The unfortunate pen pal buddies - M/MM

[John]

Hey guys, disclaimer that this is the first M/M story that I've tried writing, so it might be a total failure. But anyway, let's give it a go.

Characters:

John: 30 year old male, 5'9, 170 pounds, semi-fit and black-haired, straight.
Jerry: 44, 5'8, 180 pounds, a bit more on the dad-bod side, gay.

Part 1:

John and Jerry had been pen palls for about a few months now. John was straight, but he'd always wondered what it would be like to get tied up with a guy. He met Jerry in one of the kinky forums they both frequented, exchanging some ideas and fantasies and it turned out that they had some similarities in terms of bondage tastes.

They had written for awhile now, but didn't have a chance to meet. Work was hectic for both of them, until one summer day in the middle of June when the business had subsided and they finally got a chance to arrange a meetup.

An interesting opportunity had arisen. An older guy in the same forum, using the alias Charlie, had offered them 10 000 dollars each if they were to complete a set of bondage challenges, initiated by him, live.

The first one was just around the corner, it had to be today. They had arranged to meet at this local diner stop, out near the middle of nowhere, where the first challenge had to take place.

John entered and was instantly waved by Jerry, who had apparently arrived first.

"Hey man, sit down, great to meet you in the flesh, finally."
"Yeah, good to meet you. Gotta tell you, I'm a bit nervous. I've never actually done bondage before, at least with a guy."
"Let's see if it's as good as what you were picturing during our chats, haha."

They exchanged some back and forth chit-chat, talking about work and whispering for the mysterious first challenge which was yet to take place. Jerry was supposed to receive a message about it in a minute.

To make sure the guys actually complied with the challenges they had received a one-time link, with a live feed, which had to be turned on once the challenge started. To ensure both sides had some security Charlie had already prepaid them 3000 each, or roughly one third of the total pay. In order to get the rest, they had to complete the five challenges.

Finally, a notification sound could be heard on Jerry's phone. "Here we go, man. Number one is here."

They stared at the message in astonishment. The first one was for John and was curious, to say the least. It said: make sure to hold on for 20 minutes and there was an additional note, saying: go to the bathroom, first room to the right, you'll find additional instructions.

Curiously, they entered the men's bathroom, checking out the first room to the right. No one there, but a small little note, a pair of handcuffs, a ball gag, a COVID cover mask and .... a brand new cock-ring type vibrator with a remote.

The note read: first one is for John. You have to return to your booth. Before that you are to insert the vibrator and Jerry was to control it with the remote. It will be set on low and it will alternate between low and mild. You will insert it on your dick, gag yourself with the ball gag, put the face mask over it and go back to the booth. Then Jerry will order some fries, as you fight with the vibrator. Your objectives are not to finish and nobody to find out you're gagged. Both of you will receive a thousand dollars more in your accounts upon completion. You will have to turn on the live camera feed now.

"Okay, let's start this shit. Gotta admit, I'm a little nervous."
"Don't worry, man, we will have each other's backs."

Jerry accessed the live feed link through his phone and the camera started filming. John turned against it, stripped to his boxers and inserted the cock ring. It was a strange feeling. Then he put on his jeans back again and grunted to Jerry: Let's try the settings and see what the difference is. But before that you have to gag me with the ball gag."

Jerry took the ball gag and thrust it gently into John's mouth, buckling it behind his head.

"How's that?"
GOODMMPHH.

John put on the mask and motioned t Jerry to try to settings on the vibrator, as the clock was already ticking.

Jerry started with low. The buzzing was frustratingly nice, but it wasn't something John couldn't handle. Then he switched to mild, raising up the volume.

"Mmpphhhh mmmpgjhhh" John started grunting.

"Okay, okay, buddy, I got you. Let's try it this way: 4,5 minutes, low mode, 30 seconds on mild. That way you can make it."
Okayhhmpp."

They exited the bathroom, John receiving several stares because of the mask, it was the middle of June and the COVID pandemic had subsided, so people were curious as to why he'd all of a sudden put on a mask, but it was a diner in the middle of nowhere, after all, weirdos galore, and after while they stopped paying attention.

They returned to the booth and Jerry ordered french fries, alternating between low and mild with the remote.

"Mmmpghhhh, noompphhhh, mmpghshdh"

"Come on, buddy, you can do it."

John was sweating from the effort and the overall weather and was grunting as quietly as possible. The minutes ticked by. He was desperately trying not to cum. The camera feed was set up at the end of the table, so the viewed had direct access to his frustrated posture and the way his face and eyes told the story - brows moving, eyes fixing the camera with its stare, quiet, unintelligible grunts escaping his mouth. It was so very frustrating and several times he came close, oh, so very close, but they made it. The alarm notified them the challenge was completed and Jerry received the following: congratulations, you have just received your prize by completing challenge number one. Await further instructions for challenge number two.

"Nice, we made it, man. Good job. I could see you were struggling a lot. Do you wanna finish up? I have the remote, it's connected wirelessly to the ring. If you go to the bathroom, I can set it up on high and you can finally finish?"

"Yesshmpp, pleaampphh, manppghh. Immm cantmmpgg waimghf anymopphkk"

John quickly sat up and almost ran to the bathroom, hoping nobody would notice the way his dick was pressing against his tight jeans. He entered the room, where originally they'd found the items of the first challenge. He'd just locked the door behind him, when the buzzing increased.

