The College Boy

Greg was working from home on Tuesday, as he would be every day during the quarantine and while on a boring conference call he logged into his personal computer to get in sniffies and see if anything might shake for later on that day. He noticed the same profile in the next town from the previous Saturday. The events of the conversation, and the afternoon rolled into his mind.

And then, the panic set in again. The guy's profile was in the next town, but he said the school he was to meet Greg at was right by where he lived. The school was the same school his own son graduated from. They were not the same age, but his son also played sports. And Greg did some work for his son's team as well. If he knew this kid and they met up, the results could be disastrous.

And in their conversation, he did say he was a former athlete and liked to keep in shape. Perhaps he didn't play the same sport as his son. Yeah, he probably dodged a bullet by not meeting up with this kid. He decided it was best to leave him alone and not do anything when he got an incoming chat.

"Hi."

"Hey." Greg's standard reply. Then he looked up where the chat was from, and it was the same anonymous profile from Saturday. Greg's heart began to race, but then, he wasn't 100% positive.

"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."

"Ah yes, little mister 20 yo that doesn't follow thru. BTDT." Said Greg. He was going to give a hard time, then just ignore him. He didn't feel like wasting his own time, and he was sure this kid was either playing around, and not serious, or he was going to cause him grief in other areas if it went further. But then, what else did he have to do, listen to a bunch of coworkers drone on about the challenges of working from home? Let us play along and see how much fun he could have with this kid.

"I'm sorry. I think I busted my nut shortly after talking to u."

"I kinda knew you weren't going to show up anyway but took a chance. So the fault lies in me. I was just hopeful for a nice dick to suck, it's been a month." Greg was playing trying to lay down a little passive aggressive guilt.

"Did u try to meet at a school?"

"Yes."

"I'm so sorry did u end up going there?"

"It was on my way to run errands, so I only wasted 5 minutes." Greg was smiling, enjoying how the kid was scared Greg be mad. The power play was working in making his morning a little less boring.

"Oh okay good cause I didn't get on after we spoke."

"No worries, like I said, it was my fault."

"I should've just went." 'Yeah Right', Greg thought. That would have been the scare of our lives if he went through it.

"Would have been a nice warm mouth instead of your hand." Nice way to keep the conversation going..

"Sometimes not cumming is the best way to cum later, delay gratification..." Greg was laying it on thick. Then he remembered his earlier panic, about what school this kid went to, and how familiar he might be.

"You play sports?"

"I did in high school." Jake replied

"What sport?"

"I'm pretty athletic. Lacrosse." Fuck. Same sport as Greg's son. His heart was racing now, and a panic was back about the near miss he had.

"What HS did you go to?"

"Why are u asking?"

"Because if you went where I think you went, we need to stop talking." That was it, he was not taking this any chances. He should just block the profile now and bail out.

"U got kids?" Jake asked?

"Yes."

"I mean we don't even know what each other look like."

"True, but once we meet, that is no longer true."

"What's the big deal we would know each other. "

"So that means you did go to City HS."

"Yes and u knew that and I ain't gonna lie to u lol."

"Well, your location is the other city, and I didn't 'know' that, for sure."

"Yes Ik for anonymous reasons."

"Yup., I get it. But for sure we know each other; I probably know one or both of your parents. Have a good time."

"Sad." Said Jake, taunting Greg. From his perspective, having one of the dads from lacrosse was a huge turn on, and his dick was getting hard thinking about it. This was a fantasy come true, once again.

"I cannot risk it, you played sports and probably are friends with my son. unless that is a thrill to you and you are dl."

"Sorta turning me on lol." Jake was really getting hard now, and his goading the old man worked, he is still chatting. Jake was also curious who it might be. Could it be his friends' father from a couple of summers ago, right after HS? While that guy was good and all, there was one other dad he really had a crush on, and it was from a kid a couple of years older. Now that man was someone, he wanted to have suck his dick. Wouldn't that be special.

"Are you discreet?" Perhaps Greg could trust this kid to keep it secret. Maybe. He had a hot cock when they shared pics.

"Of course." Jake wasn't about to let anyone know he was into guys. He was as straight as one could be, except letting older men suck him off. That was something he fantasized about. He had one guy his age, but it wasn't as hot.

