Sexual Escape Room

Summary: Girl discovers herself during wild Halloween sex contest.

Note 1: This is a Halloween 2021 Contest Story so please vote.

Note 2: Thanks to Tex Beethoven for doing double duty by not only editing this story, but by providing the pictures as well.

"You fucking asshole," I wailed, tears streaming down my face. I'd let myself into my boyfriend's frat house room, only to discover him fucking some Asian skank dressed in a slutty witch's costume. It wasn't your typical witch in a black dress and pointy hat, but more like lingerie forged from some kind of prickly black armour, and it didn't even cover her essentials. My unimaginative boyfriend was... not surprisingly... just plain naked.

Since it was about 6:00 PM on Halloween, I too was in costume... dressed as a scarecrow... and not looking at all slutty... not like I'd look later on this evening... but I'm getting ahead of myself... although my denim short shorts did showcase my tight ass pretty damn well.

"Anna, I can explain," Jay blurted idiotically, even though he was caught in the act.

"You can explain why you're fucking another girl?" I demanded incredulously, wiping an instant flood of tears from my eyes and my cheeks.

"Yes, because he's fucking me in the ass, which in this case is perfectly reasonable," the slut replied on Jay's behalf.

"Miranda?! What's that nonsense you're spouting?" I asked, recognizing her voice... she was one of my sorority sisters, but not... obviously... one of my close friends.

"You won't allow him to fuck your ass," Miranda said. "So strictly speaking, he's not really cheating if he fucks someone else's instead. In this case, mine."

"You slut!" I snapped, my anger redirected from my boyfriend to the coed.

"Whatever you say, prude," Miranda snapped back, as she resumed bouncing back on my boyfriend's dick.

"Are you still fucking her?" I demanded, stunned by the audacity of these two assholes.

"Sorry about that," he kind of apologized, but made no attempt to pull out.

"Yeah, you look really fucking sorry," I snapped, and I turned around and stormed out.

"Maybe if you dressed like a woman instead of a twelve-year-old," Miranda called tauntingly after me.

"Fuck you both, and the ironsmith who does your wardrobe," I called back, needing to get the last word in, as if it mattered.

As I wiped some more tears from my face, I went outside, and was walking past a cute red-headed guy handing out flyers, and he addressed me, saying, "Hey, babe! You should come by the ΣΑΕ [Sigma Alpha Epsilon] fraternity tonight for our Escape Room competition."

"What's that?" I asked, trying to compose myself, so I could show him some courtesy. The distressing scene I'd just experienced wasn't his fault.

"We're awarding five grand to the winner. You'll need to win your way through four escape rooms and finish sooner than all the other girls," he explained.

"I just have to puzzle my way through whatever challenges are inside four escape rooms before anyone else, and I win five grand?" I asked. I was great at puzzles, and had done well in a few escape rooms with my ex-boyfriend. (Well, he was my ex now! If that slut Miranda wanted him, she could have him, for all I cared!)

"Exactly," he said.

"Where's it being held?" I asked.

"My frat, ΣΑΕ, is running it inside the Frank mansion," he said. "It's on the market, so it doesn't have any furnishings except for the furniture, Halloween decorations and... other stuff... we've brought in for the event."

"Really?" I said. " That sounds like lots of fun!" thinking I could prove my worth to my ex-fucker by winning this event, which was being held by his own fraternity!

"When does it start?" I asked.

"Thirty minutes from now," he said, after checking the time on his phone.

"I'm in," I said.

"Great!" he said. "I'll call to confirm there's still a slot open for you."

"Do that," I said.

He made a call and asked, "Is there room for one more? Excellent." He turned back to me and asked, name?"

"Anna Blair," I said.

"Jay's Anna?" he gawped. As it happened, I'd just left the ΣΑΕ frat house; since as I mentioned, Jay was a member, so he lived there.

"I'm not that asshole's anything," I said tersely. "At least not anymore."

"What did that dumb ass do?"

"Someone else's ass," I retorted.

"He's an idiot," he announced, undressing me with his eyes. And even if I'm saying so myself, I have some curves worth admiring. Not extreme ones mind you, but nice, nevertheless.

