Multiples

Dear Reader,

When I wrote Multiples, I didn't have any intention of writing a second chapter in the story. It was just supposed to be a warm up story to get me back into writing another series. I've gone back and read Multiples multiple times now and another story idea came to me. Still, I put off writing this second chapter because I was busy writing for a much longer series. Eventually I hit more writer's block again and took up writing the second chapter for Multiples. If it worked the first time, why wouldn't it work again?

Before reading chapter 2, I strongly advise you to read chapter 1 because this chapter relies heavily on the events from the first chapter.

Your comments, good or critical, are appreciated.

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Multiples Chapter 02

Sam stared at her work computer screen, re-reading the email from her boss, Mr. Ellick, for a third time.

Sam,

Before you leave today, please see me. No rush.

Thomas Ellick

Senior Director of Advertising

ADvantage Promotion Firm

555-555-6505

His signature was longer than the actual email. It had been a month since Sam's boss had arranged to have one of her fantasies come true. At one of his sex parties, Tom arranged for five men to fuck her and she still didn't know who the men were. That was the point. She had just wanted her pussy used and cummed in without knowing who was fucking her. Tom had added a blind fold to the experience and that only made the whole scene so much better.

At 6:00, Will strolled into her office.

"Hey, you have that file for me?" he asked. This was code for, "Want to fuck?" She and Will had been fuck buddies for almost seven months now. Planning to have sex and having sex were some of the few times they were civil to one another. Other than that, the two generally found each other intolerable. To avoid office gossip, they kept their fuck buddy status secret, not that that had kept Tom from finding out.

"Not yet. I'll have it by tomorrow." Sam rarely turned Will down for a roll in the sack, but she was very curious as to what her boss wanted.

Will was clearly not used to being rejected, and asked, "What's the hold up?"

"Mr. Ellick assigned me another task," Sam said, while casually turning her laptop around for Will to read the email.

He read the short email in just a few seconds, raised his eyebrows, gave his signature smirk, and said, "Well, if that's the case, I'll wait until tomorrow for that file. But I am really going to need it by tomorrow."

Sam could only assume that was Will's code for, "I'll really want to fuck AND I want to know all the details about your meeting with the boss."

"I'll have it tomorrow. Right now, I have a meeting with the boss." Sam took great pleasure in smirking right back at Will.

***

"Ah, Sam, please come in. Shut the door behind you."

"Hello, Mr. Ellick."

"Call me Tom, please."

The last time Sam had called Mr. Ellick Tom was at his sex party where no one was allowed to use last names.

"Tom it is. How can I help you?"

"Have you had dinner yet?"

Sam raised her eyebrows and tilted her head in question.

"I have something to ask you, but I would prefer not to ask you in the office. Could I take you to dinner? How about you meet me at my place in an hour? Could I have your phone please?"

"My phone?" Sam asked dumbly. This was not the conversation she was expecting.

"Yes, so I can enter my name and address as a contact. I hope for your discretion with my personal information."

"Of course, Mr., I mean Tom," Sam nodded as she unlocked her phone and handed it over.

Tom quickly typed in his information and then handed Sam's phone back to her. When Sam looked at her phone, she noticed Tom had sent himself a text, ensuring he had her number.

****

Sam rushed home, took a five minute shower, and touched up her make up. She wasn't sure where this evening was going to lead so she put on a matching lace bra and thong set. With thirty minutes left, she hopped in her car and used her phone's GPS to navigate herself back to Tom's house. She had only been there once last month, but Will had been driving and she had been nervous.

Not that she wasn't nervous now. Sam pulled up to Tom's mansion of a home and noted this time, most of the lights in the many rooms were off. The porch light greeted Sam as she rang the doorbell. In just a few seconds, Tom opened the door.

"Welcome, Sam. I hope you don't mind, but I ordered us dinner to eat here. We both like our discretion."

"Thanks, Tom. Dinner in sounds lovely," Sam nodded while also noticing the giant safe in the corner of the foyer. Tom didn't allow pictures at his sex parties and had everyone lock their phones and other personal effects in the safe before they could enter the party. Everything about Tom's house was one sexy memory after another. It was making her a bit damp between her legs.

Tom brought her to the kitchen where he had a steak meal laid out, complete with glasses of red wine on a tiny table that didn't sit any more than two comfortably.

