The College Boy Ch. 01

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Two men from different generations, exploring what man love.
2k words
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Part 1 of the 2 part series

Updated 06/09/2023
Created 04/26/2020
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trippy64
trippy64
20 Followers

This is a story of fiction, born out of an actual online encounter on a hookup website. Names places and situations have been changed to hide the guilty.

*

MMMM, baby. Keep nibbling that ear. That feels so nice. I can feel your hot cock between my ass cheeks. MMM. Ow. You need to trim your nails. And that's when consciousness started creeping into the dream world, and Greg opened one eye. 6:42. And his dog was laying on back, licking his ear and pawing at his shoulder, her tail wagging against his butt. She was early, and he tried to get her to go back down to the foot of the bed. But it was of no use. Once she had her mind on breakfast, it was a one-track train.

He crawled out of bed and stroked his morning wood, as he walked to the bathroom. Greg was 48, very tall, lean with a full head of hair and blond hair. He worked out regularly and liked to think of himself as fit. You could almost make out his abs, as he didn't have a dad bod, something he didn't care for on a man. He checked himself out in the mirror, as he walked to the toilet. "Not too bad" he thought to himself, as long as he didn't look at his wild head of bed hair. He grabbed some clothes after relieving himself and went downstairs to feed the dogs and let them out.

After the dogs were settled, he crashed on the couch for a couple of hours, hoping to relive the dream of the twinks sucking on his earlobe while rubbing his cock in Greg's ass, but that didn't quite work out the way he wanted. He was full on fast asleep until his wife came down and started their routine, coffee and whatever they were going to eat for the morning. They discussed the quarantine events and what things they may need to get settled into the new normal. Greg was the one to venture forth, while the rest of his family stayed home.

"I need some dick," Greg thought, and since he was going to run some errands, and be by himself, he thought maybe he could catch someone else with the same idea. He normally spent time in the sniffies web site, a hookup site he found at the beginning of the year. He had some nice success over the last few months, getting to play with several men of various ages.

He logged into his account and looked to see if there were any messages from the previous night. He logged in a lot; it was his escape from his middle-aged life. He liked the attention he got from the other users, and he liked to plan for future meet ups. Today, he had time, he was going to get something going immediately. His profile picture was a of his erect cock, and a dark background. Just a hint of precum dripping down the sides. Of all the pics he had, this one drew the most attention.

He liked to think he was ok looking, he has been told he was handsome, but he doesn't believe anyone when they say that. He has been married a long time, but before that lived a very bisexual lifestyle, even if he was closeted. He had numerous trysts in the past few months, but with the quarantine, it was drying up quickly.

His first gay encounter occurred when he was a younger man. He and his college roommate would occasionally play with each other. At first, the rules were: no kissing, anal, or oral. But those rules slowly relaxed as they experimented over the ensuing years. The only rule not broken was kissing in the end, it was never about that. After college, he continued sleeping with guys just as much as girls, but hew never dated a guy, nor considered it. It was just the sex he enjoyed.

He got married a little later in life and hadn't been with a man since. He and his wife raised two kids and were and with one kid out and the other in HS, they were starting to see what life would be like as empty-nesters. Greg didn't like what he saw and started looking around for something to augment the dull married sex he had, when it occurred, if ever. When he found this site, it suited him fine, as he didn't want to be on Grindr or anything.

Greg's profile consisted of one picture of his hard member. It was framed against a dark room and stood out in the many pictures on the site. He usually got a lot of "Nice dick" comments, mostly from MWM's who like him, couldn't host only talked about getting together "someday." As he was answering some of these chats, a new message appeared. It was from an anonymous profile in the next city over. Not too far out of the way. Greg thought he might see if this will work

"Hi." At least it didn't start out as a dick pick.

"Hey." Greg's standard reply.

"How are u doing?"

"Good, you?"

"Good just woke up horny"

"yeah? Got some hot morning wood?"

"Yesss lol"

"Nice. what are you into?"

"Getting head and jerking another guy off."

"You into older?"

"Yessss"

"How old are you?"

"20"

"I'm 48"

"Nice"

"Seriously into older guys?"

"Yes, big fantasy of mine"

On the other side of the chat was Jake, a 20-year-old college student home from school because of the quarantine as well. He was average height, with nicely defined muscles and brown hair and blue eyes. His chiseled smooth abs tapered down to some very trim pubes and large 7-inch cut cock, with smooth balls. He was stroking his cock as he was chatting.

