Jesse’s Encounters with Older Men

Jesse is 24, shy, a little soft around the edges, and hopelessly obsessed with older men. Two of his professors finally give him the attention he’s been quietly aching for.

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  • 1816 Readers
  • 2998 Words
  • 12 Min Read

Story Characters:

  1. Jesse, 24, shy, a little soft around the edges and still finishing his degree after a couple of years off. He kept to himself, head down but noticed everything when it came to older men.
  2. Professor Hale, late 30s, stood tall and precise, his frame trim and toned, sleeves always rolled to reveal strong forearms and a sharp, commanding presence.
  3. Professor Trent, early 40s, was heavier-built, thick through the chest and thighs, with a quiet, grounded authority that didn’t need to raise its voice.

Chapter 1: Between Professors

The lecture hall buzzed with quiet chatter. Students were settling in, notebooks flipping, laptop screens glowing, none of them noticing how still Jesse sat in his seat, tucked in the front row.

He wasn’t taking notes. He couldn’t.

Because Professor Hale stood at the whiteboard in a tight, pale blue dress shirt rolled up at the sleeves, talking with that low, resonant voice that rumbled through Jesse’s chest—and Professor Trent was seated behind the desk, one leg over the other, thick thighs stretching the fabric of his slacks, arms folded, eyes fixed not on the class, but on him.

“Now remember,” he said, voice low and smooth, eyes scanning the room but landing too often in one particular spot, “the tongue is a tool of persuasion. Whether you’re reading poetry… or delivering something much more personal.”

A couple of students laughed absently. Jesse didn’t.

He sat three rows from the front, jaw tight, thighs together, pulse ticking hard in his neck. He didn’t need to look to feel Hale’s eyes on him. The professor hadn’t stopped looking at him—not really—since the lecture started.

“Let’s talk about phrasing,” Hale continued, dragging the chalk down the board with a slow, deliberate curve. “Sometimes, it’s not what you say. It’s how you draw it out. How long you hold a syllable before you finally… let it go.” His eyes flicked to Jesse. “And how wet your mouth is when you do.”

Jesse’s breath caught. A low pulse of heat coiled in his belly, and he shifted slightly in his seat.

No one else reacted. No one else heard it.

Hale leaned on the desk now, fingers splayed. “A good speaker knows when to use pressure. When to push harder. When to keep their voice just barely above a whisper… right before they make you...feel something.”

Jesse’s cock throbbed in his jeans, shameful and half-hard. He didn’t dare look up.

“You with me, Jesse?” Hale asked, voice dipping.

“Yes, Professor,” Jesse mumbled, voice barely above a whisper.

“Good.” Hale smiled faintly, satisfied. “Some students just… absorb things better. Especially when they open up and really let it in.”

Jesse swallowed hard.

Trent adjusted in his seat. The chair creaked under his thick weight, and Jesse felt the shift of attention again—not just Hale’s, but his, too.

Eventually, the clock neared the end of the hour. Students began to stir.

Hale closed the book with a casual snap. “That’s all for today,” he said. Then, almost as an afterthought: “Jesse, please stay behind.”

The rest of the room filed out in lazy waves, chatter rising, footsteps echoing.

Jesse stayed seated. Frozen. Already half-exposed in his own skin. Hale hadn’t even touched him yet—and still, he felt undone.

“Close the door,” Hale said, once the last student left.

Jesse obeyed silently. When he turned around, both men were watching him.

“You were squirming in your seat the whole time,” Trent said, voice low, moving in closer. “I think someone liked being teased.”

Jesse’s voice was barely audible. “I did.”

“Speak up” Hale murmured, stepping behind him, his hand brushing down Jesse’s side. “You want this. Say it.”

Jesse swallowed. “I want it.”

“Are you sure?” Trent asked, stepping close. His thick hands cradled Jesse’s face like he was fragile and filthy. “You’ll be leaking for hours.” 

“And we want to make sure you want that,” Hale added, his chest pressing against Jesse’s back, thick arms wrapping gently around him. “Tell us. What do you want us to do?”

“I want to be used,” Jesse whispered. “Please.”

That got a growl from both men.

“Good.” Trent said, unbuttoning Jesse’s shirt slowly, eyes soft but hungry. 

“But we’ll take care of you,” Hale added, kissing the side of Jesse’s neck. “Every step. You just tell us if anything’s too much.”

Jesse nodded, already breathless. Jesse stood still between them—his shirt half open, breath shallow, heart thudding like a drum in his ears.

“Relax,” Trent murmured. “You’re safe.”

“You just tell us if you want to stop.” Hale added, kissing the curve of Jesse’s shoulder. 

“I don’t,” Jesse whispered, lips parted.

