Masks That We Wear

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Mister Falcon vaulted up onto his stand and the lights came up in the entryway to show all the waiting masked guests. Brent noted that this week they were allowed to bring dates, girlfriends, spouses, whatever... They all waited expectantly as they looked past Falcon to the girls standing in the darkened suite, illuminated only by their candles. "My Friends!" Falcon said as he opened his arms wide to them. One of the traditions that developed over the years is that of Apple Bobbing, to honor the Roman Goddess of Pomona to wood nymph. When the Roman armies conquered Britain, and began merging their own celebrations with that of the Celts, the apple trees came with them. During the annual celebration, which happened close sot Samhain, the first person to bite into an apple that was floating into the water or hanging from a string, would be the next one allowed to marry."

Falcon smiled at them. "Now, we're not doing marriage here, obviously," he said amid chuckles from the crowd. "But we are doing fucking and lots of it. So, the game tonight is to step up to a bucket bob for your apple to get paired with one of our lovely ladies, and then you get to do to that lady whatever you want to for the next half hour in their designated play rooms either here in the penthouse or the two floors below us. I'll sound the horn to start and stop the half hour so that we can all come back at the same time to do it all again! We should be able to get in three or four rounds tonight." He then gestured to Brent. "Our very own Mister Hill here is getting the honor of going first. So, while he bobs for the first apple, please disperse amongst the three barrels to wait your turn."

Brent gave Falcon a funny look. "Come on, boy," Falcon urged him, "take that suit coat and shirt off and get to bobbing!" He knelt on his pedestal and talked in a low voice to him. "They're not in this group that you're bobbing for. In fact, they're not going to be in any group that you bob in tonight," he said with a smile. "And you will fuck each one... properly this time... or else I'll expose them both to all of my very powerful friends here who will waste no time in fucking them up and fucking them over."

Shucking off his top so that he was bare chested, Brent took a deep breath and plunged his face into the warm water. He hooked the stem of an apple and came back up with it. Dropping it into his hand, he saw that there was a piece of paper superglued to the side of it. Falcon took it from him and held it up for all to see. "Sierra!" he called out. The guests all clapped and a curvy redhead walked forward out of the line of girls. She gave Brent a wan smile as she took him by the hand and led him back to the elevator. Brent couldn't help but look around and saw a strawberry blonde and a brunette watching them. Carla and Mandy. He gave them a brave smile and a nod, which they returned before the doors of the elevator closed in on him and Sierra.

*

After the doors closed Brent and Sierra off from them, Mandy and Carla exchanged looks and smiled to each other in encouragement. "At least it's only four people at the most tonight," Mandy said.

"You mean at the least," Carla corrected in a sideways whisper as the other guests took off their tops and started bobbing for their apples. "Remember, they brought girls with them."

"Two months ago I probably would've had a hang-up about entertaining a girl in such a way," Mandy admitted. She then looked from the bobbers over to Carla and smiled at her again. A real, genuine one this time. "I'm glad that you're with us, Carla. I really am."

Carla smiled and blew her a kiss, that Mandy returned. Then Carla's name was called. And she saw that she had an impressive looking muscular man that could give Jason Momoa a run for his money. Carla strode forward, taking his hand, and leading him off into the penthouse where her designated room was at this evening. Mandy let out a sigh as she waited patiently. Then her name was called a minute later. She walked forward and saw that a relatively average bodied man that was roughly her husband's height with his redheaded wife who was taller than Mandy was, were waiting for her. She gave them a smile as she'd been instructed to, took the man's hand, and led them over to the elevator. They had to wait for it to come back up before they could get in and go down one floor.

Mandy led them to the room that she'd been shown to by the handlers after being cleaned and dolled up. When they got there, she closed the door behind them as her clients looked around. There was a four-post bed with various bondage implements hanging off the wall nearby. On the wall opposite the bed over in the corner was a small stage with a stripper pole on it. A couple of lounge chairs were in the room and there was a small box at the foot of the bed.

"Oh darling!" The redhead in the equally red dress that clung to her body cooed. "They have a sybian!" She exclaimed with joy as she knelt down by it to unpack it and push it to the center of the room. "Oh, do fuck her ass while she pleasures me!"

