Bondage Summer Blackmail - Encounter 2 - Part 2 added! (M/M)

[Sheriff]

Hi all. This story revolves around an unfortunate situation that 18 year old Cam gets into with his male neighbour (and maybe eventually his wife).

There's a big focus on female feet, forced male bondage and sexual contact and a theme of poor Cam being made to have cum in his mouth.

Obviously this is all fantasy and not an advocation for this kind of behaviour. If this sounds fun then dive in!

****

Cam was having an incredible day. Yesterday had been his last ever day at school tand he was relaxing at a garden party held by his neighbors. The hot summer sun and the garden in turn meant a lot of bare feet which he was taking full advantage of. He’d filled his camera roll with candid snaps of bare, sweaty feet, especially those of his neighbour, Steph. She had dark, curly hair and was in her late thirties, with a dancer’s figure and beautiful, delicate feet. He’d also managed to sneak inside a couple of times to take a sniff of her shoes by the door (heavenly strong and with clear toe prints on the inside) and had even managed to swipe a pair of her worn socks from the hamper. Bliss.

The only slight hiccup had been Tom, Steph’s husband. Whenever Cam had been trying to enjoy some surreptitious photo taking or sneak inside, he’d been there. Hovering. He was nice enough, but it had made not getting caught a living nightmare. It had been worth dodging him though. He’d taken enough photos to fill his wank bank for the whole summer until he got to uni. But as Cam lay in bed that night, sifting through the photos and burying his face into the stolen socks, he couldn’t shake the feeling of something being wrong.

*****

The next day when Cam came downstairs at around 11 his mom yelled through to him.
“Morning, honey. When you’ve had your breakfast do you mind going next door? Tom popped by and asked for your help with something.”
Cam raised an eyebrow, a brief stab of panic in his stomach. It was odd but not completely implausible. There’d been some diy? Or something with the garden? It was probably fine, and might give him some more time with Steph’s shoes if Tom went to the bathroom at all.
“Sure, mom,” he called back.

Some toast and some clothes later and Cam was knocking on the neighbours’ door, trying to keep his nerves steady. The door opened and there stood Tom. He was tall and about the same age as Steph, but with short grey hair and a sprinkling of stubble.
“Hey, Cam. Good to see you, come on in and grab a seat in the living room. Want a beer?”
“Errr, sure?”
A little confused, Cam headed to the living room and slumped onto the sofa. He noticed Tom’s laptop, plugged into the tv by a long cable, a screensaver playing in 50” glory, and something else that made his stomach flip. On the coffee table were Steph’s flats that had been next to the door that Cam had taken advantage of. Beside them were a pair of light blue socks that he often saw Steph running in. Even from the sofa he could see the damp stains from fresh wear.

A moment later Tom walked in, smiling, and pressed an open beer into Cam’s hand.
“She has great feet, doesn’t she? Great smell too,” grinned Tom, sinking into the seat beside the laptop.
“Errr, I dunno what you mean,” mumbled Cam, face flushing.
“Look, nothing to be embarrassed about. You’re eighteen, she’s the hot neighbour. I’m not mad, I get it. And I saw your little escapades yesterday.”
“I think you have the wrong idea, I should go,” Cam managed to choke out.
“Just hold on a sec,” said Tom, reaching for his laptop.
A second later the tv screen flickered to life, with Cam on screen. A short video played, depicting three scenes one after another. Cam on his phone, a clear image of Steph’s feet in the camera app on screen, then him picking up her shoes and inhaling deeply and finally him pocketing some socks from the hamper outside the bedroom.

His heart sank.
“Fuck.”
“Yeah, you got a bit overeager, champ.”
“Are you gonna tell anyone?”
Tom paused and took a long sip of beer.
“You know. I should. I should probably tell Steph, your parents and honestly all the women at the party who’s feet you photo’d.”
Cam’s heart dropped though the floor.
“But…” he continued, “That doesn’t seem fair on you. I think we should keep this quiet and I’ll work out a punishment for you. How does that sound?”
Relief washed over Cam.
“Oh my god, yes, thank you. Honestly I’ll do anything.”
Tom’s smile widened and he reached to the side of his chair to grab a bag that he emptied onto the table.

