Jon was a fool.

He knew he was but accepted it like all his other many foibles. He was a fool in this case because of the young, ginger woman currently in position on the floor of his Red Room. Taryn, that was her name and she was much younger than he had wanted to take on as a submissive. However, she’d been most insistent and quite seductive in how she’d approached him.

They’d met on a website. In and of itself not that unusual, but it had been on an AI art site. Jon had been enjoying the new technology abilities of using his gift with words to translate them into images. Of course, he had to stay within certain bounds or be censured. He kept right to the edge of them and became to be known for it.

Into this situation another artist began to tag him with her creations. They were always ginger young women in various states of undress and she put the most interesting titles or descriptions on them. They began to trade creations, comments, flirts, to the point he finally created a chat room for them to get to know each other. They got to know each other quite well. Taryn told him her real name but didn’t ask for his. She was curious about D/s relationships but never been in one before.

Their second session of chat turned into her begging him to tell her a “story.” He knew what she was asking for but he made sure she knew the rules. She said she did. He began an on-the-cuff story of a young woman who needed to be spanked well for being a brat. Taryn admitted she had bratty tendencies. She responded to his story prompts beautifully and respectfully with “Sir.”

After he described the spanking in detail, over-the-knee and bare bottomed of course, she began to respond with soft, lovely noises and begged for more. His hand kept snapping down onto her firm ass as he turned it into a nice red color. He knew what she must be doing as she read and he hadn’t forbidden it since she wasn’t his submissive anyway. Moving his hand, in the story, he checked to see if she was wet and she assured him she was very wet.

“Did you enjoy being spanked?” He asked.

“Yesss…” She whispered and writhed as he fondled her soft tuft of ginger hair. “Didn’t expect to…” She continued, “but it really turned me on, Sir.”

“Hmm…what should I do about that then?” He asked her. A part of him wondering if she’d actually spanked herself or just imagined it well.

Her eyes turned to him. “Please? Please, Sir? Would you, please, lick me?”

It was rather a bold request to be made so soon, but he was pleased at her progress and natural ability to beg well. He moved her to the chair he’d been sitting on, knowing her bottom was stinging. Slowly, he kissed her inner thighs up to but not yet her mound. He did this on both sides.

“Please, Sir? Please…oh please…more? Please, more?” She begged and whimpered.

“If I do…whose pussy will this become?” He asked.

“Mmm…yours…yours, Sir. I swear it.” She murmured.

“You will not come without permission.” He warned her.

“I know…I won’t, Sir. I promise.” She told him.

At this point, he paused typing the story and wondered if she were just playing along or actually into this but he didn’t care at the moment.

Leaning his head down further, he began to nibble delicately at her folds and lick the juices there. She was very wet and became more so as his tongue went to work.

“Ohhh, Sir…” She responded and hugged his head with her thighs. Her fingers stroked through his hair.

He brought her close to the edge but stopped then blew on the cold wet flesh. She gasped.

“Sir??” She asked. “Please??”

“I am going to bring you close two more times before I let you come, Taryn. It will make it so much more powerful when you do, IF you do, depending on how well you obey now and beg later.” He told her.

“Yes…Sir…I’ll obey.” She hesitated but responded.

Twice more he brought her to the edge and her squeals of pleading became more insistent each time but he stopped just before he knew she’d reach too far.

“Now, beg.” He commanded.

“Mmm….Sir, please, please, finish me…finish me, claim me, make me yours. I’ll obey! I’ll please you. I promise, Sir, just, please…let me come?” She begged softly.

“You may and I do claim you with this.” He told her.

“Yes, yes, I understand. For real, I understand, Sir.” She assured him.

He brought her again to the edge and this time he also reached up to pinch her nipples and twist a little. She cried out and shuddered under him.

“OH YES…YESSSS. OH, SIR! I…I’ve COME!” She sounded surprised at it and he realized she’d never been done this way before through chat and text into an orgasm. Over and over, she kept praising him and thanking him.

He switched back to speaking to her outside of the story and she was still in a daze. He’d only ever known she was indeed over eighteen, although in her country the legal age was lower, for this. Finally, curiosity overcame him and he asked her true age. She quietly admitted she was 23.

For a chat session, for exchanging flirting over images, it was fine that she was so young and, in fact, it was quite flattering. She knew he was much older than her, but she kept going on that she didn’t care. They went on to have other sessions in chat where he claimed other parts of her. It was then she said she wanted to meet him and make this real.

to be continued…