Mike's weekend did not go well. After he got home late, he couldn't stay hard with his wife Stephanie when she tried to treat him with his regular Friday evening blowjob. The stage was set: she eased him into his La-Z-Boy, put an Arberg 10 year in his hands and was on her knees between his legs, wearing a set of lacy purple lingerie. She slobbered at Mike's cock for at least half an hour, and while he had moments of perking up, couldn't maintain it.
Was it having orgasmed earlier at Linda's command? The stress? Probably, but also comparing Stephanie's frumpy, slightly saggy, middle aged energy to Linda's tight body and sexy intensity, no matter how cruel she'd been, wasn't a fair contest. It got so bad he stormed up and off to his home office, where he started to figure out how to send the crypto to Linda.
Stephanie wasn't one to aggressively monitor their finances, but he'd have to figure this out. Maybe a bank account on the side to fund this blackmail operation.
Sunday night, in his work email, he saw a meeting invitation sent to him from Linda. It was an innocent title blocking off most of his Friday afternoon: "Client Offsite - Four Seasons." That terrified Mike, but he wondered if that meant he was in the clear from Linda's power plays the first four days of the week. He couldn't fall asleep until three in the morning, wondering.
And when he got into his office and sat down at his desk a few hours later, Linda strolled in immediately behind him with two coffees in paper cups. He stared down at her. She smiled, checked over her shoulder, and then put her mouth over one of the cups to drop a massive glob of spit into it.
She set it on his desk and continued to smile at him, sipping her own.
Mike looked down at the solitary cup of coffee, then back at Linda, rigid in her spot. Understanding the expectation, he reached forward, picked it up, and started drinking it. If he was being honest, he couldn't really taste anything different in the hot liquid, but they both knew it wasn't about that.
In a low voice that nobody could possibly hear outside of the office, Linda growled, "This is the part where you say, 'Thank you, Ma'am'."
Mike hesitated. This 19-year old couldn't be serious. But she wasn't cracking a smile.
"Thank you, Ma'am," Mike bumbled out quietly.
"Thanks, Mike!" Linda belted out loudly for anyone outside Mike's office, spinning on her heel. "Happy Monday to you too." She walked out his door, and that was the last he heard from her on Monday.
Tuesday morning, Linda came back into Mike's office with two cups of coffee again. She spit again. He drank it and thanked her.
"Thanks, Mike!" As she yelled it this time and left, she discreetly threw a small plastic bag on his desk. He quickly slid it off and inspected it more closely with his back to the door. As he removed and unfolded a small piece of dark fabric, he realized it was a dark green mesh thong, tiny and light on his thick fingers. It was accompanied by a small folded note, printed on computer paper:
"My training thong from my past week's worth of spin classes. Your turn to wear, all week. Expect random inspections in office."
Mike hesitated briefly, but then the thought of being unemployed and everything that came with that compelled him to close his office blinds and squeeze into them. They had a fair amount of stretch, but the size difference between Linda's round, petite butt and Mike's beefy six-four, 230-pound frame was stark. The back wedged tight into his ass crack, and his cock couldn't even fully tuck in the front.
He wore it the rest of the day, not daring to change until he was in his car to head home.
He wore it Wednesday too, even right before his regional sales meeting with a handful of his directors. He had his office blinds closed to practice some standing, opening remarks, when Linda brushed in.
"Linda, please..." Mike begged. "Not now."
"I can be out in sixty seconds if you let me," Linda replied curtly. "Bend over for inspection."
Mike rolled his eyes and leaned forward slightly against his glass window, like the cops were about to frisk him. As Linda starting to tug at his pants, he loosened his belt to speed things along for her.
"I'm wearing it," Mike insisted.
"Great," she replied. "One more thing, then."
She pulled his pants down and they dropped to his ankles.
Linda was confident Mike would be wearing the panties, and he was. But she had another goal in mind as well. With one finger, she moved the rear of the panties to the side and produced from her blazer pocket a small black butt plug, no larger than a small tulip bulb.
"What the fuck?!" Mike lurched and hissed, trying to keep his voice down, as he felt it start to tunnel into him.
Linda gave his beefy ass a smack, surprisingly painful for such a small hand. "Relax, Mike. Just a tiny butt plug."
"My presentation is in 20 minutes," Mike scowled, wincing as his body adjusted.
"I know -- it'd be a shame if you didn't have this in there then," Linda replied calmly, pushing against Mike's asshole until she felt it was secure. "There, all set! Knock 'em dead. Don't mind me but I'll just stay in here until you leave. Wouldn't want you sneaking it out prematurely."
For the next 20 minutes before his presentation, Mike breathed deeply to let his body adjust to the foreign object in him. Linda stood in the corner of his office, mostly on her phone, occasionally glancing up to make sure Mike wasn't reaching into his pants to pull the plug out. He could stand okay, but walking was different. As he headed to the conference room for his presentation, he knew he was waddling slightly, and just hoped it wasn't too obvious.
Twenty minutes later, Mike led the presentation in the conference room. His speech was good, but he paced a lot less than he normally did, and a few times he found himself losing his train of thought as his body continued to acclimate. The presentation was primarily for directors, but a few interns and other junior staffers lined the back walls, out of the way where they could quietly take notes. Linda was among them, and of all the times Mike looked at her, she never even cracked a smile.
It was almost worse that way. It made him feel like he was going crazy. Like her games were all in his head.
Immediately after, he rushed back to his office, keeping the blinds closed to push the plug out. He threw it into his desk drawer angrily.
Linda hadn't escalated anything Thursday beyond the typical spitting in Mike's coffee and checking briefly to make sure he was still wearing the thong he'd been given. But he was nervous for Friday. Linda had blocked off Friday afternoon for him as a "new business meeting" at the Four Seasons down the street. Earlier in the day, she'd slipped him another computer printed slip of paper, simply "Room #1017" printed on it with a keycard. When he headed out to the hotel, he noticed Linda wasn't at her desk, and had presumably left before him.
He made a beeline through the hotel lobby to the elevator, then arrived at room 1017. He took a deep breath, entered, quietly closed it behind him, and looked around. It was a large suite, with a sprawling sitting room and kitchenette separate from the bedroom. Off the main hall, Linda was sitting in one of the high-backed chairs in the sitting area, sipping a glass of water. She was wearing a dark blue pantsuit with white blouse under. Her long dark hair was pulled back in the usual messy pony tail, maybe with an extra lock falling across her face. Maybe it was the flattering fit, but Mike realized she was the only woman he knew who could make a pantsuit look good.
They looked at each other for a long minute, until Linda finally spoke.
"This is your home turf, right Mike?" Linda asked. "This is what you do? Entertain clients?"
"Well..." Mike paused, rubbing the back of his neck uncomfortably. "Usually not in hotel rooms. Lobbies and restaurants, maybe. The golf course...if you want I can help you work on your swing so that..."
