Ms. J was not my type. I don’t think that she was anyone’s type or that anyone was her type. By the way she dressed, I would have guessed she was a lesbian—and not the lipstick kind. My life and spank bank were full of taller, blonder, nicer women. How did I end up where I am with her and why do I stay here? Ms. J is not her name. She lives in apartment J, which is right above mine. It’s a classic three-story walkup: gard...

Ms. J used me for things that were private and personal but not intimate. You don’t consider the feelings of a buttplug. You lube it up, use it, clean it, and toss it back in the drawer. Does a buttplug enjoy its work? The lobby and stairs were empty at 8 AM, so I texted her and quietly slipped in her door on the dot. The coffee seemed to meet her expectations. As she sipped it, she told me some of her story. “I’m a write...

After the craziness of the first few days, things settled into a routine. Foolishly, I got careless. The pain of the punishment Ms. J prescribed was mild compared to how bad I felt for failing her. I was determined to put in extra effort to try to solve the problems I had created for her and to regain her trust. The unusual events of the first few days were explainable. The first night was to test my obedience. The second...

The day after she allowed me an orgasm, Ms. J had me wear the butt plug to the library. As previously, she said it was to keep me from getting the wrong idea of our relationship. “Hormones are powerful,” she said. “They make you do stupid things.” She was referring to my horny carelessness that ended up with her having a broken leg and my being in her service. Objectively, there was no way anyone would know I had it in me...

It was not yet 10 AM when Ms. J ordered me out of her bed. “Get going. You still have to make up for missing yesterday.” I felt her eyes on me as I got dressed, but did not dare meet them. She was naked, still damp from her orgasm as were my lips and cheeks. Stopping by my apartment to get cleaned up, I was sorry to have to wash Ms. J off my face. I knew she would expect me to wear the buttplug today so I inserted it. Onl...