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Watcher32 · 08-21-2022, 01:24 PM

Slowly Will began to eat. He was starving. But trying to balance with his ass in the air and eat with one hand made the task a bit difficult. Out of the corner of his eye he caught Alice smirking. Evidently amused at his predicament. He honestly couldn’t blame her. He would be doing the same thing.

The scrambled eggs in particular where being challenging. After a few minutes Alice finally took mercy, throwing a fork down on the floor and kicking it over.

“Thanks” he mumbled around a mouthful of bacon.

“Thanks what?” she asked sharply

Will swallowed. “Thank you mistress.”

“As amusing as it was to watch you. I need you to keep your strength up. As I said I have a great day planned. Now go stack the dishes and pans in the sink. You can wash them later. Then I want you to go freshen up. I am sure your breath stinks.”

Will did as he was told. Brushing his teeth. He then splashed some water in his face to help wake himself up.

He looked himself in the mirror. “Was he enjoying this?” He thought to himself. Somewhat surprised by his own answer. This was a different side to the beautiful woman he knew. He found himself enthralled by her. Maybe his feelings for her ran deeper than he real…

Alice appeared in the doorway two cups of coffee in hand. Shirt barely covering the bottom of her ass., Interrupting his thoughts. He looked over at her. Surprised for so reason to see her in here.

“I hope I’m not interrupting something.” She teased.

“No sorry. Just still waking up.”

“Let’s have a cup of coffee and I’ll explain the next game. I’ll give you a hint. It’s a good thing you don’t mind your face being wet.”

He followed her into the family room where the wine glasses and chest board where still set up from the previous night. She motioned to a chair and he found himself pleasantly surprised to allowed to sit normally.

“So… Mistress… You said something about another game?”

“Yes. One I am VERY excited about. It’s simple. You will be handcuffed and blindfolded under my desk. I am going to play 5 counterstrike matches. If my K/d ratio is under my average for all 5. You get to cum.”

“No catch?”

“No catch she answered. You will have earned yourself an orgasm today.”

Will found himself excited. His balls where aching from the constant stimulation of Alice’s presence and no release. “ and what if you do better than average on any of the matches?”

Alice smiled evilly and her eyes sparkled. “Then you will spend the rest of the weekend wearing this.”

She produced a small metal contraption and placed it on the table. It took will a second to realize what it was.

“Is that…???”

“Yes” she answered simply.

“How long have you…???”

“Oh a while. I have just waiting for the perfect bet. And besides. If you can’t distract me well enough when I have your complete attention, I don’t see any reason you should be able to be.”

Will pondered the chastity cage in front of him. He found himself hoping Alice had some good opponents.

————————

Will found himself blindfolded and handcuffed to the office chair. He had been shoved under the desk on his knees. His back was already killing him from being hunched over. She had put on some noise blocking headphones. Will assumed for when her roommate was home. So unfortunately he wouldn’t be able to hear the game.

Will knew he only had one real way he could distract her. The shapely thighs draped over his shoulders and could feel his nose brushing up against her shaved mound. He felt his chin resting on the towel she had placed over the chair.

He also realized 5 matches could be a long time. He wasn’t sure he could distract her that much. He also REALLY didn’t want to wear that cage. The evil thing had been in the back of his mind the entire set up.

What he could hear was the clicking. If he judged correctly then when the clicking was most, she would be most invested in the game and therefore couldn’t have any distractions.

The fan on the computer next to him began to whine. Indicating the game was starting up.

Will first began teasing her with his nose. Simple but he knew she liked it. Slowly he began to nibble on the inside of her thigh. He was pleased to hear her gasp. He could feel she was dripping wet. Will had to wonder how long this had been one of her fantasies. Clearly she had not come up with the idea on the spot.

He delved deeper with his tongue searching for the spot. She squirmed. Her thighs wrapped around his head. She thrust herself into him. Overhead. Will could hear the clicking had all but stopped. She was sooo close.

Will removed his tongue and started to move his head away. He was only stopped because of the her thighs wrapped around him. In any case it didn’t matter. She wasn’t getting any more stimulation from him.

“That’s right” he thought smiling. “ you just said distract you. Nothing about giving you orgasms.” He could feel her frustration. She seemed to be hitting the keys harder. Clicking with just a bit more force. Will Waited until she sounded like she was playing again before starting again.

———————————-

This had not worked out like Alice had planned. She had expected to lose this dare. But damn had she expected it to be more fun. 7 edges was not what she was hoping for. But she had to give will credit, he had known just how to win this one. He always had been good with his mouth. But this had been unexpectedly frustrating.

