Jail uniform Stories

“Are you hanging in there,” Kim asked me, sitting on a chair outside my cell as she paid me a visit. Still playing along with the game, but knowing what was coming. “I’m doing fine,” I replied. She looked around. “I brought you something,” she said. She reached behind her and from tucked inside the back of her skirt, she pulled out a vibrator. She handed it to me through the bars. “This is what you asked for in your lette...

Before Jeff and I had started this adventure, we both knew, even if we hadn’t said it out loud, that sooner or later, there would almost certainly be some breaking of character. At day and at night, for the majority of the time, we could fantasize and pretend all we wanted that I was really in jail, and I might even be able to convince myself of it in my own mind. But sooner or later, when we had sex, we were going to be...

“Thank you, Officer Cooper,” I said as Jeff passed me my morning breakfast tray through the bars, a tray with a plate of eggs, orange juice, a piece of toast, and a bowl of oatmeal. He nodded and I sat down on my cot and ate with the plastic utensils which I was provided with. Jeff really had worked out as much as he could to make this as realistic as possible for me. For us. As he started to walk away, I nervously called...

I woke up on my third day/second morning in my cell to Jeff loudly clanging a nightstick against the bars of the cell. He was still (or, at least, again) dressed in his police uniform. “On your feet, Inmate,” he called sternly. With a slight flutter in my stomach and suppressing a smile from my lips as I was still growing used to the little game we were playing, I stood up. But he saw that slight smile. “Something funny,...

The village looked pretty vacant as Jeff drove up what was, or at least what seemed to have used to have been, the main road. He hadn’t told me where we were going, only that he had a surprise for me. “The county took over this small village police department about six years ago or so,” he remarked as we drove. “Then about a year and a half ago, this village department ceased operating altogether and everything was moved...