Five Dollar Bets
by Pan
Chapter 1
The Kelly Twins looked at each other with a smile.
Jason was a nice guy, but a truly hopeless gambler—they’d never seen him win a bet. For the past six presidential campaigns, he’d bet on the winner, and lost every time. He’d bet against LeBron James often enough to send a normal man bankrupt; his only saving grace was that he only ever made tiny, tiny bets.
And so when Jason had offered them a wager, the twin girls had giggled and accepted without question.
“Hang on,” he said, confused. “You don’t even know what the bet is, yet.”
“Sure,” Mickey said, shooting Jason her most charming grin. “What’s the bet?”
“Well,” he said thoughtfully, “Now that I know you’re definitely going to accept, I should go with a sure winner.”
“Sure thing,” Martha said, mirroring her twin’s smile. “Anything you like.”
“Okay,” Jason said, slamming his hand down on the table triumphantly. “I will bet you five dollars…—“
“Oooooh,” the girls chorused mockingly, before breaking out into giggles once more.
“I will bet you five dollars,” Jason repeated, undeterred, “that by this time next week, one of you will fuck the other with a strap-on dildo. In the ass”
The laughter died away, and the sisters exchanged a confused glance.
“What?” Martha asked, after a pause.
“I bet that by…” Jason checked his watch. “Nine-oh-five Tuesday night next week, you two will have fucked each other in the ass with a strap-on dildo.”
“Jason,” Mickey said softly. “That…that doesn’t make any sense.”
Jason blinked twice, and looked at the two of them.
“You’re right,” he said eventually. “I’m sorry. Let me be more specific. I bet that you…”
The young man pointed at Mickey with a smile.
“…will fuck you…”
His finger moved to Martha.
“…with a strap-on dildo—in the ass—by five past nine on the 27th of September, 2016. Now, I know five dollars is a lot of money, so if you don’t want to accept…that’s fine by me. What do you say?”
The two sisters didn’t even need to look at each other.
“You’re on,” they said simultaneously, and Jason solemnly shook their hands, one after the other.
“That was weird,” Mickey said, staring out of the window on their train ride home.
“I know, right?”
“Do you think he was…”
“Yeah,” Martha answered, not even needing her sister to finish the sentence. “He must have been.”
“Still weird.”
They lapsed into silence again.
“I mean…”
Mickey turned around. Her sister was obviously uncomfortable with the conversation, and wanted to vent.
“What?”
“I don’t even own a strap-on dildo. Like, why would he think that would happen?”
“Ah…”
Martha’s eyes widened.
“No way!”
“Yeah,” Mickey said sheepishly. “Remember that guy I was dating a few years back?”
“Clyde?”
“Yeah. Turns out he was super into pegging.”
“Wow. Do you think he told Jason?”
“I didn’t even think they knew each other.”
“Jason knows everyone.”
Mickey thought for a moment.
“I doubt it. I mean, he was super embarrassed about it.”
“Is that why you never told me?”
“I don’t tell you everything!”
Martha rolled her eyes, and Mickey couldn’t help but laugh.
“Fine,” she said. “I tell you everything. Except that.”
“Anything else I should know?”
“Only that there’s no chance we’ll be…I mean…y’know.”
“Yeah,” Mickey said with a smirk. “That would be weird.”
That night, Martha was straddling her boyfriend, grinding against him, when a thought struck her.
“Stu,” she said, and he moaned in response.
“Stu…” she repeated, slightly more insistently.
“Mmmm?”
“Have you ever…oh!”
Stuart’s hands had made their way between her legs, and he’d plunged two fingers into her wetness without warning.
“What?” he groaned. “Oh god, baby, you’re soaked…”
“Have you ever…”
“What?”
“Have you ever done…y’know, butt stuff?”
She could feel Stuart’s fingers tense up slightly inside her.
“…my butt?”
“No!” she said quickly, and then paused. “I mean, have you?”
