The Bet

Author's Note: I've always wanted to write a story and maybe a few others for this category. And when an idea came to mind, I fired up my word processor and got started. The title and description should've told you what this story's all about, so I hope you're not looking for an intricate plot. This is just a real-ish kind of story, containing backdoor fun. Hope that'll be enough to get you to your destination. All characters involved in sexual activities are over the age of eighteen and you must be over that age as well in order to continue reading.

Otherwise, please enjoy.

* * * *

What's the deal with anal sex?

Why are so many guys so into the idea of it and want to give the--let's be honest--filthy sex act a try, at least once in their lifetime?

Think, we've got perfectly good vaginas ready and willing to be taken. Yet we want the orifice that was never designed for penetration in the first place.

My theory is even though anal is much more common nowadays, it's still considered taboo. And you know how humans are; we love the thought and taste of forbidden fruit.

I had extra incentive in wanting to give the sex act a try.

Out of all the beautiful features nature has bestowed upon the female species: eyes, breasts, lips, hips, feet, whatever your poison is, my favorite feature is the feminine shape of the buttocks. The ass, the hiney, booty, bottom, tushy, derrière, whatever you want to call it, it's what I love most about women.

A lot of guys enjoy the idea of placing their dick between a pair of giant tits. And believe me, I get that. But what I wanted was to place it between two firm buns and penetrate the little gateway to heaven that lay beneath.

My love of a great ass is what first attracted me to my girlfriend, Brianna Lane, whom I met during my first year of college.

I'll be honest, Bri couldn't be placed into the bracket of the prettiest girls you can find. She wasn't homely, mind you, and I love her, but if I had to give you an accurate rating of what she looked like, it would be a six out of ten.

What she had in her favor, however, was a great personality--like most of us look for in a partner. In addition, her body was to die for. And her sexy British accent didn't hurt, either.

Bri was tall, about an inch or two shorter than me, which would place her at around five foot eight. She was also slender. Not bony, as if she tried her best to avoid food, but the type of slender that'd make you believe she participated in athletics. Which she used to in her younger days.

Bri didn't have big boobs on her side, though. In fact, they were small and could be compared to--let's say, apples.

Another thing I loved about my girlfriend were her legs. They were flawless. They went on and on, and were something one would masturbate over if he caught a glimpse of her in thigh-highs.

But, my girlfriend's best feature was indeed her butt.

She didn't have a huge Kim Kardashian or Nicki Minaj kind of ass, which, because of her slim frame, would've made her look ridiculous. No. Bri had a nice sensible bottom, which you'd still notice from afar.

Don't get me wrong. I love a big derrière as much as the next ass man. But what I believe makes an ass great is definitely its shape. My girlfriend had that in spades. Her ass was full, round and suited her body type to a tee.

I still get a warm sensation that oddly makes me tremble whenever she bends over.

A few months after she and I graduated in our respective fields, journalism and graphic design--I studied the latter--we decided to rent out an apartment and moved in together.

Life was magical during our first weeks. Excluding her time of the month, we made love at least once a day, almost every day, and had done it in every room of our little home.

I'm not sure why we went so crazy. It's not as if we'd never slept together. But it might have been our way of celebrating our newly found independence.

I don't want you to get the wrong idea about Bri. She wasn't as sexually adventurous as I might've implied. Matter of fact, she only allowed me to sleep with her six months after our first date.

Bri was a bit of a church girl. Well, a lot of a church girl. Almost every Sunday she left our apartment to attend Mass--sometimes dragging me along. Not many from the Millennial and Gen Z generations are as devoted as her, but such was the result of her upbringing.

"Don't cum in my mouth, okay?" Her eyebrows rose.

"I know." I pulled her long honey blonde hair out her face.

Her head dropped and lips tightened around my cockhead. She sucked and swirled her tongue around it. Her head bobbed about five times. Then she pushed lower until her lips slid past the halfway point of my shaft.

She tried to get more in, but I knew she'd reached her limit. She pulled up and popped my glans from her mouth. Her tongue ran down the front of my shaft. She took my testicles in and sucked. I groaned as my eyes shut.

