fully face Jared. “I’m sorry I didn’t tell you, but we agreed we were just a casual thing, and I kind of, maybe, definitely had a casual thing with Jensen too.” Your forehead wrinkled with worry and you stood there as Jared looked down at you for what felt like an unbearably long time.
“I know,” he said before stripping his shirt off and kicking off his shoes. He stepped down into the water, leaving you dumbfounded on the deck above him and Jensen.
Turning and looking down at the two of them, you finally gathered your thoughts and spoke. “Wait, you knew?”
“Of course I knew, he’s my best friend. We tell each other everything,” Jared said nonchalantly.
It took you another minute to register the obvious, but you still had to ask anyway, “So, wait, Jensen, did you know about him too?” A broad smile graced his too beautiful face. “And you just sat there and let me get all worried while I made my big confession?”
“Yeah, it was cute! I don’t know why you thought we would mind, but it was adorable watching you squirm,” Jensen replied.
You huffed, “You’re both jerks!”
“Aww, come on, you don’t mean that,” Jensen said.
“Yeah, you know you love us!” Jared chimed in.
You cocked to the side, hand firmly on your hip like a petulant child. “Nope, not anymore.”
Jared swam over, or rather stepped across the tiny pool, and grabbed your ankle, giving a quick tug.
“Jared, don’t!” you yelped, but it was too late, you went careening into the water, Jared deftly catching you so you didn’t hurt yourself. He put you down gently so you were standing between him and Jensen, and pulled you into his chest, your back up against his hard, rippling muscles. His long arms encircled you and you let yourself relax into him. “You guys really aren’t mad at me?” You needed to reassure yourself.
“No,” they both responded in stereo.
“We know how to share,” Jensen added.
After you cooled down and relaxed poolside all afternoon, the three of you got showered and ready for dinner. There was an amazing restaurant on the property that overlooked the ocean, and you timed your arrival so you could watch the sunset over the horizon as you dined on locally-sourced traditional dishes. The hostess sat you in a semi-circular booth facing the open patio, and Jensen stepped aside to let you slide into the middle, between himself and Jared. When your waiter arrived, he handed you all menus and then stopped and stared awkwardly. “Oh my God,” he said in a whisper, trying not to attract attention, “it’s Sam and Dean, and...and Rachel! Oh dios mio! I love your show! Lo siento, I know this is not professional, but estoy tan emocionado!”
“It’s okay, you don’t have to be sorry,” you said, “we’re all family!”
“This is so amazing! You are so much more beautiful in person!” the waiter went on, “Oh, not that you are not beautiful on TV,” he chastised himself under his breath, “Soy un idiota!”
You laughed and reached across the table to pat his hand, “Thank you, that’s so sweet!”
He took a moment to compose himself, apologizing profusely, and then handed Jared the wine list. Jared didn’t even need to look. You were all celebrating the end of a successful season, so he had planned to order a bottle of champagne for the table. You also placed an order for an appetizer of the house fried Yucca and after he poured you all glasses of ice cold water, the waiter shuffled off to the less glamorous reality of his job.
“He’s right about one thing,” Jared leaned in to say, “You are looking especially beautiful tonight.”
You leaned into his shoulder playfully, “Thank you! You two clean up pretty well yourselves.”
The three of you had dressed up a little for your evening out. Jensen and Jared were both wearing sport coats and you had shimmied into a strappy little cocktail dress that perfectly accentuated your curves in all the right places.
As the meal went on, you all had knocked back a few glasses of champagne and right before you ordered dessert, the sun sank down behind the everlasting ocean. “That was so beautiful,” you announced, your words slightly slurred from the bubbly you consumed too quickly. You weren’t exactly drunk, but you did have a strong buzz.
“It was,” Jensen agreed, “but, compared to you? Eh.”
“Stop,” you playfully smacked his arm, “no, but seriously, keep telling me how beautiful I am.”
Jensen simply winked at you, but a warm hand was suddenly massaging your left knee. Jared’s hot breath hit your ear, “You are the most beautiful women I’ve ever had the pleasure of pleasuring.” He nipped at your earlobe, and you turned to look at him, your face flushed either from his compliment, his hand that was slowly making its way up your inner thigh, or possible the champagne. Or very possibly all three. He was smiling his brilliant smile and you leaned in to him, nose to nose with a giggle.
“All right you two, cut it out,” Jensen chided, “we’re in public.”
Jared ignored him and when his fingers finally reached their destination you sucked in a quick breath and sat up straight. You didn’t really think he would actually go there!
“Are you not wearing underwear?” Jared asked in surprise, and a little too loudly.
Jensen closed his eyes, his lips in a thin tight line, and shook his head. “Dude,” he said, “Maybe you shouldn’t draw so much attention to yourselves right now.”
Just then the waiter came up to the table to get your dessert order. Jensen quickly ordered the chocolate cake for all three of you, getting louder with every word to try and cover up the fact that you were trying to hold back the mewling you wanted to let loose because Jared now had three fingers working inside you. The waiter smiled awkwardly, but didn’t seem to understand what was going on, and he finally walked away. You let out a quiet whimper and then a throaty moan as Jared kept up his illicit actions. “Ow,” Jared jumped a little, “What’d you kick me for?”
“Cause you guys are gonna end up in the tabloids if you keep that up! Wait until we get back to the suite,” Jensen answered in a stern whisper.
“Fine,” Jared grumped, slowly removing his fingers from your snatch, bringing them to his lips and sucking your juices off of them while he wiggled his eyebrows.
“Oh my God,” Jensen mumbled to himself, embarrassed.
You looked over at him, your face expressing a coy apology. “Sorry, J! You’re right we shouldn’t do that here.”
The three of you had your dessert and Jared and Jensen split the check. They never let you pay when you all went out, and while you appreciated the gesture, you wished they would let you pick up the tab once in a while. Once you were all paid up you headed back to the suite and you all got into something more comfortable. You were wearing a simple white tank over your black bra, and a pair of cutoff shorts, the boys had thrown on some shorts and tee shirts. No one was planning on leaving the suite anymore that night, so before you knew it you were all doing shots and cranking up your playlists, goofing off and getting drunk.
The night was starting to wind down, Jared was pouring himself another drink at the bar and Jensen was slouched down on the sectional sofa watching you dance to the classic rock that was currently playing. Aerosmith’s “Rag Doll” came on and you sloshed a little of your whiskey on the carpet when you jumped up excitedly and announced that you loved that song! “Whoopsie!” you sing-songed, “Here, hold my drink. This is my stripper song!”
Jensen took the glass from your hand and downed it. “Knock yourself out, kiddo. I’d love to see it.”
