Two Roommates and a Monopoly Board

I guess if I learned one thing from all this, it's never to play monopoly with real money.

Well, kind of. I'm not that rich.

Shit. I'm getting ahead of myself. Let me start from the beginning.

Emily and I share a flat at university. I'm still not quite sure how it happened. I'd been looking for a place with my mate Steve and a few other friends -- you know, bigger place, lower rent. We were just at the end of first year, so I figured I knew everyone pretty well.

Guess not.

Anyway, Emily turns up one day to look with us -- friend of Sam, who I knew least well of all of them. She's pretty gorgeous; brunette, skinny, dark blue eyes, amazing cheekbones, long legs. I tried not to stare. Which, as it turns out was pretty easy, because an hour later, we're turning in for lunch and the estate agent calls, asking for two of us to come down to the office to pick up a new list. Yeah, they can't email us apparently because it's too in demand. Weird.

Emily and I go, and the next thing I know, I've got a text from Steve saying he and the others are taking a place and there's no room for me or Emily. What a fucker.

So we're thrown together and end up seeing a penthouse flat for two. Weird how it's available for students but it's literally just come up -- got amazing floor to ceiling windows in the lounge; we're the first people to see it, the landlord has no idea how much to charge and we take it right there and then.

Emily actually turns out to be great fun. Good laugh, and we have a common interest in philosophy. When we move in together in the new year, she teaches me yoga; I teach her to fence and tutor her in logic while she tries to teach me French. We play chess, try premium vodka, laugh a lot.

It's just after the January exams and we've got time to kill. We're both drunk -- we managed to win quite a lot on the horses earlier in the day and don't really know what to do with it. I realised I'd never actually been into a bookies, and we each put too much money on a horse that won.

We've been working our way through a new bottle of vodka -- the first thing we bought with our winnings -- and are admiring the lights over the town. We've got a great view from this floor.

"I have an idea," Emily pronounces, and rummages in a cupboard and brings out a monopoly board. "Let's play with real money."

I laugh. "Come on," I say. "We didn't win that much."

She giggles and sways. "Well, we could divide it by ten?"

And so it is that we end up playing monopoly with real money, everything divided by ten, so even the most expensive property is £40.

We have to pool money to make a bit of a bank -- splitting it evenly and recording it, but there's a bit of a difference between real monopoly and game monopoly.

I run out of money quickly. Shit. My usual tactic is just to buy as much as possible, and when I start get to the midpoint of my cash, I buy stuff or build stuff only when Emily is closing on it. For some reason, it doesn't seem to work as well as usual.

Fuck.

So it is that I'm basically broke, except for £5. She's not landed on my properties for a while and I've dodged hers. I've got more than her, but if I land on anything of hers, I'll have to sell stuff, whereas she's got cash reserves.

"Uh, do we do credit notes?"

She laughs, takes a drink and looks at me. "Well, not the usual kind," she says. "That would be cheating. You'd have to advance something pretty special, since we're playing for money. Or sell properties like the rules say"

I think for a moment. I almost offer chores, admin, cooking. But for some reason I don't.

"For £100, if you win, I'll streak for the rest of the evening."

Emily's mouth opens, then she laughs. "Oh, I like this. Tell you what, yes, and also, I'll put one down too. I'll take half as much, and if you win, I'll be in my knickers."

"What?!" I say. "You don't even need the money!"

She laughs. "Oh I know, but where's your senses of fun?"

I roll the dice and land on the Strand with a hotel. It's hers. Fuck. That cleans me out.

She grins and rolls the dice, landing on community chest and winning £4.

"Crap," I swear. "You have the best luck. It can't last. Look, for £200, I'll be your servant for the rest of the evening."

Emily laughs so hard she starts coughing. "And you'll be naked? You sure you want to promise that?"

Well, I was envisaging washing up and butlers in the buff, but the way she said that ... makes me swallow hard.

"Your luck can't last forever."

"It's your life," she says shrugging, handing me the cash.

My next roll doesn't land me in trouble, but hers does, and I get some more money in the bank. Unluckily, a brutal back and forth begins, alternating between her landing on my properties and me landing on hers. It's bizarrely intense for a board game.

She has to sell off some properties to pay me, then it swings back and I do. I can't think of anything else to promise... although my mind is starting to make a few suggestions.

Then she gets a chance card telling her to make repairs on all of her houses, and she has to sell more off. I land on one of her properties and pay her loads, then get the same card on community chest. She gets a double, lands on one of her properties and then lands on community chest and gets the same damn card.

