Please Let Me Be Ch. 15

Story Info
Tessa relaxes into Darrien while Jolie relaxes into Terry.
4.4k words
4.9
9.7k
6

Part 15 of the 19 part series

Updated 06/07/2023
Created 03/18/2015
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Disclaimer: All characters, places, and events in this story are purely fictional and have no bearing in reality. All characters are also well above the age of 18.

This chapter is split between Tessa and Jolie so enjoy the both of them. Enjoy!

Tessa: Female, 20-ish, curly brown hair, hazel eyes, pale skin, plus-size (hourglass), 5'9"

Darrien: Male, 30/40-ish, dark hair and eyes, pale skin, weightlifter body type (not body builder), 5'9"

Jolie: Female, 20-ish, long dark hair, dark eyes, mocha skin, slim/svelte body, 5'11"

Terry/Boss: Male, 40-ish, long red hair, dark eyes, native American, slim, 5'5"

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Tessa stared at the huge Jacuzzi tub sitting in the corner of windows that looked out over a metropolis far below. Darrien had brought her here, through one of the doors down the hallway they'd had a fun time in, to his gym and pool. She'd already gaped her fill at the lap pool with deep end on the other side of the room. The word 'room' being a misnomer because while it had walls it only had them on two sides and all the rest were ceiling to floor windows. Tessa couldn't quite work out what her response should be to all this wealth. It made sense since the man had purchased her for a hefty amount of money so seeing all this should be common but something about Darrien made her feel like he went for the bare minimum in most things. What does that say about me? Am I the bare minimum or a pretty purchase? She shook her head free of the thoughts.

"Arms up," Darrien said.

Tessa complied and let him peel the dress off her body. He tossed it to the side before turning back to her and one-handedly unclasping her bra behind her back and pulling that off as well. Completely comfortable being naked with him in low lighting was very different from standing nude in front of windows. Her hands twitched to cover her flaws but she was distracted when Darrien unbuttoned himself. Every piece of clothing removed made her forget more and more what she'd worried about. Seeing a man, this man in particular, undressing for her was a rush of confidence she badly needed. At the Business she'd always imagined that the only time she'd see a naked man was one of the Business employees taking a taste of the goods off the books. It had never happened before her when she'd been there but she'd heard enough rumors. This, however, felt like a dream that may wisp away. Darrien was hers, wanted her, owned her, and hadn't wanted any of the others. It's not real, her inner thoughts whispered maliciously.

Darrien, fully bared now, squatted down to turn on the Jacuzzi. She relaxed while watching the play of muscles down his back, eyebrows shooting up as she ogled his ass. Damn. He turned to her and held out a hand to lead her down the steps. Watching him walk into the Jacuzzi was mouthwatering. Tessa knew Darrien could guess where her thoughts had gone because his mouth twitched into a small smirk before flattening back out into his traditional facial expression. The man liked to pretend he didn't feel much. It made it all the better knowing she'd gotten him to laugh out loud and smile wide just for her. After he sat he pulled her onto his lap and moved her hair to the side.

"We'll have to take these off for the job," he said with a kiss to her collar. His hands wrapped around the cuffs on her wrists.

A pang of sadness came and went so fast that Tessa let it pass. "We will, sir?"

Darrien nodded then kissed her neck. Letting her head loll back on his shoulder Tessa let herself enjoy the hot tub. They sat in the silence of the tub bubbling, sated from their meal earlier and their fucking in the hallway. It's too good to be true, Tessa hated her insecurity and shoved it down deep. I'm trusting him and myself. It's only too good to be true because it's so good. Shut up anxiety.

"So, I'm great?" Darrien broke into her thoughts. He alluded to her answer when Jolie had asked how she'd been after being purchased from the Business.

Tessa laughed in response.

"No elaboration?"

"Very great," she deadpanned, "Sir."

She could feel his eyes tracking every twitch she made. Waiting him out was affecting her. Tessa wriggled but all that did was wedge his growing erection between her cheeks.

"What's the job?" Tessa asked.

Darrien was silent. He played with the wet curls of her hair before playfully biting her shoulder with a small sting of teeth.

"Darrien," his name slipped out. She was getting into the bad habit of thinking of him as Darrien only and not Sir or Master or anything else that could be considered Business etiquette. True, she'd never had official training but she'd taken the same courses as all the other goods.

