Arrangements Ch. 02

His palms were sweating as he entered the elevator. Michelle's sexual proposal was too good to be true, but his mind had bounced back and forth whether there were negative ramifications to entering into a sexual relationship with his boss. Their car ride down to Tucson had surprising; never had he imagined he'd have his cock in her mouth. Sure, he'd jerked off thinking about it, but he had always been pragmatic, knowing he'd never be able to experience her lips circling his cock, her breast in his hand, his cum sliding down her throat.

Dammit, now my dick is hard again and I have to face her and give her my answer.

Austin descended the 12 floors of the hotel and exited the elevator, subtly adjusting himself prior to the doors opening to camouflage his erection. He considered himself slightly above average in size when soft and hard, and the tip of his cock came a good length down his thigh when fully erect. The problem with trying to hide his erection was his thickness. He'd been told by more than a few women how his thickness stretched their pussy and rubbed that tender spot inside juuuust right. Nevertheless, right now, his thickness was a beacon to everyone that he was horny and needed relief.

He arrived outside the hotel bar at 8:55 p.m. Michelle had dictated he be there at 9 sharp, but he allowed himself a few extra minutes to muster his courage. He wanted Michelle, that was obvious, but again, was it a good idea to fuck your boss?

He spotted Michelle's hair right away; anyone could. Her long, dirty blonde ringlets had a way of drawing attention to her and as he scanned the dimly lit, upscale lounge bar, he noted more than a few business-type guys eyeing her. She exuded sex appeal because she was obviously gorgeous and had an amazing rack, but her blue-green eyes had a hardness to them, letting everyone who looked at her know she was a woman who made quick, sound decisions and always succeeded.

He glanced at his watch, 8:59 p.m., and entered the bar with straight posture and authority. He enjoyed his 6'2" height and athletic build because when he entered a room, a look of slight intimidation usually crossed most guy's faces.

Michelle set her cocktail down and crossed her long, toned legs as he came up behind her.

"Good Evening, Ma'am, may I sit with you?"

The mood in the room immediately shifted as the other men in the room observed Austin speaking to Michelle. Now, they had no chance with this woman.

"Austin, you're prompt. Yes, you may sit in the chair across from me." Michelle gestured to the half-circle back lounge chair across from her.

He unbuttoned his suit coat and sat across from her as directed. He opted for no tie with his dress shirt and suit to keep it casual. Never had he debated over what to wear to meet a woman before.

A waitress approached the table and with her back to Michelle, bent over with straight legs to place a cocktail napkin on the low table in front of Austin. Had he been simply meeting his boss for a drink, Austin would have noticed her low-cut top revealing ample cleavage and her flirtatious smile as she asked what he wanted to drink. Austin didn't notice, but Michelle definitely did and locked her eyes with his in a challenge to his fortitude.

"I'll have a Sapphire and tonic with orange juice," Austin commanded, maintaining Michelle's eye contact.

The defeated waitress answered his command flatly and sulked off to get his drink.

"Have you reached a decision, Austin?"

"Yes, ma'am, I have," he started. "But I have a few questions first."

Michelle bristled at this. "What do you need to know?"

Austin took a breath, "First, I'd like to know if this is a monogamous arrangement. I'm not one to share a partner without my presence. Second, while I should have asked before, I'd like to know if you're medically clear. Third, I'd like to know how long your proposed arrangement would last."

There, he made it sound like he was more in control of the arrangement while conveying his understanding how this was a mutual, business-like agreement.

Michelle allowed a pregnant pause before she answered, not blinking, not moving.

"Austin. Yes, this is monogamous. Any sharing will be in the presence of the other partner. Yes, I'm clear, and I return the question to you, though I should have asked before. As to your last question, this will continue as long as it is enjoyable for the both of us. The caveat is the arrangement ends if one of us develops romantic feelings. I'm not interested in any kind of relationship other than a sexual one, but if either of us were to want more, I think it prudent to end the arrangement."

He nodded to Michelle and was about to speak when the waitress arrived with his drink.

Thank goodness for her timing so I can swallow my trepidation.

Austin picked up his drink and took a long drink. Michelle looked irritated at the interruption and his intermission.