I was as smooth as a Ken doll in that region. I'm not sure how many guys maintain that area like I do, since my eyes don't wander in locker rooms. Bri told me a while ago she didn't like the feeling of pubic hairs in her mouth. I obliged by making sure my pubic region stayed clean.

It had its perks, like her taking my balls between her soft lips. I also liked how it made me look bigger. While erect, my cock was the slightly above average size of six inches in length and five in perimeter.

It's true, a lot of men wish they were gifted a monster size porn star cock--and I used to have the same desire. But Bri had long ago let me know most women prefer regular ones. She'd admitted while the idea of a nine inch cock was intriguing, it sounded like a nightmare to live with on a day to day basis.

She was more than happy with my "boyfriend cock," as she'd called it. I suspected her stroking my ego, but it was difficult to deny her logic.

Once she bathed my testicles with her tongue, Bri slid it back up and took in my glans. Her head bobbed without the need to rush. Then her pace quickened as she looked me in the eye.

She gave my glans one last hard suck and then popped me from her lips. She got onto her hands and knees and crawled forward.

I was in the middle of our bed with my back against a couple pillows and the wooden headboard.

Bri stood on her knees, placed her hands on my shoulders and suspended her vulva over my erection. She bent her knees and stroked her clean-shaven slit with my tip, smearing it in pre-cum and saliva.

She took hold of my shaft and placed its head at her opening. Her eyes closed with a groan as she bent her knees and took in the top third of my cock. Her hips dropped lower and once I was all the way in, Bri remained in place.

She looked as if she was at peace with the world. I leaned forward and sucked in her nipple as she enjoyed my girth by humming. I moved on to her other nipple and rolled it between my teeth, earning another groan from my girlfriend.

Bri pushed up until only my glans remained between her wet lips. She dropped her frame again, with much less care this time, bounced off my lap and got into a medium paced rhythm.

"Aaahh," she moaned each time she sprang off my lap.

With my hands on her waist, I slid them lower and around her hips to cup her firm ass cheeks. I kneaded them, loving the feel of her silky bottom. I pushed my right hand farther around her left buttock, slipped my fingers between her cheeks and pressed my middle finger against her rosebud.

Bri stopped bouncing to pull my hand out.

"You know nothing's allowed to go back there, Dale." She frowned.

This is how it's always been with Bri. Butt stuff was completely off the table. She'd said she didn't want to be a complete prude, which is why she's okay with vaginal sex, but even oral sex was a battle. She'd said it wasn't what good Catholic girls do.

However, during our trip to Perth, Australia, which I took her to as a twenty-third birthday present, she was filled with such joy on our first night, she decided to break her rule and gave me the first blowjob she'd ever given a man.

It wasn't mind blowing, I'll admit, but I appreciated it, nonetheless. Although, it did take a couple more months for her to finally give me a taste of her honey pot. Ever since then, her mind's completely changed on the idea of oral.

"Actually, I think you've just killed my mood," she said and pushed up, slipping my cock from her wet folds.

"Sorry, babe. I just couldn't resist. When your girlfriend has as great of an ass like mine, it's really hard to control yourself."

"Flattery will get you nowhere, sir." She moved to sit on the edge of the bed and then reached down to pick up her lacey black panties.

I moved behind her. "Let me make it up to you then," I said in her ear. "What if I went down on you for at least...the next thirty minutes?"

I didn't find the idea of jacking off to reach my climax appealing.

She paused as she pulled her panties up her long legs. "I'll give it some thought." She pulled her panties the rest of the way up and stood. "But not right now. I'm still a little irritated with you."

Her answer gave me hope. I knew once I got my tongue on her clit, she wouldn't be able to resist letting me back in. I could step away from the idea of masturbating in the shower for now, and give her a heavy load in an hour or two.

"What time is it?" she said as she walked to the closet.

I reached for the nightstand and grabbed my phone. "Umm, it'll be noon in about twenty minutes."

"Really? Okay then, my team's about to play. And I have to write the article about their match for our website. Can't believe I almost forgot." She reached into the closet and pulled out her bright red Liverpool FC jersey.

"Who you guys playing against this week?" I said as I picked up my boxer briefs.

"West Ham United."

I thought. "They're one of those London clubs, right?"

