Simon Said So

Dean’s stomach was doing back flips



as he sat down on the bed. He felt like he was 14 again and about to have sex for the first time. He hadn’t thought about her in forever. They were staying in Idaho, dad was hunting a nest of Morlocks that lived under the sparse city. Turned out it was some things that had been turned by radioactivity in the soil, but that was another story. Dean and Sam had stayed in Emmett Bench, population 3,000 and change. And in that change was Stacey Parker, 30 something widow, living alone on a small plot of land. Dean had seen the woman working her small garden and was instantly taken with her. He had offered her help, she had offered him some pocket money. Within two weeks he had made his move to kiss her.



She had thought it sweet that a cute boy like Dean was attracted to her, she had thought her days of fending off advances well behind her. Dean had taken it horribly and spent the rest of the hunt in a what Sammy called a Dunk. Which was short for Dean funk. The last day his dad had come home, victorious and seeking some kind of refuge involving a bar and a lot of beer. He had told the boys to get their stuff ready, they were leaving in the morning. Sam had told Dean to go and say goodbye to her. Dean hemmed and hawed and then finally went. Stacey was relieved to see him, but looked saddened when he told her he was leaving. He apologized again, feeling like he was even younger than he was. He had moved to leave when she leaned over and kissed him on the cheek. He moved his face and kissed her on the mouth. He felt her resist, and then kiss him back. As she took him over to the couch he felt like he was going to explode in anticipation and excitement. She had showed him how to love a woman that night. And he had never forgotten it.



And now here he was again, feeling nervous and excited. He was still hesitant because it was a guy, but his loins were throbbing from the need to release so bad, he was willing to do anything. But as the kid patted the pillow, gesturing for Dean to lie back, Dean tried not to breath fast as his whole body shook in unease.



“Calm down”, the kid said putting one hand on Dean’s arm. The shaking calmed slightly, but the feeling he was about to jump out of his skin wouldn’t vanish. “Is it that weird ?”, he asked stroking his hand up and down Dean’s arm, making goosebumps to rise. Dean shivered again, this time from the tingle of contact.



“I can’t believe I am naked in a bed with a guy…”, his voice was strained, “I just can’t…”



“Shhh”, the punk said moving closer to Dean. Dean felt his body tense as the boy’s naked flesh pressed up against Dean’s, “It won’t be bad at all”, and he leaned in to kiss Dean. Dean’s lips were like rock, sealed shut as Dean’s head moved back against the headboard. There was no way he was kissing a dude.



The boy kept moving his tongue across the lips, as his hand moved down and gripped Dean’s rigid member. Dean gasped in erotic shock as the feeling of the boy’ hand around his cock made him almost scream out in joy. When his mouth opened the kid’s tongue flew into Dean’s mouth, and he froze as he felt his mouth invaded by the warm member. As the boy pushed further Dean tried not to move as he felt himself starting to panic. Then the boy’s hand started to let go of the hunter’s dick.



“MMwwhhhaaa”, Dean said trying to complain around the kiss. Dean felt the kid’s tongue force it’s way in again and the hand grip the cock again.



Dean got the point.



Dean’s tongue slowly moved against the kid’s, and he closed his eyes as he surrendered to the feeling and started to kiss him back. As he did the hand started to stroke the length of Dean’s fat rod. As it moved Dean kissed the kid harder, his hands flew up and gripped the boy’s face, pulling him closer into the kiss. It was like he was a dog being taught a new trick. If he kissed then the kid stroked his cock, if he drew back he stopped. So he kissed him for all he had.



Dean could feel the pleasure racing through his body as the boy’s hand kept slowly moving up the entire length of the shaft. It was enough to drive Dean nuts, but not enough to get him to get off. Dean out his hand over the boy’s and tried to get him to go faster, but the boy stopped altogether.



“No touching”, the kid said like he was scolding a child, “You can’t touch you dick until you cum” The command made Dean moan as he knew there was no way he could cum without his help. The boy moved in to kiss Dean again and this time Dean opened his mouth and kissed him back. The boy started to trail his finger across Dean’s sensitive scrotum and the affect was instantaneous. Dean jumped slightly and moaned again, kissing the boy even harder. The finger moved from just before Dean’s ass to his smooth ball sac. The boy chucked and pulled back from the kiss, “You shave ?”



