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Dennis had sworn he’d seen this exact scene in a porn video once. Two hot dilfs standing in front of the bed as a twink sits before them, everyone’s eyes staring hungrily. Personally, he wouldn’t place himself in that subcategory of gay man, he had more muscle than that, but it didn’t stop Trinity from (affectionately) referring to him as her ‘emotional support twink.’
She’d called him that earlier, as they walked into the bar everyone was meeting at after work, claiming he just had to go with her despite how utterly exhausted he was. She didn’t even have to say anything for Dennis to know she wanted him to play wingman and drinking buddy. That’s how he found himself 2 shots of patron deep, sandwiched at the table of their coworkers between his attendings. The men themselves were sufficiently tipsy as well, glasses of amber liquid cleared in seconds after a long shift where Jack had to come in for backup.
Their conversation started out quite mundane, Dennis asking Jack if he liked overnights and if they were just as day shift in order to keep him from talking to Garcia. Next thing he knew, Robby was seating himself in the chair on the other side of him, jumping in to quip how the night shift likes to fill their time gossiping rather than working with patients. A friendly banter continued, Dennis pleased to be in the middle of it, seeing how loose and comfortable his boss had become in the familiar company and in combination with the alcohol. Before long, both men had brought their arms to rest across the back of his chair, leaning in closer under the guise of the loud environment. He could feel as their hands gently bumped each other, brushing against Dennis’s back and sending shivers down his spine. It was like they were playing footsie, fingers and wrists shyly dancing around the other.
Dennis’s eyes swept back and forth between the two men’s faces as the shots swam around his head. The alcohol was making him bolder as he laid a palm on each man’s thigh, their breaths hitching for a second before carrying on in their debate. Dennis had long tuned out of the conversation, but he was happy as a peach to stay seated between the men who came closer and closer, practically squishing Dennis between their chests. Was it weird if he said it was hot the way they were talking over his head?
He preoccupied himself by rubbing their thighs, the rough fabric of their pants catching on his dry hands. He listened as their breathing became heavier, sentences losing track if he dared to let his fingers graze higher.
“This party’s kinda lame, huh?” Jack muttered after a few moments of silence. “What’s it even for?”
“Just an excuse to unwind together, I think.” Dennis replied, peering up through his lashes.
“Hmm, a drink is always nice but I can think of a few better ways to unwind.” Robby added, the smell of bourbon clear on his breath; deliciously sweet. Dennis wanted a taste.
“What do you think about heading over to my place, brother?” Dennis’s breath stuttered at the posing of the question: directed at Robby only, as if Dennis wasn’t even there at all. He would’ve been worried about being left behind if it wasn’t for the solid hands laying on him, one on his lower back from Jack, the other on his shoulder from Robby, thumb grazing the exposed skin of his neck. It had a possessive manner to it— their hands staking their claim.
“I think that sounds like a great idea.”
No one was surprised when they all got up to leave, everyone waving their goodbyes while Trinity shot Dennis a knowing wink from her spot practically in Garcia’s lap.
Dennis was able to sneak a smoke against the brick wall outside, Jack trying his best to catch a cab as Robby stuck close by, their shoulders brushing slightly.
“You know those things’ll kill you.” His voice broke the silence as Dennis exhaled.
“Oh don’t play coy, brother. Not like you didn’t smoke those things longer than he’s been alive.” Jack shot back, flashing the screen for the Uber he’d ultimately ordered that was arriving in a few minutes. The statement had Dennis’s stomach tightening sweetly.
The ride to Jack’s place was quick with Dennis being shoved into the middle seat, both men bracketing him between their larger builds. Their legs pressed together as the driver quietly navigated the streets of Pittsburgh, Dennis letting himself lean in whatever direction the car curved.
Jack had a nice place; a decently sized apartment with a cozy atmosphere that felt lived in. Framed photos littered the walls of the entrance way, and Dennis had to push away the curiosity to look over them all that rose inside him.
“Anyone want a drink?” Jack asked as they stepped towards the kitchen.
“I thought drinking was boring?” Robby teased, a smirk playing across his features.
“Yeah I can think of a few more exciting things to do.”
Dennis let himself wander, hearing their voices fade as he floated his way to the bedroom, flicking on the bedside lamps before taking a scan of the room. It was filled with more framed photos, a couple books lining a shelf, and a large bed placed in the middle of the wall, fresh white sheets tucked perfectly on the sides.
