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One Last Vacation

Category: Gay Male
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We had known each other all our lives, and had experienced enough adventures together to fill a book. Twelve years of school, Little League and building forts, and now that we were out of high school, we were heading our separate ways as we were bound for different colleges.

Before Ken left for school, we made a point to spend a last few days together at a nearby resort town.

Renting a cheap motel room, we went out the first night and drank a whole lot of beer while listening to local bands play. The fact that it was hot and muggy made it seem like the beer was coming directly out of our pores, but I still felt a little buzzed by the time we called it a night.

When we got back to the motel room, the heat situation wasn’t helped by the fact that the window air conditioner was a piece a junk. A noisy piece of junk at that, as it made a lot of noise but only blew a faint cool breeze.

The room was the cheapest that we could find, and only had one king size bed in it. We decided to redecorate the dump by moving the bed over next to the air conditioner, so that we would get whatever benefit there was from it.

It was halfway decent outside, so we decided that we would sit out on the plastic lawn chairs in front of our room until either we got too tired to stay awake or the bugs ate us alive.

We spent a lot of the time reflecting on our lives – and our lives together – which seemed to be hopelessly intertwined. Just about anything we had ever done that was funny or memorable, we had done together.

Even the one great love affair that I had enjoyed was connected with Ken. I had dated his sister Denise for almost a year until we broke up last spring, and it still hurt from my end. I thought that she was the one, until she told me that I wasn’t, at least I wasn’t the one for her any longer.

“You two were so good together,” Ken remarked as I opened a beer, and laughed as we watched it erupt all over me, a sure sign that the beer was getting as warm as the air that surrounded us.

“Tell me about it,” I lamented, thinking back about the girl who had stolen my heart and taken my virginity. “It wasn’t my choice, remember?”

“She’s sorry now that she broke it off.”

“Is that right?” I asked. “How would you know?”

“I have psychic powers,” Ken informed me. “That, and I have a key to her diary.”

“And I’m in it?”

“You’re all over it,” Kenny laughed. “I know just about everything you two did.”

“Oh man,” I said glumly. “This is embarrassing.”

Although I always figured that Kenny had assumed that I was having sex with his sister, I had never said a word to him about it, and actually hearing it from him was a little disturbing.

“It shouldn’t be,” Kenny assured me. “You got rave reviews.”

“I’ll bet.”

“I can’t believe how many times Jamie can get it up,” Kenny said in a falsetto tone. “His cock is always so hard, and I love the way he does me from behind.”

“Please,” I begged, wanting to crawl under the chair. “What did you do, memorize it?”

“Just about,” Kenny admitted. “Jacked myself off more than once reading about you two – wishing I was joining in.”

I laughed, but nervously this time, and I guess the look on my face gave Kenny some concern.

“Think that’s freaky?” Kenny asked, shrugging his shoulders.

“Well, Denise is your sister,” I reminded him.

“Yeah, and I got to watch her grow up all these years, and all those times that I got some innocent peeks at her undressing and stuff,” Kenny offered. “I’ve seen enough of her to know that I’m really familiar with what you were nailing.”

“I guess so,” I agreed. “If I had a sister I would probably be as horny as you.”

“Did you like that girl I was trying to hit on tonight?” Kenny recalled.

“The one with the big boobs?”

“Yeah! Now she was cute. Wouldn’t that have been cool if we brought her back here and we both did her?”

“A threesome?” I said, thinking of the possibilities.

After we drank the last beers, we decided to call it a night. A shower was definitely in order, and so we flipped a coin to see who would go first.

“I’ll save you some hot water,” Ken promised as he celebrated his victory, leaving me outside to swat bugs until he got done.

While I waited, I walked around to the back of the building, counting the number of windows I passed carefully until I got to our bathroom window, which was open a bit. I was going to try and scare Kenny, but decided against screaming at the last minute.

He had his back to the window, and was drying off with the skimpy little towels, his slender and pale back glistening with moisture. Kenny looked a lot like his sister facially, and didn’t look that much different from behind either. With his long brown hair and his build, it could have been easily mistaken for a girl from that angle.

“Save me some towels there, sailor,” I whispered loudly, and Kenny almost had a heart attack when he heard my voice.

“Son of a bitch!” Kenny exclaimed, covering himself up with the towel as best he could.

“Always so modest,” I said with a laugh before leaving the window. “How are we going to have a threesome if you’re so shy?”