A pile of rope, some tape….and a collar.
“What’s that for?” gulped Cam.
“Your punishment.”
“You’re going to tie me up?”
Tom nodded
“It seemed fitting. It’ll give you time to reflect and it’s somewhat….humiliating.”
Too humiliating as far as Cam was concerned.
“This is too weird, I’m gonna…”
Tom simply held up his phone, Steph’s contact on screen and his thumb over the dial button. Cam stopped, then sighed and sat back down.
“Now, partly cus it’s a hell of a hot day and partly because of the disobedience we’re gonna do this in your underwear now.”

Cam had learned his lesson and sullenly kicked off his shoes and peeled off his t-shirt. He hesitated at his jeans but kept going until he was standing awkwardly in his boxers.
“Good choice, now turn around and put your hands behind your back.”
Sullenly, he complied and moments later felt strong, rough hands maneuver him into the proper position, followed by the first touch of rope.
“So, did you enjoy those socks you stole? Might as well be honest.”
“Yeah,” muttered Cam in response, “I think she’d been wearing them that day.”
“Oh champ, she’d only worn them a few hours. That pair is gonna be nothing compared to the ones on the table. She wore them for a run, to work and then another run this morning. They will blow your mind.”
Cam didn’t know what to make of that but the thought of those socks made his cock begin to stiffen as Tom pulled the rope at his wrists tight, further adding to his humiliation. He didn’t even need to struggle to realise he was already well and truly helpless. Completely at the older man’s mercy.
Next came his elbows, proving Cam to be surprisingly flexible as they were pulled almost touching.
“So obviously you like feet. What else you into?”
Here we go. Not that this was even remotely how he’d pictured his fantasy though.
“Bondage,” snorted Cam, the irony stinging him.
“Ha, I’m guessing you always pictured Steph though?”
“Yeah,” grunted Cam as his elbows were cinched tight.
“What did you picture? Remember, better to be honest.”
Cam tried to shrug but was unable. Rope got passed in front of him as Tom began to harness his chest.

“Errr, varied. Sometimes I’d imagine her tied up after a run and having my way with her feet, shoving her socks in her mouth. Sometimes I’d picture that she’d caught me stealing her socks and tie me up to punish me.”
Cam was flushing heavily at being forced to admit his deepest fantasies, and even worse that talking about them was just making him harder. Thankfully Tom hadn’t seemed to notice.
“Ah, so near yet so far for you. I’m guessing you’re not into guys?”
Cam shook his head.
“That’s a real shame for you.”
Cam gulped.

The next two minutes passed in silence while Tom secured the harness. He manhandled Cam round to admire his handiwork, nodding to himself in approval. His eyes drifted downwards.
“What have we got here?”
Before Cam could do anything about it, he’d stepped forward and whipped Cam’s boxers down to his ankles, revealing an almost completely erect penis. Cam went even redder and his eyes dropped to the floor in shame.
“Those socks and flats are driving you crazy, huh? Tell you what, let’s give you a treat.”
He leaned and grabbed one of the socks and held it up to Cam’s face, over his nose.
Reflexively he inhaled deeply and pressed his face into the sock and Tom’s hand. They were still damp from her run and the scent was incredible, almost overpowering. A high pitched moan escaped his lips and he was painfully aware of his now throbbing erection.
“Open your mouth, slut,” ordered Tom.
Without thinking Cam opened wide and the worn sock was shoved deep inside, the flavour exploding across his tongue as Tom’s fingers packed it firmly into his mouth. While Cam recovered from the shock, Tom grabbed the roll of duct tape and begin wrapping it round Cam’s head, welding his lips shut with the sock inside

Cam whimpered through his gag but Tom ignored him, instead dropping to his knees with some more rope to begin immobilising Cam’s legs. Cam couldn’t bring himself to look as rope lashed his ankles, then knees and then thighs together, but he was painfully aware at his erect cock brushing tom’s hair and what at one point felt like hot breath on it.
“Right, couple more things then we’re good to go,” he said, pulling some string from his pocket, “don’t want you to finish all over the sofa.”
“Mmmmphh?” mumbleds Cam into the sock in confusion. He definitely felt close to the edge thanks to the sock but how was…
The question was immediately answered as the string began wrapping tightly round his shaft and balls.
He whimpered and shook his head pitifully in helpless protest. Tom just grinned and pulled the string tight.
“That should solve the cumming. Now, lie face down on the sofa.”

