The Mystery Man! (Gay Themes)

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This story contains adult sexual content and should not be read by those under 18, or considered minors in their country or locale. If you are under 18: CLICK HERE

This fictional story is the artistic expression of the author who wrote it. The Small Dick Club strongly believes in freedom of speech, and the right of artists to be heard, especially if what they say pushes the boundaries of what is acceptable in society. If you think you won’t like the content of this story, then don’t read it. It’s that simple. The Small Dick Club wishes to advise readers that any similarities in these stories to actual or real people or events is purely coincidental and unintended. That any story marked as a ‘true story’ shouldn’t be taken literally, as we have no way to verify if stories submitted to us are true. The Small Dick Club takes no responsibility for the imaginations and literary creations of authors who post their stories here.
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Chapter One:

Jeremy Quinn nursed his chocolate shake while he sat at the back of the fast food restaurant, eyes peering over the rim of his glasses in search of the person he was supposed to meet that night. He was terrified, and tried hard not to show it, but Jeremy was not a lad who hid his emotions very well.

Sitting alone in the rear corner, Jeremy had been watching intently as people had come in and out of the place for the last half hour or so. All of them were there to get some food, or just perhaps to come in from the rain that had become a steady drizzle.

Jeremy hadn’t come in for the food, and didn’t really want the shake he had been drinking, although it might put a little weight on his spindly 5″9″ frame. He was there to meet somebody. A “friend” that he met on-line who wanted to meet him very badly, or so he had claimed when they chatted.

The man’s name was Gary, and he said he was 28, which made him ten years older than Jeremy. Gary said that he didn’t care about things like age, because he liked younger fellows. Besides, Gary had told him, he felt much younger than he was, and in his conversations the man seemed to know a lot about video games and popular music.

More than Jeremy knew, he recalled, which didn’t take much because Jeremy wasn’t much interested in things like that himself. He preferred to concentrate on his studies, and didn’t care about rap music or the video games that guys his age were into.

Jeremy also had another interest, one that brought him into contact with this Gary. It was largely an unfulfilled interest so far, but something that he had been curious about for a long time, so when he found himself on a website with men which similar interests, one thing had led to another, and that led him here.

Jeremy liked guys. All of his life he had been curious about what it would be like to be with a man. Of course, he also had dreamed about what it would be like with a woman too, but outside of some awkward necking and petting with Susan Hoover from the debate team, that was all fantasy too.

He had done something with a friend once, just last month. They had gotten a bottle of rum out of his friend Alan’s house and had gone into the woods behind his house and gotten wasted. Well, Alan got wasted. Jeremy had mostly pretended to drink, and after a short time the talk had turned to girls and who they most wanted to fuck.

Since Alan had actually done that to girls, Jeremy mostly listened and managed to get the conversation turned around to how horny they were. When Alan had said that he would end up going home and jerking off, Jeremy had surprised himself by boldly saying that he would too, and added that they should jerk each other off.

Alan had agreed, although he was so wasted by then he might not have realised it, and Jeremy managed to get them over to a grassy place on the side of a hill. There was a full moon and clear skies, allowing Jeremy to see everything that was happening.

Alan had taken his pants down just before falling the short distance to the ground. Jeremy’s trembling hands had pulled down Alan’s briefs as quickly as he could manage, and there it was. Alan’s cock.

Jeremy had seen it many times over the years, in the showers at school and peeking over at urinals, but this was different. Not only was he going to see it, but his hand was reaching over and holding it. It was warm and rubbery to the touch, and when Jeremy’s shaking hand pulled on the flaccid tube, he was shocked at the elasticity of it.

“How’s that?” Jeremy asked as he wrapped his fist around the dark beige cock, which was getting thicker and longer as he pulled on it.

“Good man,” Alan slurred. “Should get some babes back here.”

“Maybe later,” Jeremy said, stunned at how large his friend’s manhood was getting, and he wasn’t even hard yet.

Alan would never get a full erection, but under Jeremy’s enthusiastic hand, he did cum, his seed oozing out of his semi-turgid organ while Alan lay in a semi-conscious state. Jeremy looked down at the back of his hand, which had a long rope of Alan’s cum on it.

Jeremy brought his hand up to his mouth and let his lips touch the still-warm semen. After tasting it, he looked down at Alan, who was now either sleeping or passed out, and licked the cum off of his hand.

“I should have done it,” Jeremy mumbled to himself as he looked down at Alan, his cock now spent and resting on his hairy balls.

