Closing his eyes for moment, Ben took a deep breath and slowly lowered himself until he felt the tip of Dean's cock press against his hole. Trying to forget the pain he experienced last time, he bit his lip and let gravity do its work. As the head finally passed the rim, the burning began to build in him. Dean's cock felt huge, though he knew it wasn't monster size or anything, but was big enough he would bleed a bit. When he felt his cheeks finally rest upon Dean's groin, he opened his eyes and glanced down. Their eyes met, and it looked as though Dean wanted him to stop. Deciding not to give him a chance to push him up and off him, he squeezed his ass hard onto Dean's dick. He smirked as Dean's eyes bulged, and his mouth slightly dropped open.
Winking, he pushed himself back up and dropped again, this time not clamping down as hard. He watched as Dean reached and took hold of his soft dick. Stroking it a couple of times and twisting his hand soon woke his dick up, and it began to leak precum. Smiling, Dean rotated his hand and used his fingers to gently lift and massage his balls. Changing his angle a bit, he felt Dean's dick hit a spot on the inside that made his body tingle. His felt his hips twitch and on the next drop he hit it on the dot.
"Oh..." he moaned, not able to keep it in.
Beneath him, Dean smirked at him and gave his dick another stroke. The next time, Dean pushed up into him with a bit harder thrust, almost making him cum.
"Dean..." he whispered, looking down at him with a pained face.
"Does it feel good?" he asked again, thrusting again, harder. Unable to speak, he nodded his head weakly. He could still feel the pain, but the pleasure was overshadowing it. Dean lifted his arm and planted one of his hands on his chest, while the other wrapped around the back of his neck. Feeling Dean pulling him down, he smiled as he felt their lips meet. While he was bent down, Dean leaned up and rocked them backwards. Now on his back, he looked up as Dean repositioned his knees onto the blanket. The shift of weight had now changed, giving him no control on the speed of their actions. But even as Dean pulled back for another thrust, he was amazed that this position wasn't as painful as it was when he rode Dean. This was much better, and he smiled up at Dean, letting him know how he felt. Smiling in turn, Dean thrusted with more force, and he raised his legs onto his shoulders, while using his other hand to stroke him.
The speed increasing, he watched as Dean began to sweat in earnest with a savage look spreading across his face. When he pulled back, his entire length exited him, and then slammed back in. This time, there was quite a bit of pain, but he was determined to not let it show. However, after only a few more thrusts, the pain became almost too much, and he whimpered as Dean's cock reentered. Seeing this, Dean slowed and a pained look spread across his face. Coming to a halt, he leaned down and kissed him with rapid breathes. As he drew back from his lips, he noticed Dean's mouth was red. Wondering if he had somehow bit down on him, he could see the skin around his mouth wasn't broken. Raising his own hand to his face, he touched his mouth and then looked at his hands. It seemed that he had bit his own lip sometime during their fuck. Dean began to pull out, as if to end their fun.
Thinking quickly, he reached down and grabbed the based of Dean's thick cock, not letting him pull out anymore. Summoning his courage, he pulled until Dean reluctantly pushed back into his heat. Still holding him, he pushed the dick out a bit, and then pulled it back in until Dean continued the movements without Ben to force him to do it. Finally, his speed returned to what it had been, except for Dean altering his angle until Ben felt the warmth blossom inside when it hit his prostate. Smiling, he nodded to Dean, letting him know it was good again. A look of relief was evident, and then he lifted his right leg up into a vertical position. Slowly, Dean rotated his hips until it was like he was lying on his side. His dick moved easier now, and the pain disappeared all together. Wrapping his hand around his thigh, Dean began to move faster than ever, pushing in with his hips, and at the same time pulling his body into him by his lower thigh.
"Oh fuck..." he heard himself say.
"Yea?" Dean asked, eyes looking almost malicious and greedy for as much as he could get out of Ben. He lifted his chest until he was propped up on his elbow, and used his other hand to reach up to Dean's head and pulled him down until they kissed, as if hungry for the release. They rested their foreheads together, breathing raggedly into each others mouths.
"Fuck me Dean." he growled, sounding almost animalistic and desperate. Eyes widening, he grinned and sped up, with a dark smirk. His thrusts erratic, he went faster, but not as fast as he was hoping for.
