Annie Kirk Ch. 04

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Note: the Annie Kirk series is not a sequential story. The series is comprised of separate fantasies about a real person. Some of the stories were inspired by an erotic photograph she sent where I created a story around the image. Other stories are inspired by real-life elements, but they are not descriptions of real events. This story was inspired by a pair of black stilettos.


The sound of her heels echoed off the marble tile as she made her way to the elevator. Stopping at the alcove, Anny saw the bag she left a little more than an hour ago. She was relieved it was still there. She removed her white sneakers and workout shorts. Leaning against the wall, she stepped into her shorts, removed her “come fuck me” shoes and slipped on her sneakers. She touched her left breast and felt the folded bills slipped into her bra. She reached in, removed and counted five crisp $100 dollar bills. She smiled, he insisted on remaining in character, even the money. A quick stop on the way down and she quickly made her way down the hall, to the lobby and out the front door. She tipped the doorman and the valet before getting in her car and driving home.

Twelve hours earlier

Her phone rang and she heard him. The sound of his voice always brought a smile to her face and made her heart race. She was expecting his call, the fantasy was about to begin.

“I called the agency, gave them a description of what I was looking for, and what I wanted, they said you would be perfect,” he said.

“Thank you Mr. _____?” She said as a question to find out who she was talking to.

“You can call me Sir. That’s all you need to know,” he answered firmly.

“Okay, Sir.” “I will be happy to take care of you.” “Please tell me what you are looking for.” Even though they were role playing, she was nervous. He hadn’t told her what he wanted to do. Just that she would be an escort for him.

“I want someone that will do exactly what I tell them to do. Without question, or hesitation. Can you do that?”

“Yes Sir. I will do everything you ask.” Her mind was racing with thoughts of what he might have her do. It didn’t matter though because she would do anything to make him happy.

“Very good,” he answered. He sounded pleased with her willingness. “You must follow these directions—wear the shortest cocktail dress you can legally wear in public; wear the highest heels you have. I’m sure you know the type, “come fuck me shoes,” and arrive at my hotel room at 9:00 a.m. casino siteleri Do not be late. Can you do that?”

“Yes Sir. I will be there at 9:00, as you asked.”

“Very good,” he said. “I will look forward to seeing you then. Don’t be late,” he instructed and then hung up.

Her excitement was growing. She had to be at his door in 11 hours. She went to her closet and pulled out her six inch black stilettos. Fingers sliding along the hangers until she stopped at the red cocktail dress. It was tight and form fitting, and barely covered her ass. She bought it for a Halloween party several years back and hadn’t worn it since. She hoped it still fit.

Slipping it off the padded hanger she pulled the dress over her head and pulled it down. She was shocked at how short it was. She had a little more than an inch to spare before her ass or pussy would be in view. She stepped into the shoes and inspected herself in the mirror. “This should work,” she said to herself, pleased. She thought her appearance would make him happy. Getting to the room in this outfit was another issue.

Her alarm went off at 7, but she was already awake. The excitement and anticipation made it hard to sleep. She would be powered by adrenaline this morning. Shower, makeup, getting dressed took an hour and fifteen minutes. The drive to the hotel was 30 minutes so she had plenty of time.

She stepped out of the car and handed the keys to the valet at 8:45. The valet didn’t give her a second look. Nor did the doorman as he held the door for her. “Good morning ma’am, welcome to the Omni” was all he said.

She needed to make a quick stop on the way to the room. She found a secluded alcove on the way. She quickly removed her running shoes and top. She pulled the red dress from her bag and slid it over head and pulled it down. She removed her joggers, and stepped into her heels. She placed her clothes in the bag and hid it in the alcove behind a large vase. She hoped it would still be there when she left.

She knocked on the door at 8:59. “If you’re on time, you’re late,” she remembered him telling her before. She hoped 8:59 was early.

He opened the door and took his time inspecting her appearance. She could tell he was pleased, and after several seconds, he said, “very nice.” “I think you will do just fine.” Stepping aside, he said, “please, come in.” He showed her the $500 and placed it on the nightstand. This is for you when we’re done.

She was a bundle of nerves. Obviously she had never been a prostitute before. She couldn’t recall canlı casino ever fantasizing about being one. But here she was, in this man’s room, getting paid to let him do whatever he wanted to her.

