Stainless's was mostly empty, as it usually was on Wednesday. A small group of regulars Jake could trust and knew fairly well was the kind of crowd enjoyed at his regular bar back on earth, and having a similar place to go after ending up in Equestria made his transition much easier.

Jake went to Stainless's every Wednesday for the open poker night. Buy in was sixty bits, but with a table of five he could walk home with enough money for the month. Jake was a damn good poker player, he won the pot at least once a month. The only person at the table tonight he had to worry about was Crosscut.

Crosscut was a lumberjack that woorked in the everfree with Jake's buddy Mark, who had told her about their pokernight about three months ago. Thinking it might be fun Crosscut started showing up and showing her skills to Jake at the table. She couldn't hide a good hand to save her life, but Crosscut could bluff her way out of East Berlin; and if that didn't work she could probably fight her way out given how strong she was from pulling logs all day. The girl was a real poker player, unlike Mark.

Mark wasn't rich but the boy never bought anything, so he had a respectable ammount of money to throw around. He played with Jake just for fun. Played isn't the right word. The boy usually went all in and ate shit in the first five hands or so, but he had a good time and no-one was gonna tell him not to add free money to the pot... except Jake.

"You sure you wanna play tonight Mark? You've had four already and you havn't won once sober", Jake asserted as his friend took a seat.

"You know I just play to get drunk and call bullshit. Besides as long as you win I get my money back"

Jake scowled at his friend before looking at crosscut. "What about you Cross? You in?"

"Hell yah!", she exclaimed handing her bits to Stainless and grabbing her chips. "I'm feeling lucky tonight"

"Well so am I, so let's get this game started" Jake grabbed the deck and dealt the hand. "Aces are high, big blind it two red chips, small blind is one, and no you don't have to show folded cards"

"But I like to know what they had!", Mark complained

"You wanna show your cards fine but it gives an advantage to players still in the hand", Jake explained as he layed out the cards. Grabbing his cards Jake saw he had a couple queens for the first hand.

Oh this is gonna be a good night

{one hour later}

Everypony had gone bust except for Jake and Crosscut. Mark got knocked out when Stainless told him to call his bluff, and he decided to go all in on a pair of sixs.

"Whoop her ass!", Mark hollered as he downed his tenth beer at the bar.

Jake meanwhile was staring at two aces, with the other two and a 9 of spades in the flop; four of a kind. Looking over at Crosscut Jake smiled and pushed all the chips he had collected into the center, "all in."

Crosscut had more chips and could have simply called his bluff, but holding only a 7 and 8 of spades she folded and let him take the blind.

Flipping the last two cards for the river, Jake revealed a 10 and jack of spades. "Hope you didn't have nothing" Jake joked pulling the take back to himself.

Face-palming Crosscut reached out and flipped her folded cards over.

"Oh-ho, now that's bad luck", Jake lauged and handed the deck to Crosscut. She shuffled and dealed out the next hand. The blinds went in and Jake checked his cards. He had a king and queen of hearts. Good cards yes but not enough to go all in on.

"I raise", he said placing four red chips in the center.

"Me too", Cross replied placing eight. She then flipped the flop to reveal Jakes dream cards. A jack, 10 and ace of hearts.

It took no small ammount of effort on Jake's part not to cry as he pushed his chips to the center once again. "All in."

"You're bluffing"

"Am I?"

Crosscut scoffed and pushed her chips to the center as well. "you are", she then flipped the last two cards over to reveal the aces of clubs and diamonds giving Crosscut a total four aces. She smiled as she layed her cards out on the table.

"Four of a kind", she smugly declared. "Lay'em out human boy."

Jake leaned forward and placed his king and queen on the table. He leaned back in his seat and watched as Crosscut's jaw hit the floor. It was silent for a moment before Crosscut acknowledged what she was seeing.

"No fucking way!"

"I didn't believe it either", Jake stood up. "Good game" he remarked before walking to the bar to join his drunken friend and collect his winnings.

"You win Jake?", Mark slurred as Jake grabbed the bag of bits from Stainless and stuffed them in his jacket.

"No Stainless owes protection", he said sarcastically.

"Really?"