Trent smiled. “Good boy.”

He leaned in first, pressing his mouth to Jesse’s—slow, warm, deep. Jesse whimpered into it, melting forward, his hands hovering like he didn’t know where he was allowed to touch.

Behind him, Hale’s hands slid down Jesse’s sides, steady and large, then under his open shirt. His palms found Jesse’s soft chest, thumbs brushing his nipples gently.

Trent leaned back. “You’re beautiful.” he said against Jesse’s lips.

Hale’s hands didn’t leave Jesse’s chest. He kept rubbing slow, circular motions over his nipples.

Jesse’s breath hitched. His hips rolled forward involuntarily, pressing into Trent’s thigh.

“See?” Trent chuckled. “Your body already knows how much it needs this.”

Jesse whimpered. “Please…”

Hale kissed the back of his neck, then bit gently just below the ear. “Please what?”

“Please give it to me.”

That did it.

Jesse was trembling as he dropped to his knees between them, his shirt forgotten on the desk behind him, chest flushed, cock aching untouched.

Hale and Trent stood tall in front of him, still mostly dressed—slacks straining, sleeves rolled, shirts tight across their broad chests. They looked down at him like he was theirs already.

He was.

“You want this?” Hale asked, brushing hair from Jesse’s forehead.

“Yes, daddy,” Jesse whispered, eyes flicking between their bulges.

Trent smiled. “Then take your time. We’re not going anywhere.”

Jesse’s hands were unsteady as he reached up, fingers working open Hale’s belt first. The professor’s cock sprang free, thick, flushed, already leaking. Jesse licked his lips instinctively.

“God, look at you,” Hale murmured, stroking Jesse’s cheek with the back of his knuckles. “Already drooling.”

Jesse leaned in and took the tip into his mouth—slow, reverent, sucking gently while looking up for approval. Hale hissed in through his teeth.

“Good boy.”

Jesse moaned around him.

He sucked deeper, gradually working more of Hale’s cock into his throat, letting it stretch him open. He gagged once—then stilled, adjusted, relaxed. Hale’s hand settled on his hair, steady and warm.

“You alright, sweetheart?”

Jesse nodded, mouth full, and gave another slow suck that made Hale grunt low.

“You’re a natural,” Trent murmured behind him. “But don’t hog him.”

Hale chuckled and pulled out, wet and glistening. Jesse immediately turned toward Trent, pupils blown wide. 

Trent’s cock was thicker, curved, the head flushed dark. Jesse licked from base to tip before wrapping his lips around it and sinking down as far as he could.

He whimpered.

“That’s it,” Trent breathed. “Get messy with it. You like how it stretches your throat?”

Jesse nodded, choking gently as Trent fed him another inch, hand on the back of Jesse’s head, guiding but not forcing. “You can stop any time. But you don’t want to, do you?”

Jesse pulled off just long enough to pant, “No sir.”

Then he dove back in.

They let him work—switching back and forth, mouths wet, cocks slick with spit, Jesse’s lips red and raw and glistening. His own cock throbbed untouched between his thighs.

Eventually Hale crouched beside him, rubbed his back slowly.

“You’re doing so good,” he murmured, kissing Jesse’s shoulder. “But now I want to taste you.”

Jesse blinked up at him.

Trent stepped back and pointed to the desk. “Bend over, baby.”

Jesse obeyed instantly, climbing onto the desk on shaky limbs. He spread his legs, chest to the cool wood, ass arched high. His hole twitched in the air—puffy and wet from need.

“You ready?” Hale asked, brushing a thumb across his rim.

“Yes. Please.”

Trent leaned in first—licking a long, slow stripe from Jesse’s balls up over his hole, then circling it, gently spitting, then licking again. Jesse cried out, the sound sharp and desperate.

Hale followed—tongue firm, spreading him open, tasting deep, groaning into the slick.

“Fuck, you taste good,” he said. “Could eat you all day.”

Their tongues alternated—licking, probing, sucking at his entrance until Jesse was sobbing into his forearm, legs shaking violently.

“please I’m gonna—I’m gonna cum—!”

Trent pulled back just in time, breath hot against his skin. “Not yet. Not without our cocks inside you.”

Jesse whimpered like it physically hurt to stop.

But Hale kissed his lower back and said gently, “You’re doing so good. Still with us?”

Jesse nodded hard. “I want it. Please. I want to be filled.”

Both men stepped back.

“Then beg for it,” Trent said, unbuckling his slacks fully.

Jesse looked back over his shoulder—eyes red, mouth open, hole twitching.

“Please. Fuck me. I want to be your good boy.”

And that’s exactly what they were about to give him.

