Sunday July 15, 2018
Donna sat behind her desk and looked at the stupid baseball cap in disgust, as if she would wear such a thing!
But her fingers touched the brim and picked it up none the less, she was desperate to land the client for the talent management company she worked for, if she didn’t she’d be out of a job by the end of the month. He’d sent it to her in a box filled with other trinkets from the various companies he’d invested in, but it was the only one that seemed like she could make use of.
She let out a sigh and brushed back her hair before slipping the cap on her head and looking at her reflection in her small hand held mirror. She looked ridiculous.
Her stylish suit and carefully styled hair clashed in every sense of the word with the low fashion cap and he frown on her face didn’t help either.
She took the cap off once more and packed up her laptop for the night, tomorrow was the big meeting with the prospective client and she had some shopping to do tonight.
* * *
Donna sat in the conference room, uncomfortable in the tight jeans and t-shirt, let alone the cap that adorned her head.
“So as you can see Mr. Tulley, we’re the best management firm in the industry and I’ll be your personal account manager.” she said as she finished her presentation and a smile crossed Ron Tulley’s lips.
Her own smile broadened in response as she knew she’d hooked him.
“I think you’ve won me over Donna. Send over the paperwork to my lawyer and let’s get this done.”
“Absolutely Mr. Tulley, you won’t regret this.” she said, extending her hand as they shook on the deal.
“Great, now let’s go out and celebrate, I’ve got a reservation at Leonards for 12:30, I insist you come with us.” he said and she eagerly agreed, Leonards was the hardest restaurant to get in to in the entire city.
* * *
It was almost 4pm when she returned to the office and she collapsed in to her chair, stuffed full or food and wine as she’d chatted up her client for hours over lunch. But she’d landed him and that was what was important.
Her hands reached up and touched the brim of the cap to take it off, but they hesitated for a moment. Over the last few hours she’d forgotten she was even wearing the thing and now, for some reason, she felt like she should leave it on.
She shook her head from side to side, no, that was silly, she had to get the paper work over to his lawyer and she could very well walk around the office in it. It was bad enough she didn’t have a change of clothes!
* * *
Donna looked over at the credenza by the door where the baseball cap was and her stomach did back flips as the TV blared in the background. She scunched her forehead until she finally stood up, walked over to it and placed it on her head.
A great sigh of relief escaped from between her lips as a smile crossed her lips as she walked back to the couch and flopped down.
The rest of the night flew by and before she knew it she woke up the next morning having fallen asleep on the couch.
* * *
Donna’s fingers shook as she set the cap down on the credenza, she had to go in to work, she couldn’t wear it in could she? No, that was ridiculous, it was just a baseball cap, she could go 8 hours without wearing it!
It had been over a week since Mr. Tulley had signed the paperwork and she’d had several more meetings with him, each time she’d worn the cap, but today she didn’t have any meetings with him so she had to leave it at home.
It was strange, because she’d found herself wearing it more and more at night as well. And now that she was wearing her usual business suit, it felt… wrong somehow. Like her skin was crawling just at the touch of the garment.
She forced herself to open her condo door and leave it behind.
* * *
She’d last almost all the way to lunch before she’d made an excuse and headed home. Her fingers had touched the cap and suddenly everything had felt right.
She’d spent the rest of the day taking conference calls at home and doing work on her computer until she’d headed out to the gym before dinner.
She’d had a gym membership for years, and even used it a few times, but over the last few weeks she’d been going every other day and something in the back of her mind told her that she’d been soon going every day.
Over the next few weeks she either worked from home or had taken the cap with her so she could wear it in her office with her door closed between meetings and over lunch.
At the same time, she had started to find herself masturbating much more often that she had been. It wasn’t like she was some prude or anything, she often masturbated once or twice a week, but recently it had become 3 or 4 times a week and last week it had been every day.
Each time she’d lay in bed, the cap on her head, her naked form wriggling under the ministrations of her fingers or the pounding of her trusty dildo until she came.
But today for some reason, the need had come to her mid way through the afternoon. She knew she wouldn’t last until she arrived at home, so instead she’d closed her door, put the cap on and pushed her fingers under her skirt to find releif. And it came with a mind blowing orgasm that she barely managed to stop herself from screaming out for all the office to hear.
* * *
“Ms. Stevens? Mr. Tulley is here to see you.” Donna’s assistant said over the phone as Donna was sliding the dildo in and out of her pussy.
“Yes… yes… send him in…” she replied breathlessly as she tried to stop masturbating but found it impossible.
Ron opened the door to see the look of passion on her face and quietly closed it behind him as smile crossed his face.
“How are you feeling Donna?” he asked.
“I… I… I’m… so… so… horny!” she said, trying to keep her voice down.
“Yes, yes I’m sure you are by now.” he replied as he walked around behind her desk and stood beside her.
“Tell me Donna, would you like me to help you with that?” he asked as he reached down and placed his thumb on her lower lip, instinctively Donna wrapped her lips around it and suck on it, nodding her agreement.
Ron popped his thumb from her mouth and unbuckled his pants, letting the fall to the floor and exposing his hardening shaft.
Donna’s eyes widened as she dover for it but Ron’s hand stopped her short of her goal.
“Just a moment Donna, don’t want to knock that cap off do you?” he asked rhetorically as her stare was firmly affix to his manhood, “After all there’s a lot of tech in the sweatbands of that hat, wouldn’t want to damage it or anything.”
Ron took hold of the cap and rotated it around backwards so the brim was no longer in the way and release her head from his grip.
Donna’s lips wrapped around him and she dove all the way down to the base of his dick as waves of pleasure coursed through her.
* * *
Donna stepped in to the living room from the porch as Ron entered the room, “Hi baby, have you got that big hard cock for me?” she asked as she held the brim of the cap and rotated it around backwards as she stood naked in front of him.
Just the sight of him made her pussy sopping wet, she’d do anything to get it inside of her.
It had been that way ever since that day in her old office, she’d suck Ron’s cock for a while until he finally bent her over her own desk and pounded her pussy until a rush of orgasms had crashed over her.
After that Ron had told her to quit her job and she’d been happy to do so.
Spend more time at the gym? Of course.
Go to his plastic seurgeon for a consult on some new tits? Sure.
Stay at home and walk around naked all day? What could be better!
Each time he’d fucked her and the orgasms had pushed back any doubts she’d had.
Now she was quite happy to be his “piece of ass in this city” as he called her and couldn’t wait for his visits.