Chapter Text
“What’s your name?”
Dennis hated clubs. They were always loud and crowded, and he was getting too old for that shit. “What?” he yelled back, moving closer. He heard the man just fine the first time, he just wanted an excuse to scoot over into his space.
Dennis had a thing for older men. Maybe it was daddy issues or maybe he just really liked the stability and competence of an older, solid, experienced man. This man checked all his boxes. He was just a little taller than Dennis, shoulders broad and well muscled in his tight, black button up with the sleeves shoved up just right. Dennis's mouth watered at the sight of him. Dear God, already? Talk about the veins of his med student dreams. He was dressed very classy, and made Dennis feel that much sluttier in his Millennial ripped skinny jeans and mesh black shirt. Oh. They kind of matched.
The man gave him a wry little smile, pretty mouth fitting the expression so well. He had short, curly, salt and pepper hair and Dennis wanted very badly to drag his fingers through it. Dennis couldn’t help his smug smirk when the man moved closer, leaning in and putting his mouth next to Dennis’s ear. His cologne smelled so good. Mature and sexy and warm. “What’s your name?”
Dennis turned his head enough to put his mouth to the man’s ear. “Dennis. What’s yours?”
A hand brushed his hip. “Jack. Cool if I touch you?”
Dennis didn’t think his tipsy grin could get any wider. “Ooh, consent. Sexy. Yes, you can touch me.”
That hand landed on his hip, hot and big, fingers spreading out and brushing over his waist. “You here with anyone?”
Dennis shook his head carefully. “No, sir. Just me and a couple friends. They won’t mind if I get, ah, caught up.”
He could’ve sworn Jack laughed. Maybe he groaned? His fingers twitched on Dennis’s hip, and he moved a little closer. “Aren’t you sweet. Let’s find somewhere quieter.”
Dennis nodded, and let Jack guide him through the dance floor and out into the patio area, suddenly much quieter and slightly less crowded. At least, they could stand next to each other and not on each other. “Hi,” he said, grinning at Jack again. “You’re hot.”
Jack did laugh this time, deep and a little rough. “Thanks, Dennis. I got that right?”
A nod. “So… me?”
“Oh, yeah,” Jack said, still amused. “You’re the kind of trouble I can’t resist.”
Dennis rocked up on his toes, leaning a little closer. “Does that mean I can expect to go home with you? I’d like to.”
A pause, Jack’s eyebrows going up. “Awfully confident, aren’t we?”
A shrug, and he intentionally leaned even closer, losing his balance slightly. Jack’s hands caught him by the waist, warm and steady. Dennis put his hands on Jack’s chest automatically, looking up at him. Dennis didn't usually pay attention to chest muscles but... Wow. “Less confidence. More… alcohol and being hopeful.”
Jack’s eyes were dark, and hungry. Dennis couldn’t help the little shiver down his spine. He sort of got the feeling that Jack wanted to eat him. “You really want me to take you home, angel?”
Dennis nodded quickly, Jack’s hands on his waist burning against his skin. Angel. “Absolutely. But, I should tell you now; I’m trans. If that’s—“
“Not a problem,” Jack said, pulling Dennis a little closer.
Dennis gave him a very pleased smile. “Thank you for being normal,” he said.
Jack scoffed. “You shouldn’t have to thank me for basic decency, Dennis. My place or yours?”
Dennis winced a little. He… didn’t really have a place. He was sort of couch surfing and sort of staying in an abandoned wing in the hospital. He couldn’t afford rent on his own, and hadn’t had any luck on the roommate front. Not that he could really afford that, either. All of his money went to student loans, groceries, and his parents. He’d had to pull out enough cash for this little going out thing. His dad still had access to his bank account. If Dennis didn’t have autopay on for his loans, his dad would take that money, too. “I, uh, just moved here so I’m… couch surfing right now. So, yours, if that’s okay?”
Jack nodded, and pulled a set of car keys out of his pocket. “That’s fine. You should go tell your friends you're leaving.”
Dennis shrugged, and pulled his phone out of his barely there pocket. A quick text was sent off in the little group chat, and one thumbs up was received. Someone knew. “Done,” he said, putting his hand back on Jack’s chest.
“You kids and your texting,” Jack said, tone teasing. “Come on. I don’t live far.”
Dennis felt giddy, and a little tequila tipsy, bouncing on his toes as he let Jack lead him out by his hand, twisting their fingers together easily. It was shockingly easy to touch Jack, to feel comfortable. He didn’t, usually. Usually, his hookups had some kind of fetish for a man with a cunt, and wanted to treat him like a girl. Honey, sweetheart, and precious were things he was used to. He had slapped a guy across the face once when he’d slipped and called him baby girl. Jack’s angel felt different, somehow. More sincere. Sweeter. Right.
Jack drove a pickup truck. A blacked out, fancy, pristine black pickup truck. And fuck, did he drive it well. Damn that competency kink. Dennis grew up on a farm in rural Nebraska. Everyone drove trucks, and knew how to do it. People here, in the city? Some of the stupidest drivers Dennis had ever seen. Genuinely, he had started to lose faith for the people of Pittsburgh.
