Blackmail dare in the Mansion

[Ryann]

Great story! You should write more

[John332]

Amy wasted no time in pointing to Diane and Em and allocating them heads and tails, flipping the coin and revealing it – heads. Em grudgingly nodded and without wasting any more time, quickly reached up the slit of her skirt and pulled her knickers down, stepping out of them and clutching the black, lacy underwear in her hand.

Amy giggled and allocated Steve and myself in the same way and flipped the coin. It was heads again, and Steve flushed. We all stared at him and he quickly pulled off his shoes, glancing nervously at the lift, which was exposing us to new floors every few seconds. Steve hurriedly pulled his trousers and pants down, revealing his long, hairy dick and ass, grabbing Em’s knickers and pulling them on, scowling.

I couldn’t help laughing – it was a comical sight, Steve in women’s underwear. He glared at me and I was suddenly conscious of how much louder I was making it. I quickly shut up and he pulled the knickers on and trousers back up. Em pulled his briefs on very quickly, and Steve laced up his shoes. They both breathed a sigh of relief when they were done – the lift hadn’t stopped and as far as I could see, we’d not been spotted.

Amy giggled and Steve looked embarrassed and angry. We got to the top floor and the lift creaked to a stop. I helped Amy pull the doors open, and we raced along corridors – fortunately, not very far – to a door marked ‘Emergency Exit Only’.

She pulled out another key and opened it, revealing a small, creaky metal flight of stairs. Ushering us up, she locked it behind her and followed us. When we got to the top, there was only one door out, so Diane pushed it open and stepped out onto the roof.

I stepped out, standing on the roof of a tall high-rise building, shingled on top and illuminated by outdoor lighting. We all walked out into the wind, the girls’ hair blowing around and making me shiver. Amy quickly zipped out and again, locked the door behind us. She quickly beckoned us on and we walked around the roof to the other side of the building. You could see for miles, and although there weren’t any other buildings so high as the one we were on, you had a good view of the city streets and buildings. I dimly wondered if anyone could see us – the roof was lit, so it was possible, but probably unlikely.

Amy brought us around to what looked like a disused roof terrace, quickly darting around and locking two glass-fronted doors, long boarded-up with wooden slats.

“Now we should be safe and free,” she said, visibly relaxing. “Welcome to my private – well, sort of – roof terrace.”

We admired it – it was a bit old and 60s, but we waited patiently

“And here’s the dare. Over there, you’ll find a picnic table and a coolbox. Inside the coolbox is a game of truth and dare. Play the game to the end, and you’ll be rewarded with money and photos as you go. I might even join you at some stage. And of course, there is some wine in the coolbox as well.”

She pointed over at the far side of the roof.

“I’ll be here if you need me, but I’d appreciate it if you didn’t interrupt me”
And with that, she walzed off, leaving me feeling a bit surprised – I thought she was going to use this as some kind of public humiliation dare, but on a locked roof terrace, the possibility for intruders was minimal. We wandered around in the direction she was pointing and found a wooden picnic table complete with seats, an outdoor heater (already on), outdoor lights and a cool box. It was all quite out of the wind and actually pretty warm.

I suddenly remembered about Charlotte. Whilst Steve, Diane and Em were checking out the table, heaters and peering into the cool box, I hastily texted her to let her know that we were out of the building with Amy and she could start snooping. There was laughter from my friends, and I quickly finished and joined them.

“Ben, look at this!” Diane pointed. Inside the box was a bottle of champagne, a bottle of white wine, a bottle of decent vodka and a few mixers, as well as a deck of A5 cards and two sealed shoe boxes. “This is going to be fun!”

I thought back to the last time we’d said that, back at the pub by Steve’s cottage and a shiver ran down my spine. It was even worse now that we were being directed by Amy – who knew what we were getting into.

[daremaster 1]

Love it! Just as much as my taco dog. haha.

