John felt a lump swelling in his throat as he stared down at his phone. He was beginning to worry for Steven. Bet aside, Steven may have been genuinely depressed.
*I’m here for you, bud. I think some time to grow would be good for both of you.*
It was the last message he sent him. The little status indicator said: *read,* but Steven hadn’t replied.
John backed out of the screen, scrolled up, and then tapped open his conversion with Maddy.
*I’m popping that ass-cherry tonight!!!*
Maddy had been teasing him like that since they agreed on the bet two weeks ago. Maybe it served him right. It was more than a little insensitive to make a bet, about their friends’ hapless love lives. Though to be fair Tricia and Steven had been on again, and off again for the past four years and even they made jokes about it.
His guts were tied in knots. He had to be stupid to agree to this bet. Tricia and Steven simply had to decide they weren’t breaking up after all, at least not today. Then, Maddy would have him grabbing his ankles and his asshole would be filled to the brim with silicone cock in the next hour or so.
There were three heavy taps on the door in quick secession. She was here. After a brief pause, there were several quick thunks each one more impatient than the last, though it had only been a few seconds.
John shoved his phone into his pocket, took a deep breath, and hurried to the door to let her inside.
“Hey, Bud!” Madeline greeted him cheerfully, as the door swung open. She pulled him in for an aggressive peck on the cheek. It was a recent development that he wasn’t quite used to. Her lips felt soft, and the heat of the kiss seemed to linger on his cheek.
She looked like she had just left the gym. Which wasn’t all that surprising. She practically lived there.
She was fresh-faced. Her chestnut-colored hair was still matted in spots from a recent shower. It looked glossy and thick, draped over her shoulder in a damp spool. She was wearing a loose-fitting sleeveless Tapout hoodie. The strap of a Vintage JanSport backpack hugged her shoulder. He could see the ruffled end of some olive green cargo shorts beneath the edge of her hoodie.
“Hey yourself,” John answered, “what’s with the backpack?”
Maddy smiled as she flung the backpack in front of her. She carefully pulled the drawstring open. She was dramatically slow about pulling the strappy leather device free from the bag. A single strap was curled around her index finger as she dangled it halfway out of the bag. It looked like some kind of fancy leather jock-strap, with a bunch of buckles and a circular-shaped pouch cut in front.
Her strap-on harness. He recognized from the video she texted him. She was pretty insufferable when she wanted to be. She had apparently already decided she was winning before either of them knew whether Steven and Tricia were back together or not.
While the video she sent him did turn him on. He was way more focused on Maddy’s perfect, plump ass framed in the leather straps, bouncing away as she plowed into some beefy dude’s backside.
His head and shoulders were cropped from the frame, but he could hear him grunting as she flashed the camera a bright and shining smile.
She was smiling at him now. A small but welcoming and come hither smile.
“It’s like 4 in the afternoon,” he chided, glancing back towards the living room to see if anyone else had seen.
“So, what?” she countered, “Steven text you back yet?”
“No,” he answered, “Matt and Trevor are here though.”
Maddy turned into the kitchen and helped herself to a bottle of Sam Adams from the fridge before they made their way to the living room.
Matt and Trevor we’re sitting across from each other. Their legs crossed with two bottles of beer and several different tabletop games between them.
Game night had been a weekly occurrence for the last two or three years. Lately, it had more or less devolved into sitting in front of our game of choice, while they had passionate political debates, or gossiped about some workplace drama, really anything but playing the game.
Both guys cheered, “Maddy!” As she came inside to take up her usual spot on the couch. It was a level of enthusiasm that was exclusively reserved for her.
Despite being a bit obnoxious, Maddy had an easy spirit. She also happened to be naturally stunning. Like gazing across the Colorado Mountain range at sunset. If she wasn’t so open and honest about her love for sodomizing her male partners she probably could’ve torn through their little friend group like tissue paper.
“Have either of you heard from Steven?” Maddy asked before taking a sip of beer.
“Nope,” Trevor sighed, “He and Tricia broke up again …so they won’t be joining us.”