Dennis flopped down on the end with a sigh, attempting to tamper down his excitement before setting his eyes on the doorway.
“Hey, Dr. Abbot? Dr. Robby?” He called, leaning back on his hands as he heard their footsteps approaching. “Gonna join me or what?” It was his open invitation, his consent signed, sealed, and delivered.
They stopped in front of the bed, the perfect pornographic picture painted in real time as their hungry gazes devoured Dennis from head to toe.
He shot a coy look of his own their way before patting the spaces flanking him on the bed. The plush comforter compressed under their weight, their legs pressed against each other. Heat radiated off of their bodies, the alcohol that had mostly worn off still warming their cores.
Dennis inhaled before leaning to his left into Robby’s space. They breathed each other’s air for a few seconds, Dennis drinking in the sweet scent of the man’s breath before diving in fully. Their lips connected in a slow kiss, Dennis’s hand coming up to cup Robby’s jaw, the hairs of his beard tickling his slender fingers. Dennis snuck his tongue in, tasting the bourbon still lingering on the attending’s own. The slick noise that sounded as Dennis pulled away echoed around the room. Robby panted, staring with lidded brown eyes that flickered down as Dennis licked his lips hungrily.
He could feel Jack’s breath on the back of his neck, sure that his eyes were entirely focused on the two of them. Dennis turned, steering Jack’s face with his two hands cupping his jaw until their lips caught each others’. He swiped his tongue along Jack’s bottom lip, quickly gaining entry as they kissed languidly. He could feel Robby’s eyes burning into his back, but he knew he didn’t have to worry about jealousy. He had the two men right where he wanted them.
Dennis pulled away, leaning back on his hands to sweep his eyes from one man to the other. As if in sync, they both bent in, mouths attaching to either side of his neck, licking and kissing and sucking. He let his eyes close, enjoying the sensation of the two men’s attention, the feel of their warm, wet breaths on his skin.
Slowly, as to not scare either of them away, Dennis reached up, lightly grabbing each man by the jaw and slowly pulling them higher and higher. Their kisses trailed, following his direction, already heady and pliant. He guided them farther, their mouths disconnecting as he brought their faces closer and closer. Their eyes remained closed, only flickering slightly once their lips connected, Dennis’s gleeful smirk hidden fully behind their interlocked mouths. He watched as the men kissed slowly, building up speed the more they got into it. He could feel their hands crawling across the bed behind him, fingers interlocking as soon as they touched. With Dennis’s hands holding their heads steady, their free hands made contact with his legs, Jack’s settling higher than Robby’s.
Dennis couldn’t help but pant as he watched his attendings make out, their tongues sliding against each other as they swapped spit. A faint moan slipped out of Robby’s mouth, the high pitched noise hitting Dennis right in the pit of his stomach, making him clench his thighs together.
They separated with a wet sound, panting as strings of spit broke against their lips.
“None of that,” Jack murmured, pulling on Dennis’s leg so that his thighs separated. The strength displayed by the older man had a whimper threatening to escape his throat that he barely managed to swallow.
He had some business to take care of first.
“Hey, uh, if we’re gonna do this, I should tell you guys something.”
He watched as both men sobered up slightly, enough to listen to what Dennis had to say.
He took a single deep breath. “I’m trans.” He peeked hesitantly between the men, their faces neutral, revealing nothing to him.
Jack’s voice broke the silence. “Same.” He gave a gentle, reassuring smile as Dennis’s face lit up slightly.
“Wait, really?”
“Yep.” He replied confidently.
Dennis wished he could ask the man a million questions in that moment, discuss the ins and outs of their similarity— hear his journey. But maybe now wasn’t the time.
Dennis looked to Robby expectantly, Jack’s gaze following that direction as well. The man straightened his back under the attention.
“Sorry to disappoint, but I have a dick.” Robby supplied, attempting to keep the vibe light. Dennis couldn’t help but let out a little laugh.
“Not a disappointment at all.” Jack purred, reaching his hand to stroke down Robby’s thigh. “In fact, I have plenty of dicks of my own.”
Dennis watched alongside Robby as Jack walked to the closet, pulling out a plain looking box before dropping it onto their laps.
“Go ahead, open it.”
Dennis lifted the lid off, his breath speeding up at the sight of multiple dildos, some loose, some already mounted on harnesses, crowding the box.
