The Neighborhood Bad Boy Takes Me

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."

It took a few more minutes of gentle sliding back and forth, but I felt my hole relaxing around him. He felt it, too.

"I'm gonna go a little deeper," he murmured. He braced his hands on both sides of me and pushed his hips forward. More of his cock slid inside and I could feel the head of his cock rearranging my guts. I grunted. "You ok?" he said.

"Yeah," I moaned. "I'm ok. I think."

He started to withdraw, just an inch or two, and then slowly pushed in. I moaned. He pulled back a couple of inches and slid back in. I saw his eyes close as he began to rhythmically pump his hips back and forth. "Ohhhh, yeah..." he moaned as he started to move in and out of me. I was grunting and breathing pretty hard as he slid back and forth.

"Are you ok?" he asked again. "This feels fucking amazing..."

"Yeah," I said. "Yeah, I'm ok. It's...fuck, it's really big."

He kept slowly moving in and out, and I could feel my hole loosening around him.

"Are you all the way in?" I asked

He laughed. "No. Well, at least not yet." There was that evil smirk again. He looked down at his cock. "'About halfway. Maybe four more inches to go."

He leaned down closer, and spoke quietly. "You want it?"

I swallowed hard. "Yeah, I think so. Easy though."

He gripped my ankles hard and spread my legs. He licked his lips. He gave a little grunt as he squeezed his ass muscles. I felt incredible pressure at my asshole as his shaft slowly ground forward. Inch by inch, he drilled his incredibly long cock into me and slowly slid all the way up inside me. I felt his crotch pressing against my ass as he sheathed over eight inches of rock-hard cock in my tight ass.

"Yeahhhhh," he moaned, pressing hard against me. "Ohhhh, fuck, that's so good."

He started a gentle pump-and-thrust pattern. He'd pull back, pump a few short strokes halfway in, and then slide into me, all the way, and press against me hard as his cock penetrated deep inside me.

"How hard can you take it?" he asked, pumping slowly.

"I don't know," I said.

"Let's find out," he said. He slowly pulled back, until half his cock was out of me. He gave me three or four firm short pumps and then pushed forward firmly, burying the whole shaft in me in one long, slow thrust. I groaned, but took it.

"How was that?" he asked.

"Ok. I think."

"Try again?"

"Yeah, easy though."

He pulled back, further this time, gave me a pair of short stabs, and then pushed in again, a little faster and harder. He waited a moment, then pulled out more than half way, and then shoved forward faster again. On the third stroke, he pulled back pretty far and this time shoved forward fast, going all the way into me in one smooth stroke. He pressed down hard, making sure his cock was all the way in. He went really deep and I could feel the hardness of his shaft way up in my guts.

Then he smiled. "I think you're ready."

I wasn't sure what he meant and he gave me no time to ask. He grabbed my ankles, spread my legs wider, and shifted his knees. My legs were higher and his hips were more on top of me than before. It took me a moment to realize he was trying to make it easier for him to plunge into me. Instead of having to use his hip muscles to thrust forward, he would be able to use his weight and gravity to drive his cock down into me.

He pulled all the way back. I could feel an emptiness left behind as he pulled his cock almost all the way out. Reversing, he pushed down slowly but firmly, sliding his cockshaft all the way into me. He pressed his groin against my butt for a moment, then pulled back again and pushed down again. He did it again, then started to move in and out without pausing.

"Oh yeah," he moaned. "This is fucking awesome... I knew you could take it."

I held on for the ride and tried to keep my legs in the air as he stroked and fucked. Suddenly I realized we hadn't said a word about how this would end.

"Hey, man," I said between thrusts, "are you close?" I asked.

"No," he grunted, plunging deep into my guts. He cracked a very nasty smile. "Well, not yet. But getting there."

"Are you gonna..."

He laughed. "Am I gonna what?"

"You know," I said, sheepishly.

"Am I gonna cum?" he said, with a huge laugh. "Well, yeah, eventually. Isn't that the whole point?" He gave me another stroke and then pushed in really deep and held it there.