He woke up hard as ever and wanted release and thought he might find someone to suck him off. It had been a while since he was forced home from school, and he wanted something quick. He too, had been using sniffies, but he had yet to pull the trigger. He's been with two other guys before, one his age, and one older. Otherwise, he spent most of his sexual attention on girls. He's had several girlfriends and considered himself straight for the most part. But he also had this one fantasy about being with a guy. Especially an older guy. The conversation continued and the more Jake chatted, the more he was recalling his first encounter with an older man. He had just graduated from high school. The man was a dad of one of his friends, whom he had spent many a night at their house. He was a nice man, and Jake had a secret desire to have the man suck his dick. But Jake could never figure out a way to approach him.

They didn't exchange names, but the Greg agreed to meet Jake at 1 at the local school parking lot. It should be empty, and the plan was to hop into Greg's car and have a little fun time together. The idea of it all thrilled Jake, and he started fantasizing about it, and that turned to the one time he spent with an older man a couple of years previous, the summer after high school.

After a beautiful lacrosse game for summer league, where Jake scored the winning goal, the man came over after and congratulated him.

"Hey Jake, quite the winning shot!"

"Thanks sir, it was fun to do, hoping their defense would set up like that."

"Yeah, you didn't telegraph at all and slam, no one saw that coming. Look at how sweaty you are, and how your shorts are sticking to those thighs. If I were a girl, I'd be all over you." The dad said.

Jake blushed, but even more embarrassingly, he started to chub. "Thank you, sir, haven't had much luck with the ladies of late, but it could still happen." Jake smiled, as he slowly moved his gear bag in front of his body to conceal his growing member. The thought of this man checking out his thighs was more than he could bear.

"Looks like you need a little help there." He mentioned as he gestured toward Jake's growing "problem." Jake didn't know what to say. He was confused by wanting to just walk away, but here was this man he fantasized all through HS checking him out and eyeing his bulge.

"I am not sure..i ...yeah.." was all Jake could mutter. He'd jacked off to a moment like this, with this very dad, numerous times. And how here he is, the subject of all that spilt cum, talking to Jake about his growing cock.

"your sweaty body and hair are really turning me on as well." The man said. "ever want to have a man suck you off?"

"OMG, here, now? There's so many people around." Jake was stoking his cock hard now remembering the initial conversation.

"I want to sniff that sweaty crotch in your compression shorts, pull them down, and suck on that cock of yours .There's a spot over by those trees, we can go there, no one will see us .I want you to fuck my mouth"

The man leads Jake down to the trees and they position themselves, so they are hidden from view. He reaches down and rubs Jakes still member through his shorts. Jake pulls air in between his teeth he feels the man's hand all over him, moaning as well. He's dreamt of this, and here it is happening.

"You're making me so hard, in my shorts sir." Jake says as he grinds his cock against the man's hand.

"Yeah, let me rub it for you. How's that feel?"

"Oh god, that feels so nice."

"You have a nice size cock; it feels good in my hands. Want me to pull it out, suck on it for you? Would you like that?"

"Please, there's nothing more I would like right now."

The man pulls his compression shorts down, exposing Jakes dick and he slowly starts stroking it as he kneels. He grabs it at the base and licks the head, tasting the precum oozing from the tip. The man slowly kisses and licks the shaft from the head down to the balls and back. He is taking his time, teasing Jake.

He takes the head of the dick in his mouth and starts rolling his tongue around rubbing it all over, and slowly sucking it in, letting more and more of his length into the man's mouth. Finally he has it all the way in and is sucking him hard, breathing through his nose, which is buried in Jake's pubes. Jake cannot believe this is happening. It feels so good, and he can't hold back any longer.

He starts to convulse, closes his eyes and yells out "ahhh" before he could warn the man about his impending orgasm. He jerks and grabs the guys head to steady himself, as he dumps the contents of his balls into the man's waiting throat. For his part, the man doesn't let go, and keeps a solid lock on his dick as he swallows every drop.

And with that, Jake cranks out his load onto his chest, reliving that one night with the older gentleman, as he has done so many times since its occurrence. He cleans himself off and logs off the site to go see what's for breakfast.

Greg goes about his errands, checks the time, see it is almost one, and stops by the school. He doesn't believe the kid will show but doesn't want to miss out just in case. After waiting 5 minutes, his prediction came true. He took off to his next stop, and figured it was for the best, as he just now realized the kid stated he lived close to the school in his own city, not the adjacent one. That hadn't entered his mind until that very moment. What if he knew this guy?


trippy64
trippy64
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