"Fuck!" she says. "How many of these cards are there?"

She's almost out of cash, but then I land on another of her properties, have to sell off houses and then get the same card on chance again.

Neither of us have any houses or hotels left.

"Shit," I say. "Bank won?"

She giggles. "Draw? We both do what we said?"

Fuck. That would mean I'm naked and her slave. "Fuck no," I say. "I've got far more to lose than you do."

She raises one eyebrow. "Negotiation," she says. "I'll go first."

I shake my head furiously. She takes another shot of the vodka, which is weird, because we've been sipping it so far.

"Second negotiation," she says. "And you can keep the money."

I raise my eyebrows. Shit. That's a lot of money. I find myself nodding, sweeping the money into a heap and taking it all to my bedroom and dumping it on the desk.

Hey, I'm drunk, cut me some slack.

When I get back, she's in her pants. I'm literally stopped in my tracks. My hot flatmate, topless and only in a pair of skimpy knickers. Small pink nipples quite erect, long legs and curvy hips. Shit.

Then I realise what I have to do.

I peel off my t-shirt, and slip off my shoes and socks. I pause, trying not to look at her; I'm already a little hard.

I unfasten my jeans and pull them down; thank god I've worn good pants today.

It's weird the thoughts that go through your head.

Then I'm pulling my pants down and suddenly I'm naked in front of my flatmate, in our fifth floor apartment. I distract myself by taking a shot of our expensive vodka.

"That," she says. "Will be the last act you do of your own volition this evening."

I look up at her in surprise. Shit. I nod and sit down.

"First things first," she says. "Put this on."

She slides something across the table.

Fuck.

It's a dick-shaped cage.

"When I win a bet," she says. "I like to make it memorable, ok? But let me sweeten the deal. If you continue and are obedient, I'll put my knickers on the pile of cash on your desk."

Fuck.

I force my swelling junk into the rigid plastic cage and pull it around my balls. There's a lock at the bottom, which I lock and pass her back the key.

Shit.

I have no idea when I'll get that back.

"Ok Ben," she says. "I want you to feel really naked as well as being naked. Tell me a fetish you have."

Shit.

"Leggings," I say. "Lycra ones. They're elegant, sexy ... fuck."

"A fantasy you're ashamed of."

"Being watched having sex."

And so it continues. Last sex I had. Naughtiest sex I've ever had. Naughtiest thing I've done in this flat. Whether I shave my pubes.

And all the while, my dick is constrained and she's topless. Fuck.

Then she goes and gets a vibrator and touches it to the top of the cock cage. Fuck. It's pleasurable and painful instantly. My dick is pushing against the cage, and I can feel like a sore ... fullness. Shit. I can't get hard. Not really.

She takes it away, giggling. "Most sensitive part of your body, besides your dick."

Fuck.

"Nipples," I admit, making her laugh more.

Then she's on her knees, crawling towards me like a cat, making little miaowing noises. Her face nuzzles my thighs and before I know what's happening, she's closed her mouth around the cage. There's a slit at the end, and I can feel the warmth off her breath, the presence of her tongue, but she doesn't touch my dick with it. Fuck.

"Mmmm," she says, sucking on the cage. I can't feel a thing.

She backs away. "Can you imagine if the cage wasn't there?"

Damn.

"It's a shame I can't put it inside me," she says smiling. "I'd feel everything and you'd feel nothing."

"Fuck, Emily," I say. "This is some kinky stuff."

"Well, you promised," she says, sweeping her hands down her body. "I daresay you're not coming out of it so badly."

"That's true," I admit, looking her up and down and taking her body in

"Oh," she says, disappointed. "I mean, I hope you will enjoy this. In a memorable way. I ... want to find a kindred. Where we can still be friends but explore a bit. And sometimes to explore, you have to break boundaries down."

Wow. My flatmate, my gorgeous flatmate ... confessing?

"Well, maybe I can return the favour at some stage?" I say

"Mmmm, yes," she says. "Be careful what you wish for. Now, stand up and take some selfies with me."

Fuck.

So it is that I'm nude, in our flat, taking full body selfies with my topless flatmate. Lots of them. With Emily's phone. I'm shaking a little by the end. I trust her, but it's a ... crazy, crazy risk. Stupid, really. And ... well, and I might not get my dick unlocked for a while.