Sitting down, Sam immediately took a drink of her wine. "This looks great," Sam stated, attempting to hide her nervousness with small talk.

Tom smiled and nodded while taking a drink of wine himself. "Sam, I'm not interested in anything becoming awkward with this conversation so I'd like to cut right to the chase. I hope that's alright with you."

Sam had just put a piece of steak in her mouth so she only nodded in agreement.

"Excellent. Next month is a conference out of state. It's three days long and I'd like for you to come with me. If you want to bring Will too, I'll authorize that as well."

Tom called her all the way out here and served her dinner to ask her to a conference? There was clearly something he wasn't saying.

"You could have asked me about attending this conference at the office."

"True, but I'm not finished yet. You are well aware of my sexual interests. Ever since seeing you last month with those men, I was hoping for a repeat performance."

Sam felt a flush of embarrassment and hid it by taking a drink of wine. Swallowing her wine, Sam said, "You can just invite me to another one of your parties. You don't even need to go through Will this time."

"I have no doubt you will attend another party of mine, but they take a lot to coordinate. Even holding them once a month is too much. Having four in one year is an amazing feat. This conference will allow for some fun times without all the planning."

"With all due respect, Tom, I liked attending your party because you make them safe. I'm not sure I'm interested in engaging in such risky behavior outside of your parties."

"I totally understand this. I attend this conference every year and there is a small group of us with similar sexual interests. By small, I mean no more than six of us counting myself. I am wondering if you wouldn't like a repeat experience with this group of select men."

"Condoms would be required." Sam was sad to make that a requirement, but she really liked being disease free.

"If I could prove to you all the men are disease free, would this still be a requirement?"

"How would you do that?"

"These men are like me in that we all have very active sex lives and host parties. We have very similar rules about keeping safe and disease free. I'm usually tested once a month."

"This idea is sounding more appealing to me, Tom."

Tom stands up, and walks behind Sam. He rests his hands on her shoulders and says, "Picture this with me. We're in a conference room, men sitting around the table, talking business. I slowly undress you in front of them," Tom leans in and whispers the next line in Sam's ear causing her to shiver. "The men all admire this beautiful body of yours as you get them hard." Tom began unbuttoning the front of her blouse slowly.

Once Sam's blouse is completely unbuttoned, Tom slides his hands over her lace covered breasts, fondling them, lifting them. "Now imagine all these men going out of their way to touch you, finger you, suck on your nipples." Tom slides Sam's blouse down, freeing her arms from the sleeves, and tossing the material on the floor. He slides Sam's hair over one shoulder and begins kissing the side of her neck while unclasping her bra.

In her ear, Tom continues by saying, "Imagine all these men working to give you orgasm after orgasm until you don't think you can take it anymore."

Sam couldn't take the slow teasing any more. She stood up abruptly, forcing Tom to take a step back. Tom turned her around and pulled her into an embrace. They kissed, their tongues entwining. Sam unbuttoned Tom's shirt and quickly pulled it down. Running her hands over Tom's chest, she admired how well this man in his 50s has maintained himself.

Tom unzipped Sam's skirt and slid it over her hips until it puddled around her feet. He moved his hands over her exposed ass cheeks, grabbing handfuls of flesh while pulling her pelvis towards his hard cock.

"You have no idea how badly I want to push my hard cock into your tight pussy."

Sam moans and says, "Please."

Tom pulls Sam by the hand out of the kitchen. She leaves her blouse, skirt, and bra on the floor next to the table full of a mostly unfinished dinner. Guess a good romp in bed just couldn't wait, Sam mused to herself.

The couple struggled to make it to the bedroom. Tom kept pushing Sam against walls to kiss her and run his hands all over. Sam worked at Tom's belt, pulling it out and leaving it on the stairs. He tugged her thong off and left it on the stairs, just a few steps above his belt.

At the top of the stairs, Sam pulls the button to Tom's pants so hard, it popped off and flew somewhere unseen. In short order, Tom kicked off his socks and shoes. He left his pants and boxers at the top of the stairs. They make their way to the bedroom at the end of the stairs, where Sam had her last sexual encounter with Tom and five unknown men.

Before she knew it, Sam is on her back and her boss is between her legs licking away at one his favorite treats. Sam has no complaints as Tom definitely seems to know his way around. He slides his tongue up and down her folds, circles it around her clit, and then wraps his lips around Sam's clit and sucks hard.

