Abbey's Will

Abbey likes to keep an eye on her star employees. Will likes to keep his boss happy. Together, they make an emotionally-conflicted pair with an undeniable attraction for each other. But when will their desire cross the line?

*********

"'You never open your mouth-'"

"'-until you know what the shot is.' I got it, Abbey."

"Are you sure you want this job? I thought you wanted to get out of the field, take a seat in the front office." Abbey rested her full bottom on the front of the mahogany desk in her executive suite.

"One last ride," Will promised, his brown eyes locked on hers. "Then I'll back here, by your side in the Oakland bureau, day in, day out. You won't be able to get rid of me."

Abbey matched his piercing stare. "If that's what you want."

"Scared I'll make a mess of things?"

"You're the star player on this team, Will. You know it, everyone knows it."

"But the cameras stay on?"

"For your first dates with Lisa, yes. It's protocol, for her safety and yours. I'll be watching you."

"Can't stop, won't stop, huh, Abbey?"

"That's why I'm the best."

"I can't argue with that. I hope Jed recognizes his good fortune."

"He does." Abbey wiped her sweaty hands on her linen pants. "And I recognize mine."

"Flying back and forth, East Coast to West Coast, must be hard."

"We don't go more than two weeks without seeing each other. It was fun when we were younger. But after we turned 40..."

"You look fabulous, by the way."

Abbey hid her smile. "Both of us are too stubborn to move. Uprooting our careers and starting over in a new city?"

"Couldn't you open a branch in Washington?"

"Different market, more competition, but yes, I could."

"Boom." Will put his hands up. "Problem solved. I wouldn't mind helping you find wealthy female politicians who need their fires stoked by a seductive courtesan. Field trip!"

"The real problem is," Abbey crossed her arms, "both of us want a wife, but neither of wants to be one."

"Being a wife doesn't sound so bad." He sat on the leather loveseat to the left of the desk. "Your wife, specifically. What would the duties entail?"

"You couldn't handle the position."

"Have you seen a position I couldn't handle?"

Abbey scanned Will's sculpted body, clad in his usual sweater and dress pants. "I have not."

"Moot point. Based on your improved mood, I presume you and Jed are on the mend?"

She walked away from her desk and joined Will on the adjacent cushion. "He flew in Thursday night, apologized, and..."

"Ate you out for three days?"

"Dude."

"Sorry. Forgot it's Monday morning. I had my friend hat on. Taking it off, replacing it with my employee helmet."

"Can you wear both at the same time?"

Will crossed his ankles. "I thought that was my entire job description."

Abbey's face fell.

Will leaned in to comfort her, then drew back. "I'm jealous. I can't be an impartial observer of your relationship with Jed."

Abbey stood up. "This is unfair to you."

Will reached up to clasp her fingers.

Abbey let him tug her back down to a seated position.

"Where are you at now?" he asked, reluctantly letting go. "You appear more relaxed than you did last week."

"We are good." Abbey retrieved her laptop and changed the conversation, though she remained on the loveseat with her employee. "Let's get back to this new new client, a result of the old new client."

Will looked at the screen, which featured Lisa's profile. "You were correct about the opening an untapped market. She is the definition of a well-connected, self-made millionaire. I will show her a good time tonight."

"Be careful with this one. Lisa is the mom of a friend of my daughter."

Will pretended to keel over. "You have a daughter? Since when?"

"Since I was in my last year of university. No, that's when I got pregnant. I gave birth to Amelia that summer after graduation."

"You have a baby. Whoa."

"She's a grown woman. At least that's what she thinks. 21 and can't tell her anything."

"I've known you for how long?"

"Too long."

"And I've never met, Amelia is it?"

"My mother and grandparents raised her back at home. I was looking at the Rhodes and a Fulbright and... We made the best decision."

"Do you regret it?"

"Never. I'll always be Amelia's bio mom, and Jed loves that she calls him Uncle Stepdad. One Christmas, when she was probably in middle school, Amelia asked him if my business made me a whore. He told her I didn't go on dates, I manage you suitors."

"True."

"Then Amelia asked Jed if that made me a pimp, and Jed stuffed his mouth with a gingerbread man. Do you have kids?"

"We're talking about me now? Whew. It's complicated."

"I've got time."

Will pushed on. "About a decade ago, before you recruited me, I was with someone. She got pregnant with twins, a boy and a girl. She told me they were mine. Then three years later, we split up, and she told me they weren't mine."

"Whaaat?"

"Twist: the boy was mine, the girl wasn't. The other father wanted no part of this mess. So I officially adopted my own daughter, and my ex and I have joint custody."

"You're a dad."

"A hot dad?"

"When do I get to meet them?"

"Yours first."

She shook his hand. "Deal."