"Well then, it will be a fun surprise if we ever hookup." Greg replied.

"It would've been weird if I knew of u and we met up before this convo."

"I should have put two and two together and did the ask before we met, a little risky on my part."

"We are all a lil risky right?"

"Somewhat, but I have way more to lose than you do. You get outed, maybe. I lose a home, a family."

"Yeah that's a lot. How long have u been closeted?"

"No, it's everything. And I have always been closeted, from the first time I played with a dude, right out of HS."

"Dang what made u suck a dick back then?"

"We were both curious. started out JO'ing together. Then jo'ing each other, then it progressed from there. i probably have always been bi. not probably, I like sex with both guys/girls." Greg prided himself on his equal enjoyment of sex with either gender. It did not matter to him what hole he was balls deep in, and he loved sucking clit and tits just as much as cock. And he liked to point that out anytime he could.

"Have u had gay sex?"

"Yes."

"Top or bttm?"

"Both."

"Did u enjoy it?" Jake was surprised how open this man was being about his experience, and he was very curious to hear more. Of course, the guy could just be blowing smoke up jake's ass, but it didn't seem to be the case.

"Very much so, otherwise I wouldn't be here now..."

"True, which one did u prefer?"

"Oh, you mean anally specifically. Yes." Greg was confused at first because they were rapid fire, and he was going down a different train of thought than the next question revealed the true intent.

"Yeah did u like bottom or top more?"

"I enjoyed each for their own reasons...I like getting guys off, and who doesn't want their cock in a hot hole."

"Yeah, I just feel like bottom would make me so uncomfortable." Jake had never had a desire to do anal. He was fine just having guys suck him. That's as far as he'd gone, and he hadn't really fantasized about going further. But for some reason this question and answer session was really intriguing to him.

"Do you ever finger your hole when playing??"

"I've done it once. Didn't really do anything for me."

"So, you aren't sensitive there."

"I am, I like my hole being played with without penetration. I guess idk tbh."

"Do you like getting a rim job?" Greg continued probing, as the flow of the chat was more engaging than his work, but also, he was thinking there was more to the young man than he first thought. He might be able to make it work somehow. The idea of playing around with a 20-year-old was just what he needed to overcome the lock down blues.

"And if the right top gets you, and shows you the ropes, the discomfort goes away to some pure bliss as he hits your magic spot." Trying to see how far he could get the guy to commit to in chat was pushing it, but it was worth a shot to see where his curiosity has really taken him.

"Lots of lube, right?" Jake was not sure he wanted to try any time soon, but he wanted to know how it worked.

"You only need a little, the trick is to relax the muscles. it will be uncomfortable the first time, not lying, especially if he is huge. But if he is skilled, you never came like that, Ii shall tell you. Mind blowing. Orgasm." Again, trying to push the envelope.

"I don't think I'll try it anytime soon. Damn that sounds hot tho." And just like that the door closed, and then was pushed back open ever so slightly.

"I never push anyone outside what they are comfortable with. But i share my story, because you are where you are in life, to not limit yourself, and try things there." Greg again, pushing the envelope.

"Yeah for sure and I appreciate u for sharing."

"I have to run errands later this afternoon. You free?" Greg had to get to another meeting and wrap this up, but he wanted to see where this kid's mind was at.

"I have class at 1, but I can probably meet somewhere at 3?"

"How about the old grocery store, back there is very private."

"What are we going to do?" Jake wanted to be sure he was only going to get a blow job, and maybe stroke the guy off. Hopefully, nothing more. For Greg's part, he really was horned up from all the talk about sex and wanted release anyway he could get it.

"I can suck you off, and then you can do whatever you'd like to me." Said Greg.

"Cool. How do I reach you?"

"Have kik? My user is sourpussy22. Don't ask. But my name on there is Random Dad."

"I never used that."

"Download it quick, it is easier to use than this site, and it is private. Very discreet."

A few moments later a notification alert from kik pops up on Greg's phone, from "Random Som." There was an attempt at spelling, but it gave Greg a smile, that the guy attempted to be Random Son, and he replied quickly.

"You made it."

"yeah, but I didn't spell it right lol."