Dean gave him one of his famous grins and said, “It drives women nuts”



“Not just women”, the kid said sliding down Dean’s body. He traced the outlines of Dean’s abs with his tongue and Dean propped his head up to watch. The boy’s mouth moved over the hard six pack, each ridge moving further and further down. When he got to the edge of Dean’s pubes he gripped the massive cock and started to kick around the base. Dean was almost sobbing for the boy to take it in his mouth. When he licked Dean’s tip the hunter just threw his head back into the pillow and closed his eyes. He had never felt anything so damn fine in his life.



The boy could barely wrap his fingers around the staff it was so thick. He licked it like a popsicle, trailing around the meaty vein and then up to the tip to lick out his precum. Dean as completely lost in passion now. He didn’t care about anything but getting off and the feelings that were rushing through his body. When the boy slid his mouth around the whole cock Dean gasped again and placed his hands on the top of the boy’s head. He guided his face down the length and then back up again. It was like a warm, enveloping fist, sucking and pulling him with all it’s might. The boy moved off Dean’s cock and started to work the well sized balls over. Almost larger than golf balls, the youth could only put one in his mouth at a time, swirling the sensitive orbs around making Dean cry out even louder.



His tongue started to work underneath the balls and then lower, and Dean knew what was coming. Minus a doctor, no one had ever touched his ass before, not a girl, no one. It was a place that symbolized everything masculine for some reason, and Dean was worried about how it would feel. He started to try to pull his head back up again, wanting him to suck him some more. But the boy ignored the pulling and circled Dean’s virgin hole with his tongue.



Dean made a sound of like an animal like grunt. The boy did it again and Dean was feeling something all new. It was like an electric shock every time the warm tongue moved over the tight muscle. He kept going, the circles becoming smaller and smaller until the tip was pushing at Dean’s tight muscle. Dean clenched it tight, not wanting anything to go in there, but still was having a hard time concentrating with the way it was making him feel. The boy reached around and stroked Dean’s turgid cock, and Dean’s resolve slipped. He made a slight squeak as the boy’s tongue penetrated the untouched hole. He was holding his breath as the sensation of the wet, warm invader made Dean relax even more, allowing the kid to move even further in. Dean moaned and started to thrash his head from side to side. It was driving him crazy ! He had heard that gay guys did rim jobs but he had never even asked a girl to try this on him. But as he moved his legs wider to give him more room, he knew he was going to have it done a lot more times.



The boy pulled up for a second and said, “Grab your legs and hold them back”



It wasn’t a command, so it was Dean’s choice. But if he did he was giving him permission, allowing it. He felt it go in again and tried to fight it, but knew he couldn’t. He grabbed the back of his knees and pulled his long legs further apart. The difference was incredible. It may have been only a quarter inch, but every particle of Dean’s body was on fire from the ravenous desire to have him go even farther. The body roughly moved Dean’s cheeks back even more and went as far as he good. Dean was crying out, the feelings so much more than anything he ever felt. The boy tongue fucked him for almost 5 minutes, Dean pushing his ass back as far as he could, trying to drive it deeper and deeper in.



Then the feeling as gone as the boy moved up from underneath him. He was kneeling now between Dean’s legs and Dean was still holding his knees, panting like he had just ran a marathon.



“You like that ?”



“Fuck yeah”, Dean said hoping he would go back.



“Sweet”, the boy said and went down to Dean’s cock. Dean felt one of the kid’s hand slip under him and he felt a finger probe the slick entrance of his ass. He started to sit up and protest but the kid engulfed his cock in one swallow, making the protest go from, “Heyyyyaaawwww”, and his head fell back to the pillow. The feelings were conflicting to say the least. His finger was wedged in his tight ass, slowly moving forward as Dean moved his hips to get his cock further into the kid’s mouth. He would buck his hips up, moving farther away from the finger but every time he moved back he moved down onto the finger even more. It was like he was fucking himself on it almost, but it was starting to hurt.



The boy held his finger there for a second, letting the walls of muscles get used to it’s presence. He licked the tip of Dean’s cock, causing him to spasm and cry out, opening his hole for second. The finger slid further in and Dean gasped in shock and discomfort. This was going too far and he went to grab the kid’s hand away.



When the finger touched something in Dean and everything exploded.



It was like seeing light behind his eyes and he could hear himself cry out, his whole body jerking like it had an electrical wire running through it. Dean actually had felt his dick jerk for a moment. It was the closet thing he had felt so far to an orgasm, but he hadn’t cum.



“W’what was…”



And the kid did it again. Dean whimpered as he felt his whole body come to life, his dick jerked again, even more precum spilling out.



