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It was just supposed to be a fun night on the town. A final all-out party in memory of our college hero Joshua. He wasn't dying or moving away or anything like that: he was just getting married. But it still felt like this would be our last chance to go wild the way we used to back at the Delta Omega Gamma house.
"Phones in the box boys. Lets make this a bachelor party to remember, and leave no evidence". Darren whispered the last part and gave us a wink. We all chortled and shot eager grins at each other.
If us four were the TMNT, Darren was Raphael. He was always the one getting us into trouble in college - whether it was sneaking into sorority house parties disguised as a pizza deliveryman or getting into the big fights with other fraternities from setting their lawns on fire. He was however notoriously careful to maintain his reputation in the eyes of the college itself, and thanks to his 'No Cameras' policy we'd dodged any real repercussions during our 4 years of countless drunken parties and hungover exams.
"If I made it this far without getting busted on any social media then we sure as hell aren't going to slip up tonight."
Joshua, Travis and myself eagerly threw our phones and smart watches into Darren's fancy briefcase, and he locked it and placed it on the drivers seat of his car. His jet black Porsche Panamera with the vanity plate 'THE-MAN' was somehow classy and trashy at the same time. Textbook Darren.
It was a little after 8pm, and we were in the heart of downtown, heading to the first stop of our evening. We'd planned a pretty classic bar crawl, a few bars for some beers and catching up, then an adults-only escape room called 'Magician's Secret' to get us all revved up for our grand finale: a 2am rave at our favorite night club to try and pull chicks. Joshua vowed to leave after the adult escape room to keep the fiancee happy, but Travis, Darren and I had a plan to get him drunk and at least on the dance floor one last time before we all trudged off into our mid-30s.
"Sorry boys - I can't do shots tonight. Susan and I are meeting a florist tomorrow to look at bouquet options." Joshua almost sounded like he believed himself.
-Three hours later-
"SHOTS SHOTS SHOTSSHOTSSHOTS SHOTS. EVERYBODYYY"
Travis was the tallest of the group and he was pounding his fist on the bar and screaming along with Lil Jon on the speakers as Darren, Joshua and I slammed yet another tequila shot. Travis always had a jittery energy to him that scared the girls away, whereas I was the quiet thoughtful one in the group. I guess that would make Travis Michaelangelo, and as much as I wish I wasn't, I was definitely the nerdy Donatello of the bunch.
The bar was packed and raucous - just the way we liked it.
"Oh shit it's almost midnight. We have got to go if we're going to make our booking!" Darren grabbed the two of us by the scruff of the neck and pushed us through the crowd towards the door. We barged through the crowd of dolled up girls and nervous guys and made it out into the dark, cool night - our ears ringing and the smell of cigarette smoke thick in the air.
Travis was just behind us, coming outside to take a leak up against a wall. After a cigarette in the alley, we all piled into a taxi. Darren sat in the front passenger seat and gave the driver a crisp $100 bill. "Can you take us to this address?"
In minutes we were standing outside a large Victorian looking house. There were no sounds coming from inside, and no lights on. All the windows were dark.
"Are you sure this is the place?" I asked Darren.
"Yeah my colleague said it would look abandoned, but that's just to keep it secret. It was super expensive so I'm guessing their set up is pretty full on inside. He just said it was 'freaky and great for a wild night out'".
The taxi sped away down the quiet street and we walked up the steps to the front of the house.
We knocked on the door and a small window opened.
A pair of blue eyes with long lashes and dark mascara stared right at us. Peeking down through the narrow window I could make out a pair of DD tits sticking out the top of a tight blue latex dress.
"Password."
Darren cleared his throat. "Ahem. Purgatory"
"Participants."
"4."
"Sex."
"Yes please!" Travis called out from the back of the group - before bursting out laughing.
The blue eyes narrowed
Darren shoved him back away from the door.
"4 males."
"Waivers."
Darren pulled 4 paper booklets from his suit pocket, unfolded them and stuck them through the window.
We stood there in silence for a brief moment - exchanging nervous grins as we listened to pages turning and a pen scribbling.
The window closed and after the sounds of a few locks sliding, the metal front door creaked open.
A dark hallway loomed in front of us. The woman was nowhere to be seen. A dark red carpet ran down the center of the hard wood floor, about 30 feet long. At the end of the hallway was a single wooden door with a key sticking out of the lock. Asides from a dim chandelier in the center of the raised ceiling, the hallway was empty. I couldn't see the woman, or a door where she might have left the hallway from. I felt the hair on my arm stand up.
"This is terrific boys - I'm so fucking excited. Lets go in." Josh led the way as we took a few ginger steps down the hallway.
