Holly's Dilemma

[Johnny Lawrence]

An uptight 28 year old contemplates the legends she has heard about the sheriff's department's treatment of women convicts, and considers her options.

--


With her car sitting inconspicuously in the motel parking lot, she could see the Sheriff's van plain as day. "Van" might be understating it though, it was closer to the size of a small school bus. The side doors opened and a deputy got out. He was a tall fellow, rather portly, with a gut that hung far over his belt and the kind of mirrored sunglasses the movie cops wore.

Holly picked at her taco salad, pretending to eat. The plastic fork dangled from her fingers, and she idly poked it into the lettuce and ground beef, digging at it without glancing down or bringing any bites up to her mouth. The food wasn't bad, in fact she quite liked the place that made it. She had eaten a number of their salads before, which was an excellent reason for her to go there today. It was definitely why she had come here, and ordered the salad, and decided to park in this particular spot, facing her car the direction that she did. And she was eating early today, at (sparing just a fraction of a second to glance at the clock on her dash) 11:15 am, because... because she was hungry.

She had taken off work on a Thursday because there wasn't really anything she had to get done, and she had months of vacation time accrued, and she might as well take it right? Just take a personal day at home, eat at the taco salad place, and maybe go for a run and then watch some daytime TV. Sounded good.


The women started to get off the transport van. One by one, they came down the steps, hobbling along slowly in the chains that connected their wrists and ankles. The fork fell from Holly's fingers and she stared at them. Criminals from the jail, a real life chain gang, required to perform community service as part of their sentences. Her car was less than a hundred feet away, right across the street. She had a great view as each of the women was brought out of the van, and made to stand beside the vehicle in a line.

It had been in the news, of course. The new 'tough on crime' programs the Sheriff had implemented. More cops, more enforcement, lower tolerance. But all that meant bigger budgets, which the city hadn't approved. They told him "find some revenue first." And so he did. The crime rate hadn't gone down yet, but the Sheriff sure was raking in the revenue. There was an outcry, as there always is with these things. But then when the four women on the city council were arrested for various reasons and drafted into his program, they'd been forced to recuse from all votes involving it, even after their "conditional releases."

When the last woman climbed down out of the van, Holly counted ten of them. She wondered what they had done. Or had been accused of doing. Ten women, all relatively young. All attractive. All in their twenties and thirties. They didn't look like criminals, more like professionals and businesswomen. They looked like, well, like...

Holly shifted in her seat. It was hard to get comfortable. She kept fidgeting.

Picking up trash on the side of the road was one thing. That was what chain gangs were expected to do. But after a year of the tough on crime program, the streets were clean. And people liked clean streets. Holly herself had driven by and laughed, seeing a line of women who probably thought they were too good for that sort of thing. Some bitchy Karen toiling away in 95 degree heat, sweating like a hog in a white crop top and orange booty shorts, carrying a half-full garbage bag. And when it happened to somebody you *knew*, well that was the best. Jamie at work had been pulled over for littering. She spent a *month* out there, and people had taken videos and shared them with the rest of the office (well, *Holly* had been the one to take the videos, to be honest -- Jamie had been a real bitch when they first started and Holly didn't like her).

Technically it was considered a pre-trial diversion program. Holly hadn't known what that was until reading up about it. They would dismiss your charge after you completed your community service, so there was no trial. You could fight it, of course, but now the courts were backed up, after some of the female judges were arrested and put into the program. Somebody said it would take over a year to get to trial on a simple misdemeanor offense, maybe a year and a half. So do you sit in jail and wait, or volunteer for community service?

But the women Holly was watching now weren't carrying trash bags. The streets were spotless. The hotel parking lot where Holly sat was directly across the street from a gentleman's club, and now the fat deputy was ushering the line of women inside. The Sheriff had found some other way for inmates to serve the community. And finally, he found his source of revenue. Raising money for the Sheriff's department is helping the community, right? "It will help me hire more officers to go after the real bad guys," he said. The three men on the city council had clapped.


The inmates would go onstage and dance, and their tips would go to the Sheriff's office. At least the ones with rhythm and coordination anyway. And if the customers wanted a closer look, or more personal service, the girls could be made available for that too. For those who couldn't dance, they would wait tables. Topless. Holly had been in the club and seen it. Several times, in fact. Actually Jamie from work had spent the last week of her sentence waiting tables just like that. And the waitresses were just as available as the dancers when it came to private, personal service. Holly hadn't requested that though. She wasn't a lesbian.