Jesse’s breath caught in his throat as Trent moved behind him—his large hands gripping Jesse’s hips, guiding them upward, spreading him wide. The air was cool on his wet hole, still slick from both their tongues.

Then he pushed in.

Jesse gasped—his whole body tensing as Trent’s thick cock slid slowly, achingly deep, stretching him wide. There was pain, yes, but underneath it… the overwhelming fullness. The delicious surrender.

“Breathe,” Hale whispered from in front of him. “Breathe through it. You’re doing so good.”

Jesse nodded, eyes fluttering, and let out a broken moan as Trent bottomed out.

“Fuck,” Trent groaned. “So fucking tight. Like you were made for this.”

He stayed still a moment—letting Jesse adjust, hands rubbing slow circles on his back.

“You want more?” he asked.

“Yes, daddy,” Jesse whispered. “Please move.”

Trent began to fuck him—slow, deep thrusts that rocked Jesse’s whole body, pushed him forward into Hale’s arms.

Hale caught him gently, cupping Jesse’s cheeks, tilting his head up. “Open your mouth, baby.”

Jesse obeyed without hesitation.

Hale slid his cock past Jesse’s lips, filling his mouth just as Trent was filling his ass. Jesse moaned around the length, overwhelmed and starving for it. His throat relaxed, drool spilling down his chin.

“That’s it,” Hale murmured. “Just like that. You take cock so beautifully.”

Jesse could barely think.

Trent fucked deeper, firmer, hips slapping now with each stroke. Hale guided his mouth down his shaft, slowly, praising every swallow.

“Don’t forget to breathe,” Hale murmured between thrusts. “Relax. We’ve got you.”

Jesse moaned again—his body stretched from both ends, used, worshipped, filled.

Eventually, Hale pulled out, gently wiping the spit from Jesse’s lips.

“I want to see your face while he fucks you,” he said.

He moved beside the desk, one hand stroking Jesse’s cheek, the other rubbing his back as Trent kept thrusting deep, cock grinding into that soft spot that made Jesse cry out.

“Look at me,” Hale whispered. “You still doing okay?”

Jesse looked up at him, eyes glassy. “Yes. Please don’t stop.”

Trent grunted behind him, thrusts quickening. “Fuck. This little hole—you’re milking me, baby.”

“Yes,” Jesse sobbed. “It’s yours. I’m yours.”

Hale kissed Jesse’s temple. “You want him to fill you?”

Jesse nodded, his cock untouched but twitching. “Yes, daddy. Please.”

Trent’s pace grew ragged, breath hard in his throat as he slammed into Jesse’s ass, now stretched slick and pulsing around him.

Jesse couldn’t breathe right. Couldn’t think.

Hale was at his side, cradling his jaw, kissing him through the tears of pleasure streaking his cheeks.

“You’re taking him so well,” Hale murmured, brushing Jesse’s hair back. 

Jesse started trembling, voice shaking. “He’s—he’s so deep—it’s too good—I’m gonna—”

Jesse cried out.

His untouched cock twitched once—twice—and then he came hard across the desk, his body convulsing as Trent groaned loud behind him.

“Oh fuck—fuck—take it—take all of it—” Trent growled, hands tight on Jesse’s waist as he pushed in deep and spilled inside him, thick spurts flooding Jesse’s clenching hole.

Jesse moaned through it, helpless, broken open, tears streaking down his face.

And then it was soft again.

Trent pulled out slowly, breathless, hands gentle now. He bent down, kissed the small of Jesse’s back.

“You alright, baby?” he asked softly.

Jesse nodded. “Yeah. I just… I feel so full.”

Hale laughed and kissed his forehead. “That’s because you are.”

They didn’t rush. Trent helped Jesse reposition—gently laying him on his back atop the desk while Hale undressed fully, his cock already thick and aching.

Then he climbed between Jesse’s thighs and leaned in.

Jesse reached for him. “I want you, daddy. Please. I want you to fill me next.”

Trent chuckled from the side, brushing Jesse’s hair back. “Our insatiable little slut.”

Hale smiled and lined up. “Then open up for me.”

He pushed in.

Jesse gasped again—still sensitive, still slick—but his body welcomed Hale’s cock with a slow shudder. Hale was slower than Trent, deeper. He moved with slow, grinding thrusts that rubbed everything. Each motion made Jesse’s legs shake.

Beside him, Trent sat on the desk and caressed Jesse's face “You’re doing so fucking good. You’re taking daddy’s cock like a trained slut.”

“Like our boy,” Hale added, driving in deeper, panting now. “God, you feel fucking perfect.”

Jesse moaned, turning his face into Trent’s hand. “Don’t stop. I want it again.”

“You’ll get it,” Hale promised, fucking harder now, sweat dripping onto Jesse’s chest. “You’ll get every drop.”