I went back around to the front of the building and into the room, getting undressed just as Kenny emerged from the steaming room. My nakedness always made Kenny uncomfortable, and I liked as he pretended not to look at me as I walked past him. It didn’t bother me if he looked or not. It’s not like I had a fantastic body, but I was in good shape.

The shower spray was weak but refreshing, and I stayed in there for a long time. As I came out of the bathroom, I saw that Kenny was on the bed and already asleep, judging by the looks of him. Perhaps it was a result of having had a few beers too many, but after I glanced over in his direction, I did what must have been the most comical double-take in history.

Kenny was on his back, arms and legs akimbo, and the sheet that had been over the lower part of his body was now down around his ankles. For all intents and purposes, my very best friend was naked and completely exposed.

That was strange in and of itself, because Ken was a very shy person. It didn’t seem like he had any real reason to be, but that’s the way he was. We had taken showers in gym together, and had taken leaks behind trees and that sort of thing, but he wasn’t the type to waltz around naked in front of me. The times I had seen his dick, it didn’t look all that different than my own.

Now Ken was passed out and naked on the bed – the bed that we would be sharing. The problem was – who was this guy on the bed? I stubbed my toe on the dresser and cried out, quickly looking to see if he had woken up, but except for a slight fluttering of the eyelids, he remained motionless.

My eyes went right back to the area between his legs, and more specifically on his cock, which hung lazily onto his hip bone. Long and slender, it looked like an beige snake, and when I passed the foot of the bed, that angle made it look even more shocking, as the veins and stretched skin made the base of it look like the roots and trunk of a tree. It wasn’t as thick as mine, but as for the length, there was no comparison.

Keeping my towel tied around my waist, I went over and locked the door and turned off the light before getting into the bed, trying my best not to disturb Kenny. That was easier said than done, since he was splayed over much of the bed, but I managed to find a space on my side after a little maneuvering.

One thing we hadn’t considered when moving the bed to the window was that now the lights from the street lit up the inside pretty brightly. The noisy air conditioner masked most of the traffic sounds, although I could hear the scraping of shoes going past the window. Since the light poured through the curtain so easily, I wondered whether people could see inside as well.

That was all the more reason for me to keep my towel around me, not that anybody would give me a second glance with Ken and his anaconda-like penis resting beside me. For a second I considered pulling up the sheet to cover him, but decided not to because it was so hot in the room.

I could feel the heat radiating off of Kenny’s body as he lay scant inches away from me. Rolling over on my side, I was happy that he had just showered, as his armpit was right next to my face. As I breathed through my nose, I could see his armpit hair flutter when I exhaled, which was further proof of how close we were.

Funny that Kenny had so much hair under his arms, since the rest of him wasn’t hairy at all. That was a source of constant embarrassment to him over the years; his chest being smooth and his legs sporting only a light dusting on the inside of his calves, and he always made references to me having a rather hirsute body and wished that he was more like me.

Seeing Ken naked now made that desire of his seem foolish to me, as my eyes went back down his body. His cock was not quite as long as it had been earlier, but the size of it was still intimidating to me. Having played sports all my life, I had seen more than my share of other guys dicks, and seeing a guy with a tool that was longer soft that mine was hard, was sure as hell not something I was used to.

Maybe he had been dreaming earlier, I wondered. Perhaps he was thinking about his sister joining the two of us in bed and was getting excited. As sick as it sounded, I thought the image of the two of them together was erotic as hell, and then tried to picture what the three of us would look like, As I pictured that scene, I mused about whether Denise had ever seen her brother’s cock.

All of this fantasizing was having an effect on me, and while I tried to blame it on the beer, I was trying to find a way to touch Kenny, and to touch his dick. Just curious, I said to myself in order to justify it. Never having touched another guys stuff, I was merely wondering if it felt the same as my own, and being very experienced in handling my own equipment I thought it to be a valid reason.

I moved my leg toward Kenny, feeling the hair on my leg make contact with Kenny’s calf. In response Kenny seemed to come closer to me on the bed, with our legs now in full contact. His cock was now almost touching me, and all I had to do was grab it.


I didn’t grab it, as tempted as I was. What I was feeling was easily signalled by the tent that was my towel, as my cock was rock hard and poking straight up into the air with the threadbare white cotton over it.

There was no way that I would risk a life-long friendship by doing something of that nature. What would he think of me in the future? He has too much to drink one night and I start groping him? He would never trust me again.

With that in mind, I made a noise that I tried to pass off as one of a half-asleep drunk, and gently rolled a little away from him and onto my hip. I was almost off the bed, but had created a little space between us, and after doing that I tried to relax enough to be able to fall asleep.