Jack knew how to drive a pickup. One-handed, to boot. Dennis couldn’t help the way he clenched around nothing when Jack landed one hand on his thigh, sliding up slowly to the junction of his hip and thigh. Two margaritas… He widened his legs slightly. Jack's other hand was casual and confident on the wheel as he drove them to his house.
“I didn’t think anyone knew how to drive pickup trucks anymore,” Dennis said, some of the arousal in his stomach threading into his voice.
“I grew up in the Deep South,” Jack said dismissively. “Of course I know how to drive a fucking truck.”
“That is so hot,” Dennis’s mouth said, with absolutely no permission from his brain. He flushed red, cheeks and ears burning. “Sorry.”
The hand on his thigh squeezed gently as Jack expertly maneuvered a turn. “Nothing to be sorry for. Where are you from?”
Dennis let out a shaky laugh. “The Midwest. Nebraska, specifically. On a farm.”
“Oh, so this is really doing it for you,” Jack said, teasing again.
Dennis whined, and poked his shoulder. “Don’t be mean.”
“I’m not, angel. Don’t worry, I’ll be sweet to you,” Jack grinned.
Dennis caught a truly embarrassing sound in his throat, and his face got even hotter. “You better,” he muttered, covering his face with his hands.
Jack laughed again, and then they were pulling into an alley in a really, really nice older neighborhood. He removed his hand from Dennis’s leg to reach up and press the garage door opener as they came to a stop in front of a detached garage.
It was a gorgeous 1940s red-brick situation, with a well maintained landscape, and a homey, comfortable look to it. Dennis almost wanted to cry when he followed Jack into the house. It was all original hardwood floors, built-ins, carvings in the wood, fucking stained glass in some of the windows he could see as he followed Jack through the beautiful kitchen, tile floors and wood everywhere, a cute little booth nook for a breakfast table.
He really did almost cry going up the stairs and seeing two more sets of stairs above them. It would be a very, very long time before he could afford a place like this. This was, like, a dreamhouse. He had never wanted something so badly. “Your house is gorgeous,” he said to Jack, envy bleeding into his voice.
“Thank you,” Jack said, and chose not to address the envy. “Do you want a tour, or do you want me to eat you out?”
Dennis choked a little, face burning again as his attention snapped back to Jack. “I— The second one? Please?”
Jack smirked at him, then pointed at the bed. “Strip. Then get face down on the bed.”
Dennis nodded, a little wide-eyed at how wet that made him. Goddamn daddy issues. He did as he was told, fumbling out of his too-tight clothes, and dropping them to the floor. He got his fingers in the lacey straps of the soft, worn black cotton thong he was wearing when Jack’s voice stopped him.
“Wait,” his voice was deep, rougher than before. Dennis stopped, and looked up at Jack with curious eyes. “Do me a favor, give me a spin. Slow.”
Dennis smirked, ears burning, and gave Jack a tortuously slow 360° turn. He heard the inhale when Jack got the full view of his ass. “Fuck, baby,” he groaned. “Get on the bed.”
Dennis went, melting into the soft-but-not-too-soft bed, raising his hips up to present himself to Jack. Those big, hot hands came a few moments later, sliding down his sides and over his hips, fingers plucking at the straps of his panties. “You are so fucking gorgeous,” Jack said, then pulled Dennis’s panties down and off — and Dennis glanced back to catch him shoving them into his front pocket — before bullying his legs apart with his shoulders and licking over his pussy.
Dennis gasped, hands fisting in the dark green comforter. “Jack,” he managed, and got another lick for it. “Please.”
“So sweet,” Jack murmured before actually getting to work, licking and sucking at Dennis, his tongue pressing in just a little every now and then.
Dennis was a lot closer than he thought he’d be, a lot faster than he thought he’d be. He could feel the pressure building, and he couldn’t help grinding his hips back into Jack’s face, whining and gasping. “Fuck, Jack, I’m close, I’m close, I’m—”
Dennis came suddenly, body going taught and clenching around still nothing, Jack’s tongue working him over as he twitched and shuddered and jerked before abruptly going limp, Jack’s hands the only thing holding him up. “Holy fuck,” he slurred, panting. “I’ve never cum like that before.”
“Thanks for the compliment,” Jack said, tone amused. “Sure you can keep up?”
Dennis frowned. “I can keep up.”
Jack’s hands slid over his ass, fingers spreading wide. Dennis twitched, and pressed slightly into Jack’s touch. Jack paused, then his pants were brushing against Dennis’s bare thighs. Fuck, Jack was still fully clothed. Dennis flushed, tucking his face into the comforter, trying to hide some of the red.
“I’m getting at least one more out of you,” Jack murmured, leaning over to press his mouth to Dennis’s ear. Dennis shuddered at the rough press of clothes against his overstimulated skin.
“Can you— Your clothes?” Dennis got out, shy and not sure how much he was allowed to ask.