"I meant are you gonna pull out," I explained.

"Ohhhh," he said. "I gotcha. Well, kinda depends on you. I'd rather not."

"You're not wearing a rubber."

"That makes it better."

"Yeah, but are you clean?"

"Totally. Tested a couple months ago, all clean."

He was still pistoning that huge shaft in an out of me. It was stretching me hard, but fuck it felt so good.

"So, what do you think? Can I cum in you?" he asked.

"Um, well, I... I mean..."

"I want to," he breathed, resuming his stroking. "It'll be awesome. Let me cum in you..." His cock was again moving rhythmically in and out of me.

I thought for a moment. It's not like I hadn't taken a few loads in me - or pumped a few of mine into someone else. And damn, his cock felt amazing. I decided to take the chance. "Ok, you can cum in me."

He smiled from ear to ear and pumped harder, now determined to trigger an orgasm.

"Mmmm, I'm gettin' closer..." he moaned, after less than a minute.

"It's really big..." I moaned.

"Yeah, man, super horny now," he said between thrusts. He smiled again. "Damn, you're so tight it feels like my cock grew to nine inches, unnnhhh..."

His breathing got ragged as he kept stroking in and out. His eyes closed and his mouth hung open as the waves of pleasure radiating up his hard, thrusting cock soaked his brain in sex hormones and endorphins. His brain and body were completely consumed with the urge to complete the sex act and ejaculate.

"Ohhhhh, fuck... I'm really close..." he moaned. His grip on my ankles tightened.

He stretched my legs way up, opening me completely. His hips became a machine, thrusting back and forth as he pushed for orgasm. My own head was swimming as I realized what was about to happen. That massive sex organ between his legs had one single purpose: breeding. Any moment now, it would fulfill that purpose and flood my guts with his DNA. He needed to cum, he wanted to cum, and he was going to cum. I couldn't stop him now if I tried.

He plunged down hard, pushing the full length of his sex deep inside me. I felt the huge column of flesh start to throb, and then he groaned loudly as he released. I could actually feel the seed tube on the underside pulsing hard against my anus and realized it was happening. He was shooting. Filling my bowels with his hot sperm. The warmth spreading up inside me...was him.

His entire body was taut for several seconds — ten or fifteen — then suddenly relaxed and collapsed forward onto me. He started panting for breath. I could still feel his cock throbbing and pulsing inside me. It seemed to be taking a long time for him to drain his full load into me and I wondered just how much there was. After a minute, though, he seemed to return to Earth, smiling hugely.

"Shit..." he said. He leaned back and started to stand up. His cock pulled out of me as he got on his feet. It looked angry and bloated, and it was still hard and twitching. A long string of semen dripped from the tip and fell on the bed. He grabbed a towel and wiped his organ clean.

"Fuck..." he whispered, cleaning the shaft. "That was awesome." He was strutting about the room, breathing hard.

I started to sit up. "Whoa, whoa, whoa," he said, diving towards me. I froze. He jammed the towel under my ass and held it against me.

"What?" I said.

"Uhh, I just shot a ton of cum in you, man, it's gonna leak out all over the bed."

"Oh."

"Give it a sec, let it run out in the towel."

I could feel his load moving inside me. I squeezed a little, and felt something wet and slimy spurt out of my anus.

"There...ok, there it is. Wow. Fuck, I creamed you good."

"A lot?"

"Oh yeah, it's a lot. Hold on, squeeze again." I did. More came out, and he caught it in the towel.

After we cleaned up, I dressed and went home.

****************

The next night, I was looking toward his house and saw him in the window. He waved his arm, inviting me to come over. I crossed the yard and slipped into the door to his room.

"Hey, guy." he said, "Um, so how about it, can we fuck again?"

I nodded. We undressed and I got into his bed. His cock, just half hard, was so long. I couldn't believe it had gone in me.

"I'm glad you came back. You felt so fucking awesome last night, I want to do it again!"