Lifting his head, lips glistening with Sam's wetness, Tom says, "I can just imagine you now, sprawled out naked on the conference room table as a man delves between your legs, lapping up your wetness. Your back arching, breasts thrusting out for the viewing pleasure of every man around that table."

Sam was so turned on by Tom's description of what she could experience at this conference. When Tom helped her fulfill her first fantasy, she didn't want to see who was pounding into her pussy. But now, a new fantasy was forming. One where she could see every man and how aroused they were by her naked, writhing body.

Tom attacked Sam's clit with his lips and tongue. He slid two fingers into her and began pumping.

"Fuck," groaned Sam. She was close. The fantasy in her mind took on a life of its own. She pictured a man grabbing her tits while another drove his cock into her. And a third rubbed her clit without mercy. It all became too much and Sam's back arched and her legs shook as her orgasm took over her body. A keening noise ripped from her throat as her orgasm hit its peak.

Slowly, Tom lapped up Sam's juices, relishing every drop. "You're beautiful when you have an orgasm," Tom noted as he licked Sam's wetness from his lips. "I would very much like to give you another one," Tom says as he moves his body between Sam's legs. He holds his cock at her entrance and looks at Sam expectantly.

"Yes." But what Sam really wanted to say was "Fuck, yes, fuck me already."

With a smile that quickly turned into a groan, Tom pushed into Sam.

"Fuck, yes," moans Sam. Her overly sensitive entrance quivered around Tom's cock.

"Rub your clit for me. Work yourself back up so I can watch you have another orgasm," Tom ordered.

Sam slowly circles her finger around her clit, letting her orgasm build. Tom pumps in and out of her, watching her face intently.

"We're going to have such a good time at the conference. Your body will be used by man after man. You'll be passed around and made to take cock after cock. There will be strangers' hands all over your body."

Fuck that was so hot. Sam loved the idea of strangers feeling her, groping her, fingering her, fucking her. She wanted to be used like that.

"Rub your clit harder," Tom commanded. "I want to feel your pussy squeezing my cock."

Her breasts jiggled up and down with Tom's every thrust. Another orgasm quickly took over her body, squeezing her pussy around Tom's cock. Tom groaned and Sam felt his seed filling her.

Tom rolled off Sam and pulled her close. This was a unique feeling, thought Sam. She and Will were fuck and done, no cuddling, ever. Sam allowed her body to relax into Tom's embrace.

"That was wonderful," sighs Tom. "You're beautiful. Please say yes. Just imagine a group of men using your body, bringing you to orgasm after orgasm."

Sam was ready to agree, but wanted to talk about it. "Would multiple men use me at the same time?"

Tom shifted so his weight rested on his elbow. He looked down at her and responded, "Many of these men are dominant. They'll pull your hair, shove their cocks down your throat, use your ass..." Tom let the last part trail off a bit.

"As in anal?"

"Yes. Do you like anal?"

"I've never minded it. It's just been awhile. Not since college."

"How about DP?"

Sam looked away. She'd seen porn with DP, but never tried it herself. She always wanted to do that, but she needed two guys she could trust.

"Is that a no?" inquired Tom.

"Not exactly. I've never done it before. I'm not opposed to it, but not comfortable with the idea of a business conference with a group of men I don't know trying DP on me for the first time."

"That makes sense. Would you like to try it now?" Tom asked as he stood up. His softening dick bounced between his legs.

"Now?"

"Well, not right this minute, but tonight," Tom clarified. He walked into the bathroom and returned with a prescription pill bottle in hand.

Sam raised her eyebrow, looking carefully at the bottle in Tom's hand.

"Viagra," Tom explained. "I'm not as young as I used to be."

"Um..." Sam felt very confused.

"Will texted me earlier. It seems my invitation to you interrupted his plans for the evening."

Sam laughed and responded, "I'm sure he's cranky about it."

"Let's fix that," Tom replied while popping a blue bill into his mouth. "You know me. You know Will. I'd like to think we're a pretty trustworthy pair. How would you feel about your first DP experience being with Will and me?"

Sam didn't even have to think about it. "Yeah, that sounds good."

"Excellent. Why don't you text Will and invite him over. Then join me in the shower."

Streaking through the house naked, Sam found her purse. She quickly pulled out her phone and opened the app to text Will.

Sam: Come to Tom's place. Need two cocks tonight.