"Now, here's the next thing I've been thinking about," Emily says archly, sitting back down. "The guy downstairs has kind of been staring at me for a while. He's nice. We had coffee a week ago. I'm going to message him with an offer. He'll come here, knowing full well what's going on. We'll roll a die. If it's even, I suck him off. If it's odd, you do. He'll know this. And he'll come up here or he won't."

My jaw drops. I can't speak. Fuck.

But I can't move. I ... shit ... I want this. I suddenly realise that I'm enjoying, no, loving being at her beck and call. Fuck.

She messages Jack downstairs, opens the front door slightly.

She sits back and sips her vodka. I sit on the sofa, my dick dripping precum onto our throw.

There are footsteps on the stairs and a guy pokes his head around the door. He's in a towel. He's about six foot, sandy-haired and well built. He grins and walks through, closing the door behind him, admiring Emily, then turning and looking at me.

"Hey guys," he says. "I'm Jack."

Emily smiles. "Tell me what my message said."

He looks down at the table and pours himself a vodka, drinking it down. "We roll one die. If it's even, you blow me. If it's odd, he does."

He looks around again and sees the leaking cage on my dick. "Damn dude," he says. "Did you lose?"

I shrug. "Jury's out."

"Jack," Emily says. "Any chance you want to ... extend the bet?"

He raises an eyebrow. "Keep talking."

"Drop the towel, then on top of the first bet, we roll four times. The first determines Ben or me. The second determines how many secrets that person admits first. The third, for odd, you get bound up, for even, I lose the knickers. The fourth, if it's one to two, you're in charge for an hour, three to four, it's me, five to six, it's Ben."

"In ... charge?" He says

"In charge," she says. "And you can do whatever you like, Ben and I will do what you like. Ben, that all ok with you?"

I nod and look at Jack.

His eyes light up and he nods greedily, dropping the towel. He's nude underneath and his dick is already a bit hard. "We'll do the first three first," she says, and he nods again. She rolls. It spins. It's a one. Fuck. Emily grins, Jack looks disappointed. She rolls again. It's another one. Fuck. I hope it's not weighted. Again. A three.

"I get off on girls wearing lycra," I blurt, and Emily giggles. Then, before I get scared, I drop down onto my knees in front of him and take his cock in my mouth.

I'm straight ... or at least I'd considered myself straight until now. I'm drunk and feeling a bit adventurous. It's ... weird. Sucking his dick is like ... well, like I'd thought it would be -- fleshy and hard, and warm. I try to not think about it too much and concentrate on what I'd like to feel; I wank him off and lick my tongue around the top of his dick. He moans with pleasure, and I carry on as he hardens fully in my mouth.

Shit. I'm sucking a man off. I keep going. Round the top and up and down the shaft. Then ... fuck ... his dick hardens and spurts warm jizz into my mouth. I almost recoil instinctively, but try to embrace the experience. Fuck. Do I swallow or spit?

His dick twitches and I inadvertently swallow. It's goopy, kind of lumpy and thick. Salty. Shit. I feel myself about to gag, but swallow again. Fuck.

I pull back, licking his warm, veiny cock as I do.

Shit. I lick my lips and he grins. "Fuck, you're a randy bugger Ben," he says and Emily leans forward. I barely look; I don't want to risk meeting her gaze, although ... it sounds like this is exactly her bag and I'm wondering if it's kind of mine too.

She rolls the die. It spins

Five. She grins and reaches down into her bag, pulling out two pairs of handcuffs. Jack takes them eagerly, his cock still dripping slightly. He sits on the chair, then cuffs his feet together, then his hands, behind his back. He's done this before, clearly.

"Don't worry guys," he says. "I'll be out of these soon as I'm in charge."

Emily leans forward and picks up the die.

She rolls. It spins. It bounces.

Five again.

"DAMN!" Jack swears. Emily grins. I can't believe it.

I smile, lean forward and pour myself a shot of vodka, sipping it slowly. Jack goes pale. Emily flushes.

"Emily," I say. "Pass me the key."

She laughs briefly and slips the cock cage key over to me and I unfasten it, sliding the cage off with some difficulty. It's hard getting it past my balls.

I manage to get it out and it's semi-erect.

Phew. I was worried I couldn't get it out at all.

"I'll be right back," I say. "Emily, by the time I get back, I want those knickers on the floor and you lying down on the sofa."

I go and brush my teeth. Really thoroughly.

Then I come back, finding her nude on the couch; her pussy perfectly shaven, as I expected it to be. She's gorgeous. I take some photos with my phone, for posterity. Some of them are even quite artistic, but my dick is rising.