It was tricky, but he managed to sit down then flump onto his side and then awkwardly roll over onto his front. No sooner was he in position than Tom had grabbed his legs and pulled them towards his elbows and into a crazy tight hogtie. His feet were placed gently together and more string found its way between his big toes. He gave an involuntary giggle as his feet twitched at the sensation. Shit. he hadn’t thought of that. Surely Tom wasn’t going to tickle his feet?
“That doesn’t bode well for you, champ.”
Fuck. It wouldn’t just be absolute torture, it’d be humiliating beyond belief as well, writhing helplessly under another man’s fingers.

Tom stood back a final time and looked Cam up and down, taking in the helplessly bound, naked young man.
“So obviously you need some punishment but I'm going to give you a fighting chance. I have a work call I need to take that should be about 45 minutes. If you can get out in that time, then we’re square, and I’ll even let you come over while Steph is at work and help yourself to her shoes and socks. But if you can’t get out, you’re mine. I’m gonna torture the shit out of you and for the rest of the summer, any time I feel like it you have to come over and let me do whatever I want to you. And if you were thinking about refusing, this whole thing is being videoed, which would be very embarrassing for you. Now, get struggling.”

Cam deflated. He was going to try, try like his life depended on it, but he knew there was no way in hell he was getting free.
He started pulling desperately at his bindings, bucking and tugging desperately to somehow pull his way free. After ten minutes of fruitless struggling he was utterly exhausted, not a single rope had budged and if anything some were tighter.
Ok, time to be sensible. He switched from his useless tugging to instead questing for the knots with his fingers, trying to find the ends of the ropes. Nothing. He was well and truly fucked. After ten minutes more he decided to just lie and wait for the inevitable. A summer of humiliation, slavery and torture.

[Jaaaake]

Really fun story. Looking forward to the next part.

[Red86]

Looks like Cam got himself into a pickle. But it can't all be bad, he admitted he likes bondage. If anything, he may end up enjoying his summer more then he thinks. Or maybe not. I guess we'll have to wait and see!

[Sheriff]

Hi @Jaaaake thanks so much

@Red86 There's going to be a mix of slowly enjoying it more and some unexpected treats alongside some fairly brutal torture XD

[jone123]

Thats a fun story, has so many interesting component.

Thanks for sharing, I truly looking forward to more and I cant wait to see how will you get steph into this arrangment haha.

to be dominated by a couple is such a sexy thought

[fratboydanny]

A very enjoyable read @Sheriff. i too hope our hero discovers things about himself he never thought possible. Looking forward to the balance of summer!

[Sheriff]

@jone123 and @fratboydanny

Thank you both so much! I'll be putting up the second half soon and I'll get writing the next encounter. Steph is ABSOLUTELY going to start being involved but I thik it'll be several encounters in before it happens

[Sheriff]

Tom had a smug smile on his face when he walked back in and saw Cam exactly as he’d left him. Hogtied, ropes at his wrists, ankles, knees, elbows and chest. His toes tied together, gagged with Steph’s well worn sock, completely naked and perhaps worst of all a makeshift cockring from string tied round his cock and balls.
“No luck, eh?”
Cam shook his head pitifully.
“Completely helpless?”
Cam nodded and mmmphed into the sock. The one good part of the whole experience.
“Well, obviously now I’m going to torture you. And I think I’m going to start by tickling your feet.”
Cam shook his head and pleaded into the gag, not that he thought it would do any good.
“First though, a little treat.”
Tom grabbed Steph’s sweaty leather ballet flat from where he’d left it on the table and pressed it against Cam’s face, forcing his nose right into the toe section. The captive Cam was forced to breath in through his nose thanks to the gag and did so appreciatively, savouring the strength of the scent.Tape ripped from the roll and passed over the shoe and around Cam’s head a few times, fixing it securely in place.
“Good?”
Cam nodded despite himself.
“Let’s get started then.”

