First time author here, this story is going to be bisexual but is going to start out pretty gay. Feel free to email me with any feeback or comments. No editor here so please give any typos the benefit of the doubt. Whole story is fictional, and any characters with names similar to real people are deliberately written to be not like those people, even the opposite sometimes. Hope you enjoy.
Man it was going to be a long summer. Tyler was just starting his first week as a summer intern at a fortune 300 company's software development department. There was a global pandemic going on so he was working remotely. No hip office with a built-in cafeteria and bar in downtown Chicago like he was looking forward to ever since he got the offer in January. He had to cancel his lease to the nice rooftop apartment he was subleasing for the summer. The apartment was next to a huge block of bars and he was really looking forward to hitting a new dating scene after this past semester. Going into his senior year he already swam through the dating pool at his small private college. He still had a fun semester with all his friends and the parties at his fraternity, but he had just been rotating through the same 4 fuck buddies until things went south. They all wanted to be more than just fuck buddies, but he didn't want to date any of them. While they were all stunning and Michelle was extra kinky, he didn't feel a connection with them the way he did his Sophomore year ex. He had thought he would marry Marissa, so she devastated him when she broke up with him and to transfer to a university across the country. She got into a guaranteed getting the big bucks at a hedge fund elite kind of finance program. Tyler completely understood it was a life changing opportunity, but when she said she didn't want to do long distance, and said that they "weren't off the table for forever, but she needed time to grow by herself", Tyler didn't even want to talk to her anymore he was so devastated. After that he had proceeded to fuck his way through the first half of his junior year.
He was a tall good looking guy so he had no trouble getting girls to come home with him from the bar. 6'4 220 of muscle he had kept up since playing basketball and football in highschool, dark brown hair, blue eyes, and a reputation for his thick 8.5" dick had girls coming up to him all the time. He enjoyed a comfortable position as community dick as he fucked away his sorrows through the first semster of his Junior year. Until he learned a valuable lesson about condoms when he got the clap before finals and decided to be more selective about who he went home with during the next semester. By March all four of his regular fuck buddies wanted commitment, and cut him off. So he already wasn't getting laid when the pandemic shut down the whole university. His last remaining fuck buddy, Michelle, even had the audacity to ask him "what are we" while he had her completely tied up with nipple clamps on! When he responded that he thought they were just fun friends, she had gotten upset and demanded he unclamp and untie her. She stormed out and left him feeling guilty and horny. He did his best to not lead any of them on, but he ended up feeling awful about rejecting each of them. He just wasn't ready again for anything serious.
When the pandemic started, he moved back home with his parents to finish up the semester online. That's when his remote hell began. His idiot older sister snuck out and nearly right away caught the plague quarantining the whole family. Luckily no one was hospitalized and everyone survived. Everyone didn't get it all at the same time though so the family was pretty much shut off to the outside world till the end of the semester. So Tyler had done something he hadn't done since he was 17: go eight weeks without sex. By the last week of the lock down he was jerking off 5 or 6 times a day and losing his mind.
His dad was a Lawyer and made pretty good money, so their family had a condo at a resort down in Florida. The place was on the beach and had several pools and bars. He thought it would be the perfect place to work remote from and would thankfully get him some space from his family. He drove down the day before he started his internship expecting it was going to be a cake walk. He had done a lot of actual work at his old internship, but he heard the pay was very good and the work minimal at this company. His first day started off pretty normally with an orientation session on Zoom, apparently that was the video conferencing software for this company. After the orientation though he had a meeting with the Senior Director he was going to be working under this summer. He connected to the call and saw a stunning blonde waiting for him. She was in her early 30s, very young for her position, had blue eyes and wore her hair up in a ponytail. She was sitting in a well decorated office and wearing a conversative top that failed to hide a very large pair of tits. She was stern faced and immediately said, "Tyler Woodcock?" as he joined.
"That's me". Tyler said, giving her his best smile. Easy job and a total babe for a boss, this could be a great summer. Most people would crack jokes at his last name or at least have a little gleam in their eyes as they said it, but she was completely neutral.
"Well Tyler", she went on. "We are unfortunately incredibly understaffed this summer. I'm not sure why we haven't completely scrapped the internship program, but HR is insisting we go through with it. I don't have time to babysit the usual inconsequential internship project I would have you do. So you're going to be a real developer this summer." Tyler's stomach dropped. Uh oh this didn't sound like a cake walk anymore. Tyler had the experience from his previous job, but he wasn't sure how much use he was going to be without knowing anything about their code base, but he figured he could give it a try.
"The good news though is if you can keep up I can guarantee you a role here after you graduate on the fast track to a Senior role" she said. Tyler perked up at that. He looked up salaries when he applied and Seniors made about as much as his dad did when you included all the benefits and stock you got with it. Big tech could pay well.
"I'll give it my best Ms. Bryant", he said. He expected her to wave away the "Ms" and ask her to call him Samantha, but she just nodded at him. Another person connected to the call and a new less beautiful face joined the call. A nerdy man in his 20s was introduced to him as Jeremy, one of the Senior engineers on his new team. He was going to start off right away shadowing him.