Jack pressed a kiss to the tingly spot behind Dennis’s ear, then pulled back to tug his shirt off, wrestling out of his belt and pants. Within seconds he was naked, and Dennis twisted to see, immediately a little — a lot — impressed. Jack clearly took care of himself. He was fit, and strong, muscles defined but not unhealthy. Dennis let his eyes drip down, and inhaled sharply at the size of him.
Listen, Dennis had fucked around his fair share in med school. He had seen all shapes and sizes of dick. But Jack? Jack had the prettiest dick Dennis had ever seen. He was already fully hard, tip red and leaking pre-cum. He was slightly bigger than average, not too thick, like Dennis had found the Goldilocks of cock. “Oh my god,” he breathed, lust coiling tighter in his stomach. He was pretty sure was actually drooling this time.
“Thanks, Angel,” Jack said, leaned over as he messed with — Oh. He had a prosthetic on one leg. He was balancing very carefully, and Dennis watched curiously as he adjusted something he couldn’t see before bringing his knee up onto the bed. He was quick to press back up against Dennis, his dick brushing against Dennis, a hard, hot heat burning against his ass, just the barest brush against his pussy. Dennis couldn’t help his whine, and Jack chuckled.
“Need something, angel?”
Dennis nodded, burying his face in the comforter again. “I feel empty,” he got out, slightly muffled in the fabric. “Want you to fill me up, please?”
“For asking so nicely? Of course,” Jack said, and his fingers slid over Dennis’s pussy, collecting slick, then one finger pressed in slow and steady.
Dennis gasped, and shuddered at the intrusion, a quick, “Please, more.”
Jack let out a dark, growly sort of sound and suddenly three fingers were spreading him open. He cried out and moaned at the stretch, the thickness of Jack’s fingers. If his fingers felt like that… What would his dick feel like?
Dennis panted, “Can you— I think I’m ready.”
“You’re ready when I say you are,” Jack said, the tone in his voice making Dennis shudder.
“Please, Jack,” he breathed, and felt the shift in attention. “Please, I need it so bad. I need you in me so bad, Jack, please. Please don’t make me be empty. I’m so empty, please—”
“You are just so sweet,” Jack said, voice dark. Dennis shuddered again when Jack pulled his fingers out. The brief emptiness was quickly shoved aside as Jack pressed the tip of his cock in, just the barest tease of pressure.
“Jack, please,” Dennis whined, squirming his hips back. “You’re being mean, please let me have your cock. Please, I need it, I need it so bad.”
Jack sunk into him, slow but steady, unrelenting. “Fuck, Dennis. Fuck.”
Dennis moaned in response, immediately trying to fuck himself. Jack’s hands caught his hips, gripping so hard Dennis knew there’d be marks. Fuck, he hoped there’d be marks. “Jack, sir, please—“
“Oh, you’re gonna be the death of me, angel,” Jack said on a pained laugh, then obliged Dennis’s pleading.
The sounds he dragged out of Dennis were truly porn-worthy and utterly embarrassing. He made noises he never had before, hips fighting Jack’s grip — and failing — while he panted and whimpered and gasped. Jack talked to him here and there, told him how good he was being, hot and tight and sucking Jack in. The dirty talk ratcheted things up ten more degrees for him.
Much, much faster than he thought, Dennis’s orgasm was creeping up on him. The pressure was building quickly, and he unclenched one hand from the comforter to grab at Jack’s hip.
“Close.” He gasped, fingers digging into skin. “I’m gonna— Can I— Gonna come.”
Jack groaned, low and rough. “You are unbelievably perfect. Come. Now.”
Everything tipped over, and he came with a moan, breathy and barely there. Everything stopped for a moment, and Dennis had the awful, horrible urge to start begging Jack to keep him forever. He shoved it down.
“You’re so good, angel, so perfect and sweet. You’ve been so good to me. For me.”
“Inside, please,” Dennis managed, fingers clenching briefly.
“Holy hell,” Jack muttered, then gave a strangled gasp of his own, hips stuttering, and the heat soaking through the condom.
Both of them were quiet for a few moments, catching their breath. Dennis sank into the bed after Jack carefully pulled out. He couldn’t help himself. It was soft and comfy, but with the right amount of support. The kind of bed he dreamed of being able to afford one day.
A few moments later, listening to Jack rustle around, he felt a light tap to the back of his thigh. He stirred, automatically spreading his legs. Jack let out a soft little “Ha!” and a warm, wet washcloth touched his skin. Dennis shifted, but made a sound of contentment, relaxing under Jack’s gentle touch.
The cloth went away, but Jack’s hands stayed, starting to massage his thighs. Dennis moaned softly, melting under his touch. “Sorry. I left bruises.”
“Oh, good. I was worried there wouldn’t be any,” Dennis murmured, pleased.
“You wanna stay the night?” Jack asked after a very long pause. “Just— It’s late. And you’re already comfortable. I’d hate to make you get up.”
His hands kept working up Dennis’s legs. “You keep touchin’ me like that, I’ll stay forev’r,” Dennis slurred, more relaxed than he’d been in… well, ever.
Jack laughed, soft and deep. “Yeah, alright, baby.” His hands kept moving, and eventually Dennis fell asleep, warm, sated, a little sore, but very content.