A small sound escaped him, sounding suspiciously like a sigh.

"I'm planning to train you to be a maid," his answer not quite an answer.

Tessa bit her lip, her brows scrunching together. A maid? Is this a hint that I need to clean more?

"I'll be sending you into a dangerous situation as a. . .spy of sorts."

She nodded for him to continue.

"You already know how to clean from the Business, I'll mainly be training you in the espionage part."

A spy? Better than a maid, maybe, Tessa thought to herself. Then reality caught up to her. Spying was dangerous and insane. She may have blended well into the background at the Business as Tessa the Tester but she didn't want to be that way for Darrien. Having his attention had her idea of herself changing. Were these past few days just a ploy to have someone ingratiated to him enough to be his mole? Am I just collateral damage with a perk?

"You can say no," Darrien said seriously.

Can I? I'm not so sure, Tessa thought before speaking aloud.

"I want to help you any way I can."

Darrien nodded and kissed her shoulder gently. His hands had moved from her waist down to her thigh. Tessa warred between the anticipation of him touching her again and the soreness that had her lower body aching with every move. He was drawing small patterns softly on her thighs beneath the water. The tracing movements were mesmerizing in the small ripples of the tub. It was lulling her to sleep. Tessa's forehead rested on Darrien's chin and she let her eyes close. Her hands closed around his wrists. Darrien moved just enough to kiss her forehead before wrapping his arms and hers around her waist.

"You can rest, I'll wake you later."

____________________________________________________________________

Jolie looked down at the man she knew had protected her and brought her to this 'meeting' to see Tessa was safe. For a second she narrowed her eyes in suspicion. Everything he'd done would be easy enough to do, with many benefits for him, and it left her indebted. Jolie shook off the dark cloud and smiled down at him. He sent her his grimace of a grin. It was hard to believe a man who tried so hard to smile and failed so spectacularly would have an agenda.

"Is there anything you'd like me to do?" She asked free of guile.

Terry shook his head at her. His brows raised in query.

"It feels . . . odd to not do something."

He hummed thoughtfully.

Jolie fingered the materials of her clothes. Then she stopped the nervous habit and turned her eyes to Terry. He'd been watching her fingers.

"Would you do me a favor?" He asked.

Jolie took in a breath, "Anything."

"Buy some clothes."

"Clothes?"

He rifled through one of his desk drawers and withdrew an envelope that was slightly padded and with dingy corners. "Here, this should cover anything you need. I would say you could take Tessa with you so she could find some clothes as well but I am not so sure that Darrien would release her."

Jolie took the envelope mindlessly, she didn't crack it open. She already knew that there'd be more than enough money for what she'd need.

"Is there anything you want me to buy?"

"The money is for you to buy your own wardrobe. It's not for me. I can promise anything you find to wear will be more than lovely, especially if it is such a lovely woman who wears them."

Jolie wasn't sure what facial expression to wear for this but finally settled on thankful confusion.

"You will need to take an escort. I would do the job myself but sadly there are a few more meetings in my day. Let me just-" he leant over to a phone and push a button. A small buzz answered then, "yes sir?"

"I need a security escort for my friend," Terry said concisely.

Friend?

"Understood sir, I'll send James."

"Very well."

Jolie willed her eyebrows down from their perch high on her forehead. Friends, shopping funds, and a security escort, she thought. Nothing about the last minute had quite clicked in her mind. While Jolie was trying her best to work out a proper response to all that happened the door to the office opened. In stepped a young man who looked to be in his twenties like Jolie. He was tall, handsome, and exceptionally fit in a neat black suit. Jolie assumed this must be James, the escort. She immediately wished Terry hadn't asked for an escort but could come with her instead. This felt too much like being pawned off to go be something pretty somewhere else where she wouldn't be a bother to him. Jolie knew it was silly to worry that Terry was going to pass her off on someone else. He'd just took her for himself. He was investing in her happiness with clothes and friendships and comfort. That wasn't something a man would do for a women he didn't want to keep or at least have sex with occasionally.

"Lovely?" Terry asked. Breaking Jolie from her glaring at James. She smoothed out her expression and nodded to him.

"I should be done with my meetings in time for dinner at 5 if that suits you?"