“Wanna pick one out?” He asked, head tilting slightly as he smirked. Dennis licked his lips in excitement before letting his eyes roam the contents. He pulled one out, a light blue base and head with colorful stars decorating the inside. It was probably about 6 inches long. “Good choice.” Jack commented before turning towards Robby. “We’ll have to compare, brother. See who has the better dick.”
“I can guarantee mine won’t look as pretty.” He joked, staring wearily into the box still opened on Dennis’s lap.
“Don’t worry, I won’t use any of these on you. Tonight.” A devilish smirk crossed Jack’s features as a heavy blush stained Robby’s face and neck.
Dennis was sure the man hoped neither of them noticed it.
“As for you…” Jack leaned over Dennis, capturing his mouth again as he took the lid from his hands. The box was moved to the side so that Jack’s hands could roam his body, tingles following in their wake. Robby went back to focusing on his neck, licking and sucking marks that were sure to linger for a few days. Trophies he’d gladly parade around.
Dennis sunk into the feel of the two men on him, invading every part of his brain as they slowly pulled him apart and put him back together. His hands fisted in the bedsheets, excitement overwhelming him. He attempted to find purchase on Robby’s thigh, his warm palm brushing against the fabric of his pants. Robby’s finger dipped into the collar of his shirt, stretching it so he could lay a particularly harsh bite on the junction there.
Dennis flinched, his hand accidentally skirting higher as he moaned into Jack’s mouth. Robby let out a groan as Dennis’s hand brushed against his clothed dick, warmth seeping through the fabric.
“Fuck, sorry.” Dennis panted, pulling back from Jack’s lips.
“I don’t think that was a groan of pain, baby.” The older man supplied, lips red and spit slick. “Got a little problem there, brother?”
Robby glared at Jack, though no malice was behind his eyes. “Little.” He scoffed as if he couldn’t believe what he’d heard.
“Oh, so that’s what pissed you off?” Jack barked a laugh.
“It’s not little, I can tell you that.” Robby shot back, jaw set in annoyance.
“Prove it.”
Jack's hands were on Robby quick and Dennis pulled away so he could get a better view. It was like a string had finally snapped, the two men heatedly making out as Jack undid Robby’s pants, fishing inside his boxers to pull his dick out. Robby moaned at the touch, the sound bringing another bout of wetness to Dennis’s own boxers.
“Not bad, not bad.” Jack whistled once, staring down at Robby’s dick, the tip already red and leaking.
Dennis couldn’t help but stare. He’s been wondering for so long what his boss’s dick looked like, trying and failing to catch a glimpse in the bathroom like a perv.
“Like what you see, doll?” Jack called out, Dennis’s attention being ripped from one thing to another. He licked his lips, sinking his teeth in afterwards as he wondered what it tasted like.
“You can touch.” Robby said lowly, his deep breaths making his shirt pull tight over his chest. Dennis’s eyes slid to his face, then back down to his dick.
“I wanna do more than touch.” He confessed, practically a whisper as his head spun.
“Scoot up, brother.” Jack motioned to the top of the bed, Robby following the command without protest. “Come here.”
Dennis’s shirt was pulled over his head by Jack, the man’s eyes dropping down to the tape secured on his chest.
“Want to leave it on?” Dennis knew he was just being polite, knew that Jack knew it wasn’t a good idea. He wasn’t too keen on rubbing his skin raw at the moment anyways. He shook his head, watching as Jack started his walk towards his en suite before he turned his head and shot a finger in Robby’s direction. “Take your pants off, old man.”
Robby huffed a laugh, starting to wiggle his legs free as Jack returned with a small bottle of oil. He knelt on the bed gently and dabbed some on his fingers before rubbing it along where tape met skin.
“Don’t be useless, come help me.” He called to Robby, not even looking in his direction. The other man readily crawled forward, Dennis doing his best not to watch as his dick swung uselessly between his legs. “Remember back in med school when I called you over because I got stuck in my binder?” Robby and Jack chuckled at the memory, fond smiles playing across their faces.
Dennis couldn’t help but blush, the care that the two men were putting into him had his heart racing in a different way than it had the rest of the night. The gentle care and attention they were putting into him was like nothing any partner had ever done for him before. Sure, Trinity had cleaned him up and taken his binder or tape or whatever else off on a sloppy night out, but that was different. This was something else entirely.
