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.

[Red86]

Well the challenges seem to be escalating. But now they are both to be tied and gagged for challenge 3. Is this where it becomes the unfortunate part? Curious to find out!

[squirrel]

Fun chapter, keep it up, man!

[Yaru]

ohhh this looks a the start of a very fun story, plese continue, this is getting good

[harveygasson]

Great second challenge! I wonder what's in store for number three.

[John]

Hey everyone, thank you for the comments, here goes part 3. Constructive criticism or new ideas are definitely encouraged.

We checked into the place. It was a beat-up motel off the highway. A double room was reserved for us and already paid for. At least we would not spend any reward money on stay, which was great. We were given a chance to take a rest and freshen up, before the next challenge. We had a nice dinner and could use the rest. Just before we were finished we heard the dreaded sound. Another notification.

"Finally, this must be the information for the next challenge."

"Hope so, let's see what's in store for us this time. The first two were not as hard as I thought they would be."

The summary read that at 8 AM sharp we were supposed to already be awake, preferably had breakfast (as probably a long day was ahead of us) and had to leave the room unlocked.

We went to sleep and got up early next morning. Took a quick shower and had a nice, little breakfast.

As the hour was getting closer, we started wondering what kind of bondage would we be subjected to this time, especially considering the transaction for this challenge was double what we did last time.

Then we heard another click and a notification read: the next challenge would involve a mock robbery where both of you would get tied for some time. Get ready for the "robber" to arrive."

We also advised to blindfold ourselves. Awkwardly, I placed a tie on John's eyes and then did the same to me, tying it tightly.

Soon enough I could feel the door opening and a hand clamping over my mouth.

"Keep quiet, or else..."

"HELMPHHH MEEKPPG" I grunted meakly, hearing John's grunts from the next bed.

Soon enough, the robbers instructed us to remove our clothing, up to our boxers. Then came the more awkward part's I had to tie John. I took a strip of tape and would it tightly around his wrists and elbows, making sure it was snug. The same process was then used on his knees, ankles and thighs and finally I connected his bound hands to his torso.

By this time, he was pretty immobile and surprisingly enough, was sporting a light boner.

The robbers handed me a pair of tights and instructed me to shove them in his mouth. He accepted with disgust as I shoved them in and kept them in place with several strips of clear tape (this was an explicit instruction by the benefactor, who wanted to see afterwards on the videos that we were stuff gagged).

"MMPPHDJFJ MMMPHHHH"

"Sorry buddy."

John received a hard slap on his bubble butt for his grunting and to check the efficacy of the gag. It was pretty sufficient, as only unintelligible grunts and groans we're escaping his mouth.

Then came my turn. One of the robbers soon followed the same procedure I had used on John. I was rock hard. Getting tied and gagged with one of my best friends was a dream come true and I'd always enjoyed a bit of bondage. Soon enough they gagged me securely with another pair of tights, shoved in my mouth and checked the efficiency of my muffled grunts and by giving me a slight groping.

"MMHPPHH HELPMMHGHH MEEGMMHPP"

"YESMHPPMHH, PLEASMMGHHH"

After we were done, the robbers, as a final touch, put blindfolds on us (the same ties we'd used earlier) and threw us on the bed. A ring signified another message: we had 40 min to get free or the next challenge would be to be carried outside the hotel, in the common pool area, bound, gagged and naked...

[squirrel]

So glad to read part three, the robbery was great! Good job, @John

[harveygasson]

Wow another great challenge and post. I'm not betting on them getting free but you never know I guess.

[John]

Part 4

"HMMMPGJSJD HELMPMMEEHPP"

We were tightly bound and gagged, blindfolded, stripped to our undies and had 40 min to break free. I mean, how would we even manage to achieve this?!

I grunted to Jerry, trying to attract his attention, although I was not sure where he was.

"JERYMMPHHHH, UPHHJKK HERMMPHH, ONMMPHH THEMMPPGHH BEDDMPGH."

"WHERMMPPHH AREEMMPGHK YOUUMMPPHHJ"

ONNMPPHH THEEMMPGH FUCKIMMPHH BEDDDMMPPH"

We grunted back and forth, unintelligible sounds coming out of our stuffed mouths. Finally, I decided to try something. I mean, anything was better than just laying on the bed.

I rolled over to the edge of the bed, slowly shimming down and using it as a support to get up. Then I started hopping. Jerry's grunting was my signal of where presumably he was. With every hop the sounds was drawing closer.

"MMPHHH CAREFUMMPPHH"

Finally, I bumped slightly into the tightly gagged Jerry. He was upright, apparently. We brushed gagged lips and tried to loosen our gags and blindfolds at least a little, but to no avail.

"LETSMMPPHH GOMMPHH DOWNMMGGPP ONMMFHH THEMMPOFH FLOOMMPGH"

I bumped into him a little, just to reinforce my idea, and carefully shimmied down to the carpet. The clock was ticking mercilessly. A few seconds later I could hear a frustrates sigh, followed by a sharp grunt, and Jerry was next to me.

Soon enough, we turned back to back, trying to loosen our wrist and elbow bindings. Several times Jerry's hands were more interested in my ass than the actual loosening of my wrists. I mean, damn, I knew Jerry was gay and on the kinkier side, but we had a job to do.

