Sex in the Sky

“I hope readers will find this story interesting. This is my first attempt and I thought writing about something that actually happened would be a good way to start. I would appreciate any and all comments.”

***

1. Standing alone in the rain.

That’s what I was doing on that miserable late summer morning somewhere in the neighborhood of Lee, Massachusetts; standing in the rain near the entrance ramp of the interstate, doing a bad job of hitchhiking. How I managed to get to this spot is a long story which is painful for me to recall even now.

The condensed version is that I was going to go out to my brother’s house in Wisconsin, where I would be attending college starting in the second semester. My parents wanted me to fly out there, but I insisted on taking the bus, telling them that I loved the idea of seeing the world through the windows of a bus.

In truth the prospect of getting on a plane scared the crap out of me at that point in time, but I was too ashamed to admit it. They relented and I took the bus. I got to the first stop where I had to change buses, where I made the ridiculous decision that my backpack would be fine where it was while I ran in to the bus station men’s room.

When I came back out, my backpack was gone. Along with the backpack went my bus tickets for the rest of my trip, because I thought it would be a good place to keep them in there and make sure they didn’t get lost. When you’re 18, you do a lot of stupid things, and this ranks up there with the best of them.

The police looked around with me for a time before concluding that I would not likely be seeing that backpack again. Refusing the offer to use the phone to call home, I decided that the best move would be to hitchhike. No way would I call home and have to explain what an idiot I was, because I’d never hear the end of that.

So with $17 or so in my pocket, I set out on my journey. Twenty four hours later I had gotten about fifty miles. I spent a less-than-comfortable night sleeping under a highway overpass and woke up with the sunrise, determined to continue on with my trek.

I guess it was almost noon when it started raining, and when it rained, it poured. I was cold and soaked to the bone. Drivers couldn’t even see me in the torrential rain, and even if they could, who wanted to let someone in their car that looked like I did? My long hair was no help either, and I was beginning to think that I would have to spend what little money I had to get back home, where I would have to listen to how stupid I was for the rest of my life.

Suddenly, a car that had flown by me pulled over and began backing up along the shoulder. I ran to meet my savior, jumping into the car when we met.

“Thank you so much!” I said excitedly.

“No problem,” my benefactor said. “This is no weather to be out in.”

I told the driver my sad story from the beginning, and being able to unload was very cathartic to me, since if I actually got to my brother’s I would not be telling anyone else this stuff for quite a while.

The man that picked me up was an elderly gentleman with thick grey hair and long, bony fingers, which was all I could see of him. I would have guessed him to be in his sixties, although ages are tough to guess when you think 30 is ancient. He looked like a businessman of some sort, and was dressed neatly yet casual.

“Well young man, I can’t get you all the way to your destination, but I can take you a good part of the way.”

“That’s great!” I exclaimed happily, enjoying the fact that I was at least no longer in the rain. “I can give you some money for gas, mister.”

“No, that’s all right young fellow. Save your money. My name’s Gordon. Walt Gordon.”

“Oh, I’m Tim… Tim Wells, Mr. Gordon.”

“Call me Walt,” Mr. Gordon said. “Mr. makes me feel even older than I am.”

Walt drove across New York and into Ohio that day, before finally stopping just outside of Cleveland. He pulled into a motel parking lot and drove up to the office.

“Thanks a lot for the ride,” I said while I reached for the door handle.

“I was going to spend the night here before going any further,” Walt said. “Can’t seem to drive as long as I used to these days. If you want, you can stay here for the night before going on. We could get a bite to eat or something, if you’d like that is.”

I thought about my financial situation, and did some mental calculations.

“If you’re worried about money or anything, don’t,” Walt said. “Save your money. The room costs the same whether there’s one or two people in it. It’s my treat.”

“Thank you,” I finally said. “Look, I want you to give me your address so I can pay you back for all this.”

“No need,” Walt said as he got out of the car. “Maybe someday you’ll be in a position to do a good turn for someone else.”

2. Room 17.

Walt came back out of the office and drove the car around the side of the motel and parked in front of Room 17. Walt had a small suitcase that he brought inside with us. I, no longer burdened by such things, waddled in empty handed.

It was a pretty drab room, much like any chain motel would look like. The one thing that caught my eye was that there was only one bed, but since I had spent the previous night on concrete with pigeons, the floor still looked good to me.

“Say Timmy, you probably don’t want to go out to eat looking like you do,” Walt said. “Why don’t I go out and get us a pizza or something?”

“Sounds great to me!” I eagerly added, not having eaten all day. Given my pudgy body, that wasn’t the worst thing in the world anyway. Walt had taken to calling me Timmy, which made me feel goofy, but I was in no position to complain.

