Solitary Con-fuckment

You've had a pretty testing day. Meeting everyone, putting up with Thunderlane's bullshit—he only got worse after you caught up with him, telling stories about his own greatness and bitching about the inmates to no end—and trying to get around the inmates without either getting in an argument with one of them or letting them take you somewhere secluded and have their way with you already.

Honestly, you thought you should have received a medal just for surviving your first day. Why did Celestia think to get you a job like this, again?

But none of that mattered now. Day one was over. You were clocking out, stamping your papers, and preparing to head out of the building to the freedom of non-prison life when you ran into Indigo, who looked particularly frazzled. "Hey there, newbie. How you holding up? Girls give you much trouble?"

You shrugged your shoulders, shaking your head once or twice. "Not the girls that were the worst of it, it was fucking Thunderlane, the asshole. I know you warned me about him, but you could've been a little more specific about just how much of a fucking tool he is."

"What, and spoil the surprise?" Indigo laughed, patting you on the shoulder. "Nah, you're right. He is a total piece of shit, but there's nothing we can really do about it, and no one wants to tell Nightstick just how bad he really is, because if they don't manage to get the complaints past the warden, it'll be their job on the line for even saying anything. Warden could make your life pretty miserable in here, so it's best to keep your head down."

You weren't entirely happy with this response, honestly. The fact that Nightstick didn't even know the all of it was shocking to say the least. "So what, you just let him go around doing what he wants? Hardly seems like a much better solution."

"You're totally, right, of course, but us staff have to eat, newbie. We still take him down a peg whenever we can. He knows he's hated in here, if that's any consolation." She frizzed up her already messy hair with her hands, running her fingers through the multi-coloured locks. "Argh, this day's left me completely beat. The girls have been driving me crazy, too, they know just how badly I wanna jump half of 'em. Think I'll be spending the night on Pornhub at this rate."

You still couldn't get over just how brazen Indigo was about sexual matters, but you figured you could give it a try too. Honesty being the best policy, and all that. "Yeah, they've been trying to get in my pants a lot too, though a little less with Thunderlane around. That said, with someone like that skulking around the place, I must look like the best guy in the world. Still, it does leave you a little pent up, you're right."

A wistful sigh as Indigo played with her shirt, throwing you a pair of doe eyes. "How about it, newbie? Wanna come over to my place and watch some badly acted porn with me? I'll bust out the popcorn if you buy the drinks."

"Y-you're serious, aren't you?"

"Pfft, no! Of course not!" She laughed, and you couldn't help but do the same, whether out of embarrassment or relief. "Why would I sit around watching a porno when I can just fuck you instead?"

Oh. Oh, shit. She really was serious, wasn't she? "You mean right now?"

"Well, not right now, we should probably get off of prison grounds first, but after a twenty minute drive? Sure, let's fuck the sexual tension away. Might take a few rounds, but I'll get it all out of you." Even a blink from her weakened you, a wink had three times the effect, and you knew in your heart already that you weren't going to be saying no. "So, how about it?"

It was hard to respond to her question with an actual precise response, so you talked around it as best you could. "I mean—are you all finished here for the day?"

"Yup! Clock out on the same time as you on Tuesdays, I checked the rota just to be sure." Her voice had a sultry little chime to it, and part of you couldn't help but wonder if she'd changed her shifts around to ensure you'd both get off at the same time. Maybe that was just the ego in you coming out, but it was still a nice thought to consider.

Nicer still was the thought of taking this one home. While the inmates had been enticing, Indigo had been on your mind all day, and now that she was here, offering herself up to you, any niggling thought in the back of your mind earlier that she might have just been teasing had vanished. Your throat felt a little tight, and you were fidgeting with the pocket of your uniform, but you managed to nod a couple of times. "You alright to drive?" you asked, partially in disbelief that you were actually going through with this.

"Hmm, nah, too tired." She led the way outside, her supple ass shaking in her tight jeans, and you followed its lead more than hers. She showed you over to her car, a fairly new looking Ford Focus in black, and after unlocking it chucked you the keys. You stared at her with an eyebrow raised, she gestured at you to get in the driver's seat. "Come on, newbie, haven't got all day."

"I'm not exactly insured to drive your car," you said, perfectly happy to be driving to destination fuck but not exactly looking to get picked up along the way. "Are you sure this is alright? Kinda weird for us of all people to be breaking the law."

