Gail
“C’mon, Gail, go out with him! When was the last time you got laid?”
“Terri, stop worrying about me. I’m fine. I get all the dates I want.”
“It’s because you’re fucking your brother, isn’t it?” Added Becky. “Please, just admit it!”
“Eww! For the hundredth time, eww and no!”
Another girls’ night out with another round of overpriced wine, the girls trying to fix Gail up, and Gail denying an incestuous relationship. Gail and her brother Chris had always been very close, which had caused unending speculation amongst their friends that they were, in fact, very, very close.
Terri tried again. “We’re not saying you have to sleep with the guy, but at least go out to dinner. Forget your job, forget us, just go out!”
“Alright, I will. When did you set it up for?”
“Saturday night,” Becky declared.
“I can’t go Saturday. I’m fixing dinner for Chr ….”
“SEE?”
“OK, OK! Saturday night!”
“Good! Here’s his number. His name is Darin and he’s very nice.” Becky winked. “And by nice we mean nice.”
“OK, he’s nice. I’m going. Can we change the subject please?”
“So,” Terri conspired, “Did you ever peek at Chris when you were growing up, you know, when he was looking at porn?”
“UG! Go watch your own brother!”
“I did. He’s not as pretty as yours.”
—————————————————————————————-
Chris
Chris’ friends were glad that he was single and that their wives were so intent on getting him fixed up, because that meant they got to go out without them. If they ever did find Chris a girlfriend, these nights would revert back to couples’ nights.
They were just as convinced as their wives, though, that Chris and his sister Gail had something going on.
“Slim pickings tonight, my friend,” Brad observed. “Sorry.”
“You do realize that I’ve never met anyone here worth meeting, right?” Chris noted.
“You’re too picky,” said Ted. “Just choose one and charm her panties off.”
“I don’t need help from either of you two assholes to find women.”
“Well then pick one,” Brad demanded. “That will get the girls off our backs. You can dump her later and then the three of us can all go out again another night.”
“Unless you’re tapping your sister,” Ted suggested.
“Oh for God’s sake stop that! I am not ‘tapping’ my sister. Or my cousin or my mother or whoever else you and your demented fantasies think I’m tapping.”
“I’d tap her, that’s all I’m saying,” added Brad. “I wouldn’t think any less of you if you were.”
“Because your opinion of me should matter, right?”
“Look, she’s hot and funny and smart. And she’s not married. If you’re not fucking her then why is she still single?” Ted asked.
“Because the only men she meets are perverts like you. Could we change the subject, please? It’s hard to meet women when you keep talking about my sister.”
—————————————————————————————-
The Conspiracy
Becky and Ted, and Terri and Brad were chatting about their favorite subjects.
“Gail isn’t going on a second date with Darin,” started Becky. “And she didn’t cancel dinner with Chris, she just moved it from Saturday to Sunday.”
“Chris talked with a couple girls the other night but didn’t get any numbers,” added Brad.
“Gail and Chris are the most compatible couple between the six of us,” Terri claimed.
“So we all agree that they’re a couple,” stated Ted. “How do we go about proving it? Besides installing cameras in their bedrooms, I mean.”
“Cameras aren’t a bad idea,” mused Becky as she traced her finger along her collar bone.
“Yes, cameras are a bad idea. Let’s focus. We can come up with something.”
They spent the next couple of hours drinking beer and brainstorming. An intervention? No, that would just be an opportunity for more denial. Drug one of them? Right, like any of them would know how to roofie someone.
“How about hookers?” asked Brad. “Maybe a hooker would get him to admit it. People love to confess things to strangers.” The group decided that wouldn’t be reliable. A hooker or gigolo would just tell them what they wanted to hear.
“How about if we actually set them up on a date with each other?” suggested Terri.
“Like they’d go.”
“No, listen. We’re always trying to fix them up, right? We tell them all the time that they need to get some sex, right? How about we treat them to a night of passion in a fancy hotel room. Only they’d be wearing masks, see?”
“Go on,” Becky encouraged.
“We play it like it’s anonymous sex set up by a hookup site.”
Ted wasn’t sure. “What’s to keep them from taking off the masks before anything happens? And what kind of proof can we get?”
“We could watch!” Becky proposed.
“Exactly! We tell them that’s part of the package, maybe we don’t tell them we’d be there, but that a masked audience would be there.”
Brad was enthused. “Let’s do it! I’ve always wanted to see Gail naked anyway!”
Brad did not have sex that night.
—————————————————————————————-
The Setup: Chris
The guys all met at Brad’s house. They handed Chris a beer and an envelope. He questioned the envelope and Brad said to just open it. There was an invitation inside:
“You are invited to an evening of anonymous passionate sex.”
It went on with the date and conditions. The participants and four observers would all be wearing half-masks. All acts would have the consent of both parties. Unmasking would be allowed only at the conclusion and only with mutual consent.
“You’re kidding, right?”
