Jane’s intention was good, but she chose the wrong words.
It had started when she applied for the position as head of HR. She knew she had made a mistake in how she dressed as soon as she saw the only other applicant – her teammate Lara. Poor Lara, terminally flat chested, had dressed in sensible chaste librarian clothes and flat shoes. By contrast Jane, brought up by her mother to dress “like a real woman”, was in makeup, high heels, short (but professional) skirt, and a neckline that reminded everyone just how big her tits were without being slutty about it.
A male co-worker had snapped a photo of them, standing side by side, the sexless church mouse and the big-boobed secretary, and of course once she actually got the job, the rumours started that she had fucked her way to success.
She had done no such thing. The interview had been all business. And she resented that people assumed she was a slut just because she had a large bust and dressed attractively. She said so loudly, and often, and – to her eternal regret – she said it particularly forcefully at after-work drinks to a group of her male co-workers.
“I am NOT a slut,” she said, two glasses of wine into the night, leaning forward for emphasis without realising she was showing off her cleavage.
“Sure you are,” said Caleb from Marketing. “I bet you’ve fucked for every job you’ve ever had. With tits like that, I bet you can’t say no to any man. I bet those fuckbags make you so horny you can’t control yourself. I bet your pussy’s loose as a thin man’s belt with all the times you’ve been fucked.”
“How dare you,” she said, wondering how drunk she was. “How dare you.” And then she went on to say the words she would later wish she had avoided. “My pussy is incredibly tight, and I can absolutely say no to any man no matter how horny I am.”
Caleb leaned forward, evilly. “Want to bet?” he said. “You win, and we make everyone at work shut up about it. We win, and we add ‘office fucktoy’ to your list of official duties.”
“Absolutely,” she said, not really thinking Caleb was serious. “It’s a bet.”
Caleb grinned, and explained how the bet worked. Alarm slowly dawned on her face, and she rose to get up and leave, to escape this situation, but she felt the hands of Jack from IT on her shoulders, pressing her back down. “You made a bet,” he whispered in her ear. “Are you forfeiting?”
She whimpered.
They made her finish her next glass of wine, and then took her to the alley behind the bar. It was dark and dirty. There, they made her disrobe. She was nervous. Men came in and out of the alley on their way to the toilet block in the next building. Someone would see her. Caleb told her that was the point. Soon she was nude but for her high heels.
Caleb gave her a small pink dildo, and told her to put it in her cunt. Biting her lip in shame, she did so. Her pussy was dry, and she had to work it into her fuckhole slowly.
“Now put your hands on your ass cheeks and spread them,” he told her. She obeyed, blushing as her workmates stared at her anus and dildo-stuffed pussy. It was hard to keep the dildo inside her in this position – her pussy wanted to squeeze it out.
“Now you’re going to show us that your pussy is tight, and you can say no to men even if you’re horny,” Caleb said. “All you have to do is walk from this end of the alley to the other end, without taking your hands off your ass or letting your thighs touch each other. If the dildo falls out, though, you have to pick it up, masturbate with it for three minutes, and then return to this end and start over. You keep trying until you succeed, or until you beg a man to fuck you.”
Blushing, Jane began to waddle awkwardly down the alley, ass spread, legs apart, squeezing the dildo with all the cunt strength she could. She was about halfway down when the door to the bar opened and a man emerged. Jane squeaked with shame, and as she did, the dildo dropped from her pussy onto the alley floor.
Red with humiliation, Jane looked around for help. Caleb was standing at one end of the alley, Jack at the other. There was no escape. The man from the bar was staring at her in surprise and lust. Slowly Jane bent to retrieve the dildo, slid it into her pussy, and began masturbating. The man watched as she fucked her sluthole with the toy. She wanted to die of shame.
Caleb whistled, indicating three minutes was up. She walked back to him, pushed the dildo into her cunt, and tried again.
Unfortunately, her cunt now had the beginnings of lubrication. She didn’t even make it ten steps before the dildo slid out. Tears of frustration and embarrassment on her face, she picked it up and masturbated again. Another man had emerged from the bar. Both him and the first man were staring at her. The first man was filming her on his phone.
At the end of three minutes she was dripping wet, and she didn’t even have a chance. The dildo fell out on the second step. The next time, it fell out on the third. Soon she was doing little but masturbating in an alley with a dildo.
On the fifth try she felt an orgasm coming. She began to fuck her pussy even faster, but suddenly Caleb was there, pulling her hand away. “No making yourself orgasm,” he told her. “Ten-minute cooldown.” She wanted to scream in frustration. She was so horny, and so humiliated out here. She wanted to cum, so it could be over. She hurried back to her start position and re-inserted the dildo.
Three cooldowns later, she had been at it for an hour, and all she could think about was her need to cum. A small crowd was gathered, laughing at her and filming her humiliation. She pushed the dildo into her pussy, grabbed her ass, and tried to run towards the crowd, but the dildo fell out immediately. She grabbed it and immediately started to violently fuck herself with it, hoping to cum before Caleb could stop her – but he was too quick, and she found herself restrained.
She broke. She looked at the first man in the crowd. “I’m sorry,” she whispered, in a hoarse voice. “I’m sorry, I’m such a slut, please, fuck me. Please fuck me.”
Caleb whispered in her ear, “Tell them you fucked your way to your job.”
“I did,” she said. “I’m just a pair of tits. No one would give me any job unless I fucked them. Please fuck me now.”
The man who was filming her looked at her, and said, “Well, I would fuck you.. but that would be awfully unfair on the rest of your audience. I think I could only fuck you if you agreed to let every other man here have a turn with you as well…”
She froze, in terror. Let this whole crowd gang rape her? She couldn’t. It was bad enough she was propositioning one man… and losing the bet, too, so the whole office would get a turn with her… but there were at least 20 men here now. Surely she couldn’t…
Caleb reached out and lightly stroked her left nipple. Her whole body shook, vibrating with need. She suddenly stopped picturing what it might feel like to be used by this crowd, and started picturing how she would feel if she didn’t fuck them. This lust – this unbearable lust – would go on forever. She had to satisfy her pussy. She had to.
“Yes,” she sighed. “All of you. All of you can use me…” And like the good fucktoy that she was going to have to learn to be, she got down on all fours, faced away from the man, lifted her ass in the air, and waited for him to take her…
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