"Ma'am, I'm clean and clear. I get tested every six months and recently received a clean bill of health. I would have stopped you if I was unsure of any results. I use condoms, but assume you're handling birth control?"

Michelle nodded in affirmation.

"Good. I would like to not use condoms, but I understand if you prefer them."

Michelle uncrossed and re-crossed her legs allowing her skirt to drift slightly higher.

Fuck, she's not wearing panties.

Austin shifted in his seat and Michelle smiled. He realized she planned the move and was enjoying his discomfort.

"Austin, condoms will be used only when we've incorporated another partner. When it's just us, you may fill my pussy with your cum."

And now my dick is definitely rock hard.

Austin flushed at the implications of her answer. They'd have threesomes, fuck yeah. And just thinking about emptying his cock in her made a small drop of pre-cum escape.

"Ma'am, I agree to your proposal."

There. He did it. He agreed to casually fuck his boss.

Michelle smiled. "I figured you'd say that. We'll discuss other terms later, but right now, I want your fingers in my pussy."

His mind went into overdrive. Here? In the bathroom? In the elevator? Her room? There's people around!

Michelle uncrossed her legs and settled them slightly apart, giving Austin a full view of her bare pussy. She slouched a little down in the chair so he could see everything. He could tell she had a Brazilian with a small landing strip above her mound. Her scent made its way to Austin and he drew in a deep breath, basking in her musky sweetness.

"Michelle. How can I please you?"

"Austin, pull your chair closer and reach across the table."

Holy fuck, she wants my fingers in her HERE AND NOW???

"I.. uh.. Michelle, there's people around." He didn't want to disobey already, but he also didn't want to get arrested.

Her lips flattened to a thin line. "Austin, you'll do as I say. I wouldn't and won't present any compromising situations. If you must know, the bartender is in the back. You're little fuck toy waitress has her back to us in a corner, no doubt texting her equally shallow friends about you. And the other gentlemen in the bar have their backs to us as well. Now, put your fingers in my pussy."

He quickly pulled his chair forward and reached across the small table. His right hand touched her knee, and then gently advanced up her thigh to her warm sex. As he neared the top of her leg, he leaned further over, bracing his left elbow on his leg, and slide his middle finger into her waiting hole. She was warm and slippery. Clearly, she was as wound up as he was, but dammit, women always hid it much better than men did.

He felt the soft ridges inside her pussy and curved his finger slightly to gently massage her tender spot inside. She exhaled a long breath and closed her eyes as he touched her spot, then slowly withdrew his finger a little. Austin felt another drop of pre-cum exit his raging hard-on and had to quickly think of some mundane email from earlier before he blew his load in his pants.

Who knew I could revert to adolescence so easily.

Austin started a slow rhythm of pushing his finger inside Michelle, touching her tender spot, then slightly withdrawing. He loved how warm she was and how slippery she'd already been when he entered her. Michelle's head started to drop backwards, acknowledging her enjoyment.

"Austin, two fingers," she exhaled. He withdrew his finger the whole way and brought it to his mouth. He couldn't move on without having a taste of her essence.

Michelle abruptly sat up and leaned into Austin's face.

"You clearly can't follow instructions, Austin. I didn't say lick your finger, I said two fingers. If I wanted you to taste me, I would have said so. I was clear about what I want." She sat upright and grabbed her cocktail, taking a slow sip and licking her lips before setting it back down.

"Since you lack the ability to follow instructions, you will now be punished."

Austin blanched.

What the fuck does she mean by punished?

Michelle leaned back into her chair, sliding herself up and crossing her legs, effectively shutting Austin down. He was frozen.

"I won't tolerate insolence. Look at your little tart waitress."

Austin leaned back in his chair and turned toward the waitress. She was still absorbed in her phone, ignoring the lounge patrons.

Austin turned back to Michelle. "Ma'am?"

Michelle steepled her fingers in front of her face as she spoke.