Will: My cock isn't enough for you?

Sam: Don't be an asshole or you don't get to use mine.

Will: You want my cock in your ass...as in DP?

Sam: Are you coming or not?

Will: I'll be there in 45 min.

Sam flew back up the stairs and quickly got in the shower with Tom. He embraced her and began making out with her. His hands roamed her body.

"I assume Will said yes," Tom whispers into her ear.

"Said he'll be here in 45 minutes." Sam could barely get the words out. Tom was pinching and twisting her nipples.

"So do I get your pussy or that tight ass of yours?"

"When I go to the conference with you and a guy wants DP, I want you to take my ass then."

Tom pulls back from kissing her and gives Sam a questioning look.

"Will's already pouty and has never had my ass. I'll give him my ass tonight to humor his ego. But at the conference, I want you to run things. You know, make sure things don't get out of hand. When a guy wants DP, then I want you to take my ass. I had so much fun last time and that was in large part thanks to you."

Tom smiles and says, "I can't wait for this conference."

"I'm excited for it, but really nervous."

"No need to be nervous. I won't let you out of my sight."

"Such a voyeur," chided Sam.

"Hey, this voyeur knows how to show you a good time."

Sam smiles at Tom and finishes washing up.

***

"Hey babe," smirked Will. "You're already naked for me." Will reached out and tugged Sam's towel so it fell to her feet. She stepped back quickly so her naked body wasn't on display for the whole neighborhood.

"Dammit, Will. You can be such an asshole."

Will stepped through the door with a grin on his face. "But babe, I more than make up for it in bed." He grabbed Sam, spun her around, grinding his cock into her ass.

Sam was already excited and couldn't help pushing back on Will's quickly hardening member.

"Fuck, babe, Tom's really got you horny."

"Good to know I've still got it," quipped Tom as he made his way into the foyer area. "And Will, shut the damn door. I value my privacy."

"Yes sir, Mr. Ellick, right away, sir."

Tom shook his head, but said nothing.

Sam approached Tom and wrapped her arms around him. Tom wore only a pair of light shorts and Sam took a moment to appreciate how physically fit he was. Tom turned and wrapped Sam up in a hug, taking a moment to kiss her deeply.

"Are you ready for what's next?" he whispered into her ear. Grabbing her hips, he pulls her pelvis forward and ground his hard cock into her. "I can't wait to fill your pussy again while Will takes your ass. You're going to feel so full."

Sam gave an involuntary shiver. She couldn't wait either.

Will moved behind Sam and grasped her sides. In her other ear, he whispered, "You're really going to let me fill that tight ass of yours?"

"Yup, and that's not all," Sam said, turning her head so Will could catch the smirk on the side of her face.

Will kissed her neck and asked, "What do you mean?"

Tom spoke up, "Sam is talking about the conference next month."

"The AD Conference?"

"Yes, that's the one. Thanks to Sam, you get to come too."

Sam knew Will had a big ego and going to a major conference with the boss was stoking it.

"I'm definitely game, but I assume there's more going on than just attending the conference." Will pulled his shirt off and let it drop to his feet.

"Of course," responded Tom. "Let's head into the living room. I have some supplies set out there."

"Are you going to tell me what else I can expect at the conference?" prompted Will.

"You have a one track mind," retorted Tom.

"You're bringing a hot woman with you to this conference. My mind is going down multiple tracks about what could happen."

"It's so much fun withholding information from you," laughed Sam.

"Isn't it though?" agreed Tom. "Sam, kneel on the couch and thrust your hot ass out."

Sam kneeled on the couch, her hands resting on the back, bracing her body.

"So you're really not going to tell me?" complained Will.

"Eventually, but not right now. Right now I'm really intent on this woman's hot ass. One, if I'm not mistaken, you'll be using soon."

Tom slid his hands over Sam's breasts, dragged them over her flat stomach and moved his fingers through her wet folds.

"That feels so good," moaned Sam.

Tom kissed the side of Sam's neck. In her ear, he says, "Trust me, okay? I'm going to make anal easier and more pleasurable."

Sam nodded. She felt herself dripping, her arousal reaching a new high.

"Ahh, cold," gasped Sam. Tom rubbed lube into her asshole. She sucked in her breath and moaned as Tom's finger worked its way up her ass.

"Just relax and breathe deeply," soothed Tom.