“There’s a laundry room next to the motel office,” Walt said. “Why don’t you get your clothes off and give them to me. I’ll go put them in the washer before I leave, and then dry them when I get back. That way you’ll be able to take a shower and wash the road off you as well.”

The thought that I must be pretty rank by now hadn’t occured to me until then, but as I inhaled the musty funk that I was radiating, I took Walt’s advice. I went into the bathroom and took off my still-damp wardrobe; handed the pungent garb through the door to Walt, and hopped into the shower.

As showers go, this was one of the all-time greatest, and I rejoyced at the sudden good fortune I was enjoying. Walt was a really good guy, and I was so glad that I had run into him.

I stayed in the shower for a long time, and only reluctantly got out when I heard Walt return. I grabbed the towel, and grimaced when I saw it was the standard dish towel sized cotton variety. Not nearly enough to cover a human being, so I grabbed another one and tried to get everything hidden. I looked at the mirror at my 5′10″ frame, with the 200 or so pounds it was carrying and shook my head. Had to start losing weight soon, I thought to myself.

Walt had come back with the pizza, and had also brough back a six-pack of beer.

“I know young fellows like beer,” Walt chuckled. “Hope I was right.”

“Sure, I love beer,” I agreed happily.

We ate the pizza and drank the beer while watching baseball on TV, and although I felt goofy sitting there in towels, it didn’t seem to matter to Walt. Walt left after a few minutes to put my washed clothes into the dryer, and when he returned he was shaking his head.

“Laundry room’s closed,” Walt muttered. “Guy in the office says it closes at nine, but there’s no sign telling you that. He says it opens up at 7. I’m sorry about that Timmy. I’d let you wear something of mine but I don’t think you’d fit into anything I have, because you’re a big strapping lad.”

Big I guess compared to Walt, who was a couple of inches shorter and almost 100 pounds lighter than me.

“Uhh… that’s okay. I can get through the night like this I guess.”

We finished the pizza and as we were downing the last of the beers I started trying to figure out where on the floor I was going to sleep. I figured I could wrap myself up in one of the comforters. When I mentioned this to Walt, he semed shocked.

“Timmy, I’m sorry,” Walt said while slapping his head. “I travel alone so much I hadn’t thought about that. That’s a big bed, and there’s plenty of room for both of us.”

“No really, I can sleep on the floor,” I said.

“Nonsense! If either one of us sleeps on the floor it will be me. After all I was the one who screwed up.”

Well, there was no way that I was going to have this poor old guy sleeping on the floor after he paid for everything. Besides, it was a big bed, like Walt had said. With that in mind I went over to the bed, clutching my two little towels around me and crawled in to the far end of it. I tried to make the towels into a pair of underwear as I settled in.

“I’ll be turning in soon too,” Walt said as he headed in to the bathroom.

The sound of the shower had me dropping off in no time, but I awakened when Walt came out of the bathroom, a cloud of steam following him almost like a special effect. Walt walked over to the TV and turned it off while turning on the small lamp on the dresser. Walt was having the same problem with the tiny towels as I had, but there was a lot less of him to cover.

I felt kind of creepy pretending to be sleeping while squinting to watch, but I was nervous being around a stranger like this, even though Walt had been nothing short of great to me all day.

Walt was in pretty good shape for a old guy. He had a really slim build which I would have died for, and when I saw his little white butt I almost giggled. Walt was drying himself with the towel when he turned around to grab something off the dresser. I couldn’t help looking as he swung around and faced my direction.

Walt’s cock hung down between his skinny thighs like a hose. I couldn’t believe the size of his thing, and it was limp besides! I was thoroughly convinced that I had the smallest dick in the world anyway, and now seeing this equipment on this guy who was no bigger than a jockey only reinforced my thinking.

Walt walked around the room for a few minutes, and I kept watching his cock lazily sway in front of him like an elephant’s trunk. It didn’t seem really thick but it was damn long. Walt got closer to the bed, and when he did, I got a better look at his cock, and I was shocked. At first I thought he had some sort of accident, because there was something wrong with the end of it. It took me a second to realize that this was what uncircumsized meant. I had heard the term and knew what it involved, but had never seen one in person, and I thought it looked kind of neat. Almost made it ominous looking in a way.

At this point I thought I had better close my eyes and get to sleep. If Walt ever caught me looking at his cock he’d think I was some sort of weirdo and throw me out of the room, so I let myself drift off to sleep.