And just as quick as that Ms. Bryant left the call and Jeremey grimaced and said, "Welcome, things are kind of always on fire here right now, but things should chill out next quarter". The rest of the week was filled with cramming sessions all about the applications his new team was in charge of and what they were expected to build by the end of the quarter. Tyler wasn't an expert but it sounded like a lot more work than he would think possible to get done by the end of May. He didn't make it to the beach once during the week, he was usually on calls or shadowing someone working from the morning to well into the night each day.
The resort his family's condo was in was mostly rentals, but the local government still hadn't opened up rentals to tourists yet, so the place was an absolute ghost town. The pools and the pool bars were closed, so he wasn't missing out on much while he was working, but it was still frustrating to not get to enjoy the beautiful weather. He took most of his calls that he didn't need his camera for out on the condo balcony sunning in just his underwear. The unit was on the top floor of the condo complex, and they didn't have any neighbors, though his Dad did mention someone bought one the units next to theirs. So Tyler regularly walked around in the nude since he had the place to himself. He took calls on their balcony when he could, and he cooked for himself each night, but was usually still stuck in his perpetual zoom hell. It wasn't actually hell, he enjoyed the work and he felt like he was picking up things even if it was total information overload. He had enough experience from school and his past internship he felt like he could contribute pretty soon. He was finally starting to resign himself to the fact that it wasn't going to be the relaxing summer he was planning for.
<------>
His one solace from work was his gym time each morning before his first call. The first two days it was just him there in the very well equipped resort gym complete with sauna. Then on Wednesday there was someone in the squat rack when he walked in. They were doing sumo deadlifts and Tyler caught himself admiring their well rounded ass filling out their sweat pants as they set up. His dick started to grow and he realized it'd been far too long since he'd been around anyone besides his family. His bubble butted new friend started their first rep and to his surprise the ass he had been staring at was on a man. His dick didn't deflate at the revelation which surprised him. Tyler had jerked off with a friend one time when he was in high school, but that was the extent of his experience with men. They were both drunk and super horny after they both made out with their dates that night for hours, but didn't get past first base. He couldn't remember the last time he was this horny, probably that time they jerked, and he couldn't deny he liked what he saw. He took a moment and collected himself after he realized he had been staring, and went about his work out. When the other man noticed him he gave a wave, and walked over to introduce himself. Seemed like the normal thing to do for the only other human he'd seen besides the security guard, he hadn't seen any of the resort staff because he'd been working during the day. He ended up being another college student about his age. He looked like a good looking clean cut preppy guy like himself under his mask, shorter than him at probably 5'10" and pretty lean beside that thick ass of his. He introduced himself as Jack Struther, Tyler recognized the name as one of the families that had a place a few floors below theirs. There were so few units that were owned and not rented out that his parents knew all their neighbors. He said he was also down here for a week to get space from his family. Tyler introduced himself as Tyler Woodcock, and said that he already had and survived the plague so there was no need to wear a mask around him. Jack took off his mask revealing a handsome clean shaven face that paired well with light brown hair and green eyes and said, "Oh Woodcock huh" and glanced down at Tyler's still slightly bulging crotch.
Tyler just owned it and smiled and said, "Yup that's my name". Jack kept grinning and Tyler thought he might have seen Jack's sweatpants start to tent out to the right. Maintaining eye contact, Tyler suggested that maybe they grab a beer later as he hadn't talked to anyone outside his family in months. Jack readily agreed and they swapped numbers. Tyler wasn't completely sure but he thought there might be some weird tension going on. As he went back to his workout he glanced back at Jack's crotch one more time and was nearly certain he saw a bit of a tent. Tyler finished his work out and began another grueling day tied to his laptop. Around 8pm he got a text from Jack asking if he wanted to get a hot tub beer. Tyler was just finishing up work and dinner and readily agreed. He got down to the hot tub and Jack was waiting for him with a cooler and offered him a beer. When he got up out of the hot tub to grab Tyler a beer he couldn't help but glance at Jack's short swim trunks which he was filling out admirably in the back. Glancing at the rest of him he noticed he was completely hairless. "You shave man?", he asked?
Jack groaned as he sat back down in the hot tub and handed Tyler his beer. "Yea I'm actually on the swim team at my University. It's just D2, but we take it pretty seriously."
"Oh that makes sense, you have the build for it."
"Thanks", Jack said grinning. "I better with all the hours I spend in the pool."
"And is Sumo Deadlifting a normal part of a swimmer's training regimen?"
"No", Jack laughed. "My ex was just obsessed with my ass for some reason so I always make sure to grow it. You know what they say: "Glutes get the sloots".
Tyler had not heard that before and that got a genuine chuckle out of him. "Maybe I need to focus on those a bit more", he said.
" I'm sure you don't have a hard time pulling chicks, big guy like yourself."
Is this getting flirty?
Tyler blushed at the compliment a bit and thanked him. This tension felt weird with a guy, but he had been too busy to jerk off all day so he was even hornier than he was in the morning. "I do alright with the ladies," he admitted. "Though it's been rough since this whole pandemic started. Haven't seen a woman outside of my family since March."
"Tell me about it", Jack groaned. "I think I'm going to beat my dick off. Had this hot scary goth girl back at school. We aren't dating exclusively yet but she was crazy kinky in bed, just like my ex. She sends me snapchats all the time. Has me this close to driving across the country to see her", he said, holding his hand up and bringing his pointer finger almost to touch his thumb.