"Tell me about it," I said, appreciating someone joining my side without even being asked.

"Well, head over there right away to get into your first costume," he said.

"Costume?" I asked. "And more than one of them?"

"Yeah, you need to wear a different sexy costume in each room," he said. "ΣΑΕ will provide them for you before you enter each one."

"I do? And you will?"

"Yeah, is that a problem?"

In truth it was... since I always preferred knowing beforehand what was going to happen... I relied upon structure. And since he'd specified 'sexy', it didn't sound like I'd have any choice about how much skin I'd be showing. But with that anal bitch Miranda calling me a prude only a few minutes ago lingering in my head, I replied with false confidence, "No problem at all."

"Great," he said. "And I'll be rooting for you."

In a moment of rare spontaneity, I leaned forward, planted a kiss on him, and even squeezed his dick, which was hard, and said, "You'd better be rooting for me, hot stuff."

"Shit," he groaned. "Now I'll really be cheering you on!"

"Nice cock," I said, before sauntering away with a rush of adrenaline coursing through me. Now to be clear, I wasn't really all that prudish... since I prided myself on my cock sucking abilities... and I was pretty wild in bed, especially after a drink or two or three (or seven)... I just wasn't interested in anal sex. It wasn't sanitary, and it wasn't natural. But I could suck... I could fuck... I swallowed... I was happy to take facials. I actually loved sucking cock! And Jay had never even implied he actually needed anal sex. Sure, he'd asked a time or two... casually, I'd thought... but that was it. So fuck him... I mean never again... at least no more fuck him... but I was going to prove I was no fucking prude by fucking some frat boy right after I won this competition. Maybe even the guy I'd just met. I realized I didn't even know his name, but that could be addressed later on, since he'd indicated he'd be watching me in action.

I walked the few minutes in the fresh air, my head spinning from two very different out of the blue moments.

My anger over my boyfriend of six months cheating on me with a fellow sorority sister pissed me off, and yet this sudden serendipitous chance to compete in an escape room competition, and meeting a cute frat boy, had calmed my anger. But not my determination to turn this sexy lark into revenge!

I reached the location, determined to win. Two good looking frat boys were standing at a table just outside the front door to greet people. I smiled at them, "Hey, sexy."

"Me or him?" the tall blond asked.

"Both of you," I smiled flirtatiously, feeling a strange sense of female empowerment that I couldn't explain.

"Well, I'll take it," the shorter brunette guy said.

"Are you here for the Escape Room competition?" the blond asked.

"I am," I said. "A last-minute entry."

"Well, you'll be a great addition," the blond said, his tone dripping with plenty of flirtation of his own.

"Oh, that I will," I agreed.

"Single?" the blond asked.

"As of twenty-nine minutes ago," I said, checking the time on my phone.

"Who'd let you slip away?" he continued his full-frontal attack.

"One of your own frat brothers," I answered. "Jay."

"That dumb ass," he said, as he walked around the table to me.

"He's a fucking idiot," the other boy added.

"I can't argue with that," I said, appreciating the support.

"We're starting in ten minutes, so if Anna Blair has arrived, shut down out there," a male voice said through a walkie talkie.

"Well, I'd love to stick around and listen to you two tell me how big a fucking asshole my ex is and how fucking hot I am, but I have a contest to win," I said, oozing sex appeal and a sudden confidence.

"Shit, you're a real spitfire," the blond said.

I don't know why I said it, but I did. "You like me now? Then you should see me in bed." I then sauntered into the mansion. A mansion I'd always been curious to go into.

"Jesus," I heard the blond say, assumedly staring at my afore-mentioned tight ass, as I sauntered off.

I walked inside the building, and was surprised to see a very pretty black girl sitting behind a desk, who was gesturing towards a large sign on an easel that said: Disrobe here.

"Am I reading that right?" I asked, my burst of bravado crashing down in a heartbeat.

