By DerekGuy
Note: This story series includes depictions of gay sex between men including teens, adult and teens, and even heterosexual sex. If that’s not your thing or if it is illegal for you to read this story, then stop. This story is completely made up and does not depict anything true.
Comments, suggestions, and helpful feedback are welcome. - DerekGuy17@gmail.com
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Leo liked this kid. He decided the kid was 21. He had picked him up in a bar and they carded at the door, but who knows for sure. He looked much younger. Much, much younger. Leo hadn’t gone after high school boys since he returned to the United States, but he was willing to roll the dice. He had always liked them before.
“Logan,” the boy had said when asked his name. They had talked briefly while Leo drank freely and Logan barely nursed his. Surfing, Leo’s passion, was the topic. The boy was wearing a tight Billabong t-shirt. Logan looked adorable in it, Leo thought. Brown hair with a bit too much product, and begged to played with. He was about 5’ 7”, skinny, but still had the beginnings of a decent body. Another sign he was surely younger. He had green eyes and trace of acne on his otherwise smooth cream-colored skin. It was March, so a tan in North America would be a sign of artificially enhancement. He reminded Leo so much of Dan, his childhood best friend. That was probably what caught his attention aside from the shirt. He was a little shorter and skinnier, but it has also been 16 years since Leo had laid eyes on Dan who was 17-years-old then.
“Here we are,” Leo whispered as he opened the door to his hotel room. It was a non-descript Hyatt in San Diego not far from the beach. Leo had seen his mother’s lawyer today and resolved the remaining issues of her estate. She had died two months earlier, but Leo’s disappearance for a while had made the settling of her will a challenge. He had only returned to the United States a few days before she died. He saw her once in the hospital. There was no funeral.
“Drink?” Leo asked rhetorically to the young man. Logan had confidentially plopped onto the king sized bed and kicked off his sneakers. Leo brought the Pringles from the mini-bar over. Leo stood 5’11” and looked amazing for his 36 years. He had bright brown eyes and longish blond hair. His skin still had the brown hue of nearly an entire life on the beach. His had a classic surfer’s body earned from a lifetime with a board. Leo had a bright smile, as he usually did when approaching another person, and radiated a heat, as he usually did when seeking sexual prey.
They chatted for a while. The boy was from the area and said he graduated High School two years ago. He fumbled over his current status, college, where he was living – but Leo had already accepted he was about to have his way with a teenager despite the front. The boy clearly was making independent adult choices and Leo had spent his life living free of both societal and legal expectations.
The boy revealed he was an only child. “Just you and your folks then?”, Leo wondered, more to make conversation than to care.
“Just me and my dad. Just the two of us. And you?”
Rather than answer, Leo kissed him. Logan smiled shyly, but leaned forward to receive him with his mouth apart. The teen’s skin was soft and his tongue was curious and searching. They shared saliva and lips for a while until Leo began to rub Logan’s leg. Logan didn’t impede him, so Leo reached higher until he was feeling the hard bulge. It felt healthy and eager. Logan’s hand than felt for Leo’s package. It wasn’t hard yet, but anyone could recognize its size.
Within a couple minutes, they had removed much of their clothing. Leo was rubbing Logan’s 6-incher while Logan was helping Leo approach his normal 8.5”. Then the boy dropped to his knees on the floor and took in the hard cock.
“Oh!” Leo muttered in surprise. Not for the blowjob, but how far Logan got the dick in his month on the first move. “Oh!” Leo gasped again. The boy knew what he was doing very well and was working him wonderfully.
“Where did you learn to suck so well?” Leo asked.
“My cubbin’ made me thuck m when I…” Logan didn’t stop his ministrations for a second. Tongue, balls, shaft, head…
Leo pushed the moppy head off, somewhat reluctantly. “What?”
“My cousin made me suck him when I was 12. I’ve done it ever since.” He smiled, a bit of saliva dripping out of the corner of his mouth.
“Really? How old was he?”
“He was 14 at the time. One day when he was visiting our house, we shared a room. Late at night, he pushed me down on the bed, pulled out his dick and told me to suck it.”
“Why’d you do it?” Leo was more interested in the story than he expected.
