The Lawn Rangers

The day after our visit to the adult bookstore, John came over to help me start stretching my asshole. I had decided it was time to let him fuck me in the ass.

My parents were both at work, and my brother was at school. John knocked on the door, and I answered it already naked.

John looked really excited. He was ready to help me use the dildos.

"We can only fuck around with this for about an hour," John said. "We have 11 lawns we need to take care of today."

I nodded and walked towards my room in front of him.

"Dude, you have a nice ass," John said.

"So do you," I replied.

"I have a little surprise for you," I told John.

"Oh yeah? What's that?" he said.

I bent over my desk chair and told him to check out my asshole. The truth was I started playing with the dildos and butt plug the night before.

John audibly moaned when he realized I had the small butt plug already buried in my ass. I had spent the morning walking around with it in my ass.

"It's weird," I said. "My dick will get rock hard and then soft over and over because of the butt plug, but it feels pretty damn good."

I felt John grab the end of the plug. I thought he was going to pull it out, but instead he started working it around. A quick flash of pain, followed by intense pleasure hit me.

I moaned out load and realized I was involuntarily rotating my hips.

"Yep. You have a real nice ass," John said out loud, to no one in particular.

He kept working the plug for about five minutes or so before he slowly started pulling it out. When the widest part was really stretching my asshole wide, he slowly reinserted the entire thing. It felt wonderful. John continued to fuck my ass with the small butt plug for another five minutes.

"Let's get the medium dildo in there," he suggested.

The dildo was thinner than the butt plug, but at least two inches longer. John lubed up the dildo and spread a generous amount of lube onto my asshole. I was bent over the chair to give him easy access.

I was surprised at how easily my asshole accepted the dildo, but after the first five inches, John had to really work it in. I moaned out loud again. It felt great, if not a little painful.

Suddenly I felt a pair of lips on my ass cheeks. John was kissing my ass. He took turns licking and gently biting it, too.

"I can't wait to fuck this ass," he said.

"I can't wait for you to fuck this ass, either!" I said.

I was getting tired of standing and told John that I wanted to get on my bed. He pulled the dildo out of my ass and let me get ready again.

"Do you want to go bigger?" he asked.

"I dunno dude. This one feels really good, but it's already hurting," I said.

"This dildo is just a little bigger than your own dick, and I took that bad boy without this much priming," he said, slightly annoyed.

I closed my eyes and slightly raised my ass into the air in doggy style.

"OK, go to the next one," I said.

The next dildo had ridges on it and was at least eight inches long and slightly thicker than the first. I could feel every ridge as it penetrated my asshole ring. I knees buckled every time a ridge made it through my asshole ring, too.

"Dude, you are leaking cum like crazy," John said. "Can you turn over?"

I did as he asked. John kept fucking me with the dildo the entire time.

When I was finally on my back, John lowered his head and started sucking my dick. It was an intense feeling having my ass fucked by this dildo, while he was sucking me off.

Without warning I started to cum. Spray after spray of cum shout out of my rock hard dick. It was perhaps the most intense orgasm I'd ever had, better even than the one on the bed of my pick up.

"Damn! You came more than I've ever seen!" John said.

He tried to clean my up with his mouth, but eventually gave up and cleaned me up with a towel I'd brought with me.

"Do you want to stop now or should I keep fucking you with the dildo?" he asked.

I told him I was done. We had properly stretched my asshole quite a bit. One more session and I'd be ready to let him fuck me.

I was totally worn out so I told John to jerk his dick and shoot into my mouth. I wanted to taste his cum. He stood up, dropped his pants and jacked his huge dick. I massaged his legs and ass before he shot out a nice, big load directly into my mouth. It was hot and creamy. I swished it around my mouth and enjoyed the flavor before swallowing it. I leaned forward and licked his cock head clean.

We both cleaned up and headed to work. As usual we easily went back to friend mode, casually talking about football season starting and other nonsense. We had both convinced our parents that we wanted to take a year off from school to try to grow our business. We were both making about $500 a week at this point and were actually having to turn down work.

As we finished up for the day John got really chatty.

"So what's the deal for my birthday?" he asked.

"Well I figured we could go to my grandfather's cabin for a few days. I'd have Claudia come up the second night," I replied.

It was understood that the first night was play time.

"That sounds hot dude. Any chance you can get her sister up there too?" he asked with a chuckle.

