Short Story

Dare Night

Some couples have date nights; we have dare nights

Content Notice: misogynistic abuse

How can it be this difficult to suck a cock?

Usually, if other people are involved, my husband arranges everything. He’ll pick out a likely man, get talking to him, casually let slip that his wife is a freak, and things develop naturally from there. Then I move in and complete whatever the dare is.

That’s our thing. Some couples have date nights; we have dare nights. He knows me well enough to come up with a dare that plays to my kinks but safely pushes my limits. So that means somewhere semi-public, or with a stranger, doing something degrading.

Whatever he comes up with, I do it: I might be shy, but it’s a point of pride that I have no shame. I have never failed a dare.

So how can I be failing this one? He gave me thirty minutes to swallow someone’s semen. He enjoys making things difficult, so I couldn’t just call a friend. It had to be someone in our local bar. But the bigger problem was my husband refused to do the talking for me this time. I had to approach a man and ask for what I needed.

The bar is heaving tonight, so finding the right target took me a few minutes, but I struck gold: a middle-aged man wearing a wedding ring, and drinking alone. Statistically, the person most likely to be in the market for no-strings oral sex.

I’ve never been much of a flirt, and I didn’t have time for subtlety, so walking up to him and saying, “Hi, please may I suck your cock?” seemed like the best approach.

I needed to down a double vodka before I had the nerve to say that in a crowded bar, and when I finally did I only got as far as, “Hi — ”

He held his hand up to stop me, stared at my microskirt, then my cleavage, then looked me dead in the eye and said, “I can’t afford you, love.”

I had to explain — to him and everyone close enough to overhear — that I wasn’t a sex worker, I just wanted to take him out to the alley to give him a blowjob, because I needed him to come in my mouth, because I had to swallow someone’s spunk, soon.

And he said, “No thanks. I don’t like blowjobs.”

He’s lying. I know he’s lying. What man doesn’t like blowjobs?

He picks up on my scepticism, and explains. “It’s the teeth. I don’t like having my dick between a woman’s teeth. It’s not that I don’t trust you, I’m sure you’re an honest, hard-working whore, it’s just this irrational fear I have. Phallodontophobia, it’s called. Sorry. Good luck with your quest, though. You’re a bit old for a tart, but you’re not so ugly, not really. I reckon there’s loads of blokes who’d be happy to fill any hole you offered them.”

It was hard enough asking him; I am not going through that again with ‘loads of blokes’. I chose this man, and I will swallow his spunk. “You can fuck me.”

Now he’s interested. “I thought you wanted me to swallow my spunk, like a porn star?”

“Exactly! We can go out to the alley, and you can fuck me. When you’re about to come, pull out. We’ll do the porn thing: I’ll kneel down and you can shoot in my mouth. That way your cock won’t go anywhere near my teeth, but I’ll still get to swallow your cum.”

He tilts his head from side to side, like he’s weighing up the pros and cons of a free fuck. “Can I take you up the arse? You look like the sort of dirty slut that enjoys anal.”

Time is too short to haggle, and the way he’s talking to me is pushing all my buttons, so I want to say yes, but… “I haven’t got any lube. It’s a straight fuck or a handjob. Please?”

He considers his options, agonisingly slowly. “I’ll need a condom. Better safe than sorry, eh? I don’t know how many men paid to fuck you before you started begging to give it away.”

“I am not a sex worker!” If I was, I’d have condoms, and he could fuck me, and I could complete this dare.

“Yeah, sure, you only dress like a whore. I still want a condom. There’s a machine in the gents.”

Yes! This is going to work. He can wear a condom to fuck me, but pull it off before he pulls himself off.

I wait for him to go to the toilets, but he doesn’t move. He just stares at me for a second, then says, “They’re three quid. Do you need change?”

I check my purse; I’ve got enough coins. “Right. I’ll go get you a condom then.”

“Great. What’s your name, by the way?”

“Crystal.” That’s the name I always use for dare nights. I like Crystal, she’s braver than I am.

“Nah, that’s not your real name. That’s a stripper name. You’re never a stripper, no one would pay to see those saggy tits. Off you go then, Crystal, you filthy bitch. Meet me in the alley when you’ve got condoms, and if you’re a halfway decent fuck I’ll let you taste my spunk.”