"No"

"Oh... Well thast girl didn't need the money anyway", Mark said smacking Jake on the shoulder.

"What makes you say that Mark", Jake grabbed Mark's beer and took a swig before looking back at Crosscut. She was leaning back in her chair staring blankly at the messy poker table like it wasn't even there.

"She was at work beggin for bits, sayin it's for her medicine or somethin. I think it's drugs she's after. Cant do the kinda work we do and not be on somethin", Mark explained as he waved down the girl for another beer.

"I can see that", Jake took the other beer from the bartender before Mark could get his hands on it and made his way back to the poker table. He set the beer next to Crosscut and took a seat.

"I don't need you to buy me a consolation drink", Crosscut barked, crossing her arms and staring at Jake.

"What about medicine?", Jake reached into his coat and pulled out the bag of bits, giving it a giggle.

Crosscut grabbed the beer he had set down, drank a couple gulps, and took a deep breath. "I need an elixer from the alchemist in Canterlot, it's expensive. Rich ponies use it to stay youthful."

"What do you use it for?"

"I use it to maintain my joints so I can keep working, me looking good is just a happy side effect", Crosscut chugged the beer and tossed it in the trash across the room.

"How long have you needed it?"

Crosscut rubbed her head, "About fourty years or so."

Jake spat out his beer and leaned forward, "Fourty years? You don't look a day over thirty! How old are you?!"

"Old enough."

"So how much does Your "medicine" cost?"

"About 300 bits a bottle."

"Jeez, how long does it last?"

"A month or so."

"Tell you what Cross, you make sure my drunken friend gets home", Jake tossed the bag of bits onto the table, "...and you can have that... provided you use some to pay his tab."

Crosscut had a skeptical look on her face, "what do you get out of this?"

"Just make sure you show up next week so I can win it back", Jake stood up and walked out of the bar.

Crosscut stared at the bag for a moment. A generous man... huh, havent seen one of those in decades she looked over at Mike and saw the boy was swaying from side to side just trying to stay in his stool. "Or not"

{later at Jake's house}

"Ugggg, why did I do that!", Jake complained to himself, tossing a pile of bills onto his desk. "Ehh, I'll be fine", He sat down at his desk and turned on his computer to finish season two of The Boys when a thunderclap hit outside.

"And now I'm using the computer during a thunderstorm. Just making all kinds of stupid decisions today now aint I"

*knock knock knock knock*

Jake paused the video and went to get the door. Opening it he found Crosscut standing there with Mark slung over her shoulder and Mark's keys in her hand.

"Let me guess", Jake moaned rubbing his eyes with his thumb and index finger.

"Yah he went dark about tewnty minutes after you took off, and Stainless said he usually ends up here when he goes this hard soo..."

"Yah, yah... throw him on the couch."

Crosscut walked inside and literally tossed Mark onto the couch. "Now, I guess I need to address the elephant in the room", Crosscut turned to Jake. "He didn't make it home."

"It's fine Cross you can keep the money", Jake responded sitting back down at his computer. "Go get your medicine."

Jake then found a large pair of soft breasts reasting atop his head. "I figured you'd say something like that"

Jake slowly removed his headphones and stood up, "There's no need for that."

Crosscut looked at Jake and then over at Mark then back to Jake. "Ohhh your gay, sorry"

"What!? NO!?"

"Really? then why the reservation?"

"I'm not gonna sleep with you because you feel like you owe me."

"Oh baby", Crosscut stepped forward and kissed Jake on the forehead. "You didn't buy me a drink...", she reached into her purse and pulled out the bag of bits tossing them onto Mark's passed out body. "You won me with the gesture"

Grabbing Jake by his hand Crosscut led him up the stairs like a obedient dog. Walking into the bedroom she sat him down on the bed and started to slowly and seductively stripping away her clothing. Once down to only her underwear and socks she got on her knees and began stripping down Jake. Pulling his shoes and socks off, then un-buttoning his pants.

"Wait", Jake interupted. She didn't.

With one swift motion she yanked Jake's pants off and stared at him with bedroom eyes.

"I was gonna ask if you were sure you wanted this but", Jake got his tongue caught in his throat as he looked up and down her georgeous body.