“Ok, that’s gotta sit for a couple minutes, so why don’t we have some fun?” Jack said, throwing the oil bottle to the nightstand before pulling off his own shirt. Dennis probably had stars in his eyes as he marveled at Jack’s top surgery scars— a dream for future him.
“Can I?” Dennis asked hesitantly, reaching towards Jack’s chest slowly.
“Sure, baby.” He gave a sweet smile.
Dennis’s fingers brushed gently against the red marks; they’d obviously faded over time, but Dennis knew exactly what he was looking for. He let his hands run over Jack’s chest as he stared awestruck.
“I appreciate the love, doll, but I think our friend over there might need some help before he starts to hurt.” Jack teased, taking one of Dennis’s hands and bringing it up to kiss his palm. “Sit back.”
The command was directed at Robby, who eagerly flopped against the pillows.
“Your turn.” He motioned for the bearded man to remove his shirt, the fabric dragging against the hair that littered his torso on the way up.
“Now it’s your guys’ turn. I’m not gonna be the only one completely naked here.” Robby said, resting against the pillow in all his dad bod glory.
“You heard the man.” Jack quickly shucked his pants and briefs off, Dennis following suit without complaint. His eyes ping ponged back and forth, warmth traveling up his spine as he looked over the men in front of him. He couldn’t stop his hungry gaze moving from Robby’s hairy chest, solid pecs leading down to a soft tummy, to Jack’s graying bush, his hardened dick peeking out through the curls. As soon as he brought his line of sight back up, he noticed the men were staring at him too, fire crackling in his belly at the thought.
Jack reached out, pulling Dennis by the neck into a kiss, fast and wet as he slowly pulled them both lower and lower until they were level with Robby’s dick. The older man’s breath hitched as Jack parted their kiss, licking a long stripe up the side of his cock. Robby’s hand shot into Jack’s hair, pulling and pushing as he started to mouth up and down the dick. He locked eyes with Dennis who quickly got the hint, bringing his lips to the other side to leave wet kisses and kitten licks.
“F-fuck,” Robby’s stuttered out above them, his free hand coming to massage at Dennis’s shoulder.
Dennis watched with a lidded gaze as Jack reached up, his hand cupping and squeezing at Robby’s pec. The man threw his head back in pleasure, moaning loudly as his fingers tugged on Jack’s curls. His body was so soft and mailable, similar to Dennis’s own chest and it gave him a surprising sort of gender euphoria. Mostly though, it just made him more horny.
Jack pinched at his nipple and Robby’s hips bucked against their mouths as he whined. It was so incredibly sexy how heady Robby was becoming. Dennis reached his own hand up, feeling the man’s warm chest and rapidly beating heart. His hair was coarse to the touch and Dennis wished he would grow chest hair like that some day.
He and Jack continued to mouth at Robby’s dick, Dennis trailing upwards in order to lick at the head, dipping his tongue in the slit.
Jack pressed a kiss to his temple, brushing his lips against his ear as he asked, “How do you feel about anal?”
Dennis moaned at the dirty words, the sound buzzing around Robby’s dick as he suckled on the head. He nodded feverishly, leaving a kiss on the tip so he could pull up just a bit to speak.
“Did it once, felt good.” He panted out, too heady to string together a better sentence.
“Good.” Jack left a sloppy kiss on his shoulder before pushing his head back down until he was swallowing Robby’s cock. Dennis whined, the pleasure of being forced down too much to hold it in.
He could hear the snap of something behind him, but paid it no mind as Robby sweetly brushed his sweaty hair off his forehead, flashing him a smile. Dennis tried to reciprocate, but the feeling of Jack’s hand on his ass had him whipping his head around. Before he could question anything, Jack ran a slippery finger over his asshole, pulling a sharp gasp from Dennis’s lips as he slipped a finger in.
Dennis laid his head on Robby’s thigh, grinding his face against it as Jack skillfully pumped a finger in and out.
“How’s it feel?” Jack asked, a soothing hand rubbing against his lower back as Robby’s hand weaved into his hair, providing equally soothing strokes.
“Burns a little,” Dennis panted out.
“Hmm.” Jack hummed in understanding before pouring more lube over Dennis’s hole, the extra help in gliding feeling much better. He moaned out as Jack continued to stretch him, soon adding a second and third finger as Dennis got looser.
