It was mid-May in 1991 and I was just a few weeks away from my high school graduation. My parents were away for a couple of days to go to an automobile racing event a few hours away. As such, my sister and I made an arrangement for her to go away with her boyfriend for a couple of days and I could have the house to myself.

I didn’t really have a steady girlfriend at the time, so I decided to invite my two closest friends over for a night of drinking and whatever craziness that would come.

Jason was the first to arrive at my house at around eight-o-clock in the evening. I met him at his car and helped him carry his stuff inside of the house. Fortunately, he had managed to acquire a six-pack of beer along with a large pizza. I compensated him for half of the cost and we quickly headed to the kitchen table.

As we were enjoying both, we began to joke about our friend Aaron who had not yet arrived. We wondered how late he was going to be and assumed that he was going to quickly volunteer the info that he didn’t have any money to chip in for the pizza. At least we didn’t have to worry about him drinking our beer. We already had a short supply, probably enough for the lightweights that we were, but it would definitely all get consumed.

We had pretty much finished eating when Aaron arrived. He was about a half-hour late, which was earlier than either of us thought that he would be. We noticed that he hadn’t brought anything with him. We asked him where his bag was and he claimed to have forgotten it. We were pretty sure that he had just forgotten to pack it.

Aaron quickly spotted the pizza box and settled down at the table. When he opened the lid, you could see the disappointment on his face. We had purchased an all-meat pizza and Aaron always wanted pepperoni and nothing else. I slid a paper plate over his way and he put a slice on it. He stared at it and picked around for a bit, pulling everything that he could find off of it except for the pepperoni. He kept asking what the other toppings were as if he had never seen ham or sausage before.

After one bite, he asked me for something to drink. I told him what kind of soda we had in the fridge and he finally picked one. He managed to get through one slice of pizza, then he picked up another one and ate one bite of it, and was done.

I could see that Jason wasn’t very happy with him, but it was pretty typical of our group. The three of us had been close friends since kindergarten and we pretty much knew what to expect out of each other.

I cleared the pizza off of the table and put it in the fridge. I grabbed two more beers for Jason and myself as we had each finished our first beer. We decided that we were going to drink the last two beers pretty quickly so that we would get maximum impact.

I looked at Jason and asked, “Up and down the river?”

Jason nodded and I grabbed a deck of cards. ‘Up and down the river’ was our most frequently played drinking game, mostly because it didn’t have very many rules and it only required a deck of cards. It was also the most quickly intoxicating game that we played.

I dealt out four cards to both of the guys and myself. Aaron started to immediately protest, saying that he wasn’t going to drink and that he didn’t know how to play. We quickly explained that he didn’t have to drink beer and that we would tell him exactly what to do. There really wasn’t much strategy involved and everybody’s cards were always face-up anyway.

Aaron continued to protest and acted like he didn’t want to play, but we finally convinced him to try it. Jason and I agreed that Aaron would have to drink soda instead of beer like the two of us. We also made a non-verbal agreement that all of the larger drinks were going to go to Aaron since he was being such a bitch about everything. We knew that our two remaining beers were going to go quickly no matter how we played anyway.

As we played, Jason and I managed to force Aaron to drink a couple of cans of pop. He was the first to hit the bathroom, which we found rather funny. We started to joke that we were going to make him have to use the bathroom every fifteen minutes for the rest of the night. Shortly thereafter, Aaron started cheating and not actually taking drinks when he was supposed to or just making a slurping sound. It was pretty lame.

We called him out for cheating, but he kept on not taking drinks for the rest of the game. We continued playing until our beer was gone. As we wrapped up the game, Aaron started asking if we had anything else to eat. When we said that we didn’t, he started acting like he was going to go home.

We headed outside for a while and joked around for a bit. It was a really nice May evening, around 70 degrees and comfortable. Jason and I had a decent “buzz” going on by that time and we were pretty happy and giggly. Aaron still seemed uncomfortable with the whole drinking situation, even though we were done at that point. Shortly thereafter, he hopped in his car and went home. I told him to come back later if he got bored, but I didn’t expect that would happen.

Aaron hadn’t even left the driveway and Jason mumbled, “I’m glad that he’s gone. What a lame-ass!”

As much as I mostly agreed with Jason, I did feel the need to defend Aaron slightly. It was always nice to have Aaron around to protest all of the crazy stuff that Jason wanted to do. Jason was known to get pretty out of control and I think that every time that I had a run-in with law enforcement, Jason was involved. At least on this occasion, we were at my house and not out somewhere that we were going to get in trouble.

