The Car Boot Bet

Despite the blankets all around me, I've been really uncomfortable for about fifteen minutes now. It's pitch black and I'm practically naked.

Then there's a noise, and the light of a torch floods in as my girlfriend opens the boot of the car, looking down at me.

"We're here," she says. "Get out."

Awkwardly, I pull myself up, grazing my chastity cage on the lip of the boot as I get out. It's the only thing I'm wearing. I grin fiercely, then start to feel the usual mix of emotions -- the thrill of being outside, naked and vulnerable, the horror of being outside, naked and vulnerable, and the dual excitement and dread of what's to come.

I shiver in the cold, feeling sweat on my palms and under my arms. We're parked on a small country lane, in what I think is a lay-by or passing place, the torch the only illumination for as far as I can see. Long hedges stretch along the road on either side, the moon bright in the sky. The road is rough underneath my feet. I have absolutely no idea where I am, and that's kind of the point.

We'd talked about meeting new people, so I'd half thought we might be going to a party, which had always appealed, but this... this kind of fills me with terror.

"End of the road," Amy, my girlfriend says. She's fully clothed, and already working her way around to the passenger seat. "Clock's ticking. Once we get back to Dan's place, I roll a die every ten minutes. I'll take off that many clothes and take half that many shots. If I roll when I'm naked, I roll the forfeit table."

I swallow, looking at her outfit. Shoes, socks, jeans, a jumper and something underneath. Maybe a bra and a pair of knickers, but there's no guarantee. Nine items of clothing, tops, maybe seven. Two or three rolls, maybe four if I'm really lucky. Half an hour before she hits the forfeit table that we'd written together after our last adventure. The fringe benefit of being completely sober is that I can work out maths like that. The main problem with being completely sober is that I'm completely aware of how stupid this venture is.

How delicious. How amazing.

How shameful.

We'd both been with other people occasionally, but it was still quite new. This time, we'd combined it with a bit of risk. The forfeit table includes everything from gentle teasing to full sex.

Just not with me, which I hadn't really expected.

"If you get back before I roll a forfeit, you get unlocked and can choose between fucking me and fucking Dan's wife," she says, grinning, looking me up and down. "If you're more than forty-five minutes, I drop the key to your cage in an ice cube tray of blackcurrant juice, and it goes in the freezer along with the five other ones and you have to defrost them with your mouth. If you're more than ninety minutes, I start dumping the ice cubes out in the garden. If you're more than two hours, I tell Jen, then all of the cameras come on in the house, and you know Jen doesn't like that."

Dan and Jen are the couple we're playing with. We all switch, but I get the impression that Dan prefers to be dominant, whereas the rest of us basically do anything. Dan's in the driver seat right now. Jen's back at our house, in her underwear, cuffed to the sofa with a bucket in front of her. Being live streamed is a bit of a soft limit for her, alongside a few other kinds of humiliation, so if she has to pee, she has to do it in the bucket, but once her knickers are off, they stay off, and if she needs to go twice, she has to pay with her bra. Dan's also rigged an ingenious tube so that she can drink when she wants, but the machine loads shots of vodka or drinks of water at random, so she's in a bit of a predicament.

We're young, we're a bit rash, but we've got no dependents, work from home, earn a decent amount and live in the countryside, so when we found Dan and Jen, things got really interesting, really quickly.

It's highly likely that if Dan and Amy fuck, they'll do it in front of Jen. Of course, if the timing's right, I could walk into the lounge, my dick locked up, broadcast to the world as my wife fucks another man and his wife looks on, peeing into a bucket. Being locked up and having my key given to another woman is a soft limit for me, so I guess we're playing tonight. Amy's a bit mischievous, and often dumps me naked in the middle of nowhere, at a party of strangers, or halfway down the main street at 1am. It's always quiet, there's never CCTV, but there's always, always risk and challenge.

I don't know why these things appeal to my sense of the forbidden, but I'm both scared shitless and horny as fuck.

"See you around," Amy says, climbing back into the car and slamming the door. Dan revs the engine, then drives off down the road. The brake lights leave red dots dancing in my eyes for a few minutes, then I'm all alone in the darkness.

