Professor Grayson's Favorite sin

LENNON 

Lennon kept telling himself it was for research purposes.

Just one anonymous, filthy, no names night to prove–to no one in particular– that the thing clawing at the inside of his skull every time professor Grayson so much as looked in his direction was just stress. Just a weird phase.

Because Lennon Kessler was straight. Straight guys didn’t get hard in lecture halls when a man twice their age said “good” in that low, approving voice. Straight guys didn’t jerk off three times a night picturing that same man pinning them down and ruining them.

So he downloaded the gay app everyone whispered about: Velvet heat. If the black icon wasn't enough of a red flag, then the fact that it was invitation-only would have told literally anyone to turn around and never look back. But Lennon wasn't going to do that. 

It took him two whole weeks to get the invite code from his best friend –Archer Reeves. How Archer got the code was a mystery he had no zeal in solving. The guy was a f*cking enigma.

When the app finally unlocked, the profile questions made Lennon's palm sweat.

Orientation?  

He clicked “curious.”  

Experience level?  

Virgin.  

Hard limits?  

He filled in none. 

Kinks?  

He paused at that, his heart hammering.

Did he have kinks? Could he just uninstall the app and forget he ever thought about this?

No, he wasn't going to back out now, not after promising to do Archer's homework for the rest of the school year.

One by one, he selected everything. Every single taboo box. Age gap. Blindfolds. Degradation. Ownership. Breeding. 

The little red warning popped up: EXTREME MATCH ONLY. He clicked confirm before he could chicken out.

Username: prettyboy21.

Profile pic: an over the top, seductive picture of his mouth, glossy and bitten red.

Then the matching began, after a few seconds the result came. He matched with only one person.

Username: Obsidian.

No photo, age or bio.

A shiver ran down his spine. Was he really about to match a stranger who could be a serial killer or worse, someone that knows him. Lennon didn't know which scenario was worse.

No, nope. He wasn't going to risk it either. His fingers hovered above the “return home" button but before he could click it, the app's message icon showed that he had received a text.

In that moment, Lennon felt his stomach drop. Fear and something else coursed through him. Anticipation.

His finger shivered as he opened the message that had come from none other than Obsidian.

Friday. 11pm. The black orchid. Wear nothing underneath.

The black orchid was the official club where everything went down. At least that's what Archer had told him.

He stared at the message for a good thirty minutes, running down every possible bad thing that could come out of this. The worst being his dad finding out. He shook his head. No, that was his intrusive thoughts speaking, his dad could never find out.

He was going to do this. Just once and he'd put it behind him.

Somehow, he didn't believe his own thoughts.

Friday night, he showed up practically shaking. Hoodie pulled low and palms sweaty against the buzzer.

A petite woman whose face was covered in a porcelain mast opened the door. 

“Name?” the woman asked, her voice surprisingly clear behind the mask.

“P.. prettyboy21," he whispered, cheeks on fire.

"Welcome sweetheart. Follow me." 

She led him deeper down the hallway and past a larger space that was illuminated with red lights.

Lennon felt it was a bit cli ché but kept his thoughts to himself.

He didn't notice the woman stop and almost ran into her.

“Please change into these," she handed him a silk, soft black shorts that would barely cover his ass. But that wasn't what bothered him. He stood there, unmoving and red from embarrassment.

“Could.." he stuttered, “Could you turn around? I'm not wearing anything underneath." He added the last part then bent his head in shame.

Lennon didn't want to admit it, but he just loved following orders and he didn't want to end up being punished for something as stupid as wearing underwear. He just wanted the night to be over.

Blood rushed to his ears and he immediately wished he hadn't come.

The woman's eyes brightened behind the mask then she turned. Lennon could practically see the smirk on her face.

He put the shorts on quickly as if his ass was on fire then cleared his throat to tell her he was done. 

The blindfold came next, thick and soft, plunging him into absolute darkness. Then a leather cuff was clipped around his wrist. 

“Walk ten steps then stop. Have fun!" The woman's voice came from behind him.

It seemed that having his sight taken away heightened every other of his senses. His brain registered the faint scent of cedar and.. sex. He heard a door open and close.

This was his idea. All he had to do was take ten steps and the night would begin. The sooner it started, the sooner it would be over. Right.

He internally shook his head, he didn't have the time to think. His match was probably waiting for him in there. He didn't want to keep the guy waiting.

He began walking. One step after another. Each step felt heavier than the last, and his heart just wouldn't stop pounding against his rib cage.

The moment he stopped, he felt a pair of hands close over his hips. From behind. Obsidian. 

He guessed the guy would either be in his late thirties or early forties. 

A body pressed against his back, the ridge of his hard cock lining his ass crack, grinding slowly against him. 