Before long, he was pushing back into Jack’s hand as he thrust his fingers quickly, the wet noises from the lube echoing around the room. Dennis continued to mouth at Robby’s dick, the older man carding his hands through his hair as he pushed down slightly any time Dennis moaned around it.
“I think he likes it when you force him down.” Jack chuckled, the embarrassment of being laughed at causing Dennis to drip harsher between his own legs.
Robby gave a tentative push on his head, Dennis keening in the back of throat at the movement. He did it again, this time a little harder, pushing Dennis further down his dick as his throat contracted a bit.
“He’s so fucking wet, Robby.”
“Fuck, who gets dibs first?”
“He’s got two holes doesn’t he?”
“Fuck, yeah, you’re right, brother.”
Dennis’s head spun listening to the two men talk about him like he wasn’t even there, like he was an object to play with rather than his own person.
Jack gave a few last thrusts, spreading his fingers to see the stretch before pulling them out. Dennis thought he’d get a moment to breathe before the man laid a firm spank right on his cunt. He jolted forward, letting out a high pitched “ah!” that would’ve had him embarrassed in any other situation, but he was just too horny for that now.
“Come on, baby, time to have some more fun.” Jack pulled at his waist, sitting Dennis up until he was leant against Jack’s chest. “Let’s get this tape off you.”
The older man started to peel it off gently, Robby leaning forward to start on the other side. Within seconds, Dennis’s chest was free, Robby’s warm hands cupping his chest to massage them.
“Feel better, baby?” Jack asked, rubbing any left over oil into his skin.
Dennis nodded, the touches of both men duly overwhelming and not enough as he let his head loll back onto Jack’s shoulder.
“Ready for daddy to fuck you?” Jack asked, pressing a sweet kiss to the side of his head.
“Woah, Jack-”
“Mhm, please.” Dennis cut Robby off, heated gaze searching for those deep brown eyes.
“Ok, switch.” Jack resituated him until his back was pressed against Robby’s chest and Dennis reached up to pull Robby into a lazy kiss.
“Mmm, daddy.” He moaned into the older man’s mouth, feeling as his dick twitched against him. “Fuck my ass, please daddy. I want it.”
Dennis watched with lidded eyes as Jack leant in, whispering something into Robby’s ear before backing up, a sly smirk on his face.
“Ok, daddy?” He purred, Robby nodding viciously as his grip around Dennis’s waist tightened.
“Come here, Den.” Robby called, guiding his waist until he was raised above his dick.
Dennis bit his lip in nerves; he knew a position like this would be so much deeper than something like missionary and it kind of scared him. But it also thrilled him.
He waited as Robby poured some more lube on his dick before feeling the man line himself up. Jack placed himself between the men’s tangle of legs, hands roaming over Dennis’s chest and waist and belly and shoulders, distracting him as he was pulled onto Robby’s cock. He sank lower and lower, staccato moans escaping from his throat as he could feel himself stretching around the intrusion. Once he bottomed out, Robby gave him a moment to breathe, whispering soothing praise into his ear as Jack left marks along his shoulder.
“Good job, baby. Did so good for me. My best boy.” The words were like liquid honey seeping from Robby’s lips into the depths of Dennis’s brain. He whined, squirming as the position got uncomfortable, the need to move overtaking his mind.
“Ready, baby?” Robby asked, pressing a kiss just below his ear. The moment that Dennis nodded, Robby started to roll his hips, pressing even farther into his body.
Dennis melted, the slow thrusts driving him insane.
“Fuck, so deep. So big.” He panted out, unable to stop the train of thought from dribbling from his lips.
“Don’t praise him too much, doll, or he’ll get a big ego.” Jack teased, gaze catching Robby’s eye over his shoulder.
“Ha ha.” Robby barked back dryly. The older man leaned back against the pillows, one hand clung to Dennis’s hip as the other smoothed up his back. “You gonna make me do all the work, Den? Thought we were a team here? Where’d all that enthusiasm go when you were making me and Jack kiss?”
“Fuck, that was hot.” Dennis moaned out, the memory of not long ago resurfacing in his brain. That image will definitely be tucked away nice and safe for the next time he needed to get off.
