Nate’s first massage.

[kcdave]

A couple of months ago, I grabbed drinks with my buddy Nate, something we’ve done every few weeks for years. I’m gay, and Nate’s always been the straight one—my only straight friend, really. At 50, he’s single, never married, and has this rugged charm: salt-and-pepper hair, a solid build from years of hiking, and a quiet intensity. We’ve been tight since our late 20s, and I came out to him early on. He took it in stride, and over time, he’s been nothing but supportive—joining me at pride events, meeting my partners, the works.

That night at the bar, after a few beers, the talk turned personal. Nate’s been on his own for a while, dodging dating apps and shrugging off any nudge toward romance. I’d always wondered if there was more to it—if maybe he’d built a wall around something he didn’t want to face. So, I took a shot.

“Ever think there’s a side of you you’re not letting out?” I asked, keeping it light. “You’re 50, man—single, no baggage. What’s holding you back?”

He smirked, sipping his beer. “What, you think I’m secretly pining for someone? I’m good, Ethan. Solo life suits me.”

“I’m not saying you’re pining,” I pressed. “But you’ve never seemed all that into the women you’ve dated. Ever wonder if it’s not women you’re after?”

He froze, then laughed it off. “You’re barking up the wrong tree. I’m not gay, Ethan. I’d know by now.”

“Maybe,” I said, leaning in. “Or maybe you’ve just never let yourself feel it. You’re curious—I’ve seen it. The way you talk about guys sometimes, how you notice stuff. You don’t have to be loud about it to wonder.”

Nate shifted, uneasy. “I don’t know what you’re getting at. I’m not hiding anything.”

“Alright, hear me out,” I said. “I’ve got a friend, Jason. He’s 35, gay, and does these amazing massages—erotic ones. He’s got a knack for helping guys like you—straight, curious, whatever—relax and figure shit out. No pressure, just a safe space to feel good and see what clicks. You’ve got nothing to lose.”

“Massages?” Nate raised an eyebrow. “What, he’s gonna rub me into being gay?”

I grinned. “Nah, he’s not a wizard. But he’s chill, hot as hell, and he lets clients explore—touch him, whatever feels right. Worst case, you get a killer massage and walk away. Best case, you learn something about yourself. You’ve been stuck in neutral too long, man. Give it a shot.”

Nate stared at his beer, then at me. “I don’t even know how that’d work. What if I hate it? What if he’s not my type?”

“Jason’s a pro,” I said. “He’ll explain everything upfront, and you can bail anytime. As for your type—tall, lean, dark hair, killer smile—he’s easy on the eyes. I’ve got a pic.” I pulled out my phone and showed him: Jason in a tank top, all lean muscle and quiet confidence. Nate glanced, then looked away quick, but I caught the flicker in his eyes.

“Think about it,” I said. “I’ll set it up if you’re in. Next Saturday work? You’ve got no plans, right?”

He hesitated, then muttered, “Fine. One-time thing. Don’t make it weird.”

I called Jason that week and booked it—Saturday afternoon at his place. “He’s nervous,” I told Jason. “Fifty, straight his whole life, but I think he’s been hiding from himself. Go easy, but don’t hold back—he needs the push.”

Saturday rolled around fast. Nate texted me that morning: Still think this is nuts, but I’m going. I told him to relax and enjoy it. He’d been hiking all week, so his body was probably aching anyway—perfect excuse for a massage.

Jason lived in a sleek loft downtown. Nate showed up in jeans and a faded tee, knocked, and Jason answered with that disarming grin of his. At 35, he’s got this youthful energy—tall, wiry, with a smooth chest and dark eyes that put you at ease. He wore a loose gray robe and welcomed Nate in like an old friend.

“Shoes off by the door,” Jason said, leading him to a back room. It was cozy: a massage table center-stage, dim lights, soft jazz playing, oils and candles scattered around. Nate sat on a chair, hands in his lap, while Jason broke the ice.

“First time’s always weird,” Jason said, sitting across from him. “We’ll go slow. Tell me what you’re here for—Ethan said you’re curious, maybe unsure. That right?”

Nate shrugged, voice low. “I don’t know. He thinks I’ve got some hidden gay side. I’m not sold, but I’m here. Figured I’d see what the fuss is about.”