Alan wouldn’t have remembered – indeed, the next day when they had spoken Alan told Jeremy that he was so drunk that he didn’t recall what had happened, and was in fact grateful to Jeremy for getting him home okay.

Jeremy remembered though. He remembered everything. He remembered kneeling next to Alan and putting his lips on his dick, peeking up at Alan to make sure he wasn’t looking at him, and then taking his cock into his mouth.

The fat dick tasted salty, and filled Jeremy’s mouth as his lips went down to the base of his tool in his pubes. He never would have been able to do that if he was hard, Jeremy thought. Alan was probably 6 or 7 inches erect, and as he sucked gently on the limp dick in his mouth, he regretted not doing this long ago.

“Here,” Jeremy said to his friend. “Do me.”

Working his pants down his thighs, Jeremy took Alan’s hand and wrapped it around his cock, which was throbbing and erect just as it had been all this time. Part of Jeremy wished that Alan was awake, so that he wasn’t forced to hold Alan’s hand around his dick like this, yet another part of him was just as glad.

Jeremy would have been too ashamed to let Alan see his dick, especially after seeing how big Alan’s was when it wasn’t really even hard. The dick that Alan was involuntarily holding was not as long and not nearly as thick as his own, his friend’s fist covering up all but the tip of the acorn-like glans.

Jeremy thrust his hips a few times and it was over, as he ejaculated all over the grass within a matter of seconds. He took Alan’s hand off of his dick and cleaned it off, and got both of their pants up – pulling up Alan’s very reluctantly as Jeremy thought he could stare at that beautiful cock all night – and managed to stagger home with his friend without incident.

Ever since then, Jeremy had thought about that night and wanted it to happen again. He was afraid to ask Alan to do it, because when he had mentioned anything remotely resembling it, Alan had laughed it off like he was kidding.

So this was what led Jeremy to the computer and for this rendezvous, and Jeremy had been so engrossed in thought that he hadn’t even noticed the man standing down at the other end of the dining area, sipping a coffee.

That couldn’t be him, Jeremy thought. This guy was older than 28. Huskier that the picture he had on his ad too, and his reddish-brown hair was thinner too. He did look a little like the picture though, and when he smiled at Jeremy and got up and walked toward him, Jeremy knew that it was him. It was Gary.

“Jeremy?” the man asked, and he managed to nod in response.

“Hi, I’m Gary, obviously,” the man said, extending a beefy paw that enveloped Jeremy’s sweaty hand in a firm grip, and casually slipped into the seat opposite him.

Chapter Two:

“So where is he?” Gray said as he placed his elbows on the plastic table.

“Who?” Jeremy asked, his voice rising to an feminine pitch despite his best efforts to stay calm.

“Chris Hanson,” Gary said, snickering. “The guy on that show that catches predators? I have transcripts of all of our conversations. You said you were 18 on several occasions.”

“Huh?” Jeremy asked, bewildered at the older man’s rapid fire comments and obviously unaware of what Gary was talking about. “I am. 18, I mean.”

“Really? You don’t look it,” Gary said, still appearing a bit antsy as he looked around the room. “What was your birthday again? I forgot,”

“April 15th,” Jeremy answered as he looked at the man across the table, and his stare must have been noticed.

“What’s wrong?” the man asked

“Nothing,” Jeremy said, staring at the man’s hands as they cradled the coffee cup. “It’s just that you don’t look like the picture.”

“Oh that?” Gary chuckled, thinking of the photo that had to have been taken at least 10 years ago. “That’s me alright, but it’s not very recent, is it? I guess I should get another one taken. I hope you aren’t too disappointed.”

“No,” Jeremy answered with a shrug.

“Because I’m certainly not disappointed in you,” Gary told the nervous young man. “Not at all. You look just like that photo you sent me. Was that your senior yearbook picture?”


“I was hoping you were going to send me something a little more personal, but that’s okay,” Gary assured him. “Adds to the suspense, although I have to admit that I’m usually pretty good at sizing guys up, and frankly I couldn’t picture you with – how did you describe it? Didn’t you say you were packing seven thick inches of throbbing man-meat?”

Gary watched his young friend turn crimson at the recognition that he had remembered how he had described himself to him on-line, and his reaction certainly indicated that he might have been exaggerating a tad.

“I – copied that line out of a story I was reading on a website,” Jeremy admitted sheepishly.

“Oh, I love reading online erotica stories! They make me so horny!,” Gary said with a smile.

“Yeah me too,” Jeremy said

“So what part of that description of your cock was wrong?” Gary asked. “The 7″ inches or the thickness?”

“Both,” Jeremy whispered.