"Ah I'm jealous"
"What? You don't have any girls snapping you?"
"No I kind of broke things off with all them right before everything shut down"
"All of them? Are you telling me you went from multiple to none? That sucks dude, you must be going crazy."
Tyler grabbed a second beer out of the cooler and settled into the hot tub starting to feel pleasantly light headed. He proceeded to tell Jack all about his mismanagement of his fuck buddies, his dick perking up as he recounted how kinky some of them were. Jack quietly listened with an intentness that Tyler recognized as horniness. Jack then started to share details about his goth friend. She apparently was a year older than him and taller than him with heels. He sheepishly admitted that absolutely did it for him.
Oh so we have a sub here now do we?
Tyler was actually a bit of a dom, and as Jack finished his story he was completely hard under the water of the hot tub. He noticed Jack was keeping one of his hands around his dick too. Tyler was thinking more about Jack being submissive to this girl than he was her dominating him, though the nipple piercings did sound fun. By now they were both on their 3rd beer and the air was pretty tense. Tyler was thinking about the time he and his friend jerked off together when he heard a voice, "Hey mind if I join you boys."
A large older man approached them. Tyler and Jack reached for their masks and he waved them off. "There's zero reported cases in the county. Unless you boys have been to New York this week, I don't think we need to bother with those yet." He settled down in the hot tub and introduced himself as Mr. Smith. Tyler recognized the name of the HOA president from his parents. He didn't do a whole lot since most of the units were owned by rental companies, but he lived at the resort full time. With his presence the sexual tension evaporated from the hot tub. Mr. Smith started talking about how all the sports leagues were impacted and all their plans to come back using a bubble and they were quickly talking sports as a group. Tyler ended up on what he thought was his 6th beer and was filling awfully tipsy. He realized he had another full day of work ahead, and excused himself for bed after finishing one last beer and complaining about his job. Though Mr Smith pointed out it sounded like he actually liked all the technical stuff because half of what he was saying made no sense to the retired banker. Glancing one last time at Jack's hairless muscled body he wobbly went to his unit. Where he passed out as soon as his head hit the pillow.
Tyler woke up with a bit more of a hangover than he anticipated that Thursday morning. He still had a while before work, but he didn't think he was up to working out. He laid still for a while before deciding that maybe getting in the sauna would be proactive for this hangover. It took him another 20 minutes to get the willpower together to get out of bed. He grabbed a gatorade and shuffled his way down to the gym to find it empty. He changed in the locker room and entered the sauna in just a tiny towel. After a few minutes he finished the Gatorade and started to bounce back from his hangover in the way that all 21 year olds take for granted. Once the pain was gone he was then aware of how god damn horny he was. He didn't jerk off before bed, and Jack's flirty smile and hairless legs had him worked up last night. What the hell, it really had been a while since he'd been with a woman. He started to get a tent in his towel as he thought about how that bubble butt must be hairless like the rest of him. He started to idly stroke his cock in the sauna feeling a little weird about thinking about a guy like this, but he really was too horny to care. Suddenly the door to the sauna opened and Jack walked right in. He took a moment to notice Tyler, and Tyler quickly covered himself the best he could.
"Oh what's up man. Feeling the hangover too?" he said when noticed Tyler.
"Yea man", Tyler laughed a little flustered. Jack looked down and probably couldn't miss Tyler's bulge through the small towel. He paused for a second then sat down. The sauna wasn't that larged, it could fit 3 people but really only 2 people spread out, which of course everyone does in a sauna. Jack's leg was only about a foot from Tyler's. They soaked in the sauna and let the tension settle. Tyler couldn't help but keep glancing over at Jack's muscular slim body, his well defined core and muscles started to really stick out with the gleam of sweat. He stayed hard under his towel. He could swear Jack was also glancing at his larger, more muscular frame, and after about a minute began to notice him forming a sizable tent of his own. This was driving Tyler crazy. He really should have jerked off last night before bed.
Jack broke the silence with a "Dude." and looked over at Tyler making tense eye contact with a casual smile. "I bet it would feel awesome to jerk off in here all light headed."
Tyler slightly unsettled said, "I was actually uh jerking off before you came in."
"Holy shit for real? Well... you shouldn't stop on my account" Jack said huskily, and started to rub himself through his towel.
That was enough for Tyler and he started to stroke his near painfully hard cock. Breathing heavily he started to jerk off under the towel. All his girlfriends always talked about how he had a big dick, thankfully because a small dick would look like a micro penis on his tall frame, but he was getting a little dick shy here. Probably because Jack was a guy, but looking at the hungry look in his eye he got confirmation he wanted to see it. Tyler started to feel his normal confidence in bed wash over him and dropped the towel. Jack grunted slightly and dropped his towel too, revealing a long slightly curving cock. It was a little longer than Tylers's so probably 9" but not as thick. Tyler couldn't take his eyes off it and out of the corner of his vision he could see Jack staring at him stroking his cock too.
Fuck.
Tyler started to look at the rest of Jack's hairless body glancing at his ass pressed into the sauna bench. As they continued to stroke their legs started to drift closer together and until finally they both touched. It was electric, both of them putting pressure on the other. They stroked in silence for a bit longer neither cumming quickly, probably from their hangovers.