As soon as Aaron had left, Jason took off his shirt. I didn’t think much of it until he started trying to pull his shorts and underwear down over his shoes. He was hopping about trying to get them off and the alcohol wasn’t helping his coordination much either. He ended up stumbling and falling down in the grass but eventually got his shorts off.

“Dude? What are you doing?” I asked.

Jason responded that he wanted to go streaking. I wasn’t sure exactly where we were going to go out in the country, but I wasn’t much of one to back down from a dare either.

Determined to not make the same mistake that Jason had, I decided to just yank my shorts down, sit down on the grass, and pull them free. Jason reached down and pulled me up to my feet. He placed his hands on my shoulders and said, “Okay, let’s go!”

Physically Jason and I were very similar to each other, we were each 5’10” and 140 pounds. We both had straight, dark brown hair, though mine was quite a bit longer. Jason had a bit more muscle through his shoulders and arms, but not so much that most people would notice the difference. We actually were quite frequently mistaken for each other.

That would not be the case if we were both naked as Jason had the smallest cock in our class. Particularly in locker rooms, he stood out for all of the wrong reasons. There was barely a nub down there, particularly when it was soft. He was a bit of a “grower” at least. He was probably still short of five inches long when erect, but that was certainly more impressive than his flaccid state.

I was nervous as hell, but Jason was absolutely fearless as always. We headed down the driveway and started walking down the road. There weren’t many security lights along the road, but there was a decent amount of moonlight to help keep us from tripping over any random objects.

The night air felt a lot cooler now that we were unclothed. I was trembling from the combination of nerves and chills. As I looked down, my package clearly felt the same way. My balls were drawn tight and were forcing my shriveled cock to point straight out in a very unimpressive fashion. I thought to myself how embarrassing it would be to get caught out here like this.

As unimpressive as I looked, I only hoped that Jason was in a similar state. As I checked him out, I almost burst out laughing. It was so much worse for him. His balls were drawn as tight as mine, but his cock was in full retreat. In fact, I really couldn’t even see it as it was shrouded by his pubic hair.

There were only a few houses along the road, so we didn’t have a lot of worries about being seen by the neighbors. My biggest worry was where we would hide if a car came down the road. It would not take very long to find the answer to that question.

As we got about 1/2 mile down the road we saw a car turn down the road. At that point, it was quite a distance away, probably a bit over a mile. We joked for a bit about giving whoever it was a show. We were both waggling our cocks it the car’s general direction. But as the car closed in on us, I panicked and hid behind the only object that I could find, a telephone pole.

Even as skinny as I was, I am pretty sure that I wasn’t concealed very well. Maybe I was far enough off of the road that their headlights didn’t really reach over that far, though.

Jason was unwavering and just kept strutting his stuff down the edge of the road.

After the car passed, I ran to catch back up.

“Why did you run off?” Jason asked.

“Sorry, I freaked,” I said sheepishly.

Not long afterward, headlights appeared from behind us. Jason ordered me not to run away this time. We drifted a couple of feet off of the road to avoid being run over. As the car approached, I could hear it start to slow down. It hit the brakes fairly hard and the car stopped maybe twenty feet past where we were standing.

Jason ran up to the car. As he did, the passenger's window rolled down. I could see a lady in the passenger's seat, but there was a man’s voice coming from the driver’s seat.

“Are you boys lost?”

Jason responded, “Nope, we are just going this way.”

“Alright, don’t stay out too long.”

I could hear the couple chuckling as they rolled their windows up. I wasn’t sure exactly what they were laughing at, but they certainly had more than one thing to choose from.

By that point, my nerves had subsided. We walked around for well over an hour. Around a dozen cars had gone by. Another car stopped and we both talked to them. There was a car with several girls in it that honked and shouted “Woo!” as they crept by.

The excitement had worn off and we headed back to the house. We grabbed our clothes out of the yard and headed back inside. We each kicked our shoes off and put our underwear and shorts back on. We remained shirtless since the house felt quite warm after being outside undressed for so long.

We both grabbed a slice of cold pizza and a soda and gulped them down. I would randomly point at the toppings and ask Jason, “What is that?”

We settled into the living room. I had picked up a couple of movies for us to watch. Jason didn’t seem impressed with what I had selected.

“Do you have anything good?” he asked.

“Like porn?” I followed.

He nodded in response.

I didn’t really have anything hardcore. I had managed to pick up a couple of softcore videos through assorted channels. That seemed to be good enough for Jason. In those days the good stuff was hard to come by, particularly when you were just shy of eighteen.

