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Author's Note: Yes, this is fiction, sort of. It is a real fantasy and described as a fantasy - I guess it is non-fiction.:) (Although Hank and Janet might be surprised at that.)
Hank had a weird situation. He was going on a vanilla date with a Domme while cyberly serving one far away. (Yes, they knew of each other.)
It was a usual date except he was in a FemDom chastity device and she understood why he wouldn't try to get in her pants. (For those unfamiliar with it the FemDom is low security. Real low. But if taken off without authorization it was almost impossible to put back on without even a cheap webcam showing he had cheated. It was really all he needed.)
Well, it wasn't typical, but it was vanilla. They split an antipasto and had water. Then they went to her gym.
Over dinner they talked of the usual first date stuff. Hopes, dreams, ex-spouses, alimony, religion, politics, etc. (Did I mention they were both divorced and in their 40s?) He also told her he was entranced by her red hair, but she already knew.
They went to an aerobics class and he did the drunken sumo wrestler when the instructor said, "Grapevine right!" Janet went right and did a grapevine like pro. He was puffing during the tummy crunches, but other than that he actually kept up with her.
Then they tried the ellipticals. She tried level 10 (of 20) with him on the Aerobics workout. He smiled inwardly when she adjusted hers to level 5. She got her revenge when he could not bench press as much as her. She had fun pointing out he could not bench press a third of what she could.
Their conversation went like, "You know, huff, pant, it is a good, huff, huff, breathe, workout when your, grunt, huff, pant, groan, strain, forearms sweat."
Then came time to shower. His cyber Mistress made him practice putting nail pastel pink nail polish on his toes, and the chastity device could be embarrassing naked. She took him to her place so he could use the shower. His fevered mind made much of it. In reality she just showed him where it was and the kissed him on the cheek (face cheek) good night.
His fantasy was better.
In the fantasy she told him to strip because she wanted to see the device.
"I don't think I should do that without permission," he said.
"Good answer," she said then led him to where she kept her computer. She IMed his cyber Mistress with "He wants to know if I have your permission."
"Good," she his Mistress typed. "Is he there?"
"Y" she typed.
"Good, turn on the camera, and, Hank, sugar, she knows what I allow. We exchanged e-mails and stuff. You can't cum, but she might finger herself while you wash her. Oh, she's never seen a FemDom before. I told her she can see mine."
When he finished reading he looked at Janet who said, "OK now, strip."
He stripped and she put a collar and leash on him. "It is OK if the collar gets wet, you won't be in it long. I do want to get soaped up when I shower. Afterwards you can shower yourself."
He soaped her up and thrilled at the sight of her naked body. How long had it been since he saw a real live woman's breast? She noticed his stare and lavishly licked her lips, and said, "I bet you want to get free of that thing?" Then she started caressing his balls.
He fought the building erection. He told his back to arch away from her but his back had other ideas. Like one who can't keep him self from a temptation that is best resisted he got closer to her. He was in Heaven when she pulled the chain and kissed him.
Despite everything he became aroused and tried to arch his back away from the pain. Unfortunately the pain came with him. She then turned around and told him to soap her back. He must've spent too long on her derriere, because she said that her ankles were getting jealous.
She spread her legs to make it easy for him and he looked up to see her fingering her pussy.
"I bet you'd like to lick this?" she said.
Could he say "No?" Was this a test? Did he ask his Mistress permission or assume it was already given? He was relieved when she said it was rhetorical.
"That is not for now," she said. She started rubbing in earnest and pulled his chain up. She turned around, ordered him to hold her and kissed him while pulling tightly on his chain and fingering her self. He had never kissed a woman in the midst of an orgasm before that he knew of. Her mouth was slack, but her tongue was wild like an epileptic having a seizure. Meanwhile she had dropped the leash and was pulling him close by the back of his head.
When she was done she took the collar off him and told him to shower himself now.
When he came out he noticed his gym bag with his spare clothes was nowhere in sight. He toweled off and didn't worry about it. That meant playtime was not over.
"Hank," she said, "You've been very good. I spoke to your Mistress and we agreed. It has been three weeks and you have earned a milking."
He looked at the computer. The webcam was still active. His Mistress's voice came out of the speakers, "I want you tied for this because she will also redden your ass for me," his Mistress said. "You now a smart ass is a red ass, and you are a smart ass. Oh, Yahoo voice and camera does not crash with her system like it does with yours."
Janet tied him bent over the back of a chair and paddled his ass. "You turn red quickly," she said.
"Your workout your arms well," he said.
She hit him again. "I did not give you permission to speak, but thanks." As if to punctuate the first part she hit him again. "Do you understand?"
"Yes, MMMM,ah, Miss Janet" he said.
He heard laughter from Janet and the speakers. Blinders were put on him and he heard the sound of a rubber glove going on a hand. Then he felt his ass get lubed and heard a buzzing sound. It had been along time. He "Oohed and enjoyed it while the vibrator was in him It seemed to bring him close the finish line but the finish line was on one of those things that move the gates for the horses and it kept just out of reach. Then all too soon he felt cum dripping from his flaccid penis. It went into a juice glass.
"I bet you are thirsty from the workout," said Janet.
The computer speakers chuckled.
He didn't really like this part, but that was the point. Janet lifted the glass to his lips and he drank it down. He'd get some juice later and he had a toothbrush in his gym bag.
She the produced his gym bag and untied him. At the door she gave him a peck on the cheek and slapped his ass. "Next week you can run my vacuum cleaner," she said.
Yes, the fantasy was better, he thought as he took the train home.