Please Let Me Be Ch. 14

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Disclaimer: This chapter contains anal, keep in mind that if you plan to do anal play to do a butt-ton of research (pun intended) and to stock up on supplies properly beforehand. This chapter is purely fictional, all characters, events, and places are entirely made up and meant for this story alone. Thus, what you read about anal here is for the story, not a step by step manual on how to. Study up and play properly. Also, carpet burn is a bitch (just fyi). Everyone in this story is well above the age of 18 and the plot does feature some consent issues so be sure to always get consent and practice legal and safe sex.



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″


Tessa fought back a moan as she woke. Instead out came a note of inquiry as she realized she was nestled in Darrien’s arms but his fingers weren’t where she expected them.


“Such a good girl,” Darrien whispered in her ear, causing her body to relax and allow him entry. His fingers delved deeper.

“Are you-?” Tessa mumbled before coming fully awake when he scissored his fingers in her ass.

“Something new,” he said while nipping at her ear.

“My ass?” She asked confused and surprisingly turned on. Her body was ready for more sex despite being sore from the night before. Waking up to someone fingering her ass was shocking but the burn and stretch of the entry felt good in a weird way. “How long?”

“An hour,” Darrien sucked on her ear and removed one of his hands while replacing the missing fingers so she still had three spearing her open.

“Crazy,” Tessa tried to think and not say but failed, “Shit.”

“Nope, pretty clean down here,” Darrien chuckled and leant over her for something off the nightstand. He crinkled something in his hands before sliding out of her ass completely,

“Ugh, I know you bought me but this could be something to talk about before diving in.”

Darrien huffed a laugh before angling to kiss her. His lips distracted her from what his hands were doing until she felt something nudge her hole. He lifted his knee that had been wedged between her thighs so she was split wide open to him. Tessa gripped his shoulders and pulled back from his kiss. Her body was still lax from sleep when he slid the plug inside. She gasped at the feeling; full, hot, pressing at her from the inside so everything was pushing. It slipped into place and Tessa tried to breath.

“Good girl,” he murmured into her hair. His held her to him.

Tessa sighed into his chest when he laid his knee back down slowly. Her body was still trying to accustom itself to this new intruder but Tessa couldn’t work up any anger at anal so early in the morning. She trusted Darrien to take care of her and make her feel great. So far he’d been kind to stretch her out before putting anything inside. She’d heard stories at the Business of things not going that way and how badly things could end. Darrien had used enough lube that his hands were still wet where he held her to him.

“We have a meeting soon,” Darrien said into the darkness of the room.

“So you’ll take it out,” she coughed at her pleading tone and tacked on, “sir?”

He chuckled, “No.”



Tessa absorbed the idea of wearing a butt plug in a meeting with a quaking heart that she strengthened through sheer will power.

“A meeting?”

“With my boss,”

“Oh,” Tessa swallowed audibly and screwed up her face, “okay.”

She could feel him laughing silently against her chest. Tessa pushed at him in retaliation but he only barely rocked back before laughing harder. Shooting him a glare, Tessa wiggled free of him and headed to the bathroom. Flicking on the light she stared at the toilet with consternation. Darrien laughed out loud now from the bed. Tessa scowled at him briefly before going into and closing the door with an angry click. A few minutes later she came out still completely nude but with clean teeth, skin, and orderly hair. Darrien had tidied up the supplies from when he’d woken her and dressed in his suit. He held out a shift dress and a bra for her.

“Thank you,” Tessa looked at the bathroom then shrugged before putting on the clothes in front of him. He’s seen me naked before, am I supposed to be embarrassed putting on clothes rather than taking them off?

Darrien had a smile in his eyes when she snuck a peak at him.

“No panties?” She had to ask.

The smile moved from his eyes to his lips. Instead of answering he stood and opened the door for her to exit through before him. Tessa admired the dress he’d given her and thanked goodness for the bra. bahis şirketleri Feeling armored up in spite of the lack of underwear she tried to ignore the way every step sent the plug rocking into what she thought was her cervix. It was a painful pleasure both inside and on the entrance. Rubbing and jolting, she made it through his rooms, down a hall, and to an elevator she’d not known existed before now. Darrien’s hand on the small of back guided her every step of the way and helped keep her from leaning against the walls of the elevator. He pressed a button for the top floor and punched in a code that turned a small light green. Tessa was distracted by the sight of her in the shift dress. Each of the walls, including the elevator doors, was a highly reflective black stone. She almost didn’t recognize herself. So different from Tessa the Tester.