“Fair enough,” Jason said. “No labels, no rush. Here’s how it works: you strip down, lie on the table face-down, towel’s optional. I’m usually naked too—cool with that?—and I’ll start with your legs, work up to your back. Then you flip, and it gets more sensual if you’re up for it. You might get hard; I might too. It’s normal—don’t sweat it. Touch me if you want, stop me if you don’t. Sound doable?”

Nate nodded, slow. “Yeah. Simple enough.”

“Great. I’ll step out—get comfy.”

Jason left, and Nate undressed, folding his clothes on the couch. He’d never been big on massages, but his stiff muscles were screaming after the week’s hikes. He climbed onto the table, face-down, towel over his ass, feeling exposed but oddly curious.

Jason returned, and Nate felt warm oil hit his calves as Jason’s hands got to work. The guy was good—firm strokes melting the tension, then lighter ones that sent a shiver up his spine. When Jason reached his thighs, Nate felt skin brush his feet—Jason’s cock, soft and casual. More oil, deeper rubs, and Nate’s toes grazed Jason’s balls as he leaned in. It was strange, but the massage was so damn good he didn’t care.

“Spread your legs a bit?” Jason asked. Nate grunted, “Sure,” and Jason nudged them wider, kneading his thighs. “Towel okay to go?” Jason said. Nate paused, then mumbled, “Yeah.” It was off in a second, and Jason’s hands hit his ass—weirdly intimate, but fuck, it felt amazing. Fingers brushed his balls, and Nate’s dick stirred, pinned beneath him.

Jason moved to his back, strong hands working up his spine, cock nudging Nate’s arm as he stretched. Nate let it happen, sinking into the rhythm. Then Jason shifted to his head, massaging his scalp, and Nate peeked through the face hole—Jason’s lean thighs, trimmed pubes, thick cock dangling. It was… interesting.

“Time to flip,” Jason said. Nate rolled over, towel long gone, dick resting heavy on his thigh. Jason oiled his legs again, stroking slow, and Nate’s cock twitched, thickening. Jason’s hands grazed his balls, then his shaft, and Nate hardened more, a slick spot forming on his belly.

“Still good?” Jason checked. Nate just nodded, breathing harder as Jason teased his cock, brushing it deliberately now. Then up to his chest—Nate’s nipples tightened under Jason’s fingers, a jolt of heat hitting him. His hand drifted to Jason’s side, then his pecs, firm and smooth. “Feels nice,” Jason said. “You?”

“Real good,” Nate rasped, stunned by how much he meant it.

Jason’s cock—half-hard—slid against Nate’s ribs as he worked, and Nate’s hands roamed higher, thumbs circling Jason’s nipples. Jason moaned softly, and Nate’s dick throbbed, aching. From above, Jason teased his chest and belly, fingers wrapping around Nate’s cock, stroking slow. Nate gripped Jason’s hips, then his pecs, lost in it.

“Usually ends here,” Jason said, pausing. “But I’m good to keep going. Ethan said you’re exploring—want to push further?”

Nate’s pulse raced. He was rock-hard, turned on in a way he couldn’t dodge. “Yeah,” he said. “I wanna feel more of you—chest, maybe lower.”

“Perfect,” Jason said, climbing onto the table, straddling Nate’s waist lightly. His hands hit Nate’s chest again, and Nate’s landed on Jason’s—lean, warm, nipples stiffening under his touch. Jason oiled Nate’s palms, and he rubbed slow, Jason’s cock brushing his belly, hardening.

Nate slid his hands down Jason’s stomach—flat, tight—then grazed the base of his cock. It swelled, thick and cut, and Jason groaned, stroking Nate’s dick in return. Nate stared, that old curiosity roaring. Jason caught it, propped a cushion under Nate’s head, and shifted—his cock hovered inches from Nate’s mouth.

Nate’s lips parted, and Jason eased forward, letting Nate’s tongue flick the shaft. He licked—salty, alive—then Jason’s balls, heavy and smooth. Hands back on Jason’s chest, Nate teased his nipples as Jason moaned louder. The tip nudged Nate’s lips, and he opened, taking it in—big, stretching him, but he sucked, tonguing the underside.