"But of course, dear." the man said. "Mandy, please?" he gestured to the sybian.

At least they're being polite about it... Mandy thought as she slipped out of her toga and walked naked across the room to them. "What shall I call Master and Mistress tonight?"

"Master and Mistress," the woman said as she put the G-Wave attachment onto the sybian top. That particular attachment had a bulbous dildo that angled forward to catch the forward wall of the vagina, and would fill her pussy up, while the four parallel waves would vibrate and tickle her clit once it was on.

Mandy took Master's offered hand as he helped lower her down onto the sybian. "Ahhh," Mandy gasped, her breath catching as the dildo slid into her and she settled down onto the humped machine. As she did, the horn went off signaling the start of the half hour.

Mistress reached down to Mandy's pussy to spread her labia so that her exposed clit rested right on the wave. She then gave Mandy a smile and held up a finger for her to stay. Mandy waited obediently while both Master and Mistress undressed. Mistress had an impressive body for someone who looked to be in her forties, from the looks of her. Her breasts were nice and pert and Mandy could only hope that she was that perky in the chest when she got to that age. Mistress caught Mandy staring as she hefted her own tits and jiggled them. "You like these, Mandy?" she asked.

"Yes, Mistress," Mandy replied in all honesty. Even if she hadn't unlocked her inner Bi with Carla here lately, she still would've replied that way if only to satisfy the clients. Mistress smiled at her apparent eagerness and leaned forward, bringing her teats to Mandy's lips. Mandy inhaled her scent and submissively looked up at Mistress while placing her mouth over Mistress' left nipple and sucking. Mistress hummed with pleasure and then moved her right tit over for Mandy to suck on.

"God there is nothing more beautiful than watching two women go at it," Master mused as he watched. He was now naked and stroking himself, rubbing lube over his hardening cock. When he was nice and hard, he knelt down behind Mandy and inched forward. Mistress pulled Mandy forward so that her husband could work his cock up her ass. He slid into her easily thanks to the lube and Mandy whimpered and then moaned as his cock nestled up inside of her butt.

After Master was inside of Mandy, Mistress reached down for the control box, turning it on low. Mandy squeaked as the sybian jumped to life, the wave vibrating her clit and the dildo vibrating inside of her. She was coming to love the double penetrated feeling to the point that she'd been asking for it more in bed with Brent and Carla. "Mmmmp... Mmmm..." Mandy moaned, biting her lower lip at the intensity of the vibrating.

"Oh honey," Mistress cooed. "We haven't even gotten to the good settings yet," she said, dialing it up a notch. Mandy arched her back and looked up at Mistress in total helplessness as she felt the dildo inside of her vibrate faster while Master's cock was fucking her ass from behind. Mistress stepped forward, grabbed Mandy's head, and spread her legs before the girl. Her pussy was right at Mandy's mouth. "Come on, baby, show mama what you got."

Mandy's mouth latched onto Mistress' mound and she started pleasuring the older woman with her tongue and her sucking, much to Mistress' delight.

*

Upstairs, Carla was lashed down spread eagled to her bed with 'Jason', as she was calling him in her mind, down between her legs, pleasuring her with his mouth. He was good. Good to the point that she was thrashing around begging him to fuck her as she was constantly brought to the edge before he backed off. He did that twice before the starting horn even went off. Only once the horn sounded did he mount Carla with a flogger in his hand.

"Oh yes, Master, please," Carla breathed, trying to goad him on. He smiled down at her, flogging each of her breasts while simply holding her on the edge with just his massive cock inside of her.

*

When Sierra led Brent into the room, Brent took a moment to look at the various toys, devices, and implements. He wondered if the rooms were the same all over and he wondered what Mandy and Carla were up to. He then looked at Sierra, who was kneeling submissively by the bed. "How shall I please you tonight, Mister Hill?" she asked, reaching up to shuck out of her toga to let it fall to the floor beside her.

He felt bad for having to be here but he resolved to follow his wife's, and his mistress', insistence that he try and enjoy tonight. He was certainly enjoying the view as Sierra was fuller in the breasts and hips than either Mandy or Carla. Sierra had an hourglass shape to her body with proportionate thighs and shapely legs. Brent let out a long, slow breath as he felt his cock stiffen.