One thing about staying in motel rooms is that I can never figure out what time it is. Because of the strange surroundings, I’m disoriented as it is, and the lack of a clock in the room was no help, so I have no idea how long I had been asleep when I woke up, and maybe I had never actually been asleep at all.

When I did wake up, I quickly discovered to reason. Kenny’s hand. It was on my hip, and Kenny’s body was right up against mine. I tried to keep breathing normally as I lay there, afraid to move.

Probably just rolled over in his sleep, I tried to convince myself, and so I tried to keep my heartbeat from sounding as loud as it felt. In a minute, his hand would probably just slide off. Hell, I could end this all right now by simply sliding off of the bed and going to the bathroom for a few minutes, or simply grab his hand and push it away.

I did neither of those things. Instead, I just lay there and waited – waiting for who knows what. I didn’t have long to wait.

With a slow, circular motion, I felt Kenny’s hand rub my stomach with a pressure so light it was almost like the breeze coming from the air conditioner. His fingers caressed the thick growth of hair that covered the area, and after a minute or two of that, I felt his hand slide downward.

Now he was at my navel, and my breath was now very rapid and ragged, with my chest heaving rather noticeably. My cock was now straining under the cotton as Kenny’s hand slid down to the edge of the towel.

I continued the charade of being asleep, not sure of what else to do. His hand had stopped moving downward, but only so he could pull me gently towards him so that I was flat on my back. As I allowed him to move me, his hand went back down onto me, inching along the edge of the towel until he found the loosely done knot that held it together.

With a mere flick of his wrist, Kenny worked the knot open, and grabbing the edge of the towel, slid it off of me. My cock was now exposed, the short, fat fireplug of an organ standing straight up, never any harder than it was at that moment.

I was momentarily humiliated as it occurred to me how small it was compared to my friend’s, and I wondered what he must have been thinking when my stub came into view. It was pretty thick, but not quite the six inches I had always convinced myself that it was. Now standing erect in the dim light, my mini-monolith looked even shorter than ever.

Whatever fears I had over my shortcomings promptly disappeared when Kenny’s hand let go of the towel and resumed its position just above my pubic hair.

Deliberately, his fingers entered the bush, much like a hair brush as they combed their way through the forest. I let out an barely audible and totally involuntary moan as his fingers slid close to the base of my cock, only to rake back to where they had begun. Kenny did this for the longest time, and if the intent was to pique my interest or get me excited, it was working on both accounts. It was all I could do to keep from grabbing Kenny by the wrist and putting it on my boner.

Now Kenny’s hand moved in a different direction, sliding around my cock without touching it, with his thumb sliding above my erection and his fingers moving underneath, into the area between my cock and balls. I let out a noise that could have been a whimper or a pleading at this new touching, and I could feel Kenny’s breath on my ear now.

“Jamie?” he asked in a whisper.

I remained silent, maintaining an attitude that suggested I was still sound asleep. This despite the fact that my chest was heaving up and down and I was wheezing like I had just run a marathon.

“Jamie?” Kenny repeated. “Do you want me to stop?”


I didn’t want him to stop. I also didn’t want to admit that I knew what he was doing. The thought of saying that – yes, I know that you’ve been disrobing me and teasing me and I’m curious and want you to grab my cock – was unthinkable to me at that moment.

My way of answering was to start to undulate my lower torso into the light touch of Kenny’s hand. His fingernails were moving up and down -softly scraping the top of my sac and then up to the base of my dick, which twitched and jerked uncontrollably.

Then, suddenly, Kenny withdrew his hand. I felt the bed jostle a little bit, and then heard a clicking sound. That was followed by the bed moving again, as I felt Ken’s body move a little.

He was next to me again in as second, as as Kenny’s hand came back down between my legs, I felt a cool gel hit the underside of my cock an instant before he grabbed my member. Quite lubricated, his slick hand took hold of the base of my cock and began to pump it.

His hand slid up and down the length of my cock, making me gasp as his grip spun in a circular motion while going up and down. The groan I let out then was much louder, and Kenny climbed up on his knees, straddling my left thigh while continuing to jerk me off. I could feel his balls on my thigh as he rearranged his hold on me.

While Kenny forcefully milked my cock, I saw his own manhood bobbing out in front of him. Reaching up, I tried to grab the swaying pole but he knocked my hand away, leaving me to writhe helplessly on the bed while his hand spun and pumped me.