The two men chuckled, Jack taking Dennis’s face in his for a kiss. He wrapped his arms around the older man’s shoulders, using him to lean on as he rose on his knees before pushing himself back down. Robby moaned as the feeling, Dennis getting encouraged to work harder. He bounced himself on the man’s dick eagerly as Jack licked his way into his mouth. He couldn’t help but reach down, his fingers ghosting hesitantly over Jack’s dick.
The older man moaned, sighing into Dennis’s mouth as he continued to stroke. Robby aided him in his movements, grabbing hold of his waist as he pushed and pulled Dennis on and off his dick so he could focus on playing with Jack.
He swiped over his hole to catch some wetness, the glide over his dick much easier with the help. He rubbed in circles, feeling the way it twitched under his touch. Dennis hadn’t been on testosterone for long (access was hard when you’re a broke student) so he was excited to actually get a feel of a real T-dick. He marveled at how much it had probably grown, the way it hardened, and just how much pleasure it was giving Jack to be touched.
Dennis was wrapped in a cacophony of moans, Robby groaning and whining behind him, while Jack was moaning and sighing into his mouth. His stomach was tightening at what he was hearing, knowing the noises would be stuck in his head like a looping record.
Jack disconnected their lips, laying a sloppy peck on the side of his mouth before he gave a determined nod in Robby’s direction.
Dennis was about to ask what was going on, but was quickly cut off as Robby hauled him back, sliding down until he was laying on his back, Dennis on top of him. Robby easily stayed inside him, big hands coming to spread his legs apart, much to his embarrassment. As much as Dennis tried to fight, he was no match for Robby as he pulled his legs apart, settling them on the outside of his own knees.
Jack settled in the spread, running a finger from Robby’s balls, up, up, up in a line until he reached Dennis’s dick. The movement had both men shivering, Robby’s dick shifting inside Dennis.
“This is embarrassing,” Dennis whined, covering his face with his hands.
“What is? Having your pretty holes out on display for us? Daddy’s having a good time fucking your ass, though, isn’t he?”
Robby responded with a roll of his hips, Dennis squeaking in surprise.
“It feels good, doesn’t it, Dennis?” Jack teased, running a finger down his slit. As much as he wanted to deny it in embarrassment, his body betrayed him, a big drip of wetness slipping from his folds, over his perineum, to where Robby’s dick was settled comfortably in his asshole.
He shamefully nodded his head, not daring to peak between his fingers.
“Why don’t we have some more fun?” Jack suggested, that evil smirk planted on his face once again.
Robby’s hands came up to meet his own, weaving their fingers together so he could pull them away from his face. He had to watch as Jack took a few fingers in his mouth, wetting them thoroughly before they teased as his entrance. As soon as Jack pushed a finger in, Robby’s own thrusts resumed, his feet planted firmly on the mattress.
Dennis cried out, fighting to pull his hands away from Robby’s to no avail.
“You’re so wet, baby. Daddy making you feel that good? I bet I can make you feel even better.”
Robby scoffed behind Dennis’s head, kicking Jack in the leg to which the man just laughed. His fingers thrusted deftly, the same way they opened up his ass before, except this time it was even louder. With the amount of wetness that Dennis had been producing all night, the sounds were obscene. Loud, wet squelching filled the room alongside the noises of skin slapping skin, Robby still drilling into him from underneath. The old man’s hips were gonna hurt tomorrow.
Dennis was practically sobbing out moans and high pitched whines, his body quickly turning into something for the men to use. He felt full, overly so as Jack stuffed three fingers inside him and Robby’s dick grinded in slow circles.
Suddenly, Dennis remembered. The strap. He wanted to protest, say it was too much, but who was he kidding? This was like his biggest fantasy. Day 1 of his ED rotation and he was dreaming of being squashed that way and other between his two attendings.
Jack laid sweet kisses along his belly, Robby finally letting go of his hands, knowing he was now too limp to move them much. Dennis twitched as Robby’s fingers came to rub his dick, his thick finger dipping in alongside Jack’s for a moment to coat it in the wetness dripping out of his hole.
As soon as the man started playing with his dick, Dennis could feel the heat in his belly tighten.
“Fuck, I’m gonna-” He panted, hoping the warning would back them off. Wrong. They just went harder.
Jack scissored his fingers, stretching Dennis to his limit before thrusting roughly, his fingertips petting at the walls of his insides. Robby increased his thrusts, pounding his ass as he stroked over his dick.
