That night, I let Tanner fuck my ass. There was no point in protecting it anymore. My blackmailer had used it once and I assumed he'd use it again. It had been more enjoyable than I'd thought possible, and even if Tanner was larger, I believed if he was gentle, it wouldn't be terrible.

As he made love to me that evening, after I'd had my first orgasm, I asked him if he would like to put his cock in my ass. He stopped in surprise.

"I'd love to," Tanner replied. "But it should be properly prepared for anal sex by stretching it out. I can get some plugs if...