Cam jolted when he felt rough fingers on the soles of his feet, gently caressing up and down. Tom wasn’t even trying to tickle yet and they were sensitive as fuck.
“Fuck me, you’re even more ticklish than Steph! Fantastic.”
Cam whimpered and then attempted to shriek as a nail stroked from his heel up to his toes and in between them. He sucked in a lungful of air directly from the shoe as he fought to get away from the torturous touch of his captor.
“And that was just one finger, let’s up this a bit…”
Cam screamed into the sock and tape as ten fingers began assaulting his feet, spidering over his soles, heels, toes and even the tops. He was tied up so tightly and securely though his attempts at thrashing barely moved him an inch. With his toes tied, all he could realistically do was flex his feet slightly which did nothing to protect him. Even worse, the slight movements he could make were rubbing his cock against the sofa, which coupled with the shoe and his gag was making him rock hard. An utterly humiliating position for him while he was tied up naked at the hands of his older, male neighbour.

After a minute Cam’s face was soaked with tears of laughter. After five minutes he’d lost the energy to struggle though the tickling was just as awful. Throughout, Tom had been playfully taunting him and making idle threats if Cam were to tap out (not that he could). These ranged from showing the video of him tied up and naked to everyone, walking him into the town square bound in heels and lingerie and even being made to orally pleasure his captor, and as the time hit the ten minute mark he couldn’t say for certain that he wouldn’t joyfully accept ANY of the threats. In fact some public humiliation or a mouthful of cock currently seemed decidedly preferable.
“Right, you can have a short break then I’ll crack out the baby oil for a final five minutes.”
Cam weakly shook his head and begged no but was ignored.
The break passed like lightning.
The click of the baby oil lid echoed through the room and warm, smooth oil dripped onto Cam’s bound feet, flowing liberally between his toes and down his soles.
“Tied up, gagged, oiled up, naked and…” Tom rolled Cam to the side briefly, “yup, still rock hard. Bet you must be feeling pretty humiliated. Regretting stealing those socks now?”
Tom started massaging the oil into his helpless captive’s feet as Cam whimpered his remorse.

Then it began again. The sensation of the oil being rubbed in had heightened the sensitivity while also allowing the tickling fingers to glide easily and mercilessly over his feet, sending him into renewed thrashing and screaming. Five minutes of utter hell asTom lazily slid his fingers over every inch of Cam’s feet. The main focus was on his toes, which proved to be by far the worse, but he always made sure to have his other hand working a separate spot to heighten the torture. Every second crawled by.

Eventually though, the tickling ceased, leaving Cam quivering, face soaked in tears of laughter. He barely even noticed, let alone resisted as Tom undid the hogtie and sat him upright. He didn’t even care when a collar was fastened round his neck and a rope attached. He only dimly seemed to realise the change of predicament when the rope to the collar was tied tightly to something behind the sofa, followed swiftly by a rope attached to ankles, pinning him immobile to the couch. Tom grabbed his laptop and sat incredibly close, their thighs touching.
“Let’s watch something together, bit of bondage bonding.”
Cam just breathed, enjoying the lack of torture and the scent of the shoe that somehow was still strong.
A few moments later his cock, which had been starting to soften, jerked back to attention as onto the tv screen came a video of Steph. She was in her underwear, hogtied helplessly on the sofa exactly as Cam had been, ropes digging into her skin so tight she could barely move. A huge ballgag was in her mouth and as Cam gazed wide-eyed, Tom walked onto screen holding one of her pink running shoes. Steph began to struggle and mmph furiously as Tom pressed the opening to her nose then grabbed some duct tape that he used to wrap it tightly to her face.

“She’d just finished a run as well so those shoes reeked.”
He moaned involuntarily and Tom seemed to notice that Cam’s cock was once again straining at the string he’d bound it with. As he watched the Tom on screen begin tickling Steph’s feet he couldn’t believe how ridiculously turned on he was, even despite his humiliating captivity.
“Let’s get that for you champ,’ said Tom, fingers moving to untie the string.