Jack huskily goes, "Uh so have you ever done anything with a guy"
Oh we're past flirting here
"Yea actually. We were really drunk one time in high school and me and a friend jerked each other off."
"Oh shit did it feel good? I haven't ever before"
"Yea man it felt a little weird but was really hot"
"Shit man, want to give it a try?" Jack said, not making eye contact with Tyler anymore looking down at his dick while he stroked his own.
Tyler for an answer scooted over to Jack so their hips were touching and reached out and grabbed his dick. The body contact was electric and Jack started moaning instantly as Tyler gripped him, a little precum coming out of his tip. Tyler's dick was rock hard as he stroked Jack feeling the smaller Jack pressed up against him. Jack hesitantly reached for his dick and Tyler gasped as Jack began to stroke him. They both started stroking each other softly but soon hit a faster pace. They leaned into each other more and more as they stroked. Tyler watched himself stroke Jack mesmerized by his dick and strong hairless legs. Their heads started touching and Tyler was thinking about kissing Jack's neck when he heard him start to grunt. Tyler felt his dick twitch as Jack sprayed cum all over his own well defined chest and stomach. Turned on by Jack's orgasm Tyler felt his coming too and started to moan with him. When he came Jack angled it and it covered both of them in cum.
Tyler pulled Jack closer to him as he panted. He grabbed his hip and some of his ass as he did and they both sat there for a minute heads swimming from the heat of the sauna. A little bit of post nut clarity washed over Tyler, but he was still a bit horny and it felt nice so he didn't care. After a minute Jack muttered something about cleaning up and stood up. Putting his juicy ass right in Tyler's face. Tyler was definitely still horny as he watched Jack wipe the cum from his chest and walk into the locker room. He lay there in post orgasmic bliss until Jack came back with towels. His dick swayed in front of him as he tossed Tyler a towel. "Fuck I needed that" he said.
"Right?", said Tyler. He sighed as toweled himself out and stepped out of the sauna for a moment to clear his head. Checking his phone he looked at the time and realized he had a meeting starting in 5 minutes. He quickly explained he had to go to Jack and then quickly dressed and raced back to his condo, secretly thankful he had an easy out from that situation.. He was a little confused after the time in high school, but this time it just seemed pretty clear he was horny and needed to get off. Would have never happened if there were girls here for Jack and him to chase together.
Ms. Bryant sent him a message commenting on his late arrival via Slack, the company messenger app. Jesus this woman is hardcore. He apologized and said he got stuck in a conversation with his neighbor. Another busy day went by, he actually started writing some of his first code for the company adding a feature to one of the less important internal applications. Apparently his team was responsible for several internal applications that only had 3-4 users, so he was able to do necessary updates on less complicated things without it being a major risk having the intern work on it. That night he didn't hear from Jack, and felt a bit weird about doing all that with another guy. He was still so horny though, and he caught himself thinking about Jack's hairless body and round ass while he jerked off before bed.
Friday morning Tyler woke up horny again ready for the weekend, getting off with Jack helped but it still had been too long. He was going to try downloading one of those dating apps when he got off work. Find a local girl he could use his pool to entice over. When he got to the gym he saw Jack lifting again, this time doing upper body. Tyler said hello and commented that their split was reversed as he started lifting legs. There was that tension again for a little bit, but pretty soon things were chill while they worked out. Tyler couldn't help glancing over at Jack as he worked out. Jack was working out in shorts today, showing off his well muscled hairless legs and ass. He had one of the instagram influencers bubble butts even if he was a guy.
Man I really want to grab that ass.
Tyler began to tent up again as he went about his work out, with the squats deflating his dick, only for it to swell back up between sets. He finished early and had some time to spare before his first meeting and was pretty horned up watching Jack who started lifting shirtless half way through their workout. Feeling confident he walked over to Jack with a bit of a tent in his shorts which made Jack grin. "I think I'm going to get in the shower in the locker room showers." he said. "They're unnecessarily nice. You tried them out yet?"
"No I don't think I have." replied Jack with a knowingly look. "I'll check them out when I finish another 2 sets."
Tyler nodded at him and made his way to the shower. The showers were incredibly nice, but communal with 3 shower heads in a very nice tiled room. Tyler began washing off from his work out and stroking his dick. A few minutes later he heard someone come into the locker room. After a minute Jack came into the shower too. Tyler turned to see him come in half hard. Jack looked down at Tyler's hard dick and Tyler started stroking his dick. Jack followed suit and was soon just as hard. "Need a hand?" Tyler said.
"Yea man, still really fucking horny" Jack replied walking over to him. Tyler reached out and started to stroke his dick as he walked up and they stood there jerking each other. They started to pull in closer again as they jerked and Tyler loved the way he loomed over his smaller friend. He could tell Jack was into it too when he started to reach up and grab his back the way most girls do with his free hand to steady himself while they jerked. As Jack jerked him and pulled him closer Tyler's mind just completely blanked he was so horny. He leaned down and kissed him without thinking. Jack responded hesitant at first but soon they stopped jerking each other and pulled each other into an embrace. They kissed passionately while their dicks pressed between the two of them. Tyler saw an opportunity and reached down and grabbed Jack's ass hoping for a positive response. Jack moaned into his mouth and Tyler felt his dick twitch pressed between their hard stomachs. Taking the encouragement Tyler pawed at his ass, squeezing it and letting it drop satisfyingly. It was mostly hard muscle but still plump and round he broke the kiss to lean over Jack's shoulder and stare at his ass while he played with it. Jack nuzzled his face in the chest of the taller man. Tyler's dick felt great as it pressed into Jack's long dick and hard stomach.