“No, dude, it’s for real!” assured Ted. “We chipped in. We feel bad that we couldn’t get you fixed up, and you won’t pay for sex yourself so we did the next best thing. This place pairs up people who don’t want to bother with ‘dating.’ We got you matched with a bored housewife or executive or someone who liked your picture.”
“My picture?”
“Hey, don’t worry, neck-down only. We got a shot of you at the beach last summer,” clarified Brad.
“Guys, I don’t know about this.”
Brad handed Chris another beer. “What’s to know? Two busy people spend a couple hours together to clear their pipes.”
“Here’s her picture.” Ted handed a neck-down picture of a bikini-clad woman to Chris. “It says she’s 38 and 5 feet 6 inches tall. She looks good, right? You see them tits? Not an ounce of fat where it doesn’t belong.”
“Observers?”
“Well, uh,” Brad stumbled, “Letting people watch takes the cost way down. I mean we have expenses you don’t. So what do you say? At least this way the girls might let us leave you alone.
“All I have to do is show up and have sex with a stranger in front of strangers. What could go wrong? OK, I’m in.”
They clinked beer bottles and Brad glanced at Ted, wondering if the girls had the same luck with Gail.
—————————————————————————————-
The Setup: Gail
The girls met at Becky’s place. Icy cold light beers sat in front of each of them. They handed Gail an envelope. “A present for me?” There was an invitation inside:
“You are invited to an evening of anonymous passionate sex.”
It included a date and the terms and conditions.
“Honestly?”
Becky and Terri explained everything.
“No! Well. No. No I can’t do that.”
“Why not? Here’s his picture.”
“OK, not bad, 36, six-feet even.”
“Not bad?” challenged Becky. “Look at him!”
Terri pointed out his flat stomach. “I think that’s a six pack. Close enough.”
“Broad shoulders.”
“Muscles, but he doesn’t look like he lives at the gym.”
“Too bad we didn’t get a rear view.”
“Yeah, I’ll bet he’s got nice glutes.”
“Dimples?”
“Hmmm ….”
Gail sighed. “I’d tell you two to get a room but it’d rather leave.”
“The point IS,” Terri continued, “you have nothing to lose.”
“Except getting us off your back for a while.”
Gail hesitated. “OK, but, ‘observers’?”
“Um, that’s just how it’s done,” said Becky. “That’s how this sort of thing always works. You should know that, you’re not some school girl.”
“Huh. And if I do this, my dating life gets left alone?”
“Yes! We promise!”
“I suppose I’d have to tell you the details how it went?”
Terri and Becky looked at each other. “Uh, huh.”
“What could go wrong? I’m in.”
—————————————————————————————-
Getting Ready
Becky acted as Mistress of Ceremonies. She was alone in the suite waiting for Terri and Gail. I need to remember to not call them by their names! She was wearing a little black dress with a very flared, very, very short skirt. The top was lacy with a deep V neckline cut down to her belly button. She was braless but not panty-less, having chosen black silky cheeky panties. She had on a pair of black 3-inch spiked sandals which she knew she’d regret later. Her disguise consisted of her mask (pink with feathers on the sides), and a pink bob wig.
—————————————————————
Ted was next door in the boy’s waiting-room. He was wearing a black satin shirt opened to just above the black Spanx that Becky made him wear with his black super-tight trousers. “I don’t care if you’re not comfortable! Suck it up and suck it in!” she had said as she zipped him up. There was no doubt as to his endowment, though. His wife knew what she wanted on display.
Ted heard the door unlock as Brad let himself in. “Shit, did Becky cut your nuts off to get you to fit in those?” Brad had a leather jacket on with a black square-neck tank underneath. His jeans were tight enough to play up his backside.
“Is Terri here?”
“Yeah, she’s next door.”
“I’m getting nervous. This is going to be wild.”
—————————————————————
Becky jumped when Terri opened the door. She placed a hand over her heart. “Damn, woman. You’re going to give me a heart attack!”
“How do I look?” Terri spun around in her red lace romper. It was backless with a halter top. The clinging tight shorts displayed a deep camel toe. Her long, yellow party wig had bangs and pig tails tied off on the sides.
They took turns complimenting each other. “I love your sandals!” Becky added, pointing at Terri’s red 3-inch stilettos.
A knock on the door startled them. Becky peeped and saw a masked woman in the hall. “Just a second!” and then, whispered, “She’s here!” They scurried for their own masks and opened the door.
Gail stared at the women a second. There was no doubt she was in the right place. “HI, I’m ….”
Both women put their fingers to their lips, shushing Gail. Becky handed her a note while Terri texted the boys. “Fox One is here!”
“???”
“Gail is here you idiot. Fox Two should be knocking on your door in fifteen minutes.”
—————————————————————————————-
The Date
“Fox Two” was briefed by written note in the adjoining room, and brought to the suite when the girls were ready. He was wearing a fierce, red and black mask. He was provided with a silver-colored boxer’s hooded robe; he wore nothing underneath.
“Fox One” emerged from the bathroom wearing a red, sheer, floor-length robe. Each of them smiled below their masks as they examined the figure across the room. Becky undid Fox Two’s sash from behind and disposed of his robe. He and his phallus both stood tall. Becky fought the impulse to squeeze a cheek while Terri casually stroked a nipple over her halter top.