“I see,” Gary said with a sigh, reaching over the table to pat Jeremy’s hand. “So here we are. A man who shows up looking 15 years older than his picture, talking to a guy who fabricated his description. Like neither one of us was going to find out eventually?”

When Gary heard the man’s robust laugh he began to laugh himself, relaxing a little as he realised that the man wasn’t mad.

“I don’t really care all that much about that sort of thing,” Gary admitted.

“That picture of you – that other picture?” Jeremy asked. “That wasn’t you then, right?”

“Oh, that was me alright,” Gary said quickly. “Maybe I had the ruler pressed into me a bit, but what you saw is what I have.”

Jeremy swallowed hard as he recalled the picture that Gary had sent him. It was a photo of an erect penis resting on top of a yellow plastic ruler, with the tip of the huge phallus reaching a little beyond the 9″ mark. Jeremy had the photo burned into his memory bank, and had spent considerable time pleasuring himself while gazing at the intimate image.

“You okay?” Gary asked.

“Sure,” Jeremy said, his nerves reappearing suddenly.

“Now let’s get back to you,” Gary said, lowering his voice as a couple went past them on their way to the counter. “You said that you had only been with one guy before?”

“Yeah, and he was kind of out of it at the time.”

“And that was it?” Gary asked with a tone of disbelief in his voice. “Doesn’t seem possible seeing how cute you are, although you certainly are shy.”

“Can’t believe I’m actually here,” Jeremy admitted. “I figured I would chicken out.”

“I’m glad you didn’t,” Gary said. “But how do you know that you’re gay? Just from that one time?”

“No, I mean, girls don’t really do much for me. I’ve always looked at other guys. Like in gym class and stuff, and wondered what it would be like.”

“And here you are,” Gary said, exhaling as he looked over his prey. “What do you think? About me? Us?”

“I don’t know.” Jeremy said.

“Well, I know how I feel,” Gary replied. ” I would love to be your first real experience, but only if you want me too. Do you like me?”

“Yeah. I mean, you seem like a nice guy.”

“I am, and as a matter-of-fact when I think about you with some of the guys that are out there,” Gary opined, letting the words trail off. “Let’s just say that I promise you I’ll be good to you. I’ll be patient and do whatever you want me to do.”

Jeremy felt the sweat trickling down his sides as he thought about the other times. Not just the time with Alan, but the time at the movies when that man had put his hand on his leg, and the time that man had given him a ride and then told him what he wanted to do to him. Those times Jeremy had run, even though he later regretted it. Now?


“You sure?” Gary asked, leaning closer to Jeremy, who nodded.

“I can get us a room across the street,” Gary explained, gesturing over at the chain motel on the other side of the highway. “As long as you’re sure.”

Jeremy found himself nodding again, and the man leaned closer.

“Tell me. Don’t just nod. Tell me that you want to be with me tonight.”

There was a moment of silence, after which Jeremy nodded again, and in a voice barely audible managed to say what Gary wanted to hear.

“I want to be with you,” Jeremy said. “I want you and me to do stuff together.”

Chapter Three: The motel.

It was a typical motel chain, one that was pretty much like the rest of them, and after Gary drove the two of them across the street and went into the office, he came out and got Jeremy out of the car.

“Room 227,” Gary announced, pulling a gym bag out of the trunk and coaxing Jeremy out of the car.

Jeremy followed Gary up the stairs and down the long hallway until reaching the very end.

“227!” Gary announced as he swiped the card key and got the click in response. “Maybe that will be your lucky number in the lottery or something.”

The room was cool, which was a welcome break from the humidity that had followed the rain of the evening, and Jeremy watched Gary click on the TV and set his bag onto the bed, extracting a bottle of rum.

“Is this the right brand?” Gary asked, holding up the bottle.

“I guess,” Jeremy said, remembering that he had told Gary that he liked rum, even though he wasn’t much of a drinker.

“There’s a vending machine down the hall,” Gary said. “I’ll be right back.”

Jeremy watched the man leave and walked over to the gym bag and looked in it. Inside were a fake dick still in a package, a bottle of lubricant and a pair of handcuffs.

“Handcuffs?” Jeremy said aloud as he sat on the edge of the bed, holding up the black and silver bracelets just as Gary came back into the room with a couple of cans of Coke.

“You like?” Gary asked, and smiled when Jeremy shook his head violently. “That’s okay. I like it better when guys stay because they want to. We won’t use them if you don’t want. Here. I thought we might need something to mix with the rum.”

Jeremy dropped the cuffs back into the bag and took the cup from Gary, guzzling the drink down as fast as he got it, and Gary made him another one that Jeremy downed just as fast.