“Yeah, last I heard Tricia was packing her things, and she was moving back in with her parents,” Matt agreed.
“I can’t believe this…” Maddy groaned.
“Believe it?” Matt questioned, “They break up like once every six months.”
“I know, but it’s been like two weeks, are you guys sure they haven’t made up?”
John was surprised she was openly pleading for answers. Up until now, they both had been pretty tight-lipped about their bet.
“I mean, Tricia is packing her stuff… that’s pretty serious,” Trevor chimed in.
Matt waved his hands dismissively, “Yeah, I guess… but you know Steven is going to get all mopey and depressed, and then he’ll be begging for her to come back.”
John noticed Maddy looked nervous for the first time in weeks. There was a chance that Matt was right, but the established end of their two-week bet was yesterday. Upon Maddy’s insistence, they had to confirm their friends’ were in fact ‘still broken up.’
John nervously peeked at his phone. There were still no new messages.
“When did you guys hear from Steven last?” Maddy asked before taking a large swallow of beer.
“Dunno, like yesterday?” Trevor said, as he thoughtfully examined a box containing a knock-off version of Catan.
Maddy winced, wrinkling her nose, “I’m going to go ahead and call it.”
John felt the knot in his guts come undone. He couldn’t believe she conceded. He had actually won.
As expected, Matt and Trevor both looked back at her confused.
“Calling what?” Matt asked after not receiving an explanation.
“John and I placed a small bet as to whether or not Steven and Tricia we’re going to get back together for the thousandth time… I just lost…” she admitted.
John could feel panic clawing its way up to his throat like a scurrying rat. He wondered why she just admitted to their unscrupulous bet and he wondered how much he’d have to explain.
“That’s fucked up,” Trevor said rather causally before continuing to compare and contrast two different boxes of novelty card games.
“What were the stakes?” Matt wondered aloud.
John felt his cheeks begin to burn, “it was just a stupid bet,” he answered, but Maddy chose to speak over him, “the loser is the winner’s personal hmmm, let’s say *attendant* for the next 24 hours.”
John narrowed his eyes at Maddy, but he couldn’t really understand the purpose of divulging every little detail regarding their bet. His first instinct was she was trying to guilt him into calling the whole thing off.
Matt laughed, “Jesus bro, that was a gamble. Maddy would’ve definitely butt-fucked you outta your soul.”
“I know…” John admitted shamefully.
“No,” Maddy insisted, “he would’ve loved it.”
“You guys were seriously gonna fuck each other because of a bet?” Trevor asked, now fully invested in the conversation.
“I mean why not?” Maddy admitted, “…but I suppose you could just make me rub your feet or do the dishes, or whatever?” Maddy clarified aloud while glancing back at John.
He was so relieved he had won, he had completely forgotten that winning made Maddy his personal plaything for the next 24 hours.
He could heat rushed to crotch, pitching a tent in his jeans. He couldn’t deny that he had fantasized about her before. His fantasies were mostly vague and intangible.
The options overwhelmed him, but more than anything he knew he wanted to fuck her ass. Maddy’s ass was round, and undeniably thick. It was a combination of good genetics, coupled with vigorous squats, butt crunches, and all the weight training she did in the gym. It was the kind of ass that would satisfy even the most discerning assoholics. Her gorgeous butt aside. Maddy was a proud sodomizer herself. If anything, she had put the idea in his head.
“John?” Maddy called out pulling him away from his thoughts, “So, what’s the deal? Bet’s done. How may I be of service?”
“I don’t know,” John said, not willing to admit anything in front of Matt and Trevor, “let me think on it.”
“You’ve been so cagey about it!” Maddy teased, “if you’re having trouble deciding… just so you know, I’ve taken…” Maddy took a moment and began idly counting her fingers, cycling through a mental portfolio.
“…The anal virginity of like seven guys, not to toot my own horn, but that’s a ton of experience.” She continued briefly holding up the seven digits, “I promise you’ll have a great time. We’ll just try it once, and then we’ll do whatever you want for the rest of the 24 hours.”
