Title: The First Time
Pairings: Dean/Bobby
Category: Romance
Rating M for underage sex
Disclaimer: I don't own Supernatural or any of the characters. If I owned Supernatural, Bobby Singer would not be dead! Bloody writers
Summary: Dean remembers the first time he had sex with Bobby. Underage slash!
[+ .. -]
Dean remembers it clearly like it was yesterday. He will always remember that first night. Now that Bobby has passed he kept thinking back on it, replaying the memory over and over in his head. He must have been 16, or maybe 14, the point was he was young but it didn't matter.
John had shipped Dean over to Bobby's house for the weekend so Sammy could have more practice in the field. Dean didn't really like staying at Bobby's. The house was old and smiled like dust. Bobby was never home and when he was home he was always pasted out drunk. Dean was always left to watch TV or God forbid read a book.
He was so bored all the time. Dean couldn't wait for the weekend to be over. While John had promised that he would only stay the weekend, whatever they were hunting had gotten away (Fucking Sammy) and now it was looking like Dean might have to stay the week with Bobby. A week shouldn't be too long, right?
Sunday rolled on into Monday, and by Tuesday Dean couldn't even remember what day it was. He knew when it was morning because the sun was up, 4 o'clock because that's when Judge Judy came on, and night time because it was dark. Other than that the days just all started to feel the same. That is until this night.
Dean was lying on the couch in his pajamas watching some movie about a cop and a lady. Too bad it was TV and not porn. That cop and lady would be hot doing it. He didn't exactly know when Bobby had strolled on into the house; all he knew was at that moment he caught Bobby staring at him from the doorway. Dean jumped up high, startled.
"When did you get back?" he asked.
"Earlier. I was just wondering what you were doing around here." Bobby replied back.
"Just watching TV," but Bobby had already decided to sit down on the couch next to him and watch TV with him. Dean wasn't going to protest. It was the most company he's had in three days or four. But Bobby smelled bad of booze and cigarettes.
Dean went back to watching the cop and the lady, imaging all the ways they would probably do it if the movie was real life. He just happened to look over again and noticed Bobby starting at him.
"Come here," he said to Dean.
"Go where?" he asked.
"Come over here and sit closer to me?" Dean was not sure what to do at first but decided that it should be fine since it was Bobby. He moved closer to the older man on the couch. Bobby throw his arm around Dean and brought their bodies closer together. "What wrong, boy, don't you sit like this with your daddy?"
"No, I don't sit like this with John."
"John? Well, he sure does have you boys deprived some good." Bobby replied.
The two sat like that for some time watching the rest of the movie but Dean wasn't really paying attention anymore. It was his hormonal phase for crying out loud, every little touch now-a-days turned him on and this case was no different. Just being this close to Bobby was making Dean hard.
He tried to hide it as best that he could so Bobby wouldn't freak out on him like John freaks out. But something very interesting happened next. Out of no where Bobby reached his hand over Dean and grabbed his erection. Dean moaned loudly at the touch. He wasn't sure why but it felt very good.
When Dean turned to his right he mouth was met with Bobby's and he greedily opened it to swallow down Bobby's tongue. Bobby slowly pushed the boy down into the couch and climbed on top of him. Dean felt dominated by the older man but it was a good domination. Dean laid there allowing Bobby to kiss him and excited to find that his dick could get even harder.
After some intense kissing Bobby removed Dean's shirt and pulled off his pants revealing his erection underneath his boxers. Dean felt very exposed lying naked under Bobby's stare but Bobby was staring at him with such admiration that his feelings quickly changed. Bobby also removed his shirt and leaded over the naked boy.
Bobby slowly kissed down his chest until he reached Dean's underwear. He took the underwear off the youth and flipped him over on his stomach. Dean gasped when he felt Bobby's thumb circle around his entrance. He didn't even know that he ass could feel that good. It felt even better when Bobby opened his ass checks wide and stuck his tongue inside.
Bobby made sure to spit on Dean's whole to get it nice and wet so it was easy when he stuck a finger inside. Dean moaned at the feeling and Bobby slide a second finger inside. He pumped his fingers in and out to get him to stretch him wide. Dean was moaning and wiggling underneath him shooting pre-cum out his teenage dick.
Bobby dropped his pants and slowly pushed his dick inside Dean. It was definitely a lot bigger than two fingers but Dean was determined to see this through. He was too horny to tell Bobby it hurt. Bobby pushed another inch inside and this one hurt more than the last one. Bobby reached over and stroked his penis, it helped Dean forget about the pain, while Bobby's cock slide further inside.
Finally the boy started to relax and Bobby was able to push all the way inside of him. Bobby tried to fuck the boy as gentle as he could but that tight heat was driving him crazy. So he pushed a little harder and Dean Winchester pushed back into him and moaned like a bitch in heat. Bobby took that as permission enough to continue.
Dean isn't as fragile as he pretends to be and once Bobby figured that out he turned the pace up faster. He fucked that kid until he was screaming Bobby's name as loud as possible. He didn't have a lot of neighbors but he was sure every one of them could hear Dean moaning loudly. Bobby could barely hear the TV anymore over the sound of skin slapping on skin. Bobby wasn't usually a selfish lover but right now he wanted to come as quickly as possible.
After a few more thrusts he came inside Dean. He pulled out and laid the boy down on his back. He pumped his fist over Dean's dick until the boy came all over his hand. Dean laid there on Bobby's couch breathing hard just letting his orgasm wash over him. That night he and Bobby fell asleep on the couch.
Every night after that one, he and Bobby fucked in the upstairs' bedroom. Dean was sad knowing that John would be coming to pick him up at the end of this great week at Bobby's. But it didn't matter John still came on Saturday morning hocking the impala horn for Dean. Before Dean ran outside he wrapped his arms around Bobby's neck and kissed him on the mouth. Bobby wrapped his arms around the small framed boy and kissed him back. There would be plenty of weekends to come.