You're asking me? Jolie pushed aside the rude thought and nodded to him with a small smile.

Then she left with James, the escort, to go shopping. Her heart still beat with trepidation even as she turned to look up at the building's top floor from the car below.

____________________________________________________________________

Later that night Jolie sat across from Terry in a new dress. The white fabric was slick over black leather and crossed over her body in a series of tight bands before ending in a four tipped skirt. She was rather proud of the find in all her shopping. Her body was made to be strapped in tight and her skin glowed darkly in contrast to the pristine white. Jolie knew she'd gotten quite a few admiring looks when she finished out her shopping in the dress rather than the shorts and shirt Terry had provided her. Everything about the outfit gave her confidence. More than anything she wanted Terry to want her and keep her with him. Strangely enough she couldn't figure out where this need to stay with him had come from. She had pushed aside the reasoning and focused on tactics instead. Her body was her best weapon in seduction. Jolie had her black curls perfectly arranged on her shoulders and her legs were on show in the white kitten heels she knew rode the line of sexual fantasy and too far.

So far her tactics were failing spectacularly; Terry had given her only a glance before turning back to the suited man sitting next to him. They seemed to be poring over folders and data sheets from what Jolie could see. As each new course was brought out and Terry continued to focus on work Jolie could feel the disappointment settling in deeper.

What's the point of having dinner together if you don't even notice I'm here? Jolie let her frustration grow until she gave in and did something she never thought she'd do. Her right leg stretched out under the table. Jolie was thankful that the table was small enough that she could reach across. Her toes made contact with a pair of smooth slacks. There was no recognition of the effect she was having on Terry until she slid her foot along the inner length of his shin. His lips twitched just the slightest upwards and he rearranged himself in his seat so his legs were spread wide and he was leant back in his seat. Jolie watched him as she stroked back down again. Terry's eyes flicked to hers in a promise of retribution. She loved that look so much that she bit her lip to keep in the giddy moan of excitement she felt at having him turn his attention to her.

Soon enough, however, the men went back to their talk and Jolie's frustration grew again. She hadn't stopped her attentions under the table but there was only so much she could do in her heels from across a table. He had a noticeable erection down the leg of his pants that she'd spent special attention to with her toes. Still yet he wasn't giving any further reaction. Jolie jolted when the man who'd been going over numbers with Terry stood from his seat. Her foot fell back down to rest behind her ankle. The man muttered something about getting something but Jolie was dazed by the look Terry was giving her. Heat settled low inside her and she squirmed in her seat. A flush crept over her face and she looked down at her food to escape the unnerving eyes she'd wanted on her all day.

"Lovely one," Terry said when the man had left the room.

She glanced up at him in question.

"Would you do something for me?"

Jolie nodded immediately.

His lips twitched up again and he pointed down.

She felt her eyebrows scrunch up in confusion.

"Under the table, if you please."

It took a few seconds for Jolie to understand but when she did that flush that had come over her face flashed over her whole body. Fighting her embarrassment at what she was about to do. Jolie confirmed with a look that that was what he'd really wanted. Terry lifted the table cloth just a bit over his lap and she heard a zipper drop. At that she scooted back from the table and went to her knees. The awkwardness of crawling under the dining table passed as soon as she saw her goal. Terry had his cock out and was stroking it slowly. Mouthwatering was the only word she could use to describe this man touching himself for her eyes only. She watched for what felt like minutes but must've been only seconds. Those strong hands of his sliding up and down for her benefit mesmerizing her. Every ounce of knowledge she knew on how to please a man left her head when she licked up his still moving fingers. The tip of her tongue barely touching his cock except for the burst of heat and saltiness she caught at the end. He released himself and held his hand out for her. Jolie licked up his fingers to his palm and flicked her tongue over the pulse point in his wrist. She found herself dazedly pressing soft kisses to his wrist and palm before sucking his middle finger into her mouth. Her eyes closed in pleasure as she slid off his finger. His hand flexed and she pressed another soft kiss into the center of his palm. The sound of the door opening surprised her so that she didn't see him remove his hand from under the table.

"I've found the files, sir."

"Very good," Terry answered.

A pause followed before Terry said, "She wasn't feeling well."

The man sat down, "I'm sorry to hear that. Please give her my well wishes, Boss."

"Thank you."