Actually, that was part of her whole problem. It challenged her, and gnawed away at her. It had been building for quite some time, and now it had become far too big to handle.

Holly wasn't a lesbian, but how could she say she was anything? What Holly was, was a *virgin*. A 28 year old virgin. Well on her way to becoming what they used to call an "old maid". She was cute. She was tall and slender, with shoulder length dirty blonde hair. But she had been too shy in high school and college, the time when everyone around you is the same age, and they're all exploring their bodies and trying new things. That was her chance. Everybody got laid in college, right? But not Holly. She could flirt with the guys and tell dirty jokes, but as soon as things turned serious, she got spooked and bolted. Guys started saying she was a tease, and maybe she had been. But now six more years had passed, and there were only two guys in the office even close to her age, and one was gay. The men who flirted with her now were in their mid 30s and early 40s. Surely they would expect a woman to know what to do by now? To not be *completely* clueless in bed? How do you sleep with someone when you've got that big a secret? "Oh by the way, you're my first, and I've never actually seen one of those in person before."

When it came to sex, the only thing Holly was good at was masturbating. She was a world champion at that. She got plenty of practice. Horny Holly with her desperate little pussy and her amazing fingers. For a long time that was enough. But the longer she went without a real man, the less her fingers satisfied her. They left an aching emptiness, and all too soon she needed it again. This morning she masturbated three times, waking up before her alarm to frantically jill off. It seemed she did that every morning lately. Then twice more before she even left the house today. And still she was a wiggling, wet mess. Her thighs clenched together and she could feel herself squish.

Holly sat her taco salad in the passenger seat, and looked down. The crotch of her jeans showed a large damp spot. She needed something more. Maybe get a big fat dildo that she could just cram right into her cunt. But she had tried carrots and cucumbers and bananas, and they weren't *right*. That hadn't stopped her from buying the biggest and thickest vegetables she could find, of course. The teenage boys who bagged her groceries got quite the chuckle out of it, and Holly just pretended that she was buying them to eat. But in the end, it was just more masturbation. She needed the real thing. She needed the real thing so bad.

She watched as the last of the chain gang of women stepped inside the door of the strip club. The fat deputy followed them in. The man would force them to get on the stage and take their clothes off. And if a customer found them desirable, he would send them to the back room where they would be fucked. Holly wondered how many cocks those women would see today. How many would they suck? How many would get shoved up their dirty little pussies? One or two? The women got here before noon, and Holly knew they would work them until late into the night. Five or six? Ten? Would they suck ten cocks today, getting huge mouthfuls of jizz, dribbling out of their mouths and down onto their tits? Getting it smeared all over their faces? Would any of them get a big thick cock rammed up her ass?

Holly couldn't really dance. If she were one of those girls, they would have her wait tables. She would be wearing those tight little orange jail booty shorts that barely cover your ass cheeks. Those and cheap little sneakers, and that would be all. Her tits would hang out for everyone to see, her nipples swollen and sensitive to the slightest breeze. The customers would look at her, every person in the building would see her, and the men would get big hard erections straining in their jeans. But she'd have some modesty because of those shorts. Would hers have a wet stain at the crotch? Holly didn't have to wonder, she knew the answer to that. And if the men wanted to see her pussy, they wouldn't get that for free like they did with the dancers. No, they'd have to pay good money to fuck her first. Cash. Holly had asked a deputy when Jamie was working there. They would have to pay fifty dollars to fuck her. But only twenty-five if they wanted to fuck her mouth. She wondered how many guys went to a strip club with at least twenty-five dollars? And of course, there was an ATM inside.

Some of the guys in college had been athletes. Young and fit and virile. They hadn't been able to fuck her back then. She was too skittish. But if Holly were one of those inmates, she wouldn't be able to be choosy. Anyone with fifty dollars and a hard cock would be able to take her. She would have no choice. The court would have *ordered her* to do it, as part of her *punishment*. Cock after cock after cock, rammed inside of her until her debt to society had been completely repaid.