"No biggie, I like that you copied me. See you at three, use this if it is a no go for some reason. "

And with that, Greg went to work, and Jake went about getting ready for his day. He was extremely nervous about potentially knowing who this was, but at the same time, that made it hotter in his mind. He showered and stroked off, hoping to make it last if it was going to work with this guy, but also getting off in case it didn't work.

The appoint hour was near, and while on his class, Jake could not concentrate. The professor was droning on, and the connection was in and out. But mostly, he was worked up over meeting this guy. He was anxious that it would be someone he knew, but he was also excited to get another blow job from an older man. And more importantly, was it the one guy he had a crush on? The store was 3 minutes from his house, and he hopped into his car just before three and headed over. And as he pulled around to the back of the vacant store, there it was, a big black BMW with tinted windows, just like he said. And it was very out of the way. So far so good.

He pulled up next to him and put his car in park. He could see the shadows of the man, but he couldn't make out any features, but for sure, the man could see him. He pulled the key out of the ignition, and slowly exited his car and walked over to the driver's side of the other car. Here goes nothing. The window slowly lowered a little and he could make out the man's face, and...it was him! His crush from lacrosse. He had to control himself to contain his excitement. The man looking back at him had hard features, brown hair, a gray beard, and long brown hair. Hadn't changed much since he last saw him.

For Greg's part, other than the few boys that his son hung out with, he really didn't know the boys. Oh, he knew all the names, as they always had rosters printed up, but to put a name to a face, that wasn't something he spent much time doing. And besides, they always had a helmet on, so you really couldn't tell one player from another without the jersey number. Otherwise, the young man looked pretty fit, with black hair and blue eyes.

"You made it."

"Sorry about before."

"No worries. Well, are you weirded out?"

"No. Not at all, kinda excited, actually." Jake smiled.

"Want to meet me in the back seat?"

"...Yeah." This was it. Jake was going through with it. The gentleman got out and directed Jake to the passenger side, while Greg got in on the driver's side after pushing the driver's seat up. When Jake sat down, he noticed the front seat was all the way up, plenty of stretch out room. Even had a little footrest popped out under the back of the front seat.

"Name's Greg, btw."

"Jake S..."

"No no, don't want a last name, just in case I know your folks. Nice to meet you Jake.. Greg started rubbing his hand along Jake's thigh moving closer and closer into and around his crotch. He looked the man over and saw a bulge in Jakes' sweats. looks like you are excited to be here."

"Yeah." Jake's mouth was dry, and he was still nervous, but he liked the attention he was getting.

"May I?"

Jake nodded, and as he did so, the man slowly moved his hand from the inside of his thigh to an extremely hard cock pushing against his fabric. He ran his hard up and down through the sweats, and a wet spot appeared at the tip, as he was leaking precum profusely at this point.

"We're letting perfectly good precum go to waste, there." as he shifted around to put both hands on the waistband of Jakes shorts and pull them down to expose his dick. The head glistened from the oozing precum, and Greg bent down to lick it up.

"mmmm." That was all the encouragement needed to slide his mouth over the head of Jakes cock and slowly suck his full length into his mouth. He pulled it all the way in and slowly released. Working his tongue around the shaft as he moved up and down. Jake was breathing very heavy now, and pulling breaths in between his teeth.

The man was very skilled with his mouth, and this by far, was better than nay blow job he'd received from his several girlfriends. Just as Jake put his hand on the top of Greg's head, Greg grabbed the base of the cock and started really focusing on the head when he could sense Jakes balls tense up and without any warning, Jake came rapidly in his mouth and down his throat. He thrust his hips up as he shot rope after rope, panting hard.

"Oh my god, so sorry, I didn't warn you.." he stammered, as Greg focused on lapping up every drop. He finally looked up from Jakes, lap, smiled, licked his lips, and said, "Good to the last drop. That was hot, but you hardly had time to enjoy it."

"Yeah, sorry, didn't expect to cum that quick."

Well, maybe we can go again after you rest. Now, what do you want to do in the meantime?"