Obsidian was not a small man.

Lennon felt his own dick strain against the shorts.

Hot breath fanned the shell of his left ear. “On your knees, pretty boy." 

He dropped instantly, his knees hitting a thick rug. 

The voice alone made pre cum soak the front of the silk shorts. The voice was familiar, but he couldn't remember where he'd heard it from. It also didn't help that his brain was short circuiting every twenty seconds from pleasure. His whole body felt like a live wire.

A thumb traced his bottom lip then pushed inside. “Suck." 

He opened obediently, tongue swirling around the intrusion like he’d done this a thousand times instead of never. The man hummed, pleased, and fed him two more fingers, then three, until Lennon was choking and drooling and humping the air like a desperate animal.

“You're such a good boy. And good boys get rewarded." 

The fingers vanished, a belt buckle clinked, zipper pulled down. Then the wet head of a cock painted his lips, smeared across his cheek and left a trail of pre cum.

Lennon opened his mouth and took it to the root in one slide, gagging hard enough that tears soaked the blindfold.

The man fucked his throat without mercy, one hand fisted in his hair, the other gripping his jaw to feel himself bulge beneath the skin. Every time Lennon tried to pull off for air, the hand yanked him back down until his nose was buried in trimmed hair and his throat spasmed around the intrusion. When he finally came, it was sudden and brutal, thick pulses straight down Lennon’s throat while the man growled, “Swallow every drop, pretty boy.”

Lennon came as well in that instant without being touched. He was crying and shaking and riding the aftershocks of the most mind-blowing orgasm he's ever had.

The man hauled him up by the cuff, spun him, bent him over, something padded, and ripped the shorts down to his thighs.

“You didn't wear any underwear did you?”

Lennon shook his head, then hissed when the man slapped his bare ass, making fire course through him.

“Use your words!” Obsidian practically growled in his ear.

“Y..yes. I mean, no. I didn't wear anything asides my pants.” His voice shivered.

The man kneaded his ass in a gentle massage that soothed him. “Good.”

Cold air hit his hole, then a tongue speared inside him in a slow and deliberate thrust that had him seeing stars. Lennon screamed into the rug, hips jerking as he tried to get away and get closer at the same time.

Fingers followed the tongue, first one then two and then it was three, scissoring roughly into him, spreading him. He felt something wet on his ass, then realized that it was lube. When Obsidian reached for the lube he did not know.

A hand cracked across his ass hard enough to leave a print. Again and again. Until he was sobbing.

“Please,” he sobbed, “please, I can’t—”

“You can't what?”

“I can't take it anymore!”

“What do you want, Pretty boy? Tell me what you crave right now.”

“Fuck me. Please. I need your dick in me right now.”

“You were such a good boy tonight. So I'll reward you.”

The blunt head of Obsidian’s cock pressed against his hole and pushed in slowly.

Lennon wanted to scream. It hurt so bad and felt so good at the same time.

One brutal thrust and he was split open. The burn was hot and perfect. The man didn't wait, just gripped his hips hard enough to bruise and fucked him like he was trying to carve his name inside Lennon's body. 

Every thrust punched a broken sound out of him. The angle shifted and Lennon came again untouched, clenching so hard that the man cursed and sped up. 

“Mine,” The man snarled against his ear, teeth sinking into his shoulder. 

“Say it.” 

“Yours,” Lennon slurred. “Only yours, sir.”

“Lennon,” The man roared as he slammed into the roots and flooded him. Pulse after pulse of cum. He kept moving with smaller thrusts, milking every drop until Lennon was sobbing from overstimulation.

Slowly, Lennon’s senses returned and it hit him. 

Lennon.

Obsidian had called him Lennon. He hadn’t imagined it. He wasn't so cum drunk that he'd imagined it.

Obsidian knew who he was. And he probably knew Obsidian too.

Before his brain could catch up, he said, “How do you..”

He didn't get to finish his sentence, Obsidian, who had remained buried inside him after he came and was probably catching his breath, immediately rose and pulled out so fast. Lennon felt the cum drip down his thigh, and in an instant, it felt like he was alone in the room.

It was all happening so fast and it didn't make sense to Lennon. Who was this guy? Where did he know him from? Had he known it was Lennon before he matched him? Was that even possible?

Ten minutes later, his blindfolds were taken off. It took his eyes some time to adjust to the light, and when it finally did, he noticed that the room was softly illuminated with blue lights. And his clothes were lying right next to him, along with a note that said, “twenty steps to your right and walk back the way you came

." That was it.

He dressed up quickly and did as he was told. He still had that nagging feeling that something was very wrong. 

And this wouldn't be the last time he would encounter Obsidian.