I don't have anything. No keys, no phone, nothing. If I'm caught, I have to improvise -- my pre-prepared lines are that I'm either a naturist (unlikely) or that it's my stag party and I really need to get back. Neither implies anything sexual or any intended offense, so I'm not technically breaking any laws. Mind you, it's not the police I'm most worried about; a group of drunk guys deciding that they want to kick me around would be pretty disastrous.

I'm not sure which way to go. From past experience, Amy often does loops around the countryside so that I can't simply try and follow the car back. If I head back the way we came, or the way she's gone, I could be moving parallel to or away from the house.

She's tricksy, and the other thing I have to be careful of is her phone calls. The third time we did this -- this is six, by my reckoning -- she somehow organised the local Rambler's society to do a midnight walk for charity right along the path where I was. I ended up crouched in a thorn bush for twenty minutes while a group of fifty- and sixty-somethings ambled past happily chatting about what a lovely fresh night it was and how bright the moon was, while she was getting fucked by Dan for the first time.

The fifth time, I almost walked into the lounge where her sister was sitting, watching a film. Amy hadn't mentioned that she'd been coming over, and I had to wait for over an hour until she'd gone home, losing the bet by almost ninety minutes. I don't really want to talk about what I had to do as a result, but this time, the sixth such party we've had, I'm being more careful. My sex drive is a strange mix of risk and wanting to beat a challenge, and Amy knows this pretty well.

I need to get off this road. I hurry back along it, then see a gap in the foliage, cautiously climbing through, watching my step, into a grassy field. Phew. If it'd been a ploughed farmer's field, it'd be much slower, and muckier. I've done that before and it was... bad, not to mention that I was paranoid that I'd cut my foot on a stone. Thankfully there's not too much broken glass just left lying around here because it messes up the farm equipment, but that's another reason why I get off the roads as quickly as possible.

My heart sinks as I hear the roar of traffic, but I head towards it. It's risky, but if I can find a sign, I can at least try to orient myself.

I reach the top of the shallow hill and my heart sinks a bit more as I look down on the motorway on the other side. There's only two easy ways across: the road we came in on where there's a mini-roundabout, and a cage-like bridge about five minutes away from here. I'm almost certain that Amy will have alerted people to both.

Or I can try and cross directly, but it's busy, cars speeding past incredibly quickly. It's a fucking motorway, obviously. No-one would be expecting a pedestrian to cross. And that's maybe why I choose to do it.

I hurry across the field to the treeline; there's a steep slope down, and then the road. There's something going past every few seconds, so fuck knows how I'm going to manage this.

I wait, hoping that no-one can see me behind this tree, but the longer I stay here, the higher the chance of someone coming along with their headlights on full beam and spotting me.

A pair of huge trucks go by and there's a wave of impatient cars behind them. Gambling that this will have jammed up traffic for a bit -- and then cleared it -- I hurry down the slope after the last one passes and get down to the barrier, crouching down as a single motorcyclist goes by.

I hop over the metal, feeling incredibly exposed. This is insane.

Then I run, faster than I ever have, across the first part of the motorway. A car flashes by on the other side and before I can lose my nerve, I vault over the barrier again and sprint across the second section, another car going by on the section behind me.

I must have been seen, but I don't stop, jumping over the last barrier and desperately half-running, half-crawling up the steep grassy bank to the next treeline. A few cars go past and one honks, but none of them stop; I guess none of them can.

I keep moving, but then disaster strikes. I run into a high, wooden fence, which seems to go for as far as I can see. It's solid -- there's no way I can slip through or over it.

Fuck.

The good news is that I'm not visible from the road, but the bad news is that it seems to go on for ages.

I try to orient myself; if I'm on the motorway, I do need to keep going in my original direction to get back. I glance up at the fence, but there's definitely no chance of climbing it -- there's no foot or hand holes.

Dammit. I try and stay behind the treeline, following the fence, and it goes on and on. I think I'm going in kind of the right direction, and eventually, the fence stops and becomes a wire fence before another grassy field. I feel an incredible urge to pee, but then get another shock.

Literally. I put my hands on the fence, only to get a buzz -- it's an electric fence. Fuck.

I can't even see the edge of the field, and the trees to my left stop in a few metres, so if I wanted to get further along, I'd be seen for absolutely sure.

Crap.

