Playing To Lose is one of 20 stories featured in my e-book “Fit For Purpose – Stories of Sports and Exercise Erotica”, available through my creator site at AllTheseRoadworks.com. (Click here to check it out!)
His argument was simple – in a battle between a woman’s desire to succeed in life, and her innate nature as a slut, the slut would win every time.
She argued with him, so he challenged her to a bet, in front of all their friends. She had played tennis at a national level in school, so they would have five tennis matches. Before each match he would name a degrading sexual forfeit and if she lost she would have to pay up. If she won even one of the matches, he would withdraw his argument, apologise, and pay her $10,000 in winnings.
The catch was this – she would be hypnotised with a simple suggestion: if at any level she *wanted* to pay the forfeit he named, she would deliberately play so as to lose the match. She blushingly, stubbornly agreed.
First round. “If you lose, you’ll play with your tits out and no panties for the rest of the games.” She lost. She avoided eye contact with her crowd of watching friends as she slid off her panties and exposed her breasts, blushing bright red all the time.
Second round. “Lose this and you agree to marry me, suck my cock in public at the wedding, and wear the exceptionally slutty wedding dress I’ve bought you for the remaining games.” She lost again. The gathered crowd laughed at the implication she must have wanted it.
Third round. “Lose, and you masturbate between points, and to the edge of orgasm after each match.” She lost. She tried to turn away from the crowd as she stuffed her fingers in her fuckhole but they moved to get a better view.
Fourth round. “Lose, and you get a boob job to take you up to at least an F-cup.” She lost.
Fifth and final round. “Lose, and we legally change your name to Fuckpuppet, you become my slave for life and you live naked in a kennel in my basement.” Her face went crimson, and she felt like she was trying her hardest, but still she lost.
As he helped her strip naked after the match and put a dog collar and leash on her, he wondered if the hypnotism had been effective. He really was a very good tennis player, and of course he had put a fairly strong sedative in her refreshment water, so she never really had a chance of winning. But he liked the thought, as he stuffed her tennis racket handle into her pussy again and again to bring her to a squirting orgasm in front of all her friends, that she would forever think that all this had happened because deep down she was slutty enough to *want* it…