You started to sway your hips to the beat, and playfully walked toward him on the couch. While you danced you ran your hands up and down your body, turning around and shaking your booty in his direction, which made him laugh. You even did your best Tawny Kitaen impression, swinging your hair around, all shame left behind with the alcohol you had been consuming all night. Jensen was eating all of it up, his mouth turning up at the corners as you moved closer and closer to him. You shimmied your breasts in his face, and you wound up straddling him, grinding your hips down onto his now hardening bulge. His hands grabbed onto your hips, but you pushed them off, wagging your finger in front of his face. “No sex in the champagne room,” you slurred.
Jensen let out a hearty laugh, “We’re not even drinking champagne anymore, sweetheart.”
“Just let me work my thing,” you insisted.
“Work away,” he replied amused.
While you continued giving him a lap dance, you didn’t see Jared step down into the sunken living room and stand behind you, watching the show as well. “How come I don’t get a lap dance?” he pouted.
You turned your head around to look at him, his puppy dog eyes tugging on your heartstrings. Those puppy dog eyes always got you. In a feat of drunken athleticism, you bent backwards, splaying yourself across Jensen’s lap and somehow managed to do a back walkover to come to a standing position with your back up against Jared’s strong frame. Although, you’re pretty sure Jensen had a hold of your hips when you managed to pull off your floor routine, and Jared seemed to have moved forward to make sure you didn’t fall when you made it over, but still you thought it was impressive. When you regained your composure you swayed your ass against Jared, giving him a little lap dance of his own.
As you ground up against him he snaked his arms around your waist from behind and bent down to kiss your neck. You continued to wiggle in his grasp, and then his hands found the bottom hem of your tank top and it was up and over your head and tossed aside. You turned to him, stood on you tippy-toes and placed a wet, sloppy kiss on his lips. He smiled and his deft fingers found the button on your jean shorts, popping it undone and then sliding the zipper down. In another second you were kicking them off and resuming your sexy dance. Jensen had undone his own shorts and was stroking himself while he watched you grind up against his best friend.
“You want this?” he asked, when you couldn’t stop staring.
Your tongue involuntarily ran across your bottom lip as you nodded.
Jensen smiled up at you, motioning with his finger. “Then come get it.”
Jared let you go and you made your way back to Jensen, who was now standing up with his shorts and boxer briefs around his ankles.
“Get down on your knees for me, sweetheart,” Jensen commanded with a breathy, gravelly voice.
You did as you were told, sinking to your knees and grabbing ahold of his erection at the base while you swirled your tongue around the tip.
Jensen sucked in air between his teeth. “That’s it, baby, put your mouth on it and let me see those pretty eyes of yours.”
Taking his length into your mouth slowly, you turned your eyes up at him and batted your lashes, making him groan in appreciation. You moved your mouth along his shaft, back and forth, while your hand tugged at the base in rhythm with your movements. His hands gathered up your hair, pulling it away from your face so he could see you better as you sucked his dick. “God, Y/N, you are so fucking good at that,” he praised. Jensen watched you as you continued to bob your head back and forth, drawing soft moans from him. “I think you’re making Jared jealous, sweetheart. Why don’t you let him see what he’s missing?”
You pulled off Jensen with a pop and turned your head to see Jared’s long, stiff cock waiting for you to give it some attention. Jared smiled down at you before you wrapped your lips around him too, and he thrust his hips gently in time with each of your movements. As you were working Jared up, Jensen’s fingers were working on unhooking your bra, and when it snapped free, he slid it off your shoulders and down your arms, exposing your breasts.
“That’s it baby girl,” Jensen goaded as his warm hands massaged your tits from behind you, “Can you take him deeper?”
Not one to back down from a challenge, and wanting to please both your lovers, you relaxed your jaw a bit and pushed further down on Jared’s shaft. Jared grunted and grabbed a handful of your hair, tugging gently and then pushing you even further down onto him. “C’mon, Y/N, take it all in,” he coached. His hips thrust up slowly to meet your face, and you tried your best to get him all in, but gagged on his length. Jared pulled out to let you catch your breath, spittle hanging in long strands from your mouth to his dick. “Good girl,” he said, before using your hair to turn you back towards his friend.
Jensen had kicked off his pants and underwear by now, and was just standing there in his white tee-shirt, fingers wrapped tightly around his throbbing member. He inserted himself into your mouth again, and took your hair from Jared’s grasp, taking back the control. Jensen pushed and pulled you back and forth on him, fucking your face faster and deeper than before. “Reach behind you and stroke Jared’s cock, sweetheart,” he said in between grunts as you sucked him harder.
You did as he instructed and Jared guided your hand to his length, helping you pump him until you found the rhythm on your own. Jared reached down to slap your tits, causing you to jump a little at the sensation, and making you tighten around Jensen’s cock, which in turn made him moan a little louder.
“Fuck, Y/N, you’re gonna make me cum if you keep that up,” Jensen said, his voiced strained with concentration.
“Give him a break then,” Jared said, “come back over here.”
Jensen pulled out of your mouth and you turned around to replace his cock with Jared’s again, but you reached behind you to stroke Jensen while you were at it. You couldn’t keep that up for long though, because Jared had your head cradled in both his hands and was fucking into your mouth. Bracing your hands on his legs, you breathed as best as you could through your nose so you could take him in as far as possible, and it wasn’t long before he had to slow his movements to avoid finishing early.
“You ready?” Jensen asked him, and when he nodded, J pulled you off of him and held you beneath them as they jerked themselves until both let out a guttural growl and thick white ropes of cum landed heavy on your tits and face.
All of you were breathing heavy from your exertions, and time seemed to stop for a minute while everyone caught their breaths. You were trying to stay as still as possible, so their semen wouldn’t drip onto the area rug, and you licked away any salty spots that were on your lips. Jared pulled his shirt off and heaved you over his shoulder, shuffling with his pants around his ankles as he tried to carry you upstairs. You squealed in his arms, head hanging behind him and unable to see where he was going.
“Dude, you’re gonna drop her,” Jensen called after him, “Kick off your pants, man!”
Jared stopped for a second, “I can’t, their stuck on my shoes!”
“Jesus, give her to me and get yourself together,” Jensen offered. He too disposed of his shirt so as to not get any of the cum that was still coating your chest and stomach on it, and Jared handed you over. Jensen’s arms supported you under the back of your knees and threaded under your arms, carrying you up the stairs while Jared bumbled behind you.
“Where are you taking me?” you playfully interrogated him.
“Gotta get you cleaned up,” Jensen responded, “You know we aren’t done with you yet, right?”
You giggled again. Geez, these two made you revert to a teenage girl!
