"I'll Use Your Holes," The Ad Said

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.

----

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?"

She devoted a few minutes to curating the perfect set of lingerie -- not too fancy, definitely purchased in the annual sale and easy to replace in the case of wreckage, comfortably in the category of what she would describe as 'refined slutty' with see-through demi cups and playful panty and garter lines across her lower belly. This would all fit perfectly under the discreet LBD, the little black dress that would demurely highlight her collarbones and her waist while blending her into the vanilla background at Yvonne's. No one else had to know just how badly she wanted to be slapped and called a filthy slut that night.

"When would work best for you?"

She left him on seen to complete her outfit with a careful cat eye, a bold red lip, and stilettos. Jasmine perfume, pearl earrings (but not the necklace) gifted by a sugar daddy who loved to come all over her face and push it into her mouth with his fingers -- she was ready to look like a good girl who secretly loves to behave very badly.

So far in life, keeping a demure appearance even on her way to sin city had been key to keep her darker secrets under wraps. Every Thanksgiving, her aunts would ask about a boyfriend, and she'd say she hadn't met anyone good. "Maybe you should relax your standards a little," they always said, oblivious to just how relaxed they were every time she let strangers take turns on her in swinger parties. "Maybe I should," she always said, wondering what her aunties would make if they ever knew just how much sperm their girl-next-door niece had swallowed.

"Well, I'm on my way now. I will be at the entrance in a black dress, but I guess you already have seen enough to recognize me."

For a minute, she wondered if he had. Her profile had been curated to highlight her sexual preferences while hiding her identity. She had to blindly trust that he'd recognize her hair, her lips and her long neckline from the photo taken from above while on her knees, proudly displaying the cum that adorned her after sucking off what could only be a group of men. If he had a good eye, he might even make out the bruised curves on proud online display under the structured silhouette of her dress.

She closed the laptop and called a cab on her burner phone. She didn't need to wait for his response to know that he would show.

--------------------------------

The emotions began to kick in only when she got off the cab with a first-date heartbeat, realizing she would be identified before he would be. She only knew she was looking for a guy in his mid-thirties, but Yvonne's was Friday night date central for those who had someone to impress. She started her internal pep talk, telling herself not to react dismissively if she were approached by someone whose looks did not attract her, or if he had odd manners or a wedding ring. She prepared herself for the possibility that the conversation would be anything from awkward to boring.

She worked herself so hard to land on her feet if her fears materialized that she completely failed to prepare for the unexpected. And, before she knew it, she had been standing at the entrance at Yvonne's for fifteen minutes. Two different waitstaff had already asked her if she was on the list already. A handful of couples had already passed her on their way out, ready for their own nights of fun. Against all odds, everything indicated she had been stood up -- a rare but major blow to the beautiful freak's confidence.

She began to scan the people at the busy restaurant lobby, wondering if it was time to save face and exit with dignity before others realized what had happened to her. Dressed to impress and ghosted, the ultimate first date nightmare come true. Call it confirmation bias, but the sad way the hostess looked at her, the silent app notifications despite several refreshes -- it all got to her and she knew she had to leave.

She was so caught up in her crumbling internal world that her mind failed to process the persistent obstacle between her and the door, a person she tried to sidestep a couple of times without success. This was not the night for clumsy clashes, but it was almost like he was anticipating and blocking her every move. The urban equivalent of walking through sinking sand. Despite her tall, taller in heels figure, she felt small, unseen.

"I'm sorry," she said, culturally trained to apologize in awkward situations that weren't her fault but still needed to be softened.

She looked up into his eyes when he remained silent, and he was oddly relaxed for someone trapped in an awkward moment. Eureka. It was him -- it had to be him. Except it couldn't be, because he would have approached her, right? She opened her mouth to say something, but words escaped her.

He smiled placidly, letting the awkwardness float for a few more seconds, relishing in the feeling that comes from staying on your feet when everyone else has fallen.

"It's our turn. The hostess just called us."

He had been there long enough to get a table for two without reservations, and she had failed to realize this. How long had he been watching her? Was he privy to her increasing impatience, to the internal meltdown when she thought of herself as ghosted?

With everything sorted out, she was still unable to get up from the psychological floor. She stood in front of him, still silent, still awkward. The script had been changed on her and she was having a hard time improvising. So much for being a confident freak, a vixen with ample experience, a young cougar always ready to pounce.

It was masterful, the way he leveraged this spontaneous? manufactured? window of opportunity. With his hand on the small of her back, he turned and guided her towards the smiling hostess, keeping her close and further establishing a soft power balance that favored him. She had never wanted to be a docile date, a damsel in distress waiting to be rescued by a strong man, but she found herself walking at his pace, sitting at the table only when he pulled the chair and motioned her.