[123baby]

amazing please keep going

[John332]

Em opened up the deck of cards and an instruction sheet fell out. We all sat around the table and she read it out loud:

“Welcome to truth or dare. This game begins at exactly 8.30pm”

We looked at our watches – it was 8.20, so there was no rush. Em carried on

“This game is ballroom themed, so please imagine that you have just come out to get some air from a smart and elegant ball. For effect, feel free to open the champagne. Similarly, should you wish to add to the theme, there are masquerade masks in the box as well – if you’d like to, please put these on. Other than that, there is no background or rules; take turns to take a card and choose truth or dare. Once you’ve chosen, flip the card over and read it. There are rewards for each one, so take your rewards (in the blue box) as you go. Similarly, if you really don’t want to do a dare, there is an emergency box (red) in the cool box. But be warned! These dares are more extreme, so pass with caution! The first round is a ‘getting to know you’ round, so it’s truth only.”

And that was it. We delved around in the box a bit more and found the masks and the two extra boxes, which we put on the table. Steve expertly poured the champagne, and we sipped.

As our watches went to 8.30, I pulled on a highwayman-style masquerade mask, and Em slipped into a more elegant, sequin-studded mask. We counted down and began precisely on time as if we’d all just sat down.

“How nice to see you all!” Em exclaimed airily. “It’s been so long, but it’s been such a nice ball!”

“Darhling,” Diane drawled in a posh voice. “It’s been fabulous. We must do it again.”

Steve and I agreed, and Diane ‘spotted’ the truth or dare game

“What is this?” She said. “Some kind of game?”

Steve leaned in “Let’s have some fun,” he growled and the girls shrieked in mock-horror

Diane tore open the box and read an abbreviated part of the rules, opening the box with the cards in it. She ‘chose’ truth and read out the card.

“In one or two words, sum up each of the people around you”

She pondered for a while “Well, Ben, you’re very true – to yourself and your friends. Steve, you’re a strong person, and I really respect that. Em, you’re smart and sexy – I wish I could be as sassy as you.”

She looked a bit embarrassed, and I realised that I’d already become so wrapped up in the game that I’d forgotten we were on a deserted rooftop in a rough part of town. I mentally reminded myself to keep my eyes open, but there was a part of me which just wanted to enjoy the night.

“Aw, aren’t you a sweetheart?” Em said.

Was that what she really thought? I wondered. She had a sweeter side than I’d imagined.

Em took the next card and read it out “What is your summer break plan?”

She only hesitated for a few seconds. “I’d like to travel this summer. I want to see Europe and Africa if I can afford it.”

“That would be awesome,” Steve said, and I thought I saw some kind of tacit agreement pass between them

He leaned forward next and read his card. “What do you like most about college / university?”

He sipped his champagne and thought. “Well, I do like my subject, but it’s mostly the life that goes with it. We’re pretty free to do what we want, when we want to. That’s not going to happen again in our lives.”

Everyone was being quite deep and open, and I wondered what I was going to get. I leaned forward and picked up the next card, flipping it over to read “What has been your greatest regret in the last six months?”

I knew what this was, but wasn’t sure what it’d do to our group dynamic. Either way, I had things I needed to say

“What I really regret is not clearing the air with you guys after our last break. We had some disagreements and I held a grudge for a while. I’m sorry for not saying anything but I was pretty mad. But we’re friends, and I really value that. I’d like it if we could all trust each other again.”

Diane took my hand. “Don’t worry babes, we’re not mad at you or each other. It’s all ok – I had a coffee with Steve and Em after our last holiday and we made up. I completely forgot to tell you.”

“Yeah dude,” Steve said. “We treated Diane badly, and it was mostly because of our own inhibitions and prejudices. I think we’re all good now.”

Em nodded and I was relieved. “That’s good,” I said. “I feel better for that. Thanks guys,”

There was a small paper slip underneath the card I’d picked up, which was a handwritten note from Amy. It simply said “Game total: £10 each”

We played on.

[John332]

Diane took the first card next, and declaring a dare, read it out loud
“Kiss the person to your left full on the lips.”

She leant over and gave Steve a quick smacker to his surprise, flicking her eyebrows at him. He grinned back and we laughed. I took the next card and also chose dare.

