Wicked Wednesday 222: Dear Diary (A Day in The Life…)


Nathan’s crisp strides took him into his office suite,as he headed in to work. “Good morning Alicia.”

“Mornin’ Boss,” she replied typing away. Nathan moved to his office and shut the door to begin his day. He sat down in his chair and shifted around for a moment trying to get comfortable. He needed to finish off these reports before the next board meeting. After half an hour Nathan’s cellphone buzzed. He picked it up, noting the calendar alert for his 1:30. Dismissing the notification brought up the tail end of the text conversation he’d had last night.

“Can’t wait to see you tonight.”

“Was hoping that you’d call for another date, I’ve never done those things with someone on the first date before & it’s been distracting me at work.”

“Work shouldn’t be too challenging, then we can be together.”

“See you at 8?”

“Be ready by 7:30, I have plans for you tonight.”

He took a break from the report, letting his mind wander and squirmed in his chair before getting up to pace. Moving around helped his discomfort so he settled in and went back to typing. He heard Alicia’s voice reminding clients of appointments for the afternoon and following day. A glance at the time got him back on task. His to do list needed clearing by the end of lunch at the latest and he hadn’t gotten through half of it yet.

The next few hours blurred, as reports were pulled and sent off; a lengthy phone call with the Boston office was miserable. To fight his restlessness he clicked open a browser window and went shopping for a surprise for tonight. Finding the perfect outfit from the boutique across town only took him a few moments and he ordered it, requesting delivery to the office, so it’d be ready. The droning on the phone finally stopped, and he got back to reading the claim from some storm damage at a job site. It was torture going through the day like this.

About 12:30, Nathan looked up with a start. He’d been so involved in his work that lunch had been forgotten. He should still have time to handle everything though with an hour to eat and get ready for his meeting. He ordered a bite from the deli downstairs and took off his jacket, the business wear felt exceptionally constricting today. Loosening his tie, he thought about how he always said he hated being confined and yet here he was. Grabbing his phone to make sure of the time, he remembered another thing that had to be done before the end of lunch.

A glance at the clock showed it was almost 1:00 and suddenly there was a knock at the door.

“Sir, your 1:00 is here, shall I send them in?”

He almost panicked then called out, “Just a moment!” Hurrying he threw his suit back on, foregoing the tie and left the jacket off, going for a casual, relaxed look despite how disheveled he felt. He flipped his phone upside down and went to the door.

Opening it he found it to be a potential new partner for the company and immediately regretted his decision to skip his tie and jacket. “Mr. Jameson, hello. Come in, please. Would you like anything, coffee, tea?” The young man shook his head and noted Nathan’s slightly rumpled look with displeasure. Alicia glanced at her boss smiling, “Let me know if you two need anything, Sir.” Well, at least she hadn’t called him Boss in front of this important client. He settled back at his desk uncomfortable and visibly nervous, motioning for Mr. Jameson to have a seat;a surreptitious glance at his calendar showed the meeting was indeed noted to be 1:30. He’d have to speak to Alicia. After an hour the two gentleman concluded their meeting and Nathan stepped out of the office to find his lunch, now cold, sitting on the corner of Alicia’s desk. She was on the phone so he decided chastising her could wait and took his lunch into his office to eat. Half way through his sandwich, he got a text reminding him of his lunch time video call. Realizing that he didn’t actually get to complete it, and that he wouldn’t get to now he snapped a few pictures and texted them in reply. She had said that she wanted to see him at work, and he didn’t want to take any chances of ruining his date tonight after the fun they’d had last time.

On his way out of the office Alicia handed him a package that had been delivered earlier that afternoon. “Here ya go, Boss.” She gave him an impish smile as though she knew what he was up to and waved as he left. When he got home, Nathan immediately checked his phone, finding a message, “Not what I asked for…” and stripped out of his suit, hanging it neatly. He hung his head, knowing he was going to hear about that missed call earlier today and reached into his night stand for his journal, slightly crushed from being opened and flattened out numerous times.

“Dear Diary,

Today was a disaster! Mistress spent all night texting me dirty pictures and messages! By the time I got to work wearing my jewelry I was completely distracted and She told me I needed to focus. I failed one of Her tasks that She set before me at lunchtime; I was almost literally caught with my pants down by a client while I was getting ready for our call so she could see the ring she gave me and I just remembered that I left my panties under my desk at work. I hope the cleaning crew skips my office!

I’m waiting for Her to text with further instructions and I’m so restless. A cock ring has been torture especially when I’ve been thinking about Her all day. I know She dressed in something smart for work and I can picture those gorgeous legs peeking out from underneath an almost, but not quite, too short skirt. Her boss really should say something to Her about choice of dress of course, but I can’t imagine that he would want to correct such behavior. I know I won’t be doing it…

He paused his writing as his phone went off. “You are to be changed & ready by 7:30. We’re having dinner & then punishment since you disobeyed.”

Putting away the journal, he smiled. He’d hunted all over stationary shops to find one like this, all pale pink leather decorated with a pretty white ribbon bow on the front. He set his diary aside knowing that he would be expected to finish the entry later.

Nathan frowned and checked the time as he opened the box that he’d brought home from work. He pulled out black lace panties, a pair of stockings, and a garter belt and began to dress, making sure his garters were straight and the stocking seams lined up in the back. He ran his hand down the length of his cock wanting very much to remove the ring and touch himself more, but no doubt Mistress would be very unhappy. At 7:30 he was ready and waiting outside when a gunmetal BMW pulled up to the curb. He walked over to the car and climbed into the passenger seat smiling, “Hello Boss. How are you this evening?”

Alicia smiled back at him, “You will follow instructions better in person, won’t you?”

“Yes Boss!”



5 thoughts on “Wicked Wednesday 222: Dear Diary (A Day in The Life…)

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