“Holy shit,” Jason gasped, thrusting gently, eyes shut. Nate was gone—hornier than he’d ever been, feeding off Jason’s heat. The pace picked up, and Nate knew what was coming. He wanted it—wanted to know.

“I’m close,” Jason panted, pulling back. “Too much?”

“No,” Nate growled, raw. “Give it to me.” Jason slid back in, and Nate sucked harder, hands pinching Jason’s nipples. Jason braced above him, thrusts sharp, then froze—hot cum flooded Nate’s mouth, sharp and strange. He swallowed, reeling, and fuck, it felt right.

Jason eased off, catching his breath. “You okay?”

Nate nodded, dazed. “Yeah. More than okay.” For the first time, he didn’t push the feeling away—he let it settle, and it fit.

End part 1.

 

[kcdave]

Part 2.

Two weeks after that first massage, Nate found himself back at Jason’s door. The memory of that afternoon—Jason’s hands, his taste, the raw rush of it all—hadn’t faded. It clung to him, stirring something deep he couldn’t shake. He’d spent days wrestling with it: the straight guy he’d been for 50 years versus the man who’d swallowed Jason’s cum and liked it. He’d texted Ethan after, admitting, “You might’ve been right.” Ethan just laughed and said, “Told you. Go back if you want more.”

So here he was, heart pounding, knocking again. Jason answered, same easy grin, same gray robe, but now there was a knowing spark in his eyes. “Back for round two?” he teased, stepping aside. Nate kicked off his shoes, feeling less like a stranger this time.

“Yeah,” Nate said, voice rough. “Couldn’t stop thinking about it.”

“Good,” Jason replied, leading him to the familiar back room. The setup hadn’t changed—massage table, soft jazz, dim lights—but the air felt heavier, charged. They sat, and Jason leaned forward. “What’s on your mind this time?”

Nate rubbed his neck, hesitant. “Last time… it flipped something in me. I’m not running from it anymore. I wanna go further—figure out what I’ve been missing. Maybe… all of it.”

Jason’s grin softened. “All of it, huh? You mean bottoming?”

Nate’s face heated, but he nodded. “Yeah. Never thought I’d want that, but now I’m curious. Scared shitless, though.”

“Totally normal,” Jason said. “We’ll take it slow. I’ll walk you through it—same rules: you stop me anytime. Sound good?”

“Yeah,” Nate said, exhaling. “Let’s do it.”

Jason stepped out, and Nate stripped, climbing onto the table face-down, no towel this time. He was nervous but buzzing—his body already waking up. Jason returned, naked as before, and started with Nate’s calves, oil slicking his hands. The touch was familiar, grounding, and Nate sank into it. Up to his thighs, Jason’s cock brushed his feet again, and Nate let his toes curl around it, teasing back.

“Legs wider,” Jason murmured, and Nate spread them, ass exposed. Jason kneaded his thighs, then his cheeks, fingers grazing his hole—light, testing. Nate tensed, then relaxed as Jason poured more oil, circling slow. “Gonna start easy,” Jason said. “One finger—just breathe.”

Nate nodded into the table, and Jason’s fingertip pressed in, slick and warm. It was strange—tight, a faint burn—but Jason went slow, letting Nate adjust. “You’re doing great,” he said, sliding deeper, curling slightly. A jolt hit Nate, sharp and electric, and he gasped.

“That’s your spot,” Jason chuckled, working it gently. Nate’s cock hardened against the table, leaking already. A second finger joined, stretching him more, and the burn faded into something hot, needy. Nate groaned, pushing back without thinking.

“Ready for more?” Jason asked, pulling out. Nate lifted his head, catching Jason’s eyes—dark, hungry. “Yeah. I want you.”

“Flip over,” Jason said. Nate rolled, dick throbbing against his belly, slick with precum. Jason climbed onto the table, straddling Nate’s thighs, and grabbed a condom and lube from a side table. He rolled it on, slicked himself, then lifted Nate’s legs, resting them on his shoulders. “Look at me,” Jason said. “Breathe out when I push.”

Nate locked eyes, exhaling as Jason pressed against his hole. The head slipped in—fuck, it was big—and Nate clenched, breath hitching. “Relax,” Jason soothed, pausing. “Let me in.” Nate forced his body to loosen, and Jason slid deeper, slow, filling him. It burned, then bloomed into a heavy, pulsing fullness he’d never imagined.

