Jeremy makes a discovery

gay coming of age

A gay man introduces his younger brother to the ways of anal pleasure.

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Jeremy makes a discovery

There was a light tapping on the door and Michael opened it to find his 16-year-old brother Jeremy.

“Hey Jer! How you doing bro?”

The teenager standing there gave a long-suffering look.

“It’s Jeremy, I keep telling you that.”

“Oh yeah, I forgot,” Michael responded with a lopsided grin that made it clear that he hadn’t forgotten at all.

He’d been trying to get his younger brother to chill out and relax a little for years – since before he’d left home for college, but Jeremy was still painfully uptight. Although uptight was really not the best description. He was reserved. Kind of traditional. Mike put it down to the influence of their grandfather who had been the primary male influence in their lives since their father was lost to cancer ten years earlier.


They hugged.

“Whatever bro, I’m just happy to see you.”

Jeremy smiled.

“Happy to see you too Michael.”

Jeremy grinned to indicate that he knew he was deliberately using the version of Mike’s name he preferred not to use. Mike punched him lightly in the shoulder and grinned.

“Why don’t you leave your bag there and come say hi to Frank?”

Jeremy put his bag down, closed the door and followed his brother to the living room where Mike’s boyfriend was watching TV. Frank turned to see him enter then stood with a huge grin.

“Hey Jer!” He remembered the teenager’s preference for the long version of his name and awkwardly added “rremy” to the end.

Jeremy laughed.

Frank stood and approached with his arms wide. They embraced, and Frank hugged him even more warmly than his brother had.

“Great to have you here. It’s not much,” he said giving a dismissive wave at their small apartment, “but feel welcome. Our house is your house buddy.”

Jeremy returned the smile.

“Thanks Frank.”

Jeremy glanced at the TV.

“Duck Dynasty?!”

Frank grinned again.

“I know, redneck trash and they’re homophobic assholes but it’s a guilty pleasure. Maybe I just like the way he blows on the horn!”

It took a moment then Jeremy understood the double-entendre and he laughed.

Mike gestured to the settee.

“You’ll be sleeping on the couch. We bought it for when you come stay. It folds out into a bed. It should be comfortable.”

“Thanks Mike!”


For the next few days, Jeremy hung out with his brother and Frank. They took him to an ice-hockey game and a movie, and he went mountain biking along the local trails with Frank while Jeremy was at work. On the fourth day something happened that forever changed the youngster.


Jeremy was dressing after a shower, and he couldn’t find his top.

“Hey guys, have you seen my fleece?”

“Yeah, I washed it after we went biking,” Frank called from the small kitchen. “It was covered in mud.”

“Oh, thanks Frank, where is it?”

“It’s with the laundry, on our bed.”

“Okay thanks.”

Jeremy went into the bedroom and reached for his fleece from the pile of laundry. In the lounge, Mike was furiously gesturing to Frank but it was too late. As Jeremy turned to leave the bedroom, he saw the object that his brother had hoped he would not. It was a machine. The base was bolted to the floor and there was a piston sticking vertically out of it topped with a dildo. Jeremy was momentarily shocked. He’d always assumed that his brother and Frank fucked each other although he never gave it much thought, but this; this was a side of their relationship he’d never even contemplated.

He looked at it for a moment then walked out of the bedroom and shut the door without a word.

“Did you find it?” his brother asked.

Jeremy waved the fleece but he couldn’t hide the smirk on his face.

“You saw the other thing too?” Mike asked.

Jeremy nodded, his smirk broadening.

“Is it what it looks like?” he asked.

“What does it look like?”

“A dick on a pump.”

“Yup, that’s what it is.”

Jeremy’s smirk grew still further.

“What’s it for?”

“You stand over it,” his brother replied, leaving the rest unspoken.

“And it… it goes up and down?”

Frank was listening in. He walked in from the kitchen.

“Look Jeremy,” Frank said, “I’ll be honest, getting fucked feels really good, and being fucked while you get a blowjob feels even better. You had a blowjob yet?”