Becky approached Fox One, who stopped her with a gesture. Fox One slowly drew out her sash, allowing her robe to flow open. She walked to Fox Two, who lifted her robe from her shoulders and dropped it onto the floor. They pressed their bodies together and inelegantly kissed around their masks as he positioned his cock along her moistened slit. Becky ceremoniously drew back the sheets and the four observers melted into the shadows.
Fox One broke the kiss and took a step back. She placed a hand on his shoulder to keep him in place, and swept it across his chest and around his back as she examined the goods along the way. Once she was behind him, Fox Two gave his hips the tiniest of wiggles, to which Fox One answered with a solid crack across a cheek. Before he could react, she jumped up onto his back, wrapping her arms and legs around him, laughing wildly as she bit at his neck.
Fox Two tried and failed to shake her loose, so he spun their backs to the mattress and plopped his full weight down onto her. That made her lose her grip, which gave him a chance to drive his face between her legs. He barely got in a lick before she crab-walked towards the pillows. He leapt onto the bed and put his knees on her shoulders, pinning her down. He teased her with his cock, keeping it just out of range of her tongue before he finally shoved it into her waiting mouth. She wrapped her lips around him and sucked him the best she could. He pulled out, obviously planning to cum on her face. She tried and failed to get his dick back in her mouth until she freed her arms at the last second. She gave his balls a tug with one hand and pulled his dick back into her mouth with the other, holding him in place until she could make him finish. She pushed him away after his last jet, stuck her coated tongue out between her lips, and made a big show of swallowing.
Fox Two grabbed Fox One by her ankles to pull her flat onto her back. He finger-fucked her as he sucked on a tit for a bit before going for the clit. He spread her at the knees and eagerly attacked her engorged button. She wrapped her legs around his neck so tightly that he could hardly move his head, relying on his tongue and jaw to finish the job. She refused to release him as she bucked her pussy into his face with each climatic wave.
They took time to catch their breaths, lying side by side, stroking each other’s bodies. She was soon ready for more and climbed onto him. She screwed him cowgirl at first until she collapsed onto him, chest-to-chest, and they continued with a slow, rhythmic fuck. Before long, she rolled off and onto her back again and lifted her knees. He re-inserted himself and they gradually picked up speed and force until they climaxed as one. Fox One crashed spread-eagle, gripping the sheets with her fingers and toes, while Fox Two made sure every drop went as deep as he could shoot it.
She rested her head on his shoulder as they caught their breath. She reached between her legs and allowed some of the cum to flow out onto her fingers. She propped herself up on an elbow and made sure he watched as she licked her fingers clean. They kept eye contact as she retrieved another load, which she politely offered to him. He tightened his lips together and shook his head. She made like she was going to eat it herself but suddenly tried to push it into his mouth. She smeared it across his lips, attempting to force it in. He bit at her finger, which allowed her to win. She sat up, laughing triumphantly, as she used the sheet to finish cleaning herself off.
—————————————————————————————-
Becky came out of her daze once she realized that they were done. She stepped away from the wall, leaving Ted wet and cold as she ignored his cum that dribbled down her leg. Brad had spewed twice on Terri’s backside while his fingers and Terri’s had fought the entire time for possession of her pussy.
The rules allowed an unmasking if they both agreed. Becky pointed at their masks and pantomimed removal. They looked at each other and agreed. They removed their own masks and gasped.
—————————————————————————————-
The Aftermath
“Chris?”
“Gail?”
She looked at her brother. “Oh my god what have we done?” She turned to the four observers. “Who are you people? Why did you do this?” She ripped the sheet from the bed to cover herself up.
Chris tore the mask off the nearest man. “Brad? Fuck, Brad?” Chris grabbed him by the lapels and slammed him into the wall. He drew back a fist and threatened, “What the fuck is going on?”
The wives shouted at him to stop and Ted wedged himself between them. “Dude, let him go!” Chris hung on for a second, rapidly glancing at the other man. He dropped his hands and stepped back.
“Ted?”
Ted nodded and removed his mask as their wives removed theirs. Chris dropped to the edge of the bed and covered himself with a pillow. He looked over at his sister, who was shaking in the corner. “Sis, Gail, honest, I did not know. They set us up.” Gail stared wildly at the floor, rocking herself, her eyes welling up; she couldn’t stop trembling. Chris stood and found his robe. “You have two seconds to explain because I am about to make you sorry you were born!”
The four conspirators told them everything. They were sure they were a couple. This was supposed to be a fun revelation, even a celebration.
“Sis, come on, let’s get dressed and get out of here.”
“No. I can’t even look at you. Please, all of you, just leave me alone!” She ran into the bathroom sobbing and slammed the door.
“Do. Not. Bother her,” Chris growled. “Do not go near her or me. Give me the key to the other room.” Brad held it out and Chris snatched it from him. “Gail,” he softly said through the bathroom door. “I’ll…