I elbowed Darren in the ribs. "Did you forge our signatures again?" He just shot me his textbook cheeky grin.
As we made it halfway down the hall we heard the metal door behind us slowly creaking shut. We turned to see it finish closing with a gentle 'Click'. I quickly head back to confirm that- "Yep it's locked." I called out to the group.
Travis was already opening the wooden door and we as all piled into the next room we saw it was a circular, carpeted room with three doors: one directly in front of us labeled '3', one to our left labeled '2' and one on our right labeled '4'. It was a well lit room, with a round wooden table in the center of the room. Atop the table was 1 elegant, lit candle. As we closed the door behind us I heard it 'Click'.
We looked around for anything to touch, solve, press. There were no buttons or levers for us to pull.
"This escape room is weird..." Joshua said nervously.
I looked underneath the table - there was a single envelope stuck to the underside. I opened it, and inside was a folded piece of paper and 4 playing cards. I grabbed the letter and read it aloud.
"Welcome to the Magician's Secret. You have purchased our premium midnight package. This grants your group exclusive access to the entire property this evening. The only other people here are the performers that are awaiting your decision. By signing your waivers you have agreed to partake in various sexual acts. These may involve one or multiple partners. These will stretch your limits of what you believe to be possible. On each door is a number that corresponds to your first sexual challenge. Choose carefully, because once you enter there is no going back. At any point, should you wish to terminate the experience - say our safe word to any performer: "Red Red Red." This will lead to all performers concluding their services for the evening, and all participants will be lead to the exit at once."
Joshua looked nervous.
"Whoa guys I was fine with strippers or maybe even a hand job from a hooker but I can't go all the way with anyone - I'm engaged!"
Darren slapped him on the back. "Don't worry man - When I booked this place I told them to give us a room where you can stay loyal to Jessica."
"Her name is Susan."
"I know I know - only teasing!" Darren stuck his tongue out.
I grabbed the four playing cards and placed them on the table face up. Each had a sticker in the middle of the card that looked like it had been printed using a label maker.
'4 of spades - Stripper's Delight'
'3 of clubs- Feet Fantasy'
'2 of diamonds - 5-way Fever'
'Ace of hearts - Futanari Surprise'
We all stared at the cards dumbfounded as our thoughts ran wild.
"Futanari? That's chicks with dicks dude!" Travis chuckled.
We all shot a nervous look at each other. Which unlucky one of us was going to get the woman with something extra?
Before anyone said anything Joshua grabbed the 4 of spades and said, "Have fun deciding boys!" With a cackle he ran up to door number four. It was locked, but after he pressed his playing card to the door next to the keyhole, he unlocked it. He ran through and closed it behind him. 'Click'.
The other three of us looked at each other.
Travis was the first to break the silence.
"I know which one I want." he said with a small nervous laugh.
"No way am I taking the Futanari one. I want the 5-way Fever card." I said, taking a step towards the table. My mind was starting to race with the thought of 5 women surrounding me, using their mouths, their hands their-
"Like hell you're getting it!" Darren grabbed all three cards and held them with both hands. "I paid for the whole night I should get the next choice!"
"Bullshit dude that's not fair at all!" Travis said as he crossed his arms. "This place was your idea - you should have to put up with their freakiest room since you wanted to go to such a kinky place."
Darren bit his lip and looked around the room.
"Fine we'll... I don't know... shuffle them up and deal them out. Happy?"
I had a think about it. I wasn't super into feet but I'd take a foot-job from some bombshell blonde - that wouldn't be bad at all. And I'd never had a 5-way let alone a 4-way before. 2 out of 3 odds of a great evening weren't too bad.
"I'm okay with that," I said. "But I want us all to shuffle them up - so there's no funny business."
We anxiously took turns shuffling the cards. Me first, then Travis. Darren stood still just watching us shuffle. Then Darren shuffled the cards, holding them out face down, fanned out. Travis reached straight for the card closest to him and grabbed it.
"Feet Fantasy. Fuck yeah that's the one I wanted! See ya boys!". He disappeared through door three.
Darren and I were staring at the cards for a brief moment.
"Fine if you're going to take so long to decide..." Darren handed me one and flipped the other over.
As he flipped it over I felt my heart sink.
"5-way Fever! Would you look at that!" He beamed with joy before seeing how depressed I look.
"Hey don't worry man just think of it as having anal sex with a girl. Trannys usually have great tits too. Oh and pleaaase don't use the safe word - I'll... how about this - I'll give you 10 grand if you play ball and let me stay here for our entire two hours. What do you say?"
I shot him a dirty look. Was I really going to do this for him just because he offered me money on top?