The brushes of Tom’s fingers against Cam’s rock-hard dick felt incredible, to Cam’s shame, as did the relief when the string loosened. Afterwards though, the hand stayed where it was, fingers stroking lightly. He was so tired, turned on, humiliated and helpless that he didn’t even bother to fight it. He couldn’t even stop himself from moaning or trying to grind forward into the waiting fingers.
“That feel good, slut?” laughed Tom.
Cam’s faced burned with sudden shame and he tried unsuccessfully to pull away.
Tom just laughed and grabbed Cam’s helpless penis with his whole hand and began stroking slowly but forcefully.
“Don’t worry about it, dicks have a mind of their own. You can’t help that it feels good, and seeing Steph like this has got you all riled. Plus you’re tied up and helpless. Might as well enjoy it seeing as you don’t have a choice.”
Cam let out a deep sigh and sat back, allowing Tom to continue masturbating him. He was right, he was utterly helpless and the hardest he’d ever been in his life. Even after resigning himself to enjoying it, he was determined not to finish but when the Tom on screen started sucking Steph’s toes it was just too much.
His breath came in ragged, shuddering gasps and in a flash Tom had popped the remaining sock over his dick to catch everything as Cam came harder than he’d ever came in his life. The orgasm seemed to go on forever as he poured into the sock, utterly soaking it. It rocked his entire body and had him straining against the collar until he eventually collapsed back, spent.

“Wow, impressive, helluva load. That feel good?”
Cam nodded weakly.
“Surprised you came?”
Another nod.
Tom grinned.
“To be honest, having you like this has turned me on a bit too.”

With that, he unzipped his fly and brought out his dick and began to jerk himself off. Frankly it was monstrous and the thought that he might end up with it in his mouth kind’ve terrified Cam. Or it would have if he wasn’t so exhausted. He just sat back, barely noticing as Tom finished onto the already cum-soaked sock. He didn’t even open his eyes as the shoe was untapped from his face and his gag slowly removed. He was just grateful everything was finally at an end. For today at least.

The sock was tugged from his mouth.
“Oh thank go…mmmphh!”
Another sock was shoved in and pressed down into his tongue, rubbing back and forth. The taste and sensation of salty, gelatinous liquid exploded across his tongue, making him gag with the strength of it. He tried to thrash and spit it out but Tom’s strong hands held him down and wrapped layer after layer of tape over his lips, sealing the cum soaked sock firmly in his mouth. He tried to scream but it just pressed his tongue harder into the fabric, intensifying the taste as the cum spread through his mouth. He quickly fell back, sullen, humiliated and defeated.
“Can’t treat you too much, I am meant to be punishing you for what you did. You like the taste of my cum in your mouth, Cam?”
He glared at Tom and shook his head.
“Well I’d get used to it, cus it’s gonna be in your mouth a hell of a lot. Now, you sit there and think about what you did while you suck that sock clean. I’ll untie you in an hour or so.”

And that was that. Cam had no way of escaping, so he just had to sit there, dreading every time he had to swallow another load from the sock. After an hour and a half and another, spontaneous, forced handjob later (where again, to his shame, he came hard) Tom finally let him go.

“I’ve got your number so I’ll text you next time I decide to tie you up. In the meantime, if you wanna come over in the day when Steph’s at work to have some fun with her shoes or socks, or if you wanna see any more videos of her then you’re welcome any time.”
“What, so you can just tie me up again?” snapped Cam.
“Champ, when I want you tied up, you’re getting tied up. You being here isn’t gonna change things. Might as well get your rocks off. Anyway, take this,” Tom handed Cam a carrier bag, “I’ll text you what to do with it.”

And with that Cam staggered into the sun, with a whole summer of torture ahead of him.

[Red86]

Cam thought it was over, only to have the gag replaced. He's finding out the definition of it isn't truly bondage until you want out and can't get out

Interesting to learn he's done similar with Steph. Explains how he's so good/confident in tying someone!

[Sheriff]

@Red86 Absolutely agree! I think personally, the change of gag more than anything else was the point where he knew he was in really deep trouble XD

Steph is frequently on the recieving end of everything Cam will be going through and later in the series she'll begin to join in, sometimes as a victim of Cam, sometimes with him and sometimes tying him.

I really need to get on and start writing the next chapter!

[burro22]

Amazing two parts so far! I'd kill to be Cam. I love the idea of being gagged with Steph's worn socks and then gagged with a cum soaked one next. Great writing, thanks!

[60Cancer]

I can't wait for more.

[Boundguy800]

Excellent story. I love the unique storyline and the extra tie and punishment at the end of part II.