“Maddy, that was what you wanted… not what I wanted,” John countered.
“Fuck… You wanna fuck me up the ass, don’t you?”
“W-WHAT?” John stammered, “I haven’t said anything like that.”
“Yep, there it is,” Maddy sighed, “It’s the first thing guys also ask for… Do you know how many times I’ve heard: Oh, if you’re gonna do mine, I should get to do yours,” Maddy scoffed, “—still have virgin butthole until this day. Everyone one of them came their brains out on my strap-on and begged for another round. I’m just saying you’d have a much better time. You have a prostate.”
This felt like a tactic, she was trying to embarrass him into absolving her from the loss. Still, if she wanted out that badly, it felt wrong to force her.
“You know we don’t have to go through with this. It was a stupid bet,” John conceded.
“Well, wait a second,” Matt interrupted, “if he doesn’t want to take the win, I’ll take it.”
“You weren’t a part of the bet,” Maddy pointed out, “why would you win anything?”
“…I mean you guys said that the stakes were; the loser, Maddy,” he said gesturing to a smirking Maddy on the couch.
“Now here me out, the loser,” Matt repeated, “has to do whatever the winner wants for 24 hours, basically, so, according to the rules of said bet: John can just bestow his win to me, right? As long as it’s something he wants to do, like a command, right?” Matt deliberated with all the bravado of a made-for-television lawyer making his closing statement.
Maddy raised a straight brow, and gave Matt a coy little smirk, “I mean… sure I suppose those are the rules. But, only if Johnny-boi were to say so… but out of curiosity, what would be in store for me?”
“Nice try Matthew, but no,” John replied before Maddy got an answer.
“Okay, John… what about since there’s three of us. She’s got three holes. What if we all went at once?”
Maddy playfully rolled her eyes, “alright, nevermind, Matthew is being completely indignant.”
“Jokes, on you I don’t know what *indignant* means,” Matt countered, “besides this is John’s decision. You lost, remember? John, bro, hear me out, all three holes at once. Air-tight, bro. AIR-TIGHT. That is literally on my bucket list.”
“Guys, I don’t think Michelle would approve,” Trevor cut in.
Matt let out a deep sigh, “You’ve been dating her for like what, 2 maybe 3 months? We’re talking about a once-in-a-lifetime opportunity.”
Maddy laughed, “Seriously, guys. I’m still here.”
“Maddy would’ve let John off the hook,” Trevor suggested.
All three men turned her, expectantly.
Maddy gave them all a pained and pensive look, “Look, see that’s not fair,” she protested, “I know John would’ve had a good time. Every guy I’ve done it with was apprehensive at first.”
Trevor let out a tickled groan, “Jesus, Maddy… alright you guys can talk it out… I love you all but this is a little weird.”
Matt had a smug look on his face, “Alright, obviously Maddy was totally down with wrecking your butthole, bro…”
“HEY, I wouldn’t have wrecked it!” Maddy interrupted.
Matt continued ignoring her protests, “you totally would’ve been a man about it.” He said turning to John. “I get that it’s weird, but it’s not THAT weird. We’ve been friends awhile… but if you think a little gangbang among friends is too weird, what if we just took turns?”
“I don’t know,” John answered looking back at Maddy, “I honestly value our friendship, more than this stupid little game. I think we should pretend none of this happened.”
Maddy looked back at him with misty eyes, “I can’t believe I’m saying this, but that isn’t fair. I would’ve been pretty salty if you lost, and then tried to weasel out of it… but if I were you, I would just take me for yourself. It WAS our bet. Matt and Trevor can’t be mad about it… and I promise I’ll do whatever you want. You can be the FIRST guy in my butt. Seriously; certifiable virgin butthole. Unless you count tongues and butt plugs, otherwise, nothing else has been up there, all yours,” Maddy said proudly.
“TURNS?” Matt suggested again, “Come on bro, you would go first, obviously. You know I would give you at least a turn with her asshole. She’s been porking dudes up the ass for years, if we all get a turn that’s like poetic justice or whatever, think of your fellow men, mah-guy?”