I take a breath, then run and vault over it, getting a slight buzz on my toes and falling over at the last minute, hitting the grass harder than I'd thought, but it's better than rolling naked onto concrete -- which I've done before, and it's not pleasant, trust me. I take a moment to get myself together and look for any injuries, but I think I'm ok.

I try to scan the field, praying that it's sheep rather than cows -- or a bull. That would be really terrifying, and I'd have to take my chances with the motorway.

I can't see anything, so I hurry along, keeping to the right-hand side of the field. It must have been fifteen minutes by now. I think of Amy, sitting in the house with Dan, getting drunk and gradually taking off her clothes. What if she rolls a six first time? If she's not wearing any underwear, she could basically be naked right now.

Dammit.

I hurry along, reaching the end of the field and hearing a 'baa' distantly behind me. There's a metal gate, which I gratefully climb over, following a poorly-surfaced road, which slows me down -- there's all kinds of rocks and potholes that could slow me down. A broken ankle would be catastrophic.

The farm buildings next to me are quiet, and as I come out onto the main road, I work out exactly where I am.

Shit.

I'm on the wrong side of town. Not too far from it, but going around will definitely slow me down. I mentally plan a route, and then try to think about which way Amy would go; probably through the woods.

I duck back down the track as a car goes past, then hurry out along the road, jogging down to the footpath that runs alongside the canal. This is also risky -- plenty of the boats are occupied, and there's almost nowhere to hide, but it's quieter. One person looking out of their boat at the wrong time and calling the police -- or coming at me with a boathook -- would be it.

I shiver; I don't know if it's with fear or excitement. Or both. Probably both.

Once I calm down, it's actually incredibly chilled jogging along the towpath. There's nothing around, and I can see a bit of the way in front of me because of the lights from the canal boats parked -- moored, I guess. It's really peaceful here, and I could kind of get used to this.

I try to spy a clock in any of the boats, but can't see anything, and just follow the water along for a bit.

My pulse races as I see a dogwalker on the other side of the canal, but I manage to duck into some trees until he passes, so I'm pretty clear. I pad onwards, eventually reaching the park. On the other side of the park, there's two roads, then I'm there. Unfortunately, it's a pretty big park, and there's a pub on the road, so fuck knows how I'm going to make this. My dick cage is also starting to chafe a bit, although I'm grateful that we went for one with an integrated lock, rather than an external one, because then I'd be jangling every step. Still, I really, really don't want to get caught.

Then I almost do.

Deep in my thoughts about the pub and the roads, I almost miss another dogwalker, just managing to slip behind a tree as they approach from the other direction. Their dog, a large German Shepherd, starts to sniff around and my pulse spikes. This is it. I'm going to get caught.

"Is someone there?" a woman's voice calls out.

I decide to try a play I've considered in the past. "Sorry," I reply. "Just answering a call of nature. The loo on the boat's not working."

"Oh dear," the woman says, coughing. "Well, I'll carry on then."

"Thank you," I say. "Sorry. Have a good night."

She doesn't reply, and after a moment, I carry on towards the park, finding the path that I'm looking for, and a narrow line of trees that I can duck into for cover if I need to. Then I see the spark of a lighter up ahead and -- staying low -- run over to the other side. Then there's the spark of fire, and loud laughter -- looks like a group of kids has set fire to something in a bin up ahead. Dammit. A bike moves in the distance, and I feel my palms sweating, my dick shrivelling up, and I realise that I need to get further away. Fuck.

This is taking me further away from Dan's place, but I don't really have a choice. I'd hoped to leave the park by a quiet exit, but I can't. There's two others; the main exit, and a narrow path leading to a gate that's sometimes locked.

Or...

I have a thought and dash across the edge of a playground, finding a small track that leads towards a stream, which I hop over, hurrying along down towards a broken section of fence.

Then I hear something and skid to a halt, ducking behind a tree.

There's a naked girl waiting by the fence, and her hands keep moving as if she's reaching for her phone, then smoothing them on her thighs. She looks familiar.

I pause, not sure why she's there. It's dark, and the park's technically closed.

She shuffles around, then clicks something. There's a distant sound, a snap, and she strikes a pose, covering her nipples.

Fuck. It's my cousin Andrea.

What the hell is she doing here?

I can feel my cheeks growing hot. Dammit, what if she sees me? I can't move, I'll probably step on a twig or something.