When you reached the top of the stairs, Jensen carried you through your bedroom and into the attached bathroom. He deposited you on the vanity while he got the water running in the walk-in shower. Once it was sufficiently steamy, Jensen picked you up again, this time wrapping your legs around his waist so you could straddle him, and walked you both into the hot stream. Jared, who had finally shed the rest of his clothing, walked in behind you and shut the glass door. You found yourself between the two of them again, and they made quick work of cleaning their mess off of you. Jensen used your loofah to suds you up, while Jared lathered shampoo in your hair. They each took a moment to rinse themselves off as well, and before you knew it you were being slung back over Jared’s naked shoulder and tossed onto your bed.
The boys crawled up on either side of you and snuggled up to your frame. You were facing Jared, Jensen behind you, and they were both leaving tender kisses on your still damp skin. Jared’s fingertips whisped lightly along your collarbone as his mouth explored yours, and you could feel Jensen’s hand massaging your hip and cupping your bare ass while he nibbled the tender skin at the nape of your neck. His warm breath caught your ear as he whispered throatily, “Do you like being our dirty girl?”
“Yesss,” you hissed out, their warm mouths hitting all the right erogenous zones. You were sure that if you reached down between your legs you would be a slippery mess again already. It wasn’t long before Jared’s fingers confirmed that thought. His hand ran down your breast, stopping to tweak your nipple and making it stiffen, then smoothed down your stomach and abdomen to rest atop your soft mound. Two fingers found their way inside you, slowly stretching your walls, while his thumb rubbed languid circles around your nub. You sighed and exhaled a deep, satisfied breath.
“Does that feel good?” Jared checked, earning another deep breath and a nod from you to continue. His mouth found its way to your breasts, and he slowly and sensuously took his time to stimulate each of your nipples with his lips and tongue as he continued to finger your pussy.
Jensen, meanwhile, was taking his time lovingly massaging your back and shoulders, leaving soft, chaste kisses between your shoulder blades and along the rise of your hip. One of his fingers joined Jared’s for a second, slicking his digit up with your excretions before sliding through your crack and wetting the little starburst between your cheeks. He pressed down lightly and rubbed concentric circles around your rim, shooting an electric jolt up your spine. You heard him hum with satisfaction that he was adding to your pleasure, and your body tightened again when you felt his tongue between your cheeks, lapping at your back door.
Jared broke his contact with your tits to soothe you. “Relax, sweetie. We’re gonna take care of you.”
Jensen’s tongue left your rim as he shifted himself to his knees on the mattress. “Put that sweet ass in the air for me,” he ordered.
You complied, getting up on all fours and shifting your ass backward towards him.
“That’s a girl,” he cooed, rewarding you with a playful smack. “Let’s get her good and ready for us, Jare.”
The two of them worked in tandem, focusing solely on getting you off. Jared turned upside down in the bed, lying beneath you. When his face was directly below your cunt, Jensen slowly pressed down on your lower back to seat you closer to Jared’s face. He watched as his friend licked and sucked your pussy and smiled as you moaned louder and louder. But he wasn’t going to let Jared have all the fun. His mouth returned to your ass, and you felt his tongue dip into your tight ring. The sensation of both of their tongues working against you was unreal, and you bucked and writhed against them as they assaulted your most sensitive areas. It didn’t take long for the pressure to build in your gut, your moaning becoming louder and higher pitched as the dam broke and your orgasm flooded over Jared’s face. Jared licked up every last drop, bathing your pussy with his tongue, while Jensen continued to flick his own tongue faster and faster over your rim, coaxing out a second smaller orgasm just seconds after your first one.
“Y/N, you are so damn hot,” Jensen said, lifting you off of Jared and sliding you onto your back. He kissed you urgently, pressing you down into the pillow while his tongue navigated your mouth.
Large hands grabbed you under your knees and tugged you down the mattress, hoisting your legs up so your ankles were resting on Jared’s shoulders. He was threading his long, hard dick through your folds, lubing himself up on your juices. “I can’t wait anymore, Y/N. I have to fuck you,” he said and immediately he shoved himself into you down to the hilt. The way he filled you up was a shock to your system every time you were together, but there was no denying that it felt incredible. Jared pulled out of you slowly, only to forcefully penetrate you again, and a small squeal of delight left your lips with each thrust. Once your pussy conformed to his length and girth, Jared found his rhythm, rocking into you at a steady pace. Closing your eyes and throwing your head back you let yourself revel in the sensation.
You were so distracted by Jared’s movement that you didn’t even notice Jensen straddling your waist, until he leaned down and whispered into your ear. “I’m gonna try something new with you, okay sweetheart?”
Your eyes opened and looked up into his beautiful green orbs. He was waiting for your approval, so you nodded your head and smiled. Jensen smiled back, kissing your forehead tenderly, and then righted himself on top of you. He grabbed your hands and drew them up to either side of your breasts, pressing them firmly with his own strong hands to squeeze them together. “Hold them just like that for me,” he instructed and then rutted his cock in between the tight space that was created. He held himself there, paying close attention to the rhythm Jared had set, and then thrusted in time with each of his friends movements.
Jared grabbed your hips, his fingers digging into your flesh, and lifted your ass off the bed, scooching his pelvis in closer to you and fucking you hard and fast as he grunted and groaned. Jensen tried his best to keep time, but his dick kept slipping out from between your tits. He repositioned himself so his strong arms were holding himself up on either side of your face, and you watched the flex of his muscles as he pressed his cock into your chest and rubbed himself further against the insides of your breasts.
The friction both in between your legs and below your neck was making you extremely hot, and you found yourself spitting out dirty commands to your lovers. “Fuck my pussy harder, Jared!” He immediately complied. “God, yes, Jensen I want you to cum in my mouth!” As the boys kept up their frantic pace, all you could hear was a series of growls, screams, and expletives echoing through the room.
A few more frenzied pounds to your sex and Jared was filling you up with his seed, your walls contracting around him as your climax struck. His cock twitched inside you and stayed there as it softened while Jensen continued to slide between your tits, until he too couldn’t take it anymore. “Open your mouth, Y/N! I’m gonna cum,” he grunted, and you tilted your chin down to take his tip in and suctioned around his engorged shaft. With a rumbling growl he let himself go; his warm milk hitting the back of your throat. When he was spent, he pulled himself from your mouth with a shudder at the cool air hitting his sensitive skin, and he rolled over onto his back next to you. Jared did the same, and for a moment all three of you laid there silent staring up at the ceiling.
Jared rolled over onto his side and rubbed his palm across your belly. “You’re fucking amazing, you know that Y/N?”
You smiled up at him.
“Oh she knows she’s a little vixen,” Jensen answered for you, rolling in towards you as well and placing a kiss on your cheek.
Both of them wrapped their arms around your waist and laid their heads on each of your shoulders. You brought your hands up to cradle their faces and kissed their foreheads before settling in and falling asleep.