“I looked up to him. I’d do anything he asked. And, he was really good looking too. Anyway, turned out I liked it, so I kept doing it. Him. Anyone. After four years, I’ve gotten pretty good.”
That the boy was revealed to be 16 was only of slight attention to Leo. More was how similar the story was to his own. It was remarkable.
Leo put his hand on Logan’s head and pushed him back to resume the wonderful suck job. But even as the boy was so excellent, his own mind wandered. The boy’s age, looks, story. It sounded impossible, but this boy might be his nephew. Leo let his mind wander as his dick was pleasured. He thought of his own childhood.
***
Dan had been Leo’s next-door-neighbor since Leo was seven and Dan was six. Despite a year apart, they became inseparable from the first day they met. Leo wasn’t interested in Dan’s sister, Izzy, who was also 7. Girls were yucky. But Izzy was also boring – in personality, in face, in life. Dan was beautiful – full of energy and charm. Dan was always called “cute” from his baby pictures through high school. Leo didn’t develop into his own look until middle school when he suddenly became hot out of nowhere.
The boys shared almost everything. They were each other’s support in all avenues of life. Leo especially needed it. He struggled in 8th grade. His other friends were starting to date and all the talk was dances, parties, and girls. Leo loved the parties and could talk to many girls, but never cared for them. He had kept a secret from Dan and finally couldn’t hold it back any longer. One night sleeping at Dan’s house – Dan must have still been 12 because his bar mitzvah happened a weeks later – they had been wresting and goofing around when Leo started tickling him. Dan was still really small, while Leo had already hit a growth spurt. He easily pinned down his friend and tortured him with tickling.
“Stop! Please, <huh> <gasp> Stop!!” Dan was very ticklish and Leo abused that fact. Plus his mom had already yelled at them to keep it down. Because they lived next door to each other, if they misbehaved she’d quickly send Leo home at any time of night.
“Stop?” Leo moved his knees to pin down Dan’s arms and shoulders. His crotch was pushing near Dan’s thrashing head.
“Yes! <hee> I’ll do <ha ha> anything.”
The next few steps were obvious. Leo paused in the tickling and began to grind into Dan’s face. His dick had grown hard over the past few minutes and Dan’s offer had finished the job. Dan didn’t say anything and the extended cloth pushed against his nose and mouth.
“Suck me.” Leo stated more as a command than a request. Dan let the words hang in the air for a long time. Leo finally had to break the silence. “It’s all I’ve ever wanted. I just want you to do it. Not a girl. Not anyone. Just you….Please.”
Leo was dominant in their friendship and never used the word please. That was enough.
“You have to tell me what to do.”
The blowjob was awkward. Neither boy had any experience. In the end, Leo jacked off onto Dan’s chest. Dan had never cum himself, so he was somewhat surprised by the amount and consistency of the semen. Leo looked to reciprocate, but the 12-year-old wasn’t cumming and after five minutes of jacking him, they stopped.
Neither mentioned the night to each other. For months, their friendship seemed the same other than they didn’t have any sleepovers. But one day, Dan closed the door as Leo came in his room.
“I started to cum,” Dan stated with the utmost seriousness.
“What? When?” Leo was surprised by the unexpected announcement.
“Three days ago. I wanted to make sure it could happen multiple times before I told you.”
“And?”
“I have been doing it non-stop since then. But I am ready for you to pay me
back…”
Leo nearly bust with joy. Sucking his friend’s tiny dick was easy and a pleasure. Leo hadn’t sadly idly during the intervening months, but was hooking up with other classmates. And even an adult neighbor. He found there were a lot more people looking to share blowjobs with another guy than he guessed. An emerging 8th grader had no trouble.
The sex between them became constant. As they spent so much time together and it took less than two minutes to run from one of their rooms, through the gate, and to the other one’s room, they were able to exchange sex a few times a day.
Within a year, 9th grader Leo was fucking 8th grader Dan. When Dan turned 14, Leo and Dan tried swapping roles. But nearly all the time Leo was a top.