Claudia was an identical twin, although for some reason her sister always seemed slightly hotter. She had graduated on time and gone off to college a year before Claudia and us.

"Ha! Don't I wish," I said. "You know she claims she's made out with her sister."

"Ah, hell no!"John said. "Are you serious? Is she serious?"

"I don't know man," I said. "It might be something she said to get me hot one night. I can never tell. She's certainly freaky enough, but I don't know her sister very well."

The weekend of John's birthday finally came. That Friday, we packed up the pickup truck and headed for the hill country where the one-room cabin was. It wasn't the nicest cabin I'd ever seen, and it was small, but it was nice enough, and it had a nice bathroom. The weather was getting cooler, but was still warm enough where you could get in the water if you wanted.

We stopped at a truck stop to pick up the last of our necessities.

"I'm so excited about this weekend!" John said. "I haven't jerked it in two days!"

"Wow! Two days?" I said sarcastically. "Well I've been getting myself ready if you know what I mean."

John smiled big time. He knew what I meant.

When we finally arrived at the cabin it was lunch time. We unloaded the truck and got comfortable on the couch.

"So buddy, what should we do first?" John asked.

"I dunno dude. If we start playing around we could lose the entire day. I mean we have all night for that right?" I said. "But then again, it is your birthday so why don't you pick?"

John got a pensive look on his face. It kind of made me laugh a little that he was giving it so much thought.

"I've wanted to fuck your ass for a long time...." he said trailing off. "So let's do that!"

I laughed and told him I wanted to clean up. I went to the bathroom to do just that. I'd bought some new underwear for the occasion. Claudia had unknowingly helped me pick them out. I put on some cologne, too. If I was going to get fucked in the ass, I wanted to look and smell good damn it!

I walked out the bathroom and John was already naked and stroking his dick. He'd emptied out a backpack I'd packed with our sex supplies. I'd been practicing taking the dildos and butt plugs as deep in my ass as possible, but I knew this would be different.

John gave me a sexy whistle when I came out.

"I like those drawers," he said. "They're kinda tight around your sack. Turn around."

I did as he asked. The new underwear was just as tight around my ass.

"Dude, your ass looks really good," John said.

I walked over to him and pushed him onto the bed. We kissed and fondled each other for several minutes. A wet spot had formed on my crotch.

I kissed my buddy's neck and continued to lick and suck all the way down. I had started to really get off to sucking and biting his nipples, too. I kissed down his smooth stomach and worked my way down to his dick. It was as smooth as his balls.

John moaned as I started working his knob with my mouth. I had gotten pretty good at sucking his cock over the last three or four months. I loved nibbling up its side and gently biting it. I used my hands to rub and squeeze his big nuts, too.

John leaned back and put his hands behind his head. He looked like he was in heaven.

After a few minutes of sucking his big dick, I pulled off of it and worked my way back up. We kissed for a few minutes before I began to nibble on John's ear.

"Fuck me in the ass," I whispered.

John got very animated as he jumped off the bed and grabbed the lube.

"You need to work your fingers in there and get me nice and lubed before I'm going to let you put that monster in me," I said.

"No worries," John said, as he squeezed a glob of lube onto his fingers.

I tried to relax my ass knowing what was coming. A few seconds later I felt his finger rubbing the entrance to my asshole. I relaxed as he pushed his finger through. I had gotten pretty good at accepting things into my ass, but was worried about the size of his dick.

After just a few minutes he had worked two fingers in my ass with ease.

"Do you want to use one of the dildos before we fuck?" John asked.

"No, it's time. Fuck me," I said with my eyes closed.

John flipped me around doggy style and got behind me. He massaged my ass for a few seconds before I felt his big dick head at my entrance. I winced as he started pushing. A flash of pain went through me and I bit down.

My lover took his time. After what seemed like an eternity he stopped pushing.

"OK, the head is in," he said.

I laughed out loud.

"The head?" I asked. "JUST the fucking head?!"

John massaged my ass and kept working lube onto his dick as it entered me. After about five minutes I felt my asshole relax. At this moment his dick began to enter me much easier. When he had about 2/3 of his dick in me he warned me he was going to start pulling out.

I was feeling a strange mix of pain and pleasure I didn't realize existed. I tried to breathe to lessen the pain, to no avail. Just when it felt he was going to pull completely out, he started pushing his big dick back into me. I lost my breath again.

"Dude, I don't know what it's supposed to feel like, but your ass is super tight," John said.