Chapter 2: "Saturday"
Pulling in a deep, sharp breath, you rolled over to your left and found your face smooshed up against Jensen’s bare chest. His arm was draped loosely around your shoulders, and his skin was warm. Your eyes fluttered open and you craned your neck upwards to be greeted by a lazy smile.
“Hey beautiful,” he said, his voice husky from sleep.
“Hi handsome,” you purred back, making his cheeks flush pink and wresting a shy smile on his face. “Where’s Jare?”
“He’s getting breakfast started downstairs,” he answered and pulled you in closer, placing a sweet kiss on the tip of your nose. “How are you feeling this morning?”
“Well rested,” you replied, “I slept like a drunk baby.”
Jensen’s musical laugh brought a smile to your face. Pushing yourself up on your elbow, you climbed up his chest so you could kiss him long and deep. He groaned in approval and tangled his hands into your hair, holding you close to him and savoring your kiss. When you broke away, you let your fingers trace the peaks and valleys of his muscular chest and laid your head down on his shoulder again. “I love waking up with you,” you admitted.
“Yeah, I know you do,” Jensen teased, and you gave him a playful slap, causing him to laugh again. “Ow, that kinda hurt,” he whined.
You rubbed his chest in apology, “I’m sorry, baby. Want me to make you feel better?”
“Always,” he responded. His eyes darkened.
Slowly, you snaked your leg over his waist and straddled him, looking down at his gorgeous face. His breath hitched slightly in anticipation of whatever it was that you were about to do to him, and you were pretty sure that he’d be blushing right about now if he could hear the dirty thoughts that were running through your mind at that moment. You could feel him stiffen beneath you, and you reacted by rolling your hips down onto him. He closed his eyes, reveling in the feeling while you slowly slipped him inside of you. You couldn’t help but moan in appreciation of the way he felt. It was different from the way Jared had felt. Jensen wasn’t quite as big as his friend, but he was girthy and he still fit snugly. In fact, he fit perfectly, like his cock was made specifically for you.
You rose up along him and he sucked in a breath, his hands reaching out to hold onto your hips to help guide you up and down. As you rode him, you brought your hands up to clutch at your breasts, pinching and tugging at your nipples and sending thrills down to your core. You could hear his breathing become labored, and he was muttering something under his breath, but you couldn’t make out what it was. Not letting it deter you from you your task, you continued to bounce atop of him, angling forward when you took his full length in so that your clit rubbed against his pelvic bone. Little whimpers fell from your lips as that hot, tense coil started to build up inside you.
His heavy-lidded eyes looked up at you, a sly smirk betraying the naughty thoughts that were floating around his mind as he watched you ride him. “Lean back for me so I can see everything,” he encouraged. He let out a low whistle when you complied and shifted his hand down to massage your sensitive bud. When you threw your head back with a heady groan, he increased the pressure and rubbed you faster, bucking up into you and giving you a break from the work. His fingers were pressed tightly together, and he was playing your clitoris like a DJ would scratch a record. The bundle of nerves were quickly becoming over-stimulated, and you tensed a bit, biting you lip hard to keep your focus on rocking along his length while he pleasured you. He noticed the strain on your face. “You okay there, sweetheart?”
Somehow through several short breaths you managed to respond, “Yes. It’s just…intense.”
“You need me to slow down?” he asked sweetly.
Suddenly there was a long pair of muscular arms around you. “She can take it,” Jared encouraged, “can’t you baby?”
You sucked in a deep breath and nodded in affirmation, thankful for the support of Jared’s chest behind you.
He held you close and leaned you back further into him so he could enjoy the view as well. “Rub her harder, J,” he commanded, and Jensen followed his friend’s directions.
It was as if Jensen was strumming out a particularly frenzied guitar solo, and the surge of electricity that was now pulsing through you caused your hips to falter. You just lay back into Jared and left Jensen’s cock sheathed all the way inside you. “Cum for me, sweetheart,” Jensen coaxed, but you didn’t need any encouragement. Your insides felt like they were about to explode, and you let out a great wail when your climax squirted out all over Jensen’s torso. “Fuuuckkk!” He strained as you clenched down on him like a vice grip, and he ended up unloading his own excitement into your throbbing sex.
You laid there limply, thankful for Jared’s strong support, while you huffed out the end of your orgasm. When you finally caught your breath, you tried to pull yourself off of Jensen, but his fingers quickly pressed into your hipbones to keep you in place. “Don’t move yet,” he pleaded, “too sensitive right now.”
It took a few minutes, but with a nod, Jensen finally signaled Jared to help you off of him, and he looked down at himself with an amused chuckle. “Damn, girl! You made a mess that time.”
“Sorry,” you apologized as the blood rushed to pink your cheeks, “You did too, though.” A thick stream of white cum was slowly leaking from between your legs.
“Y’all are both filthy,” Jared teased with a smirk, “Go get cleaned up. Breakfast is ready.”
After the three of you finished breakfast you spent the day being tourists, and after a full six hours of ziplining through the jungle canopy, hiking to see spectacular views of a volcano, and horseback riding through the rainforest, you were more than ready to just kick back and relax with your two best friends. You cleaned yourselves up, which you seemed to be doing an awful lot on this trip, and walked down to the hotel bar for some chifrijo and several cold bottles of beer before talking a leisurely walk on the resort’s private beach. There were only a few other guests enjoying the palm-shaded sand, and it didn’t take you too long to find a nice secluded spot with enough lounge chairs for the three of you. You relaxed back into the chair between the boys and breathed in a healthy lungful of warm salt air.
“This is the life,” you said, knowing full well it was the most clichéd thing you could say at that moment. “I’ve been looking forward to relaxing all day.”
“Yeah, I gotta say it was kinda rough riding those horses earlier,” Jared complained, “I’m a little sore.”
You smirked, “Yeah, I’m a bit sore too.”
“That’s from riding us, sweetheart, not the horses,” Jensen said nonchalantly, his sunglasses shading the amusement in his eyes. “I didn’t think it was that bad. I feel fine.”
Jared tittered, “That’s because you’re bowlegged. You’re legs fit perfectly around the horse.”
“Heh heh heh, shuddup!” Jensen responded.
“You guys are idiots,” you cracked, stretching your arms up above your head and reaching your toes toward the bottom of the chair. “I could use a massage right about now.”
Jared sat up and spread his legs to fall over each edge of his chair, patting the cushion in front of him. “C’mere, I got you.”
You pulled down your sunglasses to peer over at him. “You serious? Cause you know I never turn down a massage.”
“Yeah, get over here!”
Popping up quicker than a corn kernel, you sat cross-legged on the chair between Jared’s legs and let out a contented moan when his fingers squeezed your shoulders. “Mmmmm…that feels good, Jare.”
