Chat Room Exploration

Jeremy Quinn was a very shy young man who tended to freeze up in social situations. Add that to the fact that he was very unsure of his sexuality and lacked confidence in himself, and it was easy to see how he became so vulnerable to the advances of a man who was not quite what he appeared to be on-line.


Chapter One: The mystery man.

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 realized 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?

“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 this website called literotica,” Jeremy admitted sheepishly.

“Oh, I’ve done some reading there myself,” Gary said with a smile. “Ever read anything by Ken Nitsua? Good stuff.”

“I don’t know,” Jeremy shrugged. “Maybe.”

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

“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 realized 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 realized 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 reveled 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 5″ 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 manhood. 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.

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3 thoughts on “Chat Room Exploration

  1. Rob says:

    A Great Loving and Tenderous Story. I’m eager to read more of their learning adventures! To read how Jeremy opens up to who he really is!

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