With the pub this busy there’s no point trying to be discreet, so I march into the gents, ignore the old man standing at the trough, and feed my coins into the machine. It delivers a slim pack of Durex Pleasuremax. Oh great, condoms designed to make him last longer. Just what a girl with a deadline needs.

As I’m leaving, the old guy calls after me. “Trollop!”

That’s such a quaint word, and so much nicer than ‘filthy bitch’, that I can’t help but smile. I reward him by letting him watch as I take off my G-string and tuck it in my bag.

Right, I’m prepared. A trollop’s gotta do what a trollop’s gotta do, and this trollop is going to be a filthy bitch.

My ‘date’ is waiting for me in an alley that smells more strongly of pee than the gents did. The stench is helpful: his abuse got me in the mood, and flashing my arse in the toilet was fun, but I’m not ready to fuck. A few deep breaths of that heady aroma while I’m rubbing myself in public should be enough to have me dripping by the time he’s rubbered up.

And the wetter I can get, the better: he’s got his cock out now, and he’s a big lad. I chose well.

Or maybe I didn’t. Either seeing me lift my skirt and go to town is distracting him, or he’s clumsy, because he’s struggling to get the condom on. He’s so slow I’m tempted to go back in and offer to blow the old geezer instead, but with the luck I’m having tonight he wouldn’t be able to get it up. And while the guy I’m now alone in a dark alley with wasn’t eager to fuck me, I don’t want to piss him off by blueballing him when we’ve got this far.

He tears the first condom, but manages to get the second one on. The bar’s dumpster is about the right height for me, and it’s somewhere to put my bag, so I lean on the grimy lid and brace myself for his cock, assuming he won’t be gentle. And I don’t want him to be: hard and fast would be best, because I am running out of time. The quicker he is, the sooner he’ll finish.

He doesn’t even start. “You sure I can’t fuck your arse instead? ‘Cause that’s the nastiest cunt I’ve ever seen. It looks like a blind man tried to make a ham sandwich. Nah, forget it. I’ve changed my mind.”

“Please! I really need you to fuck me.”

“Ten quid.”

“What?!”

“I’m not giving a skank like you a charity fuck. I’ll do it for a tenner.”

So now he’s the sex worker? “Whatever! Take some money out of my purse and fuck me, quickly!”

He grabs my bag, tips everything out on the dumpster — and the ground — to find what he wants, and helps himself to a twenty pound note.

Suitably compensated, he grabs a fistful of my hair, pushes me down until my face is pressing against cold, sticky plastic, then twists my head round so he can spit in my eye. He nudges his cockhead between my lips, I brace myself again, and he stops. Again.

“Beg for it.”

“Please! Please fuck me. I need your cum, so please, please feed it to me! ”

I brace myself again, only for him to slide his full length slowly and gently into me. “Fast, please! I need it hard and fast!”

“And I need to feel something. I knew I should have fucked your arse. How many dicks have you had up here, you stretched out old slut?”

“I’m sorry! I’m sorry I’m a slut! Show me how sluts get fucked.”

That does the trick. He starts pounding me like he heated up a Fleshlight and he’s desperate to finish before it goes cold. I’m nothing to him but a tame cum dumpster, returned to my natural habitat.

Between his contempt, the rough handling, this filthy alley, the saliva running down my cheek , and a big cock hitting all the right spots, I should be on course for a trashy orgasm. But my time must be nearly up, and the thought that I might fail a dare trashes any hope I had of coming. I just stand there and let him use me, and even that doesn’t help.

He stops abruptly, yanks my head up, then thrusts hard, once, slamming my thighs against the cold metal of the dumpster… and I feel him throbbing deep inside me.

Did he just come?! We had a fucking deal, I paid him to feed me his spunk!

He pulls out, and slaps my arse. “No wonder you have to beg for it: I could have found a tighter cunt in a cattle market. If I’d known you were such a sloppy fuck I would have taken fifty quid.”

The reason I never fail is because I never give up. I spin round, optimistically, and drop to my knees. It does me no good: I’m face to face with a rapidly deflating cock. “No! You were meant to finish in my mouth!”

He grins. “Amanda, baby, I told you I was going to make this one difficult. Anyway,” he checks his watch and hands me the condom, “You’ve still got a couple of minutes left.”