“Will you two keep it down over there,” Jensen complained, “You do like to draw attention to yourselves don’t you?”
You moaned again as Jared dug into the muscle between your shoulder blades.
“Don’t be jealous, man,” Jared replied as he worked his thumbs in circles up and down your spine, eliciting more soft groans from you, “you got to have your hands all over her this morning and I didn’t complain.”
“We weren’t in public,” Jensen pointed out. There was a reason no one ever caught Jensen doing anything untoward in the gossip rags. He was very careful with himself when he was out and about, never letting fans or the paparazzi catch him in the act. Jared on the other hand had been photographed frolicking in the waves on their last beach vacation, resulting in shirtless photos being plastered all over the internet. “Before you know it, the rumors will be flying about you two having an affair.”
“We are having an affair,” Jared said matter-of-factly, “We’re sleeping around behind your back!”
You and Jared both giggled at his joke. “Anyway, what are you ashamed of me?” you asked, “Would you be embarrassed if the pap found us out?”
Jensen turned to you and pulled off his shades, “Of course not! You don’t think that do you?” He didn’t let you answer. “I just like my private life private is all.”
You smiled at him sweetly, “I know, I’m teasing you.”
“Let’s save the teasing for later, sweetheart,” he replied, putting his sunglasses back on and lying back in his chair again.
Jared continued rubbing your back and shoulders for a while before guiding you to lie back onto him and relax. You lay there in his arms until the sun started to set, listening to the soft snoring coming from two chairs over. Not a soul had wandered by your little spot to disturb the three of you, and you were enjoying the quiet moment with your two lovers. You felt Jared’s lips brush against your earlobe and his warm breath graveled low into your ear.
“You feel better now, baby?”
Craning your neck up, you side-eyed him and responded, “Mmm hmm. I feel great! Totally relaxed.”
He kissed behind your ear, then at the nape of your neck, then your bare shoulder. “Wanna feel even better?” he asked.
A thrill went through you. “What do you have in mind?”
Jared continued to kiss your neck from behind as his strong hands found their way to your breasts, kneading them through your cover up. You arched your back, leaning into his hands as he tweaked your nipples through the double layers of fabric. They stood up when he released them, the way egg whites would stiffen and peak when whipping up a meringue. You only wished that Jared would put his mouth on them now and get a taste. But you were out in the open, and although the area you three had chosen was relatively secluded, there was still a possibility of a random stranger wandering by, so whatever Jared had in mind you would have to be as inconspicuous as possible. His hands continued to knead your breasts and he shifted his pelvis forward so you could feel the way your body was making his react.
“You feel that baby girl? God, you make me so horny all the time.” He breathed in your ear.
An involuntary squeak escaped your lips, and you could feel him smile against your skin.
“Want some help with that?” you offered, and he hummed into your ear again, sending another chill down your spine.
Shifting slightly, you reached a hand around your back a gripped his hard-on through his swim trunks, stroking him through the fabric. He hummed again, and let one of his own hands wander down your body and up underneath your cover-up to massage your cunt through the nylon of your bikini bottom. Your breath hitched at his touch, his warm hand stimulating you gently.
“Think I can make you cum like this?” he purred, as you leaned back further into his chest to rest the back of your head against the crook of his neck.
“I’m sure you’ll find a way,” you replied. Both of you worked to please the other; hands massaging and stroking the your most sensitive areas.
Jared breathed deep when he could feel your arousal soak through your bikini bottoms, and he pressed deeper into your mound, using the slick to slide the fabric over your clit in concentric circles. “I love how wet you get,” he cooed as his fingers worked their magic. The feeling wasn’t overwhelming like your exertions from earlier that morning, but they were still as tantalizing; more sensual than overtly sexual. A deep moan escaped your lips, and you wanted to give him the same amount of pleasure he was giving you. Since you were sitting in front of him, no one would notice if you slid his long cock out from the elastic of his waistband, and you wanted to feel his smooth skin against yours. Arching your lower back up once again, you wrested his shaft out from his trunks and thumbed the tip. You could feel him twitch behind you, which brought a smile to your lips. “You like that huh?” You asked, already knowing the answer.
“You know I do,” he responded, increasing the speed at which he was toying with your sensitive bud. Your bikini bottoms were soaked now, as if you had just taken a dive in the ocean, and it was easier for him to manipulate your pleasure zone.
The angle at which you were pleasuring him, however, was difficult and you needed some help to get him off. You weren’t going to leave him hanging, because you were sure that he was going to send you over the edge any minute. For a brief second, you brought your arm back around and slid your hand under the elastic of your bottom, palming your pussy and dipping your fingers into your entrance to slick up your hand, before reaching back around to slide your juices up and down Jared’s member. You felt him smile against your ear again before he whispered to you, “Fuck, yes baby, just like that.”
It didn’t take him much longer to bring you to the precipice, and before you knew it, the rubber band in your stomach snapped and a full-bodied moan made its way past your lips. Jared used his other hand to cover your mouth, stifling it just enough that he was sure it wouldn’t wake Jensen, who was still sleeping just five feet away in his lounge chair. Once you came down from your high, you put all your energy into stroking Jared’s cock, and you heard him suck air through his teeth just before you felt his warm ejaculate on your back. His toes curled until he was emptied out, and then he pulled you back into him, holding you close and not worrying about the mess that was stuck between you.
For a moment, the two of you just lay there, letting your breathing return to normal and enjoying the warmth of each other’s bodies against your own. “That was nice,” you muttered, not even sure if he had heard you, it was so quiet. He wrapped his arms around you and gave a little squeeze.
“I’m hungry now,” he announced, “are you hungry?”
You chuckled. He was always hungry. “I could eat! We only had that little snack this afternoon.”
“Let’s wake J up and head back so we can get some dinner. Whatta ya say?” he offered.
You nodded your head, and then swung your legs around to get up off the lounger. Grabbing your things and tossing them in your beach bag, you gently shook Jensen’s shoulder to wake him up. “Hey, sleepy head!” you called out, “We’re heading back to the room to get ready for dinner.”
Jensen wiped the sleep from his eyes, “How long was I out?”
“Long enough,” Jared quipped, a sly smile forming on his face as he pulled his t-shirt back over his head. The sweat that soaked through the white cotton masked the deeper saturation of his cum that had spread onto his belly when you leaned against him.
“Alright,” Jensen said, sitting up, “Let’s go.” He was oblivious to the snickering that was being passed between you and Jared.
You all gathered your stuff and walked off down the beach toward your villa. Jensen dragged behind a bit, and you and Jared couldn’t contain your laughter when he said, “Hey, Y/N! You have something on your back there.”
