Spin the Bottle Truth or Dare- Shaymien

Self Exploration

Ive had the thought of Shayne exploring his body since I wrote the first chapter, so here's this. (Please don't take any of this as actual sexual advice please)

Words: 1860~

The door clicked shut behind Shayne as he entered his apartment, alone. He and Damien had agreed that tonight they would stay in their separate apartments, and hopefully by the end of the week they could have Shayne moved into Damien's apartment. Some might think that moving in together so soon was taking things too fast, but they had known each other for over eight years, and had been roommates before. They had decided on Damien's apartment because they didn't want to move all of his cat stuff into Shayne's tiny apartment.

Slipping out of his jacket, Shayne headed towards his kitchen to grab some ice water. His footsteps padded across the floor, along the way he slipped out of his shoes, kicking them away indifferently, not caring where they ended up since he'd just find them later. Pouring himself a glass of water, he sat down on his couch and pulled out his phone. Earlier in the day, he had bookmarked a bunch of sites on bottoming, anal fingering, anal play, etcetera. He casually scrolled down one of the pages that had visual aids, and his dick hardened slightly. Shayne had decided that he would try fingering himself tonight, to see how he liked it and to get used to how it felt to have something in his ass.

Though he had watched some gay porn, he'd never gone so far as to try anything anal with himself. He'd thought about it a few times, but he usually just jacked off and called it good, never bothering to worry about how he would go about fingering himself. He finished his water, standing up and setting his cup down in the sink.

With a groan, Shayne extended his arms upward in a big stretch. He chuckled, remembering that Courtney had once said his arms looked like frog legs when he did that. Upon entering his room, he slipped out of his shirt, and wiggled out of his jeans and boxers. It was warm enough in his apartment that being naked felt pretty great. He set up his pillows on his bed so he could sit comfortably, and he sat down against them. Shayne reached over to his bedside table, opening the bottom drawer, and digging under some paperwork till he found his bottle of lube. He didn't always use lube when he jacked off, usually only if he remembered, and otherwise he would just lick his hand. He was grateful to have it, though, because it had been awkward enough when he had purchased this bottle, he didn't want to have to deal with that uncomfortableness again.

He set the bottle next to himself on the bed, and moved his knees up to his chin, opening his legs to look down at his dick, semi-hard at the thought of what he was about to do. He had read that its best to not eat for at least half a day before doing anything, so the last thing he ate that day was lunch, and it was now after dark. No matter how many articles he read, he was still nervous and a little scared about doing something wrong and possibly hurting himself. He breathed in deeply, and let out a huge, calming sigh.

"Okay," he said out loud to no one in particular, "this is fine, I can do this." His voice shook slightly, feeling strange talking to himself but also slightly comforted.

He evened out his breathing again, and leaned back onto his pillows, his left hand slid down his own body, taking his time to get himself excited, and slipped beneath his dick, pressing lightly onto his asshole. He sucked in a breath, even just touching the outside felt exciting, and his breathing picked up. He fumbled wildly at his side to grab the bottle of lube, squeezing some onto his fingertips and rubbing them together to warm them up. From what he read, insertion would hurt but it would hurt less if he was properly lubed.

His now lube slicked finger returned to his tightly closed hole, sliding around and spreading the still slightly cold lube liberally onto the outside. His right hand came to rest on his dick, not stroking it but just holding it there, almost as if for reassurance. He took a deep breath in, and tried to relax as much as possible, before finally putting some pressure onto his asshole. His finger slipped in to the first knuckle, and he let out a loud gasp, eyes snapping wide open. There was a slight sting, but it felt so good that his dick jumped at the feeling.