Would she have to lick pussy? Holly wasn't a lesbian. She had only asked about Jamie out of curiosity. The ATM was right there, but Holly hadn't got any money out of it. It was even her bank and there would have been no withdrawal fees, but her card had stayed right in her pocket. She had sat and watched the dancers for several hours, nursing a few beers. Wondering about how those women felt. What they had done to deserve such... filthy and degrading treatment. Jamie had waited on her, and Holly had smirked at the shamed woman. 'I could force you to eat my pussy, but I'm not going to,' was the message. There weren't a lot of female customers inside, but there were some. Lesbians, probably, Holly thought. Would they make use of her mouth too? How many pussies had Jamie serviced in the week she had to work there?


She started her car. Her body was so fidgety and antsy that she couldn't sit still any more. She had to go somewhere, to get out of here. Go for a run, go to the gym, exercise. Get rid of all this nervous energy somehow. The thought of all those women being taken advantage of, forced into sexual degradation. Her heart was beating too fast and she was sweating heavily now, her breath deep and ragged.

Holly pulled out of the parking lot of the long stay motel and crossed directly over into the lot for the gentlemen's club. She stopped next to the empty Sheriff's van. No one was inside it now, but there had been ten women chained together and several deputies just a few minutes ago. She wondered again what they had done, and how long their sentences were. Jamie insisted that she had thrown her trash away, tossed it into a garbage can that was set up by the side of the road. "The wind must have caught some of it and blown it away, or maybe I missed. But I tried to get it in the can. It was just a Styrofoam cup and some old napkins." They had given her a month. Three weeks of road cleaning and then a week of being a court-ordered whore.

They weren't doing road cleaning anymore. What awful crimes had the women inside that building done now? Forgot to use their turn signal? No seat belt? Or something really horrendous, like shoplifting or public intoxication? What was that worth?

She looked down at the passenger floorboard of her car. It was a bit of a mess, and she really should clean it out. Fast food wrappers, coffee cups, paper sacks, empty plastic water bottles. A half-eaten taco salad bowl. Napkins from a dozen fast food places. You couldn't even really see the floor. How much trash was there? Too much. Several weeks worth. An image appeared in her mind, of her throwing everything out on the ground, right here. Right in the parking lot of this building, right this moment. Right in front of everyone. She could smear that taco salad all over the front of the van, let them know what she thought about their fascist crap.

What would they do to her if they saw?

With trembling fingers, Holly turned the key off and sat there. The safe thing to do would be to drive away right now. Or she could go inside and watch the dancers again. The muscles in her thighs clenched tightly, and she wondered how long until one of the deputies came back outside.

[cardman314]

Cute story. It's good to see some activity on this site again. Please continue, maybe I'll get inspired again.

[Master-Geass]

I'd be interested in seeing where this is going.

[Johnny Lawrence]

I'd be interested in seeing where this is going.

Thanks! I had a few different directions I considered going, but ultimately couldn’t decide what I wanted to do next. Then I realized, neither could Holly.

I figured there were three possibilities. One is that she just went into the strip club and continued teasing herself. At some point she’ll be horny enough to act, but she’s not quite there yet. The second possibility is that she waits for one of the deputies to come out and then intentionally throws some trash on the ground right in front of him, and lets herself be arrested.

The third option was the one I was slightly leaning towards, but still wasn’t sure. Holly gets out of the car and empties all of the trash onto the ground. She smears her taco salad on the windshield of the bus, writing “fascists suck” or something equivalent on the side with her lipstick. Then she sits in her car with excited nervous energy, keeping her hands locked on the wheel to keep herself from masturbating right there. And that lasts right up until a deputy walks out and sees everything. He spots her and she panics, throwing the car in gear and stomping on the gas to escape. Unfortunately for Holly, she accidentally put it in reverse and promptly slams into the front of the bus, totaling her car and stranding her. She looks out the window at the smirking deputy, and realizes that she’s going to be performing community service for a very, *very* long time. And that thought makes her give out a long, desperate moan as they pull her out of the car and cuff her arms behind her back.

She had been fantasizing about spending maybe a month there, but after the accident I thought she might get a couple of years. But I wasn’t quite sure that was the ending I wanted for Holly. I think I like her desperate and horny and unfulfilled. So that’s why I stopped where I did.