“That ?”, and the kid stroked it one more time. Dean felt himself push back against the finger, trying to force it even further in. Every time it was like one inch closer to cumming and Dean had to cum.



“Want me to stop ?”, and he started to pull the finger out. Dean gasped, the feeling of emptiness in him was something he couldn’t bear. He called out, “Wait”, and held the kid’s wrist still. He could feel his ass flexing around it, it was a little uncomfortable but it wasn’t hurting any more. Dean moved his ass down over the hand again and felt the finger touch that spot again.



“Oh god”, Dean moaned as he started to move himself up and don the bed, finger fucking himself., “Right there”, Dean was oblivious to what he was saying. Whatever this was it as like mainlining sex. So much more than jerking off, even better than a blow job. Whatever that finger was hitting, it was incredible.



“Yeah come on tough guy”, the kid said sneering, “Fuck yourself on my finger”



Dean wanted to tell him to fuck off, but his ass kept moving and he felt himself get closer to cumming. He couldn’t believe he was doing this, pushing some kid’s finger up his ass to get off. He was mortified by what he was doing, but there was no way he was stopping. The kid moved his finger out himself and then plunged it in again. Dean ’s mouth was open but no sound was coming out as the kid started to drive his finger into his virgin ass. He slowed and started to pull his finger out, as it retreated Dean heard himself moan in disappointment and bed, “Please don’t stop”



“We’re not done”, the kid said and put two fingers in young Mr. Winchester’s crack. Dean clenched his teeth tightly as the two fingers made their way in, it wasn’t all that painful, but it was uncomfortable as all hell. He started to tell him to stop when he hit the spot again. With the two fingers it covered more space and the feeling was even more intense. Dean closed his eyes and just whimpered as the kid’s two fingers moved in and out of his ass. Each time sending Dean further and further into ecstasy. He was lost and he knew it. He couldn’t believe he was letting him do this to him yet every time he hit that spot Dean felt his ass push against it like a bitch in heat.



“Grab your legs”, the kid said, and this time Dean grabbed them without hesitation. Dean felt the third finger slip in and now it was starting to hurt. Every time he would push in Dean would wince in pain, as the walls of his ass protested the assault. Dean wanted to cry out, but he knew the kid was doing what he wanted to do. Instead Dean just forced his mouth closed and waited it out. After about 5 minutes the pain had passed some, and the pleasure was starting to come back. Dean could tell his ass had stretched some as the kind was now plunging all three into him without much protest at all. Every so often the kid would slow down and go back to that spot. Making Dean cry out for the kid to keep going.



When the kid took his fingers out Dean felt the discomfort go away, but there was an odd sense of loss as he pulled them out altogether.



The kid kneeled there, grabbing Dean’s cock, playing with it as he talked, “You ready to cum ?”



“Please !”, Dean called out watching his member pulse in his hands.



“You like that spot ?”, Dean nodded, not trusting himself to use words to describe it.



“I can make that feel a lot better”



“Please man…let me cum”, Dean couldn’t believe the words we was hearing from his mouth. Begging this punk….half his size…



“I can make you cum”



And he took Dean’s hands away from his knees and then grabbed them himself. He help Dean’s legs spread and moved closer to Dean. Dean’s eyes widened as he tried to close his legs, “NO !”, the hunter screamed, “No way”



The kid just smiled holding the legs apart, “It’s no different from the fingers…and trust me it feels a lot better” Dean still held his legs closed, “No way man, no way”



The kid dropped his kegs, one hand grabbing the rigid cock, the other slipping under Dean and plunging two fingers into him. Dean drew a deep breath in shock and then felt his whole body spasm as the kid stroked his cock while hitting the spot. Dean couldn’t move it was so much. Like the finger and his cock were connected. He panted, moaning with each stroke, “This is nothing Dean, nothing to what it would feel like” And he stopped.



“Or you can just not cum”



Dean looked up at the boy. He wanted to please with him, beg him for anything else. Anything at all he would do, but this…letting some guy take his ass. And he saw the kid’s grin, he knew he had already won. He was just letting Dean realize it.



“Please don’t make it hurt”, Dean begged, knowing what was coming next.



“It’s going to hurt some”, the kid said grabbing the legs again, “But you can handle a little pain right ?”



Dean closed his eyes again as he heard the kid spit onto his cock. Dean felt the boy let go of his legs and the boy get off the bed. His eyes shot up and he sat up, wondering if the kid was really just going to leave him like this.