Jeremy shook his head.

“Anyway,” Frank continued, “We don’t want anyone else involved in our sex life so we bought that. It’s the best of both worlds.”

Jeremy was quiet for a moment. He knew his brother was down-to-Earth, and unashamed of his sexuality but this was a new level of information that Jeremy had never expected to receive.

“It feels good?”

“Oh yeah, definitely,” Frank confirmed.

He looked at Mike and raised his eyebrows.

“You can try it if you like,” Mike offered.

“What me? A blowjob? That would be too weird. Anyway, I’m not gay.”

Frank laughed.

“Nobody was offering you a blowjob Jeremy, nice try!”

Jeremy blushed. He felt like he’d be caught trying to GET a blowjob now.

“I was just suggesting that you might want to try the ramrod.”

“Is that what it’s called?”

“Nah, that’s just our name for it,” his brother said.

Jeremy grinned.

“Thanks, but I’m not gay.”

“That’s what everyone says until the first time they try it!”

“Nah, I’m only interested in girls.”

“So are you with a girl at the moment?” Frank asked. “Had sex yet?” He leered playfully and gave the boy a couple of nudges with his elbow.


“’No’ to what?”

Jeremy blushed.

“To both.”

“So how do you know you’re not gay?” Frank asked playfully.

Jeremy’s blush deepened.

“I’m just not. I only think of girls when I…”

He trailed off.

“When you what?”

“When he jacks off, isn’t that right you little hose monkey?” Mike said with a grin giving his brother a hard shove.

Jeremy looked bashfully at the ground, his blush at maximum intensity.


“Jeez bro, it’s nothing to be embarrassed about,” Mike said, “you think we don’t both still jack off?”

“Some more than others,” Frank added pointedly.

Mike grinned.

“Guess being horny runs in the family huh Jeremy?”

Jeremy looked up with a shy smile.

“I guess so.”

“Well I’m telling you bro, you’ve never cum until you’ve done it with a dildo in your ass. There’s nothing like it.”

“Yeah but I’m not…”

“Yeah, you’re not gay. You made that point. You don’t have to be. I know a couple of straight guys who let their girlfriends slip a finger up there during sex. They all love it. I’m telling you it’ll change your life.”

Jeremy thought about it for a few seconds.

“Nah, it’s not for me. I definitely wouldn’t like it.”

Mike wrapped him arm around his brother’s shoulder.

“Jer, you are SO uptight. It’s not good for you. Even now you’re probably irritated that I shortened your name. You’re gonna have a heart attack by the time you’re 40.”

“I’m not uptight,” Jeremy protested. “I can be chilled.”

“Oh really? Ever smoked pot?”

“No, but..”

“French kissed a girl?”


“Broken the law?”


“Sworn around mom?”


“Have you ever even stayed out past the time mom said you had to be home?”


“Dude, you’ve got to live a little. You’re in danger of being really boring. What girl is going to want a dude who never takes any risks. Do you do ANYTHING exciting or reckless?”

“I inline,” Jeremy offered, feeling increasingly dull.

“Aggressive or flat?”


“Well that’s something. There’s hope for you yet.”

Mike pulled his brother close and gave him a theatrically sloppy kiss on the cheek.

“You got to take some chances. Live a little bro.”

Jeremy thought in silence for a long time before he finally said, “Am I really boring?”

Mike gave him a sympathetic half smile. He ran his fingers through his brother’s 1960’s dad haircut.

“Yeah, kind of bro.”

“Okay, I’ll try it! Just to prove I can take chances, but there’s no way I’m gonna like it.”

Mike smiled.

“Sure, you won’t, but you have to give it a fair go.”

“What does that mean?”

“At least 15 minutes.”

“15 minutes? I don’t even ja… masturbate for that long. And what if I don’t like it?”

“Tell you what, if you give it 15 minutes and you don’t love it, I’ll give you a hundred dollars.”