They soon settled back into their conversation on numbers but Jolie was already distracted. Her hands spread wide on his thighs as she leant in to press her lips to the side of his cock. She could feel his muscles contract beneath her fingers and his cock jolt against her tongue. Jolie licked a hot wet path up the stem before taking the head into her mouth. She suckled on him, reveling in the twitches of need he held in tightly. Her tongue teased the slit causing a drop of precum to spread across her taste buds. It's taste was bitter and salty but not disgusting by any means and Jolie gave a soft suck to see if he'd give her any more to taste. Jolie swallowed him down, her tongue caressing every inch of his cock on the way. He jolted in his seat, his hips pressing forward. She went to slide off him when his hand reappeared under the table to bury itself in her hair. He slowly controlled her by fucking his cock with her mouth. Every brush across her plush lips had her pussy overheating. Jolie reached down with both her hands and pulled her skirt up. Cold air brushed across her burning skin. She pushed under her soaked panties and had two fingers buried inside while she frantically rubbed her clit. Something inside her relaxed under his control. Jolie knew Terry wouldn't choke her even while he slid his cock deeper down her throat. Keeping her throat relaxed she went along for the ride with her eyes closed. Every pull created a friction in her mouth that she could feel inside her pussy. The pulse of her fingers moved in tandem with his thrusts. Jolie felt herself getting closer every second to coming when he gently removed his still hard cock from her aching jaw. She couldn't seem to force herself to care that saliva dripped down her chin to create dots on the otherwise perfect white of her dress.

The drone of voices above her cut off with the sound of the door closing. Jolie rested her head on his thigh when she noticed that the other man was no longer sitting at the table. Terry lifted the tablecloth and was looking at her with a need she felt with every part of her body. Her muscles were still tensed from almost cumming, her fingers having stopped when he did.

"So lovely," he murmured, his thumb pulling on her slack lips.

Jolie kissed the pad of his thumb and smiled up at him.

"Would you do something else for me?" he asked.

Jolie nodded. Terry pushed back from the table and helped her to stand on her shaky legs. Jolie found herself set in his chair.

"Lift your legs," Terry gestured.

She pulled her legs up with her knees to her chest. The dress rode up to show the soaked skin at her juncture. A musky smell filled the air and Jolie flushed with embarrassment at the thought that the smell was her arousal for him. Terry's lips quirked in that non-smile of his, causing her thighs to visibly clench. He pushed her thighs wide so her legs lay over the armrests. The stretch of her legs heightened her pleasure and Jolie's head lolled back on her shoulders. She watched him through her eyelashes.

Finally, he was looking at her with no distractions. One of his brows arched in appreciation at the picture she made for him; wet, spread, and needy.

Jolie released her knees to go to one of the bands holding her dress in place. There was a hidden set up of buckles that kept her breasts strapped in. She released them and the fabric fell away to reveal her still sensitive nipple piercings. Terry hissed in a breath between his teeth. The sound sent a wave of satisfaction through her and Jolie arched in the chair. Her hands finding their way above her head to grip the chair.

"Truly lovely," Terry husked. He stroked his cock slowly in lazy pulls that drew her eye.

One of his hands reached for her core. Those gorgeous, thick fingers of his rubbed her in gentle strokes.

"Terry," his name coming out in a slight moan.

"Did you buy this dress to tempt me?"

Jolie debated telling him no but knew it for the lie it was. Instead she shyly nodded. Terry rewarded her with that wide unnerving almost grin of his. The slightly off expression sent a bolt of heat through Jolie's pussy.

"You are tempting enough even in only shorts and a t-shirt." He said distractedly while still kneading her cunt, "this dress, however, is overkill. Lovely, tempting overkill."

He leant forward and licked one of her nipples gently. The slight touch echoed through her body so that she was arching off the chair.

"Too sensitive?" he asked.

Jolie squirmed but shook her head. The sensation had been nearly overwhelming but not bad by any means. If it meant she had Terry's tongue on her it'd be well worth it.

He hummed before turning to lick a slow strip over the other nipple. This time Jolie couldn't hold back the whimper of sensitivity when she arched. His eyes narrowed at the sound. She tried to calm her panting breathes with him so close to her. Terry was looking her dead in the eye from where he was still leant over her breasts. Her body was thrumming with excitement from his closeness.

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