“Do five pelvic thrusts and your best Elvis impression”

Everyone laughed and I stood up, making it as showy and silly as possible. Whilst everyone else was recovering from fits of laughter, I took a long drink of my champagne and poured out some more. Em took the next card, reading it without really thinking

“If you are wearing a mask, strip down to your underwear. Wait a moment ... what? If you’re not wearing a mask...” she read haltingly. “Strip naked. What the hell? This is round one.”

We were all a bit stunned – it had started off pretty gently. She looked around “What do I do? This is much more extreme.”

Steve spoke up “You don’t have to do it babes. We can leave right now”

Em showed him the card, “I can’t. I want to do this.” I caught a glimpse of it and saw that it had a £75 sign at the bottom – all of ours had had £10.

“You could do a red card,” Diane suggested. “Maybe that’d be better?”

Em thanked her, but then realised “But that could be more extreme.”

She thought for a second and the wind whistled around the top of the building, making us shiver momentarily. She reached into the cool box and took out the red deck of cards, unwrapping them from their plastic and taking the top one. She read it out loud.

“If you are wearing a mask, strip down to your underwear and fasten your hands behind your back with handcuffs. If you’re not wearing a mask, strip naked and use the cuffs.”

Her shoulders sagged and she started to unzip her dress

“I’m really sorry.” Diane offered, looking glum

“It’s ok babe,” Em said, pulling her dress down and stepping out of it. “You weren’t to know, and it was my choice.”

Despite the situation, I couldn’t help but admire Em’s figure again. Her blonde curls bounced as she undressed, and her large boobs were perfect globes, topped with small nipples which snapped out of her bra as she pulled it off. She was looking trim; her stomach perfectly flat. In a fit of pique, she threw her bra behind her. Em sat back down on the seat, rummaging in the cool box for the cuffs, snapping them on and sitting upright on the bench, cool as a cucumber, bound. There was something very classy and very arousing about her poise in this situation, being the only naked one in the group but holding herself well, demure and defiant.

Steve tried to hurry the situation along by taking another card.

“I’m sure as hell not going to take a dare,” he said, and read out the truth. “Tell everyone about your last date.”

Em sighed “That’s miles behind what I did,” she exclaimed sulkily “So unfair,”

“Sorry doll.” Steve offered. “I’ll take my shirt off if it helps?”

Em laughed “Don’t worry about it,”

Steve carried on “Well, it was a really nice date, with a lovely girl.” I wondered if he meant Em. “We went to the cinema, went for drinks and really connected. I think we could be together for a while”

He stopped and had a drink. “Next,” he pronounced, looking at Diane again

[John332]

Diane took a card and chose truth, probably still hesitant after Em’s severe dare

“Tell everyone about your first dare this week,” she said. “If you have performed no dares, strip to your underwear.”

She glanced guiltily at Em and paused. “Well, I went for a run in the woods a few nights ago,” she started, and we all knew what she meant. “And somehow I got dared to give a naked dance around a bonfire for about eight guys and girls, all fully clothed. I’m not sure why I did it, but it was liberating, dancing around like some tribal dancer, the only nude one under the night sky. I left my clothes behind with them and vanished into the dark.”

“So first dares are sometimes extreme?” I offered, thinking out loud. Perhaps Amy was targeting one of us, per night. It’d been Diane on the first night, me on the second, and now perhaps it was Em.

They looked at me strangely, not making the somewhat random connection and I covered up my mistake by taking a card and also choosing truth

“True or false?” It read. “Your pubes are shaved.”

“It’s true,” I admitted. “Smooth as glass.”

Everyone giggled and the tension lightened a little. I took a card for Em and she looked at me, completely exposed, still wearing Steve’s boxers, and with little goosebumps breaking out over her tight body, she chose truth. I flipped it so that she could read it.

“If you are a girl, have you ever had a boob job? If you’re a guy, have you ever done anything to make your dick longer? No,” she said, a glimmer of pride sneaking into her voice. “These are all natural.”

“Steve,” she continued. “Could you see if you could find out whether that last dare was intended? These all seem quite tame in comparison.”

