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This story begins in medias res – that is, without much of a prologue and without its proper context For a personal introduction, suffice it to say that I'm a grad student at a well-respected midwestern university. Kurt had had me on a line all afternoon, texting me about his "South City Whore" and their coming tryst. He is my sex mentor, you might say. A brutal, muscular man in his mid-forties. He might be ex-military, I'm not sure, but from things he's said I gather that he works at a prison. He's a professional disciplinarian, and he has an unmatchable sex drive and little empathy or regard for feeling. I found him on Craigslist; he was looking for a bisexual wingman, someone to tag team "whores" and "sluts," and to suck his cock along with those whores. I responded with an email and a photo, he came back with his phone number, and we texted for a while. He made me photograph my body from every angle, including my spread asshole, and send him the photos. At the time, I had let my pubic hair grow untrimmed for a while, and he derided me for it. He told me to shave myself bare and then send him another picture. I felt a hot brick settle low in my stomach and my cock push against my jeans when I read that text. I knew then that I was his bitch. In the shower that night, I took my razor and slowly, carefully shaved my cock and balls and then shaved upward toward my stomach. My hair, facial and body, grows sparsely anyway, so it wasn't an onerous chore. I was hard the whole time, and leaking precum. I sent him the photo, snapped on my phone in the foggy bathroom mirror. He sent his approval and I texted back, "Thank you, sir." Read more »