She moves her fingers down to her pussy, and something clicks again. I glance around, trying to see what's happening, but it's almost a full minute before I realise. Wedged into the crook of a tree is a camera, taking photos of her as she now puts a dildo into herself.

There's a low buzz... fuck, I guess it's a vibrator not a dildo. A red light comes on the camera... she's filming herself masturbating in the park! My dick is suddenly painful against the cage as I see her cum, sagging back against a tree as she gives the camera a smile. What the actual fuck?

Quietly, she turns off the vibrator, retrieves the camera, and slips a sundress over herself, putting some flip flops on and heading out of the park.

Damn. What the fuck was that all about?

I wait for a moment, then follow after her, seeing her car pull away just as I reach the road. I decide to abandon all pretence -- Amy's tricks only go so far, and she usually relies on me getting into my own kind of trouble in town. I look around, wait for a car to go by, then just sprint over the road and head up the avenue that leads to our road.

Luck is with me; although there's a few lights on in the houses around, I don't see anyone and I don't see any curtains twitch. It's late, I guess.

Ok, final straight. I turn down the road, and my heart sinks as I see my cousin's car outside the house. She's outside, and the front door opens a crack. I skid to a halt, just out of sight.

She gets handed something. It's a blindfold, I realise, as she puts it on. She's guided in, and I hurry after them, realising that I'm still naked on my street.

I usually go around the back, but this time knock at the door. Amy answers in her knickers, grinning at me, and I take a moment to admire her perfect breasts and small, pink nipples. She's so hot. Then there's pain and I suddenly and immediately remember the cage, and Amy covers her mouth to laugh before holding up one finger and putting it to her lips.

She takes a step back and I enter the house, feeling a surge of relief as the door closes behind me. Safe at last.

Amy holds up her phone, which shows a stopwatch: 37 minutes. She hands me the key from around her neck and gratefully, I unlock my dick, putting the cage on the side table, then wash the crap off my feet.

I'm about to head into the lounge to see what the deal is with Jen, but Amy stops me, scribbling a note down.

"New game," it says. "Did you see your cousin? I've been paying her to take naked photos and sexy videos for some time. It started off fairly innocently, but it turns out she's got a thing for money. You can still choose to fuck me or Jen now, but if you do, Andrea's photos and videos will be sent to your aunt and uncle's email addresses, not to mention a few of her work colleagues. All you have to do to save your blindfolded cousin is roll a die. If it's one or two, she sucks off Dan while you go down on Jen. If it's three or four, she sucks you off while Dan goes down on me. If it's five, she gets fingered while you and I fuck, and Dan and Jen fuck. But if it's six -- since you've been such a good boy and evaded almost all of my traps -- you penetrate your cousin from behind, then she sucks you off tasting herself on your cock. If that happens, Dan and Jen fuck while I finger Andi."

I swallow. I don't really have any choice, do I? The question is, after tonight, is this something I want to be part of?

I hurriedly wash my feet in the bathroom, then come back into the lounge.

Amy puts a die in my hand and I roll it on the table. It spins, flips and lands.

Six.

Shit.

Amy giggles, and leads me into the lounge, where Andi waits on all fours on a couch, naked again and blindfolded, unknowingly opposite Jen, who is bound and nude. Jen grins at me, and my dick hardens. I take a step up behind my cousin, seeing her pert ass, her big tits, her wet pussy, and lay one hand on her ass.

"I want to be your slut," she says softly. "Fuck me hard."

Fuck it. Can't be a good person all the time.

I slide my cock into her pussy, feeling it hot and tight around me. She moans as she's penetrated by a stranger, gasping as I go deep inside. I can see Dan and Jen start to get it on, making out on the sofa on the other side of the room, Jen now out of her cuffs.

I pull out as Amy steps up alongside me, then walk around to the other end of the sofa, touching Andi's face with my hand, then running the tip of my dick down her nose and into her waiting mouth. She enthusiastically sucks and tongues my cock, occasionally pausing to moan as Amy's fingers search out her clit.

Damn, this feels good. Amy starts to play with herself with her free hand, and the look on her face drives me over the edge, my cock spurting cum into Andi's mouth, which she enthusiastically sucks down and swallows, before her own orgasm arrives.