I initially posted this around the 20th of October as a sort of casual posting of a oneshot on a random night. Big mistake - got flooded with spam on my reviews page, had to delete the story to make it stop. Pretty sure you noticed my profile is different by now, and it's related to the insanity that's been going on around the site. Hope to god this doesn't happen again as I post this one more time. Besides, I might be taking a break from FFN for a little bit, so take a look at my Archive Of Our Own profile (of the same name) for any potentially new or updated stuff for... maybe the rest of the month, I dunno how long this whole deal's gonna take. Also, stay clear of directly checking out other users' profiles, because you might end up afflicted by the same stuff I did. So enjoy my 60th story, and please be careful.
"I don't want to do this."
"Oh, c'mon Rocky baby, it'll be fun...!"
There was always going to be something to be regretful for when it came to dating a sexy pirate bombshell like the notorious Bonne Jenet. Sure, she was quite the looker, but it was too often where that was outweighted by the negatives. Sometimes she would be up to no good – thievery, petty scams, otherwise little greed-fulfilling plots, as you'd probably expect from a pirate of almost any kind (and often successful, too). Other times she would be gallons too deep in booze to function properly, and her drunken stupidity could sometimes intertwine with others who didn't want any part of what she was having.
This was closer to Column B for what she had dragged Rock into this time, but not exactly too deep in that column compared to earlier incidents.
It was only meant to be a hang-around at a casual party, but one trip to the bathroom later, and the odd couple had wound up staring down into a hole in the wall of a stall.
Jenet kept her arms wrapped around 'her bae' as she liked to say sometimes – although she didn't seem too buzzed, there was no doubt her mind was still circling around if she thought this was a great idea to spend time at the party. "Alright... how about a little wager then?" Her hands lingered lightly around Rock's crotch as she explained, "You, let your goods free for just this once, and give that little glory hole a try – if you last about, let's just... *urp* say three minutes before... y'know... I'll pay ya $10 for your time. If you don't, you owe me."
Rock wasn't really willing to accept when just a light bit of cash was on the line. He was often above the petty bets. "That... doesn't sound all that great of a bet."
Jenet's cuddle from behind grew slightly tighter around the Wild Wolf's protege. "If that's how you want it – how about, if you keep it together forthe three minutes, you get the loot of $10, and," she leaned in closer, "I get to suck you dry myself."
The wager suddenly did get a bit more enticing – a little bit of loving from the seductive freebooter was almost irresistible with how her sex appeal kept a latch on whoever was close to her; again, almost irresistible, given the only implication was some oral pleasure, but there was still maybe a chance it could go further than that.
After a reluctant sigh, Rock began to go for the zipper on his black jeans. "There's probably not even anyone there..." He secretly wanted that to be the case, even if it was a bit of a back-down.
His penis inched through the hole, up to the base, with much space to spare, and hung freely in the next, thankfully closed, stall ahead. For a moment, it really did seem like no one was there to partake, but after about ten seconds, he was greeted with the feeling of a set of fingers grooming across the tip. He immediately began to feel himself rising and hardening so slightly as the anonymous hand began to fondle and tease him.
A light blush of red came over his face, as he glanced towards Jenet. "Ungh... so when does the 'three minute' thing start?"
"When she starts suckin'." Quite an honest answer out of her.
That and the timing could not be any more fitting, as the tingling of a pair of lips pressing against and taking in the first inch of Rock's member elicited a sharp gasp from him. He nearly smacked against the stall wall with both hands and bent his body back as the mouth on the other side took in even more of him. Too late to back out now...
Jenet squatted to meet the hole more eye-to...hole as she saw her BF's cock poking through and his hips wiggle lightly. Upon hearing the increasing volume of slurping noises from the other side, she licked her lips and giggled with some sexual intrigue.
Rock's bottom lip brushed across his teeth for a bit as he attempted to keep his composure. He gripped onto the top of the wall to keep himself from being too spastic with his movements while the suction on his cock began to intensify rather quickly. He almost wanted to thrust forward to give the nice sucker a little more to bargain with.
However, he didn't know if he even needed to push at all, as it seemed like the person on the other side had him covered, pressing their mouth forward so that he could feel his cock reach their throat to the point of nearly choking them. He was imagining as if Jenet was the one sucking down on his penis right down to the base, moaning and gagging simultaneously while deepthroating him, and looking drop-dead gorgeous doing it. It seemed like a bad omen to do so when the task at hand was lasting long enough to secure a (mostly unwanted) victory in the odd little bet, but it was too late now.
Way too late.
Not long after imagining that thought, the feeling overwhelmed him. He bit his bottom lip nearly to the point of bleeding, and his hips pressed hard against the wall while that sensation flooded over him. His cock throbbed intensely, and the ropes of cum pouring out of him immediately met a home, nesting in the mouth and throat of the eager partner on the other side.
All the while, Jenet watched the erection of her fellow blonde throb as it nested through the glory hole, and she giggled in amusement – although not entirely from the enjoyment of spectating the finish of her boyfriend's first anonymous blowjob...
Rock took a moment to breathe deeply once the load finished and the partner let loose of his cock with an audible 'pop!'. Glancing down at the pirate with a twinkle of hope on his mind that the moment was worth it, he asked, "So? Was that three?"
Jenet had her phone on stand-by to record the length of the experience, and with a glance at the stopped time, she looked up with a faked tone of disappointment. "Not even two." A minute and twenty-six seconds, according to the timer. Not even halfway.
Rock knew from the start that this was a bad idea, given his track record with the ladies, and his light fears were unfortunately true. After tucking his member back into his rezipped pants, he begrudgingly handed the babe ten bucks straight from the pocket. "You're the worst. I'm gonna go get a drink..." He walked out with a mild feeling of embarrassment, leaving his girlfriend with her 'earnings'.
What he didn't know was that there was a little bit more when it came to this whole 'glory hole' setting that they had stumbled upon.
Well, what he stumbled upon. Jenet had already found out about the glory hole ahead of time, and from the looks of things, the person on the other side was apparently in kahoots with her in some fashion.
Also, that person? It wasn't a lovely lady like one would expect (and what Rock was hoping for) – but a cute guy with a feminine, almost gender-ambiguous look to him. He didn't seem supremely satisfied as he gulped down the load that remained in his mouth, but he looked interested with her regardless. "You certainly have a way of getting your entertainment, mademoiselle."
"And now I know you don't back down on anything, Ash." said Jenet. For a guy she had only met moments before all this, was pretty impressed with his keeping of his composure. She waved her achieved $10 at him.
Ash halted her. "Ah ah ah... I've done my part – double or nothing says you can do the same."
Jenet was taken off-guard. "Whoa. You're trying to negotiate against me? ...I like your style. Step aside..."
The greed on her mind when it came to these upscaling bets was not subtle. She promptly began to trade places with Ash, taking a seat on the toilet and closing the door on him. May whoever comes next take a try at the pirate's mouth for a good time... and a guy did step up.
A particularly chubby, slobby and hairy guy, no less. "This where the blowjob hole is?" He asked, not even bothering keeping his voice toned down given the circumstances.
Ash chuckled at the sight of the big guy. "Go right ahead." He was quickly imagining what Jenet will think, considering who she was going to deal with, and the thought of it was hilarious.