"Yes, we'll be providing you with a different costume for each room's challenge," the girl said. "And since I'll be accompanying you throughout those rooms, I too will be changing outfits for each one. Although in my case, I'll be wearing a series of sexy outfits, while you'll be in sexy costumes." She then continued, "My name is Jacenta by the way, and I already know you're the lovely Anna. I want you to feel very welcome here."

And I did feel welcome... she was the very epitome of graciousness... even while wearing an extremely sexy outfit... consisting only of a purple teddy (which matched her flamboyant purple hair) and purple stockings. And the teddy did very little to conceal any of her charms, not even her purple bush. Would I be able to look as good in my outfits as she did in hers right now? Oh yes. She was also wearing a very striking pair of matching gold-coloured bracelets; they looked like tiny snakes wrapped a few times around her wrists.

"I'm not sure I can do that," I said, suddenly feeling very hesitant.

"Of course you can," she smiled, rising and walking around the desk to approach me.

"I don't know," I said. It was one thing for me to think I could dress all slutty, but in actuality I'd always dressed rather prim and proper in public... although I did have some sexy lingerie I wore for my man behind closed doors... or rather had worn for my ex-man.

"Oh yeah, you're a sexy thang," she drawled, walking completely around me to check me out from all sides. Fortunately for my self-esteem, she also voiced some approving noises.

"I'm flattered, but I still don't know," I repeated.

"Then why did you sign up?" she asked reasonably.

"It was a spur of the moment decision, right after I walked in on my boyfriend ass fucking a sorority sister of mine," I answered, anger rising inside me again... the image still very much etched in my head.

"That's all the more reason," she said.

"He's a ΣΑΕ frat asshole."

"Then it's time for you to show him... right here tonight... who you really are," she said, all motherly. I mean she couldn't actually be my mother... we weren't even the same race... and she was far too young for the role... but I already knew I liked this girl, and felt I could trust her to be in my corner.

"By winning an escape room challenge?" I asked.

"By winning a sexual escape room challenge," she clarified, as she came so close to me I could feel her breath on my face... an additional thing about her I found pleasant.

"S-s-sexual?" I stammered.

"Yes, each room will contain between one and three sexy challenges," Jacenta explained, then she leaned forward and kissed me.

I was shocked! Here was yet another out of the blue moment! But I hesitated only for a second before I kissed her back. Truth was, I'd been rather bi-curious ever since I started college.... But since I had a boyfriend, I'd ignored that curiosity. But now things were different. So after a moment, I returned the kiss... Jacenta's generous lips feeling so much softer than any boy's. And she was tender... not at all rough. The experience sent a chill down my back.

When she broke the kiss, she urged, "You need to prove to that cheating asshole you're all woman."

"I don't know," I said, still in a daze from the kiss.

"No worries, I've already decided for you," she said. And she started undressing me!

I could have pushed her away.

I could have made some objection.

I could have at least feigned some resistance.

But I didn't.

Instead, I just watched her undress me. It was exciting in a way I couldn't explain, even as I shivered in the sudden gentle breezes wafting against my newly exposed skin.

"Such a tight, ripe body," she purred, as she pulled down my shorts.

"I can't believe I'm allowing you to do this," I said.

"Oh, if we had more time, you'd be allowing me to do a lot more to you," she said, her meaning very, very clear.

"I've never been with a woman," I said, "at all," looking down at Jacenta as she now crouched near my pussy... which was now hidden only by my panties... my nipples so hard.

"Oh, that's going to change very, very soon," she said, pulling my panties down. "And unless you object, I'll be one of the girls helping you to change it."

"I have been curious," I admitted, feeling a little wetness leaking from me. "And even though we met just a few minutes ago, I really like you."

"The feeling's mutual, hot stuff. And mmmm, what a ripe looking..." and then she gave it a quick lick, "...and delicious pussy," she said, staring at it from only a few inches away. "Lots of girls shave down there, but I like the way you just keep your pubes trimmed nice and short. They don't really hide anything, but they still look natural."

"I've never had anyone... boy or girl... say that to me," I said, Jay never willing to go down on me, making me feel very self-conscious by complaining about my pussy's smell and probable taste.

