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Please see Part One for tags/warnings.

***

ADMIN.MONTH 8

***

The mirror was incorporated into all of Toni’s morning tasks going forward.

This particular morning, she was seated against the foot of her bed, naked, using the dildo to edge herself. She wasn’t allowed to insert it; Admin rarely allowed that. He had instructed her just to tease herself with it–grind her clit against it, work the head of it against her aching hole, squeeze it between her thighs and hump into it.

She’d already hit the edge three times, and Admin had just instructed her to continue each time. It was a Saturday, so there was no limit to how long he might keep her there, slowly reducing her to a dripping, throbbing mess in front of the mirror.

“Please,” she sobbed, spreading her legs wide and staring at her own swollen pink hole in the mirror as she rubbed the rounded head of the dildo over it. Her cunt clenched, hungry with the memory of being stuffed full, of squirting all over that same toy in a fountain of relief. “It’s been four months, Admin, please…”

_Please what?

“Please let me come!”

_Let you come how, missy? You’re not allowed to come like that, are you?

Toni chewed her lip, trying to think through the fog of need, while also trying to track the closeness of the next edge threatening her so that she didn’t go over and ruin. “Um…I don’t…mmm…”

_You can only come on my cock. Remember?

She nodded, then groaned as she finally figured out what he wanted her to say. “Please, uh, please l-let me ride your cock and come on it?”

_Good girl.

_Keep playing with yourself for a moment, let me set something up.

Toni sobbed and rolled her hips, grinding her clit along the length of the toy. The sharp need built, and built, and then she hit the edge and pulled away again, shaking and whimpering, staring at the pitiful mess looking back at her in the mirror as she watched her own pussy clench and wink.

Admin finally messaged her again:

_Alright, missy, enough touching.

_Go take a cold shower, and wash the toy while you’re in there.

_And I mean COLD. Spray that naughty little pussy of yours to get it calmed down.

Toni climbed obediently into the shower. The cold spray was uncomfortable, and it was an odd sensation when she sprayed between her legs–stimulating but numbing at the same time, leaving her awfully empty-feeling and achy, hyper-aware of how the inside of her pussy felt feverishly hot and swollen by comparison.

Once she climbed out of the shower and toweled off, rubbing herself briskly to warm up, Admin began messaging her again.

_Here’s how this will work. I’m going to give you 20 minutes to come as many times as you want, but you have to follow these two rules.

_Rule 1: You may not touch your clit. You will come only from fucking yourself with my cock.

_Rule 2: You can only put it inside you once you’re somewhere public. Either outside, or in a public building.

Toni gasped and shook her head. “No. Oh, no, no, I can’t–in public? I can’t do that!”

_Then I guess you’re not coming today. Your choice. I don’t plan to give you another chance any time soon.

_I’m switching off The Ruiner program and starting your timer now.

_If you break either rule, I’m switching the program back on immediately.

A timer appeared in her interface–20:00, it said–and immediately began to count down.

Toni gaped, her fingers curling on the marble edge of her bathroom counter, as she watched the seconds slip away.

“No, please, not that–Admin, please, anything else, just not in public!” she begged.

_I don’t know where you got the idea that this was a negotiation.

_Tick tock, missy.

Toni bit her lip hard, squirming in place, and then groaned desperately as the timer ticked down to 19:30.

“Fuck,” she gasped, and then pushed away from the counter and scrambled for her dresser, digging out clothes to wear.

In a panic, she haphazardly pulled on panties, bra, and a loose shirt, and then a knee-length skirt–for easy access, she thought, blushing wildly.

There was no way. There was no way she was going to do this!

But he said she wouldn’t get another chance for a while…how long would that be? Another four months?!

She emptied out one of her bigger purses and tossed the toy into it, along with a change of underwear–almost by habit at this point–and only at the last second remembered to add her keys.

As she rushed out of her apartment, the timer was already ticking down past 15:00. She bit back a whimper of desperation.

There was a park across the street from her building; that was the first public place she thought of, the place she could get to the quickest. She hurried across the street and then made a beeline for the public bathrooms on the far end, because at least that way she’d be sheltered inside a building.

Admin began to message her again as the restrooms came into view.

_Good thinking, missy.

_Don’t worry, a public bathroom counts. This time, at least.