"You're going to go hit on her. You're going to flirt and convince her to go to the ladies restroom with you. You're going kiss her and suck her tits and touch her clit. You're going to pull out the condom in your back pocket... I know it's there... and slide it over your cock... which I know needs to enter a pussy right now... and you're going to fuck her from behind. But Austin, you're not going to cum. You're not allowed to cum. Your punishment is withholding of your orgasm. And don't think you can get off without my knowing. I'm going to follow you into the ladies room and listen to you fuck her. I'm going to stand right outside the stall as you stretch her pussy with that exquisite cock of yours and finger myself. Right before you think you might cum. You're going to stop, pull out, and tell her you're finished. Then you're going to exit the stall and stand on my left side, facing the mirror, as she gathers her wits and exits. If she cums, good for her, but you will not. I want her to see me and know she was my toy."

Austin swallowed hard. "Yes ma'am." He reached for his cocktail, but met her eyes first in a silent request for permission. Michelle nodded, smirking at his need for liquid courage. Austin downed the drink in one large gulp, stood up, buttoned his blazer, adjusted his cock, and rolled his shoulders back.

This is so bizarre, but I'm pretty sure I could cum in my pants right now if she just touched my cock.

He circled his chair and casually walked across the lounge to the girl.

"Excuse me, miss?" He asked as he came up behind her.

She startled and whipped around, and he glanced her nametag. Amber.

"Ah, Amber, I was wondering if you had a minute."

Amber jammed her phone in apron pocket and smoothed her hair in an attempt to look professional. She clearly thought she might be in trouble.

"I'm sorry, Sir, what may I help you with?"

"Amber, I was wondering if you knew how sexy you are." Lame, Austin. Real lame. "I was speaking with my boss over ther,e but I couldn't concentrate because I was thinking about your tits. Just the tiny bit I saw earlier has me out of sorts."

Amber looked down at her cleavage then back at Austin. He watched as his poor excuse for a pick up line registered in her mind, and her flirtatious smile returned.

"Oh, well thank you Sir, but it seems like you want to ask me something?"

Wow, she MUST get approached a lot if she knows where this going.

"As a matter of fact I do," Austin started, placing his right hand on the wall behind her and leaning in to her ear. "I have an issue you might be able to help me with. But we would have to leave the lounge for a few minutes, and I'm not sure your boss would appreciate that."

Amber giggled from his breath tickling her ear. She turned her head toward his.

"My boss doesn't work evenings, and the only other manager available is in the back starting the night audit. I'm all yours."

Austin silently thanked the heavens this was working. He didn't want Michelle upset with him. This whole time, he could feel her stare on the back of his neck. He felt bad for this girl, but he felt worse thinking about failing Michelle's demand.

"Perfect. Can I take you to a more private location?" Austin offered his left hand.

Amber giggled again and took his hand. The few remaining bar patrons were watching some game on the screen behind the bar, chatting with the bartender, who seemed oblivious to losing his waitress right now.

Austin led Amber by the hand quickly out of the lounge, glancing Michelle's way as he passed their table. She had laid some cash on the table and was gathering her purse, but met his eyes with a wicked smile.

The ladies room was a wide left u-turn from the lounge entrance and Austin quickly dragged Amber inside to the largest stall. He started to run through the checklist Michelle had dictated.

Why didn't he think to take notes?

Austin planted his mouth on Ambers as he grabbed both her hands and gently pinned them above her on the stall door. He heard the squeak of the main door opening so he groaned to mask the sound and pressed his hips to hers, eliciting a whimper from her. Amber was squirming against his erection, thinking it was because of her and for her. Austin didn't care, he had do this quickly. He released her hands and pulled her shirt out of her short skirt to access her tits. He yanked down her bra and moved his mouth to her nipple as she gasped for air and moaned from his teeth on her nipple. Had this been his choosing, he wouldn't be so harsh, and frankly, he wouldn't be in a bathroom, but there was still something so erotic to this whole scenario, he felt slightly more aggressive.

Amber brought her hand down to his erection and started fondling it through his pants. Austin shifted slightly left to allow her better access, and saw Michelle through the crack of the stall door and wall. She was sitting on the counter with her skirt around her waist and her high-heel clad feet drawn up to the sides of her leg. He could see two of her fingers plunging deep into her soft pink pussy, then retreating to circle her clit. Even with the soft overhead lighting, he could see her fingers were covered in moisture from her pussy and he let a long groan escape him, remembering the brief taste he had of her.

Amber was starting to be bolder, and her rubbing on his cock was borderline annoying. He stood up from her for a second and reached for the condom in his back pocket.

