Author’s note: This is part three of Adventures of Jamie, and her first appearance on Wicked Wednesday. As a writer, Jamie is a funny character as much as people will have fantasies about different things I have always found the actual writing very clinical…however, for some reason, Jamie is a huge turn on to create.
How the hell did I get here? Jamie thought with a slight grin. The grin, however, was quickly washed away as her hair was tugged hard yanking her head back. Thanks to this, she stared at the softening erection presenting itself for inspection that had just erupted with warm semen all over her face. She was lucky that it avoided her eyes.
The erection belonged to a fellow whose name she did not know. He was before her with his knees on the bed and enjoying the situation with a large smile and blue eyes staring down through his thick black-rimmed glasses…and using his superior reach with a handful of her brunette curls wrapped in his fist.
Without words, she opened her mouth and sucked in the quickly softening cock to his appreciative groans.
She had been on her way home from Blonde-Vince’s place…where she had left her friend Kirsten after last night’s threesome. A wonderful adventure, but being both Vince and Kirsten were single, Jamie felt it was time to let them get to know each other while she returned to her vanilla life.
At least that was the plan. However, Jamie still had four days until Vanilla-Brad, her husband, came home from his business trip.
She had been sitting on the streetcar, minding her own business…but dammit, she looked good in her tight jeans, lace black boots with the four-inch heels, and black leather jacket over her tight red sweater. Yes, same clothes as last night, but it was not as though she had brought a change. She had brought a refresh in make-up and a brush, though.
The streetcar rumbled on through the afternoon rush-hour traffic along King Street West. This was the busiest streetcar in the city and was often subject to a political push to bury the line and turn it into a subway. Today, however, as was usual it crawled along in the newly cooled fall temperature.
Okay, she had stayed with Vince and Kirsten most of the day, but with some really good orgasms involved, who would blame her? It was not as though she had a scheduled work day to get home for…certain advantages to being a professional fiction writer in that deadlines were not usually confined to specific business hours. In fact, much of her erotic writing came after Vanilla-Brad had fallen asleep and she was feeling a fantasy that needed to be shared.
A tall young man sat beside her on the streetcar. His thick black-rimmed glasses kept slipping down his nose, which he continually chased back with his fingers. His black suit was well pressed with a white shirt and red tie beneath. He failed miserably at attempting to check Jamie out discreetly.
Jamie grinned at him as the attention amused her.
First signs of dusk appeared in front of the streetcar as it continued along westbound.
They flirted playfully for a few blocks with eye glances, Jamie twirling her hair and his hand “accidentally” brushing her leg. He pulled out a business card and pen. He quickly scrawled something on the back of it. Standing up he pulled the bell cord and looked down at her.
Jamie gave him a wide “goodbye” smile…or so she thought.
He handed her the card.
Surprised, she took it from him and watched him slip off the streetcar before reading it. On one side was the blank card for a local five-star hotel. She knew where the place was…very posh and not far from here. On the other side of the card, barely legible in black pen scribble it read, “Please wear those boots, a black skirt and no underwear. Whatever it costs. Room 2004.”
She stifled a giggle. I look like a hooker, she thought.
Later, as her head snapped back from the hair pull, she was enjoying being treated like one.
She had been surprised to find herself standing at the big oak door of the hotel room having not given in to her first instinct to crumple the card up…nor her second, after getting off the streetcar, to throw it out in one of the curb-side garbage bins. Instead, as instructed, she wore the same lace-up black boots with four-inch heels but over stockings held up by her garter belt She had also changed into a black knee-length skirt that hugged her hips tightly below her purple scoop neck blouse with a short black jacket overtop that always made her feel like a waiter. A short nap and shower also helped recharge. Her knuckles rapped lightly on the large oak door.
His thick glasses were the first thing she saw as he opened the door. He had a tight hunter green t-shirt and black slacks. His smile was coy, but his eyes showed his surprise at her arrival. “I wasn’t sure you’d come.”
Behind him, Sting sang about not putting the red light on which almost made Jamie laugh. “How could I say no?”
He pulled the door back to allow her entrance. He then handed her a white envelope and stepped down the hallway. “Can I get you a drink? Red or white wine?”
Her voice answered deeply, “Red would be perfect.” She stopped and looked in the envelope to find ten crisp one-hundred dollar bills. Butterflies in her belly erupted in excitement. Gift horse, she thought as she slipped it into her purse. This would help pay for the website upgrade she was working on.
She then followed into the living area where he was pouring the drinks at the small table in the corner. She stood beside the table looking out the large window from 20 storeys up. “What a gorgeous view.”
He placed the glass of red beside her. “Thank you.”
She picked up the glass and sipped. The butterflies in her belly fluttered again as she felt her skirt being pulled upwards. Being the boot heels were four inches, she simply spread her legs, turned to lean forward onto the table and could not wait to feel what he did next.
He did not disappoint as, somehow very quietly he had unzipped. He slowly eased his erect penis into her as though he were holstering his gun.
She watched the city lights twinkle with his hands on her hips and his cock grinding slowly into her, lifting her up to tip toes, even with the heels. For a long time the only sounds from either of them were light grunts and groans until she felt the first warmth of his cum filling her pussy…something that she would feel often through the evening.
That had been the beginning of the evening and now she was on the bed laying on her belly between his legs and looking at his erection. It was not as impressive as either of the hockey players’ nor Blonde-Vince’s had been…but he had some girth to him. It was also still soaked in her own pussy juices.
His staying power certainly impressed Jamie. She had caught sight of a family picture on top of his suitcase as he fucked her over it…him…a cute chubby blonde woman…and two small children…she figured that he was not quite getting what he needed from his current lifestyle. But tonight, feeling like the hooker she was portraying, that was not her business…it was making for good research, though.
Yes, he had her hair and yes he was above her…but she knew she had all the power. She kissed the tip, just the tip, allowing her lips to flare, sucking the remaining cum from the tip as her tongue could explored the hole she found in the end of it. With one hand and knees holding her up, she cupped the balls with her available hand.
“Oh fuck, yeah…”
Opening her lips further she slipped them over the penis and sucked it in deep. Maybe it was his youth, but even after his having just cum, she knew he would harden Agassi quickly and loved the feeling of him hardening in her mouth. This time, she took him so deep that it was a fight not to gag. Tears began to flow from her eyes. In defiance, she sucked him harder and even deeper until the head of his cock was down her throat when he tensed and came for the third time filling her mouth once again…and she did not miss a single drop.
The clock read just after midnight…four hours after the first time she had felt his cum between her legs…and she hugged him in the hall, feeling his erection once more and wishing she could play with it again.
“Thank you,” he whispered. “How do I see you when I’m in town again?”
Her first instinct was to simply say that he could not…but once again to her surprise she quickly found a pen and scrap of paper in her purse where she scribbled down her cell number. She was getting very good at ignoring instincts.
One last kiss and he handed her two more hundred-dollar bills…a tip.
Down the elevator and out the front of the hotel, the cab they had pre-ordered was waiting for her. She sat in the back, leaned back, and allowed the excitement of what she had just done to fill her. There would be no sleep that night as she wrote the entire story almost per vatim.
It was a story that even Vanilla-Brad thought was a masterpiece of erotic fiction when he read it. A story of a socialite named Jennifer that left her vanilla life and became a hooker, quite by happenstance, for one night while her husband, Carlos, was away. Other than name changes, the only real fiction of the story was that Jennifer only did it once.