Four.
Soon, Jimmy's clothes were just a pile on the bathroom floor. Dean turned on the hot water and they both got in, shivering a bit at the water hitting their naked skin.
Dean took the shampoo, putting some of it onto his hands and running them through Jimmy's hair. Knowing exactly what his weakness was, Dean tugged a bit at the root of his hair and Jimmy moaned.
Dean continued to wash his hair, but as soon as all the shampoo was all washed down the drain, Dean couldn't do anything else because he could feel his body being pressed up against the tile in the shower. It was cold, but Jimmy kissing him, made him forget all about it.
"I want you." Jimmy whispered gruffly in Deans ear, kissing from the bottom of his ear and down his collarbone.
Dean flipped them around and kissed Jimmy again. Without much warning, Dean wrapped a hand around Jimmy's cock, making Jimmy groan, echoing in the expensive bathroom. After Dean started stroking him, Jimmy could feel himself teetering on the edge.
"Dean, stop. I want you inside of me."
Dean was happy to comply.
"Spread." Dean said in such a low octave that Jimmy had to stifle another moan. Jimmy opened his legs for Dean, only Dean. Dean took his finger, already wet from the shower and added just the slightest pressure to Jimmy's puckered hole, not yet penetrating.
"Dean." Jimmy gasped, gripping Deans shoulders.
"What is it, Jimmy? What do you want?" Dean said, with a big shit-eating grin on his face.
"Take me, Dean." He said, and Dean slipped the finger inside of jimmy.
Jimmy was almost overwhelmed with the sensations of Deans finger inside of his, to the knuckle, but he still wanted more. Dean added another finger, stretching him and preparing him for his cock. When he was ready, Dean removed his fingers, leaving Jimmy feeling empty. That soon was resolved when Dean slicked up his cock with the shower water and eased in slowly to the hilt.
Dean waited for him to adjust, till Jimmy practically yelled at him to move. Dean started to make short, erratic thrusts into him, making them both moan at the feeling.
Dean used Jimmy's kink against him, pulling at his hair right as Dean hit his prostate, and Jimmy nearly lost it right there, moaning as he gripped the back of Deans neck.
As he was pounding into Jimmy, Dean gripped the base of his cock, stroking him. That was what send him over the edge, thick ropey come coating both there stomachs and on Deans hand.
After a few more thrusts, Dean followed suit, and Jimmy could feel Deans release inside of him.
After catching there breaths, they both cleaned off and Dean finished conditioning Jimmy's hair, loving the feeling of running his hands through the dark locks.