“A hundred dollars?”


“Will it hurt?”

“No, of course not, not if we take it slow and make sure it’s adjusted right.”

“Okay, I’ll do it. On Sunday before I leave.”

“Why not now?”


“Sure, why not?”

“Um… I… err…”

Jeremy couldn’t come up with a good excuse.

“I guess. I wasn’t really…”

“When did you last jack off?”

“Umm, Friday night, before I came here.”

“Four days? Is that how often you usually go?”

“No, but I didn’t wanna get caught.”

“We’re not going to walk in on you in the shower.”

“I don’t do it in the shower.”

Mike looked at Frank and his boyfriend smiled.

“Ohhhh. You must be getting horny by now?”

Jeremy grinned sheepishly.

“Yeah, kinda.”

Frank laughed and Jeremy gave him a half look, his sheepish grin intensifying.

“I tell you what Jeremy, you may be a little… traditional but you’re adorable. The girls are gonna love you when start to put yourself out there a bit.”

Jeremy gave a happy little smile.

“Sooo cute!” Frank said. “In a Norman Rockwell kind of way.”


A minute later, they stood in the bedroom. Jeremy turned to Frank.

“Were you going to stay?”

“Sure. Unless you’re shy about your body?”

“Not my WHOLE body.”

“Ha, ha! I’m sure you have nothing to be shy about.”

Jeremy was uncomfortable about being seen nude by a stranger but it felt rude to protest when he was in their apartment. He and Mike had shared a bedroom for a few years and he was used to being seen naked, but not since puberty. But that discomfort was nothing compared to the thought of letting the ramrod fuck him. Still, $100 was a lot of money to him and he just could not afford to turn it down.

Jeremy started to undress. He stripped down to his skimpy sports briefs.

“Wow Jeremy, you sure got grew up,” Mike said looking at his slender body.

Jeremy was only five six tall – 1.67 metres, but he was covered with lean muscle.

“When did you get muscles?”

Jeremy shrugged.

“I told you, I skate, and I watch what I eat.”

“Looking good bro,” Mike said nodding and making an approving face.

Mike unrolled a condom onto the ramrod’s dildo. Jeremy frowned.

“Hygiene bro. Safety first, always, even with the toys.”

Jeremy felt strangely reassured by his brother’s remark.

“It looks really big. Is it even gonna go in?”

“8 inches long,” Frank said, “But the piston is adjustable. It doesn’t all go in you.”

“But it looks really thick.”

Frank looked at Mike and something passed between them.

“Not really. It’ll be fine. Start slow and we’ll use lots of lube. It’ll be fine. You’re gonna need to take those off though,” Mike said, nodding towards Jeremy’s briefs.

Jeremy turned away and pushed his briefs to the floor. He turned back with his hands covering his groin. Mike looked at him.



“You’re gonna stand there like that?”

Jeremy looked down at himself, then reluctantly lowered his hands to his sides. His brother glanced at him, seeing him naked for the first time since he’d passed puberty.

“Nice nuts,” he observed, looking at Jeremy’s large scrotum. It didn’t hang particularly low, and you couldn’t make out the individual testicles but it was about the size of a tennis ball.

His penis was more modestly sized, cut far back, with a button glans at the end. Above was a neat patch of hair, smaller and sparser than most of his peers.

“Here back up over the ram,” Mike told him, lowering the dildo.

He smeared the dildo with lube as his brother moved into place. When Jeremy stood over it, Mike lifted the ram, spreading his brother’s bottom cheeks with the other hand to allow unobstructed access to his hole.

“Back a touch more.”

Jeremy did as he was asked. Mike pressed the dildo against his hole and Jeremy instinctively tensed as he felt the cool lube touch him.

“You’ll have to relax for it to go in.”

“It’s cold.”

“Ha, ha! Oh yeah, that, you get used to it. It’ll warm up soon enough.”

Mike continued to press the dildo upwards slowly and his brother tried to relax despite the feeling of being invaded. Mike watched as the boy’s asshole lips slowly spread.