She picked up her pace, practically jogging, as the timer counted down to thirteen minutes and then twelve. She rounded the squat little building marked with the bathroom signs, and–

OUT OF ORDER, read the sign on the women’s bathroom door.

“No,” she gasped. She tried the door anyway, but it was locked shut.

_Whoops. Better figure out something else.

Toni looked around frantically as the timer ticked to eleven minutes.

There was another building a few feet away, a utility shed or something like that. The door was clearly padlocked, but there was a tall, thick bush growing along one side to partly hide the building from view; a hollowed-out space under the bush was littered with nip bottles and other trash.

Just the idea of masturbating outside was enough to make Toni blush, especially in such an illicit spot, but–the bush was thick enough to hide her from view, and the timer ticking down in the corner of her vision left her with no other options.

She hurried over, trying not to look too suspicious as she slipped behind the bush. It was a Saturday, and despite the cool autumn weather, she wasn’t the only one in the park; nobody was within hearing distance, but she had spotted a couple walking their dog as she’d hurried through, and a man near the fountain.

Toni pushed them all out of her mind as she burrowed her way into the dimly-lit nest created by the bush. If she thought about being discovered, she’d be too anxious to get off, and this would all be for nothing.

Her hands were shaking with adrenaline and need as she opened her purse. It took a moment to figure out how to arrange herself–a moment that she didn’t really have; the timer was under ten minutes, now–before she ended up crouching with her back pressed against the shed, her knees spread wide. She yanked up her skirt and pulled her panties aside, a flush heating her cheeks as she thought about what a picture she would make if anyone saw her like this, and then she carefully pushed the toy up into her dripping pussy.

“Ah,” she gasped as soon as she felt the delicious stretch of it, and she had to drop her skirt to clap a hand over her mouth. “Mmm. Hnn…” Her knees quivered as she pushed the toy in and in, stuffing herself full, filling up her hot, needy cunt. Her body remembered the shape of the toy well, clenching impatiently around it, already anticipating the explosive release of pleasure that the dildo was associated with in her mind.

_Good girl, missy. Good little slut.

_Fuck yourself on that cock. Don’t hold back, you don’t have much time left.

Toni began clumsily working the dildo into herself. The enclosed little space became filled with quiet, wet noises and her strained whimpers, muffled behind her hand; it was awkward to work with her skirt hanging down, but she couldn’t hold it up when she needed one hand to gag herself.

In spite of the discomfort and strain of squatting, the pleasure was exquisite. Her eyes rolled back in her head as she plunged the toy into herself over and over, a wave of dizziness washing over her as she panted through her nose. Her clit ached and begged for a bit of help, letting her know that just a brief touch there would be enough to send her over the edge immediately, but she couldn’t, she couldn’t…

5:15, read the timer.

She groaned into her hand and rocked her hips, working herself hard on the toy, until she finally found the angle that made her feel like her orgasm was in reach, grinding into the spots inside of her that made her light up with pleasure. Her clit twitched again, and she choked back a whimper of desperation, wishing she was just allowed to touch–but it was coming, her climax was creeping closer and closer with each wet slide of the toy.

Five minutes on the timer, and–she was going to make it–! She was almost–!

“Hello?”

A man’s voice, only a few feet away.

Toni froze with a stifled yelp. Adrenaline rushed through her, simultaneously icing her arousal while also making her squeeze down on the toy in a way that made her horridly aware of its thick presence inside her.

“Yeah, I’m at the park on Brown.”

Toni let out a hard exhale of relief. The man wasn’t speaking to her; he was on the phone.

But he was right there, standing just on the other side of the bush. She was lucky he hadn’t heard anything already. She couldn’t make a sound, or he’d hear, and…

Toni pulled the toy partway out of herself, then froze again at the wet sound that it made, and the way the slow slide against her hyper-sensitive flesh forced her to swallow back a groan.

_Bad moment to get stage fright, missy.

_You don’t have much time left.

The timer was still counting.

No. She couldn’t–with a stranger standing right there–! There was no way she could stay quiet while she was coming, not in this state!

3:00. 2:59. 2:58.

Toni shook her head frantically, trying to think of a way to communicate to Admin without speaking, to beg him to please pause the clock, please, just until the man walked away–!

