Ashley's Good Deal Ch. 03

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Ashley's Good Deal moves into a new chapter.
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Part 3 of the 3 part series

Updated 06/11/2023
Created 07/04/2022
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Ashley Hutchens Was really enjoying the "good deal" she had made Jason Roberts. It has started as a means to an end. Then she had noticed this much older man's performance. He was unlike any lover she'd had before. Next was his generosity. She'd gone from thrift goods clothing to designer labels worth more than her rent. The last, was that she was enjoying herself, and marveled at being able to trust Him, something she'd never experienced before. Maybe it was his age, maybe it was a combination of the age, but Ashley had shocked even herself recently when she had decided to show a portion of herself to this man. She'd often considered and fantasized a kinky lifestyle, and damned if she wasn't on the way to it becoming a reality!

Jason Roberts smiled at the beauty beside him. The open air of the convertible Corvette prevented much conversation, but the way she let him fondle the inside of her thigh and smiled at him told him she was enjoying it. Jason knew that he was incredibly lucky man. The Good Deal had paid tremendous dividends. And when she sent him the pic of the paddle, he was honored to have been selected. He believed her when she told him that she wanted to try it, and as they slowed as they entered the town of Apalach, just before the bridge to St. Georgina/home, they were able to finally talk.

"Now pet, do you remember our rules?"

"Yes Sir, very well. I am to remain naked unless otherwise being provided clothing, and I am not to use furniture unless given permission. I can also say 'WAIT, STOP, YELLOW LIGH or RED LIGHT' at any time to make it all stop."

"Very good pet, good. And you read your book?"

"Yes Sir. The 'BDSM 101' book was very interesting, especially as to the mental aspect. Sir, this is something I've been terribly curious about for the longest time, and that mental part is what I want very much to explore."

"And explore it we will, pet. Since we have been spending time together for almost two months now, we definitely know each other's bodies quite well, so I know you are comfortable there. So I think that when we get there we are going to start off with more than just this collar and leash." As Jason said this, he gave the little leather choker and pet leash a tug, making his pet smile.

"I haven't been spanked since I was seven years old."

"Well, I suspect it's probably been way too long, then," Jason said. "Don't you?"

She didn't reply, but she did smile. In her mind, Ashley Hutchens returned to that last spanking her daddy had given her she was in second grade. She remembered how she squirmed as she was positioned over his lap and spanked. She thought....then pushed it of her mind.

The crossed onto the island in silence. In her mind, Ashley steadied herself. The home was in a gorgeous gated community. As expected of a successful lawyer, it was beachfront, complete with a pool and damn if the place didn't have an elevator too. Ashley almost hit the "1" button in the elevator to return her to the ground floor of the gorgeous house and get herself out of this situation, but at that moment, she realized that her Sir was right. She needed this. And more than that, she wanted this. The idea of surrendering to a man to be punished over his knee made her wet. She stepped out of the elevator as he turned and allowed herself to be led thru the gorgeous, open, and light home. He stopped her at a couch that overlooked the gulf through huge windows. It was late afternoon and the scene was beautiful and serene.

Sir..." she said in a timid voice, "What do I do?" she asked.

"For starters, you probably want to take off those pretty clothes I bought you. We don't want it getting wrinkled through all this, do we?"

Ashley took another deep breath, and then looked down at her feet. Slowly, she reached behind and undid the hooks behind her neck and back. She pulled the shirt over her head and removed her short-shorts, revealing a lacy black pair of panties and a matching bra. Jason stared for a moment, appreciating the view before him. She was embarrassed to be exposed like this to him, and he liked that level of power. But now, knowing that she was going to be spanked by him, Ashley shivered as the pace of her heartbeat quickened a bit. She folded her clothing and placed it over the side arm of the couch, mostly to keep her busy, and to keep her from focusing on the fact that she was now only in her underwear, and that she was about to be spanked like she was a little girl again. At this moment though, she knew that she very much wanted to be spanked, with a spanking hard enough that it would help push her into deep submission.

"Come here," he commanded. Almost as if someone else were controlling her, Ashley felt her foot picking itself up and setting itself down, followed by the other doing the same. It was as if she were helplessly watching herself step over to Jason. "Go ahead and remove your bra," he said.

"Wait," she begged softly. "I-I-I..."

"Yes," he commanded. "You can do this pet, and you will. Now step over here, pet. Good girl...."