"Wow. I'm impressed. Look who's learning about football."

"Soccer, you mean." I pulled up my underwear.

"Hey, football was invented before your American version of it. Or should I say; American version of rugby."

"Well, you're living in the good ol' US of A today. You should probably get used to calling it soccer. You're just gonna confuse people."

She rolled her eyes. Although I could tell she wanted to smile. "Yes. I'm well aware of that by now." She pulled her jersey over her head. "I'm not sure why you even care, though." She pulled her head through and pushed out her arms. "You don't even watch American football. All you care about is baseball."

"Can you blame me? With the way the Jets and Giants play?"

That got a chuckle out of her. It was good to see her getting over my wayward finger this soon. "Are you going to watch the game with me?"

"Uhh, why not? I've got nothing else going on."

*

"So," I said as we prepared snacks in our small kitchen, "think your team's gonna win today?"

"Pssshh, of course we will." Bri emptied a packet of potato chips into a bowl.

"Someone's confident."

"Yes I am. But that's only because, well, we've won our last four games against them--and drew the one before that. We've got the best player in the world right now in our team.

"And even though we're playing away, we just crushed our archrivals, Manchester United, five nothing while playing away to them last week. So what do we have to be afraid of?

"Oh yes, and we're the former champions. I knew covid wouldn't dash my dreams. And West Ham won't stop us from achieving them, again. And did I mention we're still undefeated this season?"

I laughed.

This was the result of growing up with two older brothers and one younger, and another thing I adored about my girlfriend. I'm one of those guys who find women with a deep comprehension of sports to be as sexy as Sofia Vergara in nothing but her tiniest thong.

"I'm not doubting you. I'm just saying, love--you should never count your chickens before they hatch." I pulled a few beers out the fridge and a bottle of soda for Bri.

I knew she wouldn't drink alcohol if she planned on writing after the game.

"Not the best analogy, but I hear where you're coming from. Still, I know we're going to win."

"All right." I mulled, placing the drinks on the counter. "And you're not playing at the...Andfeel, you said?"

"It's Anfield. And no, they're playing at London Stadium. Please get me some cheese, uh, lettuce, a tomato, the pickles and the left over bacon in the fridge." She turned and walked to the bread bin.

"Huh." I thought, examining her.

She was only in her Gerrard--whoever that was--red Liverpool jersey and the panties she'd put on earlier. It looked as if she wore a short dress--with sleeves. (Sorry for my ignorance to Liverpool fans that might be reading. I'm just not a big fan of the sport.) It was a sexy look and gave my frustrated cock and I ideas.

"How are West Ham doing this season?"

"Uh, pretty well actually. I think they're fourth...or fifth on the table."

They're doing well and they're playing at their home stadium. Granted, I didn't know a lot about soccer, but I thought these facts would make the game interesting.

"Dale," she said, holding a loaf of bread, "get the stuff from the fridge. I wanna be done with the sandwiches before the match starts."

"Hang on, I will." More thoughts arrived in my head. "And you're sure your team will win today?"

"Well, I don't know if they'll win. But I'm confident." She shrugged.

"Okay. Care to place a little wager on it then?"

She eyed me with suspicion. "What are you up to?"

"Nothing. I just think a bet would make the game a lot more interesting for me."

She hesitated. "What do you have in mind?"

If you can't tell by now, anal sex is something I'd long dreamed about with my girlfriend. Who wouldn't with an ass as spectacular as hers? But she'd flat out denied me each time I brought up the subject. She wouldn't do it for my birthday, Christmas, Valentine's Day. Nada.

If she'd thought oral sex wasn't what good Christian women do, can you imagine her opinion on this?

I thought of the nicest way to voice my thoughts. I didn't want to be crude, but also wanted to be straightforward.

"Well, I think you know there's something I've been dying to do with you in the bedroom for a while now." I noticed worry in her eyes, but continued, "And I'd be willing to never ask you about it, again. If your team wins, of course. But if they lose, then...well, we get to give it a try."

I knew it was a long shot her team would lose the game. But I also believed that's what would entice her to take me on. So what if the horse I bet on lost? At the rate we went at, I knew we'd never participate in any ass play anytime soon. If ever. And this seemed as good as my opportunities would get.