Maddy laughed, “Jesus Christ, Matthew, you fucking horndog. You can’t be serious?!”
“Please, you’re loving this, otherwise, you wouldn’t have said anything about the bet!” Matt countered.
Maddy gasped, “Matt, I do rather enjoy being the center of attention, but if I knew you were going suggest running a train on my ass, I would’ve shut up about it.”
“She doesn’t seem into it Matt,” Trevor pointed out.
Matt looked sullen but undeterred, “I’m sure tons of women are apprehensive at first…”
Maddy’s mouth went agape, but she was smiling, “Touché… BUT, it’s still John’s choice, within reason, remember we agreed: nothing permanent, no pictures, no tattoos, nothing that’s going to cause any long-term aches and pains.”
“Well, you told us you fucked that one dude in the ass for hours, and he didn’t complain!” Matt teased, “I’ll probably last ten minutes tops…”
“Hmmm, right. *The Pickleball guy,*” Maddy said wistfully, “he had a fucking fantastic ass, it was just meaty. You just wanted to rub your face in it. Sweet cock too. I had him folded up like a pretzel. Face between his knees. Numbing cream slathered on his cock. My nine incher buried in his ass. He had like five prostate orgasms… in like, the span of an hour. Made him swallow every load, too. It was fucking phenomenal. AND he could eat my ass like a champ…”
Maddy sighed, “I did I tell you guys …he’s a teacher now? He got married —probably has sex in the missionary position twice a week. It’s sad, man. Gentlemen, that man was a King. I can only aspire to be so freaky.”
Maddy extended her hand gripping her beer and she and Matt clinked the necks of their bottles together before they each took a swig.
“You guys are hilarious,” John laughed.
“What? I can respect a fellow pervert,” Maddy answered with a smile.
“So, we’re doing this right?” Matt asked, clearly feeling vindicated.
“Should I text Michelle?” Trevor asked a little unsure.
“NO,” Matt and Maddy shouted in unison.
Matt and Trevor continued to argue whether it made sense to potentially break off his relationship or to ask about *opening up* their relationship via a text message.
While their friends were distracted Maddy scooted in close to John whispering low enough so only he could hear, “Now, you chose to do whatever you want, but I think you should keep me to yourself… We can do ALL things you’re too embarrassed to ask about in front of the guys.”
Her warm breath tickled his neck. She clung to his arm and began to peck at his jawline. “No pressure,” she whispered between tight-lipped little kisses.
It was her subtle way of suggesting that maybe he *wanted* to be pegged.
“Why make this whole thing a spectacle?” John whispered back.
Maddy shrugged, “I thought it would be kind of exciting if they knew.”
Trevor conceded that he would, “it would be better to break it off with Michelle in person if anything happened tonight,” and both he and Matt turned their attention to John and Maddy.
“Well?” Matt asked expectantly.
“Johnny-boi won fair and square. I’ll honor our bet, I’ll do *whatever,* he wants,” Maddy said with cocksure conviction.
“Whatever, YOU want…” She repeated with a whisper into his ear.
John felt dizzy. His cock was buzzing.
“Down on your knees,” John commanded, though his voice was soft and wavering.
Maddy looked surprised, but she said nothing, no curse or smart quip, she only complied. Obediently slipping from the couch to the floor, kneeling between his legs. Her elbows gently rested on his thighs. Her fingers bridged beneath her chin.
“Now what?” She looked up at him, her straight brows raised, a small but welcoming smile on her lips.
Matt and Trevor were dead quiet, everyone was hanging by his next word.
Then John felt his phone buzz in his pocket.
John’s heart seemed to stall as he reached for his phone, he glanced down at the message and smiled.
“Turns…” John announced, “but, I think it’s only fair we invite Steven too.”
Source: reddit.com/r/eroticliterature/comments/11lftpv/down_a_peg_mmmfmidtolate20srough_draftopenended
Updateme!
Updateme
!updateme
❤️😈