As a teenager, I hung out with a neighborhood kid that went to another school name David. He was from a big Italian family and had the dark smoldering looks that some people find hot. I wasn’t so turned on by his being Italian but by the fact that he was cute and fun. We were always having staring contests and there was lots of physical contact. We never did anything sexual but sometimes we would sprout wood while wrestling and we’d laugh about it.

We used to ride and hike all over the woods and trails in our town and were almost constantly outdoors. Whenever we had to piss we both used the opportunity to surreptitiously check out each other’s equipment. I wanted to do something with him so bad that when he would brag about how big his dick was I’d say “doesn’t look that big to me.”

He’d respond with “you’ve never seen it hard.”

“Whip it out then” was my comeback.

He responded “You just wanna see my dick” and of course he was right. Even though we had many sleep outs and camping trips I rarely got to see David naked and I never got to touch him the way I wanted to. Eventually we drifted apart and though we’d see each other occasionally we didn’t hang out like we used to.

Fast forward a few years... One night a few months after high-school graduation, during my first college semester, we were hanging out in the same bar (when you could drink at 18) and got reminiscing about how when were were younger we would sit in my dark basement, listening to Led Zeppelin and getting stoned.

“I’ve got some really good weed if you want to burn one” he offered.

I was up for it and said “let’s head to my house, we can listen to some music.” We smoked in the car on the way to my house then went up to my room and put on some music. We were laying on the floor in opposite directions, propped up on elbows facing each other and chatting mindlessly when he caught me staring at his crotch.

“You wanna blow me?” he asked, breaking my trance.

I laughed and asked “why’d you say that?” even though I knew I was busted.

“You’re staring at my dick” he said with a smile. I’m not sure what came over me next - alcohol, pot, lust or all three but my response surprised both of us.

As if in a haze I said low and slow “We never did anything when we were younger.”

David scrunched his brow and replied, “like what?” Now I had to keep going or get creative really quick to avoid something awkward. I kept going.

“You know, like play around, like younger guys do” was my explanation. “Did you ever do anything with Kevin or Gordy?” I asked.

They were mutual friends of ours that lived next door to him. “Nothing more than jerking off” he admitted.

“You always bragged about having such a huge cock” I laughed.

“And you always wanted to see it” he said. I couldn’t deny that so I responded that I just wanted to know if he was telling the truth.

I don’t know if it was me staring at his crotch or the conversation but something had gotten him slightly excited because the bulge in his jeans was a little bit bigger.

David reached down, squeezed his cock through his jeans and said, “the girls love it.”

Well in for a penny, in for a pound I thought and decided to keep pushing it. “How big is it?” I asked.

“About 7.5-8 inches” he replied.

“Yeah right!” I laughed, “prove it” I challenged him. He laughed and shook his head then to my surprise he started to unzip his jeans. The bulge I had stared at through denim was now visible through his underwear and looked bigger than ever.

He slowly rubbed his cock through his underwear and then slowly pulled the front down to reveal a dick that looked absolutely huge on such a slim, small (5’5” tall) guy. It was at least 7” and thick too. I was transfixed and he knew it.

“You wanna touch it?” he asked with a sly grin. He already knew the answer and so did I. I reached out slowly and wrapped my hand around it. It was the biggest cock I had ever seen up to this point. I slowly stroked him up and down and his head rolled back as he enjoyed the sensation.

“It’s huge” I said, with an air of wonderment.

As I continued to stroke and squeeze it David whispered “you wanna suck it?” and I knew I did. I just didn’t want him to know that.

“I don’t know” I lied, “I’ve never done this before” I lied again. But my actions betrayed my words. I was slowly leaning toward David’s cock, staring at it, unable to take my eyes off it.

“Just watch the teeth” he instructed as my lips neared his massive meat. A pearl of precum showed that he was excited too. I licked my lips and tentatively took him into my mouth. I got about halfway down and came back up. This thing really is big I thought.

“Use your tongue” he instructed again. Of course I already knew that but the reminder didn’t bother me. I started to bath his dick with my saliva and get a rhythm moving up and down. “Oh yeah” he moaned.

In the mean time I had opened my pants and was playing with my own dick while I serviced David’s. He reached toward me and I thought he was going to grab my dick but he bypassed that and started rubbing my ass. The sensation of his hand on my ass and his dick in my mouth made me shift gears and start to suck him even harder.

“Ugh, oh my God. I can’t believe you’ve never done this before” he moaned.

“Is it good?” I asked, knowing that it was. I just wanted to hear it from him.