The kid laughed, “Calm down, I’m not going”, he was looking through his jeans pocket, “Ah here it is”, and held up a condom. As he jumped back on the bed he tore open the seal, pulling out the mall tube of lube that was contained inside.



“Lay back”, the kid said as he coated Dean’s ass with the slick liquid. He felt the coldness work down into his crack as the kid coated it as well as he could. Dean tried not to think about what was about to happen, he tried to think of anything else but his whole life seemed to be this, right now. He jerked when he felt the head touch his opening. He kept his eyes closed as he heard the kid say, “Relax. You have to relax or this really will hurt. Just push out like you are going to the bathroom and whatever you do don’t clench”



The head pressed at Dean’s hole, the tip spreading Dean’s rosebud slowly. Dean let out a slight whimper as he felt the boys dick press against the flesh, forcing it’s way past the muscle. He could hear the boy grunt as he bore down on the hole, the very tip sliding partially in. Dean has his eyes sealed shut as he tried to push past the pain as the kid’s massive head moved the muscle apart, letting the head pop into virgin ass.



“Unnnghhh”, Dean cried out as his first instinct was to push it out. This was too much, it was stinging and Dean’s breaths were like hisses as he tried to ride the pain out.



“God you’re tight”, the kid said, feeling his ass grip his cock like a vice, “This is going to take too long this way”, the kid said, more to himself since Dean was in another world trying not to scream out.



“You don’t feel the pain”



And it was gone. All the pressure and burning faded away, leaving Dean feeling the boy’s cock rest inside of him. The boy pushed forward slightly and Dean felt the length start to move down his stretched walls. It didn’t feel good but it wasn’t feeling bad. Dean just felt full as the kid kept going.



“God it’s like an oven”, the kid said pushing down, watching his whole cock disappear into Dean’s ass. Dean groaned as he felt the cock move deep in him, the kid stopped and held it there for a second.



“Fuck that feels huge”, Dean said trying to catch his breath.



The kid smiled, “I get by” Finally feeling his pubes rest against Dean’s smooth ass the boy stopped and positioned himself. He pulled his cock out slightly and Dean jumped as it rode over his prostate. The boy then reversed and pushed back in, making Dean groan again. His hands were on each side of the bed, clenched tight holding the sheets as the kid moved his dick back and forth in Dean’s ass.



He pulled back even further and then back in, hitting the spot with more force. Dean felt his cock jerk as the kid slowly got him used to being fucked. The boy pulled his hips back, pulling almost 4 inches out and then thrust it back in, making Dean cry out in pleasure. The boy started to pick up sped as his cock pistoned in and out of Dean’s tight hole. Each stroke in earned him a small whimper from Dean as he laid there, felling the kids cock move in and out of him. The boy started to fuck faster, holding Dean’s legs even further apart, Dean heard himself cry out a yes as the kid began to ravage his hole.



The boy moved his knees around his chest as he leaned in and started to press his weight in the thrusts. Dean wrapped his muscular legs around the boy, pulling himself into the cock each time. The boy could see Dean push up with each stroke and smiled as he tore into him. The boy was over Dean now as he fucked him, his face looking down at the hunter as his eyes rolled back in his head from the feelings. The boy grabbed Dean’s head and brought his mouth up to his, Dean hungrily kissed him back, pulling the kid into him harder and harder. Dean could feel every stroke hit his button as he pulled himself onto the cock with his legs. He didn’t care about anything but the feeling of that cock in his ass. He was gone, oblivious to the world.



He boy broke off the kiss and said breathlessly, “Get on all fours”



Dean looked with confusion for a second, his mind not quite comprehending English. He boy moved his shoulders over and Dean started to turn around, the cock still wedged in his ass. He got on his knees, holding himself up with his hands as the kid grabbed his waist and thrust forward.



Dean fell forward, his face falling into the pillow as he screamed out in bliss. He felt the kid hit a whole new area inside of him and he felt his cock hit the spot from another angle, driving him even further into passion. With each thrust Dean could feel the kids cock slam into him, the started pushing back into it, moving his ass to meet the cock where it would feel the best. The kid stopped fucking and watched as Dean pushed back onto his cock, fucking himself on the swollen member all by himself.



“Come on Dean”, the kid said, “Fuck yourself on that cock”



Dean did just that. Pushing back as hard as he could, each time a flash of pleasure shooting through his body making push even harder. He didn’t care what anyone thought or said right now. All he knew was that he needed that cock in his ass now. And he didn’t care who knew it. The boy pulled out, Dean’s ass moving backwards, trying to follow. The kid got up off the bed, Dean turned, face flushed, “What are you doing ?”