"Turn around," he ordered as he undid his belt and trousers. Amber gave some weird, coy look and abided, sliding her panties down and off her legs.

Austin slid the condom down his almost purple cock. By now, he'd had an erection for a solid half hour and it was going to take everything in him not to blow it on the first pump into this girl. He grabbed her left hip and pulled her toward him as his right hand guided his cock to her slit. She was warm and willing. He was disappointed to briefly feel that she shaved, not waxed, her pussy, and used this disappointment to control his desire to cum as he pushed into her tight pussy. She didn't have ridges on the inside like Michelle's ridges, and she moaned a little too loudly as she took in his length and width. Her pussy was shallow, and he could tell he was in as deep comfort would allow, yet his cock was still half exposed.

Austin began pumping in and out of her. She felt good, but he knew Michelle felt better. He watched his cock sliding in and out. He wanted to imagine he was fucking Michelle, but he was afraid he might cum, a clear violation of Michelle's demand. Amber was starting to get loud and his forcefulness was causing the stall door to rattle. He had to get this over with now, but Amber sounded like she might actually cum, and he felt it the least he could do for her.

He moved his hand from her left hip to touch her clit while he fucked her. Her clit felt hard and swollen, so he knew she was close to coming. With three fingers, he started circling her clit with slight pressure, trying to draw her orgasm out before he came himself. Strangely, he realized he didn't think he could cum anyway, because he had to follow a checklist with this girl as if he was putting together a powerpoint.

Amber began to buck back against him, and he felt his balls hitting her skin. Her pussy had relaxed around cock and he was able to thrust deeper inside her, almost to the base. He heard Michelle snicker a little on the countertop. Amber was clueless, thanks to her obnoxious moaning and incoherent words of encouragement. Austin felt Ambers pussy begin to tighten around his cock as she broached her threshold. He quickly pulled out before he succumbed, but continued circling her clit so she had some sensation to ride out her orgasm from.

Her moans were replaced with quick breathing as she braced herself against the door. Austin removed the condom and quickly did his trousers, tossing the condom in the toilet and flushing away the evidence.

"Amber, you're probably being missed at the bar." Wow, he'd never been so curt right after sex.

Amber opened her eyes wide. He watched as she quickly processed she was being dismissed, but also that she really should get back to work. She reached for her panties and made a gesture to offer them to Austin, but he stepped back and shook his head no. She shrugged, put them on and smoothed her clothing back to its original places.

Austin almost wanted to exit the stall first to spare her the walk of shame she was about to take, but again, he was almost afraid of disobeying Michelle. He allowed her to unlock the stall and open the door. There was Michelle, casually leaning against the counter with her arms and ankles crossed, a sly grin on her face.

Amber startled and immediately blushed.

"Oh my gosh, I had no idea anyone was in here! Oh my gosh, please don't report me, oh my gosh!"

Michelle shrugged her shoulders and spoke.

"Don't worry about it, I rather enjoyed listening to you. Now I know what he is capable of and am eager to make him cum again for me."

Holy fuck, that was harsh.

Amber slightly shook her head, trying to comprehend what Michelle just said, but opted to start mumbling apologies as she scurried out of the restroom.

I took my place facing the mirror on Michelle's left side, as instructed.

Michelle stood from her lean on the counter and turned toward me.

"Nicely done, Austin. How did she feel?"

Austin swallowed, "Ma'am she felt good, but I wanted to be fucking you, not her."

Michelle chuckled. "Good, that's what I wanted to hear. I know you must be sore from holding your orgasm. Please, wash that girl off you quickly."

Austin didn't hesitate to comply. He undid his trousers and removed his engorged cock from his pants. He soaped his hands and leaned over the sink to wash his dick. Michelle moved behind him and lifted his blazer and shirt so he wouldn't get them wet. She watched as he carefully rinsed his cock, trying desperately not to rub it in any way that would make him explode. He literally was cleaning a ticking time bomb.

He shut off the water and Michelle grabbed one of the fancy hand towels the bathroom stocked. She delicately dried his cock, barely massaging his balls as she dried his member. Austin groaned and lifted his eyes to the ceiling, trying to think about his wrestling stats from high school.