It so happened that one day it was imperative that certain documents be brought to one of my clients in prison for his signature. This was nothing that I needed to do in person, but it had to be done by someone in person because the mail would take too long. Swamped with work, I turned to Lo and asked her if she would go in my stead as my secretary — a role she loves to play around the office.
To my surprise, rather than finding the prospect daunting, intimidating, or unwelcome, she jumped at the chance with excitement.
“Lo, this is not a fun little frolic. This is serious stuff. Jail is not as it looks in the Elvis video of ‘Jail House Rock.’”
“Fiddle-dee-dee,” she said in her mock imitation of Scarlett, “just show me the papers and where he has to sign and I’ll be back in a jiffy.”
I instructed her and began to send her off, but I had to stop her before she left the office.
She liked the “sir” part.
“You can’t go like that.”
“Like what?” she asked, innocently.
“With your hair in pig-tails and wearing those Daisy Duke cut-off shorts.”
“But Daddy,” she said with a pout, “don’t you like them?” She sauntered up to me and grabbed my crotch, licked her teeth and said, “Oh yes, you do like them, Daddy.” She then turned around, bent over and said, “Spank me.”
I gave her a good whack, to which she called out, “OUCH!” and rubbed her bum. What do my office neighbors think?
“Daddy!” she said, feigning anger. Then she bent over and said, “Do it again.”
“LO, get out!”
“Oh Daddy, I love it when you talk to me like that. Spank me again!”
I gave her another.
She again rubbed her bum, but this time she was expecting the swift punishment I gave her and so she didn’t scream. But she did start stroking her pussy over her shorts and she said, “Fuck me!”
“Lo, go home and change into something you can wear to jail. Remember, no low cut blouses. No midriff. No shorts. No skirts above the knee.”
“But Daddy, that’s three-fourths of my wardrobe.”
“Well, look in the one-fourth that’s left.”
She got to the door, turned around and blew me a fat kiss.
“And no lipstick!”
“A girl can’t read this sort of thing without her lipstick,” she said, quoting her favorite — Holly Golightly.
I got back to work and didn’t put much mind to the little errand I sent her on, until about two hours later when I got a phone call from Lo. She was on her way back from the prison and she said, “Yes, Daddy, I did as you told me. But you didn’t tell me that little Carmine was so cute.”
“Lo. . .?!”
“Oh, don’t worry Daddy.”
“What happened, Lo?” I was beginning to feel like Ricky Ricardo talking to Lucy, saying, “You got some splainin’ to do.”
She then told me this tale:
“I got to the jail, just as you said. The horrid man at the entrance was incredibly rude. He treated me like I was some floozy or trailer trash. I told him I was your secretary, but he didn’t stop looking down his nose at me. After the trip in that tin can of an elevator with that H.A.L.-like camera staring at me the whole time, I was finally escorted by a very nice, gun toting guard to the specially secluded visitation room. Then I saw your client Carmine. When he walked in, his eyes were turned down at first and he looked so sad, so incredibly sad. But when he looked up and saw me standing there, it was like a transformation occurred. He brightened up and he smiled that cute smile of his.”
“Of course he brightened up, Lo. He’s been in there for months without any females to see him, except his mother.”
“I know!” she said. “That’s exactly what I thought when I saw him. He has the most adorable round face — like a little boy — and he was so polite and sweet.”
“So you gave him the papers and he signed them and you came straight home, right? Tell me that’s all that happened.”
“Well. . .”
I braced myself. “Please tell me you changed out of those shorts. You had to have changed, or the guard wouldn’t have let you in.”
“Oh, don’t you worry, Daddy-O, I changed. I put on a perfectly sensible black skirt and a totally work appropriate white blouse.”
“Phew,” I siged on the other end of the phone.
“But when I saw him, I immediately got hot. As I explained to him about the papers and where to sign and what not, I found I was unconsciously unbuttoning my blouse.”
“And the hem of my skirt was sliding up past my knees.”
“Daddy, I really wasn’t aware of it at first, but then I saw that Carmine was looking at my chest. He was looking down my blouse and I realized that this man probably hasn’t had access to a computer or any magazines or anything.”
“Of course he hasn’t, Lo. This is jail, not a hotel with cable and Pay-Per-View.”
“Exactly, and so an incredible feeling of pity suddenly came over me.”
“Yes, pity. . . and a real rush of adrenaline as I realized I suddenly was all wet. I mean, who knows if they had cameras in there or when the guard would come back and the thrill of it all was. . . well, it was too much for me.”
“Arrrggghhh.” I crumpled up and dropped my head down to my desk in defeat.
“So, I unbuttoned my blouse a little more. This time, very consciously. I saw that it was a welcome sight to him. And, seeing how much he liked that, I moved my chair a little ways back and slowly slid my hand up my leg, under my skirt. ‘It must be so hard for you to be in here,’ I said to him through the phone. ‘You have no idea,’ he said back. ‘So hard.’
“I continued to move my hand up and under my skirt, pulling it up to my waist as my fingers ran their way over my wet cotton panties, back and forth. I moaned into the phone. I slid one finger under the panty and exposed just a little of my puss for him. But before long I had pulled the entire panty aside in order to finger myself deep and hard. I was moaning and I was worried that the guard would come back. But I wanted to finish. I couldn’t stop. I loved watching him watching me — how he stared at me with a hunger I had never seen before. Finally, nervous as hell, I came with a gushing wave of cum. It pooled at the bottom of the plastic chair I was in and I had to stand up and, just as I did, the guard walked by. I smiled at him as I straightened out my skirt and I made a motion with my hand to say, ‘Five more minutes.’ As I did so, I realized how wet my fingers were from being up and in me. I stood and looked at Carmine and I said, ‘I’m going to have to get going, but don’t worry, I’ll come back to visit again soon.’ I took the papers and turned and before I left the room, I flipped up my skirt so he’d get one last glimpse of my ass. When I got to the car, I was so wet I had to take off my panties and rub one out again, right there in the parking lot of the jail. I’m sorry, Daddy, but I couldn’t wait. Even now, as I’m driving, I’m soaking through my skirt. Can I call you in about five minutes?”
“Just once more, Daddy. Promise.”
About ten minutes later I got a phone call from Lo. She said she managed to make herself cum while driving. When I asked her what she was thinking of as she touched herself, she responded with a request: “Promise me, Daddy, that I can be the first person to suck Carmine off when he gets out of prison.”
[Excerpt from the story, “Doing Hard Time,” from the blog: mysexlifewithlola.com]