But, with a wash of despair, she realized that even if she were to ask out loud, Admin would just say no.

The man’s shoes crunched on the leaves as he paced back and forth on the other side of the bush. “Sure. Did you want to meet for lunch?”

Toni let out a thin, pitiful whine through her nose. Her pussy, wet and spread open on the toy, clenched and rippled, reminding her that it was just moments away from a massive orgasm.

_I’m surprised by your self-control, missy.

_Weren’t you just crying and begging me to let you come? And now you’re wasting your chance, just because you’re embarrassed that someone might hear your squealing?

She shook her head desperately, eyes filling with tears. It wasn’t a matter of might; she remembered her own cries last time she had come, echoing off the walls of the shower, the primal screams of pleasure as she had finally–finally–

Her cunt pulsed again, just the memory drawing her even closer to the edge, and she let out a quiet, tormented noise.

Oh, God, she needed to come so fucking bad–but if this stranger heard her, she was going to absolutely die of shame and embarrassment.

“Yeah, I’m like a block away from there. You want to meet now?”

The clock ticked down. 1:30.

Toni choked back a sob. Go away, go away, PLEASE go away…

The man’s shoes crunched on the leaves again, taking a few steps away.

Toni’s heart skipped a beat with anticipation. Yes, yes, he was leaving, yes–her pussy rippled and then drooled an embarrassingly large glob of slick fluid down the cock wedged inside it as her hand trembled, preparing to fuck herself hard and fast, just as soon as he was out of hearing distance–

His footsteps returned.

Toni squeezed her eyes shut.

0:45.

_Guess you didn’t need to come that bad after all.

“Yeah, alright. I’ll wait here.”

The clock ticked down to fifteen seconds, then ten.

Tears dripped down Toni’s face as she watched the time slip away into nothing, until there was nothing but a big 00:00 across the darkness of her closed eyes. Her pussy, stupid and eager, continued to throb.

_That’s it. I’ve turned the program back on.

_Oh, you poor, silly little slut. I almost feel bad for you.

_It’s that virgin shyness, isn’t it? We need to work on that.

_There’s no point in you being shy. Your body and pleasure both belong to me.

_It doesn’t reflect on you at all, you know, if some stranger finds you fucking yourself on my cock and squirting in the dirt behind a bush like an animal. That’s just how I want you. It’s my choice.

Toni watched the messages scroll by in a numb haze of despair. Her cunt clenched again on the toy, still anticipating the release that she’d been preparing for, that she needed.

The release that she wasn’t going to get.

It was another few minutes before the stranger lingering nearby finally walked away, far enough that Toni felt comfortable pulling the cock out of herself. The toy was absolutely drenched in her fluids, and she felt open and empty without it, abandoned. Her face was damp with tears.

“Please,” she whispered, gripping at her thigh with her free hand. Her whole body trembled with the acuteness of the frustration burning inside her, four months of unsatisfied lust roiling in her blood.

_Are you asking me to change the rules, missy?

_I never, ever go back on my word.

_Don’t worry. You’ll get other chances.

_Not today, though. I guess we need to let you get a little more needy first. But eventually…probably…you’ll get other chances.

Toni took some time to feel sorry for herself, crouching there, her pussy drooling into the dirt and tears tracking down her face.

Eventually, she shoved the toy back into her bag and pulled herself to her feet, and then stumbled her way home, keeping her face down so that people wouldn’t see the blush in her cheeks or the wetness in her eyes.

***

ADMIN.MONTH 10

***

Two months passed in a haze of aching need.

Toni’s concentration took a sharp dip. She found herself unable to focus on anything for more than half an hour at a time; her mind was constantly dragged away by the empty space between her legs, the wetness and the burning desire to be filled.

She made a few weak attempts to try and convince Admin to let her come, mostly by voluntarily fucking herself down on the toy–his cock–right in front of the mirror, keeping her eyes open wide so he could see each inch of it disappear into her hungry cunt.

Admin knew what she was doing, though, and he just laughed at her for it, calling her an eager slut and a quick learner.

He began sprinkling some different material into the porn and erotica he showed her, too. He started to expose her to media about casual encounters, first times…a video of a woman losing her virginity; an erotic story about a woman experiencing her first orgasm after going home with a stranger.

