Looking down between them, he didn't ever imagine that he would see Scott...and himself naked together. He felt the bundles of nerves shocked throughout his cock as Scott held him in his hand and began stroking. His hand wasn't soft like a woman's touch but the roughness was actually a little welcoming. He knew it wouldn't take much more before there was precum slipping out from the tip, he was fully aroused and wanted nothing more than to scream out and move against Scott's hands just to feel more.
There was a slight shock when Stiles felt Scott's hand by his ass, he knew that obviously things would eventually go that way but there was some fear at first. He hadn't even, it was just never a thought and he knew there was a possibility it would hurt...a lot. Not only that but what if he didn't like it. He took in a sharp breath and held onto it once he felt those fingers pressing against his ass and he tried to relax as best he could as first one then another pushed inside of him. It hurt a little, feeling more awkward than painful at first. His entire body had tensed and he held onto Scott's arm while he tried to relax into the feeling more. "Oh...oh fuck..." It was a murmur from his lips but it had felt better than he thought.
His hand slipped from Scott's arm and fell down between them, fingers running over Scott's other hand as he gripped both of their cocks together rubbing them. Even as he moved away just to get the lube and condom Stiles continued, focusing on Scott's cock now. Fingers wrapping around his thick member and beginning to slowly move up and down, his body betraying him as he let out a moan just watching himself jerk off his best friend. When Scott's lubed fingers returned to his ass he'd relaxed again, but continued to move his hand against Scott's cock. There was a chill that sent through his system, the lube had only made it even more enjoyable. His thumb ran over the tip of Scott's cock and then grabbed his own again to move in unison as he moved up and down. His eyes never drifting from either watching their bodies together, or Scott's eyes.