Jon and Chris' Trip to the Cabin Pt. 02

Jon grabbed the scotch, and they headed inside. They grabbed towels, and Chris started toweling Jon down. Jon was a little surprised, but enjoyed the rub down, and returned the favor. They rubbed each other's bodies, and Jon was stiffening up from the soft towel and rough treatment. He was surprised; normally it took at least a half hour to get hard again. But the combination of getting rubbed down, doing some rubbing himself, and the taboo nature of the whole thing had him horny and excited. He was breathing a little fast, felt the blood pumping through him. Chris then led the way into the master bedroom.

The bed was a king, with a big white down comforter. Chris opened up a nightstand and grabbed a bottle of lube, while Jon pulled the comforter off the bed. They both were new to gay sex, but had had experience with anal before. They jumped into bed. Jon pushed Chris onto his back, and on hands and knees, started sucking Chris' semi back into a raging hard on. He had a cock in his mouth for the second time tonight, and he loved it. Jon was a little less apprehensive this time, and grabbed the shaft in one hand, stroking it, while he sucked the head. It was fantastic, feeling Chris grow hard in his mouth. Chris was starting to thrust his dick into Jon's mouth, and Jon tried to move with it. It was more difficult than he thought! They found a rhythm, and Jon had to remind himself they weren't just going to blow each other again. He kept going, figuring that while he was excited to try something new, he figured getting Chris a little closer to the goal line wasn't a bad idea. Finally, he came up for air. He looked at Chris, and said something he never expected to say to another man. "Fuck me!"

Chris scrambled up, clearly excited. "How do you want to do this?"

"I don't know," Jon replied. "I figured I'd get on my knees, and you could take me from behind?"

"Sounds good. I have condoms somewhere..."

Jon waved him off. "I don't have anything, haven't been with anyone but Michelle since the last test. You?"

"Just the wife."

Chris moved behind Jon, and Jon got himself in position, ass in the air. He was so nervous, but also excited. He jumped when he felt Chris' finger on his hole, then relaxed when he realized Chris' was just lubing him up. Jon looked over his shoulder to see Chris stroking lube onto his cock, and then lining up to penetrate him. Jon reached back and touched Chris' thigh, stopping him. "Gently, dude. First time."

Chris nodded. He was breathing as hard as Jon was. Jon turned forward, and waited anxiously. He felt the tip of Chris' dick touch his asshole, and then pressure as Chris pressed forward. Chris got nowhere, and told him, "Relax."

Jon realized he was clenching, tight with apprehension. He took a deep breath to relax, and then another. As he was doing that, Chris pushed. Jon arched his back, and tried to open himself up to this. He was trying not to think about it, but he couldn't help himself. He was trying to make it easier for a guy to fuck him in the ass! He was making it easier to get fucked by a hard cock. He quickly lost his train of thought as the pressure became pain, as he felt himself getting ripped open as his friend's dick pushed into him. "Fuuuck!" he yelled, the pain of having a cock pushed inside him for the first time.

Chris stopped. "You okay?"

Jon was breathing hard. "Give me a second."

Chris waited, and Jon started moving around a little, getting used to the feeling. It hurt, he realized, but in kind of a good way. After a couple of breaths he nodded. "Okay, just slower."

Chris started pushing again, and gritting his teeth, Jon felt inch after inch slide into his ass.

"Okay, I'm in."

"Fuck, you have a huge dick."

Chris laughed, which felt so weird to Jon. "I appreciate the comment, but I think your virgin ass would think anything was huge."

Chris was patient, and Jon kept moving and flexing, getting used to what was happening. Finally, he started moving, gently sliding Chris out a little and then back in. He was fucking himself on Chris' dick!

Chris started moving together, and the two of them found a gentle rhythm, slowly sliding a little more of Chris' cock out, then back in, out and back in. It hurt, and Jon was dead soft, but after a couple of minutes, the pain diminished, and pleasure joined in. Getting ass fucked wasn't as bad as Jon had assumed. There was definitely something enjoyable about it. Chris seemed to sense Jon's acceptance, and slowly picked up the pace. Soon, Jon was getting hard again, and could enjoy some of the experience. The feeling of Chris' balls slapping against him, the hardness plunging into him, the idea that he was being used for another man's pleasure, they were all turn ons he never expected.

Chris started to increase the speed and power, which hurt, but Jon didn't want him to stop. He was rock hard, in fact was starting to hurt from how hard his dick was throbbing, when Chris stopped. Chris pulled out, and grabbed Jon's hip, flipping Jon onto his back. Jon readily complied, and lifted his legs as Chris edged up to his ass. Chris' face was red, sweat dripping as he lined his cock up again with Jon's tight hole. Jon lifted his head up, trying to watch as Chris slide inside his ass. Jon's cock was straight up, and it jumped repeatedly as Chris worked his way back into Jon. Once in, Chris started pushing again, and soon, Jon was getting fucked, but this time, got to watch! The sight of his friend pounding into his ass was so unexpectedly hot, Jon grabbed his cock and starting stroking it. Chris' dick hurt Jon's ass so much, and felt so good, the cock being shoved into his ass, and he couldn't help but jack himself. Jon had never felt his own shaft this hard before.

Chris was nearly out of control now, fucking Jon so hard, and it was too much for Jon to handle. He tried to say something but couldn't, he just let out a moan. Chris seemed to draw inspiration from this and kept pumping, fucking Jon's ass, and Jon just had to grit his teeth and take it from this man. Jon was gripping the pillow above his head, stroking himself with his other hand, when Chris started reaching his peak. Jon was getting close himself when he felt Chris tighten up, pump hard, and then explode. Chris groaned as he came, shooting blast after blast into Jon's ass. Jon was stunned to find he could feel it, feel as Chris exploded in him, and the idea of his friend, of a man, using his ass until he came, pushed him over the edge. As Chris was finishing his orgasm, Jon's started, and he shot ropes of cum onto his chest and stomach. It was one of the most intense orgasms of his life, his cock jumping and shooting cum.

Chris slowly pulled out of Jon, and collapsed next to him. Jon's legs ached as he lowered them, and he couldn't believe how much his ass hurt, and how amazing he felt. Normally after cumming, Jon felt a huge letdown, and often passed out in minutes. Instead, he felt energized. He was exhausted, but exhilarated. After a few minutes, Chris sat up to look at him.

"Holy fuck, that was hot."

Jon smiled. "What happened to gentle?"

"Sorry, man, but that was amazing, I couldn't help it. Fuck, your ass is tight."

They lay there for a little while longer, and then Chris grabbed another towel out of the bathroom. He cleaned Jon up, then lay beside him. "So," Chris asked, "how was it?"

Jon arched an eyebrow. "Are you nervous about your performance?"

Chris smacked him. "No, asshole, how was getting fucked in the ass?"

Jon sat up a bit, moving his head onto a pillow. "It was painful, and hot, and it felt terrible and I didn't want it to stop. It was bizarre."

"Did you like it?"

"Did you see how hard I came? I can't believe you came inside me."

"Uh, yeah." Chris shrugged. "Couldn't help it. Was that a problem?"

"No," Jon reassured him. "I was just surprised. It was fucking hot."

The adrenaline rush and then crash, the hot tub, the scotch, all came together, and soon the boys found themselves falling asleep. They passed out together, both satisfied at how their night had gone.