[DuctTapedBoy22]

Great story, can't wait to hear more from you.

[dallen108]

Love it. Can’t wait to read more. I love the humiliation of a cum sock gag.

[harveygasson]

Holy cow that was a brilliant story!

[Snozzberry]

Great story. After chapter 1 I have a feeling Cam is going to have a longgggggg summer being Tom's Bondage Boy Toy almost every day.

🖐🖐

[Sheriff]

Hey all, thanks so much for the lovely comments. Been a busy few months but Encounter 2 is almost ready!

@dallen108 Thanks and agreed! It's not just torture to taste but humiliating as well. Honestly a bit of a recent fantasy of mine!

@Snozzberry Thanks! And you are absolutely, 100% right!

[60Cancer]

How about an episode where Tom "kidnaps" Cam.

[ATOne]

Loving this! Wonder if Cam will have to give up one of his pals to keep Tom occupied, and if Steph’s had her eye out for a kinky little slut boy too?!

[jake22153]

Mmm…hot!

[Sheriff]

Sorry for the delay, here's Encounter 2 Part 1, next bit coming very shortly!

Cam grimaced as he rubbed moisturising cream into his extremely sensitive feet. It had been three days since his torture and humiliation at the hands of his older neighbour, Tom. When he closed his eyes he could feel the ropes holding him helpless and taste the cum soaked sock that had been forced into his mouth. He shuddered at the memory. He could also, very vividly, remember the tickling his feet had endured. Which made this all the worse.

With blackmail videos of Cam stealing Steph’s socks (Tom’s wife), and of course videos of him bound and naked, Tom was blackmailing Cam into being his bondage slave for the summer. He was also forcing Cam, twice daily, to moisturise his feet to make them even more sensitive for future tickling. The thought terrified Cam. The last time had been utter torture and now his feet were so sensitive he could barely touch them himself.

Touching himself. That was a humiliating memory too, as Tom had jacked him off to completion against his will, and it had felt far better than he was proud to admit to himself.

His ruminating was interrupted by a ding from his phone. He wiped his feet down and walked over to grab it. Shit, it was from Tom.

“I’ve got a few hours free so head right over.”

Cam’s heart fell. Well, there wasn’t much for it. He gingerly pulled on his socks and headed for the door. A minute later he was knocking at his neighbour’s.

The door opened and Tom smiled out at him.
“Hey Cam, good to see you, come on in.”
Cam frowned but trudged inside, heading in the direction Tom indicated, toward the stairs. The door clicked close and the lock turned shut.
“First left at the top of the stairs.”
Cam jogged up as instructed and opened the door to what appeared to be the master bedroom. It was large and nicely furnished, with a rustic, king sized four poster bed in the centre. Ropes were tightly tied to all four corners.
Footsteps sounded from behind him.

“I see you found today’s activity. You know the drill, strip naked.”
Cam didn’t even bother to argue. Tom had shown he wasn’t kidding around with that sort of thing. He pulled off his t-shirt, then his shoes and socks, trousers and finally his underwear. The whole lot were dumped into the corner. He didn’t even have time to start feeling embarrassed before the next order came.
“On the bed, spread-eagled with your feet right at the bottom.”
Cam gulped. He was going to be incredibly vulnerable and exposed, even more so than the last time. He hesitated.
“The longer it takes the worse it’ll be,” Tom informed him.
With a sigh he climbed into the bed and lay back, spreading his limbs wide.

Seconds later Tom began knotting the rope round Cam’s right wrist.
“Have you been moisturising your feet?”
Cam nodded.
“Yeah.”
“Fantastic. They feeling more sensitive?”
“Just a bit.”
“Ha! I’ve had to start tying Steph up to massage her feet she’s so ticklish. We’ll see just how bad it’s gotten for you.”

The knot was pulled tight and he started on Cam’s left wrist.
“Why are you doing this? All of this.”
“Hmm? Oh. Well I enjoy tying people up, torturing and humiliating them, and you gave me the perfect opportunity. It’s a bit of an extra turn on for me that you’re so unwilling and don’t have a choice. Just couldn’t pass up the chance and I’m gonna make the most of it while I can.”
Well, it made sense he guessed.