Jason rocked gently, watching Nate’s face. “Good?”

“Yeah,” Nate rasped, stunned. “Keep going.” Jason thrust deeper, hitting that spot again, and Nate moaned, loud and raw. His cock twitched, untouched, as Jason built a rhythm—steady, then harder. Nate’s hands found Jason’s chest, rubbing his nipples, and Jason groaned, pace quickening.

It was overwhelming—pressure, pleasure, a stretch that turned into craving. Nate’s head spun; he’d never felt so open, so taken. “Fuck, Jason,” he grunted, hips tilting to meet him. Jason leaned down, kissing Nate’s neck, then his lips—first time for that too—and Nate kissed back, sloppy, desperate.

“I’m close,” Jason panted, thrusts sharp. “You?”

“God, yes,” Nate said, though he hadn’t touched himself. Jason gripped Nate’s cock, stroking fast, and the dual sensation—fullness inside, friction outside—snapped something. Nate came hard, cum spilling over Jason’s hand, his body shaking. Jason groaned, burying deep, and Nate felt him pulse inside, the condom catching it all.

They stilled, breathing ragged. Jason eased out, ditched the condom, and lay beside Nate, skin slick with sweat. “How you holding up?” he asked.

Nate stared at the ceiling, reeling. “Like… I just found a piece of me I didn’t know was missing. That was—fuck, life-changing.”

Jason grinned. “Glad to hear it. Takes guts to go there.”

Nate turned to him, voice low. “I’ve spent 50 years pretending this wasn’t me. Thought I was fine alone, straight, whatever. But this—this is real. I’m gay, aren’t I?”

“Sounds like you’re figuring that out,” Jason said. “No rush to label it, but yeah, feels like you’re home.”

Nate nodded, a weight lifting he hadn’t known he’d carried. “I wanna keep going—keep learning. With you, if you’re up for it.”

Jason’s hand found his. “I’m up for it.”

For Nate, it wasn’t just the sex—though that wrecked him in the best way. It was the unraveling of a façade he’d built since he was a kid, the one that said he didn’t need this, didn’t want it. Bottoming cracked him open, showed him desire he’d buried under decades of “shoulds.” He wasn’t just accepting it—he was chasing it now, hungry for more, and for the first time, he felt whole.

End.

 

[freakyretro69]

Nice work, great story.

 

[Man2kiss]

Part 2.

Two weeks after that first massage, Nate found himself back at Jason’s door. The memory of that afternoon—Jason’s hands, his taste, the raw rush of it all—hadn’t faded. It clung to him, stirring something deep he couldn’t shake. He’d spent days wrestling with it: the straight guy he’d been for 50 years versus the man who’d swallowed Jason’s cum and liked it. He’d texted Ethan after, admitting, “You might’ve been right.” Ethan just laughed and said, “Told you. Go back if you want more.”

So here he was, heart pounding, knocking again. Jason answered, same easy grin, same gray robe, but now there was a knowing spark in his eyes. “Back for round two?” he teased, stepping aside. Nate kicked off his shoes, feeling less like a stranger this time.

“Yeah,” Nate said, voice rough. “Couldn’t stop thinking about it.”

“Good,” Jason replied, leading him to the familiar back room. The setup hadn’t changed—massage table, soft jazz, dim lights—but the air felt heavier, charged. They sat, and Jason leaned forward. “What’s on your mind this time?”

Nate rubbed his neck, hesitant. “Last time… it flipped something in me. I’m not running from it anymore. I wanna go further—figure out what I’ve been missing. Maybe… all of it.”

Jason’s grin softened. “All of it, huh? You mean bottoming?”

Nate’s face heated, but he nodded. “Yeah. Never thought I’d want that, but now I’m curious. Scared shitless, though.”

“Totally normal,” Jason said. “We’ll take it slow. I’ll walk you through it—same rules: you stop me anytime. Sound good?”

“Yeah,” Nate said, exhaling. “Let’s do it.”