Nervous, she fixed her hair once, concealing a deep breath by holding it in in the same belly that hosted the desire that had brought her here in the first place. It was time to get up from the ground or be eaten alive. She smiled at him as he sat down, his demeanor relaxed still, even when he was aware of the ways she was taking in his shape and dissecting him in an attempt to understand this unexpectedly prepared counterpart.

"I'm sorry about that, I didn't realize you were here and I was trying to think through what I should do next," she smiled, trying to smooth over a start that had painted her in a less favorable light.

"No problem, but now I'm wondering what your next steps were going to be."

Mistake number two. She had set another trap for herself, and she was grateful for the waiter that rescued her with the delivery of two short menus printed in high quality paper. She hoped to buy time by sticking to the social script of salad with protein while he would surely read and deliberate -- but there was no such relief. He thanked the waiter but his eyes never left her, as if giving her time to respond to his point.

"I wasn't sure," she confessed, but it was time to rise. "But it doesn't really matter now. I'm glad this worked out in the end."

She was back. Her doe eyes focused on his for a few seconds, unafraid, her smile still on.

"Have you been here before? Do you have any recommendations?"

He finally broke eye contact to glance at the menu, his hand running through his short beard.

"I do, actually, but my experience tells me you're not here to be surprised by the food." He set the menu down on the table, his palm holding it down, as he returned his eyes to her. "Are you a two-appetizers and fries person, are you the one who always orders salad on a first date?"

She returned his smile, busted, but he had no way of calling her bluff. She moved her hand to his menu, her red nails tracing a single line against the hand of his that rested there. She had never been a brat, and she didn't go around causing trouble while secretly hoping to be swept off her feet. Still, he had created the perfect opening, and she was more than willing to let herself in.

"That's a little presumptuous," her eyes traveled down to the imaginary line she drew against his index finger for a moment. "Maybe I am here to be surprised."

--------------------

It would seem implausible after such an awkward start, but... You know those first dates so successful that the waitstaff cheer them on by perfectly timing the dessert menu and the bill, all because they don't want to kill a great vibe? This turned out to be one of them. For two freaks that were there as a forerunner to fun of the hole-wrecking kind, they certainly did enjoy an all-encompassing conversation that felt like a well-timed symphony spanning the shared appetizer, the two mains, the extra side, the shared dessert, and the digestifs. It's not that it was an easy musical piece to perform, as mutual tension kept erupting at different points before fading back into the background.

The conversation was so good that she was actually concerned. Not that she feared she'd fall for him, but rather that the built rapport would have a chilling effect on his darker explorations. Of course she wanted him to care about her, but not so much that he'd second guess if his thrusts were a bit too fast and too deep, or if his rough fingers were making lasting damage. It's difficult to find someone who will moan your name while holding your head down through the strongest spasms in your throat and the flailing of your arms -- the prosocial power of empathy had paradoxically been her biggest enemy in her wilder pursuits. Still, with every frank answer of his, she felt safe letting her guard down progressively, sharing glimpses of her fuller self.

It was when they were down to the last sips of port that he made the move she had been expecting all night.

"Listen, I still have a lot of questions for you, but the most burning ones are better suited for somewhere more... quiet."

Time to turn the tables again.

"I'm sure the bathroom is fairly quiet."

Eyebrows raised, he gave her the slightest look of disapproval as she chuckled -- one more round that went to her -- and especially as she raised from the table to head for the exit of the restaurant. She was ready for more of his questions, and to ask her own -- after all, she had gone in blindly, without her usual back-and-forth about safewords and other limits. She may have seemed a unicorn 'anything goes' freak, but in reality she was disciplined about only swallowing cum, rather than letting men fuck her without a condom, and he needed to know that.

----------------------------------

They were silent as they waited for the cab he called, ever the responsible drinker. Her anticipation was a mix of excitement and confusion -- she had responded to an ad expecting an untidy bachelor pad where a guy in sweats would lacerate her body mostly out of selfish roughness. How had she ended up on an adventitiously fancy date with someone who did not bore her out of wanting dessert? At this point, if the sex turned out to be underwhelming, she did not have a right to be mad.

Maybe this was the epiphany that released her -- or, coincidentally, the moment when the dining and wining mingled with the remnants of oxytocin in her system, helping her overcome her assertiveness, her discreet self-defense. She was no longer in need of being surprised. Instead, she felt genuine openness to seeing where Mr Bearded Self-Identifying Hole-Wrecker wanted to take things.

Still, the feeling was not entirely liberating. There was something unsettling about not being her usual Friday Sex Date Night self. She had cultivated an efficient protocol, a conducive demeanor, and this change in script was nice but challenging. The large hand that slipped around her waist, tapping slowly on her ass before pulling her closer to his side when they were inside the car was a reminder that the worst case scenario was not unsatisfying sex, but something much darker. She felt the little internal buzz in her clit that only meant her underwear would be growing damper.