Cum and Ass, Creepypasta Book of Smut (REQUESTS OPEN)

Jeff the Killer solo

Contains: first time masturbation, mentions of self harm, violence, some background
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It's hard being a killer with a fucked up face. Jeff was beautiful, he didn't regret his decision ever. However he wish it weren't so permanent. Like you know, he wishes it healed over every one in a while.

Jeff had given into his insanity by the ripe age of 13. That's when your life really starts. Well, it really started for him. But that also meant he never got the physical affection like a regular guy does. He never experienced a first kiss, he didn't even jack off. There was no way he could have sex. He may be crazy but he isn't crazy enough to rape anyone. He still has morals. Just not much.

Lately he had been messing up with his work, his cuts sloppy and his stamina more depleted than usual. Everyone noticed this, even police.

"You can't be trusted out anymore. Until you prove that you get out of this little phase you're in, the boss doesn't want you out."

"You can't fucking do that! You don't own me, I want the tall asshole to say it to my face!"

Masky pulled out his pistol and pressed the muzzle to Jeff's temple, his finger tightly wrapped around the trigger. This stopped the scarred boy, his knuckles turning white from how hard he gripped his knife.

"These are words from him, you will do well to obey them otherwise I won't hesitate to shoot your fucking brains out kid." Jeff immediately stood down. It's not like he could stay dead. After a while he'd come back. But it didn't mean death wasn't a horrible experience.

"Fine, I want you and your stupid gay boyfriends to leave me alone then. I'm tired of being monitored, I'm practically an adult."

"Okay, whatever you say mr 'I fucked myself up at thirteen and now I'm nineteen and still a virgin'." Masky put his gun away but Jeff made a quick jab to his jugular. If he ran fast enough, he'd escape his doom.

So he bolted away from the masked man.

Once safely in the comforts of his own room, he paced and listed all the possible reasons he's losing his edge. Maybe it's too familiar? No, that would mean he's just naturally good at it at this point. Maybe he isn't motivated? Oh, maybe that's it.

While he was pacing, he noticed another problem occurred. Within his somewhat skinny jeans, a bulge started to form. That was one problem that kept popping up, within a lot of his recent killings he's been popping a boner. Nothing caused this. Nothing that he could think of. Maybe a friend of his would know.

So off to BEN's room he went. He didn't even bother knocking on the door, just barging in and shutting it behind him.

"Dude! Can you not act like you own the place? I could've been naked."

"Your small elvish body doesn't appeal to me. I need help."

"Yeah yeah I bet yo- WOAH THERE! What the fuck are you doing?! You just said I'm not hot!"

"Because you aren't! I am hard and don't know why and I need help to get rid of it!"

The room was awfully silent afterwards. Jeff was flushed red by admitting something like this but it's not like arguing would get it to go away. In all honesty, he wasn't really embarrassed about not knowing what to do. He had strange parents and his brother never did anything that he didn't know about, plus his friends were limited. So jacking off was one thing he never actually did. All he knew was that a cold shower usually shooed away the foreign feeling in between his legs.

BEN just stared in shock. It looked like they were starting to drool before they spoke.

"Do you really not know what to do?" Jeff shook his head and took a seat beside the Link lookalike on one of the bean bags. "Um, do you ever actually touch yourself?"

"Not unless I shower or have to piss, but that's it." BEN was dumbfounded. How could this guy really be this stupid? They cleared their throat before grabbing their phone.

"I'm going to send you a link to something real quick. You should uh, go based off of that okay?" Jeff nodded and got up, heading back to his room a little more hopeful this time. His phone chimed once he got to his room, the door locking behind him just in case.

BEN had texted him the basics of masturbation. His exact texts were "hand on cock, keep stroking till you bust." Bust what? Stroke how? And what the hell did they send him?

He turned the volume down to his phone all the way as he watched this strange video of whatever the fuck he was sent. He felt it was worsening his erection for it only got bigger.

"I'm going to regret this."

He inhaled sharply before slowly undoing the buckle to his belt. He fumbled nervously with the zipper and button of his pants, slowly pulling his pants and boxers down his thighs halfway. It felt so strange to want to touch yourself. He found his skin disgusting after the burn. It felt like leather, each cut to his skin never feeling deep enough. So he found even looking at himself in the mirror gross if it wasn't his face.

Jeff let out several shaky breaths as he wrapped his warm sweaty hand around his erection. It was a strange sensation already, his body jolting at the touch. Suddenly the room felt too hot.

He slowly slid his hand up and down his shaft, the tip leaking out pre-cum which made it easier when he spread it out. The tip felt so much more sensitive, a sharp almost wince coming from him as he experimentally pressed his thumb over the slit. It didn't take long for him to spill. After all, that was years of being pent up, not even a wet dream to spare him.

When he felt it happening, his jaw locked up and his free hand gripped the headboard tightly. It seemed like his eyes got even wider as a strangled noise came from his throat. He was on the verge of tears when it ended. It felt euphoric, but it also hurt. He needed to get more of this pent up frustration out, he would kill to get it out.

So for the next hour, he made sure to work himself until he was empty, his cock so overstimulated but his satisfaction overpowering the physical feeling.

It didn't take long to shower, the urge to get to bed and pass out was so overwhelming. BEN had been watching after Jeff went out his room, their eyes following his every move until he got back into his room.

His little time off was short lived as the Operator realized that he was doing much better than before. Jeff didn't mind, he was glad. At least once a month, he made sure to take time to himself to sort out his "problems" which helped. What didn't help was BEN constantly pestering him.

"You really need to lose your virginity, it's kinda sad you're this old and haven't gotten any game."

"Well if you couldn't tell, I'm also really terrifying for others to look at. I disgust more than half of the others and they've seen some pretty fucking disgusting things." Jeff huffed as he laid on the ghost's bed. BEN hummed in response, forgetting about his face. They thought he looked fine, but they were also into weird things.

The only person that was willing to screw the guy was Lulu, but she was never around much so it didn't matter.

"Have you tried other things? Like fingering yourself? Should I get you some shit to satisfy yourself?"

"Stop it freak, I'm not into you like that." BEN smiled mischievously and leaned over the scarred man, their face awfully close to Jeff's.

"Come on, I can help you out. I already know what you like. How about I leave you on the verge of death while blowing you? It would be an experience."

Suddenly, Jeff wasn't so sure about his feelings for the ghost. They weren't fully wrong. Even he has experimented. The feeling of his skin being damaged while he gets off was amazing. He always enjoyed pain, he hurt himself just so he could feel pain. He was a very sick man, but BEN made him feel insanely worse.

He wanted to say yes.

So what was keeping him from doing so?

His morals. He may be 19, but that means nothing when the boy was 17. He didn't care how much they begged, not until he was 18.