Tyler decided to push things further and pulled back his hand and gave Jack's ass a firm smack. The smack echoed through the shower and he felt Jack tense. He looked down and saw the familiar hunger of a happy sub in Jack's eyes.
God I need to get off. I need to get my dick wet so badly. Tyler pulled back. He looked down and saw their hard dicks between them. Jack really had a pretty cock with a nice helmet head. When Tyler watched porn he watched for the girls, but he always picked the videos with the guys with big cocks of course. Looking at their dicks next to each other inspiration struck him.
"Dude I'm going crazy. I need my dick sucked so badly.", Tyler said.
"Shit man me too", said Jack under his breath."
"I'll suck you if you suck me..." he broached. Not caring if it sounded gay. Jack nodded at him with no hesitation and Tyler took the lead and dropped to his knees. Jack's hard cock sticking out in front of him. The shower really was resort quality, well tiled and frequently cleaned so it didn't feel weird at all getting on the floor. Tyler had never really given sucking a dick a lot of thought before, but he had been on the receiving end of some high quality and some very low quality head over the years. He was careful to avoid his teeth as he took Jack's dick in his mouth, surprising himself by how into it he was. He loved eating pussy and how much power giving good head gave him over girls, and found the same spirit transferring here. He began enthusiastically moving his head back and forth over Jack's long shaft feeling his dick twitch as Jack breathlessly told him how good it felt. Eating pussy was more fun and complex, but this wasn't bad either. After a bit of head, Jack started to thrust a bit into his mouth which surprised Tyler. Tyler braced himself on his thighs and was surprised that he really didn't mind the other man taking a more dominant role. He sat back his dick still painfully hard while Jack picked up a good rhythm. Jack continued till he suddenly pulled away, his dick making a popping noise as it pulled out from Tyler's mouth.
"Shit man, I was about to bust", Jack said. "Let me get you." Tyler happily obliged, standing up causing his still hard dick to flop around. Jack got down on his knees and started to suck him right away with a familiarity that Tyler wasn't expecting. Most girls had trouble getting all of Tyler's thick cock in their mouth without any teeth, but Jack had no problem. He began to slide up and down on his dick like an experienced cock sucker. Tyler started moaning encouragement to him under his breath loving the feeling of a wet mouth on his dick after so long.
"Fuck you're good at that man. Your mouth feels so good on my cock. You look so hot down there." Getting a little gay with it, but he didn't care. Tyler loved the way a sub responded to him being vocal. He decided to lean into it all the way.
"Fuck you suck my cock like a good boy." Jack moaned on his dick at the phrase good boy.
Got him.
Tyler decided to ride the momentum and imitated Jack. Putting both his hands around his head and began thrusting into his mouth. Jack let out a higher pitched moan, and Tyler knew he wasn't going to last much longer. "You love my cock in your mouth don't you? Are you a good enough boy to take the whole thing?". Tyler began to thrust even further into Jack's throat conscious of his gag reflex, but he never found one. Tyler's breath caught as his dick bottomed out in Jack's throat. His lightly trimmed pubbed hitting Jack's lips.
Holy Shit. Tyler had only encountered a handful of girls without a gag reflex who could take all of him. Jack looked up at him with a lustful slutty look filled with cocksucker pride. He noticed Jack was stroking his dick while he faced fucked him. That shut down conscious thought for Tyler, and he began to forcefully use Jack's throat feeling his nut quickly approaching. He wanted to cum in Jack's mouth, but also wasn't sure if he would be cool with that. He thought about asking but before he could form the words he felt the familiar sensation building. He pulled his dick out of Jack and started to jerk it letting out a deep grunt. He sprayed cum all over Jack's chest as he finished. Jack kept jacking his dick too and Tyler saw it start to spray all over the tile.
They both stepped back under the showers letting the water wash over them in silence. Fuck Tyler needed that, but that was definitely the gayest thing he'd ever done. Confused feelings washed over him, but he finally felt a little relieved from his state of near constant horniness. Tyler checked his watch again and noticed he was still on time for his first meeting thankfully. Things were a little charged between him and Jack, and he wasn't entirely comfortable feeling that way about a guy. He played it cool though and Jack did too, making him feel more comfortable as they chatted.
Apparently Jack wasn't going to be in Florida for the whole summer. He was going to go back to school for summer classes next week. Tyler was a little relieved at the space, but also a little disappointed that his new found friend and hot ass wouldn't be around long. Tyler asked him why he wasn't taking remote classes from down here. Jack replied he was really going back to see the kinky goth girl who was also in the same summer courses. Tyler didn't blame him, a built in fuck and study buddy sounded like the dream. Tyler didn't really feel jealous of her, Jack was fun but it was only just sex at this point.