“Slow down,” Gary chuckled, putting his hand on Jeremy’s forearm and sliding it up and down his soft skin. “I want you to remember all of this. Why don’t you stand up so we can get you more comfortable?”

Jeremy stood up and faced Gary, looking up at the man that was several inches taller than him, and when the man reached up to the top button on his shirt Jeremy started looking around like a frightened animal.

“Can we?” Jeremy asked. “The light?”

“Sure,” Gary said, going over to the switch and dimming the room a bit before returning to Jeremy.

“Now where was I?” Gary asked, smiling as his fingers methodically went down the row of buttons until they were all free before opening Jeremy’s shirt and pulling it off his bony shoulders.

“Nice,” Gary said, putting his beefy hand on Jeremy’s scrawny chest and making slow, circular motions over Jeremy’s nipples. “So nice. Oh. I can feel your heart beating.”

Gary’s hand rested for a second over Jeremy’s heart, actually able to feel the strong muscle pounding away wildly, before resuming his stroking.

“What a beautiful body you have. Wish I was as slender as you are. And so smooth too,” Gary mentioned as his fingers glided over Jeremy’s chest and up to his shoulders.

Jeremy was startled when Gary took him by the elbow and raised his arm behind his head. Jeremy resisted for a brief second before letting Gary do as he wished.

“Oh my,” Gary said softly. “Do you shave your armpits?”

Jeremy shook his head no, blushing as Gary looked at the tiny cluster of brown hairs nestled deep in the sunken hollow of his armpit.

“Better yet,” Gary said before moving his head down and letting his tongue slide up and down Jeremy’s armpit.

Jeremy shuddered as he felt Gary’s wet tongue slithering all over his underarm, pasting the hairs against his moist skin before raising his other arm and repeating the act, and by the time Gary was done Jeremy’s head was spinning.

“Sweet,” Gary said, letting Jeremy’s arms down so he could deftly undo the young man’s belt.

The teenager’s jeans dropped to the carpet right away, and as Gary knelt to help Jeremy step out of them he saw the modest bulge in his underwear that his affection had probably caused.

Gary slid his hands along the inside of Jeremy’s calves as he took his socks off, feeling the light dusting of hair on his trembling legs, and when Gary rose to his feet again he saw the sweat dripping down Jeremy’s face.

“You liked what I did, didn’t you?” Gary said, letting his hand stroke the bulge that went toward Jeremy’s right hip, feeling the rigid tube through the white cotton. “Why don’t you help me get comfortable too?”

Gary waited a moment before taking Jeremy’s hands up to his shirt and getting him to unbutton it. It was a task made longer than it should have because of Jeremy’s nerves, but the delay only added to the anticipation.

“There,” Gary shrugged as he pulled off the shirt, exposing his husky chest, the slight swell of his man-boobs visible under a coat of reddish-brown hair that covered him from the neck down. “Guess I should work out some more. What do you think?”

“Soft,” Jeremy whispered, his hands sliding through the fleecy texture of his chest hair.

“That feels nice,” Gary said, raising his arms to link his hands behind his head, his biceps bulging as he did.

Jeremy timidly let his hands slide over, letting his fingers rake through the thick tufts of hair under the older man’s arms, wondering whether he was supposed to do what Gary had done to him. His armpits had a woodsy, musky aroma that filled the room as Jeremy’s fingers continued to play.

He even has more hair under his arms than Alan does, Jeremy noted. Way more chest hair too, and as Jeremy looked downward he realised that Gary probably had more of everything than Alan had, and he wanted to find out for sure.

Gary smiled when he saw where Jeremy’s hands were headed, and after the lad undid his belt and helped him off with his pants, he revelled in watching Jeremy’s reaction when he saw the bulge in his boxers. He let Jeremy touch the bulge briefly before stopping him.

“Me first,” Gary said with a smile, kneeling before the skinny teen and taking the elastic of his briefs in his hands.

Gary eased down the briefs, and when Jeremy’s cock sprang out from captivity, Gary almost came from just looking at it. The thin pale tube was springing around wildly as Gary took the briefs down, and a glance under the erection revealed a healthy pair of nuts in a wrinkled hairless pouch.

“Sorry,” Jeremy said sadly. “I know my dick is little.”

“It’s beautiful,” Gary sighed as his fingers caressed the modest wisp of hair above Jeremy’s dick, which couldn’t have been more than 4″ long at best.