She had curves in this dress, the green material stretched across her tits and hugged in at her waist before spearing out over her hips. Tessa shifted, letting the feeling of the plug give her jolts of heat. Her fingers found the cuffs she wore, the same green color as the dress with black trim and metal dees. She’d forgotten she was wearing them and the beautiful collar. Her eyes had become used to seeing the things that marked her as his.

She flicked a look up to her face and noticed she was smiling and blushing. Tessa hadn’t realized that the heat she felt across her cheeks would show on her face. She glanced at Darrien beside her. He looked like he had when she’d first men him. Like a demon sent to entice her. Dark eyes focused on her causing Tessa to jolt. He lifted an eyebrow in his way of making fun of her. She squirmed but never let his hand leave her back. Her tongue slid along her lips and she looked up again at their reflection to find him watching her. A shiver flashed across her neck leaving her tingling and needy for Darrien when the doors opened. He hummed a sound that Tessa took to mean later. They entered a hallway much like the one on Darrien’s floor. He led her along to a series of double doors at the far end.

“He’ll love you,” Darrien whispered before opening the door for her.

Her eyes widened at his words and something relaxed in her chest. She nodded to him and entered with her head high, shoulders back, stomach in, and a smile on. Her smile stretched wider when she saw Jolie. She took a step forward to greet her friend but halted when Darrien pressed against her back. He closed the door behind them and escorted her to the front of the office. A desk took up the bulk of the space but there were four chairs spaced around the room. Darrien guided her past all of them and brought her straight to Jolie who smiled widely at her. Tessa was so happy to see her that she’d missed the fact that Jolie was dressed in shorts and a t-shirt. She tilted her head in question before shaking it and coming forward to hug her in greeting.

“Jolie, I’m so happy to see you!”

“Ah, Tessa, I can’t hug right now,” Jolie took a step back but smiled an apology.

“Oh,” Tessa felt her smile dim and noticed Jolie look at Darrien with concern over Tessa’s shoulder.

“I would love to hug you,” Jolie continued quickly, “I’m just a little . . . injured?”

“Injured?” Tessa asked at the same time as Darrien. She turned to him with a frown that echoed on his face.

“Boss?” Darrien asked the man sitting behind the desk.

“Marco and Jamal took it too far with her, she’s with me now.” Darrien’s boss said with a flash of clenched teeth. He visibly relaxed when Jolie touched him on the shoulder and whispered what sounded like Terry. He gripped her around the wrist before releasing her to play with the small bell on her cuff.

“So no hugs,” Tessa nodded and smiled with her eyes at Jolie.

“No hugs but I am happy to see you.” She answered. “How’ve you been?”

At that question Tessa could feel Darrien’s fingers twitch on her back.


His fingers twitched again.

“Great?” Jolie asked.

Tessa licked her lips and felt her face flush when she glanced at Darrien. He was observing her with those dark eyes of his.

“So,” Tessa shifted awkwardly when Darrien’s hand slid down lower on her back, “those are new clothes.”

Jolie laughed, the Boss looked at her at the sound with an inscrutable expression.

“These are a gift, the clothes we had when we left haven’t lasted long. Silk, you know?”

Tessa nodded and fingered the hem of her green dress in understanding.

Jolie and Tessa both smiled before turning to the Boss when he cleared his throat.

“It is a pleasure to meet you, Tessa, I am glad to hear you enjoy being here. I am Terrance, you may call me Boss or Terrance if it pleases you.” He stood from his seat to take Tessa’s hand and press a soft kiss into her knuckles. It made her smile at him with genuine warmth. The whispered Terry Jolie had said earlier making sense now.

“Boss,” Darrien said with a grin Tessa bahis firmaları wasn’t expecting.

“Darrien,” he returned with a baring of teeth he must’ve meant as a smile because Jolie smiled too.

“I’m hoping to use Tessa in that job we’ve discussed.”

Tessa looked to Darrien with surprise that was replicated on the Boss’s face.