Reaching down Crosscut expertly pulled out Jake's package with one hand and eyed it in confusion. "I'm big for a human", Jake assured her as she inspected his cock.

"Oh that's not it Jake. It just looks funny"

Before Jake could chide the girl on her choice of words his breath was stolen by his cock being sucked into the Mare's warm mouth. Rather than bob her head or anything, Crosscut used her long tongue and entire mouth to massage his member in a way he had never experienced before.

Rolling around the tip and licking the shaft she worked the top of his cock by pressing it against the roof of her mouth.

This is the most amazing thing I've ever felt, Jake thought... until Crosscut stuck her tongue out and sucked his balls into her mouth as well. "Holy hell", he said aloud as the mare played him like a fiddle and sent him rocketing towards climax in mere seconds.

"Hold up I'm gonna!" Jake said no but his hands flew to Crosscut's head as his cock disgorged a large load of yummy seamen into Crosscut's maw. He held her there for a few seconds before removing his hands, allowing her to pull off.

Crosscut opened her mouth to show Jake the mess he had made inside. She swished it around a bit before closing her mouth and gulping it down in dramatic fassion. She then opened her mouth to show it was all gone.

"How was it?", she asked looking at Jake with those big beautiful eyes.

"That was the best thing I've ever felt... ever!"

"Heh, ready to get lucky for the second time tonight", Crosscut pushed Jake back and flat against the bed. climbing on top of him and pulling off her bra to let her amazing tits flop free. "Let me show you what almost a hundred years of experience feels like."

To Jake's suprise his cock was still rock hard when Crosscut reached down and grabbed it. Tugging her panties to the side she slid the slick member into her moist pussy and ploped herself down in Jake's lap.

"oh-o-ho-ho, that's tight", Jake moaned while Crosscut made slow back and forth motions in his lap.

"Better than your hand right?", Crosscut joked as she helped Jake pull off his shirt.

Jake grabbed the mare's thighs and gave them a squeeze, "I dont know, your kinda old"

*smack* Crosscut smacked Jake right in the face. Jake just smiled and bucked his hips.

"That's the spirit!"

Crosscut placed her hands on Jake's chest and tried to pound him into the mattress using her ass.

"Not bad for a human", she praised while Jake brought his hands to her taut belly, rubbing along as she rode his human cock for all it was worth.

They fucked eachother sensless. Jake had never been with a pony girl before, and was regretting holding out for a human.

Crosscut never thought a human would ever measure up to a stallion, but Jake was hitting all the right places inside her. They both wanted to say as much but the pleasure was holding their minds.

After a few minutes of havenly humpy pumpies the two couldn't hold back anymore.

"I'm cumming!", they cried in unison.

Crosscut bent forward and brought Jake into a deep kiss, as the boy fitfully pumped his cum inside her. They kept making out untill well after both of them had rode out their orgasms. It took a full ten minutes for Crosscut to break off the kiss.

"that was amazing... for a human."

Jake chuckled, "Yah you wern't too bad for an old lady"

Instead of planting a fist in his face Crosscut placed a kiss on his head. "Well, thanks for giving this old mare a good time", She then rolled over and went to sleep, exausted from the long day of work, highs, lows, and sex.

{the next morning}

"Alright sweet thing, I gotta get to work but I'll catch you next Wednesday... or maybe sooner", Crosscut winked before she shut the door and rode away.

Jake's attention was pulled from the window when Mark stirred from his sleep, as he sat up on the couch the bag of bits Crosscut threw on him fell off. Walking around to the front of the couch Jake saw the gold coins had spilled all over the floor.

"What happened... why am I at your house Jake?", Mark asked as he regained his faculties.

"We had sex", Jake answered flatly

"Really? How was I?"

"Not you!", Jake blurted, "Me and Cross", Jake clarified as he started picking up the bits and putting them back in the bag.

"Oh", Mark said with a hint of sadness in his voice. "How was she? I've never tried a pony."

"Amazing. That girl was more than she appeared to be."

"Are you gonna see her again?"

Jake stood up as he finished placing the last bit into the bag and looked out the window. Giving the bag of bits a shake, Jake knew she probably still wanted and needed them. "Yah, real soon to"

Author's Note

I don't usually like vanilla male on female but this was fun