“C-cum- I’m cumming!” Dennis cried out, feeling as more slickness gushed from his hole, everything clenching as tried to pull away from all the sensations. A white heat flashed over his body until it sagged in the aftermath, panting heavily from the force of his orgasm.
Robby slowed his thrusts, removing his hand to stroke over his hip affectionately. He laid gentle kisses on his neck, Dennis craning his head so he had better access.
Jack pulled his finger out slowly, licking away any excess wetness clinging to the digits before laying a kiss on Dennis’s forehead. They all stilled so Dennis could catch his breath, except for Jack who got off of the bed, returning to view with a black harness in one hand, and the dildo Dennis had picked out in the other.
Dennis whimpered, the idea of anything else getting stuffed inside him making him prematurely exhausted, but simultaneously horny as hell.
He watched as Jack set up the strap, stepped into the harness and slathered a good amount of lube onto it.
“You look pretty hot in that thing.” Robby chuckled, but the way his dick twitched inside Dennis revealed exactly how the man actually felt.
“Oh, yeah?” Jack teased, kneeling between Dennis and Robby’s legs, one hand wrapped around the dildo his he stroked over it, spreading the lube from tip to base. “Maybe I’ll have to fuck you with it next time.” Jack leant over, speaking the words slowly into Robby’s face as he pushed inside Dennis. He was thoroughly sandwiched between the two men.
He could feel Robby twitch inside him again as the man brought a hand to the back of Jack’s head pulling him in for a kiss.
“Yeah, yeah, ok.” Robby nodded vigorously into the kiss and both men started thrusting sloppily into Dennis, obviously too preoccupied with their own tension. The fact that he was being used as a vessel for their fantasy thoughts was honestly incredibly hot.
The older men aggressively made out, Dennis getting a front row seat as he was being pounded from both angels. Wetness poured out of him as he bit his lip, trying to hold back his noises so he wouldn’t disturb the two men moaning into each other's mouths.
“Fuck, I’m getting close,” Robby panted out, disconnecting from Jack’s lips.
Jack sat up straight, pulling Dennis closer by the waist so he could thrust harder.
“God, this is the sweetest hole I’ve ever had. What about you, brother?”
“Mine’s pretty sweet, too. Nice and tight around my dick.” Robby’s thrusts were getting sloppier as his climax was obviously getting closer, but all Dennis could think about was “mine.”
“Bet you’re jealous I get the one that’s leaking like crazy, he’s wet all over my dick.”
“Hmm maybe next time.” Next time.
“Yeah? Next time you can have his wet cunt and I’ll get to have yours, how does that sound?”
The way they were speaking like Dennis wasn’t even there was making his head spin, their thrusts entering him at different times and speeds.
“Fuck!” Robby called, so obviously close to the edge.
“What do you think, baby? Wanna watch me pound daddy into the mattress?”
Dennis nodded vigorously, opening his mouth to answer, but receiving Robby’s thick fingers in his mouth instead.
“Too bad you can’t feel this pretty hole on your dick.” Robby quipped while Dennis dragged his tongue around his digits.
“I’m sure he’s great at eating out, aren’t you, doll?”
Dennis gave a weak nod. It was a lie due to his inexperience with women or other trans men, but he sure as hell could try.
“Fuck, that’d be hot.” Robby panted, giving a few final hard thrusts before pulling out, his warm cum painting over Jack’s legs and Dennis’s ass.
“Ugh, now I’m gonna be all sticky. You better clean that up later.” Jack grumbled. Dennis could tell he wasn’t actually mad, but the banter was fun to observe.
“Of course, baby.”
The pet name had Jack blushing, turning his head in an attempt to hide it. Robby let out a huff of laughter.
“You wanna come again, my good boy?” Robby murmured into Dennis’s ear, his hand already sneaking down to rub at his dick again. “Does it feel good when he fucks you? Pretty, decorated dick messing up your insides? Does it go as far as me? Is it as big as me? I doubt it.”
Dennis panted harshly, all language gone from his brain as he moaned and whined and keened.
“Your cunt sounds so wet; I wish I could get my fingers in there too. Think I could do that, pretty boy?” Robby’s hand snuck further, a single thick finger pushing in alongside Jack’s strap as his thumb took over rubbing against his dick.
Dennis gasped, the stretch stinging before giving way to pleasure, his own hips canting against Jack’s thrusts. The man above him looked so sexy, focused gaze trained on where his strap was slapping against Dennis’s skin. The grip on his hips was tight, pulling him to meet each movement.