“Come over here and get on your knees,” he said. She responded immediately. She struggled a little with the six-inch heels, but quickly dropped to her knees in from of him. She reached out to unbuckle his pants.

“Did I tell you to do that?” he barked at her.

“No Sir, you didn’t. I just thought…”

He cut her off, “I didn’t tell you to think. I said to do what you’re told. Are you going to have a hard time with that?”

“No Sir, I’m sorry. I just want to please you,” she said, eyes looking down to the floor. She felt she had upset him.

Kneeling and waiting for further instructions he walked around her. “This dress is perfect,” and as he spoke, she could feel his hands sliding up the back of her legs and cupping her ass. He slid the dress above her ass. She felt the sting before hearing the sound of his hand crashing down on her ass. SMACK. Letting out a whimper she recoiled against the swat, and then a second spank, on her other cheek. She could feel the sting and burn left behind by his hand. It made her pussy tingle and she could feel the wetness forming on her lips.

He slid his finger between her swollen pussy lips. “You’re getting wet, you like that, don’t you?” He asked.

“Yes Sir. I do.”

“Next time, just ask me to spank you then. You don’t have to disobey me. I will be happy to paddle your ass for you.”

“Yes Sir. Thank you Sir.”

“Now, open my pants and suck me.”

She eagerly unzipped his pants, he was already hard so his cock popped out into her face. She hungrily engulfed his cock with her mouth, swirling her tongue around the head. She alternated between long slow strokes and playfully running her tongue the length of his shaft. She was exploring his cock with her tongue and could tell that he was enjoying it. After several minutes he grabbed her head and, slowly at first, started fucking her mouth. He picked up the pace and as he did he went deeper and deeper into mouth. She could feel him at her throat and it almost made her gag. His cock was coated in her saliva, which was dripping down her chin and onto her chest. When it seemed like he was about to cum he pulled out. She inhaled deeply to catch her breath.

He left her kneeing there. She didn’t dare move. He walked up to her and smacked his cock against her cheek. “Get up please,” he asked. “I want you to lay kaçak casino on the bed, head at the foot, hanging down.”

She did as instructed. Everything was upside down. Her dress was around her hips, her wet and swollen pussy exposed. He slid the dress down from her shoulders over her tits, exposing them too. With her dress gathered around her waist, she laid there waiting for further direction.

She felt his touch as he stroked her nipples. Tweaking and squeezing them getting them hard. He played with her nipple with one hand and reached down to play with her clit with the other. She closed her eyes and let the passion course through her body. Her nipples and clit were communicating with signals of pleasure. Her hips starting rocking. She felt it approaching. It was coming fast and hard. He knew it too because didn’t let up. The only change was he was now straddling her face. He placed the tip of his cock at her mouth, she opened her lips and he slid in. Her head tipped back, she was lost in the approaching orgasm, she could do nothing but let him stroke in and out of her opened mouth.

His cock was sliding deep in her mouth, with her at the edge of orgasm she could barely breathe and then it hit. She squeezed her eyes shut and tried to scream but his cock in her throat muffled the sound. She couldn’t believe she was having a monster orgasm while having her face fucked at the same time.

It seemed to go on and on. He slid his cock out of her throat and stood her up facing the bed. On six inch heels she was wobbly but they placed her at the perfect position. He slid his cock inside her and grabbed both her wrists. She was bent over, balancing and he was using her arms to thrust into her. They had made love many times, but this was just fucking. She wasn’t sure if she was having another orgasm or whether it was a continuation of the first. He fucked her pussy hard, driving deep inside of her. She could see on the clock it was almost 10. He made several hard thrusts and then she could feel his cock throbbing inside of her, shooting stream after stream of his cum in her.

He let go of her wrists and she fell on the bed. “You were amazing Anny. Exactly what I was looking for. I will tell the agency that you were perfect. The $500 is yours. You can take it, get dressed and leave.”

With that, he turned and walked into the bathroom where she heard the shower turn on.

She slipped her dress over her head, stuffed the money into her bra and walked out making her way quickly to the alcove. She was relieved to see her bag still there.

At 10:30 a.m., she pulled into her garage, turned off the car, and stared at herself in the rear-view mirror. She smiled. She couldn’t wait to talk to him about what just happened. She hoped he was pleased.

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