"Think of it this way." he continued. "Joshua is probably having the time of his life! He's about to get married - this is his last party! Don't go ruining the mood yeah? It'd be a real bummer for the night. Let's make it 20 grand - and... And I'll help wingman you at the rave! We'll find you a perfect 10 to make it up to you. Promise!"
"I guess..." I grumbled.
"Thanks man you won't regret this!"
I sighed as he sprinted for his door. On the one hand, I knew he was good for the money. 20 grand would go a long way. I also knew he was right - if I ended our session early, the boys would probably hold it against me for years. Back in our college days we'd challenge each other to sleep with the ugliest girl we could find. Guys who didn't play ended up getting kicked out of the frat.
I turned around looking for where door 1 even was. The only door left was the door we first came in through...
Looking at it closely I could see a large A engraved into the wood. Pressing my card to it, I grabbed the handle.
The door swung open to reveal a bright, square room. Where was the dimly lit hallway? Where was the exit to this place? I took a step inside.
As my eyes adjusted to the bright lights, I heard the door 'Click' shut behind me. I appeared to be in some sort of classroom for a medical school. I could see diagrams of different body systems on the wall, a whiteboard on the left side wall, a patient's bed in the centre of the room and a tall cabinet to the side with various bottles and vials perched on top. In the back right corner of the room was a rather curvaceous woman.
She had her back turned to me and was rummaging through a drawer of medical supplies. She was wearing what can only be described as a slutty Halloween nurse outfit, but made out of shiny red and white latex. From her waist down was a red latex skirt that went down to just below her knees, and her top was white. She even had the little nurses hat on her head. Her long blonde hair was tied into a tight bun. She looked to be about 5 foot 10, and was wearing see through stiletto heels.
Without turning around, she said: "You're late for your appointment. Come sit on the bed." She said it sternly - like she was growing impatient or talking to a disruptive child.
Instantly I felt like I was 16 years old again - being ordered around by the school nurse. I approached the bed and sat down.
She finally found what she had been looking for - two long red rubber gloves, which she started pulling onto her hands. They went up to her mid-forearm.
Finally she turned around and faced me. She was wearing pink eyeshadow and dark mascara. She was wearing a facemask that covered her from chin to nose.
Looking down slightly I realised she had some mammoth tits. They were probably the biggest I had ever seen in real life. They must have been a size F or even G - and the latex top she was wearing was awkwardly stretched tight over them, barely able to contain them. Her cleavage was practically squeezed up to her chin. Instantly I felt myself getting an erection. I awkwardly shuffled and lay my hands on top of my lap - trying to hide it. She glanced down momentarily, before letting out a somewhat exasperated sigh and handing me a medical gown.
"Strip. Put this on."
"Wait a minute... miss... what exactly are you going to... do?" My nervous voice sounded so scared to my own ears. Could this woman really be a...
"You chose door 5 right? Medical Mistress? Well here I am - so take your clothes off and we can start."
I almost corrected her before stopping myself. 'There must be some sort of mix up with the escape room performers' I thought to myself. I let out a big sigh of relief and eagerly ripped my skinny jeans and cotton shirt off, before putting the medical gown on.
My drunk brain suggested flirting with her.
"Are you going to do a... penis inspection miss..."
"Shh. Stop talking during the procedure. Make another sound and I'll have to figure out a way to keep you quiet..." She said sternly, as she removed her surgical mask. The corner of her mouth was curled into a smile and she blew me a little kiss. She was wearing ruby red lipstick.
She turned away from me and walked towards the whiteboard at the other side of the room. I watched her generous booty sway from left to right as she walked. All i could think of was grabbing her by her hips from behind...
She selected a red marker and started writing:
-Today's Procedures-
'Instrument A = Blowjob'
'Instrument B = Handjob with fingering'
'Instrument C = Titty fuck'
'Instrument D = Lapdance'
'Instrument E = Sex'
'Instrument F = Anal Sex'
I was about to ask her what these instruments were but stopped myself, remembering her playful threat.
She opened up the cupboard and brought out a large tray of sex toys. Each had a small card next to them with a letter printed.
'A' - a black blindfold
'B' - metal handcuffs
'C' - a small blue butt plug - it looked pretty soft
'D' - a medium red butt plug - it looked like a harder plastic
'E' - string of medium sized anal beads - black and round starting at the size of cherries but ending at the size of tennis balls.
'F' - a large black dildo. About 9 inches long, it had two large balls and veins. It looked like a proper porn-star cock.
'I would love to see her wearing these plugs while I'm fucking her...' I thought to myself...
"What procedure would you like to try first?"
I stared at the toys, looking from the whiteboard to the tray, back and forth.
"Can I talk?"
"Yes."
"How are you going to give me a handjob and finger me if you're wearing handcuffs?"