“It’s tight,” Jeremy noted.

“Yes, but no bigger than a hard crap. That’s why I’m going really slowly not to hurt you. Your asshole stretches but it takes a while. Try to relax.”

Jeremy heeded his advice, and Mike continued to press gently, content to take as long as he needed so as not to hurt his brother.

After five minutes Jeremy said, “What’s happening? Is it in yet?”

“You’ll know when it’s in. I’m taking it easy so I don’t hurt you. Almost there.”

Jeremy’s sphincter was stretched around the head of the dildo. The dildo had a stylised head; bulbous with a recess behind, and then ribbed along its length. The head slipped inside then his sphincter momentarily closed into the recess before opening again as the smooth dildo went deeper inside. Jeremy let out a little gasp as it passed into him.

“It’s in now,” Mike said.

“Yeah, I felt it.”

“I’m just gonna set it to the right height. Stand up straight with your feet apart.”

Jeremy did as he was told and his brother lifted the dildo. When it was three inches was inside, Jeremy gasped again.

“Touch something sensitive inside?” Mike asked grinning.

Jeremy nodded.

“That’s your prostate. The male Gspot. That’s what the ramrod is designed for.”

Mike lifted then lowered the ram a few times.

“Right there yes?”

“Nnng, yeah,” Jeremy said, surprised at the sensation.

A few dribbles of thin milky fluid fell from his flaccid penis. Frank noticed but said nothing.

Mike continued lifting the dildo until Jeremy tensed and rose to his tip toes.

“Unnn, that’s pressing against my insides. It’s hurting,” Jeremy protested.

Mike lowered it an inch and Jeremy came down from his tip toes.

“What about now?”

“Little bit further.”

Mike lowered it a little further until five inches was buried in his brother’s hole.

“Okay now?”

“Uh huh.”

Mike locked the piston arm off then joined Frank standing in front of Jeremy.

“Ready to start?”

“Yeah. It feels weird.”

“Yeah, but good right?”

“No, it’s just stretching my butthole.”

Mike smiled.

“Okay, we’ll start slow. 15 minutes no matter what, agreed?”


Jeremy looked apprehensive as his brother reached to the floor and picked up a remote control attached to the base by a wire. It comprised a single dial. He turned the dial to its lowest setting and the piston slowly started pumping the dildo in and out of his brother’s hole. Jeremy straightened, his eyes wide.

“You okay Jer?”

For once, Jeremy didn’t correct him.

“It’s got bumps on the sides. I didn’t realise.”

Mike grinned.

“You didn’t feel them as I put it in?”

Jeremy shook his head. He stood stiffly as the dildo slowly slid in and out of his hole, the head bumping past his prostate, but never coming close to withdrawing.

“What do you think?” Frank asked.

“Fees weird,” he said again. “That’s all. I knew I wasn’t gay.”

“No-one said you were.”

“I know. But now I know for sure.”

Mike smiled. He turned the dial to its second setting, then its third. The head moved faster, maintaining a steady rhythm. Jeremy looked down at his flaccid cock with satisfaction.

His brother turned the dial up to 4. Jeremy looked at his brother.

“It’s not going to work Mike. It’s not doing anything for me.”

“Who’s your best friend Jeremy?” Mike asked.

Jeremy frowned confused.

“Ashley Brookes, why?”

“Just imagine this is his cock in your asshole.”

Jeremy’s frown deepened.

“Dude, I don’t wanna do that!”

Mike grinned and turned the dial up to 5.

“This is the exact speed it feels like to get fucked,” he told his brother.

The dildo pumped Jeremy at a steady pace now. To his dismay, he felt blood filling his cock. It rose slowly, drooping in a 5-inch curve. He opened his mouth to say something, but he was distracted by the feeling of pleasure in his asshole, and he left whatever he was going to say unsaid. His mouth opened and closed as an expression of uncertainty painted itself on his face. He furrowed his brow.