The kind grabbed the chair and sat down on it. His cock looked huge, pointing up from his lap. The boy spread his legs apart and smiled, “You want it Dean ? Come over here and sit on it”



Dean scrambled off the bed, half tripping in the sheets. He moved over to the chair and started to lower himself when the kid stopped him, “Ask me”



“Wa ?”, Dean said trying to sit down.



“Ask me”



Dean stopped, “Oh come on man….bad enough I am doing this…”



“Ask me or forget it”



Dean sighed and closed his eyes, “Please get me off”



“Nope”



Dean sighed again, “Please let me sit on it”



“More”



Dean opened his eyes and barked, “Please fuck me !”



The room was silent as the boy smiled and gestured to his lap, “Be my guest”



Dean moved over the kid’s lap, grabbing the boy’s cock and positioning it under his ass. He sat down slowly, gasping as he felt the length of the tool move back into his ass, filling him completely. He felt himself take the whole thing and wrapped his arms around the kid’s neck. He kid grabbed Dean’s broad chest and held him steady. Dean moved his legs up slightly and felt the cock move through him and then forced his way back down onto it. This felt incredible. He could control everything, the speed, the pressure, the force. As he got used to it Dean started to fuck himself hard on the kid’s cock, the whole time moaning, “Can’t believe I’m letting you do this”, he said whimpering. He could feel his cock getting close as he pounded himself on the massive cock.



He felt like a hoar, pleasuring himself at any cost, “Can’t believe I’m letting you fuck me”, he grunted as he felt the cock getting him closer and closer. It was like nothing he had ever heard of, the feeling of the cock pushing into his tight hole, filling him up in places he hadn’t known were empty. Dean’s head was back as he rode the kid long and hard. His eyes closed, mouth open as he slammed himself down harder and harder onto his cock.



He felt the familiar tingling and knew he was getting closer. As he picked up the pace he could feel his balls start to tingle and he knew there was no stopping it now.



“You are completely yourself again”



And Dean came to, he fully realized he was naked, pounding himself onto this kid’s huge cock. He gasped in shock a the realization he had been fucking him when his cock exploded. It was like nothing he had ever felt. His orgasm came from his cock and his ass at the same time. He felt himself push down as he came, the feeling of the cock penetrating him as he ejaculated was incredible. His head was swimmy and he felt his whole body jerk with each spasm of his cock. He had shot everywhere, up his abs, his chest, some even landed up in cheek. He was exhausted, so was surprised when the kid tightened his hold on his chest and started to pound him again.



Dean cried out as the sensitive prostate got hit again and again, Dean felt even more cum dribble out his cock as the boy slammed his ass three, four and then he pushed Dean down, and Dean felt it. He felt the cock pulse around his ass and he knew the boy was cumming in him. His eyes closed as he felt the dwindling feelings of nirvana start to fade, as they always did after sex.



The boy pushed Dean up, off his cock. Dean half staggered back and moaned as the deflating cock slid out his ass. The boy pushed Dean back onto the bed, the hunter’s body not wanted to move at all. He had never cum like that ever, and the thought a guy had done it…it was too much to compute. He closed his eyes and the world went black.



+++++++++++++++++++++++++++++++++++++



He woke up and was in the Ipmpala. He was parked across from the gas station, it was an hour later. He looked around in confusion for a second and tried to gather his wits. He had called Sam, told him it wasn’t Andy…



…and then he looked around, asking questions. He found out the woman was Holly Beckett and then…



He shook his head, not knowing where an hour had gone. He must have been more tired than he thought, As he started the car he shook his head, this whole Sammy thing was getting to be too much. Dean didn’t know how he could convince him that just because these kids had powers didn’t make them evil when he was so sure himself.



He pulled out and started back to where he had let am with Andy. As he drove off he felt a pain in his ass, like he had slept on it wrong. He just felt a general feeling of soreness, like he had just gone five round with someone. He was getting too old for this shit.



As he pulled away Ansem watched him drive off down the street. No way of stopping it now, he had taken enough time with Andy. Letting dean know who the woman was would put them on the trail and get Andy to realize what his potential was. It was too bad he couldn’t have Dean remember all of that, just the memory of him begging to be fucked…well that would have haunted the hunter forever.



As he walked back to the diner he laughed to himself…he wondered what Dean was going to do when he started having the dreams he left him. He had to admit, it was good to be a jedi.