Tyler eventually had to excuse himself to make his first meeting, telling Jack he would text him this weekend. He might finally be free from his crazy work schedule and definitely wanted to get some beach time in. He made his first meeting just in time. He got a "Glad you could make it on time today" message from Ms. Bryant. She was way more hands on than he expected a Senior Director to be with an intern. She even scheduled a one on one for them to catch up each week, which felt normal except for the fact it was on Fridays at 6:30 pm! No sneaking off at noon to start a weekend trip early for him this summer. Though he did need to ask her about what the policy was for taking off as an intern as one his fraternity brothers, who was in the class above him, had gotten engaged the previous year with his highschool sweetheart. Tyler was a groomsman and was excited for the bachelor party. Though he thought it was insane they were getting married so young, but they were cute together so he kept his thoughts to himself.
Work went by without a problem. He really liked his team. Jeremy the senior engineer was overworked and stressed, but despite that a really chill guy. Very nerdy from all the anime posters in the background of his zoom calls, but not in a cringy way. He was a good teacher and he spent most of his time in teaching sessions with him, and shadowing one of the junior engineers on his team, Anna. Unlike Ms. Bryant, Tyler's usual winning smile worked on Anna no problem, so she was always willing to take extra time to help him with his work. She was only a year or two older than him and a recent college grad, so this was her first time being senior to anyone on the team and so the cute brunette took to it like a momma bear. Checking in frequently and lending helpful knowledge especially on things that Jeremy took for granted, but wouldn't occur to a newer developer. Between her attention and Ms Bryant's, Tyler didn't get many opportunities to slack. Before he knew it it was 6:30 and he had his one on one.
Ms. Bryant was cold as usual, but Tyler had gotten used to that at this point. She definitely resented the fact she was tasked to manage an intern, but was still serious about it enough that she didn't delegate him to another manager. Tyler was confused by this paradox and just guessed she was someone who took all her responsibilities very seriously. She was a total hard ass but seemed incredibly competent, asking him questions about his projects in more detail than he would expect from senior leadership. He really wanted to impress this ice queen less because of her looks but more for her professionalism. She did look amazing today too, once again dressed in a conservative blouse that couldn't completely fail to hide what his fraternity brothers would refer to as "pillow tits". Having a babe of a boss wasn't helping with sex drive at all. He jerked himself from absentmindedly looking at her chest and focused on her words again.
"Well you've made much better progress than I expected you to in just a week.", she said. "The fact that you're putting in pull requests within 5 days is a great sign. Don't worry about all the comments from Jeremy, that's normal for a Senior dev. He actually told me he was impressed with you so far, but don't get a big head." Tyler smiled at that and did in fact get a bit of a big head. "I don't want to completely take up your summer", she went on. "Feel free to log out till Monday. You've earned a break." she said with a slight smile. The smile looked surprisingly casual on her face, but completely unfamiliar to Tyler. I guess she isn't always so icy. He thanked her and left the call, closing his laptop finally around 7pm. He cooked himself some dinner, loving using his parent's kitchen which was far nicer than the 4 electric burners he had in his college apartment. After making himself a nice fish dinner he settled in and pulled out his phone, texting Jack to see what he was doing. Jack quickly replied back that he had a facetime date with the goth girl. Tyler was a little disappointed, but understood. Plus things were getting a little heated between them and he wasn't sure how he felt about everything that happened in the shower yet. Though he did get a bit turned on recalling face fucking Jack. Jack replied that he was down to day drink on the beach the next day though, which sounded perfect to Tyler.
Having some time to himself he thought about what he was in the mood for on a Friday night, and the desire that won out was horniness. He never really used dating apps at school, he could always meet someone at a Frat party or the bar, but his friends swore by them. He downloaded Tinder and added a few pictures to his profile. Hoping the big name of the company he was interning for would win him some points. He added a picture of him deep sea fishing last summer with his Dad. One it was an impressive catch. Two it let him add a picture of him shirtless showing off his toned chest and core without it being a gym mirror pic. He started swiping, but to his dismay nearly everyone was a single mom. It was a beach town so there weren't a lot of local girls his age, and the ones who were down there very clearly got pregnant in high school and stopped taking care of themselves which just wasn't his type. He quickly went through everyone in the area, only really swiping right on a few waitresses and bartenders who were admittedly super hot, but didn't match back right away. Exhausted from the week and a bit discouraged about going through the local dating pool in 20 minutes, Tyler went to bed early. He missed when this place was filled with tourists and he could just find a date at the hot tub.
After sleeping in, Tyler met Jack down at the beach after lunch. Tyler filled a cooler this time, probably a bit too ambitiously, with a whole case of beer plus some margarita mix and tequila. They started off with margaritas, their two loungers and umbrella being the only ones occupied on the beach. It looked like the attendant put out some umbrellas and just left since the place was still a ghost town. Tyler asked him how the facetime date went once they got settled in and got some music playing.
Jack lit up and went, "Man that girl is such a freak. This summer is going to be so fun." But then didn't elaborate further. Tyler kind of wanted some more details, but didn't press. Tyler was pretty horny as always, and there was still some of the previous tension between them, but his big focus today was on enjoying the beach. The conversation turned to school and then sports as they enjoyed the sea breeze and plowed through their drinks. They were just getting buzzed and switched to the beers when they saw Mr. Smith walking towards them carrying a cooler and a bag.