Gary took the acorn-like head of Jeremy’s dick into his mouth, licking the glans before letting his mouth slide down the shaft of Jeremy’s boyhood. Not much bigger than a thumb in length or girth, the rock-hard dick jumped around in Gary’s mouth as his lips reached the base of it before sliding back up to the tip.

“You like that, don’t you babe?” Gary asked as he looked up at Jeremy, whose face was strained as he looked down at Gary with pleading eyes. “You want to cum, don’t you?”

Gary went back down on his cock, but every time that he felt Jeremy near orgasm, he would back off. Jeremy’s legs were shaking so badly, and his moaning was so pleading in nature that Gary wanted him to get off really good.

Gary went under Jeremy’s dick and began sucking on his balls, one at a time. The cum-filled orbs were surprisingly big considering the modest-sized prong springing above them, and Gary relished letting them roll around in his mouth before allowing them to pop out loudly.

Jeremy’s dick was dripping now, the string of pre-cum landing on Gary’s neck while he sucked the young man’s balls, and Gary decide to put Jeremy out of his misery. Cupping his skinny ass in his palms, Gary brought him into his mouth again, but this time he did not stop.

Gary felt his Jeremy’s cock surge a second before he felt his cock spurt hot seed down his throat. Gary squeezed and kneaded the lad’s buttocks while he kept sucking, and it seemed like Gary’s hands were holding the young man up by the time that his cock finally stopped ejaculating.

His lips pulled themselves back off of Jeremy’s limp spout, and as Gary savoured the musky taste of the young fellow’s cum he looked up at Jeremy, who seemed dazed as he stood on unsteady legs.

“Was it as good as you had hoped?” Gary said as he rose to his feet to face Jeremy, who surprised him by wrapping his arms around Gary after nodding.

“That feels nice,” Gary said, enjoying the feel of Jeremy’s smooth body. “We feel good together.

Chapter Four: Don’t look.

They embraced for a time before Jeremy stepped back, looking down Gary’s body, which was clad in only boxer shorts and socks, and was torn as to what to do next.

“Um – don’t look at me, okay?” Jeremy asked, and Gary shrugged and nodded, knowing that this was not a promise he was going to be able to keep for long.

Gary knew that Jeremy was self-conscious about what he was going to do – what he wanted to do – so he tried to not watch as Jeremy knelt down and took his socks off.

Jeremy’s hands were shaking worse than ever as he got Gary’s socks off. He was so hairy, Jeremy noticed, right down to his ankles. Didn’t seem fair, he thought, recalling how he had spent his whole life waiting to become as manly as Alan, and now Gary.

The boxers were right in front of him, and as Jeremy fiddled with the socks his eyes went to the bulge inside the loose fitting green and white boxers. When he could delay no longer Jeremy glanced up at Gary, who stood looking straight ahead, and then unsnapped the clasp of the boxers.

The briefs came down past the bush of hair before the base of Gary’s cock appeared. Thick – absurdly thick thought Jeremy as the stump of it appeared – and as the boxers got lower and lower and kept revealing more and more of Gary’s cock Jeremy almost started hyperventilating.

When Gary’s manhood was fully exposed, Jeremy was startled; first because he kept expecting for the ridge of the crown to appear, and it never did, and secondly was the realisation that Gary’s cock was huge and wasn’t even hard yet.

Gary wasn’t circumcised, which was not evident in the photo he had sent which obviously showed the foreskin retracted, and as Jeremy gawked at the cocoon-like hose that dangled between Gary’s legs, he thought that it looked even more intimidating like this.

Glancing up again to make sure Gary wasn’t watching, Jeremy put his hand on the huge organ and tried to get his hand around the fat shaft. As Jeremy’s hand moved, the foreskin slid back, exposing the plum-sized glans that looked as big as an apple to him right about then.

“Watch the teeth, babe,” Gary said as Jeremy put his mouth around the exposed crown. “Open wide. That’s it. Oh yeah. Suck that cock now.”

Jeremy held the shaft of Gary’s cock in both hands, the loose skin sliding up and down while Jeremy tried to get more than the knob of it into his mouth without gagging. Soon the shaft began getting harder and his cock began to get even longer.

Thankfully it got no thicker, as Jeremy’s mouth was already stretched to the limit, but he gradually began to get his lips beyond the ridge of the crown, and as Jeremy’s fists gripped the rest of the gigantic organ and milked it he heard Gary groan.

“Oh man, Jeremy,” Gary exclaimed. “You’re a natural born cocksucker. That’s it. You like my cock?”

“Yes,” Jeremy gasped, pulling his mouth off of it while continuing to milk it with his hands.