"MMPGHSHDH, HELPMMGH MEEPLGHH, YESLLKMMPH"

He was so frustrated that it didn't take a lot of time. With several violent thrusts and his grunting and moaning increasing in volume he finished with a powerful and releasing orgasm: "Mmpghshdhdh mmpphhhh"


That's the end of part 1. Hope you find it interesting. Let me know in the commets. Open to ideas, suggestions or constructive criticism for future chapters.

[Guardianbound]

Welcome @John! It's a great first chapter, I'm hoping you continue writing. Jumping in for the first time is always scary but you'll get over it soon enough

[TightropesEU]

Nice opening, can't wait to read more

[squirrel]

Very interesting idea for the story, cant wait for part two!

[blackbound]

Well, they don't sound very unfortunate just yet! I wonder whence the title.

[Red86]

Interesting start. Curious how this will shift to unfortunate!

[harveygasson]

Really intriguing start and a very unique story idea I don't remember coming across something exactly like this before. I'm looking forward to seeing what other challenges are in store for the pair.

[KidnappedCowboy]

Hey, @John!

Welcome aboard!

Great first chapter...look forward to more from you!

[John]

Thanks for the encouraging commentary! Don't hesitate to pitch out ideas or shout out in case of some constructive criticism.

Chapter two:

After successfully completing the first challenge John and Jerry were ready for more (especially after the reward for the first challenge was transferred to their bank accounts).

"I wonder what happens next, the first one was more dynamic than what I'd expected."
"You don't say, you were not the one to have to hold your load, while gagged in a public place, did you?"
"Well, yeah, but now I'm probably due. We arranged two individual ones, so now it's my turn."

Soon enough they receive a notification and checked the message box.

"Well, here we go. You had to take the initiative, did you?"
"Mine is not so bad, I think. Let's see how it goes."

Challenge number 2:
Jerry has to gag himself with the ball gag, this time with no facemask to cover the gag and cuff himself with cuffs from the bathroom, wrists behind his back. Then John has to insert the cock ring on a mild setting on Jerry, who in turn has to try and finish at least two times while John drives to Redbow Inn, just after mile marker 48 on Interstate 117. You have approximately an hour of driving. Don't forget to put the camera directly in view of Jerry's face and body.

"Creepy, it's good that the rewards are nice. Otherwise, it would not be worth it. Do you think you can manage?"
"Let's see."

Soon enough, we were back to the car. Jerry gagged himself with the red ball gag and cuffed his wrists behind the back.

John awkwardly shoved Jerry in the front seat and lowered his jeans, inserting the ring on his dick.

"How's that? Comfy enough?"
"ITSMGPHJNO OKAYYGHHF"
"Alright, big guy, let's see what you got."

And with that John turned on the mild setting and started off the car, next destination: Redbow Inn.

In about several minutes, Jerry started panting.

"MMMPHHJ MMPPHHHH"

"Okay, the first one is going be quick, apparently."

In a few more minutes, Jerry was struggling and grunting hard. He was just about to have the first tutto finito, when a car passed them by and blew the horn. They'd apparently seen Jerry's gag and we're laughing and making faces, deciding it was a college prank.

That threw Jerry off a bit and he lost his composure. And he was so close....

"MMFJFJFJSJDJ GODMMPGG DAMNHHGJJ"

Don't worry, buddy, we still have time to win the second one, we have about 40-45 min. You can finish two times, right?"

"IWILLPPGHDMM TRYMMPGHH"

As the road was clear and empty up ahead, we were making good speed and I could hear Jerry's panting and breathing getting more and more prolonged. He was getting in the zone.

In about a minute, he started grunting really hard.

"MMPGHHH MMPPHHHH YEMMPPHHHH"

"Alright, here we go, and we have 30 minutes left to spare, we're ahead of schedule."

Time was passing by but so far no second orgasm was happening. Jerry, for his part, was trying, grunting and struggling, sweat glistening off his face, but the setting was too low to bring him to the finish line, it was just serving to frustrate him, if nothing more.

"Jerry, we've got five minutes man, if you don't get one more, we won't win the second challenge and there will be no money for all your trouble. Step it up."

And he was trying. All of a sudden, he had an idea. But he needed John's help.

"JOHNSMMPHH, LOWEMMPHHH MYJJPGG PANTSMMPGGGG, PLEASFFGMMM"

"I'm driving, buddy, but if that's gonna help, let's try. You've got about 4 minutes."

John carefully slid down Jerry's jeans, man, his dick was pressing hard against his boxer shorts. Apparently, this got Jerry going more, as he turned his back to the camera a little and used the friction from the car seat to his dick, he'd found an angle somehow.

Just as they wearing the inn, John could hear Jerry's breathing quicken.

"MMMHHPPP YESMPPHHH IMGGHMMM ALMOSMMGHDHDHD THERMMFHG"

And with one final thrust Jerry finished for the second time, grunting and struggling, panting hard, face all sweaty, getting the pair win number two in challenge number two.

"Okay, just in time, now let's see what's in store for challenge number three. Don't forget, this is the one, where both of us are gonna have to be tied and gagged."

"YEAMMPHHHHH"

And just as they parked in front of the inn, they heard the familiar notification sound of a new text message and exchanged worried glances.