Trent kissed Jesse’s cheek. “Look how wrecked you are. And still begging for more.”

“I can’t help it,” Jesse whimpered. “I need you both.”

“Then you’ve got us,” Hale growled. “You’re ours now.”

His rhythm snapped—deep, firm, final strokes—until his whole body tensed and he groaned loud. “Here it comes, fuck—fuck—” Hale moaned, his cock pulsing as he filled Jesse’s sore hole, adding to the mess Trent left inside.

Jesse was nearly delirious.

Hale collapsed onto him, breathing hard.

The classroom was quiet now, dim and hazy with sweat and heat.

Jesse lay on the desk, legs still trembling, hole leaking—thighs sticky with a mix of both men’s cum. His hair was damp, cheeks flushed, chest heaving.

Trent stood nearby, already buttoning his shirt halfway, sleeves rolled up. Hale remained at Jesse’s side, shirt fully undone, skin slick, his hand stroking Jesse’s arm slowly.

“You still with us?” Hale asked softly, brushing Jesse’s lips with his thumb.

Jesse blinked up at him and nodded, voice raw. “Yeah. I’m… I’m good. Really good.”

“You liked getting passed between your daddies?” Trent asked. “Filled up like a toy?”

Jesse turned his head toward him, still smiling. “Loved it.”

Trent chuckled. 

“Good boy,” Hale murmured, kissing his forehead. “But let’s clean you up first, yeah?”

They moved gently, carefully—wiping him down with tissues and warm water from Hale’s thermos. Every touch was reverent.

“You took us so well,” Hale said. “So fucking proud of you.” Jesse flushed and bit his lip.

Trent between his thighs, gently spreading him to wipe the leaking cum from his sore hole.

Jesse noticed the glistening dicks that were near him. “I... I want to” Jesse said, voice small. “I want to taste it. All of it.”

Hale raised a brow. Jesse looked between them, eyes wide and wet.

Trent exhaled smiling.

“Daddy’s good boy.” Hale added.

“Here, clean daddy off.” Trent ordered, stroking Jesse’s hair.

Jesse crawled closer and took him in, gently licking up every drop of his own spit and Trent’s cum, slow and devoted like it was a ritual. When he finished, Hale had him do the same—tongue working over both shafts like he needed it.

Then Trent held his fingers up. “Open up.”

Jesse obeyed. He sucked Trent’s fingers into his mouth without hesitation, moaning at the taste—the salt, the heat, himself in the mix. Hale watched, stroking Jesse’s soft chest, thumbing over a sensitive nipple.

“Look at you,” he murmured. “Our soft little cumslut.”

Jesse whimpered, cheeks pink, cock twitching again. “I love it. I want more.”

“You’ll get more,” Trent promised. “You’ll get all of it. Again and again.”

“Such a good boy,” Hale said, pulling Jesse into his arms now, cradling him. 

“I’m yours,” Jesse whispered. “I don’t want to be anything else.”

They held him close—Trent stroking his hair, Hale kissing his temple.

Jesse was still nestled in Hale’s arms, his breath slowing, his body loose and leaking, when the door creaked open.

All three of them froze.

In the doorway stood a tall figure — mid-fifties, stern-faced, sharp suit, silver at the temples. The air shifted instantly.

Jesse turned, eyes wide, panic flaring in his chest.

“D-Dean Mercer,” he choked out, scrambling to cover himself, his thighs still sticky, lips red, hair damp with sweat.

The dean surveyed the scene.

Hale half-dressed, holding Jesse like a spent lover. Trent standing beside them, arms crossed, wet fingers drying on a tissue.

Dean Mercer raised an eyebrow.

“Finished without me, did you?” His voice was calm. 

Jesse froze, confused. “I—wait, what—?”

The dean stepped inside, closing the door behind him with a soft click.

“I told you boys I’d be out of the meeting early today,” he said, undoing a cufflink. “No matter. I’ll simply join earlier next time.”

Jesse blinked. “Next time…?”

Mercer smiled faintly. “Of course. And if you ever get bored of these two,” he added with a gesture to the professors, “my office is always open.”

Trent chuckled, stretching. “Careful, sir. You’re going to spoil our favorite toy.”

Hale kissed Jesse’s cheek again. “Don’t worry, baby. You’ll have options.”

Jesse lay back, flushed and leaking, his breath slowing but his mind was already drifting.

How many other men were still in the building, how many more cocks he could take. He’d just have to find out.


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If you enjoyed this story, send me an email at [email protected]. I'm thinking about turning this into a series, and a little encouragement (or some teasing) might be all it takes. Tell me your favorite part, or what you'd love to see next.

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