Greg sat back on his side of the car, spread his legs a little, and looked Jake over. There was no expectation here, but he was hopeful. Jake slowly reached out and put his hand on the man's jeans and rubbed. "Well, I could jack you off, and then see where things stand.." as he said it his hand moved up Greg's jeans rubbed his crotch, noting that he wasn't quite as hard. Greg undid his belt and opened his jeans. "Help yourself, let's see what you can do." Exposing his semi hard dick, Greg leaned back as Jake reached over and took the member in his hand. He stroked a couple of times and felt it swell and grow somewhat from its slightly chubby starting point, but mostly, he was mesmerized by a huge stream of cum pooling along the head and skin of the cut dick. Jake put a finger on the top of it and raised up up watching the stream stretch.

"You leak a lot."

"I guess so, you are making me very excited."

"Really?'

Greg nodded. And he was vey excited, and slightly nervous. While the odds of getting caught were low, he was still concerned this could all blow up in his face. At the same time, to have the attention of a college boy, and not some of the normal married guys trying to fool around, was way more than he had hoped for. He was very turned on by the young man next to him, stroking his dick, and he hoped this was the start of something, and not a one-time thing, which is usually the case in these instances.

'Mustn't let our emotions go crazy, dude, its just a fling, nothing more.' He tried telling himself, but that voice was overcome by another thinking, perhaps, this is truly, the start of a journey.

Meanwhile, he started moaning more as Jake's attention to his cock started to make him fully hard. Jake continued stroking him up and down and staring at the cock, as it got to it's full almost 7-inch size.

"Looked bigger in your picture, and you look like you trimmed."

"It's amazing what you can do with a little wide angle and yes, I trimmed up since my last pic." Greg chuckled. While not huge, he was pleased with his size. As Jake continued working him up to a full lather, Greg put his hand on Jakes back and shifted to get a better angle.

"Oh, that's it, I am so close. "

"Yeah?"

"Yeah, keep going. Almost there. "

Jake started stroking faster as Greg could feel the pressure mount inside him. "Oh yeah, I am about to cum." And with those words Jake started pumping furiously, like he would on his own dick, and a few seconds later "I'm gonna cum..ohhh ohhh." Jake felt the cock in his hand tense up and cum was spewing out the slit all over his hand. He kept stroking till he felt a hand on his wrist to make him stop as the man moaned. He looked up and saw the ma's eyes closed tight as he shuddered through his orgasm. The sight of it made him get hard, knowing he had just made another man cum with his hand.

He looked down at the result, cum all over the Greg's crotch and his hand, and the smell filled the car with that same smell he noticed at his own hand. Greg reached down and grabbed a towel he brought for clean up and started wiping himself off, then handed it to Jake. Jake sat back and cleaned off and noticed his own hard-on. "Hey, it worked, I am ready again."

"Well then, swing this leg around so I can get between them."

Jake moved his leg around the back of the seat, and Greg slid up and had his head right in Jake's crotch. He wasted no time in pulling jakes dick out from his sweatpants and started sucking on his cock head. He also used his tongue more. Licking and nibbling up and down the shaft as he fondled Jake's balls. All of this was making Jake squirm, and moan. Greg continued to tease and lick the shaft while squeezing lightly on the cock head, and then went all the way down and pulled one of Jakes nuts into his mouth. Jake sighed at the sensation and closed his eyes. This was way better than the first one and he wanted it to last longer and enjoy it. The man clearly knew what to do, and he was glad to be on the receiving end. As his balls escaped the man's mouth, he felt him nibble up the length of his dick and then swirl his tongue all over the head, making him moan with delight.

Greg continued with his mouth, slowly pulling the dick deeper and deeper until his nose was buried in jakes pubic hair, breathing through his nose. Then just as slowly moving up to the head and then back down again. His oral ministrations were doing the trick too, because Jake was moaning and sucking in his breath with each stroke on his dick by Greg's talented mouth.

Jake took over, and placed his hands on the Greg's head, and held it there as he started thrusting his manmeat in and out, fucking Greg's throat. His pace much faster, but he could feel that he was building up to another climax, the third of the day, and he wanted to control it. He longed for this day, the day this man finally sucked his cock, and here it was, and Jake was savoring every second. Greg looked up at him, his mouth held firm, as Jake watched his dick slide in and out, and he lost all control, and dumped a third load into Greg's mouth, and not a drop seeped out. Greg held onto Jakes hips as he sucked and swallowed every drop of cum.