Toni knew what he was doing–or, at least, she wanted to think that she had a good idea. Still, she didn’t know exactly what to expect, or when, so it came as a rude shock when one Saturday afternoon he interrupted her idly rubbing herself in bed with a message:

_Tonight, you’re going to go out and find a man to fuck you.

_We’re going to cure you of this virginity nonsense.

“Wh-what,” Toni squeaked, her hand squeezing impulsively where it had been lazily curled against her wet sex. Her cunt pulsed in return, and though she wished she could pretend it had nothing to do with what Admin had said, there was no point in lying to herself.

_You’ll go to a bar and find a man to service.

_Don’t worry, I’ll walk you through it. And I’ll be watching.

She swallowed, hard. “And then will you…will you let me…?”

_No, of course not.

_You only come on MY cock, remember?

_But this is the next step in earning yourself an orgasm. You won’t like the consequences if you disobey.

And so, a few hours later, she left her apartment dressed in the only clothes that Admin had deemed appropriate for the task: a skirt so short that she typically only wore it with leggings underneath, and a shirt that had once belonged to a former roommate and was two sizes too small for her, baring her midriff and barely holding her breasts. Leggings and bra were both vetoed, but Admin allowed her to wear panties, at least.

He let her choose the bar, and so she went to one only a short bus ride from her apartment. She’d only been inside once before, when some other students had invited her out to celebrate after final exams one year; since then, it had apparently been turned over to new ownership, and the cozy tavern she remembered had been refurbished into something a little more hip. There were a lot more people there than last time she’d been, too.

As she walked into the room, several men turned to look at her. Toni shuddered, not used to the attention.

_Of course they’re looking. I bet you stink of pheromones.

_A woman starved of orgasm for half a year, so hungry for cock she’ll fuck herself with a dildo in front of a mirror. They can all smell it on you.

Toni hoped the dim lighting hid the mortified blush in her cheeks.

There was a drink minimum, so she ordered a mocktail at the bar–reasoning that getting drunk, or even tipsy, would be a terrible idea–and found a spot out of the way to stand and sip it, trying to steady herself, even as Admin continued peppering her with filthy messages.

_We’re looking for a man who looks rough, but not dangerous.

_Someone who’ll take you out back and rut you in the alley.

_This is about breaking you of the notion that your virginity is something special, something you need to hold onto.

_Don’t you remember losing control on the bus in front of all those strangers? You’re nothing more than a common slut, really. The only thing special about you is that you belong to me.

_I’ll do you a favor, by the way, and turn off your sensitivity down there.

_Totally numb. You won’t even ruin.

_That’s just for you, because you’re being such a good, obedient whore.

Toni shuddered and chewed her lip, looking around. There were lots of men around–lots of women, too, but the men certainly seemed to outnumber them, and while the women mostly seemed spoken for, plenty of the men were on their own or in little groups.

_Spread your feet a little further apart. Advertise what you’re looking for. No need to be subtle.

She blushed and took another sip of the sugary drink, and then slid her feet apart until she could feel air between her thighs.

The underwear she’d put on were already embarrassingly damp, she could tell from how the air cooled the fabric. She felt ridiculous, standing that way, and looked around briefly to be sure nobody was laughing at her–

–And found herself locking gazes with a man who was. Well. He certainly wasn’t laughing.

Toni’s face flushed hot as the man looked her pointedly up and down, his eyes catching on her short skirt and the gap between her thighs.

When he detached from his group of friends and started to make his way towards her, she panicked and put her drink down on the bar, thinking about getting away–but then Admin chimed in.

_He’ll do.

_Bet he’ll fuck you dirty, the way you deserve.

Toni shuddered as her traitorous, desperate cunt clenched at the words, seeping more wetness into the fabric of her already-soaked underwear.

“Hey,” the man said, and Toni squeaked in surprise. He laughed. “Sorry, didn’t mean to startle you. I thought you wanted me to come over…?”

“Yeah. Um, I mean,” Toni stuttered, trying to listen to him and read the messages scrawling across her feed from Admin at the same time.

_Better seal the seal.

_Don’t chicken out now, or it’ll be a good, long time before I’m in the mood to let you try again.

“Uh.” She forced herself to look up at the guy. “Yes. I did. Want you to…to come over.”

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