Then he reached up and took his mask off so that she could get a good look at his face. She gasped and quickly looked away. He guessed so that it was plausible deniability for her. "Look at me," he commanded her. She meekly turned her head, keeping her face downturned but he could see her peeking up at him. "Take a good long look at my face. My name is Brent. My wife here is Mandy and she is serving just like you are. My... I guess you could call her our mistress or our girlfriend now, Carla, is being forced to serve here too. We're all being blackmailed just like you are and I do not want to force myself upon you." He told her. He spread his hands as if imploring her.

"Why is Master telling me this?" Sierra asked in a near panic.

"Because this is my way of sticking it back to Mister Falcon until I can bring him down." Brent explained. "So, rather than just forcing myself upon you and doing the deed to buy time for me and my wife, I'd much rather enjoy the evening with a willing partner." She looked up at him at that and he smiled at her. "So, Sierra, what is your choice?"

"If..." her voice caught. "If I don't... and Mister Falcon finds out..." she looked up to the corner of the room.

"Brent followed her gaze and saw the security camera there. "He'll find out anyway and punish you for it..." he said, nodding his understanding. He looked back at her. "You still have a choice," he told her. "If you don't want me to touch you, we'll just stay here and talk for the half hour and I'll get the heat off of you onto me. I already did it for one of my employees tonight."

"I'm going to be forced by others regardless tonight," Sierra said bitterly. "You might as well have me too..." her expression softened and she gave him a real smile rather than the plastered one he got from her earlier. "Although, it is nice to have someone with me who's not jumping my bones the moment we're through the door for once." She stood up and walked over to him, taking her own mask off so that he could see her pretty face. "Thank you, Brent," she draped her arms around his neck, pressed her naked breasts to his chest, and kissed him softly on the lips. "I like a knight in shining armor. And... well... It's... it's been awhile since I've made love to anyone. Nowadays it's all business fucking with clients."

"Believe it or not, I know how you feel." Brent told her. He let her control the action and the pace. Before he knew it she was undoing his pants to drop them to the floor. Then she backed him up to the nearest lounge chair and climbed up onto his lap. She dry-humped him while making out with him. When she was ready, she reached underneath to guide his cock into her. They both sighed with pleasure as their bodies meshed together.

Sierra sighed and mewed with pleasure as she slowly rode his cock. They kissed each other passionately and Brent held her bottom as she moved on top of him. Her mews of passion increased as she slid up and down his cock faster and faster. "OH GOD," she moaned, slamming herself down on his cock and shuddering in his arms as he held her close. "Oh my Gooooooddddd..." she let out the long, deep groan as she melted onto his body. Brent held her close, stroking her red hair while feeling her pussy flutter around his cock. He was close but wasn't there yet. It wasn't until after she was coming down off of her climax that she gave him a questioning look. "Did you cum?"

He shook his head. "Not yet."

"Cum inside of me, please," she whispered into his ear, nibbling on his earlobe. "Do what you want to me to do it."

Brent angled her back and had her continue to ride him as he took her ample breasts into his hands and started to suckle on her right one. She gasped in pleasure and squeezed her pussy right around his cock as she continued to fuck him. A few good thrusts later and his cock exploded up into her. "Daaaaammmmnnn..." he breathed as he buried his head into her cleavage and moaned with pleasure.

They spent the rest of the half hour wrapped up naked in each other's arms as they just enjoyed the quiet moment together.

***
CHAPTER 11: Bobbing for Apples - Round Two.

Both Mandy and Carla had a well fucked feeling as they got back into line. Neither of them bothered with their togas and from the looks of the rest of the girls in line, neither did many of the other girls. They exchanged quick notes as to what happened to them. Jason Momoa's doppelganger fucked and flogged Carla to two orgasms in the half hour. Master and Mistress, after getting off with Mandy once, then had Mistress on the sybian with the anal attachment up her ass, leaning back so Mandy could eat her out while Master pounded her from behind.

The redhead that took Brent downstairs, Sierra, got into line with them. She took them both into a big hug and whispered into their ears. "Brent is a good man, make sure you take good care of him tonight when you get home."

"Thanks," Mandy said, hugging her back.