"Does it feel good?" I asked, holding my breath.

"Oh yes! It feels great!" he replied.

Although I knew he couldn't see me, I smiled wide at that comment. I was happy I was making my friend happy. At that moment I tried to start playing through the pain and giving my friend a memorable first fuck. I started shaking my hips and pushing back onto him.

"Oh yeah," He said under his breath.

"Spank my ass," I said.

John obliged. He started out spanking me softly, but quickly worked his way to spanking me very hard. To be honest the pain of the spanking was keeping me distracted from the real pain of getting fucked in the ass by a subway car.

It had been 20 minutes since John had started fucking my ass. He had finally gotten to the point he was able to actually fuck me. He fucked my ass slowly at first, taking time to spank me. Eventually he was fucking my ass with reckless abandon. My ass was now numb from the fucking and spanking.

"Fuck me! Fuck me!" I shouted. "Fuck my ass!"

John fucked me as hard as he could. I squeezed my ass cheeks together in an effort to give him a good fuck. John was now grabbing my shoulders and ramming his entire monster into me.

After a few more minutes I felt his dick throb and John shouted he was cumming. I felt a warm flash in my bowels, which I assumed was John's hot cum. I was pushing back into him to increase the penetration. John pushed into me a few more times before collapsing on top of me.

My knees gave way as he pancaked me onto the bed.

His breathing was very heavy. I continued to squeeze my asshole around his big dick while he took a breather on top of me.

"That was fantastic," he whispered into my ear.

He then rolled off of me. His dick pulled out of my ass. It was a strange sensation, made only stranger by the fact that my ass now felt incomplete without his big dick in it.

There had been another flash of pain as his dick exited my ass, too. I could feel his hot cum oozing out of my ass. I turned my head to look at my lover. His eyes were closed and he seemed to be falling asleep.

About an hour later my eyes opened and I realized we had both fallen asleep. John was slightly snoring. I began to get up and realized my ass was on fire. As I worked my way up I realized that John's dick was rock hard again, standing up proudly.

It was so fucking big. As much as it hurt, I'd loved my first ass fucking. I looked around and found the lube. I squeezed some out and began to coat my buddy's big dick. John moaned as he felt me jerking his meat.

I pulled him towards the center of the bed and proceeded to see if I could ride his big dick. John woke up as I pulled him and looked around.

"Get in the center of the bed," I said.

"Why?" John asked.

"Because I'm going to ride your big dick," I said.

John immediately did as I said.

A big smile broke out on his face.

"Dude, I can't believe what I've been missing! Fucking is great!" he said.

He made me laugh.

I tried to lower myself on his dick the way he had in my truck bed a few weeks earlier. He held it steady for me. His cum was rolling out of my ass and onto his dick.

"Well, an asshole is way tighter than a pussy, but fucking a pussy is nice too," I said a bit distracted.

Eventually I was able to line up my asshole with his dick. At that point I started lowering myself. Again I had a flash of pain, but not as intense this time.

After just a few minutes I had completely engulfed his dick with my ass. He was balls deep in me. I struggled to raise myself up so I could begin to fuck him. Seeing me struggle he offered his hands and arms to me for balance.

I smiled and held on to his hands. This made riding his big dick easier, too. I felt like a total slut riding my friend's big dick, but I loved every minute of it. At one point I leaned forward to relieve some of the pressure on my back. Suddenly I realized that his big dick was now rubbing against my prostate.

John let go of my left arm to use his right hand to jerk my dick. It felt great.

I almost lost my balance at that point as I tried to continue fucking my friend. A few strokes later, without warning, my dick started shooting thick white cum. I was having an orgasm. My cum shot out and covered John's chest. I fought to keep my balance as John squeezed the last few drops of cum from my dick.

"Oh fuck dude, I'm cumming!" John said about a minute later.

I did my best to continue riding him so he would be able to cum too. It was difficult as my legs were like taffy. Every time I dropped onto my friend's dick it would poke my gland. White cream kept oozing out of my dick forming a small puddle on my buddy's abdomen.

Suddenly I felt his hot cream deep in my ass. John's face was clenched as he tried to fuck my ass from his position. I kept bouncing up and down his hard dick for another half minute. He eventually collapsed onto the bed. I slowed down and gently raised my hips up to release his dick. My asshole felt completely stretched and open.

I plopped down on top of John. We both fell asleep four hours.