The three of you enjoyed a late meal at one of the resort’s restaurants and were now curled up on the couch watching a movie from the complimentary DVD collection that was in your villa. Even though you had all relaxed on the beach earlier, the days exertions and the big meal you just ate was making you all feel a bit lethargic. You were laying horizontally across the expanse of the sofa, with your head in Jensen’s lap and your feet in Jared’s. They were both languidly stroking you; Jensen’s fingertips twining through your hair while Jared used his thumbs to rub circles into the pads of your feet. It felt so good just to be lounging there with them, and you were glad that it was out in the open that you were benefitting with the both of them, even if you were the last one to be aware that everyone knew.
You blinked your eyes open, and realized that you must have fallen asleep. The movie credits were rolling, and Jensen was looking down at you and brushing the hair from your face. You sighed and pushed yourself up, realizing that Jared was no longer on the other end of the couch. “Where’d Jare go?” you asked as you rubbed sleep from your eyes. Jensen shifted his weight. He had been sitting in the same position for over an hour so as not to disturb you. “He pussied out and went to bed,” he answered, “Seems like neither of you could keep your eyes open.”
“That’s not fair,” you pointed out, “you took a nap earlier, we didn’t!”
He smirked at you, “Oh I heard all about your escapade on the beach.”
A blush crept up on your face.
“You two are gonna regret it when you get caught one day,” he warned.
Batting your eyelashes at him, you smiled, “That’s part of the fun, the thrill of getting caught!”
He rolled his eyes, “Well don’t say I didn’t warn you when you and Tommy Lee up there have your very own sex tape go viral on the internet.”
“Whatever, that would be one hot sex tape,” you joked.
Jensen let out a hearty laugh. “C’mere, you,” he said, pulling you back over to his lap.
You let him cradle you in his arms, and you let yourself fall into the deep green of his eyes. For a moment all you could hear was the breath ghosting between him and you, but then he dipped his head towards yours and captured your mouth with his own. His soft, full lips parted and his velvety tongue slid across your bottom lip requesting access. You opened your mouth to let him in, and as he kissed you deeply you found yourself being lowered onto your back. He broke the kiss, looking down into your eyes with a quirk of a smile dancing at the corner of his mouth. “You’re amazing. You know that right?” he said sincerely.
“Duh,” you snarked back, earning you another deep chuckle. You loved the way he laughed.
“Are you sassing me?” he asked with a playful lilt to his voice.
You looked up at him challengingly, “Maybe. What’s it to you?”
“Oh ho,” he exclaimed, his eyebrows raising, “you know you’ve been a bad girl today.” Seems like the challenge was accepted. “What do you think we should do about that?”
“How have I been bad,” you puzzled.
Jensen’s finger trailed down your nose and across your lips, forcing them apart and sinking a digit into your mouth. You hollowed your cheeks and suckled him, watching as his eyes rolled back into his head for a second with a soft groan. He answered your query when his eyes flew open again, “You and Jared had a play date without me today, didn’t even think to include me. That wasn’t very nice.” He tsked down at you and grabbed a handful of your hair to yank your head back roughly.
“I’m sorry,” you exhaled, “Are you going to punish me?”
His face lit up with amusement, but he quickly masked it again. “Do you want me to punish you?” He tugged your hair again.
Your heart sped up, thumping against your chest so hard you thought for sure he could hear it. “Yes, please!”
“Oh, so now you’re gonna beg huh?” he teased. He forced your head to the side and attacked your neck with his mouth, biting and licking his way from the base to just under your ear. You moaned at his touch, and he pulled back abruptly. “You aren’t supposed to get pleasure out of this. You’re being punished.”
“I’m sorry,” you said again, a little more breathless this time.
He narrowed his eyes at you, “You’re sorry what?”
You bit your lip to keep from smiling. “I’m sorry, Sir.”
“That’s a good girl,” he cooed, going right back down to your neck and sucking the delicate skin into his mouth, leaving a dark purple mark behind. “That’s so Jared knows who you really belong to.”
God it was so sexy when he played this game with you. Jensen was amazingly sweet and gentle with you most times, but when he really allowed himself to go there, to let his darker side loose, he could make you wet with just one touch. You were so lost in your thoughts that you were surprised when he yanked you upright again, splaying you face down across his lap. His hand tugged your sweats and panties down to your knees.
“I’m gonna spank this ass raw right now,” he declared, rubbing a hand across the two perfectly creamy globes that were exposed to him. “What’s your safe word?”
“Vanilla,” you replied with your least liked ice cream flavor. That’ll certainly put you off the mood. With your face aimed downward toward the couch cushion, you couldn’t see the smile that betrayed Jensen’s dominant mood.
His hand came down swiftly, but not too harshly the first time.
Two more in quick succession, and that time causing your cheeks to sting a bit.
“You good?” he asked, soothing his hand across your bottom again.
You nodded eagerly, enjoying the game.
A little yelp escaped your lips that time. That one definitely smarted.
“Fuck!” you shouted, biting your lip.
“Don’t tell me you’ve had enough already? That’s hardly a punishment!”
“No, sir, I don’t think I’ve learned my lesson yet,” you prodded.
This time his hand had left two stinging red marks, one on either cheek. You moaned with both pleasure and pain, but you were biting your tongue to hold back from using your safe word. You weren’t sure you could take another, and you didn’t want Jensen to feel bad for hurting you either. Before you needed to say it, Jensen’s hand smoothed over the burn and his fingers brushed down between your cheeks to find your sex. A little gasp escaped his lips and even you were surprised at how slick you were from his punishment.
“Seems like my bad girl likes being spanked,” he teased, and inserted his middle and index finger inside of you making your breath hitch, “Do you want some more?”
You shook your head, “No, sir. I just want you inside me.”
Jensen’s fingers pumped into you a little faster. “Like this?” he asked.
“No, I want your cock, sir,” you replied.
His fingers pulsed in and out of you faster now. “Are you going to be a good girl for me now?”
“Y-yes,” you stuttered in anxious anticipation.
“Are you sorry you left me out of the fun earlier?” He continued to prod. His fingers were curling inside you now, massaging your g-spot and making you even wetter than you were before.
“Yes, sir, please,” you begged. You couldn’t take it anymore. You wanted him to fuck you and fuck you hard.
In one swift motion, you found yourself being spun around so your face and arms were hanging off the couch. Jensen lowered you down slightly so you could reach the floor and stabilize yourself while he spread your legs wide on either side of his own. You could feel him moving the elastic of his pants down as he pulled his hardened length out of his boxer-briefs, then the tip of his cock moving through your folds to tease at your opening. “Is this what you want? You want this cock?”
“Please, Jensen,” you pleaded, dropping the sir. You didn’t want to play games anymore. You just wanted him inside you.
