Naruto Shippuden: Once a gambler always a gambler

In a small land that borders the land of Fire walked Tsunade and her apprentice Sakura, who was nearing the end of her training. With word that Jiraiya and Naruto were due to come home soon, Tsunade decided now was a good time to rest up and be ready for their arrival.

"Master, I don't think this is a wise choice..." Sakura said as Tsunade was giddy, having received her bonus for working hard as Hokage left her with an itch that could only be scratched in one way.

"Oh shut it Sakura! I need a good time, and this is the best place for it!" Tsunade happily said.

"Only because this place is most likely the one of the few to not having you on a gambling ban list..." Sakura dryly remarked.

"Hmph, Shizune can get me on as many ban lists as she wants, I'll find one place that will take my money!" Tsunade grinned happily.

"Oh Master..." Sakura sighed as she had woke up earlier in the morning to a drugged cloth placed over her mouth, placing her into a deeper sleep only to wake up on the road with Tsunade with a messy packed bag of their items. "I would force Master back to the village, but I haven't become stronger than her yet, and trying to send a message will just make things worse, guess I can only keep an eye on her..." Sakura thought feeling like she had it worse, unaware that Naruto had to constantly drag his drunken master back to bed every night while Sasuke had to constantly fend off death strikes from his master.

"Go ahead to the inn Sakura, I'll get the night going in style!" Tsunade cheered walking off as Sakura shook her head and found themselves a nice inn to most likely lament in being broke.

--- some hours later---

"I was sure she didn't have much money to start with, how long does it take to lose it? Unless she is actually winning for once?" Sakura sighed deciding to check it out as she put her shin guards and heel shoes back on, while checking her long hair in the mirror. "I’ve been so busy I haven't had time to get it cut, need to fix that soon..." she muttered thinking how Naruto liked her shorter hair.

"Now, where is she?" Sakura muttered walking through town, as she asked the locals about Tsunade, which it didn't take much to track down the large breasted Hokage to a back-alley gambling hall. "Oh great, the back-alley ones are always the worst..." Sakura sighed heading down the alley and entered the gambling hall, what she saw made her gasp.

"Lady Tsunade!" she cried out to see a frustrated Tsunade sitting before a dice game, the only thing cladding her was a pair of skimpy green panties as everything else was out to see for the men in the gambling hall.

"Sakura! I told you to stay at the inn!" she cried out as Sakura moved forward, however some fast moving ninja got behind her, before she knew it her arms were pulled and locked into arm behinds behind her back. While a wide green dildo panel gag was forced into her mouth, making her sputter and gag on it roughly as the dildo part of the gag went all the way to the back of her throat. The straps of the gag wrapped upward to wrap around her eyes to blindfold her which all the straps ran into a spinner that was placed behind her head, locking the straps tightly into place.

Gif pic by dawho555 of DeviantART

"MRMRRPMRM!" Sakura cried out as she was forced to her knees, the special latex bindings that restrained her arms along with the green dildo filling her mouth sapped her of her chakra as shackles were placed around her ankles. “What the hell is going on?! What did master bet this time? Me?!”

"Heheheh, that's one payment, oh Hokage..." the men of the haul grinned at Tsunade who glared, having already bet most of her modesty, money and now Sakura.

"Mrmrprh ghghg mrmrphrpm!" Sakura cried out confused, recalling a tale of the Land of Wind from Shizune who was in the same spot once before.

"It's the Sand all over again..." Tsunade groaned with a cold sweat covering her body.

"Well, panties or not, Hokage?" the gambler asked in a mocking tone.

"Fine! For Sakura back I bet them!" Tsunade said as the men chuckled, soon throwing the dice into the bowl and slammed it down, coming up odd on Tsunade's even bet. "N-No..." Tsunade gasped.

"Mrprm?!" Sakura squeaked out fearfully.

"Heheh, your panties Hokage..." the men asked as Tsunade shut her eyes in humiliation as she soon pulled her panties away, revealing her pussy for all to see.

"Hahahahahahh!" all the men laughed in perverted victory as the gambler walked forward.

"Very lovely! But we allowed you to double down on that bet despite one article of clothing, how do you intend to pay off the rest?" he asked as Tsunade knew she had to draw on funds from the village.

"I'll contact my office and-" she began to say before the man got in her face.