3. In the night.

I was dreaming. Weird dreams about all the times I had been naked around other guys, and how I would have to hide myself so they didn’t see how small my dick was. What a revelation it was in the showers after gym when I saw other guys for the first time and realized how woefully inadequate I was.

After that I made a career about avoiding any situations where other people would see me naked. I had been with a couple of girls, and one of them had given me a hand job. She didn’t say anything or laugh when she jerked me off, but I figured she was just being nice. No girl with any experience would be interested in a guy whose dick was about 5 inches long at best, so my only hope was to find a girl who hadn’t seen too many of them.

It was around that point when I found myself waking up. I was laying on my side facing the wall, when I felt warm breath on my neck. Walt’s hand had swung over onto my hip, probably the result of tossing in his sleep. I squirmed a little to get it to slide off, but that didn’t work.

Instead, I felt Walt’s fingers grab the corner of the towel and pull it off me. Now Walt’s breath was closer, and he was curled right up next to me. I could feel his coarse chest hair against my back as his hand slid down my bare hip and slowly worked downward until it came upon the sparse tuft of hair above my dick. Walt’s hand stopped there and he just ran his fingertips through the bush.

I was freaking out at this point, uncertain what I should do. I was still pretending to be asleep while Walt toyed with my pubes, when he pulled himself right up next to me. I felt Walt’s cock along the crevice between my ass cheeks, but now it was hard, and he was gently humping me as his cock slid up and down the channel.

I felt that I had to be on the verge of having a heart attack, because my chest was pounding so hard I could feel my body shake as it beat. Walt’s hand was now raking through my pubes, avoiding my dick, for which I was grateful. I didn’t want him to touch it, and wasn’t sure it was because I didn’t want him to, or because I was ashamed of it.

If I didn’t want him to, I was having a tough time figuring out why I had an erection. When his hand eventually came down and grabbed my dick, it was as hard and as big as it was ever going to be. I let out a moan as Walt’s bony hand wrapped itself around my dick. Walt groaned as well, grinding himself into me even harder, with the underside of his cock working along my ass crevice.

Walt’s hand worked on my dick like it had never been worked on before; pulling and twisting my rigid dick, rubbing the tip of his thumb along the opening of the acorn-shaped head which was leaking precum like a faucet. As Walt’s fingers manipulated me, the back of his hand pressed hard against the spot between the base of my dick and my balls. I felt my orgasm explode at that pressure, and as I groaned in ecstacy Walt milked my dick hard, my cum spurting into the bedding for what seemed and felt like forever.

“Was that good for you Timmy?” Walt whispered in my ear, while he continued to tug on my now limp like dick.

I opened my mouth but I was unable to speak, so I just nodded my head in response. Walt pulled me over on my back and looked at me with a gentle smile, throwing the covers off of us, exposing me to the soft light of the dresser lamp. He took my hand and brought it down between his legs, placing it on the first cock besides my own I had ever touched.

Walt had to put my hand around his member, and my fingers were trembling as I felt the incredible heat that glowed from it. His cock was incredibly hard, almost muscular in a way, and the skin slid up and down loosely as I gave it a few reluctant tugs, all the time keeping my eyes averted from what I was holding.

“Haven’t you ever done this before Timmy?” Walt asked in his kind grandfatherly way. “Been with another man I mean?”

Walt’s hand reached over and took my limp dick between his index finger and his thumb, pulling on it.

I tried to say no, that I hadn’t, but my voice wouldn’t work so I just shook my head no. Walt seemed shocked at this and stopped what he was doing.

“I’m sorry Timmy,” Walt said. “I thought you… do you want me to stop?”

I looked at Walt and shook my head no. Walt smiled and bent over my dick, taking the flaccid tube into his mouth and began to suck on it slowly. The warm moistness energized me immediately as my dick found its way into a mouth for the first time.

Walt had my cock in his mouth right down to the base, and he was sucking furiously on it without moving his lips up and down, probably because there wasn’t much to go up and down on. Soon I felt my cock begin to get hard under Walt’s urging, and he began to slide his lips up and down my dick while he squeezed my nuts.

I felt myself begin to reach orgasm, but Walt eased up until the sensation went away. This happened several times, as he took me to the brink and then eased up on me. He would squeeze me in a certain way, and the just about-to-cum feeling would fade, only to return a moment later.

Time and time I would be on the verge of cumming and then be brought back down. Walt was playing me like an instrument, and it was driving me crazy. I was arching my back high, trying to get him to finish me off, and the frustration level was incredible.