“You want to put her there? As service?” The boss asked before nodding as the surprise left his face.

Darrien’s hand slipped further down Tessa’s ass as he answered, “I think she can blend in just enough to fit the role but still be noticeable enough to work to our advantage. I’ll train her.”

Tessa was shocked at this many words from Darrien as well as where his hand was headed.

“As long as you’re willing to train her then I can see why you think she would work out well.” The Boss looked her up and down in consideration just as Darrien’s fingers slid down her crease to rest against the plug with light pressure.

Tessa flushed from her head down and kept her eyes down so she wouldn’t make eye contact with Darrien’s Boss of Jolie while he did this.

“I can train her for this, Tessa’s smart,” his fingers rubbed on the plug at those stupefying words. Tessa stumbled a bit and her eyes shot to his but he was still looking at the Boss.

“Then I give you leave to do so,” The Boss answered.

“I’ll think she’ll do beautifully.” His fingers pushed the plug in a circular move.

Tessa choked a bit and coughed to clear her throat.


“I’ll be there,” The plug moved again.

“Will you need back up just in case?”

“Not at this moment, Tessa and I will be more than enough.” A jolt from his fingers echoed up Tessa’s spine.

“This is a heavy job,” The boss said, his words barely registering to Tessa as Darrien had the plug pulsing every other second. The gently push having her weave on her feet.

“She can handle this,” his fingers hitting harder before going back to the waves of small jerks. “Just the right kind of push for my girl.” The emphasis was in his fingers rather than his words.

“Let me know if you need anything, I know you have your hands full already.”

Tessa hiccupped a laugh at that phrasing then gasped when Darrien had his fingers doing that circular move from earlier that sent the plug riding against her cervix.

“Will do, Boss,” Darrien stepped into Tessa’s body, his hands not stopping.

“We should set up a meeting time for Tessa and Jolie. I am sure they’d like to catch up more.” The boss said.

Tessa’s smile was wobbly but real when she laid her head on Darrien’s shoulder. She tried her hardest to focus on Jolie and the Boss and must’ve passed it off because Jolie smiled back at her before looking down at the Boss and nodding happily.

“Yes, Boss.”

“Good, I am sorry to say I have a meeting soon.”

“Thank you for your time, Boss.”

“The pleasure is mine, Darrien.”

Darrien grinned and finally let up on the plug. His hand slid back up to the spot it’d been in before when he’d escorted her in.

“Tessa,” his breath brushed her cheek.

She smiled and worked her legs into standing straight after all of that. She waved at Jolie and the Boss and let Darrien guide her from the room and back to the elevator.

She laughed when he pressed her back against the wall at they waited for the elevator to arrive. He kissed her soundly, a messy wonderful press of lips and tongue that had her stuffing down a moan that wanted out. Tessa rubbed herself against him with an arch of her back that left her nipples aching to be free and in his hands. Darrien gripped her hips and ground his erection on her thigh. Knowing she’d made this man think up these plans made her hot. Knowing that he was going crazy for wanting to be inside her made her hotter. The elevator door dinged open and he tore them apart to pull her in and punch the button for his floor. He kissed her until the door closed. Then Tessa was pressed into the doors.

“Brace your hands,” Darrien grunted while he hiked up her dress. He groaned when she was bared to him. Tessa heard the zipper of his slacks being pulled down and she clenched deep inside. His fingers played with the plug, gently rocking it inside her. She saw him ripping a condom open with his teeth in the reflection of the doors. So fucking hot, she thought as a shiver slid down her spine at the sight of him sliding the condom down his erection. He stroked himself while he worked the plug free of her. Tessa closed her eyes when it finally popped out. Cold, aching, and empty she wanted him inside. Now.

Darrien tucked the plug away in his jacket before spreading her cheeks and lining up.

“Yes,” Tessa moaned when his cock head made it past her rim. The stretch was a small burn of pain. Darrien reached under her and started massaging her clit. He leaned over her and groaned into her ear. He waited until all her muscles loosened before sliding in kaçak bahis siteleri an inch. He worked himself in inch by inch. Rocking back and forth, Tessa’s eyes flickered while she panted hot breaths against the cool stone of the elevator.