"Frat boys aren't equipped to appreciate the sweet nectar of a pussy," Jacenta purred, as she stood back up and kissed me again... and I detected just the subtlest trace of my own taste on her soft lips.

"No, they certainly don't appear to be," I agreed, trembling both because I was butt naked, and because of her sweet intimacy, that had my legs feeling as weak as overcooked spaghetti.

"Let's get you into your first costume," she said.

"Yeah, I do feel a little underdressed right now," I joked.

"Oh, you'll need to get used to that. It won't be changing much," she smiled, leading me to a closet containing a lone costume on a hanger.

"So I see," I said, unable to tell what the skimpy costume was supposed to be.

"Sit on the chair over there," Jacenta instructed.

I did, still feeling chilly, even though my pussy was burning while I admired this black, sexy girl.

She fetched a package, walked back to me, and handed it over.

I sighed, expressing my instant disappointment, "Pantyhose. I hate pantyhose."

"First, they aren't pantyhose, they're thigh high stockings."

"There's a difference?" I asked, having worn pantyhose exactly twice in my life: once for a wedding and again, obediently, for a funeral. What I remembered most about them was they itched like crazy both times.

"As you can see, they only go up to the thighs," she pointed to her legs. Then as she posed for me, she added, "Second, they look sexy. Don't you think?"

As I gazed at her posing, I had to agree the nylons enhanced her outfit, and especially her legs. "You do look sexy."

"I know," she said, as she sauntered back to me. "And they'll look sexy as fuck on you, too."

"I don't know," I said, as I watched her open the package.

"Trust me," she said, as she took out a stocking and rolled it up in her hands.

I watched as she slid the stocking up my leg.

Once it was on, my pussy tingling as her head was again close to my pussy as she reached for the other stocking. She ordered, "Feel those nylons."

"Okay," I said, moving my hand to the stockings, and was surprised by how soft they were. "Oh my," I said, loving how soft the nylon felt... way different than whatever cheap stuff my mother had bought me for those two dress up occasions.

"I know... right," she said, standing back up. "Now where did I put that other stocking?"

"I mean, I never knew they made nylons that weren't itchy," I said, my hand still caressing the super soft, silky stockings.

"I know! I wear them every day," she said, as she found the other stocking and picked it up.

"I've worn them a total of twice," I said.

"You look so sexy with just a single stocking on," Jacenta complimented, as she sat down beside me to admire it from close up.

She returned to her knees in front of me, and began drawing on my second stocking.

"Aren't they amazing?" she asked, as she finished putting the other one on me.

"To my utter surprise, yes," I said, intrigued by nylons for the first time ever. They were sexy. They were soft. And unlike pantyhose, these were convenient for going to the washroom, or you know... doing something else personal.

As she lingered between my slightly parted legs, she breathed, "God, I'd love to eat you right now."

"I sure wouldn't fight you off," I said, feeling a desire to be intimate with her, just as a buzzer sounded throughout the building.

She sighed as she stood up. "Shoot, I guess it's time to get you to challenge one."

She pulled me up, and I said, still naked except for the stockings, "I still can't believe I'm taking part in this craziness."

She fetched the skimpy outfit and handed it to me.

"You can't? Then I think it's time to bring out the real you," she said.

As I put on the skimpy, revealing outfit, I said, meaning it after the past hour, and some confusing feelings, "I don't even know who that is anymore."

"Then let's go do some exploring together, and we'll see which you we meet," she said, before kissing me again.

"Okay, let's," I agreed, once she broke the kiss.

"We've got to go," she said, taking my hand and leading me out of her reception area and downstairs to a wood-paneled room in the basement. It contained various Halloween decorations, plus a huge, unpainted wooden box in the corner, with a round hole in one side of it. The floor was just a plain concrete slab, with a yellow rug covering part of it.

As we entered, I heard the sound of the door not only latching itself closed behind us, but clearly locking itself closed with a loud thunk. "What was that?" I asked.

"We're locked inside this room until you complete everything you need to do here," Jacenta explained. "Hence the term 'Escape Room'."