Jason stepped out, and Nate stripped, climbing onto the table face-down, no towel this time. He was nervous but buzzing—his body already waking up. Jason returned, naked as before, and started with Nate’s calves, oil slicking his hands. The touch was familiar, grounding, and Nate sank into it. Up to his thighs, Jason’s cock brushed his feet again, and Nate let his toes curl around it, teasing back.

“Legs wider,” Jason murmured, and Nate spread them, ass exposed. Jason kneaded his thighs, then his cheeks, fingers grazing his hole—light, testing. Nate tensed, then relaxed as Jason poured more oil, circling slow. “Gonna start easy,” Jason said. “One finger—just breathe.”

Nate nodded into the table, and Jason’s fingertip pressed in, slick and warm. It was strange—tight, a faint burn—but Jason went slow, letting Nate adjust. “You’re doing great,” he said, sliding deeper, curling slightly. A jolt hit Nate, sharp and electric, and he gasped.

“That’s your spot,” Jason chuckled, working it gently. Nate’s cock hardened against the table, leaking already. A second finger joined, stretching him more, and the burn faded into something hot, needy. Nate groaned, pushing back without thinking.

“Ready for more?” Jason asked, pulling out. Nate lifted his head, catching Jason’s eyes—dark, hungry. “Yeah. I want you.”

“Flip over,” Jason said. Nate rolled, dick throbbing against his belly, slick with precum. Jason climbed onto the table, straddling Nate’s thighs, and grabbed a condom and lube from a side table. He rolled it on, slicked himself, then lifted Nate’s legs, resting them on his shoulders. “Look at me,” Jason said. “Breathe out when I push.”

Nate locked eyes, exhaling as Jason pressed against his hole. The head slipped in—fuck, it was big—and Nate clenched, breath hitching. “Relax,” Jason soothed, pausing. “Let me in.” Nate forced his body to loosen, and Jason slid deeper, slow, filling him. It burned, then bloomed into a heavy, pulsing fullness he’d never imagined.

Jason rocked gently, watching Nate’s face. “Good?”

“Yeah,” Nate rasped, stunned. “Keep going.” Jason thrust deeper, hitting that spot again, and Nate moaned, loud and raw. His cock twitched, untouched, as Jason built a rhythm—steady, then harder. Nate’s hands found Jason’s chest, rubbing his nipples, and Jason groaned, pace quickening.

It was overwhelming—pressure, pleasure, a stretch that turned into craving. Nate’s head spun; he’d never felt so open, so taken. “Fuck, Jason,” he grunted, hips tilting to meet him. Jason leaned down, kissing Nate’s neck, then his lips—first time for that too—and Nate kissed back, sloppy, desperate.

“I’m close,” Jason panted, thrusts sharp. “You?”

“God, yes,” Nate said, though he hadn’t touched himself. Jason gripped Nate’s cock, stroking fast, and the dual sensation—fullness inside, friction outside—snapped something. Nate came hard, cum spilling over Jason’s hand, his body shaking. Jason groaned, burying deep, and Nate felt him pulse inside, the condom catching it all.

They stilled, breathing ragged. Jason eased out, ditched the condom, and lay beside Nate, skin slick with sweat. “How you holding up?” he asked.

Nate stared at the ceiling, reeling. “Like… I just found a piece of me I didn’t know was missing. That was—fuck, life-changing.”

Jason grinned. “Glad to hear it. Takes guts to go there.”

Nate turned to him, voice low. “I’ve spent 50 years pretending this wasn’t me. Thought I was fine alone, straight, whatever. But this—this is real. I’m gay, aren’t I?”

“Sounds like you’re figuring that out,” Jason said. “No rush to label it, but yeah, feels like you’re home.”

Nate nodded, a weight lifting he hadn’t known he’d carried. “I wanna keep going—keep learning. With you, if you’re up for it.”

Jason’s hand found his. “I’m up for it.”

For Nate, it wasn’t just the sex—though that wrecked him in the best way. It was the unraveling of a façade he’d built since he was a kid, the one that said he didn’t need this, didn’t want it. Bottoming cracked him open, showed him desire he’d buried under decades of “shoulds.” He wasn’t just accepting it—he was chasing it now, hungry for more, and for the first time, he felt whole.

End.

Amazing

 

[Hereforfun113344]

Ready for Pt 3, Bb