She turned around with a grin, grabbing you by the hand and pulling you over to the driver's side. "First off, you'd be surprised how many laws get broken by staff around here. Seconddd—" she reached for her phone, pulling up a screenshotted document and handing it to you. You squinted, and your lips parted when you saw your name. "—I took the liberty of insuring you to drive it for a day, felt like I could use a chaperone."

For a moment, you just stood there in shock as she locked the screen and pocketed it. You couldn't help but notice that her home screen was a picture of another girl in lingerie. "You really had this all planned out, didn't you?"

"Heh, what can I say? When a girl sees something she wants..." she ran her fingers over your chest as she walked away, moving around to the passenger seat. "Get in, I'm not getting any younger over here."

This girl was amazing you more and more by the second. You opened the door and climbed in, growing acquainted with the interior, which was surprising neat and tidy. You'd kind of expected Indigo to be a slob, but as it turns out, pristine all around. Not that fake pristine like the prison's interior, more it looked as if she took good care of her belongings. You had to imagine that would bode well for you too.

You looked to the right, and there she was, already unbuttoning her shirt. You stared in disbelief.

"What? It's hot in here, running the A/C is expensive. I have blacked out windows for a reason, you know."

You took a second to glance at the windows, then thought about what you saw from the outside. "These aren't blacked out, they're tinted."

"Ehh, same difference," Indigo said with a wave of her hand, reaching behind her and fiddling with her bra strap. "No one's gonna complain if they see my tits, trust me."

Well, you certainly wouldn't. Still, you knew you'd only get complained at if you took any longer, so despite how badly you wished you could carry on gawking, you tried your best to ignore your stripping colleague and get the car going already. You put the key in the ignition and fired up the engine, grabbing the gear stick and putting the car into reverse.

You were a good driver, even when you had a show occurring literally feet from you. You managed to pull out of the parking lot and move into first without much issue, and before long you were leaving the prison compound, Indigo winding down the window and flashing her lanyard on the way. Not that any of the guards seemed to react to her state of half-undress, it's like it didn't even surprise them.

Before long, you were on a stretch of freeway, heading back towards Canterlot City. There were a few cars passing you on the opposite side, but the drive was a fairly quiet one, and soon enough, Indigo decided it was not only quiet, but boring. So she decided to liven things up.

The first thing she did was remove her bra completely. Next came her shirt, and while you didn't feel comfortable turning around to stare, you were more than happy to use the top mirror to catch a glimpse. She looked right back into it, and you flinched as soon as you were sure she noticed you, but instead of commenting, all she did was angle the mirror so you could get a slightly better view of her. "Thanks for being my taxi tonight," she yawned, pushing out her arms and arching her back as her perky breasts pressed forwards. "I'll make sure I pay you back..."

When she'd finished stretching, she had one arm laid over your lap, and her fingers were slowly snaking their way up your trouser leg. The moment you saw where this was going, it was too late. The traffic coming onto the freeway had increased, and there was no hard shoulder for a long way, the chances of you being able to bat her off were close to none.

But part of you had to admit it was really damn exciting, and that feeling was only amplified when she finally placed her hand against your hardening cock, rubbing it through the fabric. After so much teasing throughout the day, even that was enough to get you going, and you could feel your erection growing increasingly painful against your tight jeans, struggling against the constriction.

"Ooh, that looks uncomfortable... shall we let him out?" Indigo's voice was a soft, sultry purr, one that only made you all the more eager to say yes, but you didn't even need to respond. Already she was going to work on your belt, unbuckling it and pulling it back. All the while you forced yourself to keep your eyes firmly on the road, to not press too hard on the gas pedal, or do anything else impulsive to match the heavy beating of your heart.

But it was growing increasingly difficult to concentrate what with the sound of your zipper being undone and the feeling that you knew would soon follow. Indigo began to tug on your pants, and you shimmied around on the seat, trying to keep your hands on the wheel straight. What followed was a half-laugh, half-gasp as she saw the thing poking up from your briefs, blood rushing to it, hard as diamond from all that you'd endured over the last ten hours.