He shifted behind you, pulling your hips back so that he could sheathe himself inside you slowly. Both of you let out a throaty groan, and then he was bucking his hips forward and pulling you back simultaneously, rocking into you over and over again and building up a steady rhythm. Your breath quickened as he pounded into you, the blood rushing to your head as you hung there underneath him.
Jensen wrapped his arms around you and pulled you back up on the couch, flipping you around to face the backrest and moving to stand behind you. “Ass up, face down,” he ordered. You complied willingly. This was a much better angle, giving him better leverage from which to piston in and out of you. His pace quickened, and all you could hear between your moaning and the breathy cuss words spilling from his lips behind you was the slapping of his skin against yours. The knot in your belly was coiling around like a snake ready to strike, waiting for the right thrust to hit that g-spot the exact right way to release its venom.
“Fuck, Y/N, you need to cum soon or I’m gonna lose it,” Jensen grunted out behind you.
Somehow between sucking in shallow breaths you snarked back at him, “Then maybe you better fuck me harder Ackles.”
He wanted to chuckle, but instead he took the request seriously, letting go of your hips to grab your arms back behind you, effectively face-planting you into the cushions. He held onto your wrists tightly and pulled you back into him as he assaulted your cunt with thrust after thrust. The snake inside you was hissing and spitting until finally it released and you came hard, your walls gripping Jensen’s cock tighter, causing him to buck into you erratically. He quickly unsheathed himself and grabbed his now throbbing member in his fist, pumping fast as he emptied his load onto your ass, still red from his earlier punishment.
The two of you stayed stock still until your breathing returned to normal, and then he pulled his tee shirt over his head and used it to clean off your rear. The cotton was soft and soothing over your sensitive skin.
Jensen tossed the dirty shirt onto the floor and climbed back on the couch, lying on his side and pulling you down to lie in front of him. His arm wrapped around your waist, fingers tracing imaginary lines along your abdomen while he pressed soft kisses into the tops of your shoulders. You closed your eyes and let yourself sink blissfully into his gentle caress, the warmth of your body lulling you back to sleep. Somehow you knew that you would wake up in your bed the next morning, but you wouldn’t remember how you got there.
Chapter 3: "Sunday"
When you woke up you were alone in your bed. You knew Jensen would carry you up there if you fell asleep, and you were so tired after all the exertions of the previous day that you didn’t even notice. With a yawn, you stretched out, your muscles burned a little and your bottom was pleasantly sore. You smiled remembering your little game with Jensen.
After taking a shower you made your way downstairs to find your two boys eating breakfast at the small dining table in the kitchen. There were only small remnants of scrambled eggs on a plate in the center, and Jared was putting the last piece of bacon in his mouth when he looked up at you. “Geez, thanks for saving some for me,” you half teased, half griped.
Jensen looked up from his phone, “Oh, sweetheart, you know I wouldn’t let him eat all the food. I saved you a plate. It’s in the microwave.”
You smiled. “Thanks, babe,” you aimed your finger guns at him with a wink and he huffed a laugh before going back to whatever he was immersed in on his phone.
When you all finished up breakfast you spent some more time on the beach, lazing about and getting a good tan to start your hiatus. It was your last full day here. The next day you would be dealing with airport security and flying back to the states, so you just wanted to relax and enjoy yourselves today. You were a big fan of dolphins, and the boys had promised to take you snorkeling before you left so you could see one up close, so after lunch you met up with your dive instructor and got suited up to view the underwater wildlife. There were plenty of exotic-looking fish, sea horses, eels and even a sea turtle, but you were almost out of time and hadn’t seen a single dolphin. While you still had fun, you couldn’t help but be a little disappointed. Just as you were about to give up, Jared spotted a pod of dolphins in the distance and pointed them out. You swam a bit closer, and one curious little guy got within arms-length. It totally made your day!
After your underwater adventure, you all decided to just head back to the villa and relax the rest of the day. You wanted to get your stuff repacked for your trip home, so you headed up to your room to get a jump start, leaving out an outfit for the next day and necessary toiletries. Then you went to see what J-squared were doing. You looked down over the balcony, but neither of them were downstairs and you could see through the window that they weren’t in the pool either. Making your way down the hall, you knocked lightly on the door to their room and pushed it open gently to peek inside. Jensen was in the process of packing up his stuff for tomorrow too, and you could hear the shower running behind the bathroom door, so you assumed that’s where Jared was.
“Need any help?” you asked as you wrapped your arms around Jensen from behind.
He stopped what he was doing and turned to face you. “Depends,” he replied, “what do you want to help me with?”
“Seriously,” you rolled your eyes with a smile, “are you horny again? You guys are gonna break me before the trip’s over.”
He cradled your face in his hands and looked deeply into your eyes, “You know I’d never hurt you.” His lips found yours, softly, tenderly.
“I know,” you responded, breaking away from the kiss.
“But, seriously, how are you feeling? We didn’t get too rough with you this weekend did we?”
You smirked up at him, “You know I like it rough.”
“Mmmm,” Jensen groaned, crashing his lips into yours again, more fervently this time. His mouth left yours to explore your neck and he pulled down the front of your tank top to expose your breasts to him. “No bra this afternoon?” he questioned, “That’s my naughty girl.” His tongue ran circles around your right nipple before doing the same to your left.
Through short, shallow breaths you responded, “I figured I probably didn’t need one knowing the two of you.”
“You were right,” Jared’s voice surprised you from behind, his hands tugging your shorts down your legs and off your feet while Jensen continued to take your breasts into his mouth. He stood up against you and pressed himself into your ass, only the thin cotton of his boxer briefs between his hard-on and your panties.
Jensen’s hand rubbed up and down your abdomen, sporadically reaching between your legs to smooth along your cloth-covered cunt. His mouth still kissing your chest, while Jared sucked along your neck and shoulders, was making you heat up like an oven.
You reached up behind you to run your fingers through Jared’s hair and let out a moan as Jensen’s fingers slid underneath your panties and brushed along your wet folds. He played with your clit for a second before getting frustrated by the barrier between him and your sex, and then he pulled your underwear down, leaving you fully naked for the two of them to do as they wished with you. You weren't complaining.
Jared was grinding his erection against your ass now, and you bent forward slightly to encourage him further. His hands caressed your hips as he praised you. “That’s it baby girl, let me see that sexy ass.”
By now Jensen was down on his knees, he had taken his shirt and shorts off and was fingering your pussy gently, worried you might still be sore from the previous two days, and trying to get you lubed up enough so that they didn’t end up hurting you. Soon he removed his fingers and began laving at your folds with his expert tongue. “You taste so fucking good, sweetheart.” His tongue painted your pussy like a work of art, and then with one last lick up your slit he stood back up and dropped his boxer briefs to the floor, kicking them off his feet. Hoisting you up by the back of your thighs, he placed you down on the edge of the bed and pressed your legs up around your head, your knees bent by your ears, and stretching your snatch wide before him. He moaned in appreciation of the unencumbered view and teased at your opening with the tip of his cock.