I headed to my bedroom and retrieved the movie from my hiding spot. I started playing the movie and before we were through the previews/ads I turned to find Jason with his cock out already stroking away. To be fair, on those old videos the previews were actually better than the video itself. They weren’t very graphic either, but they were fast-paced and there was as much good stuff in a two-minute preview as there was in an entire sixty-minute video.

Jason’s cock hadn’t seemed to grow any since the last time that I had seen it. It still seemed to be clearly under five inches long.

I chuckled, “Do you like the video?”

He smiled at me, “I guess that I like it better than you do.”

That seemed like a bit of a challenge to me. I pulled my shorts down a bit and started to stroke away. I was being cautious to not push myself too far.

Once the actual movie started, the action slowed to a crawl, as I knew that it did. I always watched it with a lot of fast-forwarding.

Just as I was starting to get bored and my erection was beginning to fade, I heard Jason say in a high-pitched creepy voice, “Robbie, will you suck my dick?”

I assumed that he was just joking, so I ignored him.

“Robbie, will you please suck my dick?”

I turned to face Jason who was waving his cock at me between two of his fingers.

“Nah, that’s okay, I’ll pass on that this time,” I answered.

At that point, my brain was going into overdrive. I knew that Jason wasn’t really gay. Could it have been that Aaron had said something to him about our encounters? That seemed unlikely since Aaron wouldn’t have wanted anybody to know about what we had done, especially Jason. He must have just been joking. It was Jason, he was never serious about anything.

“Robbie, if you suck my dick, I’ll suck yours.”

I fired back, “Dude! Seriously, what is wrong with you? And stop talking in that creepy voice.”

I was starting to believe that this was a real offer, but I had to make sure. If only it was Aaron making this offer I would already have his cock halfway down my throat. I wasn’t even sure if I wanted to fool around with Jason. I didn’t really find him attractive, particularly from the waist down.

Jason snapped back into his normal voice, “Seriously though, I’ll suck yours if you suck mine.”

I started to think it over. Even though Jason was one of my closest friends, I knew him well enough that I did not trust him to return the favor. As I was pondering whether to go through with it or not, my thoughts were interrupted.

“I’ll go first if that changes your mind.”

I laughed at him, “You are such a horny fucker!”

After a brief pause where I pretended to think it over I added, “Yeah, that sounds like a deal.”

As we were two horny seventeen-year-old boys, we wasted no time. Jason stood up and finished undressing. By the time that I had sat up, pulled my shorts and underwear down, and kicked them off, Jason was standing in front of me.

I suddenly felt very nervous. This was only the second person to ever suck my cock, and it was the first male to do so.

Jason didn’t say a word, he just dropped to his knees and grabbed onto my semi-hard cock. He seemed a bit nervous although he wasn’t one to really show that sort of thing. I was relatively confident that it was the first cock other than his own that he had ever handled. I wondered if he was as amazed by how it felt in his hand as I was the first time that I held Aaron’s. Comparatively, I would have been an even bigger upgrade for him. I was a full two inches longer and quite a bit thicker.

He held onto my cock for short while and before I realized that he was moving in I felt his hot, wet mouth on my cock. I leaned my head back and tried to just enjoy the moment.

That would have been terrific if I could have done that, but he was pretty terrible at sucking dick. I let him fumble away for over five minutes before I pulled his head away.

“Okay, let’s switch for a while,” I said.

Jason was absolutely down with the change of plans. He hopped to his feet and took a seat on the couch. I dropped to my knees and as I leaned in Jason grabbed his cock and guided it to my mouth. I opened my mouth and after just a few bobs of my head, Jason grabbed me and started to thrust away.

It was one of the things that I feared about fooling around with Jason. He was an aggressive, selfish guy and he was always going to do whatever he wanted to do.

After a short barrage, he stopped for a bit. I wasn’t terribly good at oral either, but I was always able to get by with Aaron by stroking the base as I sucked away. I didn’t see how that was going to work with Jason. If I wrapped my hand around his cock, there was nothing left to suck on.

I tried placing my hand flat against his stomach and wrapping just my thumb and forefinger around his cock, but that didn’t seem very effective either. Jason fired up again and started face-fucking me for a bit. Fortunately, he couldn’t really go deep enough to gag me. He mostly just created a lot of contact with my teeth as he rammed about.

Once he stopped, I really wondered if we should continue on. I was about to suggest that we just jack each other off, when Jason said, “This isn’t working. We should fuck instead.”