Dan began to date girls while Leo remained exclusive in seeking men. Dan’s sex life in High School was typical for guys of his age and their suburban neighborhood. Leo was a man whore. From school to fellow surfers down at the beach, he found numerous contemporaries that were gay, bi, or curious. The aura and attitude Leo gave off also revealed others who would seek out his cock. Two teachers in school hit on him and he followed through with one. Fucking his history teacher on his desk made the rest of the semester a breeze, but always got him hard when walked into that classroom.
Dan never wanted to hear anything about Leo’s sexual adventures. As far as their conversations revealed, Dan was the only guy Leo ever fucked. Leo was certainly the only guy Dan was with. Leo, on the hand, loved to hear about Dan’s sexual pursuits. The younger boy embellished a bit, but also made a rule: He’d only tell any details while his dick was in Leo’s mouth or ass. Dan didn’t have a wild set of stories and was a lousy liar. So it was only the mostly true tales that got him to be a top with Leo.
By Leo’s senior year, the boys had been together well over 5000 times in some form. They never seemed to get tired of it. But they also didn’t think about the future. Leo would graduate in a few weeks, head to Mexico for the summer, and then had a job offer in the area at a surf shop. Leo’s dad had died years ago and his mom was a bit off her nut. The house had belonged to Leo’s grandparents and insurance money had carried them this far, but there was no money for college and Leo’s mom was on a path towards probable institutionalization. Dan was certainly going to a private 4-year college.
Senior prom was coming and Leo had no date. Dan, who had a serious girlfriend also in the junior class, had been pressuring Leo to be like anyone else and enjoy prom. Leo had missed junior prom when his mom had gone into the hospital.
“Who am I going to prom with? Not you. So who?” Leo dismissed the whole idea of going to that “straight-fest”.
“My sister is going to be your date,” Dan announced. “Izzy hasn’t been asked by anyone, no surprise. So you’ll take her. Just promise you won’t take advantage of her!”
Leo scoffed, but the idea wasn’t crazy. He got along well-enough with Izzy. He was probably the only boy, other than her brother, who spoke to Isabelle. She was extraordinarily shy and disappeared into the background. She wasn’t particularly smart or talented. She wasn’t unattractive, but she wasn’t good looking. In most ways, Izzy was decidedly average. The girl was not only going to graduate High School a virgin, but having never been on a single date or gone to a single dance. Leo would be doing her a big favor.
“If you don’t go for yourself,” Dan added, “then go for me.” He did.
Prom was typical. Silly, boring, cliquey. Izzy looked all right - the prettiest he’d ever seen her. She even danced a couple times. Everyone knew it was a pity date. Leo was totally out as gay even if he had never had an official boyfriend. They laughed, drank a little of the spiked punch, and headed out. They drove to the beach where Leo was most comfortable. Izzy had shockingly brought a bottle of vodka and some orange juice. They made screwdrivers and watched the waves. Leo drank a lot of these fruity drinks. He was still a lightweight with alcohol never needing it to get into bed with someone or on the dance floor and always concerned about his surfer’s body.
It got hazy for Leo after that. He remembered sucking on her breasts and thinking that it was more fun to do than he imagined. She also was more stacked than he thought – although what he did know about girls. He also remembered being much drunker than he had been in a long time.
He remembered the moment of entering her. She had been begging him saying she couldn’t graduate a virgin. That had been her line the whole time. She couldn’t graduate without her first kiss. Couldn’t graduate without a boy touching her. Without her touching a boy.
It was hazy, but it was also so clear. He knew he had forgotten something, but the novelty of fucking a girl overrode any other thought. It was pleasant enough. Less pressure. Less effort in pushing in. But devoid of real pleasure. It was more mechanical. Even random bathroom sex with a strange man seemed more fulfilling than sex with Izzy. With any girl.
The next morning, Leo awoke in Dan’s room. He was naked except for his boxers. He had passed out there after brining Izzy home and even the miniscule walk home was too much him. Her parents didn’t seem to care. Their daughter had finally gone on a date. Even with their son’s gay best friend.
Dan kissed him awake around 11am. “So, Izzy said she had fun. Thank you! As long as you didn’t make her a woman, you are the best.”
