I was seriously regretting the decision to spend the summer with my family. My first year at college had been one hell of a liberation, and I had enjoyed living on my own, keeping my own schedule, and not having to explain every night out with friends. Going away for the summer was like falling right back into being a kid living under my parents' roof, and it was chafing, badly.
I couldn't even try to break the boredom by looking up old friends from high school. I didn't have many, and I didn't have a "posse" or a group. I had spent a lot of time in high school confused about my sexuality. I liked girls, but was also attracted to guys, and it wasn't exactly a good time or place to figure it out. College had changed all that. I'd messed with both girls and guys and realized that I was bi. I actually had a girlfriend for a couple of months until we realized that I couldn't be exclusive; the sex had been really nice, and at least we were still friends. We even had a couple of friendly stress-relieving booty calls after we officially broke up, until she found a new boyfriend. There were two guys on campus with whom I'd settled on comfortable "friends with benefits" arrangements; we swapped a few blowjobs and sometimes went further. They were opportunities for a nice release, but nothing serious.
Being home, however, had taken even that away from me. I was missing my social life, and my sex life.
So there I was, home for the summer, sexually frustrated, and bored out of my mind.
And then I met the neighbor's nephew.
He was a senior in another college, visiting for a few days. He was loud, always talking big, and had a braying laugh that fit his wide, toothy smile. He was a troubled kid, constantly getting into trouble. His parents had sent him to his aunt and uncle to see if they could get through to him.
He was, in short, a complete ass.
And for some warped crazy reason, I thought that was hot as hell.
One evening, he was hanging out in their basement guest room. I crossed the lot to get away from the cocktail my parents were having for the "grownups".
I don't even remember how we got on the subject, but pretty soon we were talking about sex. I wasn't a novice, but he'd had a lot more than I had. Or at least he claimed it. I jokingly asked if he'd let me stick my dick in his ass to even up the score. Surprisingly, he laughed and said ok.
We ditched our pants and headed for the bathroom. He bent over the toilet and spread his ass. I took my hard dick, spat on it, and tried to push through his ass ring. He found some vaseline — all we had as grease — and put some on my dick. I really loved the feeling of his hand on my dick. He turned and bent over and I tried again, but kept popping out.
After a few unsuccessful attempts, he said "let me see if I can get in you."
I didn't know it at the time, but that had been his plan from the start. He had tightened his hole to keep me out, intending to suggest we switch places. He did, and, naively, I went along.
I couldn't see what he was doing, but could hear him rubbing his cock to get it hard. He used some spit to slick up my hole. After a moment, he pressed the head of his cock to my anus. He pushed, gently at first, then harder.
"Grease it," I said.
He withdrew, and I heard him putting the vaseline on his cock. A moment later he positioned it again, pushed. Nothing. He pushed harder and the head began to cram it's way in. A sharp pain shot through my butt. "Ow!" I cried. As he pushed again, I lost my balance and edged forward. The half inch he'd managed to lodge in me popped out.
"That didn't work," I said.
"Yeah," he said. "It's hard to balance standing up," I said. "Let's try the bed."
We moved back to the bedroom, and towards the bed. I turned and sat down, and that was the first time I really got a good look at his cock.
He was standing about fifteen feet away from me, taking off his shirt. He was already naked from the waist down.
I stared at his crotch and my jaw dropped. His penis, half hard, stood out from his groin at a low angle.
It was long. Really long. It was the longest I'd ever seen.
"Whoa." I whispered.
"What?" he asked, smiling.
"Um..." I stammered, just kinda staring at it.
"I know," he said with a huge shit-eating grin.
"That's huge," I said. "I don't know if it will fit."
"Nah, it will," he said, walking closer.
He reached the bed and put his hand on my chest. "Let's try." He gently pushed, and I toppled backwards onto the bed. I scootched upward until my head was on a pillow. He climbed into the bed on his knees. His cock swung between his legs.
"How big is it when you're, y'know...?" I asked.
"Hard?" he asked.
"Yeah," I said.
"Big," he laughed.
"How big? Like, um, six inches? Seven?" I pressed.
He chuckled as he opened the vaseline, scooped some out, and started rubbing it over the head of his cock.
"Eight-and-a-half inches," he said proudly, spreading the goo. "Well, that's if I'm really horny." My eyes widened.
With his right hand he squeezed his cock, masturbating it. I watched as it got longer and harder. When he took his hand off it, it slapped up against his stomach. That half hard-on was now rock-hard and ready to fuck.
He lifted my right leg, moved closer. I raised my left leg and balanced it on his shoulder. He scooped out another gob of vaseline and pressed it to my anus, and then put a huge glob of spit on my hole. Then he grabbed his cock and angled it toward my tiny rosebud.
"I really... I don't know if..." I stammered.
"Only one way to find out..." he said, moving into position. He placed the head of his cock at my hole, spat on it, shifted his knees, and aimed. "Ready to try?" he asked.
I was nervous. I could feel the heat and hardness of his cock pressing in. "Can I try?" he asked again.
I nodded. "Um, yeah, ok. Go slow, ok?"
He smiled toothily, almost wickedly, and hissed "yeah!" I felt him start to lean in. His cock was pushing, but my hole was resisting. He wiggled it, stroking my hole. The pressure was incredible. He wasn't the first to stick a dick in me, but he sure had the biggest cock that anyone had ever tried to shove into me.
He continued to swirl the knob at my hole, pressing harder. Then harder. He started leaning forward, using his weight to try to force the head in.
Suddenly, I felt a painful pop and felt like my hole was being forced open. I howled in pain and surprise as the head burst through my ring and several inches of his cock shoved inside. He sighed and groaned, closing his eyes and smiling as his cock penetrated.
"Aiiiieee, oh, oh, ohhhhh!!" I shrieked. He stopped his advance. "OK," he said, "easy... Take a moment to get used to it." I was panting and squealing at the invasion by his shaft.
After a while, he said "I'm going to move." He pressed forward gently and I felt his cock slide a little deeper. It was sore, but less painful. "You ok?"
"Yeah, yeah, I think so. It hurts some. Fuck, you're big."