“Gonna- cum,” Dennis forced out, his only warning before he was clenching around everything inside him, back arching off Robby’s chest as his orgasm ripped through him. He shook slightly on the comedown, tired eyes blinking slowly.
“You did so good, baby, such a good boy for us.” Robby praised, laying kisses on his cheeks and head, wiping his hand on the bed so he could hold the younger one close.
Jack slowly pulled out, careful not to drag too harshly before he laid kisses of his own across Dennis’s chest.
“You did wonderful, doll. You were just perfect.”
Dennis smiled goofily at the praises, squirming until he was able to roll off of Robby and onto his side. He made sure he was facing the two men as he breathed deeply, calming his pounding heart.
“What about you?” He mumbled out, eyes trained on Jack as he removed his strap.
“Nah, I’m fine,” he attempted to brush it off, Dennis pouting at the rebuttal.
“Bullshit. Come here.” Robby pulled Jack over pushing him incessantly until he was positioned over Robby’s face.
“What are you-” He cut himself off with a gasp as Robby pulled him down, his tongue quickly entering the other man’s hole. “Fuck, Robby! St-” As much as he wanted to protest, Jack couldn’t hold back the moans that poured from his mouth.
Robby held his thighs tight, swiping what was left of his own cum that hadn’t dried against Jack’s thighs and extending his arm up.
Jack rolled his eyes before licking at Robby’s fingers, taking them into his mouth as he groaned around them.
Dennis watched in awe, seeing the two men’s barriers finally break down for good as Robby enthusiastically ate Jack out. If his body wasn’t so spent, Dennis would’ve been touching himself to the show. He watched as Jack grinded down against Robby’s face, his nose the perfect seat for his hard dick.
“Robby- I’m close!” He pulled on the man’s hair as Robby moved to sucked his dick, running his tongue over it repeatedly. He pushed Jack’s hips up a bit so he could breathe for a moment.
“Come whenever you want, baby.” He mumbled, Dennis catching sight of how soaked his lips and facial hair were.
He snuck his hand behind, pushing two fingers into the other man immediately.
“Fuck! Oh my god!” Jack moaned out, rocking onto the thick fingers as he threw his head back.
Dennis reached forward, rubbing gently on Jack’s thigh and leaving a few sweet kisses against his knee. It was quite obvious the man was used to being a service top, not exactly worrying about getting himself off as long as his partner was happy. To each their own, but getting finger fucked and sucked off every once in a while would do him some good.
“Cumming! Fuck- broth- Michael! Fuck!” Jack strung together, obviously losing himself a bit to the pleasure as his orgasm hit, Robby eagerly working him through it.
He pulled his fingers out slowly, the slickness helping before Jack stumbled off Robby’s face, landing next to Dennis. The younger gave a sweet kiss to Jack’s thigh, interlacing their fingers as the older man took deep breaths. He opened his eyes, smiling sweetly down at Dennis before running his fingers through his matted down curls.
“Hi, pup.” Dennis blushed at the pet name, hiding his face in Jack’s thigh.
“Fuck, I’m so tired.” Robby groaned, rolling on his side and stretching. “My backs gonna fucking hurt tomorrow.”
“And who’s fault is that?”
“It was well worth it.” Robby smirked, tucking a strand of hair behind Dennis’s ear. They stayed in silence for a little while, Dennis dozing off as he was pet, the high of his climaxs wearing off into pure exhaustion.
“Ok, time for bed!” Jack declared, breaking the quiet air around them. Everyone shifted until Dennis was in the middle, Jack spooning him from behind as Robby faced him.
“Goodnight, everyone, don’t wake me tomorrow, I’m off shift.” Robby said with a smirk, closing his eyes to let himself settle.
“Fuck, I have work.” Dennis groaned, curling tighter into a ball.
“I’ll be there with you, doll.” Jack murmured, laying a kiss on Dennis’s back.
“Heh,” Robby let out a teasing laugh, receiving a whack on the arm from Jack.
“Shhh! Go to bed.” He scolded, his grip tightening on Dennis, but his hand lingering on Robby’s arm gently.
“Goodnight.” The attending sighed, pressing one last kiss to Dennis’s forehead as he drifted off. The last thing he remembers is feeling Robby lean over him to plant a kiss on Jack’s temple.