“Well, well,” Frank said.

Mike left the piston on its setting for a minute and his brother’s penis remained at half mast, neither inflating fully, nor collapsing. He turned the dial up a notch. The piston now moved at the speed of a vigorous fuck. Jeremy’s penis immediately responded, raising all the way, and inflating to its full 6-inch length.

“Ah, uhhh,” Jeremy gasped, his pitch an octave higher than his speaking voice.

Mike looked at his brother’s penis. It was straight as a ruler and its low circumcision scar was over a quarter of the way down the shaft. Despite its ferocious hardness, it was much more slender than the dildo, and Mike understood now why his brother considered the dildo to be so thick.

“Hmmm, guess you’re not immune after all Jer,” Frank said smiling gently.

Jeremy grimaced, not at the contraction of his name, but at the fact that his dick was now standing so tall, and hard. It pointed up at an angle of over 45 degrees and it was stiff as the metal piston the dildo was attached to. He spread his fingers and pushed his hands palm-down by his sides as though trying to lift himself on parallel bars.

His expression changed. No longer was he confident of resisting the machine’s effects. A range of emotions played across his face; first uncertainty, then surprise, and now arousal. He gritted his teeth and drew his lips back, looking down at himself, disheartened that his body had succumbed.

After just a minute on number 7, Frank said, “Balls are getting tight. I think you’re gonna cum soon.”

“No way,” Jeremy grimaced.

No sooner had he finished his denial than a thick rope of cum launched from his dick, twisting in the air as if in slow motion. It was pursued by three more monumental spurts. Jeremy looked momentarily shocked; surprised that an orgasm could arrive without warning.

“Sorry, you were saying?” Frank said grinning.

Jeremy had nothing to say, he just looked from Frank to Mike and back again, dumbfounded.

“That’s five minutes,” his brother said.

After another three minutes, Jeremy started to squirm and fidget, shifting from foot to foot.

“Okay, I’ve had enough. You made your point. You win. You don’t need to leave it on any more.”

“What’s the matter Jer – feeling horny?”

Jeremy glowered at him without saying a word.


“Yes, very. Satisfied now?”

“We can tell. Your balls are even higher than before. You’re about to cum again aren’t you?”

“Not if I can help it. Not if you turn it off now. Come on Mike.”

“But you CAN’T help it can you? There’s nothing you can do is there?”

“No, I can’t. Come on Mike,” he wheedled. Don’t make me cum again.”

“Why not? You liked the first time didn’t you?”

Jeremy didn’t answer.

“Ahh that’s it. You don’t like the fact that you liked it. That’s it isn’t it?”

Jeremy continued to glower. The inside of his thighs started to tremble.

“Isn’t it?” Mike persisted.

“Yes, you’re right. It’s freaking me out to jizz from being butt-fucked okay?! You made your point.”

“Yeah, I did, but you agreed to…”

A pained expression appeared on Jeremy’s face and he started to cum again.

“Ahhhh,” he moaned, his voice cracking. “Oh fuuuck!”

He didn’t ejaculate as explosively as the first time, but he came for longer; almost 50 full seconds.

“Look, you can actually see his balls pulsing as he cums,” Frank observed.

He and Frank both looked closely at Jeremy’s scrotum and there was indeed a fluttering movement on the surface where each testicle hung.

Jeremy would have covered himself from their scrutiny but his head was flung back and his fists were clenched into claws as the second orgasm washed over his body for an impossibly long time.


When it was finally past, he was sheathed in sweat. His forehead was drenched, and his usually immaculate side-parted hart stuck to his brow in dark streaks. Droplets on his chest joined to form rivulets that rolled down his pale, lean torso.

“Oh my god!” he groaned. “Oh god.”

Mike grinned at him but Frank looked at the splashes of cum that spread in a cone on the wood floor in front of Jeremy.

“I think you came even more that time Jeremy. Well done!” he said as though congratulating the teenager on passing a minor test.