“You said you to like to look at guys with big cocks, like your friend’s,” Gary said through his heavy breathing, pulling his huge organ out of the lad’s mouth for a second, waving it around like a magic wand. “Is mine big enough for you?”

“Yes,” Jeremy said before taking Gary into his mouth once again, and Jeremy remembered how big he had thought that Alan’s penis had been at the time, a thought that seemed absurd given the size of the enormous cock he was now stroking.

“I’m gonna cum soon,” Gary said. “You don’t have to take it, if you don’t want to. I understand.”

Jeremy couldn’t decide what to do, but by the time he made up his mind, it was too late. He heard Gary groan as a rope of cum spat into his mouth.

Gary looked down through glazed eyes as he watched Jeremy swallow a little before moving his mouth off of him. Choking a bit, Jeremy kept pumping his cock, allowing Gary the pleasure of watching his cum spray all over the young man’s face, making him feel like a porn star as his cock spat rope after rope of his seed at the lad.

Jeremy kept milking Gary’s cock long after he stopped coming, blinking as the cum got into his eyes, but not stopping until the head retreated back into the cocoon and he was limp once more.

“That was so good,” Gary said, helping Jeremy up so that he could clean his eyes, which no doubt burned from the cum, before easing him down to the mattress.

“I see you’re already coming back to life,” Gary noted, reached down and cradling Jeremy’s semi-turgid dick in his hand. “You’re also starting to relax a bit aren’t you?”

“Yes,” Jeremy answered, enjoying the man’s fingers on his dick.

“I can help you relax some more,” Gary said, reaching into his bag and pulling out some lotion. “Why don’t you roll over on your stomach and let me give you a rubdown?”

Chapter Five: Gary’s hands.

Gary started at Jeremy’s feet, and as he kneaded the young man’s calves he could feel the tenseness start to evaporate, only to feel Jeremy start to get rigid as he worked the backs of his slender thighs.

“Why are you getting tense again?” Gary asked has his hands reached the modest swells of the lad’s buttocks. “This is supposed to relax you.”

“That stuff,” Jeremy mumbled into the pillow. “In the bag.”

“What about it?”

“Are you going to use it on me?”

“What exactly?”

“The dick and the handcuffs,” Jeremy said. “Are you going to try to put your dick in my ass?”

“Not if you don’t want me to,” Gary said, squeezing the oiled cheeks with a slow kneading touch.

“Doesn’t seem possible,” Jeremy opined. “I mean, you dick is so big.”

“You would be surprised at how elastic this little balloon knot can be,” Gary explained, holding Jeremy’s ass cheeks apart and gazing at the hairless beige opening before moving his greased index finger to the puckered ring. “Now just relax.”

With a deft spinning motion, Gary dipped his digit into the tight opening for a brief second before pulling it out. Jeremy had gasped twice, once going in and again going out, and he did not protest when Gary penetrated him again.

“Not so bad, is it?” Gary asked, and when Jeremy agreed Gary asked him to get up on his hands and knees. “Don’t worry. I just want to enjoy the view and play some.

Jeremy did as he was told, and let Gary position him so that his butt was in the air and his legs were spread. Gary exhaled loudly when he saw Jeremy’s balls hanging down in their wrinkled, hairless pouch, and when he grabbed the orbs and began to roll them around in his palm Jeremy moaned in response.

“You like these big boys played with, don’t you?” Gary asked. “And your cock is hard again too.”

Jeremy was squirming and rocking on the bed and when Gary’s free hand went back to Jeremy’s anus, the young man barely flinched when he dipped a finger back into him.

“Let’s try something else,” Gary said, reaching over and pulling out the dildo, lubricating it while savouring the sight up Jeremy’s exposed anus, about to be stretched out a little more.

“OH!” Jeremy gasped when the head of the dick entered him, and it wasn’t as hard as he had feared, but had a rubbery feel to it.

“Nice, isn’t it?” Gary asked as he gently nudged a little more of it into Jeremy with each soft thrust, while his free hand went back to those beautiful nuts.

Gary had about half of the six inch appliance inside of the lad, and when Jeremy began moaning louder he worked a little more of it inside of him. Now Jeremy was groaning loudly and writhing, actually pushing himself back into the thing so that soon virtually the whole thing was inside his ass.

Suddenly, Gary felt Jeremy’s balls jump in his grasp, and when he glanced down he saw the semen spitting onto the bedding beneath the young man. Gary’s hands slid off of the greased sac and grabbed Jeremy’s dick, which was now limp, and gave it a couple of pulls to drain him completely before rolling him over.