"MMPHDGHH COMEMMPPHH ONNMMPPHH"

We tried and tried, sweaty and frustrated, grunting and mewling through our stuffed mouths, but no positive result was visible.

At the end, I could feel Jerry's sweat filled face resting next to my thighs. We were a mess, I suppose. Frustrating mounting, unable to articulate properly, we could only await our captors. This was going to be our first unsuccessful challenge since we started yesterday.

Jerry was clearly horny, I could hear his intense grunting as his face brushed my slightly erect dick. I gotta admit, the kinkiness of the situation was getting to me, too.

I intentionally thrust myself and grunted louder, willing to see how Jerry would react.

At that moment, we could hear the motel door opening.

"MMMPPHHH MMHELPMMHHH USMMPHHH"

"Time's up, kinky boys, time for your punishment."

I could feel my boxers were lowered down to my thighs and by Jerry's very frustrated grunting I suppose the same was happening to him.

P.S. As always, thank you for reading. Open to constructive criticism or suggestions on how to improve.

[squirrel]

I;m glad to see that our two protagonists failed their challenge.... Now let's see what the punishment will be

[thespy]

Wow man, great story so far, i like the challenges and I like how erotic it is, can't wait to see what will happen to our kinky boys and what other challenges await them.

[Red86]

It wouldn't be a challenge if it was easy, so the games must go on

[CaptiveDan]

Really enjoying this story! I've been finding myself more into exhibition and voyeurism lately so the 'order fries while he's gagged and edged in the back seat' and the 'drive down the road trying to cum twice while other cars can see you' were both very hot. And of course I love a good rope escape challenge. Very excited for their punishment

[John]

Part 5

"MMPHHHH NOOMMGHHH, HELPMMHHPP MEEHHP, PLEASMPHG, NOUMPH"

Me and Jerry were both grunting hard. I didn't want to be exposed, naked, tied and gagged and paraded around the pool in the hotel but at the same time I found it strangely erotic.

By the sight of Jerry's member, so did he. The robbers had removed the blindfolds from our eyes and now we were due for our punishment.

They forced us to stand upright and started dragging us by our dicks to the outside, we were awkwardly hopping after them.

"NOOPPMHH, NOMMPPHHH, DONTMMPHH DOMMPH THISSMPGH"

Horny, thrashing around, hop by hop, we exited our bedroom. I saw that the manhandling of Jessy was off the charts. He had a bigger butt, so their attention to it was prominent. I heard at least a few hard swats on his backside.

"Okay, here's the situation. You two failed your first challenge but you still have a chance to turn it around. I've been authorized to make a last minute offer which, if done successfully, could save the challenge and consequently, more money will be added to your bank account. What you need to do: you need to hop around to the pool as you are right now, splash down in it, play around and convince someone to untie you. That person shouldn't call the police, you need to convince them that you're two kinky guys, who're playing a game, otherwise you lose the challenge. You have thirty minutes, clock starts running now."

And with a hard slap on our assess, the robber who spoke up gave us some hope.

Me and Jerry shared a tentative glance. We didn't have much choice, we needed to start hopping right away. At least we would get some cardio in. Dicks flapping around, we energetically made our way to the pool. We were both pretty aroused by far. I could see Jerry's butt heaving around, man, he had a spankable one. We finally reached the pool, pretty tired, panting from sweat and exhaustion. We obviously couldn't see the time, but I think we had some time left.

Very carefully, we lowered ourselves in the shallow end, still tied and gagged, as we were.

"Man, what do we have here?? You don't see that every day, two mature guys, buck naked, tied and gagged, entering and splashing around in the pool!? You okay, guys, what's going on, should I call the police?"

Jerry quickly started nodding his head "no", mewling and grunting in the process.

"NOOUMPH, PLEASMPPH DONTMMPHH, ITSMMMPGH AMGH GAMEELPGH."

"I can barely understand you behind that big gag, friend, I think you're saying it's a game, is that so? Nod your heads if I'm correct?"

We both nodded yes. We were pretty lucky so far, we had managed to hop to the pool just in time, splashed around, and now the only thing left was to convince a stranger to untie us. And we'd found one. He looked older than us, around his 50s, you could see he'd been working out in the past, middle height and still a lot of hair on his head, good for him.

"Soo, if this is a game you're playing, bound and gagged naked, in public, it seems like you two are kinky as shit, if I'm not mistaken. You're just begging for someone to find you and play with you, huh?"

"NOOPGHH, PLEASMPHHH FREEMMPHH USSMMPHJH"

"All in due time, my friend, all in due time. Don't worry, eventually I'll untie you. I'm not in the business of kidnapping guys, unfortunately. But first, seeing as you two are sporting some nice boners, I'm gonna have some fun with you."

He entered the pool and grabbed my ass, forcing me closer to Jerry while simultaneously pulling him by his dick.

"NNOOMPFHD PLEASMPHHH"

"Yep, we're gonna have a nice time!"

P.S. What is gonna happen with our two heroes, stay tuned for part 6. Let me know if you want to add something or have some constructive criticism, suggestions, etc. Thank you for reading.

[gaggedrock29]

Lucky bastards!

[Yaru]

heh getting in more kinky troubles each time. excited to see more

[WhereAmI]

Oh wow a swimming pool DICK PULLING contest, is this a trial for the OLYMPICS?