“You’re such a good girl, Tessa.” Darrien’s gravelly words made her pulse around him.

She groaned and pushed back that last little bit onto his cock.

The elevator door opening sent Tessa stumbling forward. He caught her around the waist and stepped forward with her. The move sent his cock sliding out almost all the way and back in with a jolt that had her falling.

“I’ve got you,” he said into her ear. His arms around her waist as his hips ground him further into her ass.

“God,” She moaned wantonly in the hallway, “Darrien.”

His stomach clenched where it was pressed against her back. Tessa let her head fall back on his shoulder.

“One step at a time.”

Tessa groaned at the thought of walking down the hallway with him buried inside her.

“If you don’t walk to the door someone might come out into the hallway.”

Her thigh’s clenched at the thought. Eye’s slitting open to glare at Darrien she regretted looking at him because it just made her ass tighten. Darrien gritted his teeth and kissed her harshly before pushing her a step forward. Tessa’s hands shot for the walls to steady her. He stepped after her and fucked hard into her. Another stumbling step forward, another thrust, again, and again, and again. Head growing dizzy and knees growing weak Tessa reached out for the door to their rooms. She fell short and would’ve fallen completely if Darrien hadn’t caught her. He lowered her to her hands and knees.

“Wanting to fuck doggy style in the hallway, such a dirty girl.” His words sent a thrill through her. He slid out slowly when she laid her head on her arms and arched her ass into the air for him.

“Darrien,” she cried out.

“Exhibitionism makes you wet?”

She gasped when he fucked back into her again, his hips moving aggressively.

“Answer me,” his hands gripped her cheeks painfully.

“You make me wet, sir.” She choked out the words.

He groaned and fucked her so hard her knees, already weakened, slipped on the smooth carpeting and spread her further for him. Darrien was braced on hands as he pounded her into the floor.

“Hold yourself open for me,” he ground out.

Tessa’s hands went to her ass and she pulled her cheeks wide for him.

“Good girl,” He ground out with a grinding move that rubbed against her pussy from the inside and had her cumming hard around his dick. A choking sound came from him and he tried to pull free but her body was sucking him in deeper. “Fuck!”

She tried to focus on his voice but her vision had grayed out and every sound was coming from so far away. Everything about her was focused on the spasms of bliss that rocketed out from her core. Cumming from her ass was a whole new experience. Her clit was rock hard and throbbing in tandem with her ass and pussy. The pounding of her pulse filled her ears and the moans came from a long way off but Tessa knew they were all hers. Darrien’s body was collapsed on top of her. His lips kissed over her neck messily while his weight held her captured beneath him.

When Tessa came to, Darrien was slowly rocking his hips and his cock was barely starting to soften in her ass. Her hands were twitching weakly out to the side, palms up on the carpet. Darrien was caressing her head, her neck, her shoulders, her arms. Anywhere he could reach without moving off her he touched. Eventually Tessa shifted and Darrien slid from her ass and laid back on the carpet beside her. She turned her head to him with a lot of effort to watch him tie off the condom and tuck it away with the plug. He gently groped her ass, causing her to laugh, before pulling down her dress and putting away his dick. They both laid there in the hallway staring at each other.

“We should move in case someone comes.”

“No one else has access to this floor.”

Tessa gaped at him.

Darrien laughed at her expression and crinkled his nose at her pitiful attempt to swat him for lying to her.

“Bastard,” she tried to say under her breath.

“You liked it,” he smirked at her.

Everything they’d done flashed through her mind and Tessa groaned before burying her head in her arms from the mortification.

“You played with the plug in front of your boss. What’s wrong with you?” She spoke to the carpet.

“Everything,” he said, “and you liked it all.”

She groaned again.

“Stop making those noises or I’ll fuck you here again.”

Tessa turned to give him an incredulous look. He shrugged, every movement languid. Stretching out Darrien rolled back towards her to kiss her on the lips before he stood back up.

“Come on, we need food, a bath, and a nap in that order.” Darrien helped her up from the floor. He opened the door for her and blatantly stared at her ass as she entered.

“Yes, sir.” Tessa answered with a sway to her hips, the aftershocks of pleasure making her lightheaded.

“Cheeky,” he said.

“And you like it.”

To be continued . . .

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