At the sound of his calm voice, Ashley felt herself doing at his command, and the bra fell to the floor. She knew she had to do this. She didn't know why. But she had to do it. If she didn't do it now, she would forever wonder what this would have been like. Her nipples immediately reacted to both the temperature and the anticipation of what she thought was about to happen to her.

Jason slightly parted his legs and took the now nearly naked Ashley by the arm. "I'm going to bend you over my knee," he said. "I want you to stand between my legs." She allowed him to guide her into position and then bend her over his left leg, while his right leg held her legs in place as she was bent over.

"That's good pet, good..." Jason cooed. "We can stop right now. I'll only do this if you want to." She immediately stood up and stepped out away from Jason. After she stood for a moment, staring at Him, she felt a wave of warmth, a wave of trust. He looked into her eyes and barely nodded, and she stepped back into place between his legs and allowed him to help position her again.

Ashley suddenly gasped as he placed his hand on the small of her back to balance her and help support her in position, with her elbows on a low ottoman. Her hips were higher than her head, and she was facing then water. The sun was hanging low and the sight was beautiful and serene." "Ashley did not say another word, but she nodded and stared down at the floor below her. She felt her arousal increase as he raised his arm into the air and brought it down quickly. The force of the first swat was unexpected and she gasped aloud. His arm went into the air again and came down on her backside a second time. And a third. A fourth time he struck her, and she called out. Not just from the pain, but from the erotic exhilaration she suddenly felt. Her Sir was right, it did hurt. It wasn't unbearable but it was...oddly....pleasant. He kept his hand on the small of her back as he delivered more strikes in succession. Then, not as rapidly as before, he drew out the intervals between the last four swats.

At last, Jason Roberts spoke. "The point is not to hurt you, even though there is some hurt associated with it. The point is for you to surrender. Fully".

"I get it," she said. "I really do. And I really need to be spanked." Without a word, Jason tugged at the elastic band of her black panties and pulled them away, offering a bare bottom to him for spanking. Ashley turned her head to try to face Jason. "I'm not..." she said, directing her voice behind her towards Jason. But she didn't say anything more, and after a moment, again turned her head towards the floor and waited. Jason began again. This time, flesh made contact with flesh and it stung. A second, third, and fourth blow and the sting became more intense. After the fifth strike, she let out an audible shriek. The pain of the sting was bad, but her conscience also reminded her that she desperately needed this. She needed this more than she had ever been aware. After a bit more, Ashley noticed that the stinging sensation was replaced by a numbing feeling. At that, a great stirring in her belly began.

There was still some pain whenever Jason's hand made contact with her bottom, but there was also, much to Ashley's disbelief, an increasing element of pleasure too. She stopped counting the swats and lost herself in the new feelings she was experiencing. Ashley Hutchens didn't even realize that he had stopped swatting her and was now massaging her pussy instead. He seemed to know exactly what she was feeling, and he seemed to know exactly what to do. In just a few moments, there was a huge sensation like the waves in front of her, and she moaned loudly and squirmed as she came, releasing everything that had been pent up in her. She lay still across his lap, panting hard and not moving, not believing what a powerful experience she had just had. "Can I just lie here for a minute or two?" she asked.

"Yes. For as long as you'd like," Jason responded. Seeing this incredible creature bend to his will was an incredible feeling, something he had not had in many, many years. He waited until her breathing returned to normal. Then she sighed and stood up. "Jason," she began, "that was incredible. How did you know I needed that?" He smiled that little wicked smile of his, the one that no one at the office ever saw, and replied. "Just a hunch."

Ashley then said "When I was across your lap, I felt your cock pressed up against me. It was really hard. Did it turn you on to spank me?" Ashley asked. She smiled as he was momentarily speechless. Ashley Hutchens didn't need nor wait for a response. She kissed her Lover hard, and as she did so, she unzipped and removed his trousers. Pulling that fact cock out of his boxers that she loved so much, she said "Thank you my Sir, You have given me something I have so wanted. Now let me give something to you." With that, she threw a leg over and mounted her Sir, enjoying every bit of the big, fat cock invading and stretching her. She had thought that maybe they could do this for a bit, then some reverse cowgirl, but the time spent learning to work her kegels and the sensation of the moment caught up to her, and presently she felt his fill her womb with glorious spurt after spurt of hot cum.

"That was amazing," he told her.

"So was my spanking that you gave me," she said.

"So you're good to me opening your eyes then?" her Sir asked

"Yes Sir, I am," she replied, then added "This is a good deal indeed Sir, A GOOD Deal indeed."

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