The nurse paused for a second with a bewildered look on her face before laughing.
"Oh my sweet innocent child! These toys aren't to be used on me, they're for you!"
I gulped. I'd used handcuffs before of course, but I'd never had anything bigger than a pinky finger in my back door before!
I thought about my options. She really was a true babe. I definitely wanted to have sex with her but the anal beads looked way too big and long to fit.
"Lets start with option B."
She nodded and grabbed the handcuffs.
"Lie down on the bed."
I lay down and she raised my left hand above my head. Handcuffing it to the bed's railing above me, she looped the chain around the railing before lifting my right hand, and securing them. I tested the cuffs - they were strong. I wasn't going anywhere.
She slowly walked to the light-switch and dimmed the lights. She pulled out a remote control from the drawer and pressed a button. Some gentle R&B music started playing. Then she strolled to the cabinet and selected a medium-sized glass bottle. Pulling the cork from the top, she poured some liquid into her gloved hands, before reaching walking over, reaching under my medical gown and beginning to stroke my cock.
I felt my heart catch and my breath began to race as she slowly pumped back and forth. My erection hardened fully as she rocked her hands back and forth in time with my slowly accelerating heart beat. She stared right in my eyes and smiled as I let out a small moan.
"Good boy..." she purred as she continued to pump my shaft. She moved her left hand to my glans and started gently rubbing the top of my helmet around in gentle circles.
I gently closed my eyes but opened them sharply when I felt her gloved index finger working it's way down my taint towards my ass. She leaned down towards me and kissed me on the cheek.
"This is my favourite part..." she whispered in my ear.
The lube was so slippery as her finger dove straight into me, and she started jerking me a little bit faster. I felt her brush against a nerve deep inside me and a spasm of pleasure ripped through me. God it felt good.
My small moans started to increase in frequency as she was squeezing my penis tighter and pumping faster. Her index finger slid further in as I felt the rest of her hand up against me. I felt my hips rocking back and forth against her, craving more of that delicious feeling from her finger inside me.
But then,
She stopped.
Both her hands retreated and she slowly stood up straight.
I felt myself emerge from the fog of pleasure and I looked to her.
"Can't... can't you keep going?"
"We can continue, but it's time for you to pick your next procedure." She said sternly.
"Okay..." I tried to look at the whiteboard but it was difficult from lying back on my back and with my hands still cuffed.
I took one look at her full overflowing cleavage... I imagined her large breasts on either side of my cock pumping up and down.
"Procedure C"
She smiled.
"Excellent choice..."
She grabbed the small blue butt plug from the tray and poured lube onto it. It was about 5 inches long and just under 1.5 inches wide.
"Raise your legs for me please."
I lifted my legs up and she sat on the end of the bed, pulling my legs down onto each of her shoulders. I felt quiet exposed with her so close to my genitals-
Before I could prepare myself I felt the tip of the butt plug against my asshole.
She stared right down at me. I looked up at her. With her other hand, she grabbed the straps of her top and started sliding them down her arms one at a time. I felt my breath escape my lungs as her full, heavy breasts came fully into view. Her nipples were perky and pointed - she was clearly enjoying this as much as I was.
As a smile crept across my face she said "They're lovely aren't they..."
"Yes they are..."
"Alright now before we go on, it's your turn to pay up."
"What do you m-"
Her smile turned to a mean smirk as she pushed the butt plug firmly - sinking it deep into me. My words turned into a moan of pleasure as she watched the inches vanish inside me. As it almost bottomed out in me, she pulled it back out 4 inches. I felt myself wanting more of it - almost whimpering with sadness.
"Do you want more?" she asked, with her head gently tilted to the side.
All I could do is gently nod.
She pushed it more firmly this time - sinking the whole plug up my ass in one movement. I felt my asshole close around the narrow stem of the butt plug. I was surprised it fit without any pain. Repositioning my legs back onto the bed, she climbed on other side of me - straddling my legs. My hard cock pressed upwards towards her face and she quickly kissed the tip before pulling her face away. My cock moved, small jerking motions trying to get more of her touch. I tried to grab her with my hands but the cuffs held my arms tight. She giggled.
"You're so desperate for more... maybe we'll be ticking more off our list tonight after all..."
I felt my mind race.
"I never want tonight to end..." I said to her.
She chuckled. "You have some big things in store for you... just relax..." she whispered as she placed my cock between her hefty breasts and started pumping. I felt my eyes roll into the back of my head. Her soft flesh combined with the pressure against my prostate was giving me new, rolling, electric sensations of pleasure.
I closed my eyes and sank into bliss.
Seeing my eyes were closed, she pulled one hand away from her breasts, reaching down to...
adjust her painfully tight skirt.
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