While traveling around the country about a year ago, I found myself in a bit of trouble in a small town in Arizona.
I got into a bar fight, and was given 30 days in the county jail for disturbing the peace.
As it happened, I was the only prisoner in the jail that night, and I was pretty surprised when the night guard came to my cell a little after midnight. The guard was a female of about 40, with short dark hair and a ripe figure. She told me her name was Sally, and that she was going to search me for contraband.
I told her that I had just gotten there, and that they had searched me before putting me in the cell. She told me to shut up, and ordered me out of my bunk. She then took out her handcuffs and secured my hands to the bars of the cell. Then she started to pat me down.
I took this for normal procedure, until she reached down the front of my pants and grabbed my dick. She leaned in next to my ear and said that I’d better do as I was told if I knew what was good for me. She then turned me around, my hands still cuffed above my head to the bars.
Then Officer Sally stepped back and started removing her uniform! When she was down to her bra and panties, she stepped up again and unfastened my pants, letting them fall to the floor, then yanked my boxers down past my knees. She then picked up her nightstick, lay down on my bunk and slid the nightstick under the waistband of her panties and down between her legs. With her other hand she pulled her bra up over her tits and started pulling on her nipples. As I watched this I found my dick getting harder and harder.
After several minutes Sally pulled the nightstick out of her panties and brought it over to me, telling me to lick it clean as she held it against my lips. Her scent filed my nostrils as I did as she said. Once it was clean she released the cuffs and told me to lie on the bunk, securing my wrists to the top of the frame. She then removed her panties and got on top of me, lowering herself onto my dick.
Once she had all of me inside her, she took hold of both my nipples and tugged and twisted them until I cried out. She then reached for her discarded panties and shoved them into my mouth, after which she grabbed my nipples again. At that point she looked me right in the eye and told me I’d better not come till she was ready, and if I came too early she would punish me.
She then started riding up and down on my dick. It had been several weeks since I’d been laid, and I have to say it felt great. As her pace got faster and faster, I felt I would not last long, and was a bit concerned as to what she would do if I came too soon. But when I felt her fingers grasp my nipples again, the threat lessened my need to come.
She rode me for a good 15 minutes, tweaking my nipples from time to time. But at last it was too much for me, and before I knew it I exploded inside her, filling her with come. “You bastard!” she yelled, slapping my face. “I wasn’t ready!” She then pulled the panties out of my mouth, and before I could say anything she was sitting on my face, telling me to clean up my mess, and that I’d better get hard again as I did it.
I had never gone down on a woman after fucking her before, but I opened my mouth and slipped my tongue into her come-filled pussy, tasting my own jism. She started to stroke my dick, telling me to be sure and lick it all out of her pussy. I was a bit surprised at how much come there was, and more surprised when I felt my dick start to harden again.
When Sally was satisfied that I had done a good job, she mounted my revived cock once more. She came quickly that time, then continued riding me up and down until she climaxed again.
When she regained her breath, she got off me and undid the cuffs, then quickly got dressed and left the cell.
The next night, around the same time, Officer Sally entered my cell again and ordered me to get undressed. When I was naked she tossed the cuffs to me, saying, “You know what to do.” I lay down and fasten my hands to the bunk as she removed her uniform. She then came over and sat on my face, stroking my dick until it was hard. As before, she mounted me and started riding me, telling me not too come till she was ready.
But the fact was that I had been thinking of her during the day, and was already in a state of excitement, so I came in just minutes. “Oh, you are going to pay for that!” Sally yelled, and once more made me lick my come from her pussy. When she was clean she got dressed and left, telling me, “You are in for it now!”
The next night, when Sally came to work, I heard her and another guard talking in another room. Then after a while I heard Sally shouting, “That’s it! Fuck me hard! Yes, oh yes, Christ, fill my pussy with your come!”
After the other guard left, Sally did not even bother to get dressed. She came naked into my cell and tossed me the cuffs, telling me to put them on as before but not to bother undressing. “You’re gonna be licking other men’s come from my pussy until you show me you can control yourself,” she told me.
She then sat on my face, and when I did not start licking right away, she grabbed my balls and told me to do what she said. Not wanting to lose my nuts, I did it.
Once she was clean she removed the cuffs and told me to jack off while she watched. I did that too, and when I came she made me lick the come from my hand.
The next two nights were the same. She would fuck the guard she was relieving, then have me lick her clean and jerk myself off. On the third night, she fucked the guard as before, but when she came to my cell she asked me if I thought I could last long enough this time to get her off. I said yes.
That night she didn’t bother with the cuffs. She quickly mounted me, her come-filled pussy slipping up and down on my dick. I managed to hold out longer this time as she rode me hard, moaning and telling me how good it felt. Then she came, and after a few minutes she came again, with me exploding inside her.
Afterwards Sally sat on my face as usual, this time giving me two loads to lick out of her pussy. But to my surprise, she also took my limp dick between her lips and sucked me till I was hard again. We fucked three times that night, and every night after that until I was released.