Bet Her Not 2

Well, the last post went over well with folks, so here's a continuance. I really hadn't planned for further adventures of Miss Wiffeneye, but I think this little chapter came out quite well.

Thanks to all who left comments on the last post. I appreciate the effort, and enjoy reading what you all think. Hopefully this sequel goes as well.

- B-Rex

“Fuck, not again!”

Tiffani stopped, struggling to shove his new tits back into his top. The sports-bra was way undersized for his G-cups, and only served to make them bounce that much more. But without the bra he'd never be able finish the run.

“Ah, bad luck, Tiffi,” Jenna said, chuckling. She held out a shoe box, as he glared sullenly at her. “Well, you know the rules.”

He finished shoving his breasts back under his pink top, and snatch the box from her, sighing irritably. He kicked off his high-heels, and put on the new pair, wincing as he tried to regain his balance.

“You're up to seven inches, impressive,” Jenna said, giving him a slow clap. She slapped him on the butt. “Okay, that's enough rest, you don't want to come in last place, now do you?”

Tiffani growled, hopping on one foot as he awkwardly closed an ankle strap on his new pair of heels. Sighing, he fumbled for his phone, shoving his earbuds back in before his roommate could say anything more.

Tugging the pink monstrosity out from his bra, he removed his sunglasses long enough to flash his best 'O' face at the camera's phone, then quickly tongued his way through his playlist, scowling at the options. Try as he might, he'd yet to figure out how to add any of his own music to the phone.

“You're getting better at that,” Jenna replied, as he shoved his tongue into his cheek again, scrolling through songs.

He glared up at her, then moaned and gasped into the phone. “Ooh, oh, ohhhhh, ah!” Instantly his ears filled with the sounds of a raunchy hip-hop song he'd yet to listen to. He scowled as the lyrics began. How the hell did Jenna find so many songs about big butts and fake tits?

He headed off, fighting to keep his balance on the ridiculous heels. He'd lost enough time already, and wasn't going to lose another bet. Last time had been bad enough.

The annual office charity run was never his favorite event, it was always in the dead heat of summer after all, but nonetheless he'd managed to come in the top ten of the 5K run for the last four years.

So when Jenna bet him he couldn't finish above last place, he'd agreed to the bet instantly. Even with his gigantic new tits slowing him down, there was no way he'd finish anywhere near dead last.

He'd been so confident, he'd even agreed to her other conditions, namely that he'd wear high heels for the run. After weeks of wearing heels to work everyday, he'd gotten pretty good at walking in the horrid things.

Of course, that was before she added the final condition; every time his new tits flopped out of his top, he'd have to add an inch to his heels. Now, not even a fifth of the way into the run, he'd already reached seven inches.

At this rate, I'll be on stilts before I reach the finish line, he thought miserably, readjusting his top as he jogged along.

Still, it would all be worth it when he won the bet, and he got to reduce these stupid fake tits to a more manageable size. The last month had been a nightmare of shopping trips and bra-fittings, as every girl at the office wanted to lend the 'new girl' a hand in picking out a new wardrobe to go with his new assets.

Sadly, the giant implants had also brought his sales figures up. He was finally beating Jenna's, fat lot of good it did him now.

Just be calm, Timothy, just a few more miles and you'll be back to a C-cup, he reminded himself, before the memory of his previous lost bets got him down. All you have to do is not come in dead last.

Of course, even as he thought that, another runner passed him by, this time a faceless intern from Receivables. “Oh, hello dollface,” the young man said, grinning as he waved back at the busty crossdresser.

Tiffani glowered after the intern, and his use of one of his approved 'pronouns'. “Fucking asshole,” he swore, then gasped as he suddenly fell forward. “FUCK!!”

His ankle screamed at him, and stared back, swearing again as he saw the broken heel.

“Hey, you okay, babe?” The intern had turned around, still jogging in place. His eyes opened wide.

“What are you lookin--” Tiffani began, then winced as he followed the man's gaze down to his very naked tits. “Oh, damn it, not again.”

He started to pull his top back up, only to realize that in his fall his giant tits had burst his bra straps and torn his pink top wide open. He gasped in horror at the carnage.

“Oh my, that's too bad, Tiffi,” Jenna said, grinning as the crossdressed man pulled his ruined garments off. “But hey, the girls are going to love having you join our pole dancing classes from now on, Tiff. I've got a great outfit picked out for you, your tits will look great in a tube top.” She smiled as he tossed his mangled top away in disgust. “And look at you, you're already getting in the spirit!”

“I haven't lost yet!” he snapped, covering his bare breasts with an arm. They were far from adequate to hide the massive pair, however. “There is no way in hell I'm going to spend every night swinging around a pole while your dumb office friends watch.”

“Don't forget the men on the other side of the gym, they love to loiter around when our classes start,” Jenna giggled, then sighed in mock sympathy as he rubbed his ankle. “Sorry Tiffi, but unless you think you can actually run like that, you've got to face facts; you've lost. Hell, if you try to run with those sweater rippers unsupported, you'll probably give yourself a concussion.”

She pulled another box from her backpack, and tossed a new pair of 8 inch stripper shoes at him. These were all acrylic, and looked like they'd be absolute murder to wear.

She watched him struggle into the clear shoes, and grinned. “Though, I admit, it would be fun watching you flop about for a few more miles. But I think it's time to throw in the towel, dear.”

Tiffani Wiffeneye glared up at his roommate, thinking furiously. Then his gaze turned to the intern, still staring open-mouthed at the salesman's immense rack. An idea came to him, a horrible but desperate idea.

“You, get over here and... grab my tits.”

“WHAT?!” Both Jenna and intern said together.

“Look, just... this is a four-hand job. You can run behind me and be my... ” Tiffani grimaced at the words. “... be my handbra.”

The young man didn't have to be told twice, helping the buxom superior to his feet, unsteady as they were in the new heels. He grabbed a firm grip of Tiffani's giant hooters, making the salesman wince.

“But... but...” Jenna began, bewildered. “If he's behind you the whole time, he'll be dead last no matter how slow you run! That's totally cheating!!?!!”

Tiffani just glared back at her, cupping the undersides of his globular saline-filled breasts for extra support.

“Like hell it is. Now you,” he sputtered, glancing back at the shocked intern over his shoulder. “Whatever you do, do NOT let go of my chest. Every time you do, I get a new set of heels. And I swear, if I have to wear a new pair of heels, I'm going to break them off up your ass, got me?”

“Er, uh, yes ma'am, er, yes, uh, babe,” the man stammered, fumbling for the correct pronoun.

Jenna just shook her head as the pair began to awkwardly run down the path, four kilometers of nonstop groping left before her roommate's latest ordeal was over. She sighed, and chuckled as she picked up his pink phone from where it had fallen and started jogging after them.