Archive of Our Own

Chapter Text

Taylor was woken by the lights turning on. She kept her eyes closed, not that it made any difference to what she was feeling. The blanket felt far too warm, and her pussy and panties were soaked. She had dreamed of... of... the memories of her dream slipped from her grasp, but she was pretty sure they involved her getting dicked, somehow. Reluctantly, after a few more minutes of trying to defy reality, she opened her eyes and blinked several times. Even though she already knew what it was going to say, she brought up the tasks menu.

Before she had the chance to second guess herself, she picked the anal sex option, tossed the covers aside and took off her dirty panties. After hesitating for a moment, she did the same with her bra.

When the man arrived to take care of her ass, she was standing by the bed, and gestured for him to lay down. He tossed her a small bottle of lubricant, then pulled off his pants and laid down. Taylor caught the bottle and stared at it for a few moments, then moved to sit on his legs. She opened the bottle and poured a generous amount on her hand, then rubbed it all over his cock while jerking him off to keep him hard. She then slathered the rest over her asshole and took a deep breath. Taylor scooted forward and rose to her knees then, careful to line up his cock properly, slowly lowered herself on top of him, his cock stretching her asshole wide open. It still hurt, but not quite as much as it had yesterday.

Taylor closed her eyes and took a deep breath. She opened her eyes and took his hands, bringing them up to her breasts. As she started slowly rocking her hips back and forth with his cock buried in her ass, he started playing with her tits, alternating between squeezing and massaging them while using his thumbs to rub her nipples. Taylor forced herself to moan to show her appreciation. Doing anal still hurt. It was still uncomfortable. But she was horny enough that she just might be able to get off doing it like this.

His hands on her breasts felt heavenly, but grinding just wasn't doing much for her. For either of them, really. So she started riding him properly, pushing herself up and letting herself fall, plunging his cock deep inside. Over and over again, faster and faster, moaning like a two dollar whore. All too soon he shot his hot cum inside her ass, leaving her panting and whining as he grew soft inside her before gently but firmly pushing her aside and leaving.

Taylor hadn't gotten off. Her ass felt sore. She was, if anything, hornier than she had been before. Was she that desperate? Yes, she was. She hit the button again.

The second man entered while she was still laying down, catching her breath. He casually tossed his pants aside, then grabbed her by the ankles and pinned them above her head. Then he unceremoniously started fucking her ass. Taylor closed her eyes. It hurt, but... it was so close to feeling good. She awkwardly slipped her hands underneath her legs so she could reach her tits, and started playing with her nipples. She was so close, if only she could...

Unlike the first two, the man was not gentle with her at all, clearly only caring for his own pleasure as he fucked her hard and fast. Yet, as he came, so did she, moaning against her will as her asshole clenched hard around his pulsing cock. Her pussy, already well past soaked, squirted juice all over her face and chest, making her feel dirty and humiliated.

She didn't open her eyes when he pulled out. Or when he stood up and left. It took several minutes before she opened her eyes, still feeling her own juices on her lips and all over her face.

After staring blankly at the ceiling for a while, she rolled up to her feet. She took her clothes as well as the sheets from her bed and piled them in front of the door, and paid for laundry service. Then she went to get a long, hot shower and ordered breakfast while washing herself. Could she do that three more times today? To her regret, she suspected that she could. Should she? That was the harder question. Her ass was sore, but it really wasn't that bad. On the other hand, if she did it three more times, she would be sore all day, and maybe tomorrow as well. Definitely less than ideal.

Once she got out of the shower, she found breakfast tray waiting for her in front of the door, as well as fresh sheets and clean duplicates of her clothes, such as they were. She moved the breakfast tray onto the desk and gingerly sat down. Her ass burned a little, but it really wasn't that bad.

After finishing her breakfast, she put the tray in front of the door, finished changing the sheets, put on her bra and panties, and slipped on the heels. The xp for high heel training wasn't much, but every bit – that didn't involve her ass getting repeatedly reamed – helped.

An hour and half later, her feet were strongly disagreeing with her assessment. Taylor persisted out of sheer stubbornness, although she did compromise by leaning against a wall. Despite the pain, she was kind of starting to like how they made her hips sway, like she had actual curves. But not so much that she didn't immediately sit down on the floor and take the cursed things off when she got the Task Complete! notification. Her back had been starting to complain as well.