Finally, when Walt had sensed I could not take any more, he began sucking my dick hard and fast. This time, Walt didn’t stop. I felt my dick erupt into Walt’s eager mouth, and he kept sucking and swallowing until I ran out of seed. Even then, my dick kept spasming for a while in Walt’s mouth, until he finally released my shrunken and withered dick.

I looked at the ceiling, drenched with sweat and exhausted from the most intense orgasm I had ever experienced. About then I realized that I still had Walt’s cock in my fist, and he smiled when I pulled on his still fully engorged weapon.

“That’s alright Timmy,” Walt said. “You don’t need to do anything that you don’t want to.”

4. I guess I must want to.

That was what I said as I got up on my knees next to Walt, who rolled over on his back when he heard what I had said. In front of me was a naked senior citizen, one with an erection. Walt’s cock was laying back on his stomach when I gingerly picked it up with my trembling hand. I put my thumb and ring finger around the base of it and began jerking him of much like I would do myself. After I realized that his cock was way too long for that method because it made it flop around too much, I took him in my fist and began pumping it.

“Here Timmy, try some of this,” Walt said as he handed me a bottle of lotion.

I squirted some in my palm and went back to pumping Walt’s cock. Walt leaned back into his pillow and sighed, idly squeezing his nipples as he watched me. I enjoyed watching the foreskin slide up and down the head of Walt’s dick as I jacked him off, and after a time Walt reached down and skinned it back down.

“Feels a little too good,” Walt said with a smile. “I want to enjoy this. You’ve never done this with other boys?”

“No,” I croaked. “I’d be way too embarrassed to let anybody see me naked. On account of my dick, I mean.”

“Why on earth would you feel that way?” Walt said as he grabbed the lotion and squirted some on his fingers.

“It’s so little,” I said while stating the obvious.

“Don’t be silly, you have a very nice cock,” Walt said. “They come in all sizes and as long as they work they’re wonderful. You’ve just had two orgasms in less than an hour and I’ll bet you’ve got plenty more left inside you too.”

As he said that, Walt reached behind me and grabbed my balls, kneading them with his oiled hand. His hand went up and found my dick, which was in the process of coming back to life again.

“See, I told you,” Walt crowed. “Now me, I’m lucky if I can have one orgasm these days.”

“Am I doing this right?” I asked Walt while my fist coninued stroking his pale white cock.

“Feels wonderful Timmy,” Walt said as he handed me back the lotion. “You can use both hands if you want to.”

I oiled up both hands and took Walt’s cock in my fists like a baseball bat. Even holding his dick like that left the entire crown exposed, and I marvelled at the size of his cock with undisguised envy. The network of veins that bulged along the shaft appeared to throb in my hands.

“I can’t believe how big yours is,” I said as I wrung my hands around and down his cock, which was still rock hard.

“I’m glad you like it Timmy, and you’re doing a wonderful job on it too,” Walt said as he made sounds that signified pleasure. “Now I’m going to do something to you, and I’ll stop if you tell me to, okay?”

I nodded and felt Walt’s hand slide down from my balls and gently stroke the sensitive area under the base of my balls. Walt’s finger continued moving until he was rubbing the outer rim of my anus. I squirmed at this new feeling, which was not unpleasant at all. Suddenly, the lubricated digit that had been stroking the outside slid into my ass. Not far, only to the first knuckle, but enough for me to jump in surprise.

Peter was talking more than ever now, timing his comments to match the rhythm of his cock as it fucked my mouth. “How do you like that in your mouth, how does that feel… Jesus, that looks good… Gonna stretch out those lips a little… Oh, fuck… fuck…”

I thought for sure that he was going to dump a load of cum in my mouth at that exact moment, but he didn”t. He pulled his dick from my mouth and then got up off the bed, and I realized that it was probably over. He was probably coming right now, and the amazing episode was going to end.

Instead, I felt a hand pushing open my ass, and then something hot and hard and wet was being guided toward my asshole.

Did he really intend to fuck my ass?

“Just the head,” he said, as if to answer my question. He sounded drunk, now, or like a possessed man. “I”m just gonna put the head inside, that”s all…”

And with that, he slid the fat, smooth head of his cock inside my ass.

He moaned with agonized pleasure, and it was a good thing he was making noise because I was unable to keep from groaning myself. His cock was unbelievably thick, but after the initial, painful shock, I could feel my ass stretching around his meat, struggling to accommodate him.

“Oh, Jesus,” he whispered. “Just… another inch…”

I almost stopped him at that point, but I knew it was too late. Peter pressed his weight forward, and at least three more inches of his fiery cock slid into my asshole. The pain was intense, and it took every ounce of self-control to keep from screaming. I struggled to relax, to accept his cock in my ass, and to still feign unconsciousness at the same time.

