Disclaimer: This text depicts a chronically insatiable young woman's pursuits to find impossible satisfaction, and they involve detailed depictions of the dangerous, overtly uncomfortable and painful ways she goes about it. Consent definitely becomes blurry and there is depiction of coercion into breaking her boundaries.
Infinite thanks to firmbutgentle, who kindly edited this story, and who is the author of one of the most beautifully written BDSM series here.
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She was no stranger to the joys and perils of sourcing sex partners online, though it's not that it was her only option. A young professional, attractive enough to be offered free drinks at bars, to feel eyes caressing her curves on the short commute after yoga and in sundress season, she knew better than anyone that there were dependable hookups out there. They were ready to materialize whenever she bit her lip while sustaining eye contact for a couple seconds, whenever she started toying with the strap of her top.
She also knew that people like her seldom find satisfaction with the drunken Chad at the bar or the friendly Joe from her friends' friends' party. Sure, there were times that the predictable choreography of cum for dinner after her single orgasm around a rando's cock was a fine way of spending a Wednesday night, a worthwhile pursuit. But a freak could not live on that alone.
A freak in the sheets is how she thought of herself. She knew she was a slut in that she was willing to go to bed with most anyone, no matter the wedding rings, the age gaps, or the number of cocks in the room. She knew she was a bit of a nymphomaniac, used to weeks of waking up in five different beds -- she could be a freelance bedding and bedroom decor consultant by now. She was a whore, too, and she was always aware of the way her deep throat and her bubble behind earned her the handful of luxury items that adorned her otherwise fast fashion closet.
Still, she knew that sex volume alone could not tame the constant burn in her insides, the deep need to spread her legs and wrap herself tight around someone else's strong fingers, her throat constricted and her mind tricked into finally feeling that enough is enough. This is why she was a freak in the sheets: she needed to be surprised, to be pushed, to be edged. She came hard whenever she was manipulated, whenever her pussy was confused between pleasure and danger.
That was the reason she spent Friday nights in her own bed, often wearing some of her best lingerie, her toys scattered around her and her laptop. By now, she had perfected the workflow to most efficiently browse the personals in her area on a few different platforms. When no one new or interesting popped up on the kink website, she browsed different subreddits. More often than not, she found a married daddy looking for submissive cocksuckers, always a great option for some well-earned hotel carpet burn on her knees that would last a few days. She also had a predilection for the archetypical mid-thirties creative looking to spend time exploring all orifices in all ways before the grand finale -- their pursuit to overcome their own boredom made up for their dwindling stamina.
Each night of browsing brought a parade of cocks and evidence of their escapades, with a few candid shorts mixed in -- hence the toys she kept around her. She easily made herself come a dozen times while looking for the lucky guy whose inbox she would visit, the one who would not be able to resist a profile with faceless pictures of her body in different states of use and misuse. But no matter how many times she pressed the vibrator against her clit, or the vibrating Ben Wa balls into her holes, those solo orgasms only fed her sexual hunger.
Perhaps with a cooler head and less oxytocin in her bloodstream she would have been less vulnerable to one of the seemingly lowest effort, most cryptic ads of the night. "35 [M4F] Looking for some fun of the hole-wrecking kind," the promising title read. She immediately clicked to find the most disappointingly redundant single line: "I'll use your holes. I can host. PM preferred."
This was the kind of message to which she'd seldom respond simply because she needed more material to work with, more information to assess the suitability and the safety of the pursuit. What if the concise request had been written by a morose lover, a pillow prince of sorts? What if it was the kind of message that could be authored only by a guy that does not believe in safe words? After all, it is true that she was desperate for satisfaction, but she didn't lose sight of the wet dream she embodied. She had learned to keep a burner phone just for sexcapades, now used to the management problem posed by past conquests that wanted seconds and fifths at any cost.
She and the anonymous 35[M4F] had something in common, however: they both needed fun of the hole-wrecking kind. It had been long since someone had fucked her so hard she hurt for days, and it sounded like just the right thing to finally bring lasting satisfaction, to fill the seemingly permanent and sometimes acute void in her insides. She really needed to focus on a challenging work project for a couple of weeks, so she somehow processed this message as a probable win-win despite its raising all sorts of red flags.
It was fair game, wondering what he really meant when he said that he wanted to wreck someone's holes. It could be shorthand for one of the most overused descriptions in online porn, present both in perfectly vanilla missionary tapes and in massive cock gangbangs that make porn actresses whimper before they're warmed up to the sizes. But the question, really, was what it meant for her.
Was hole-wrecking a proxy for repetitive sexual stimulation that would build her pleasure over hours until she finally reached a big, enduring O, especially if it involved persisting through the associated damage and discomfort? Was it a form of fucking so deeply pleasurable she could not describe it beforehand, the kind of all-encompassing experience you understand only once it's made you surrender to it? She was curious to find out, so the short personal earned a one-line reply: "I just want to have all my holes used in a hole-wrecking sort of way."
She didn't close her laptop, but she did get up from her bed to get ready. It was time to start the self-grooming routine that her body had long memorized, all because she was confident enough that she had found this weekend's suitor. If her holes were going to be wrecked, they needed to be spotless, soft, freshly shaven. Some body exfoliation and toenail polish were surely not on the list of priorities of the guys looking for pussy, but she believed in investing in her image. After all, she had the theory that guys went harder on pretty little things -- they loved wrecking her beautiful made-up face, they loved bruising her breasts under their beautiful lace, and they loved pounding her pussy harder after running their tongues over her smooth, plump lips.
She was wrapped in a robe, fixing her hair when she refreshed the page. She was so confident going into this that she felt no flutters, no excitement, when one notification popped up. It was to be expected, and she needed more time to complete her routine.
"I can see you have experience with that. It is always a pleasure to find (or be found by) experts in the matter at hand.
Dinner and drinks at Yvonne's?"
She had a general disdain for the formulaic rituals around the hole-wrecking, but she knew they were a part of the job. Plus, even if she responded now, she would still have time for the red lip and the hosiery before it were time to take a cab. The only part that didn't quite fit in was the venue: Yvonne's. An upscale, trad date spot did not seem to be the most fitting prelude to debauchery, but she was game.
"What time?"