“No!” he said, just as quickly.
“Right,” she nodded. “But have you ever done…butt stuff…with a girl?”
“Yeah,” he grinned, his dark eyes flashing with mischief. “Do you wanna…”
“No…” she said, quickly and very quietly. “No, I was just…oh!”
Stuart had moved one of his juice-coated fingers to her ass, and was softly pressing on her tight rosebud.
“Are you sure?”
“Yesss…” she said, but when his finger started to move away, it left her feeling strangely empty.
“Mickey…” Martha said, kicking the back of her twin sister’s chair.
“God,” Mickey said, throwing her hands up. “What are you, nine years old?”
“No,” Martha grinned. “I’m just bored.”
Mickey threw her sister a strange look.
“What?”
“I’m bored.”
“Marth, you haven’t complained about being bored since…well, since you were nine. You have a phone. You have the internet. Hell, unlike some of us right now, you have a boyfriend. You have literally no reason to be bored.”
“I know,” Martha said with a pout, and Mickey sighed and put her pen down.
“What? What is it?”
“Come here.”
Mickey moved from her desk chair to the double bed in the middle of her room. The girls hadn’t slept in the same room since they were teenagers, but they still came into each other’s spaces fairly often to keep each other company.
She sat on the bed, facing her identical twin sister.
“What is it?” she said earnestly, looking straight into Martha’s eyes.
“I was just wondering…”
Martha blushed.
“What?”
“I was just…I was just wondering…”
“Spit it out, Martha. Jesus.”
“I was just wondering…if you’d ever kissed a girl?”
“Oh.”
Mickey noticed her own cheeks beginning to heat up at the question.
There was a long pause, as the typically-frank twins avoided each other’s gaze.
“Yes,” Mickey finally responded.
“No way!” Martha said, her jaw agape.
“Just once,” her sister quickly clarified.
“Mickey! I thought we told each other everything!”
“We do! It’s just…this was…god, this is so embarrassing.”
“What?”
“Well, this was…oh my god, you can never tell her I told you this.”
“What?”
“This was with our cousin.”
“Tilly?? You kissed Tilly?”
“Just once!”
“Oh my god!”
“It doesn’t count with cousins! You know that!”
There was a pause, and again the sisters both looked away.
“God,” Mickey finally said, breaking the silence. “You probably think I’m a total freak.”
“No,” Martha mumbled.
“No, seriously. Yesterday you learn about the strap-on…today you learn about Tilly. Ugh. This is why I didn’t tell you!”
“I swear,” Martha said, looking up and gazing straight into her sister’s eyes. “I swear: no judgement.”
“Really?”
“Really.”
The twins sat in the most comfortable silence that they could remember, blushing furiously and staring into each other’s eyes.
“Besides,” Martha eventually added. “Like you said—cousin. Doesn’t count.”
“Right.”
“…what was it like?”
Mickey’s face felt as though it could burst into flame at any second.
“Nice,” she finally said. “It felt really nice.”
“Huh.”
The twins stared at each other for almost five long minutes, their faces burning, their hearts racing. Mickey finally opened her mouth to break the silence, but when she couldn’t think of anything to say, Martha leaned forward.
“Martha…” Mickey whispered, when her sister’s lips were less than an inch away. “Are you sure you want to do this?”
“We’re twins,” Martha whispered shyly. “Doesn’t count.”
The pair smiled, and neither of them felt any shame as their lips touched.
“It doesn’t count” became their secret mantra. Each night, Martha sneaked into Mickey’s bedroom, and each night the pair made out until sleep overtook them.
At least, it started as making out. Each night, they went a little further than the last. The second night, Mickey practically tore Martha’s top off; on Friday night, Mickey was naked when Martha slipped into bed with her, and they drifted off to sleep later than night with sticky fingers.
On Saturday night, the pair tasted each other’s juices for the first time, and on Sunday night…
On Sunday night, Martha made a request.
