She had been a bitch at school – but doing so had let her achieve exceptional academic performance, and now at a young age she was set to make partner at the most prestigious law firm in the nation.
The only problem was that to do so, she needed the approval of the existing partners – and one was Geoffrey Rich, the father of Tim Rich, the boy she had been cruellest to of all. She still remembered turning down Tim’s invitation to the prom and publicly laughing at him, and the devastated, humiliated look on his face.
She knew that Geoffrey didn’t like her. So she decided to tackle the issue head on.
“I’m sorry about what I did to Tim in school,” she said to Geoffrey at a lunch meeting in his office. “What do I need to do to fix this? How do I get your approval?”
Geoffrey looked her up and down, lingering uncomfortably on her breasts. “You’ve got a good legal mind, Tiffany,” he told her. “But you’re also a difficult bitch. I need to know that you can be a team player.”
“I can be a team player,” Tiffany said eagerly.
“You know all the other partners are men,” said Geoffrey. “You can wear suits around the office, to keep the respects of the juniors, but I’m going to expect that when you attend partners-only meetings, you dress in a way that demonstrates you know that women are for men to look at.”
Tiffany blushed. It was a humiliating demand, but she’d known that making her way in a male-dominated profession meant occasionally playing by men’s rules.
“I can do that,” she said. “Show some cleavage, short skirts – is that what you mean?”
“That’s a start,” he said. “Go a bit further. Make sure that no one who saw you would ever mistake you for a lawyer rather than a whore.”
Tiffany blushed deeper, but she agreed. She had some outfits that she’d only worn with her occasional sex partners for roleplay…
“We’ll want you to sign a document waiving your right to bring any sexual harassment or discrimination proceedings,” Geoffrey continued. “The partners are going to call you ‘sugartits’ or ‘bitch’, and we don’t want to worry about consequences for that.”
“As long as it also protects my position as a partner,” said Tiffany. “Agreed.”
“And lastly, my son would never forgive me if I let you make partner without getting even for what you did to him – and his classmates – in school,” said Geoffrey. “Your school reunion is coming up in two weeks, isn’t it?”
Tiffany agreed that it was, not liking where this was heading.
Geoffrey showed her a picture of an outfit. It was a tiny piece of red cloth, half lingerie, half sling bikini. Two straps ran from behind the model’s neck, down over each breast – covering only the nipple, and nothing else – to meet in a wide strip of cloth over the model’s pussy.
“You’ll be wearing this to the reunion,” he told her.
Tiffany paled a little. “How does it stay in place over her breasts like that? Why doesn’t it slide into her cleavage?”
“Her aroused nipples hold it in place,” said Geoffrey. “As long as your nipples are nice and perky, the elastic on the edges will keep it from coming loose. You have to walk carefully, of course, but you can manage that. If you stop being aroused though, yes, it will expose your tits.”
Tiffany blushed and said, “And that’s it? I just have to wear that?”
“Oh no,” said Geoffrey. “And you also have to go up to every man in attendance at that event, and apologise to him for being a bitch, and tell him you’re more agreeable now, and that he’s welcome to play with any part of your body he can see, as long as he doesn’t disturb your clothing or use force on you.”
“So men just get to grope me? And fuck me?” she said, outraged.
“Grope you, yes,” said Geoffrey. “You’re not allowed to protect yourself, or stiffen up, or resist, or move away if a man wants to touch parts of you he can see. But you don’t have to rearrange your body, either, so you shouldn’t get fucked. After all, the dress covers your pussy and anus, and given that you don’t have to lower your head it should be pretty hard for them to get their cock into your mouth.”
She blushed. “And if I do all that, I make partner?”
“Stay until the last other male guest leaves, and if you do all that, you make partner,” Geoffrey agreed. “Agree to do this, and then back out, though, and it’s never going to happen. Oh, and one last thing. I need to see self-control from you. Keep those nipples covered. If you can’t stay aroused enough to keep the fabric in place, you’ll still make partner, but I’ll keep sending you to corporate functions in this getup until you learn to do it right.”