“We’ll just keep that in there for now, okay?” Gary asked, leaving the cock buried right where it was. “You seem to like it well enough. Sure you’ve never had anything up there before?”

“My finger,” Jeremy confessed.

“I’ll bet when you did it you were wishing it was your buddy’s cock, right?” Gary asked, and grinned when he nodded. “How would you like to put your cock in me?”

Jeremy looked at Gary as he straddled Jeremy’s hips, his flaccid cock draped over Jeremy’s drained dick and their balls rolling against each others.

“I’ll bet you can get it up pretty fast if we just do this for a time,” Gary suggested as he began moving back and forth, their cocks rubbing together. “Feels good, doesn’t it?”

“Yes,” Jeremy said, strangely aroused by the sight of the older man’s huge member visually crushing his own little stem, and the tip of the glans peeking out from the foreskin with each forward motion.

What would that be like? Jeremy wondered that as he stared at Gary’s manhood, which was beginning to get a bit more rigid as their cocks rubbed together. The fake dick felt nice, but Gary was so much bigger that it didn’t seem possible that he could fit it inside of him.

Now Jeremy knew he could easily put his dick inside of Gary, and that idea was more appealing for the moment. Just thinking about it made him start to get hard again, although it would take some time to get it up completely.

Gary continued to grind his gonads into Jeremy’s, and as he got harder he wondered whether Jeremy would let him do what he wanted. The kid seemed like a natural bottom, and judging by the way he was reacting to the dildo still in his ass, he might just say yes.

“Can I?” Gary asked, his cock throbbing as he straightened up and knelt between Jeremy’s thighs. “Can I take you in the ass?”

Jeremy’s eyes were fixed on the thick tool which was standing straight out and pointing at him, trying to imagine what it would feel like.

“You like what’s up there now,” Gary continued, taking his cock in his hand and sliding the foreskin back. “This will be so much better.”

“You’re way bigger than that thing is,” Jeremy protested.

“But this is flesh and blood. Not rubber. Not nearly as hard,” Gary explained. “And I’ll be so gentle to you. Please let me be your first.”

Chapter Six: Jeremy’s first.

Gary’s heart was racing as he knelt behind Jeremy, the sweat pouring off of his body despite the coolness of the room. In front of him, the skinny teenager knelt with his face in the bedding and his bony little butt raised high.

The dildo had just been pulled out by Gary, and after the older man squirted lubricant into the lad’s still-gaping orifice, he squirted his cock generously with more of the same. Such a sweet looking ass, Gary thought. Virginal before the entry of the plastic appliance, and now about to be stretched out even further by his throbbing cock.

“Ready, babe” Gary asked, running his hands up and down Jeremy’s pale back before bringing the tip of his member up to his anus. “Just relax, Jeremy. I’ll make this so good for you.”

A minute later, Gary was still trying to soothe Jeremy’s nerves as he whimpered into the pillow. He had been unable to get the ridge of his glans into the tiny opening and Gary had been unwilling to force the issue, but he was afraid that Jeremy was going to bolt any second.

Gary reached out and felt for Jeremy’s dick, finally finding the little toadstool as it seemed to be trying to retreat into his body. Gary massaged the little stem before reaching down and rubbing the lad’s balls, which had also shriveled up.

“It’s okay babe,” Gary said as he pulled Jeremy closer to him and prepared to push himself into the lad. “You know how bad you want it. Me too.”

Gary forced himself not to listen to Jeremy’s whimpering, which turned into sobbing as Gary pushed hard into the lad, and just when it seemed like it was not going to happen, Gary started wiggling his hips as he pulled and the crown of his cock popped right into Jeremy.

“There!” Gary gasped with relief as he caught himself before lunging in any farther while Jeremy cried softly. “That’s my man.”

Gary kept relatively still, trying to let Jeremy get used to the size of what was inside of him, before very gently making slight nudges of his member. The motions were almost imperceptible, and Gary resisted the urge to plunge his tool deep into Jeremy’s bowels.

It took a couple of minutes before Gary had gotten any progress, but as Jeremy’s sobs turned into little gasps, Gary could feel the lad’s hips moving back into him. Just as subtle as Gary’s own movements had been, but nonetheless it was happening.

“Oh yeah,” Gary sighed as he leaned over Jeremy as slid his soggy chest hair over the lad’s back, and a reach around found Jeremy’s dick regaining some energy. “You’re liking it now, aren’t you.

Gary leaned back and looked down at his cock, half of which was impaled in Jeremy’s anus, and the sight sent a shiver through Gary’s body. Grabbing Jeremy’s hips, he began to thrust himself in and out, and after feeling Jeremy continue to move back into him, inched further in.