He nodded and walked away from the table for a second, disappearing from view. We waited anxiously, and I poured out the last of the champagne for everyone. I could only imagine how vulnerable she felt, naked in front of her friends on top of a high-rise building. And yet I felt myself being aroused by her vulnerability.

Steve returned, flushed. “Erm ... the dares were correct,” he said. “I found the person who left the set, and they were ... amusing themselves. She wasn't very pleased at being interrupted.”

He took the next card, choosing dare, rather bravely

“Give the person to your right a sexy lapdance.”

He stood up and – somewhat reluctantly – started to sway and bob around Diane. Swivelling his butt into her face, he bent down and touched his toes before rising up and pulling his shirt out, revealing his pecs. He danced around in front of her alluringly, cupping his package under his trousers before sitting back down on the bench.

It’d been a fairly tame round.

[John332]

Round four began with Diane again, and perhaps somewhat ashamed of her previous choice, she read a dare from the card

“In the box are two keys in a blue envelope. Take the small key and unlock the door around the corner with the person opposite you and descend to room 1521. Use the larger key to gain access to room 1521 and follow the instructions on the wall. This dare may take a while, so the other players should continue whilst you are away”

Diane’s voice wavered as she read the dare, but finished it without question. I began to wonder if the whole thing was being orchestrated, and I think the rest of the guys were having the same thoughts.

“I’m not going to take a red card,” she said, looking across at me. “Ben, come with me.”

She stood up and stepped away from the table, adjusting her pink cocktail dress

“We need to be quick,” she said. “If we’re seen, it’s all over.”

I took her lead and stood up to follow her. She stepped towards the door in her ballet shoes, nodding to Em and Steve

“Good luck,” Steve called, and Em echoed him a moment later.

We walked around back to the fire door which we’d come in through – my eyes flitting between the route and Diane’s pert ass, her pink dress clinging to her curves and my eyes picking out the line of her panties underneath her dress. I realised how hot she looked just now, strutting across a rooftop in her dress, about to venture into a rough council block looking utterly conspicuous. I wondered if she was afraid – I knew that I didn’t feel entirely safe, but this was all so odd, it felt a bit unreal.

We got to the fire door and paused. I looked around the corner of the building and spotted someone lying down. Gesturing to Diane, we peeked around and looked closer.

It was Amy; butt naked, lying on a beach towel by a vent, lit by an outdoor light attached to the ventshaft. As we watched, she drew a vibrator up her legs and over her pussy, up her stomach and over her nipples before licking it and looking over at the vent.

We quickly recoiled and opened the fire door as quietly as possible, stepping through and heading down the stairs.

“Diane,” I said. “Something weird is going on, isn’t it?”

[John332]

"Definitely," she said. "Where is everyone in this block? We've not seen a soul. How does Amy have all the the keys? And what was going on with getting Em to strip to her knickers and handcuff herself so early in the game?"

We were only half concentrating, counting the levels against the roof's floor number.

"I wonder if this really is just all about the dares," I thought out loud, briefly mentioning the Lion and Unicorn dare to Diane as we walked down the iron fire escape stairs as quickly but as quietly as possible.

"And there were people watching?" She said, smothering a laugh. "There's got to be something else going on. They must have been paying her to watch - or we've found some kind of sex club again."

I thought for a second "I don't think so - there have been a lot of individual characters here," I said, telling Diane about the artist in the woods "It all seems too disconnected to be one big society"

Diane laughed out loud "You were taken advantage of, weren't you? But it sounds like you had an amazing adventure,"

I nodded a bit shamefully, but before we could think any more, we'd descended to the fifteenth floor and poked our heads around it. Not seeing anyone, we checked the room numbers and quickly found 1521. Listening at the door, the silence almost palpable, Diane put the key in the lock and turned it quietly. It opened, and with only the dim traffic noise in the distance, we moved into the hall of the flat and closed the door behind us.