"Oh no, we won't let you contact a military office, we're not stupid! But we're good men here, we have another way for you to pay...." he smirked as Tsunade frowned as she was soon taken away with Sakura led to a comfy barn to wait to see if Tsunade could pay off her massive 1,000,000 yen debt.

----------

"We'll relax here for the day Naruto before returning home," Jiraiya told Naruto who gave his master a flat look.

"You just want to stop here because you can get some cheap action pervy sage!" Naruto declared as Jiraiya grinned wildly.

"Heheheh, so what? You go get a hotel room and I'll be back later!" he said waving his student goodbye who glared at Jiraiya.

"I'm not carrying you home anymore you stinking drunk!" Naruto shouted out before sighing and headed towards the inn which as he did, he came into contact with a cute raven hair girl clad in purple and black clothing.

"Hey there brighty, care for a moment?" she asked Naruto in a seductive tone while giving him a cute wink.

"Huh? Me?" he asked.

"Yeah, want to have a fun time?" she asked getting close.

"S-Sorry, but I'm not really interested..." he said trying to be nice.

"Oh, come on, tell you what, come to the nearby barn and I'll have something you will want!" she promised him, making Naruto go wild.

"Ichiraku ramen?!" Naruto thought while losing himself to his hunger. "You mean it?" he asked, failing to double check her meaning.

"Yeah, don't keep me waiting!" she said hurrying off.

"Yahoo!" Naruto cheered, wanting to eat as after giving her a moment soon ran after her.

------

As Jiraiya headed towards the local gentlemen’s club, he soon noticed a bunch of people gathering in the square.

"What’s all that business about?" he muttered going over to check it out, what his eyes saw made his mouth hang open in shock. "T-T-T-Ts-Ts-Ts-Tsu-Tsu-TSUNADE!" he cried out, finding his love interest strapped to a wide pole, leather shackles binding her wrists to the top of the pole with a long cord connecting her with no slack to it. Her upper thighs bound by a spread bar which kept her legs apart with the bar running into an anchor in the middle which connected to the pole, the same with her ankles as they were bound by an even wider spread bar, as her mouth was kept open with a large wide ring gag.

Gif pic by dawho555 of deviantART

"Gaangngn..." Tsunade groaned with a bright red face as she didn't notice a nose bleeding Jiraiya in the crowd. She moaned and panted out, any of her struggles or panting made her large breasts that were hanging out like utters jiggle like mad and flopped a bit even. 

"Holy... what... gaaah..." Jiraiya cried out, doing everything he could from flying away with a nosebleed.

"Hey there good sir, care to enjoy her? Ten dollars per half hour!" the man offering Tsunade's body said while walking up to the perverted sage with a greedy look on his face.

"You dare treat my friend, nay a fellow Sannin like that! Release her now fiend!" Jiraiya cried out.

"Oh? Know her? Tell you what, pay off her debt and she is free to go!" he offered as Jiraiya snorted heavily.

"Oh Tsunade..." he muttered as she finally noticed him, only for her face to go bright red and felt like dying.

"Jrmrprh?!" she cried out horrified.

"Don't worry, I'll save that peach ass of yours, how much?" he asked as the man smirked and give Jiraiya the number. "What?! Not all of my book sales come to that much!"

"Pay or chip in, your choice!" he said as Jiraiya groaned.

"Guess there is only one thing to do, just give my approval and enjoy the jackpot!" he said grinning as the man running it smirked, soon adjusting the sign to give Jiraiya's approval and with the man's blessing Tsunade would be having a long afternoon, a longer night thanks to that as her mouth would be used raw.

----

"Alright, here I am!" Naruto cheered entering the barn, though entered the wrong one as he found a squirming Sakura on the ground, still tightly bound, blindfolded and gagged.

"MFFFMFMF!" Sakura cried out while thrashing about as Naruto looked on dumbfounded, believing it to the girl playing a trick on him which the sight of a helpless Sakura woke up a hidden urge within Naruto.

"Hehehe, jackpot!" he cried out deciding to jump at Sakura, though she sensed her attacker, not realizing it was Naruto she whipped her bound legs outward, striking him right in the crotch. "Gaaaahhhh...." Naruto groaned out with a dead like look filling his face as he fell to the ground out cold from the strike as Sakura huffed and would have an extremely long night in trying to get free while Naruto slept off his long journey near her.

The end