Soon Gary was just kneeling there, moving Jeremy’s hips up and down his cock, letting the lad take as much of it as he wanted, and to Gary’s amazement he wanted almost all of him. When Gary’s hand reached around this time, he felt Jeremy’s dick as hard as it could be.

Gary felt his orgasm roaring through his loins, and as he started to cum he pulled his cock almost all of the way out of the lad, leaving just the crown inside as he came, bathing Jeremy’s insides with what felt like an ocean of cum.

Beneath him, Jeremy was ejaculating as well, the sensation of Gary’s seed making him cum as well. When Jeremy could stand it no more, he collapsed onto bed, with Gary crashing right down on top of him.

It took a bit of time for Gary’s flaccid cock to finally slide out of Jeremy’s cavity, and after it did Gary eased down alongside of the lad and wrapped his arm around him.

“Did you like it, babe?” Gary asked.

“Yes,” came Jeremy’s voice, and after snuggling with the lad a few minutes he found himself drifting off to sleep.

Gary wasn’t sure how long he slept. Outside it was pitch black and inside the room was still faintly lit. The TV was still on, and judging my the late night host that was on the screen he must have been out a couple of hours.

Gary might have slept longer but he had been awakened first by the very pleasant sensation of Jeremy’s tongue sensuously licking his armpit and then with his lips around his cock, trying to coax him into an erection. That had been managed a minute ago, as Gary managed to feign sleep throughout Jeremy’s inexperienced but earnest efforts, but there was no way that he could sleep through what followed.

Jeremy was crouched over Gary’s cock, the lad’s fist clenching the shaft of the pillar as he squatted over it. He was facing the same way as Gary was, giving the older man a delicious view of Jeremy’s freshly oiled crack as it met the head of his cock.

It was still a tight fit, but Jeremy was not crying this time as his anus swallowed up the bulbous head of his mentor’s manhood, and as he lowered himself further Gary grabbed his hips for support.

“You love that big cock of mine up your ass, don’t you?” Gary grunted. “I knew you would. You’re almost taking all of it.”

Jeremy’s response was to ride the older man’s cock like a cowboy, and after a few minutes of this Gary asked the lad to swivel around.

“I want to see you,” Gary grunted. “Want to look at your cock while I fuck you.”

With the limberness that comes with youth, Gary managed to help Jeremy rotate his body without disengaging, and as Jeremy faced him, leaning back on his heels as Gary impaled him to the hilt, the lad’s enjoyment was clearly evident.

Jeremy’s cock swung up and down violently as he rode Gary’s tool, the slender prong slapping his stomach before swinging down and grazing Gary’s belly. Gary reached out to grab the wildly swaying dick but changed his mind, enjoying the view too much as it was.

Jeremy’s eyes were glazed as he kept moving up and down on Gary’s cock, the squishing sounds of the lubricant and his heavy breathing the only sounds. Gary was trying not to cum, wanting to make this last as long as he could, but when Jeremy started to make a squealing sound that changed.

Jeremy made a loud and piercing sound, and as he did his cock began to spurt, spitting out strings of cum all over Gary as he ejaculated without touching his dick. That sight sent Gary off, sending a load of his cum deep into Jeremy as he fell down onto him, impaling himself completely on his manhood.

“Wow,” Gary finally said after Jeremy slid off of him and collapsed on the bed, too exhausted to move, and as the cum oozed out of the lad’s orifice Gary squeezed the butt cheek and rubbed the back of his thigh. “You’re amazing.”

It was four in the morning when they finally left the motel room, another orgasms and a refreshing shower later.

Jeremy had tried to get him hard again in the shower, kneeling before Gary and sucking and pulling on him enthusiastically, even slapping his own face with Gary’s very limp cock before the older man pulled him to his feet.

“No use,” Gary had said. “I’m not as young as you are, and I haven’t had this many orgasms in one night since I was your age. I’ll take my vitamins so I’ll be ready for you next time.”

“There’s going to be a next time?” Jeremy asked, and Gary looked at him like he was mad.

“Are you serious?” Gary said, glancing down at the dick that was pointing at him.

Gary sunk to his knees, letting his mouth glide slowly down the length of the slim tube while his hands cupped the wet ass of the lad.

“Tonight?” Jeremy asked as he leaned back and felt his balls being milked while his dick got played like a flute once again.

“Okay,” Gary gasped before going back to the task at hand, and although he didn’t know where he would get the energy from, he was not going to ever say no to Jeremy.

by timmywells

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