The flat inside was fairly small, the main door opening directly into the lounge, with a kitchen off to one side and another small corridor with two empty rooms and a bathroom adjoining it. Everything was bare; it was almost completely empty. The threadbare carpet was worn, and there were virtually no furnishings, the walls whitewashed a slightly dirty white, and a battered sofa sat against a wall in the lounge. An analogue clock still ticked on one wall, and a few packages awaited us on the sofa. A white envelope was pinned to the wall - Diane removed the pin and gingerly opened the envelope, extracting another key and a sheet of white notepaper and reading the contents out loud.

"Welcome to your next dare. This is a multi-part dare, but you'll only do as well as your partner in crime allows. First and foremost - check that the clock is working correctly." We did, and it was. Diane continued reading. "The key enclosed opens flat 1376 downstairs. Your partner, if they dare, will race down to the flat, open the door and find the next envelope which is concealed somewhere inside. Be warned - the taps have been leaking down there and the power is out, so you must change into the outfit in package #1."

I moved to the sofa, and whilst she continued reading, opened the package, finding a pair of black speedos inside. Swimwear again, I thought to myself! Knowing that anything could happen, I quickly began to strip off and put on the tight trunks.

"For every minute that they are gone, you must remove one item of clothing," Diane continued. "Once you are naked, if another minute elapses, you must take all of the clothes in the room and throw them out of the window. Then you will return to the roof. If your partner does return in time, then you may open the next envelope and continue the dares. The reward for this dare is £50 a piece."

She looked at me aghast - neither of us particularly wanted to throw some of our best clothes out onto the streets in a particularly grimy suburb.

She continued "You should also know that in the interests of stopping any cheating, I have a webcam concealed in this room which will monitor your progress. You may begin as soon as the second hand of the clock hits 12"

I glanced over at the clock - it was still at the half way mark, so I had a few seconds. Diane looked at me and mouthed 'seven' - presumably how many items of clothing she had on. The adrenaline beginning to pump through my veins, I pulled off my boxers and pulled on the trunks.

"Are we doing this?" I asked

"Definitely," said Diane. "I'm not getting beaten by Em and Steve - but do hurry!"

I agreed

"At least we're not outside in the freezing cold," Diane added, referring to the previous-but one sexual party we'd been to, and raising her eyebrows. "Or eating pet food!"

I nodded my agreement and the second hand approached 12. I raced out of the room

"Good luck!" Diane called behind me, as my feed pounded the light carpet and I headed for the stairs again.

[babygirl13]

Please continue!!! This is the best story on this site by far because of it's clearly well thought out plot and chain of events, and for it's extra kinkiy ways. I especially like it because it has a mystery too it that the characters imply that there might be something more
going on. I like how it's not ALL focused on the direct act of sex like most stories on here. Bravo and well done.

[memnoch55]

I just found this, story, and it is great, can't wait for the next chapter!

[Nick]

This story is honestly one of the best i've read on this site. It is amazingly diverse and has a major mystery element that I have never seen in this type of story before.
A must read!

[lovaboitoy]

I love this story...really hot and creative....

[John332]

Thanks all - your feedback is really encouraging. Glad you like it! Here's the next bit:


I raced down the corridor the opposite way to the emergency access, towards what I hoped were the main stairs. The hall flashed by on either side, and I quickly found another set of stairs leading down. I hurried down the green, cheap carpeted stairs, the metal edge to each step sending a chill through my feet and making me shiver. I ran down them lightly, still straining to hear anything or anyone else in the block, but I was increasingly convinced that the building was deserted.

I ran down two floors, scouring the walls for the sign pointing to apartment numbers, spotting it and running down the corridor, feeling exposed in my Speedos. The lights were flickering here, and the carpet was slightly damp underfoot. I found apartment 1350 and rounded a corner.

This hall was completely dark, lit only by the flickering light from the other part of the building. The carpet was squelchy underfoot, a damp smell reaching my nostrils. I didn’t have time to think about it – I just forced myself on and squinted at the door numbers, finally finding 1376.

Turning the key in the lock, I pulled the door open, a wash of fetid-smelling water flowing out over my feet, making me shiver harder, but I made myself step into the dark hall before I could think about it too much, conscious that the clock upstairs was not about to stop ticking.