"You boys mind if I join you?" he asked. Tyler and Jack waved him over and he pulled up a lounger and umbrella and cracked open a beer. The boys picked up their sports talk with him and after another beer he asked them if they played bocce pulling a ball out of his bag. They had not but were willing to learn. A warm up game was played and the boys got the knack for it, but Mr. Smith was clearly an experienced player and won the first three games. This got the boys competitive spirit going, and pretty soon they were happily tipsy zoned into the game.
Tyler was a gambler at heart, and after the third round suggested the loser of the three take a penalty. At this point it was about the middle of the afternoon and Mr. Smith was buzzed and Tyler and Jack were well on their way to drunk. Both still harbored hopes of beating Mr. Smith, but had gotten really into their battle for second place. Jack suggested they take a shot, which caused Mr. Smith to raise an eyebrow at the already tipsy young men, but he didn't make any further comment. Four more rounds later Jack and Tyler were both two more shots deep and several more beers deep and started to get bored of the game. Neither coming close to beating Mr. Smith, and the two of them deadlocked in a tie, they went back to their chairs. Good and drunk now Tyler kept catching himself looking at Tyler's ass filling out his swim trunks. Mr. Smith's presence kept things from getting flirty again though. They kept drinking and hanging out till an attendant came to take down the Umbrellas. To their surprise the beach attendant was actually a girl a few years older than them. She was short and fit wearing a bikini that showed off a toned stomach and quite the ass. Mr. Smith made a comment that she was going to get a lot of tips that summer if she dressed like that. The boys nodded at his accurate, but slightly creepy, comment. When she finally made it to their loungers she made a little small talk with them laughing at both the boys' pretty openly drunk attempts to flirt with her. Her name was Emily and she was going to be working there for the summer. No she couldn't have a beer with them, she had to go to dinner with her boyfriend. Visibly disappointed the boys still occasionally glanced at her as she went about closing up the beach. The encounter left Tyler even more horny than before and he could tell it was doing the same to Jack. He looked down at the cooler and saw they still had several beers remaining, and then said to Jack, "I think that's enough beach for me today I'm going to go take a shower. Want to just bring me the cooler whenever you're done?" Jack said that sounded great and gave him a knowing look.
Tyler went up to his unit and opened another beer he had in the fridge. He hopped in the shower and shortly heard his phone buzz. He smiled and checked his phone to see that it was only his idiot plague carrying sister texting him. He glanced at the message and stopped reading half way through and hopped back in the shower. As he was toweling off he got another message this time from Jack. "Going to shower and then drop off the cooler, if you want to hang afterwards" it said. Tyler's dick rose at thought and he replied that he could just come up whenever, and sent him his unit number. Tyler realized he was still pretty drunk and a bit hungry so he started cooking some burgers on his Dad's grill. Cooking drunk wasn't the safest or quickest process, but by the time Jack took a pretty long shower and made it up to Tyler's unit, he had several cooked burgers waiting for them as the sun began to set. Jack happily accepted a burger and they continued to drink while they ate and listened to music. Both of them had changed out of their swim trunks into athletic shorts but neither had bothered to put a shirt on.
Now fed and still pretty tipsy Tyler's mind wandered back to his dick. He broached the subject of the facetime with the Goth girl to Jack again. Jack this time without a filter, really got into the details. Apparently she was still a good verbal dom even over the phone. She made him write slut on his chest and ass with a sharpie, and crawl around on the floor for her. Tyler quickly got hard as Jack described her ordering him around and making him beg to see her tits and pussy. Jack was stroking his now hard dick over his shorts when he looked over and made eye contact with Tyler. "I told her about what we did in the shower." he said softly. Tyler was a little startled, doing gay things was one thing, but people knowing about the gay things was another. But Jack quickly pressed on. "I didn't tell you everything about her being a freak. She actually has this huge strapon. She uhh pegs me sometimes and makes me suck her off before I eat her pussy. It's crazy hot. I've never came harder in my life. Except uh when my ex used to peg me too" Tyler digested this new information over the fuzz of the alcohol.
"Oh I thought you were pretty good at sucking me for it being your first time", Tyler replied.
"Yea", Jack replied a bit embarrassed. "Ever since they started making me do it, I kind of thought about doing it with a real dick. But I'm still really into chicks still man, you know? Like Emily's ass almost had me tenting up in my shorts." Tyler nodded at that. "But yea Morgan, the uh goth girl, started telling me I was a good boy for sucking you off and that drove me crazy. She wanted me to hook up with you again"
Tyler was rock hard at the direction of this conversation. "Oh? What did she want us to do?", he asked.
"Well she wanted you to well uh fuck me... She thought it was super hot that you're thicker than her strap on. That thing is pretty big... " Jack said, trailing off looking at Tyler's dick.
