Dear Male Chastity Lifestyle,
My very female, very hot boss was always the controlling type—I guess that’s how she became the boss. Obviously I can’t reveal any of the details of what I do or where I work, but I can give you the important parts. Trust me, what I’ve experienced has been totally strange, fascinating, and exquisitely pleasurable.
My boss and I, I’ll call her Jill, had two types of interactions since the day I started working at my current job. The first was her yelling at me—she yells at everyone in the office, including the cute administrative assistant who brings everyone coffee. She rarely apologizes, and people sort of know what she’s like and simply tolerate it (I’m in a relatively well paying profession).
The second kind of interaction we’d have was this strange, on-and-off kind of flirting. She’d say something vaguely sexual to me or occasionally brush her hand across mine. Once, when we were looking at a report together on my laptop, she put her hand on top of mine to move the mouse. I immediately felt a spark. As I would soon find out, so did she.
The first overtly sexual thing my boss did was again, one evening after hours when we were working late on the computer again. She walked around my desk and leaned over to point at the screen. She was so close that I could smell her perfume, and I got a clear look down her rather ample cleavage. Much to my surprise, she said “here, let me do it,” and sat on my lap to take over. I was stunned. I’m no Lothario with women, but this was about as clear of a signal as a guy can get, so I went for it. You can guess how the rest of that night turned out.
Over the next few weeks, our trysts would continue, and become more frequent. Sex with my boss was a mind blowing experience—she was unlike any other woman I had ever been with. She clearly loved being in control, and her favorite position was on top of me. Once, she even slapped me. It might sound strange, but I liked this a lot more than I ever would have expected.
Slowly, my boss changed my sexual appetites. I craved her telling me what to do, slapping me, scratching me, and basically having her way with me. When she left on a business trip for a week, we had phone sex almost every night, and during the daytime I would receive texts from her giving me instructions—“don’t you dare come until I tell you,” or “your cock belongs to me.”
These days, I’m learning about the endless pleasures of things I only tangentially knew existed, either through pornography or “weird stories” from friends. My boss ties me up regularly, makes me report to her whenever I have an erection (if it’s at an inopportune time, I’ll be punished), and—most recently—made my nipples delightfully sore from a pair of nipple clamps.
I love my job.
Keep up the good work,