Creepypasta One-Shots

Trenderman X Assistant Y/n

(Requested by DrakensDoormat)

Y/n had been wanting to become a tailor or just someone who is involved with fashion clothing. So, they turned to Trenderman. After the interview, he accepted them as his assistant.

Many months go by, Y/n was the best assistant Trenderman has ever had in his years of living. He was really pleased by their work.

One day, Trenderman was sitting in his office going over a few things with a client. Unbeknownst that Y/n was under his desk... until he looked down.

As the client looked at their papers and wasn't paying any attention to Trenderman and saying what ever was on the papers, he whispered to Y/n.

"What the fuck are you doing?!" he whispered to them, suddenly looking up at the client and speaking in his usual tone. "Could you repeat that? I didn't quiet catch it."

Trenderman's attention was now on the client. Y/n was playing with his belt buckle. He kept batting their hands away.

Until they successfully unbuckled his belt and took it off. He sighed and chose to ignore them and focus on the client.

He felt them slide off his pants. Now that his bottom half was exposed to the cold air, he still remained focused.

That was until Y/n kissed the tip of Trenderman's cock. It caused him to let out a whimper. The client stopped and looked at him.

"Are you alright?" they asked.

Trenderman cleared his throat and put his hand over where his mouth would be, "Yeah, I'm fine. Just needed to sneeze."

The client slowly nodded their head as they went back to discussing the papers. Y/n smirked when they were able to get a reaction out of Trenderman.

As they wrapped their hand around his member, it twitched in their hand. He was tempted to give their position away but decided against it. He'll punish them later.

After the client left and closed the door, Trenderman grabbed Y/n and pinned them to his desk, making them gasp.

"You have a lot of nerve doing that," his voice low as a warning.

They gulped, "L-Listen, I thought it would be a funny joke. I'm sorry-"

They were cut off by him turning them around and having their chest pressed against the desk. One of his hands held down their wrists while the other began to slowly undo their pants.

"A joke? You call making me half-naked and kissing my cockhead in front of a client a joke?" He said as he pulled down their pants.

"They didn't know that was happening-" they were cut off again by him pulling on their hair, making them mewl in response.

"I don't care," he said harshly. "Now, because of that little stunt, I'll be making sure to punish you thoroughly."

He spanked their ass, making the skin jiggle and making them whine. He took off their underwear before spreading their ass cheeks open and exposed their puckered hole.

They let out a gasp when he did so. Without warning, he thrust into him, his member going through the tight ring of muscle.

They let out a cry as he did so. Without waiting for them to adjust, he went at a torturing pace. His hips snapping forwards as he pounded into them with abandon.

Trenderman hissed as he pressed his chest against Y/n's back, still pounding into them. "Don't think I'm going to stop when you're screaming my name or begging for mercy," he growled. "I'm going to fill up your slutty holes until you learn not to do it again."

They couldn't help but let out a series of moans and whimpers from the fast and hard pace. They nodded their head in understanding through their noises they were making.

He let out another growl and, if he even can, went even faster. A loud and sharp cry tore from their throat. They could feel themself getting closer to a climax.

"Ah! Trender! I'm close!" They moan.

"Cum for me, you slut," he demanded, feeling his own climax coming to its peak since he felt his balls tighten.

After one final brutal thrust, a sharp cry tore from Y/n's throat once more as they came undone. Trenderman did one more brutal thrust as his hot seed spilled deep inside them.

He panted for a bit before withdrawing from them. He spun them around and pinned them on their back. "Get ready for round two."