Tiffany swallowed nervously, but didn’t back down. “I can do that,” she said. “It’s a deal.” She could dress and act like a slut for the sake of professional success, she decided.
On the day of the reunion, Tiffany’s dress arrived by courier. It was as skimpy and inappropriate as the picture had suggested. It came with a pair of high heels, with a card attached read “required”, another card reading “no underwear!!!”, and a small box which turned out to contain a vibrating butt plug and a single white pill labelled “aphrodisiac”. A card with these read, “Not required, but might help to keep your nipples hard.”
She dithered about the pill and the plug. She didn’t know what exactly the pill was, and was concerned about her judgement if she took it. And the plug was intensely slutty, and would be visible pressing against the fabric at the back of her dress if she used it. But she was already going to look like a slut, and better to do it once and get it right than have to repeat it again in future. She undressed, swallowed the pill, inserted the plug into her butt, and activated the vibration, moaned involuntarily as it began to stimulate her anus, and then rubbed her pussy until she felt her cunt wettening and her nipples stiffening. Then she dressed in the slutty outfit, put on the high heels, did her makeup, and headed out to the reunion.
She almost backed out when she got to the hotel the reunion was taking place in. Everyone from school was going to see her not as the professional success she was, but as a degraded whore. Surely she couldn’t – but she could, and that success was more important than what the losers she’d gone to school with thought of her. She got out of her car, and went in, walking carefully on the very high heels.
The doorman of the hotel leered at her. “My reunion didn’t have hookers,” he said. “Some kids get all the luck.” She ignored him, blushing.
Inside, her face turned even brighter red. There were hoots and cheers at her outfit. “Is that Tiffany?” she heard someone whisper. “What a whore!”
Trying to pretend this was all a horrible dream, that it wasn’t real, she began her circuit of the room, finding each boy she’d gone to school with – now a man – and apologising for being a bitch and telling him he could play with what he could see.
Some of the men were nice, and treated her respectfully. Some, after asking several times if she was serious, would stroke her hair or her cheek, before cautiously touching the sides of her tits and, when she didn’t object, squeezing or slapping them. One guy kissed her on the lips, pushing his tongue into her mouth, and when others saw that she didn’t object to that either, everyone wanted a turn.
She had never felt more humiliated and objectified – but the pill and the plug were doing her work, and she was aroused. Some of the boys, she would return the kiss, instead of passively let it happen. At first she was kissing only the more attractive boys, but each time she did, she would get wetter, and soon she was passionately returning every kiss, pressing her tits against the men’s bodies and moaning into their mouths.
Some of the women present left early in disgust as more and more of the event began to focus on playing with Tiffany. Of those that remained, most were taking an active interest. Pretty Sally Goodwin, who Tiffany would never have suspected of being bisexual, came up to her and said, “Do I get to play, too?”
Geoffrey had only told Tiffany she had to play with men – but men were surrounding her, men who she had just apologised to for being a bitch, and she felt nervous about how they would react if she turned someone down here in public. So she said, “Yes, you can play,” and soon she was kissing Sally, too, as Sally ran her hands over the sides of Tiffany’s tits and scratched her nails down Tiffany’s back.
As the night went on, the men got drunker. Staggering away from a passionate session of kissing with Bryan Hendler, who had been a nerd in high school but was actually quite good looking now, Tiffany didn’t look where she was going, and didn’t realise that class clown Roy Harris had climbed up onto a refreshments table, knelt, and exposed his cock. She ran right into his groin, and when she gasped in surprise, Roy pushed his cock into her mouth.
There was an immediate cheer at this from the other men, and shouts of “Roy! Roy!” Tiffany’s gorge rose, and she wanted to pull away – but he had used a part of her he could see fair and square, and she wasn’t allowed to retreat or resist. She didn’t have to cooperate, though, either, so she just stood there with the cock in her mouth, looking up at him with eyes that expressed her displeasure.