I left the door open to allow what little light there was into the flat, and squished through the ankle-deep water, hugging myself to stay warm. I strained my eyes, hunting for an envelope, conscious that it probably wouldn’t be in the water, and examined the walls. The apartment seemed to follow exactly the same layout as the one above, and I quickly checked the kitchen, hurriedly looking through the oven, bread bin and looking on the walls. A tap was dripping steadily into an already-full sink, but I didn’t take the time to turn it off – this was more important.

Sloshing into the main room, which was illuminated dimly by moonlight, I jumped and almost fell over as something brushed past my leg. Looking down, I wasn’t sure if it was a dead animal or something else, but I clamped down on my instinct to get the hell out of this dark, grimy apartment and searched the sofa, table and window ledges.

Still not having found the envelope, I moved into the bathroom where it was almost pitch black. I felt my way around, trying to discern a flash of white – or whatever colour it would be – in the sink, toilet, and ... hold on ... I thought I glimpsed something in the bathtub. Taking care not to knock my shins against anything, I climbed into the bath – and slipped almost straightaway, landing sharply on my ass and ending up in a sitting position in the tub.

The bottom two inches of the bath was filled with some kind of sticky, oily substance which was very slippery and I could feel it squelching underneath me. Gritting my teeth and trying not to think about what I was sitting in, I leaned forward and grabbed the object, which was indeed the envelope in a clear plastic bag.

I carefully extracted myself from the bath and wiped my feet on the carpet, heading out of the flat as quickly as I could. When I got back into the corridor, I accelerated to a jog ... then a sprint, taking the stairs two at a time, running down the hall and breathing hard, barged back into 1521.

[John332]

Skidding to a halt, I pulled myself round the corner to the lounge, trying to get my breath back and heaving a huge sigh of relief that Diane was sat on the sofa.

Legs crossed, she was nude apart from a light pink bra, the curve of her breasts drawing my eyes; I could just see her nipples poking against the lacy fabric. I took a second to admire her smooth, lightly tanned skin and flat belly, her hips curving outwards smoothly and her long, slender legs.

“You had me worried there for a second,” she said calmly, eyebrows raised, gesturing at the clock. It was about fifteen seconds into the penultimate minute. “Another hundred seconds and my dress – and your suit – would be all over this scuzzy neighbourhood.”

“It .... it wasn’t very easy to find ...” I panted. “No light in the apartment, and some ... some kind of trap in the bathroom.”

I looked back down at my legs and ass, which were covered in an oily substance. Handing the envelope to Diane, I headed to the (fortunately functional) bathroom to wash it all off. It wasn’t easy, and I think it was probably cooking oil, given the smell and texture. I dried myself off on a curtain and returned to the lounge, putting my suit back on.

Diane waited impatiently, tapping her finger against the sofa, her legs still crossed. “Ready?” she queried, and I nodded. With a ‘hmpf!’, she opened the Ziploc bag and tore into the envelope

“Congratulations,” she read. “You are now onto part two of the dare. Within package number two, you should find two pens, two notepads, some clothing and a few extras. Please open this package now and distribute the pens and notepads amongst you.”

I ripped the package open and found exactly what the note said. There was another small black package which was also sealed, some monopoly money and a few packets of condoms. Diane continued

“The game will now get interesting. You will each make a sexual wish list for the rest of the week, listing out fantasies which you would like fulfilled in the next few days. Your partner in crime here will do their best to make those fantasies come true, gaining £15 for each fulfilled dare and £30 if they involve another person or are especially risky. You are to dish out the monopoly money enclosed at your discretion but be warned – my penalties for violating rules are very strict.”

Diane grinned at me, rubbing her legs together, drawing my attention back down to her lap, trying to see if I could see her pussy.

“One last thing,” she finished. “This isn’t free. For each wish you list, you must remove an item of clothing. If you become naked, there are additional dares on the other side of this sheet which you can do in exchange for wish credits. List out all of your wishes first and then take the appropriate number of dares – once you’ve looked at the dares, you may not list any more wishes. Btw, shoes and socks count as one item, so no prevaricating!”

I looked at Diane in her bra – she was either going to have to stick to just one wish, or was going to have to get dirty!