“You want me to what?”
“Please,” Martha begged, writhing around on the bed. “It doesn’t count. You know it doesn’t count.”
“I know,” Mickey said, one eyebrow raised. Her face broke into a grin. “I just didn’t realize that my sister was such a little perv.”
Licking her finger, she moved it to her sister’s virgin asshole.
“Are you sure about this?” she whispered.
“Oh god,” Martha moaned. “Please. I’m so, so sure.”
“Okay,” Mickey said and her eyes lit up with lust at her twin’s reaction to her administrations. Her tongue returned to her sister’s clit, and she began tonguing it mercilessly. Martha’s body shook with orgasm after orgasm, and when it looked like she was starting to calm down, Mickey set her off again by whispering in her ear.
“That’s only one finger.”
“Oh!” Martha moaned, bucking so wildly that she almost threw the two of them off the bed.
Monday night, Martha had a date. She greeted her boyfriend with a grin, and before he could ask what had put the spring in her step, she leaned in and whispered in his ear.
“I want you to fuck me in the ass.”
For the first date night in the history of their relationship, they skipped the movie, and went straight back to his place.
“Oh my god,” Mickey said, wide-eyed. “How was it?”
Martha was lying on her chest, running her fingers up and down her sister’s naked back. Occasionally she would stop and grope Mickey’s pert ass, or fondle her thighs briefly, before returning to tracing patterns.
“Mickey, it was…oh my god. It was amazing.”
“Really?”
“You’ve never done it?”
“Nope. Never really wanted to.”
“Oh.”
For the first time since they’d kissed, there was a moment of awkwardness between the two girls. It hung in the air, like thick cotton. Martha’s hand continued, but it was no longer making patterns, just awkwardly moving up and down the other girl’s skin.
“Oh!” Mickey finally said, understanding what her sister had been implying. “Oh, Martha, darling, no…”
She reached down and tilted her sister’s face up, and covered her lips with her own.
After they’d kissed for a few minutes, Mickey pulled back.
“Martha, I’ve never really wanted to…y’know, for me. But for you…”
“Yeah?” her twin smiled, shyly.
“Oh my god, Martha, I literally can’t think of anything hotter.”
“I, um…”
“What is it, sis?”
“I…I have lube…”
Mickey grinned, and got out of bed to fetch her toy.
Jason was sitting behind his desk when they returned, shouting at the screen.
“No no no no! Come ON!”
The Kelly Twins glanced at his computer.
“New episode of Scooby Doo?”
“Yeah,” Jason said with a sigh. “I bet that Scooby would fuck Daphne before the first act break.”
“Ah.” Mickey struggled to hide her smirk. “So now you’re broke?”
“Nah. Just down a dollar fifty.”
He turned to the girls with a smile.
“But I’m sure that you two are here to help me recover from my loss. Am I five dollars up?”
“Nope!” Martha said, unable to hide her glee. “In fact, you owe us five dollars.”
“No freaking way,” Jason replied with a glare. “Are you serious??”
“That’s right,” Mickey said coolly.
“Let me get this straight—you didn’t fuck your twin with a strap-on dildo?”
Mickey sat on Jason’s desk, crossed her long legs, and raised one hand.
“I solemnly swear,” she said, making firm eye-contact, “That at five minutes past the hour of nine o’clock, I had not fucked my sister’s ass with a strap-on dildo.”
Jason turned to Martha.
“Is this true?”
“At nine-oh-five last night,” Martha repeated, “the inside of my ass had never seen a strap-on dildo.”
Jason sighed.
“God,” he grumbled, counting out dollar bills. “This day just couldn’t get any worse.”
The twins exchanged a look, and Martha nodded.
“Of course,” Mickey said, snatching the money out of Jason’s hand. “We were watching the clock very closely. And at six past nine, there’s a chance that was no longer the case…”
She leaped off the desk, and Jason smiled as he watched the two girls holding hands as they walked away.