Unless she wanted to get fucked even more, there really wasn't much to do but wait for lunch. She spread her knees out and started massaging her feet. She hadn't really taken notice of it yesterday, but the extra flexibility she had been rewarded with was pretty nice. Even if the real purpose behind it was no doubt to enable more sex positions, or something equally perverted. She really was getting more acclimated to her imprisonment. Which was not a good thing, obviously, but... there didn't seem to be any point in getting worked up over it. Fuck, her life was depressing.

Theoretically, there shouldn't have been too much time between her taking off the heels and lunch. Practically, it was still enough for Taylor to get bored. Still, the menu for lunch finally opened in front of her eyes, and she quickly selected lasagna, since it was an option. It should be better, this time.

The lasagna was better. Still not as good as what her mother used to make, obviously, but not a complete disappointment, either. However good the lasagna was or wasn't, it was only a temporary solution to her boredom. She did, however, have plenty of perk points pooled and poised for payout, so she spent 100 pp to get another book loan.

The book started out promisingly, but the main character, a female ninja named Jin, spent most of her time either seducing people or getting captured. It was a decently entertaining read, even if it left Taylor feeling a bit frisky by dinner time. ...she could probably stand to get fucked a couple more times without feeling too sore tomorrow. And even if she was no longer set on gaining as much xp per day as she could, more was obviously better.

She considered it as she ate. Her captors made it far too easy for her to rationalize having sex until she could no longer stand. For instance, she was reasonably sure that lubrication+, whatever that entailed, would make being fucked in the ass more tolerable. And until the system deemed her piercings healed enough, she was going to keep doing anal. So getting it today would mean more pleasant tomorrow... which was the whole point. But it being a rationalization didn't change the facts. So long as she was stuck in a room, she couldn't escape. Which meant maximizing her xp gain until she was trusted enough to be allowed to leave her room. That was when she could start formulating an escape plan.

After she finished her dinner and while waiting for the tray to be taken away, she moved on to considering how she wanted to do this. The book had given her some ideas, it really was a shame that she was limited to anal only. When the tray was taken away, she closed her eyes and took a deep breath, then selected the task three times in quick succession.

When the men arrived, she was leaning against the desk wearing nothing but the heels. It was almost funny how less than a week ago she would have been beyond mortified in a situation like this. Now it was just the best way to accomplish what she needed.

The first man approached her from behind and pulled her into a hug, groping her chest with one hand. She leaned against his warm chest, almost enjoying it. He then bent her over, pulled out the lube and poured a generous amount of it all over her ass. Using one hand to keep her bent over, he groped and slapped her ass with the other, making her squirm and grit her teeth. His hand found its way between her ass cheeks, and he smeared the lube all over her asshole, then pushed his middle and ring fingers inside.

Taylor was doing her best to get whatever pleasure she could out of the situation by rubbing her breasts when he dropped his pants, grabbed her arms, and pinned her wrists behind her back. While she was attempting to protest, he lined up his cock and quickly pushed it inside, making her gasp. He only gave her a few moments to adjust before starting to fuck her ass. It was painful. It was uncomfortable. It was humiliating. And she was getting more aroused by the second as the other men laughed at her, waiting to take their turns.

Taylor closed her eyes and did her best to maintain what little remained of her composure as he used her ass while the others laughed at her humiliation. His thrusts steadily grew faster and harder until he pulled out and came on her hair. While she attempted to squirm, the second man grabbed her wrists and traded places with the first, taking her ass without warning. He was bigger than the first and she was already getting sore, but if he noticed her discomfort at all, her certainly didn't show it.

He came on her hair as well, and then the last man took his turn. He shoved Taylor onto the floor, and planted his boot between her shoulder blades when she attempted to protest. He crouched down on top of her and drilled her ass with his dick while grinding her chest against the rough carpet. Taylor felt tears in her eyes as she whimpered and squirmed. She was so close, but she couldn't possibly cum like this.

Then he proved her wrong. He pounded her ass for what felt like a long time, and when he came inside, her mind blanked. Her entire body went rigid, her sphincter clenched like vice around his cock, and she came.

Taylor barely noticed the status screen, or the men leaving. She had orgasmed. She had orgasmed from being fucked in the ass, in a particularly humiliating way, in front of an audience, and without other stimulus. What the fuck was wrong with her?

Despite how tempting it was to keep feeling sorry for herself, she had spent way too much time doing that, lately. So Taylor pushed herself to her feet, pulled off the heels, and went to take a hot shower. At least this way she wouldn't wake up tomorrow feeling too horny to think clearly.