His reply of “hell yeah” turned into a moan as I sucked hard again on his throbbing member.

As his hand was exploring my backside I took his cock out my mouth just long enough to ask “you wanna play with my dick?”

He quickly replied, “nah, not into it” but he kept playing with my ass, caressing it.

“Well I’m doing this for you. How about you do something for me.” I stated matter of factly.

“Like what?” was his reply. If he wasn’t going to touch my dick I had no idea what he could do for me but fair is fair, right?

As my mind was working on an answer his finger slid between my ass cheeks and grazed my hole. With my mouth full of his cock I let out an involuntary moan, “ugh” which he immediately picked up on.

“How about I fuck your ass” he said with his trademark sly grin.

For a split second it sounded like a great idea until I remembered how big his dick was and that I had never had a dick in my ass before. “No way that thing is fittin’ in my ass” I said.

But David’s smile grew bigger as he asked simply “why not?”

I told him “I’ve never had a dick in my ass and your dick is huge” which only seemed to make him more determined.

“C’mon, it’ll be hot. I’ll take it easy” he promised. He was melting my defenses.

Looking him straight in the eye I said “seriously, if we do this you gotta go slow, I mean it.” At that point he knew he had me.

“You got some lube?” he asked. I went to the bathroom and grabbed the vaseline.

“Suck it a little more first” he said and I was happy to comply. “OK, that’s enough” he said, pushing me off his dick and directed me to get onto a nearby beanbag. He lubed his dick and I lubed my ass. I put my ass in the air and he got in position.

The first touch of his dick to my hole was electric. I wanted him inside me but was terrified of it at the same time. He pushed in and I pushed back. “It’s too big” I complained.

He rubbed my back and quietly whispered “just relax” as he kept pushing. And then it happened - his head popped in and I was immediately in pain.

“Oh my God. It’s too big. Take it out” I said.

“Shhh, just relax” he said again as he held still for a minute before applying more pressure. A few minutes later my ass muscles relaxed and he was slowly sliding all the way in. I could take him being in me but when he started to pull out and push back in it was too much.

“It’s too big” I said again, letting him know this was hurting me.

Instead of telling me to relax David said “It’ll get better. Oh my God, this feels so good. Your ass is sooo tight!” and he very slowly started moving in and out of me again. My ass went from feeling splitting pain to just feeling numb to feeling something that made me want to keep going. I started to push back against him.

I was starting to get into it and talk dirty to him. “You like that tight ass? Fuck me!” My moaning was getting louder and David had to remind me that there were people sleeping in other rooms and we needed to be quiet.

It wasn’t easy being quiet with a huge dick in my ass but I wanted to make him cum. As David continued thrusting in and out of me I started to work my ass muscles. He definitely liked it.

“Oh yeah. Squeeze my dick. Just like that. Keep doing that” he said between swear words and labored breaths. His sweat was dripping onto me. His chest sliding up and down my back as his big dick was punishing my virgin ass.

The pain never went away completely because of my anal inexperience and his big dick… but the fact that David was plowing my ass and obviously really enjoying it was SO hot. I wanted him to remember my ass as the best fuck he’d had yet so I squeezed his huge cock the best I could as he pumped into me like piston.

David was grunting and swearing as he fucked me. Then he announced “Ugh, I’m getting’ close.”

“Cum in my ass” I begged. Looking back, I guess he had been fairly gentle fucking me because he didn’t want to hurt me but now he was out of control, hammering my ass for another minute before I felt his chest on my back and his arms wrap around my torso.

“Ugh, Ugh, UGH!” he was groaning then he just froze. A second later he exploded. His hips slammed my ass one last time and I could literally feel every throb of his cock as he blasted my guts with his teenage cum. His orgasm seemed to go on forever. “Oh fuck, oh fuck!” he moaned.

David collapsed on my back, breathing hard and saying ”wow, that was fucking incredible.” I squeezed his still-hard dick a few times prompting moans of pleasure. “Damn,” he moaned, “keep doing that, fucking incredible.”

As our breathing returned to normal David’s softening dick slipped from my ass leaving a void that felt huge but in a way, really good. Not only had I just been fucked for the first time, it was by a boy who I always wanted. I finally got his dick in my mouth. I wasn’t expecting his dick in my ass but what an experience!

For the next couple days I literally could not sit in class or walk anywhere without my ass reminding me of David’s big dick. That was the only time we ever messed around but it was so intense that it is a memory I’ll never forget.

My next adventure was with another neighborhood friend who was nothing like David. Brian was geeky and I never viewed him sexually until a late night road trip. But that’s another story.