"Fuck, didn't realise I'd be getting such a treat today... how the hell are you single?" She gave it a small poke through your underwear, as if she was checking it was in fact real, and even that tiny second of contact was enough to elicit a response from you, only growing stiffer both in body and cock. Your eyes were glued on the road, drive, drive, drive... Don't think about what she's about to do, just enjoy it. Don't get too distracted.

But Indigo wasn't about to go ignored so easily. She quickly pulled your underwear down, exposing your cock for the first time, and instantly she was at work, taking a measure of her saliva and lathering it into your head, working it down to the base of your shaft and then moving her hand back up in a soft jerking motion. She repeated this a couple of times, priming you for what came next, and every brush of her hand was enough to make you pant, to make you sweat in your seat as you prayed to god that you wouldn't suddenly crash.

There was a thrill that came with getting jerked off while driving, but it didn't compare to what came next. Indigo dipped her head lower, twisting beneath your outstretched arms that clung the steering wheel for dear life, and within seconds you could feel her luxurious tongue twisting its way around the head of your cock. She wasted no time in preparing you, and in moments she was moving to the main course, parting her lips and planting soft kisses against your tip that moved and twisted into French smooches as she worked her way lower.

"Fuck..." her tongue wrapped around the underside of your cock, sending a jolt through your body, making you seize up for a moment, but you were determined to grow accustomed to it, to keep on working through it and ensure that you didn't screw up. Every time you thought you'd finally grown used to the ministrations of her tongue, her seemingly ungodly skill with her mouth, she switched up her motions, beginning to travel down your length like the naughty nympho she was, set on taking every last drop you had to offer.

She moved up and down with intensity, a hand at your base softly wanking you all the while, and as she moved the pair in tandem, you'd ever so often begin to relax into it before she'd take the hand away, forcing the rest of your cock into her waiting mouth, sputtering on it and getting you as sloppy as she could, pulling back for air and then diving straight down. Even with your length, she was managing to put on an amazing performance, and the vigour with which she played with you, the energy with which she moved, it was enough to have you missing breaths, heart palpatating in pleasurable anxiety even as you began to wonder whether any passing cars had realised just what you were up to.

A part of you that you never realised existed hoped that they could. You'd never done anything like this in public, or thought that you'd even get turned on by it, but there was something about the risk of being discovered that spurred you on, and before you knew it you were ever so slightly pushing up against her mouth, as lightly as you could without taking your foot off of the pedal, knowing you were living dangerously but only encouraged by the fact.

Indigo didn't seem to care, she was crazy and cockstarved, worshipping your length as if it was the best meal she'd had in a long time, as if the cumshot you could give her was the most important thing in the world. Maybe to her, it was.

Then again, you were starting to wonder what was more important right now. Surely not crashing, that had to be an important thing, but also, this was a fucking good blowjob. The way she licked her way up when she was coming for breath, swirled her tongue on the way back down, she made sure that every moment was filled with an inordinate measure of pleasure, feelings that shifted through your whole body and found voice in your steadily growing moans.

It wasn't long until you were getting close, and it was a good thing too, because the sat-nav was telling you to turn off of the freeway only two minutes from now. Maybe Indigo knew this, maybe she realised just how well she timed these things, because the minute the announcement sounded out, she was going into overdrive, causing shock waves to crash through your body as she brought you to the edge, pulling you out of her mouth and slowly flicking the edge of your cock against your lips.

She pulled her head back, her hair brushing over you as she repositioned, and before long she was jerking you as she slapped your head against her firm tits. You wanted to look down at her, you wanted to stare at her as you covered her with your cum, but you could only look at the road and you knew it. You could feel yourself getting closer, and you desperately tried to spy the last moment with the top mirror, but she'd moved it out of angle, and she probably knew it.

Her hand moving impossibly fast, your breath catching as you felt your orgasm rushing over the barrier, and before you knew it you were painting her beautiful body with your cum, bliss etched on your face as you plastered her with cum, a small chuckle escaping her lips as she let you coat her without complaint. She took every spurt you gave her, jerking you until you were completely spent and then a little more for good measure, and once she was finally finished completely blowing your mind, she reached for a box of tissues.

"See? Told you I'd pay you back. That was just the beginning."

You know what? Fuck it. This job might have been hell in some respects, but it came with some pretty damn good perks. Plus, you didn't crash. You're doing pretty great right now.