I find some cable ties and attach Jack's feet firmly to the chair, giggling.

Then I look down at Emily and smile. I try to relax.

"Jack," I say. "Tell me about any sexual interactions you've had with Emily."

"Fuck," he says. "We ... uh ... well, we went for coffee a week or so ago and ended up in my place downstairs. She told me your shower was broken and asked to use mine. The next thing I know, she's walking towards the front door, completely naked, all her clothes in a bag. She looks round and says 'hey, maybe we can get crazy sometime' and then just leaves."

I look down at Emily, and she smiles. "Hey, girl's gotta have fun."

I smile back. "Well now," I say. "Why don't you tell me where your favourite sex toy -- or toys - are."

She looks surprised, then grins.

"Bottom drawer," she says. "Behind my knickers."

I walk slowly into her bedroom and pull out the drawer, finding a few vibrators in there. I take out all the underwear and find a few other things too, scooping them up and taking them with me.

Back in the lounge, I flick the vibrator on and lay it down on her pussy, making her breathe harder. Jack gets hard again and so do I.

"Emily," I say. "Tell me about the best, but most public sex you've ever hard."

Emily pales a little, but her chest is heaving, breasts going up and down as the vibrator does its work. "Shit," she says. "I was drunk. I was at a wedding. I met a guest from another wedding in the same venue and we got on pretty well. The next thing I know, I'm sat at the reception desk while he licks me out. About ten people walked past and assumed I was the receptionist. The chair was pretty wet when I left."

I remove the vibrator. "Turn over," I say, and she rolls around.

I put my dick between her ass cheeks and just let it rest there. Then I get up and pull out the paddle I found in her room and start spanking her.

It makes a great noise, and she winces with every blow.

I keep going until she's a bit red, then get her to turn over, and replace the vibrator.

"Emily," I say. "Tell me about two humiliating fantasies you've had."

She flushes deeply, glancing at Jack.

"Fuck," she says. "You walking in just as I cum. Anyone I know hearing me cum but I still do it even though I know they can hear."

I sit and think about that for a moment and let her think about it too. Jack's mouth is still open.

I wipe the thin paddle down from her chin to between her tits, then down to her pussy where the vibrator sits. With a little swipe, I smack her stomach with it, and remove the vibrator. The couch is warm and has a damp patch.

I climb up between her legs and give her a big lick right up her pussy, tasting my flatmate's juices. She shivers and moans softly. Then I have an idea. I climb off a moment and put my phone just by Jack's shoulder, setting it to record video.

Then I go back and Emily looks at it, and at me. I slip back down between her legs and give her another lick, making her moan out loud. I go again, then lick furiously at her clit for a bit, watching as her chest rises and falls, her eyes closing. After a few moments, I back off and just watch her face as she opens her eyes and looks at me, a mixture of lust and embarrassment there.

I wait for two minutes, then go back down for a bit.

I stop as her breathing deepens and quickens, sitting back up.

This time, she opens her eyes and looks at me with desperation.

"Please," she begs. "Please."

I get off and walk over to her, my crotch roughly level with her face. She ducks her mouth towards it and takes my dick in her mouth, sucking it for a moment, before I back off.

Shit that felt good.

Then I find another vibrator, a bigger one, with a notch for her clit and slide it inside her. I turn it up one notch, gesturing for her to touch it if she wants. I look through her phone contacts and dial a number, using an internet service to guarantee anonymous calling. I call her friend -- or former friend -- Sam, then I pick up my phone, focusing on her face.

There's a moment of pause, then she takes the vibrator in her hand and begins to pleasure herself, her chest heaving, her face flushed. Her breath comes faster, her breasts rising and falling, a glint of moisture on her pussy.

"Hello?" Sam says. "Who is this?"

Then she hears. She doesn't hang up.

"Who is this?" She says again.

If anything, Emily gets louder, breathing and moaning more and more loudly.

"Where are you?" Sam says. "Who are you? And where can I get one of those?"

Emily cums loudly, her body shaking, her face ecstatic, the phone recording every moment, me and Jack naked, hard and watching; our friend listening anonymously on the phone. I hang up the phone.

"Fuck!" Emily says, shaking and laughing. "Fuck! Oh Ben, you have got a wicked imagination!"

Jack swears softly and I grin.

"Come on now," she says. "Let me taste that cock again."

I shake my head. "Well, you've been good ... but not that good. Stay where you are."