Realising that she wasn’t going to suck, Roy began to fuck his cock in and out of her mouth. Tiffany felt a hand on the back of her head, holding her in place – not using force exactly, just blocking her ability to move backwards. She realised it was Sally Goodwin when she felt Sally begin to kiss her neck as Roy face-fucked her. When Sally’s other hand moved to gently press on the base of her butt plug, Tiffany couldn’t help herself – she moaned whorishly, and began to actively suck.
Roy orgasmed swiftly, and Tiffany convulsively swallowed his cum, not wanting it to dribble down her chin. She tried to step away, but Sally was still behind her, and then another man got up on the bench – Geoffrey’s son, Tim. Tiffany realised there were more men lining up behind Tim, and she now tried to struggle and get away. She hadn’t agreed to be a blowjob whore for her whole class.
But Tim saw what she was going. “She’s not allowed to pull away,” he said to Sally. “She doesn’t have to cooperate, but she can’t resist. You can hold her if she tries to.” And, accordingly, Sally’s hand on Tiffany’s head tightened into a firm grip on her hair, and her hand on the plug became a grip on the back of Tiffany’s dress. Tim pushed his cock at Tiffany’s mouth until she opened up, and then began to face-rape her.
Something else was happening as Tiffany sucked Tim’s cock. Sally’s grip on her dress was ever so slightly tugging on the fabric covering Tiffany’s groin, and to her horror, she felt it begin to bunch up, and then slide between her labia to give her camel toe. Her pussy lips were now completely exposed, and it wasn’t long before one of the men noticed, and moved over to begin playing with them, stroking and tugging and pinching at them.
Tiffany was losing her sense of self now. Everything was sensation – the hand gripping her hair, the cock in her mouth, her wet throbbing pussy, the vibrations in her bowels, the teasing of her cunt lips. If she didn’t escape now, she knew she would lose herself completely.
Tim ejaculated in her mouth, then another man stepped up to feed her a new cock. She moaned and tried to twist her head, but Sally had a firm grip on her. She struggled with her whole body, trying to pull away, trying to run.
Unfortunately, Sally had a very firm grip on her dress. As Tiffany pulled forward, the fabric stretched – and then ripped, right at her crotch. The whole dress fell away, revealing her nipples, her ass, and of course her wet, throbbing cunt. She staggered a few steps, and ran into a nearby table, falling over it bent at the waist.
Immediately, Sally was on her, holding her down. There were cheers and catcalls, and before she knew what was happening she felt the first cock push into her fuckhole from behind, as another man moved round to plug her mouth with his dick.
“Your dad’s the best, Tim,” she heard the man with his cock in her mouth say.
“I know, right?” came Tim’s voice. “And the deal she made says she has to stay till the last man leaves. I’m going to go and rent this room for the next fortnight. It’ll be expensive, but I think it’s worth it. As long as at least one of is here at all times, she’ll be obliged to stay.”
There were more cheers. She heard the shutter-sound of photographs being taken.
“And hey, by the time two weeks are up, her birth control should be well and truly out of her system,” continued Tim. “Who wants to knock this bitch up?”
There were even louder cheers. The man in front of Tiffany pulled out of her mouth and ejaculated on her face. Sally moved round and began to kiss Tiffany, spending half her time probing Tiffany’s mouth with her tongue and the other half licking the sperm from Tiffany’s face. When she was done, she stood up, and Tiffany realised that she was looking at Sally’s bare pussy.
“Lick, bitch,” said Sally, her hand still gripping Tiffany’s hair, and Tiffany defeated, did as she was told. She supposed that by two weeks from now, she was going to be *very* good at doing as she was told…
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One thought on “Story: Tiffany’s Reunion”
Why do you think it’s called “naked ambition”?