Will Cipher x Dipper Pines One-Shots Collection [Requests Allowed]

Stalker AU - Smut

{SMUT WARNING}
(The title should have said that for me.)

   It was the 50th night since Dipper had been visiting. He and Will got together on the 23rd night. If you did the math, they have been together for a little more than a month now.

Dipper climbed through the window yet again. Will smiled and greeted him. They hugged and sat down on the bed. Will sat down on Dipper's lap. "Anything special planned, or are we just gonna cuddle like last time?," he asked. Dipper laughed lightly. "Do you want to do anything else?" Will couldn't help himself. "No, I only want to do you," he joked. Dipper went red. Will laughed. Dipper pushed him off laugh and yelled, "You little bleep!" Will snorted. "Bleep?," he teased. Dipper glared at him. "You say you want to...'do me'?," he asked to change the subject, tilting his head to the side. Will blushed and looked off to one side. Dipper got off of the bed and pulled Will to his feet. "You can if you want," he told Will, "Just don't go doing things you don't like." Will blushed even darker. "U-Uh..." "I said it was okay if you don't." Will shook his head. "No, it's fine." Dipper's eyes widened. "Wait, really?" Will began to nervously rub his hands together. "Well, yeah, I mean... we have been together for a while now," he explained. Dipper snapped out of his staring. "Oh, umm... Okay, then... How are we going to be doing this?" Will laid down on the bed. "You be dominant." Dipper pointed to himself wearing a surprised expression. Will nodded his head.

   Dipper gulped before climbing on top of Will and pinning him down. He hesitated for a moment before leaning in to rest his lips on Will's collarbone. He kissed along it before finally biting down and sucking. Will gasped, not expecting him to do that. Dipper kissed his cheek and asked permission to go further. Will smiled and rolled his eyes. He nodded and waited for Dipper to gain up the courage to take it further. Dipper finally leaned down to kiss Will, the kiss deepening as he slipped his tongue into Will's mouth. Will was completely submissive, going along with whatever his lover decided to do. Dipper began to lift up Will's shirt. He pulled away from the make-out session and removed the shirt, throwing it off into the corner. He stared at Will for a moment before looking at the door with an uncertain expression. Will understood this and said, "I've already locked the door. Bill's out with another one of the poor souls he's decided to play, and my parents haven't been home for a while. I think they're on some sort of trip." Dipper looked back at Will, still looking uncertain. "How... How far will this go?" Will shook is head. "I've already prepared some things in case we went that far." Dipper almost laughed out loud. "You were expecting this, huh?" Will blushed. Dipper gave him a peck on the lips. "I won't judge." Will nodded and looked off to the side. Not used to being ignored, brushed his fingers along Will's sides and across his stomach. Will shuddered and looked back up. Dipper smiled as soon as the attention was back on him and leaned down to nuzzle Will's neck.

   Dipper brought his hand up to cup Will's face as they went into another heated make-out session. Will somehow managed to slip off Dipper's shirt. Dipper went even deeper, tugging at Will's jeans and whining. Will moaned when Dipper felt especially needy and began to suck on his flesh. Will gripped Dipper's arm and said, "Y-You can do it if you w-want." Dipper glanced at him before kissing the spot he was sucking and pulling back. "Are you sure?" Will nodded and brushed his hand along Dipper's cheek. "You're way to gentle to be a dangerous criminal. It's sort of funny." Dipper rolled his eyes and looked down. He began to fiddle with Will's pants' zipper. Will say up and helped him. Dipper pulled the pants down and saw the bulge in Will's boxers. He looked up at Will, saw the boy's red face, and smirked. He rubbed his thumb over the bulge, earning a moan from the bluenet. He pulled the boxers off Will and took the erection in his hands, rubbing it to make it worse. Will started to plead for Dipper to stop. "Stop what?," Dipper asked, halting his actions. "Stop... nnn... teasing," Will begged. Dipper smirked and took Will into his mouth. Will gasped as Dipper began to suck on him and moaned loudly. Dipper kept pulling moans from Will, loving the pleasured sounds. He took Will out of his mouth, and the bluenet whined. Dipper held up a finger before taking off his own pants. Will noticed the huge bulge in his partner's boxers and turned a deep red. Dipper crawled up and ground against Will. Will clenched his teeth and gripped the sheets. Dipper stopped, and Will looked up to see Dipper smirking at him. He decided to make a move and sat up, reaching for Dipper's boxers. He slid them off, revealing Dipper's erection. He laid back down after throwing the piece of cloth aside. He reached under the bed and pulled out a bottle, handing it to Dipper. Dipper stared at it for a minute before taking off the cap and putting some of the substance inside on his fingers. He motioned for Will to roll over and stuck a finger in him, stretching him out. He waited until Will seemed ready enough to add an extra finger. He made scissoring motions, stretching him out. He kissed Will's cheek and whispered, "Are you ready?" Will nodded, and he, deeming Will stretched enough, pulled his fingers out. He kissed Will again before inserting himself where his fingers previously were. Will gasped and gripped the sheets again, arching his back. Dipper waited until Will got used to the feeling before continuing. He started out slow, increasing speed every few thrusts. The sounds spilling from Will's mouth encouraged him to go even faster. He began to pump Will's cock in rhythm to his thrusts.  Will moaned louder an grippe the sheets even tighter, arching his back just a little more. Dipper kept the same pace, still pumping Will. He gave one last thrust before coming inside Will. Will came in his hand at the same time, panting hard. Dipper pulled out, and they both flopped down beside each other, exhausted. Will picked up the planked and pulled it over them, cuddling Dipper. Dipper looked confused. "Shouldn't you get a shower?," he asked. Will yawned. "In the morning," he whispered. Dipper looked towards the closed window. "Shouldn't I be leaving?" Will grumbled. "In the morning," he whined. He pulled Dipper close to himself and went out like a light. Dipper sighed, ran his fingers through Will's hair, and joined his lover in the dream world.