With his victim’s hands bound, he moved down to Cam’s feet , grabbed him by the ankles and tugged him down the bed, pulling his arms taught. He began on his left ankle.
“Least you got a nice handjob out of it last time. Not to mention a real closeup encounter with Steph’s footwear. You know I’m surprised you haven’t stopped round to have another go with them.”
“So you can tie me up again for it. No thanks. And the handjob was a fluke, cus of the all the videos of Steph and her socks.”
“If I want to tie you up then you’re getting tied up, whether you come over or not. Make the most of the opportunity. And a fluke? Oh really? Care to make a bet?”
Onto the final ankle.
“What kind of bet?”
“Well. Steph has an overnight work trip on Thursday. I was planning to have you over for the afternoon after she left. If you win, you don’t have to come over. If you lose though, you have to stay over until the next morning. My prisoner overnight.”

Cam considered the proposal while his final limb was bound tight.
“How do I win exactly?”
“You win by not cumming. I won't cheat by showing you videos of Steph or bringing her shoes and socks anywhere near you. If I can make you finish though, you lose.”
It was tempting. Cam was nervous at the prospect of a whole night at Tom’s mercy, but he was convinced he wouldn’t finish. It wasn’t like he’d enjoyed the handjob, or any of it. It was just how turned on the other stuff had made him..

“Deal.”
“Fantastic, I love a challenge. Now, struggle for me.”
Obediently, Cam began to pull and tug at the ropes pulling his limbs to the corners of the bed. Not even an inch of give.
“Pretty helpless?”
Cam nodded.
“Yeah.”
“Say it.”
“I’m helpless, Tom,” sighed Cam.
Tom gave a big grin.

[WhereAmI]

With the bets Cam makes it don't think I'll be taking him to the Horse track with me. Looks like Cam will be having an all nighter with Tom shortly. POOR Cam.

[Red86]

Ha, I don't think Cam realizes what predicament he's getting set up for. It's unlikely he'll win. But that's okay, more entertainment for us

[Sheriff]

“Say it.”
“I’m helpless, Tom,” sighed Cam.
Tom gave a big grin.

“Steph’s the same. She can barely move when I have her like this. Can’t pull away when I tickle her feet or suck her toes…”
Cam’s cock began to stir at the thought of it. Shit! He hadn’t thought of that, it wasn’t breaking the rules but it was going to make the challenge a lot trickier.
“Not that she fights me sucking her toes, she loves that. You know, if she came in and found you like this it’s probably the first thing she’d do. Shove her hot sweaty toes in your mouth. And you already know how they’d taste.”
His dick shot to attention.

“Too easy,” snorted Tom, grabbing something from the nightstand. It was a small pair of connected black rings with a rounded cylinder between them. He stretched them wide and slipped them over the helpless young man’s cock and balls, one at the base of his shaft and another at the top of his testicles. A second later they buzzed to life with a humming vibration.
“Hey, what the fuck?! That’s cheating.”
“No it isn’t. I just said I’d keep Steph’s footwear and videos out of it. I didn’t say I wouldn’t use toys. This is just to keep you on the boil.”
“It’s still horseshit,” muttered Cam.
“Tell you what, Champ. Double or nothing. I won’t use any toys, just my hands. But if you still cum then you suck my dick, here and now.”
Cam froze, his confidence evaporating. He said nothing.
“That’s what I thought. Now, open up, cus you’re gonna need to be gagged for the next bit.”
Obediently, Cam opened his mouth wide so Tom could pack a piece of white cloth into it. It was larger than he thought and by the time he was finished Cam’s cheeks were bulging. To hold it in, Tom used a large ring gag forced into his captive’s mouth and buckled tight behind his head.

“Scream for me.”
Cam screamed at the top of his lungs. Barely any sound came out and a grin spread wide over Tom’s face. He started stroking his fingers over the bound teenager’s chest.
“I think you like this or you’d be louder. Come on, really scream for me to stop.”
He gave it his all but nothing came of it.
“Perfect. Honestly I’m hard just thinking what I could do to you right now, and I think I’m going to take advantage of your feet.”
Cam braced himself for tickling but instead he felt something hot and wet on his heel, sliding up toward his toes. Tom was licking his feet. It sent a spike of shame and humiliation through Cam, but even worse was that it felt amazing. The sensation on his sensitive feet was overpowering and he whimpered helplessly into his gag as his captor did to him what he wanted to do to Steph.