"We will," Carla promised. Sierra gave them both a quick peck on the lips before sliding into line on the other side of Mandy and made a quick adjustment to her mask.

The men all lined up and bobbed for apples again. The three of them noticed that Brent was hanging back, allowing others to go first. "What the hell is he doing?" Sierra asked.

"He's going for pot-luck..." Carla said with a smile. "It looks like her intentionally hanging back to be last, which means he automatically gets whoever is left.

"And it means that he gets less time with whoever he gets stuck with," Mandy said, love bursting in her heart for him.

"That'll work only once," Carla noted, amazed at just how little some acts of defiance can go a long way in making Mister Falcon pissed off.

Mandy's name was called first and her eyes went wide behind her mask as she was paired with a large, muscular black man with a dazzling white smile. With a shaking hand as she could only imagine how well hung he was, she led him off to her room. She caught her husband's amusement as he mouthed 'good luck' to her and gave her a thumbs-up. The couple that had Mandy the first round came up with Sierra's name for this round and Sierra led them away to leave Carla standing relatively alone. A few more men from each barrel came and went until finally Carla was called.

Carla let out a tiny sigh and strode forward to meet a portly looking man and his high maintenance looking platinum blonde wife. She took them by the hand and let them back to her room on this floor, passing Brent in the process who gave her a little wave along the way. When they got to her room, she was immediately directed to lay down on the bed while the blonde slipped out of her dress and mounted Carla. She wasted no time in grabbing a fistful of Carla's hair and starting to make out with her. Carla wrapped her arms around the blonde and kissed her back.

The portly man, stepped out of his shoes and trousers and began stroking himself as he watched the show. Once he was hard, he mounted he shoved his cock into the blonde, who squealed with pleasure. He pumped his cock in and out of her a few times before pulling out and driving it into Carla, who gasped and moaned with pleasure when she was penetrated.

On and on he went, alternating fucking each girl for the entire half hour until they both came and he'd shot his load out over both of their slits while they were pressed together and quivering from their orgasms.

*

With only three girls left, Brent stepped up to the barrel with only one apple left. He simply plucked it out of the water and looked at the name. "Piper?" he asked, showing it to Falcon who had a murderous look on his face for not following the rules and for not bobbing.

"You deliberately held back so you wouldn't have to go first, Mister Hill." Falcon glowered at him after motioning for a short, average-looking co-ed with auburn hair to come up. From the looks of her, she looked like she might still be within her first year or two of college.

"Duh," Brent told him. "You're just now figuring this out?" He smiled at Falcon's anger. "Hey, look at the bright side; Sierra was a really good lay and you can even check your footage to make sure that we did it." He grinned as he allowed the hesitant Piper to take him by the hand to her room. It was obviously still on this floor as they headed away from the elevators.

Once they were closed into her room, she got down onto her knees and stammered out, "H-h-how would Master like me t-to-tonight?"

"You're new, aren't you?" he asked. She looked up at him and gave him a shaky nod. "Relax, I'm not going to hurt you." He then took off his mask and introduced himself, giving her a spiel similar to the one he gave Sierra, and her eyes went wide.

"Oh my god..." she buried her face into her hands. "I-I know who you are Mister..." she nearly blurted out his real last name. "Uh... Mister Hill. Your father's the congressman for our district. You go to my church. She looked up at him fearfully, going stark white. "Please... please don't tell them that I'm here!"

"Shhhh..." Brent went over to her and knelt down, "your secret is safe with me. They don't have to know anything. I will not tell them nor will I use that information against you." he reassured her, putting a hand on her shoulder in comfort. "Like I just said; we don't have to do anything that you don't have to do. You don't have to take off your mask or anything. We can just sit here." he said as the start buzzer went off.

"NononononoNO!" Piper was shaking her head vehemently. "I have to. I got to. He'll punish me and revoke my scholarships. I'll be back out on the streets! I can't afford that! I have to finish my degree!"

"Okay, calm down, relax..." Brent said, trying to soothe her. She huddled into his arms and he rocked her back and forth while stroking her hair.

"I have to fuck you, s-sir..." she whimpered.

"I have your consent, then?" he asked. She hesitated, then nodded. "What would you like me to? How can I pleasure you?"

1...910111213...17