He pulled back until only the head was still inside of me, and then he pulled that out, too. He traced a line around my asshole with the tip of his cock, and then slipped it back inside just as I was beginning to recover from the first penetration.

“Fuck, yeah,” he said. “You know… what I”m gonna do…? I”m gonna tear your fucking ass apart, Dan, I”m gonna split you open…”

He started working his cock in and out, now, taking his time, obviously wanting this to last as long as possible. He kept himself from going in too deep, probably no more than four inches at the most, but his cock was so unbelievably fat that I really did feel as if I was being split open – as if he were assaulting me with a weapon. He grabbed hold of my hips and started pulling my ass toward him as he plunged forward, and suddenly another inch of cock was stuffed inside of me. He fucked me harder, faster, and I felt his cock grow thicker inside of me, swelling immensely, and I thought that he had to be as thick around as a fucking horse.

“What the fuck do I care if it”s too big,” he said out loud, struggling to get the words out between his uneven breaths, still maintaining his rhythm as he worked over my ass. “You can”t feel it anyway, right? What are you… going to do… about it?”

I had time to think, Oh my God, and then I felt all of Peter”s weight descend on me, and an unimaginable pain shot through my body as he slammed the full length of his staggering cock up into my ass. He kept filling me up and it seemed that it would never end, that it would go on forever, and then I felt his balls slapping against mine and I knew that all of it was inside me, every monstrous inch. And I was letting it happen.

He didn”t wait for me to recover. Immediately he started pumping away, using short, powerful thrusts that kept him as deep as possible inside of me. And even that didn”t seem to be deep enough for him. Sweating and panting, he lifted my right leg and turned my body slightly, so that I was lying on my left side and facing away from him. He repositioned himself to straddle my left leg, so that he was actually fucking me sideways. Then he pushed my right leg up and out of the way and slid forward at least another inch, sending a shockwave of pain and agonized pleasure through my ass as he ripped me open in a new direction.

“Oh my god,” he said. He kept saying it, again and again, as he lengthened his strokes and did his best to break me into two pieces. He was slamming into me with such force that my whole body shook when he hit me, and I was actually being pushed off the bed. Peter didn”t care. The only that mattered to him was fucking me, tearing me open with his amazing and terrible cock.

“I”m gonna cum in your ass,” he said. “Gonna fill you up… make you take it up your ass, take every inch and every fucking ounce of cum…”

I barely understood what he was saying because I was almost delirious by this point. My ass was finally getting a little numb from the rape, and I found that I could even tighten myself around him now. I knew that would make him come even sooner, and that”s what I wanted – not because I wanted it to end, but because I wanted his cum in my ass, I wanted him to empty himself inside of me, over and over again, and then I wanted him to do it again, as many times as he wanted, until he finally used me up and exhausted himself.

He suddenly cried out and fell into me, and then I felt it: blazing hot liquid erupting from his cock in wave after wave as the orgasm hit him, filling me with his cum until I thought I would burst. He didn”t stop fucking me as he came, ramming into me so hard that he was actually lifting my body off the bed now with his pounding, lifting me up with the strength of his cock and his powerful strokes, as if I”d truly been impaled.

Finally he collapsed on top of me, completely spent. I could still feel his cock pulsing inside me, and I squeezed it as tight as I could, as if I could suck it dry with my ass. Peter shuddered against me and I felt another wave of cum blast through my insides.

It took about ten minutes before Peter could move again. He finally pulled his cock out of my ass and rolled off me, leaving only his cum inside me. He had fucked me so deeply that there was no mess for him to clean up – all of his cum was buried deep inside me, far up my shattered ass.

A few minutes later he turned out the lights and went to sleep.

I didn”t bother moving or changing position on the bed. I liked the idea that if he got up in the middle of the night, he”d have a good look at the ass he had just fucked so violently. And I wondered how the hell he would try to explain this in the morning…

At some point I fell asleep.

When I awoke, many hours later, my ravaged asshole was the first thing I noticed. The next thing I noticed was a note that had been left on my pillow, from Peter: “I caught an early flight back this morning after the brunch, but didn”t want to wake you up. You got back to the room pretty late last night and I thought you could probably use the sleep. Hope you had a good time wherever you went.”

I chuckled painfully at the note, tossed it in the wastebasket, and walked on unsteady legs to the shower. Peter may have been gone, I knew, but he”d left more than the note behind. I could still feel his cum inside me, some of it even running down the insides of my thighs as I stepped into the shower. Despite the soreness, I decided that we”d probably both had a pretty good time.