On the verge of cumming for what seemed like forever, I tried to thrust myself upward in response to Kenny’s hand, but he maintained the same painfully deliberate pace, only pausing to switch hands and to begin working on my balls.

Kenny grabbed my nut sack roughly and began churning the pouch in his hand as my orgasm remained so close yet just out of reach. It was almost as if he knew exactly how close I was to cumming, and when I reached that point he would slow down or lighten his grip.

“Ohhh,” I groaned, wanting to cum so badly, and needing t as well, judging by the look of my greased cock as Kenny’s hand slid up and down the incredibly taut and now-purplish tool.

I then realized that Kenny had begun to grind onto my thigh in what seemed to be almost a humping motion. The underside of his cock slid hard onto my leg, his sac sliding along with it. How badly I wanted to grab him – to do to him what he was doing to me – and doing so well that I was going half out of my mind.

“This good, Jamie?” I heard Kenny whisper.

“Yes,” I grunted in response. “Cum. Want to cum.”

“Soon,” was his response, and with that he continued the rough and deliberate manipulation of my cock and balls.

How long this went on, I could not say. I was so aroused and so crazed that by this point I had lost all sense of time. My cock was drooling seed like lava from a volcano now, and Kenny was beginning to move harder and quicker on my thigh. As he did, his grip on me changed, and I felt my whole body begin to tingle. Kenny was still yanking on me just as slowly, but now was pulling on my cock hard.

I let out a cry as I felt my orgasm rush through me, and while looking down, I watched my cock erupt as volleys of my seed flew a couple of feet in the air. My vision blurred as a wad of cum splattered all over my face, and I could feel more raining down all over my upper torso as my body quivered uncontrollably. It was only when my cock went limp in Kenny’s hand that he stopped milking me and let go of my spent dick, sliding down on the bed beside me.

We were both on our backs in the bed, staring up at the ceiling, and the only sound in the room was the air conditioner. I became aware that I was drenched in semen, and then noticed that my thigh and hip also had a copious amount of quickly-cooling seed all over it. A glance down between Kenny’s legs revealed that his cock was also flaccid, and I was wearing the reason for that.

Kenny moved first, reaching down and grabbing the towel that used to cover me, and wiped off the load that he had deposited on me before trying to clean the mess that was my chest, finally giving up as the cum-saturated cloth was of no more use.

“Are you mad at me?” he asked after laying back down on the bed next to me.

“No,” I whispered back at him, as I rolled onto my side to face him.

“Was that good for you?” Kenny asked, staring up at the ceiling so as not to have to look at me, I supposed. “I know it was nothing like having Denise’s mouth working on you.”

“No, but I’m embarrassed at how good it felt,” I admitted. “Better than my own hand, that’s for sure. What brought that on?”

“Always wanted to do that to you,” Kenny said. “I figured that this would probably be the last chance I would get to do it.”

“We’re just going to different colleges, man. It’s not like we’re saying goodbye forever,” I assured him.

“It will never be the same between us, though,” Kenny said, with a hint of sadness in his voice. “We’ll start to grow apart as time goes on. I mean, I know it’s got to happen, but it’s still a tough thing to face. Not having you nearby to count on.”

He was right of course. Things were different.

My hand moved over to his dick, which was back in the modest state I had seen so often over the years, and Ken offered no resistance when I wrapped my hands around his limp stem. His cock was no bigger soft than mine was, and when I began pulling on it I could immediately feel this difference.

Ken’s cock was very rubbery, almost elastic to the touch, and after a minute I could feel his member begin to respond to my handling. The increasing size of it was making it more of a challenge to properly stroke, but a minute later I was running my hand up and down the length of his amazingly long erection.

“Can’t believe it, man,” I whispered in the semi-darkness. “Your cock is so big hard. Has Denise ever… you know seen it? Hard, I mean.”

“Yes,” Ken said, and as I felt a coldness on the back of my hand I realized that he had squirted some lotion on himself, and my hand now slid smoothly on his cock. “Caught me jerking off once.”

“Really?” I asked. “What did she do?”

The silence in the room was deafening, as only the squishing sound of my hand and our breathing were audible. I found myself getting onto my knees at Ken’s side, and when I started using both hands to jerk off my friend, he began to move his hips up and down against my grip.

“Well?” I asked.

Kenny grunted seconds before he came, and his cum flew wildly out of him and all over us as I pumped his floppy over-sized organ long after he was completely drained.

I wiped my cum-drenched hands on the sheet and joined Ken back on the bed, quietly staring at the ceiling while I tried to figure out everything I had said, done and heard.

thanks for reading

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