I couldn’t believe that he had made that offer. Actually, it kind of seemed like the perfect solution for me. Jason’s little cock seemed like it would be perfect for my first time. He was certainly getting the more uncomfortable end of that deal. He did have a cute, little ass. I could easily imagine fucking it.

I was somewhat worried that neither of us had done any planning for this ahead of time. There was the distinct possibility that this could get a little bit messy.

“Same deal as before,” I said. “You have to go first.”

Jason agreed to the deal and I headed upstairs to get some supplies. I returned with a couple of condoms and a small bottle of Astroglide. I went into the bathroom, grabbed two towels, and wet two washcloths.

I unfolded one towel and told Jason to get down on all fours. He complied. I gave his ass a bit of a wipe down and a bit of lube directly from the tube. He let out a gasp as the cold lube hit his hot, little hole. He actually looked pretty fuckable from that angle and I was hopeful that it would work out better than the previous encounter.

“J, I changed my mind about this,” I said.

“What? Are you kidding me?” he fired back, clearly not happy.

I added, “I want you to go first. That way if you get too crazy back there I can return the favor.”

“Yeah,” he contemplated. “I guess that might slow me down a bit, huh?”

I dropped to my knees and he repeated the preparation on me, complete with a squirt of cold lube. I turned around to find him fumbling with the condom. It was significantly baggy and I immediately wondered if he could keep it on. I asked him to put some lube on the condom also and he obliged.

I heard him shuffling about behind me and felt his knees slide in between my legs, spreading them apart a bit further.

I felt the coldness of the wet condom press against my hole. Jason asked if I was ready. I confirmed that I was and I asked him to stop as soon as he was inside.

With one firm thrust, his cock popped inside of me. I wasn’t sure how deep he was, but I couldn’t imagine having to take any more than that. I had never inserted any more than a single finger inside of my ass before and although Jason had a pretty small cock, it was certainly a bit thicker than a finger.

I took a minute to catch my breath and let my body adjust to this new situation.

I gave Jason permission to start as long as he took it easy. After just a few full strokes, I could feel his body press up against my ass. I knew that he was all of the ways inside of me at that point. Even though it felt like there was no way that I could take anything any larger it didn’t hurt in any significant way.  I felt comfortable that I could handle most anything that he threw at me at that point.

As he finished each stroke I let out a “Ungh!” almost every time. He picked up on it very quickly.

“Does that big cock hurt?” he chided me.

As a bit of a backstory, there was nobody at our school that bragged about how big their cock was any more than Jason. The irony was that he had absolutely nothing to brag about. It was clearly a smokescreen to make girls believe that he was packing. It didn’t really work on us guys, though. Many times we would roll our eyes at each other while he was going on about it.

It wasn’t until that moment as I was on my hands and knees with J’s cock in my ass that I really realized how self-conscious he was about it. I wondered how he would react if he actually got the response that he wanted.

“Fuck, dude! That thing is big!” I groaned as a couple of grunts interrupted my line.

He went quiet for a bit.

“Your ass isn’t going to be the same after I am done with you, Rob!”

Jason started to get more aggressive. There was the slapping sound of flesh on flesh with every stroke. I could feel my limp cock jostle with the impact.

“Oh, Fuck! It hurts so much!” I pleaded at Jason in an effort to try to sound completely overwhelmed. I kicked my feet slightly, bit onto the towel so it muffled my groans, and clawed away at the carpet.

Almost immediately, Jason wrapped his arms around my waist pulling himself in as deeply as he possibly could.

“I am going to fill your ass with cum!” he barked.

“God! Please hurry up! I don’t think that I can take much more!”

At that point, he was barely moving. Suddenly I felt his cock twitching inside of me. It actually felt pretty amazing.

“Oh, Fuck!” Jason shouted, followed by a loud roar.

He remained stationary for a while, before finally backing away. I thought that he had pulled out, but it still felt like he was inside of me. I turned back to confirm that he had withdrawn. My body definitely felt different.

“Fuck, Rob. That was…that was…alright..”

As I turned around I could see that the entire condom had unrolled as he was fucking me. I was probably lucky that I didn’t have to fish it out of my ass.

We each cleaned up and got ready for round two. I feared that Jason was going to back out of the deal now that he had got what he really wanted out of it.

Much to my surprise, he did not. He returned to his spot on the towel and offered his ass to me once again. I gave him a second squirt of cold lube and laughed at him.

“Got you twice!” I joked.

I quickly put on a condom and lubed it up. As I lined myself up for entry I told Jason, “Let me know when you are ready, and don’t forget to breathe.”