"Seriously, Dale?" She frowned. "Are you this obsessed with anal sex?"

Honestly--yes. Even when I went online, most of the porn I viewed included anal in one form or another. I couldn't help myself. And I knew she knew that from an awkward discussion we had about my browser history.

The main video I had to explain involved a naked woman in distress, trapped by thin rope connected to the ceiling and a large hook lodged deep inside her rectum.

"Well, no, I'm not that obsessed. But I think you know that it's something that I actually would like to try. And it's not like I'm gonna cheat on you to make that happen. So I thought why not put a wager on it.

"And it really would make the game more fun to watch, by the way. Plus, weren't you all super confident that your team would win today? So why are you so scared all of a sudden?"

"I'm not," she said as intensity filled her hazel eyes.

Even if my girlfriend couldn't be compared to movie stars, I found her golden-greenish eyes to be beautiful. And isn't that the case about all women? No matter the overall appearance, there's always something or another that makes them attractive.

I was also happy to see I'd provoked Bri's competitive side, which was my goal.

"But I would like to know what would be in it for me," she said. What do I get out of it if my team wins?"

"Well, what do you want? I guess you can use a strap-on on me if I lose."

She laughed. "No. How would that benefit me?"

"Name your price."

Bri gave it thought.

"Well, if the stakes are as high as anal, then if--no, when my team wins--then you have to clean the dishes every single day for the next six months. No complaining, no fussing, no bitching, no moaning.

"No excuses like 'I'm tired' or 'I'm busy' or anything else you can come up with. As soon as the sink fills, then you have to get your arse up and deal with it right away. And, just like you said, if we win, then you can never ask me about anal ever again."

I mulled over her proposal. She was asking for a lot, considering the odds were against the team I backed winning. But I was so desperate for my girlfriend's gorgeous ass, I felt I had to take this small window of opportunity. Who knew when another would come around?

"Okay, fine. You're on." I stuck out my hand and we shook on it.

"Okay, now would you open the fridge and get the stuff I asked for."

I chuckled. "Don't worry, I'll make the sandwiches. Go and watch the game. I think it's about to start, anyway. Just take what you can for now."

*

Once I finished with the sandwiches, I picked up the jar of pickles--Bri's favorite fruit/vegetable--then headed to the living room. I heard loud cheering from the TV as I walked. I wasn't sure what had happened, but from the shell-shocked look on my girlfriend's face I knew it wasn't good for her.

"What happened?" I said as I took my seat next to her on the sofa.

"Oh God, we just conceded a goal." She dropped her face into her hands.

"Really now?"

Surely enough, as I watched the replay, the ball was kicked in from the corner of the field, which seemed to fly past everybody and then went into the back of the net.

It put a smile on my face. Perhaps my team wasn't as big of an underdog as my girlfriend had implied. Hope filled my heart, but the game had only been on for about five minutes. There was plenty of time for her team to make a comeback.

"But it's okay." Bri shook her body and head. "The game's far from over. We'll equalize." She brimmed with confidence.

It wasn't easy not to believe her.

The referee's whistle blew and the players restarted the game. I cracked open a can of beer and picked up a bacon sandwich. Bri opened the jar of pickles, stuck one with a fork and we watched.

My opinion on sports has always been that every single sport--baseball included--is boring to watch unless you have a team or individual to root for. Which is why, I believe, for the first time in my life I found a soccer game to be interesting.

I oooohed and ahhhed alongside my girlfriend for missed chances at goals. And became a little more interested in learning a few players' names. I only really knew Messi and Ronaldo.

"So who's the best player in the world you told me about earlier?"

"Uhh, wait...That guy." She pointed.

"The one with the afro that hasn't been combed?"

She burst out laughing . "Yep. That's Mo Salah. He's Egyptian, and brilliant!"

I smiled. "Well somebody has a crush. I better make sure I keep an eye on him if we ever meet him."

"Shut up." She chuckled.

The game went on and soon the referee's whistle blew. A free-kick was awarded to Liverpool right outside West Ham's goalkeeper area. I didn't think much would come from it. It wasn't a "penalty," which I knew would've been worse.