Jared, who had stripped himself of his own boxers, was now kneeling on the bed next to you and offering his long, hard shaft to your lips. You turned your head and took him in, bobbing your head slowly and savoring the feel of him on your tongue. Jensen began plunging into you slowly while you gave his best friend head, everyone moaning in pleasure as you enjoyed yourselves.
You reached down and massaged your clitoris, and Jensen sped up his rhythm, his ass clenching with each thrust. “Fuck, baby, rub that clit. I love watching you play with yourself,” he said as he fucked you.
Letting out a moan around Jared’s cock, you pulled you mouth off him and ran your tongue from the tip down the vein that was throbbing on the underside of his shaft, taking his balls into your mouth one at a time. Jared let out a groan and tangled his fingers in your hair.
Cool air rushed between your legs, as Jensen pulled out of you for a moment. You whined at the loss of him, but he smiled down at you reassuringly. “Oh, don’t worry sweetheart, I’m not even close to finished with you.” He pressed forward, his cock now prodding at your ass, inserting just the tip and then pulling back out again. Inserting the tip again, pulling back out again, then sliding in a little further the next time, he was trying to get you accustomed to his size before fully sheathing himself inside. His fingertips splayed open your folds, exposing your perfectly pink pussy and he rubbed your clit with his other hand as he let his hips guide his cock deeper into your rear entrance.
Jared was cradling the back of your head now, as your eyes scanned down your body to watch Jensen’s dick slide in and out of your ass. You moaned and breathed, “Yes, yes, yes, God that feels so good!” while Jared stroked himself and then massaged your calf to help you keep your leg up and your sex exposed. You arched your back and let your head fall as you whinnied in pleasure from the way Jensen was driving into you.
“My turn,” Jared announced, and Jensen pulled out of you slowly. Jared laid back on the bed and tugged at you, turning you to face him so you could straddle him. You sank down onto his dick and began to ride him. You were so wet that he just slid right in. Rolling your hips, you worked him expertly, his breathy grunts and groans egging you on. Jensen just watched you work for a while, pumping his cock in his fist and spitting out an expletive or two under his breath.
You were lost in the feeling of writhing on top of Jared, so you didn’t see Jensen move to the bed behind you until you felt him probing at your tight rim with just the tip of his swollen head. You stopped moving, a little nervous because you had never taken two cocks at once. “Jensen, wait! I – I don’t know.”
He stopped, and rubbed a hand under the curve of your ass, spreading your cheeks apart slightly. “What’s the matter princess? You don’t think you can handle it?”
“I think she can,” Jared encouraged.
“All you gotta do is use your safe word. If you don’t like it, I’ll stop,” Jensen assured.
You were all breathing heavily with anticipation; they were both waiting for your go ahead. When you nodded, Jared grabbed ahold of your hips and held you still while Jensen slowly pushed himself inside your ass. You squeaked out in surprise as the fullness of having them both inside you was a feeling you never experienced before. Jensen stilled, allowing you to get used to the sensation.
“You okay?” he checked in with you.
“Uh, huh,” you breathed out. It felt tight now, but you weren’t sure how it would feel once they started moving again. It wasn’t long before you found out.
Jensen slowly and languidly pushed and pulled into you, causing you to slid along Jared’s length just enough to get the friction in both holes. You were breathing heavy and it felt weirdly good. Jared let Jensen drive for a moment until you let out a hearty moan and then he too began to work himself in and out of you. The two of them moved in and out in opposite directions. When Jensen pushed in, Jared pulled out. The feeling was incredible and before you knew it you were mewling in a sound so high-pitched that you thought only bats would be able to hear you.
“That’s a good girl,” Jared praised.
“You like being our good little cock-slut?” Jensen teased, “You’re taking both our cocks like a champ sweetheart.”
Their dirty talk and the intense pressure between your legs were all it took for you to topple over the edge, your orgasm soaking the three of you and the Jensen’s bed sheets. When you came down the guys stilled inside you, Jared propped himself up to kiss you deeply and Jensen pressed his chest up against your back to hold you steady, nipping gently at your earlobe.
“That was fucking amazing,” you enthused when you finally got your breath back.
Jensen’s breath was hot in your ear, “You think you can keep going?”
“Yesss,” you hissed, not wanting to stop.
You didn’t have to do a thing, Jensen pulled out of you and helped you off of Jared, and then the two of them maneuvered you so that you ended up in Jensen’s arms, facing him as he stood, your legs straddling his waist. Jared now stood behind you, helping to support your weight while Jensen lifted you from the back of your thighs and sank into your pussy again. Your head lolled back against Jared’s shoulder and then, he pushed himself into you from behind. A throaty moan fell from your lips and Jensen captured it with his own before he began to bounce you up and down on their engorged shafts. They didn’t take it slow this time, and that familiar feeling began to coil back up in your belly. Your bodies were all slick with sweat and the three of you were mumbling incoherently in between the animalistic noises that escaped. It was the most carnal experience you had ever had the pleasure of being a part of.
Once your climax broke, you let out a wail that could wake the dead, and Jared and Jensen both lost control, shooting their loads inside you from both ends. It took all their combined strength to keep you all upright until the shaking and shuddering stopped. When you all finally came down from your collective high, Jared helped Jensen lift you off of him and they carried you back to the bed, lying beside you. For what felt like an hour, but was probably only a few minutes, the three of you laid there on your backs just staring at the ceiling.
Jared broke the silence first. “You alright, Y/N?”
“Never been better,” you responded, “but I’m pretty sure I won’t be able to move for the rest of the night.”
Jensen laughed, that brilliant laugh of his. “You and me both, sweetheart,” he rolled over to face you, tilting your face to his so he could kiss the tip of your nose. “This was a really long weekend.”
“We definitely have to do this again next hiatus,” you announced.
Jared rolled into you then, his breath hot on the back of your neck. “I don’t think we should wait that long,” he suggested, “I’m thinking Wednesday.”
You giggled, “Oh I don’t’ know, if you let me sleep for an hour or two I think I’ll be good to go again.”
The boys both moaned in stereo.
“I think we all need some rest, and maybe one last good meal before we go attempting that again,” Jensen declared, “But I’m game if you two are.”
“So, sleep, supper, sex, in that order,” you yawned rolling over into Jensen and nuzzling into his chest.
“Sounds good to me,” Jared agreed spooning you and burying his face in your hair.
It only took seconds for the three of you to fall asleep, and you didn’t wake up until morning.