Leo tried to smile and grunt an agreement. His head didn’t really hurt, but his soul ached.
Suddenly he felt Dan’s mouth around his cock. His friend’s lips were a cleansing tonic for the straight fuck of the previous evening. That Dan’s was likely licking up his own sister’s pussy juices was something Leo chose not to acknowledge.
The blowjob was slow and caring. One of the longest and most attentive that Dan had ever given. When he finally came, Dan swallowed his load, something he usually didn’t do.
They snuggled together for about 15 minutes before Dan started rubbing Leo’s dick and bringing it back to hardness. In reality, Leo was capable of several sex acts one after each other, but Dan wanted time to lay in his male lover’s arms. Dan sat up and removed his own clothing. Pushing the sheet aside, he positioned Leo prone on his back with his dick rising in the air like a flagpole. After rubbing some lube in, Dan lowered himself on Leo and began a slow up-and-down fuck.
“Just lie back and enjoy. I’ll do all the work,” Dan smiled. While this wouldn’t be their last time together, they knew Leo was headed for Mexico for his surfing summer in less than week. They wouldn’t have many opportunities. This was Dan’s gentle farewell to Leo.
Four weeks later, Leo picked up his shirt and sandals on the beach after another amazing day on the wives. Mexico had been fantastic – not quite as good as the surfing he had done in Australia, but July meant northern hemisphere. He pulled out his cell phone and found a text message. From Izzy. “I’m late”.
The rest of the summer blurred into images. Izzy’s many phone calls telling him that he had to come back, that she couldn’t go through the pregnancy without him. Dan’s angry and then angrier calls and texts about betrayal. Traumatized calls from Izzy’s parents and from Dan that he ignored. Calls from his mom’s brother and her lawyer that focused on her mom’s downward spiral and the need to put her in a home. Everyone wanted him to come home. Everyone wanted him to come back. He just kept surfing.
Leo changed beaches a few times. He told no one where he was going. He didn’t want to come home. He didn’t want to be a father. He didn’t want to have sex with a girl. He didn’t want to deal with it. Fucking guys on the beach. That’s what he liked. He had no reason to go home if Dan wasn’t speaking to him. He wasn’t going to.
Leo moved from surf spot to spot. He earned money giving surf lessons, tricking himself out a little, working in surf shots and restaurants. It was easy for a good-looking clever 18-year old American with few needs to find work, make friends, fund fucks, and move place to place.
His was in New Zealand when his son was born. “Griffin,” the message from Izzy. His uncle told him his mom was safe in the institution and that the house had been sold, his stuff boxed up and put in storage. Dan left him messages every week telling him he hated him for raping his sister and betraying him. Dan started saying that he never liked sex with guys and Leo was a freak and he hoped he had AIDS. The messages got worse with every passing week.
Leo moved place to place spending his year surfing and having sex. His only connection to home was the cell phone, which his uncle continued to pay for. He never called home for anything nor told anyone where he was. Lying on the beach with three naked fourteen-year-olds, he felt at peace and completely removed from the mess he left behind. He looked at his cell phone. A message from Izzy. She texted every few weeks. “Dan had a son today. Nick. He needs you. So does your son.” Leo’s son Griffin was 2 when Nick was born.
A few days later, Dan left a drunken voicemail. He cried a lot and said how much he loved Leo, how much he despised him, and what Leo did to his sister was pure evil. He hoped Leo would die so he could be at peace. Then, he cried again and said he loved him and missed him. Leo smashed his cell phone under a rock. He had no way to be contacted by anyone back home. He was 20-years-old.
In the non-descript Hyatt, Leo came hard into Logan’s mouth. Despite the 8 ½ inches of cock already in his mouth, the 16-year-old casually swallowed his flowing cum. The boy pulled off and began to lick the semi-hard member clean.
Leo looked at the boy with the darting tongue. Same eyes as Dan. Sam color hair. Almost the same height. He glanced down and saw the same uncircumcised cock that he knew so well. Was this Nick? The hair was styled very differently. The voice a little deeper, more like Leo’s. The boy had a pierced ear. The skin was a little darker. But a father and son aren’t exact. And he didn’t know anything about the boy’s mother. The boy had said he was being raised by single father in the area. The boy liked surfing too.
