I was doing thirty days on a bogus DWUI charge at the local county jail. I was there about a week when they moved me back to the trustee section. No big deal washing dishes, laundry, mopping some floors and what ever else the guards needed. I'd been there before and they like me, so I get moved back to work. The guys had all been there a few years, but since the last time I was in they had hired a female officer. Deputy Snider stood not much over five foot and had bright red hair, lots of freckles, large breasts and a plump ass, not really fat but plump.
While in general population she treated us like the male guards did sort of stand offish and strict. But once you moved back to trustee she backed off and let us do pretty much what we wanted. Her husband was the state trooper that busted me, he liked to come in the jail and watch her work while he gave us flack. Then she moved to night shift and my time became much more enjoyable. The night shift only had one officer on at a time, she started having me come out to the commons area to sweep and mop the floor, or do the laundry after everyone else had been locked down for the night. I didn't mind much since I was sleeping most the day anyway, besides it was nice talking with a lady any lady. The only female we get near besides the cook and the cook was in her sixties.
The first couple nights I noticed Deputy Snider watching me as I did my job, her eyes followed me around the jail. On the third day I was in the backroom doing laundry when she came in jumped up on the dryer and started talking to me, her shirt appeared to be unbuttoned farther than normal. But cop shirts are different they only look like they button, there's a button at the top and a zipper running down to another button at the bottom. Usually she wore hers buttoned up regulation style, her breasts were very large for her size and always looked like the were trying to bust out of her shirt, but tonight it was unzipped down past the crest of her large breasts. The zipper still strained with the pressure her tits were still putting on the shirt, as the dryer shook and she talked, her the zipper slipped lower exposing more of her breast and the bra that appeared to small to contain their cargo. The phone rang and she jumped up leaving the room, zipping her shirt as she went out the door.
Fifteen minutes later she came back and hopped back on the dryer, something about her was different as she sat there talking and bouncing she seemed to be bouncing more. That was it, while she was gone she had removed her bra. The fabric of her shirt seemed even more strained than before with nothing keeping her mountains of flesh restrained, the zipper was making the same migration as before each time I turned away from her it lowered an inch or so. It had worked its way past the top of her breast and was headed down the front of them when I turned to put the last load away. I turned as she yawned and stretched like a cat, arms up, back arched and her shirt exploded away from the largest set of tits I have ever seen.