After several minutes of this Tom stood up and looked down at his captive.
“Ok, we’re gonna do another little challenge before we try and jack you off. I’m gonna tickle your feet, for the next hour.”
Cam yelled into his gag and shook his head vigorously. Tom waited for the outburst to subside then continued.
“Every ten minutes I’m going to give you the opportunity to give up. If you do there’ll be a severe punishment, probably involving some cum, but no more tickling. Understand?”
Cam squeezed his eyes shut and nodded pathetically.

Tom dove straight into, raking his nails up Cam’s soles. It was so much worse than it had been a few days before. His fingers danced all over his soles, heels, between his toes, over the tops, over and over, sending Cam almost into convulsions as he strained and screamed into his gag. His feet were unbelievably sensitive and tears were soon rolling down his cheeks. By the time the ten minute mark was reached and Tom let up, Cam’s muscles ached from thrashing.

“Ok, first slot down. Wanna give up and accept your punishment?”
Cam thought for a moment but shook his head. The taste and humiliation of that cum drenched sock still haunted him.
“Perfect, I wanted more than ten minutes with them. Now, let’s get some oil. That always drives Steph wild.”
A few seconds later Cam felt liquid dripping between his toes and down his soles. Even it gently being rubbed in was too much. Even before the second round started he knew he was going to end up with cum in his mouth, but first, he had ten minutes of hell to endure.
He begged and pleaded through floods of tears as Tom worked his way over his feet, taking complete advantage of the way the oil let his fingers slide over his sensitive, helpless feet.
It seemed to go on forever, and by the end, he was absolutely exhausted, too tired to even struggle. Eventually though, it did come to an end.

Tom stood above him, smiling wryly.
“Want more tickling?”
Cam shook his head.
“Want your punishment?”
He nodded.
“Good boy. First though, you’ve been rock hard for ages, let’s get that sorted.”

Tom sat on the bed and moved to release Cam’s cock and balls from their buzzing prison. Cam had been struggling to contain himself with just the vibrations, but with the cock ring off and Tom’s oiled fingers starting their work he knew it was just a matter of time. It wasn’t even worth trying to fight, he simply lay back and closed his eyes.
“Decided to just enjoy it?”
Cam’s face virtually caught fire but he nodded.
“Best thing for it, Champ. I want to hate some of it but I’d like you to enjoy bits of it. Tell you what, want to admit that you’re going to cum and enjoy one of Steph’s heels while you do?”
He nodded.
The shamefully delicious stroking stopped for a minute while Tom went to the wardrobe and retrieved a battered looking pair of heels. He balanced one over Cam’s nose, instantly transporting him to heaven. He heard Tom taking a sniff of the other as he resumed jacking off his prisoner.

“Her feet smell great don’t they?”
Cam moaned in ecstasy, melting and hardening under Tom’s fingers.
Tom must have sensed the change because he had a cloth ready when his captive exploded. He stroked some more, milking the last remnants out before standing up and walking to stand above Cam’s head.
The shoe was removed and the cloth in his mouth pulled out through the ring gag.
“Well you’re going to be my prisoner overnight cus you came. Now time to pay the piper for wussing out of the tickling. Obviously if you turn your head away I’ll have to come up with something much, much worse.”
Cam whimpered in realization as Tom unzipped and pulled out his colossal, erect cock. He began to stroke up and down, the tip aimed directly at Cam’s gagged, open mouth.
Faster and faster it went until the orgasm exploded out, coating Cam’s face and worse, his mouth, with a hot blast of salty cum.
“Mmmm, that really, really good,” he sighed, wiping the tip unceremoniously on Cam’s cheek, “you enjoy the taste of that for a while. The gag’ll make it hard to swallow so it might just have to sit on your tongue for a while.”

This was even more humiliating than before. He could taste, smell and feel it on him and moving his tongue just made it worse. Even worse, it came right after one of the best handjobs and orgasms of his life.
“I’ll be back in an hour to finish you off again and do some more tickling, then we watch the video together and plan your overnight stay.”

Shit.