***
As he stared at his former best friend and lover’s near doppelganger, he wondered if he had just been sucked off by his nephew. Wait, was it his nephew?
Leo thought about himself. He had an uncle – his mom’s brother. But Leo had no siblings. Leo never married Izzy. He wasn’t related to Izzy in any way. So he wasn’t related to Dan either. This Logan – or Nick – or whatever his name – would be the nephew of his “baby momma,” of Izzy. But he didn’t think they were technically related.
He put his mouth onto Logan’s dick. He wasn’t artful, but utilitarian. He was so distracted by the boy’s possible identity. Just make the boy cum. Logan started talking a little bit while he sucked.
“Nice. Harder. You know…I took up surfing because my…Harder…cousin surfs. His father is a world champion. I think. I never met him. Slower. But he travels around the world surfing. I guess it is always summer somewhere. Harder, please. Ugh. So both of us surf, but I’m better than my cousin.”
Leo shook his head. The boy knew. He knew all along. He was totally tossing out facts just to make sure Leo knew who he was. But how had he found him? It couldn’t be a coincidence. Leo found himself being turned on and started to suck his almost nephew with more intensity.
***
Four months ago, Leo had received an odd message. He had been living in Samoa of late and working in a surf shop. One day the owner showed him an envelope. It was from the US and was to be delivered to a particular young man about 5’11”, trim, avid surfer, blond hair, brown eyes, mole on left shoulder, American born. “This is a description of you, Chad,” the owner mused using Leo’s pseudonym of that past 16 years. Leo saw his birth name for the first time in years written on the envelope. The return address was a lawyer’s office.
They had been searching the world for him on behalf of his mom. Similar envelopes had been sent to the largest surf shop in every major surfing locale in the world. His mom’s lawyer didn’t talk about, or perhaps even know about, his bastard abandoned son. His uncle and aunt had both died childless leaving much of their money to his mother for her well-being. She was now near death and had, in a moment of lucidity, asked to see her son before she died. The envelope contained instructions were given on how to acquire a pre-paid ticket back to the US from anywhere in the world.
After three days of debate, “Chad” made the phone call. Two days later, Leo arrived and went to see his mom. The visit had been brief. She had not been lucid that day, or in many weeks since the letter was written. Leo talked to the lawyer afterwards to sign some papers. He was the next of kin and would inherit whatever money was left from his uncle’s estate.
Leo didn’t try to find anything out about Dan or Izzy or baby Griffin, who would now be a teenager. He prepared to keep a low profile while he waited for his mother’s passing. She died just a day later. The hospice nurse claimed she knew her son had returned and was at peace.
With no family capable of mourning, Leo had her body donated to science. The lawyer pressed on the need to resolve will, but Leo was too overwhelmed by it all and disappeared for a while. Now they had finally resolved the details and the money Leo inherited would allow him to continue to surf for the rest of his life without a struggle.
***
Logan grunted bringing Leo back in the reality of the moment. He had the very sweet cock of a beautiful 16-year-old in his mouth and that deserved his attention. Logan came with force and with some loud grunts. Leo didn’t suck others to orgasm much, but he never had a problem taking it all in when did so.
The boy continued talking, but Leo simply told Logan, “Nick, turn over.”
Without comment, Logan did so, confirming Leo’s suspicions. He didn’t know what the boy wanted, but he had already ruined this family homecoming as usual. He figured might as well get the maximum pleasure and fuck his sort-of nephew and relive his time with Dan through Dan’s son.
Logan, for all his bravado and demonstrated sexual experience, had trouble taking in the large, hard cock Leo pushed into his anus. They boy wasn’t a screamer, but he did make very loud grunts that in a nicer hotel might get a call from the front desk.
While it wasn’t torture, Leo decided to use the physical stress on the boy to get some answers.
“You’re Nick, aren’t you?” Logan pushed hard causing Logan to increase his moans. Leo thrust deeper and repeated the question.
“Unh. Unh. Yes.” Logan’s voice dropped into a whisper.
“How did you find me?”
“By accident.”