He laid me on my back and raised my legs. He reached for a small bottle. "Look man, lube. And good stuff. I wanted to make it easier." I felt him squirt some on my asshole and probe me with a finger. Then he squirted some into his hand and started rubbing it up and down his cock. It quickly stiffened, going from half-hard and hanging between his thighs to a rock-hard shaft of flesh, standing up at a high angle.

He saw me watching him get his cock hard. "You like that, huh? Watching me get it big and hard for ya, yeah?" He slid under my legs and pointed the head at my slicked-up bud. "OK, take a deep breath..." He pushed. My hole yielded easily thanks to the lube and his cock started to slide in really fast.

"Ow..ow..yeow!" I shrieked. He stopped. "Easy, man, you can't just shove it like that..." I moaned.

"Sorry, sorry, I'm really..." he said, a bit panicked. "Are you ok?"

I squirmed at the discomfort of being impaled by his dick. "I think so... just go slow, ok?"

"Yeah, man, of course. I'm sorry, seriously." He paused, unsure what to do next. "Do you want me to pull out?" he asked, clearly reluctant to do that and hoping I'd say no. I figured it would be worse to try to get him back in, and said, "no. Just gimme a sec to adjust."

He smiled big, realizing I wasn't going to make him pull out. "ok, sure, whatever you need." He held still while I took a few deep breaths and felt my hole start to relax around him.

"OK," I said, "I think I'm ok. Try a little more, but slowly."

"Ok, I'll go easy." He gently pushed forward, giving me another inch of his cock. "Ok?" he checked.

"Yeah, yeah, it's ok. Go ahead, a little more."

Over the next five minutes, inch by inch, he worked his tool into me until his hips pressed against my ass. "Ohhhhh, fuck..." he moaned. "It's all the way..."

I felt like he'd shoved a baseball bat in my ass. "Unnnnh," I moaned, "God you're big..."

"Yeah, but you like it..." he smiled nastily, starting to pump his hips.

As the night before, he started pumping into my ass, increasing the length and speed of his strokes until he was fucking me hard.

After a few minutes of stroking, he told me he was going to cum. He didn't ask if I wanted him to pull out or cum inside me again, but I guess he assumed that since I had been willing to take his load last night, there was no need. "Ohhhh, fuck..." he moaned. "Yeah... oh yeah... fuck yeah, here it cums... I'm gonna shoot..." and then pushed in hard. I again felt the rhythmic pulsation of his cock as it pumped his sperm into my guts. When he was drained, he slowly pulled his cock out. He held my legs in the air, staring at my asshole.

"What is it?" I asked.

"I want to see it leak out," he said. "I shoot a lot, and I want to see it." We waited. After a few moments, he still saw nothing. "Damn, man, I must have been in really deep. Still nothing." Another few moments passed, and I felt something wet and slimy at my anus. I tried to hold it in, but that only squeezed it out. "Yeah!!" he shouted. "There it is! Aww fuck, I loaded you good, it's a flood." I slid my hand down to my hole and scooped. His sticky, wet load slid into my hand. I looked at it. It was a huge puddle of semen. He really had shot a big load in me.

I rubbed it on his cock, feeling the spongy semi-hardness of the now-deflated organ that had, only moments ago, pumped that load into my body.

"Yeah, rub it..." he whispered. "Feels good." He grabbed my cock in his hand and started to stroke me. The lube and his hand felt good. I got super hard.

"You like that?" he said, with an evil grin.

"Yeah..." I moaned.

He stroked faster. It didn't take long.

"unh... unh... " I moaned, "fuck...gonna cum...". I shot, spilling my seed on his hand and my stomach.

"Super hot!" he said. "Hey, watch this..." I watched as he licked my cum off his fingers. He smiled as he pretended to savor every drop.

"Maybe next time you can just cum in my mouth," he laughed. "Or maybe I'll cum in yours."

"I kinda like it the way we did it," I said, putting my hand on his cock. He was soft, only about three inches long. But as I touched it, I felt it twitch.