“Oh god!” Jeremy repeated, overwhelmed by the intensity of the orgasm.

Mike looked at his brother whose mouth was hanging open like a drooling idiot. Jeremy’s eyes were droopy, heavy lidded.

“Your face right now bro. I really ought to take a photo but I don’t wanna embarrass you.”

“Oh fuck,” was all Jeremy could manage as the machine continued drilling him unabated.

Mike looked at his watch.

“Four minutes left. I’m sure you can cum at least once more. Probably two. Let’s find out.”

“Oh shit,” Jeremy moaned, “no more. I can’t squirt again.”

“Sure, you can,” Mike assured him, turning the piston up to number 8.

The piston hammered into Jeremy’s asshole.

“No!” Jeremy screamed. “Stop!”

He rose onto tip toes, desperately trying to disimpale himself, but the dildo was buried too deeply. He took an experimental jump but he still could not clear it. It was reaming his virgin hole and there seemed to be nothing he could to prevent it. Then he spotted the cable connecting the remote. It was on the floor at his feet. He leaned forwards to grab it but before he could bend quarter of the way, the thudding dildo was pressing against him, preventing him from bending more.

He switched his weight onto one foot and lifted the opposite leg to 90 degrees like a dog pissing against a tree in the hope that it would give him more elevation. It didn’t. He sagged back onto the dildo. He repeated the action on the other side with no greater success.

“What ARE you doing bro?” Mike asked.

“Got… gotta stop it!”

Jeremy could feel a deep glow emanating from his prostate. He tried to shift his position to prevent the dildo from rubbing against it but his hole was too tight. He tried clenching his hole but the ram was too powerful and now he became aware of the pleasure in his sphincter as well.

And then he was ejaculating again. This time he didn’t lose his mind. There was a single violent squirt that rose to head height; over almost before it began. A minute later it was followed by a second staccato blast, then a minute after that, a third. At 13 minutes, cream oozed from the eye of his penis, as his balls were finally unable to launch any more cum into the air. It coated his glans in a white film.


He continued fidgeting, dancing in slow motion, shifting his weight in an effort to prevent the dildo from bumping past his prostate. He could feel his sap rising, rising, rising. Mike looked at his watch, ready to finally switch the ramrod off but Frank put a hand on his to stop him. Then he pointed to Jeremy’s nuts. They were so high it looked as though they wanted to crawl back into his belly.

There were just a few seconds left but Mike waited, allowing his brother to have one last, meteoric prostate orgasm. It began at a few seconds past the 15-minute mark and it was as powerful as the second, but without an ejaculation. Jeremy squirmed and groaned and begged and called out to a god he didn’t believe in, but Mike allowed the machine to keep pumping until his younger brother finally collapsed, exhausted and completely spent, a minute after his sixth brain scrambling orgasm. The machine was the only thing holding him upright now.

Mike turned the machine off, and Frank supported Jeremy’s weight whilst Mike withdrew the dildo from his brother’s hole. Jeremy’s legs were like rubber and freed from the dildo he slumped into Frank’s arms groaning.

Mike cleaned his brother’s hole with paper towel. He looked into the now gaping hole and grinned.

“Gonna be while before his asshole closes properly.”

“Yeah. Remember how bruised mine was the first time?”

“Yeah, you were sore for a week!”

Mike wiped the end of his brother’s dick clean and they lifted him onto their bed. Frank looked down at the reclining boy. His eyelids were fluttering, and his eyes rolled back. His mouth agape moved as though he was trying to say something.

“Can’t tell if he’s exhausted or still on another planet.”

“Bit of both I guess.“

He patted his brother’s bare rump then pulled the duvet over the boy’s reclining body. He turned and cleaned up the cum that was sprayed in a 3-foot arc on the floor.

“I know one thing though, now he knows that assholes aren’t just for shitting!”

One comment

    • caleb-
    • 4th March 2020 at 4:21 pm-
    • Reply

    fuck that’s hot, any chance of getting more hands free orgasms?

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