Will didn't let go. "All this time I've been working for a MILF."

Abbey took her hand back. "Gross."

"It's a compliment."

"Is it?"

"If you think about it... maybe?"

...

At home in her pineapple pajamas, Abbey reclined on her bed and opened her laptop to check the live security footage of Will's date with Lisa. Their small talk over shrimp scampi did not hold Abbey's interest, so she muted the couple while she watched a singing competition show playing on the television on her wall.

As the competition wound down, the closing credits gave way to a rerun of a homely guy/hot wife sitcom. Abbey noticed Will leading Lisa out of the restaurant.

Eventually they arrived at the building that housed the company office, including the assortment of bedroom suites that suitors brought their clients to on their first dates.

Will let Lisa explore the living room area, as clients often did, concentrating on the interior design to take their minds off the fact that they were about to engage in sexual intercourse with a paid professional. Abbey saw Lisa open a bottle of water and take a drink, building her courage. Will stood near Lisa, allowing her the space to feel safe yet supported. As they engaged in conversation, Lisa edged closer to him. Her hand brushed against his arm. She led him to the next room.

Will opened the door, and the couple moved to the bed, adorned with a set of standard pillows, a blanket, and a fitted sheet.

Abbey watched Will work his magic, ensuring his partner's comfort, making her feel beautiful. Lisa was entranced by Will's ministrations, his continuous requests for affirmations as he moved further. He let Lisa undress him, peeling the wrapping off of her gift one item at a time, until he sat on the bed in his boxer briefs.

Abbey felt a pang of envy as Will caressed Lisa's body and fumbled with the zipper on her dress, which caused the couple to giggle together. Lisa showed him how to take it off. Will removed the dress, then her panties, then her bra.

Then his briefs.

Will let Lisa select a lubricated condom from the bedside jar. She rolled the latex on him. He gathered her into his arms, and they undulated on top of the blanket, his hands searching for any unreleased kinks in her body that he could massage into relaxation.

When Will entered Lisa, Abbey frowned and crossed her arms, her eyes shooting daggers at the screen. Then she shook herself out of her envy, reminding herself that she had no claim on Will.

Abbey watched Will pump into Lisa's body. She was familiar with his method of extracting every morsel of pleasure from his partner, leaving them exhausted on the mattress, wondering what delights had just coursed through their limbs. And Will did not disappoint in servicing Lisa, who experienced a series of screams, convulsions, and gasps until she lay enervated from the excitement. Will arranged his sweaty body next to hers, both of them blithely resting on the pillows.

Abbey was proud of her employee's performance, but she couldn't help but wish she had been the recipient of Will's talents.

...

After Lisa departed, leaving Will with a hug and an gratuitous envelope, Will rested in the bed.

Abbey wondered what he was pondering. Usually once the date ended, the suitors counted their money, clocked out, and left the building.

Will remained in his position, lying in his underwear. After a moment, his focus turned to the camera aimed at the middle of the bed.

Abbey saw him silently mouth to the camera, "Abbey."

On previous first dates, he had always silently accepted that she was watching. All of her suitors, and clients, knew they had an audience. However, they rarely acknowledged the women and men behind the curtain unless there was an emergency.

Will's date had unfolded splendidly, as Abbey had expected it would.

So why was he still in the room, calling out to her without a sound?

She typed Will a text on her phone: "Are you okay?"

Abbey watched Will climb off the bed and find his phone in his pants. He typed back.

Abbey's phone chimed. She read the message: "Watch me."

Will returned to the mattress. He fluffed the pillows and leaned his head back. He stretched his long legs, placed his right hand behind his head, and let his left hand drift toward his crotch.

Abbey realized that Will was confident that she would continue viewing his show. He needed no confirmation, yet he also allowed her plausible deniability.

Abbey let her right hand drift toward her crotch.

It was already wet.

Will rubbed the growing bulge under the fabric.

Abbey slid her hand into her damp panties.

He rolled his waistband down, underwear now around his ankles.

She did the same with her underwear and pajama pants.

He stroked.

She fingered.

He teased his cock head.

She flicked her pink clit.

After a few minutes of each of them stimulating their own nether regions, Will strained to reach his phone. He used his right thumb to type.

Abbey grabbed her beeping phone. "Now."

Will jerked hard with one hand and cupped his balls with the other.

Abbey kept two fingers in her creamy slit and two knuckles kneading her throbbing bud.

Will spurted in an arc that landed in a white streak at the foot of the bed.

Abbey squirted on her fingers, creating a puddle on the sheets. She closed her eyes and savored her synchronous orgasm with her friend Will.

Her friend.

Her employee.

A person who was not her partner, Jed.

The phone beeped again.

Abbey shut down her computer, turned off her phone, and took a long shower.