"Stop being a pussy and fuck my ass!" he roared, though he wasn't quite sure where that came from. However, it seemed to do the trick. Slamming into him, he then rotated his body once more. Twisting his vertical leg down to the ground, he used his knee to nudge his left leg until his knee hit the ground as well. He twisted his chest until he was lying down on his stomach. As the poundings built ever more intense, he pushed with his arms until he was on hands and knees. Now in a doggy style position, he turned his head and smirked at Dean, as the sound of his groin slamming against his ass cheeks increased in volume and speed. The sound was almost funny, reminding him of someone running barefoot on a hard surface. It echoed all the way down the cliff, and as he looked forward once more, he watched the deer that were browsing lift their heads and bolted back into the woods. Dean laid his chest across his back until he was able to grip onto his rock hard dick with his right hand, and wrap his other around his neck, pulling him up into his chest until they were both vertical.
Turning his head to the side, they kissed as Dean's thrusts began to slow and his hand increased the speed that he was using to stroke his dick. Feeling a tightness, his orgasm hit like an explosion. His knees wobbled as he gasped and looked down, as ropes of cum shot out of his cock and painted the blanket they were on. He also felt Dean go rigid, and a warmth spread in his ass as his seed erupted deep within him. Dean dropped his head and bit down gently onto his right shoulder as he collapsed in a gasping and whimpering mess. He felt deep and shallow breathing across his back as he fell onto his stomach. Unfortunately he landed right on top of his cum that had soaked the blanket. At first he didn't care, but as they laid there and panted, it started to cool and the feeling became uncomfortable. Dean kissed his neck, and continued down his spine until reached his ass and began to lick and swirl his tongue around. It felt amazing, but his dick was done. It remained limp and spent, no matter the sensations that felt.
Trying to sit up, he was weaker than he had thought, for he fell right back to the blanket. Sighing, he turned his head back towards where Dean was sitting Indian style, watching him with a soft smile. Dean's penis was now flaccid, the foreskin covering the head again, which laid atop his nuts, which seemed to droop a bit more than usual. To be honest, he wasn't surprised. They had been so active lately it was a wonder he had any stuff left in his sack. He felt his own flaccid penis beneath him, sore with overuse, but he didn't really care. Crawling forward, Dean laid next to him, with a kiss to his cheek, and his hand brushing through his hair with affection. Smiling, he tried to shift over to him and laid his head on Dean's bicep, snuggling up close to his sweaty chest. Though they had showered earlier, the sweat and exertion from their activities were causing then to already stink. Dropping his head, Dean lined up their eyes and leaned to kiss him softly on the lips. Glancing down, he stared at Dean's member; which now lay to the side with the very thick bush surrounding the base.
"I think you're going to be rather sore tomorrow." Dean whispered to him, now smirking. Pausing he looked down because he had reached down and was fondling his junk with fascination.
"Tomorrow? I'm already sore right now." he replied as he reached behind him and rubbed his backside. Grimacing, he looked back into Dean's green eyes. Immediately, he wished he hadn't said that. Dean looked down, and he could tell Dean felt guilty that they did it. It had hurt, but no where near as it had the first time they did a few days ago.
"I shouldn't have done that to you." he whispered, so quietly it seemed he was talking to himself.
"Dean," he said, reaching up and taking hold of his chin and turned it so he had to look at him. "At first, it hurt like hell, but trust me, toward the end..." he smiled broadly and looked up, as if remember an event from a favorite time in the past.
Reluctantly, Dean smiled back and looked a bit calmer. Sighing in relief, he gave him a quick peck on the nose. The sun was beating down on them, making him sweat ever worse. Dean had his eyes closed now, with a smile on his lips. Looking around, he didn't see anything amiss, and then looked down at the drop from the cliff to the creek. It was maybe a bit higher than fifteen feet. He could make out the bottom of it, which was floored with flat rock and in a few places with gravel. There were no snakes or anything that looked dangerous. Shifting his gaze to look at the small depressions in the cliff that had been carved as hand and foot holes, he could see it would be easy to climb right back up. Smirking, he glanced down at Dean with his eyes still closed and figured he should do what he wanted to come here for. Without warning, pushed onto his feet, and dashed forward and glanced back. Dean had sat up and was watching him. Turning his back forward and took one last look below, and jumped.