I could see that he was a bit nervous, but he tried to play it off. He was perched on his forearms with both fists clenched.

Jason gave me permission to start. I gave a firm push and felt his ass slowly open up. I could hear the air escape from J’s lungs as I pressed my cock about halfway in and stopped.

He let out a whiny groan. I could feel him try to push me out.

“Don’t push! Don’t push!” I shouted. “Just take some deep breaths and try to relax.”

After a little bit, he gave me the okay to continue. I started to just rock back and forth the slightest amount.

“When you go out it feels like...”

“Yeah, I know,” I responded.

“How do I know that I...”

I chuckled, “Trust me when I say that I will be the first to let you know.”

I started to lengthen my strokes a bit. Jason was clearly in a lot of discomfort. Fortunately for him, the fact that he was in discomfort meant that his ass was clamped onto my cock very tightly. I couldn’t believe how snugly he was gripping me.

The more that I moved, the more quickly we were getting to the end.

“Are you doing okay?” I asked.

“Yeah. Yeah. Just hurry up!” Jason exclaimed.

Very shortly thereafter I groaned, “Oh, god! I’m fucking cumming!”

I tried to power through as best as I could. As I came, I could hear Jason let out a little whimper as my cock throbbed inside of him. My head reared back and my mouth drew wide open. I held that position for a while until I felt saliva pour out of my mouth and onto Jason’s back. I was pretty embarrassed by that, but I didn’t think that he even felt it.

I slowly withdrew my cock and patted Jason on the butt. He turned around and faced me in a seated position. His face was quite red and I could see that he had been wiping some tears from his eyes. He stared at my cock for a bit. There was a pretty significant amount of cum in the condom.

I gestured at it, “Dude, your ass is so fucking tight.”

Jason asked sheepishly, “Does your ass feel like my cock is still inside of it?”

I chuckled, “Yeah, that’s why I looked back at you several times.”

“I couldn’t wait for you to pull it out of there and now that you have…”

“You feel kind of empty and wish that it was back in there?” I chimed in.

“Yeah, yeah that’s about right,” he added.

We both agreed that we needed a shower. I wasn’t really sure what our relationship was going to be after that experience. I got some towels and turned the water on and told Jason to go first.

He headed into the shower and I wasn’t sure if I was supposed to join him or not. I didn’t feel like this was really a romantic kind of relationship, but it felt kind of strange for both of us to lose our anal virginity and act like it didn’t matter.

Jason took a long shower. After he was done, I hopped in. Once I had finished, I headed into the living room to find Jason sitting in the chair with his towel wrapped around him.

“Are you alright, J?” I asked.

“Yeah, I am just really tired. That was completely draining.”

I gestured toward my bedroom and said, “Let’s go to sleep then.”

Jason nodded in agreement. We both headed to my bedroom, tossed our towels on the floor, and slid into bed.

The next thing that I remember is waking up in the morning. I turned around to see Jason staring at the ceiling.

“Are you alright, J?” I asked.

“Dude, I am so fucking horny right now!” he exclaimed.

“Yeah, me too,” I replied as I peeled back the covers exposing my raging hard-on.

“Same deal as yesterday?” he asked.

“Yeah, sounds good to me,” I replied.

I gathered the towels from the floor and retrieved a couple of additional condoms. Jason ran to the living room and grabbed the bottle of lube that we had left there.

When Jason returned to the room, I had already placed a towel over the bedspread. I told him that I was going first this time and positioned him on his stomach over the towel. This time I was nice and warmed the lube up before applying it.

As I inserted my cock into Jason, I could tell that he was still very sore from the previous night. But I couldn’t really let him have a pass on it, we had an arrangement. I did manage to finish in record time, though.

We quickly changed positions. In fact, so quickly that I still had a soggy condom dangling from my dong as I positioned myself for entry.

I was quickly lubricated and penetrated. Jason seemed eager to make me as sore as he was. Unfortunately for him, I had already figured out how to finish him off quickly.

A brief acting performance later, he was quickly dispatched.

We cleaned up, got another quick shower and Jason headed back home.

Before he left we made a pact to both keep each other’s secret and to renew the arrangement any time that we both felt the need.

It was a flurry of quickies over the next couple of weeks. I think that we only missed one day in two weeks. After that, it eased up a bit. We still managed two or three times a week for the next several months. There were never any displays of affection of any kind.

After that, we both headed off to college in different directions. Jason settled down with what most would consider a rather inappropriate but proper girl. They are still married and have several children together.