“What do you mean?” Each time he grew frustrated, Leo had increased the pace. The boy had stopped responding, so he slowed down. No need to hurt the teenager.
“Saw you at the lawyer’s office. I recognized you.”
“Why were you at the lawyer’s office?”
“You mom left money to…my cousin. He wouldn’t come, so I came for him.”
Leo hadn’t read the will or the other papers. He just signed what was in front of him to get rid of the whole situation. Something didn’t make sense. A 16-year-old at a lawyer’s instead of his cousin…
“How is Dan?” No answer. “Your dad.”
“He’s fine. Got married. Works in sales.”
“You said you had a single father?”
“Yeah. Ow! Oh…. I wanted you to figure out who I am, so I said that.”
“And Izzy?”
“She’s also married. 3 more kids. He’s a jackass.”
“Her husband?”
“Yeah.”
“And…and…” Leo faltered.
“Griffin?” Logan said without emotion. Leo was quiet and clear.
“Yes.” Leo began to fuck with rhythm. It was like jacking off with a 16-year-old’s ass. As soon as Logan/Nick said Griffin, it made Leo incredibly hard.
“Your son is okay. He does surf. He’s pretty good. But he moved away after High School. He doesn’t get along with…his step-dad.”
“Where does he live?”
“Another part of San Diego. He’s talented. Smart. He’s gay. He looks like his mom’s side of the family. I think you’d like Griffin.”
As he said the name of his son again, Leo felt his body coarse with fire. He slammed his torso against the pink hairless cheeks of the boy. The semen started pushing out into the boy’s body. Like that night with Izzy, he had neglected to use a condom.
“Oh!” the teenager shouted in delight. “Leo, you should know…”
The 36-year-old continued to expel cum taking away his focus from the teenager’s words.
The teen spoke with clarity despite the situation around him. “Leo, I lied. I am not your nephew.”
Leo’s ecstasy made it hard for him to comprehend exactly what was being said.
The teen looked over his shoulder just as Leo finished his orgasm. “I’m Griffin. I’m your son.”
Leo lay on the bed bathed in sweat and body fluids. Griffin had recovered remarkably quickly.
Griffin dressed as he spoke. “The story I told was true. Griffin did force himself on Nick when they were 14 and 12. I was trying to copy what you did to Uncle Dan. But it didn’t take. Nick wasn’t into sex with boys. But I was. I am. Just like you.”
Leo was reticent to say anything, but had a question he wanted to ask. Griffin anticipated it.
“Izzy. My mom told me all about it. About you and Dan. She didn’t mean to. I read it in her journal. She wrote a lot when she was a teen and I found her journals one day. She wrote a lot about Dan, and you. She always loved you, but never said a word. And she wrote about pro `m.”
Griffin was dressed and was tying his shows. “I knew you had run away from her and from me. But I wasn’t angry. I just wanted to meet you. It really was a coincidence running into at the lawyer. One of secretaries pointed you out thinking we were there together as father and son. Your mom’s will specified that I got a small inheritance.”
Leo was sitting on the edge of the bed. His mother has known about Griffin despite her condition. Griffin was awkwardly standing, inching towards the door. “So after I saw you at the office, I came up with this plan to meet you. I sort of followed you back to the hotel and then staked out the lobby. Then I followed you to the bar.”
“Why pretend to by your cousin?” Leo’s voice was totally calm.
“I don’t know. I wanted to punish you. But I wanted to tell you everything. And I wanted you. I wasn’t thinking clearly.”
Leo was about to speak again. Griffin waved his hand in dismissal. “I’m going to go. I wrote my number down on the pad by the bed. If you ever want to talk or…whatever. No expectations or guilt. No revealing things to my mom or Uncle Dan. We can create whatever connection you want. And I hope we will.”
Griffin walked up to Leo with a strong open-mouth kiss. Leo kept his lips closed as every emotion went to war. But he did otherwise kiss back.
The 18-year-old son he never thought he’d meet and certainly never imagined he’d fuck, turned and walked out the hotel room door. Just for a moment, Leo began to cry. Then he got dressed and headed for a middle of the night walk on the beach.