Tyler had heard enough, his normal reservations about fucking with a guy completely gone from a day full of drinking and the time he had already spent playing with Jack's ass. He stood up and walked over to him. He leaned down and kissed him passionately. It was sloppy and tasted like ketchup and beer but he didn't care. Jack began reaching for his dick and pulled his shorts down while they kissed. Tyler was in a mood though. He didn't have to dom to get off, he had plenty of fairly vanilla encounters here and there, but when he had a good sub like this in front of him he wasn't going to let it go to waste. He pulled away from the kiss and stood up, his dick level with Jack's mouth. Jack hungrily started sucking him. Tyler gripped his head again and started to face fuck him enjoying the feel of his wet mouth around his thick shaft. He began to take advantage of Jack's lack of a gag reflex again and soon had an enjoyable rhythm going in the back of Jack's throat. Jack was breathing through his nose and Tyler could see the excitement in his eyes while he choked on his dick. Tyler pulled his dick away, saliva dripping off it and out of Jack's mouth. He bent over and gave his messy mouth a kiss tasting a bit of his own dick. Then he reached out and grabbed Jack by the neck and started to choke him. Jack let out a moan at this and Tyler kept the pressure up towering over him. After a minute Tyler let up, he didn't want him to pass out, and said "Get on the floor." Jack readily complied, getting on all fours ass in the air, his long dick sticking out from his shorts. "Start crawling", Tyler said pointing at the door.
Jack obeyed and started crawling towards the balcony door. Tyler turned around and turned off the grill while he made his way across the floor. After he made his way through the open door Tyler bent down over him again, cupping his ass before giving it a very firm smack. Fuck he wished he had a collar, but he left them all at school. He pointed towards the bedroom and Jack continued to crawl. Thankfully Jack was really into it because it was kind of a long crawl across the condo. Jack made his way through the condo with Tyler occasionally stopping him to spank him. When he made it to the bed he crawled up on it still on all fours with Tyler looming over him. Tyler pulled down his shorts and cupped both cheeks of his round ass. After admiring the view for a moment. Jack's ass was shaved like the rest of him, and he could see a tight hairless hole waiting for him. He spread the cheeks apart and began eating his ass. Jack moaned at the sensation of Tyler's tongue on his hole, and started stroking his dick while he pressed his face into the bed. Tyler had done anal plenty of times with his ex and a few other fuck buddies, so he was no stranger to eating ass. Speaking of which he suddenly realized he was missing a crucial component for anal. He pulled his mouth off Jack's ass, and said "Ah fuck I don't have any lube".
"I brought some,'' Jack replied huskily. "In the bag by the cooler inside." Tyler half jogged out the living room, he needed to be in that hole. His dick bounced around as he went out to the table and found the bag, and quickly pulled out a tube of lube. He regained his composure a bit and sauntered cockily back to the bedroom. Jack was waiting on his stomach, legs spread out, round ass in the air ready to be mounted. At this point Tyler felt like he was just fucking another girl, all thoughts of Jack being a guy out of his head as he admired his ass. He got on the bed and put his dick next to Jack's face and Jack happily sucked him off while he started to lube up his hole. Jack barely protested as he slipped in one, then two, and finally three fingers while he warmed him up. That goth girl must really wear him out.
Once he was comfortably taking three fingers, Tyler knew it was time. He pulled his dick away from Jack's mouth and made his way around the bed. After all his obsession with this ass he was ready to watch it bounce on dick. He knew anal took time though and slowly eased himself through his ring applying even more lube. Feeling his dick slide into his tight hole tested his self restraint. He savored the tight grip on his shaft as he stood still for a minute till he slowly started to ease himself in more. Jack moaned as he went further and further in him until he finally bottomed out, seeing his hard stomach connect to Jack's bubble butt. Tyler savored the sight then began to slowly pull out. Jack seemed to be having no problem taking him, but he still kept things slow to be safe.
Jack turned around and looked him in the eyes filled with lust, clearly enjoying being filled. "Fuck me", he grunted. Tyler took the challenge from his sub in stride and began pistoning in and out of him. Jack quickly was subdued by Tyler's new pace. His tight hole felt amazing on his cock as he watched his ass bounce from his thrusts. Tyler put his hand on the back of the neck of the smaller man and pushed his face into the bed as he upped his pace. A full day of drinking really was helping his stamina so he was able to keep fucking Jack for longer than he normally would have at that pace. Jack grunted at each thrust and was clearly loving it. Tyler kept fucking him telling him he was a good boy and telling him how tight his hole was. He periodically spanked him leaving a bright red handprint on his ass. He drove him down to the mattress using his body weight to dominate him. He slowed down for a moment and leaned over to Jack's ear and whispered, "I'm going to breed you". Jack turned back and looked at him and nodded. Tyler resumed his pace, every stroke feeling electric knowing he was about to finally be able to breed someone after months. Nothing felt quite as good as coming in a tight willing hole. Mouth, pussy, or ass filling it with cum felt great. Jack started to lift his ass to meet his strokes and Tyler felt him tense up. A few strokes later Jack shuddered and came all over the sheets below him. This caused Tyler's mind to go blank and he thrust into him even harder till he buried himself all the way and felt his nuts pump into Jack's ass. Breeding his sub as Jack's dick still was leaking cum out onto the bed. He collapsed on top of Jack and they both lay there spent.
After a few minutes entangled, Tyler got off of Jack and gave him a kiss as he climbed to the pillows at the top of the bed. Jack soon joined him and it felt natural as Tyler spooned him and they passed out with his semi hard cock pressed up to his ass finally relieved.