The matches where over and she had played horribly. Who wouldn’t have. She carefully got up from the chair. Removing Will’s sweat stained shirt. She was about to grab a robe but thought better of it. Why not let the first thing Will has seen in two hours be her body.

She unlocked the cuffs and moved the chair out of the way. Will removed the blind fold and climbed out. Stretching out his back and legs. His face was absolutely covered in her juices. Smiling triumphantly he looked at her.

“How did I do?”

That smile infuriated her. It was the same smile he always had when he won. For a man who had spent two hours handcuffed under a desk, He had no right to be so self satisfied.

“You won.” she said simply.

Will smiled again “ so how do you want to…?

She cut him off “You have earned your orgasm but there was no agreement of how.”

Wills smile faltered.

“In fact.” She continued. “There is the continuing lack of you referring to me as ‘mistress’.

“But…” be began.

“Not to mention I think you still owe me a few after this. So I have a way we can satisfy all three conditions.”

“I am not sure…” Will began. Nervous now.

“Well you can do it my way Or you can choose the cage.” She smiled sweetly. Besides sweetie. You know how anal I can be about rules.”

Will’s reaction was everything she could have hoped for.

To be continued….

08-21-2022, 01:24 PM	#9
Watcher32 Junior Member Join Date: Mar 2016 Posts: 8	Chapter 5: Never count your Money Slowly Will began to eat. He was starving. But trying to balance with his ass in the air and eat with one hand made the task a bit difficult. Out of the corner of his eye he caught Alice smirking. Evidently amused at his predicament. He honestly couldn’t blame her. He would be doing the same thing. The scrambled eggs in particular where being challenging. After a few minutes Alice finally took mercy, throwing a fork down on the floor and kicking it over. “Thanks” he mumbled around a mouthful of bacon. “Thanks what?” she asked sharply Will swallowed. “Thank you mistress.” “As amusing as it was to watch you. I need you to keep your strength up. As I said I have a great day planned. Now go stack the dishes and pans in the sink. You can wash them later. Then I want you to go freshen up. I am sure your breath stinks.” Will did as he was told. Brushing his teeth. He then splashed some water in his face to help wake himself up. He looked himself in the mirror. “Was he enjoying this?” He thought to himself. Somewhat surprised by his own answer. This was a different side to the beautiful woman he knew. He found himself enthralled by her. Maybe his feelings for her ran deeper than he real… Alice appeared in the doorway two cups of coffee in hand. Shirt barely covering the bottom of her ass., Interrupting his thoughts. He looked over at her. Surprised for so reason to see her in here. “I hope I’m not interrupting something.” She teased. “No sorry. Just still waking up.” “Let’s have a cup of coffee and I’ll explain the next game. I’ll give you a hint. It’s a good thing you don’t mind your face being wet.” He followed her into the family room where the wine glasses and chest board where still set up from the previous night. She motioned to a chair and he found himself pleasantly surprised to allowed to sit normally. “So… Mistress… You said something about another game?” “Yes. One I am VERY excited about. It’s simple. You will be handcuffed and blindfolded under my desk. I am going to play 5 counterstrike matches. If my K/d ratio is under my average for all 5. You get to cum.” “No catch?” “No catch she answered. You will have earned yourself an orgasm today.” Will found himself excited. His balls where aching from the constant stimulation of Alice’s presence and no release. “ and what if you do better than average on any of the matches?” Alice smiled evilly and her eyes sparkled. “Then you will spend the rest of the weekend wearing this.” She produced a small metal contraption and placed it on the table. It took will a second to realize what it was. “Is that…???” “Yes” she answered simply. “How long have you…???” “Oh a while. I have just waiting for the perfect bet. And besides. If you can’t distract me well enough when I have your complete attention, I don’t see any reason you should be able to be.” Will pondered the chastity cage in front of him. He found himself hoping Alice had some good opponents. ———————— Will found himself blindfolded and handcuffed to the office chair. He had been shoved under the desk on his knees. His back was already killing him from being hunched over. She had put on some noise blocking headphones. Will assumed for when her roommate was home. So unfortunately he wouldn’t be able to hear the game. Will knew he only had one real way he could distract her. The shapely thighs draped over his shoulders and could feel his nose brushing up against her shaved mound. He felt his chin resting on the towel she had placed over the chair. He also realized 5 matches could be a long time. He wasn’t sure he could distract her that much. He also REALLY didn’t want to wear that cage. The evil thing had been in the back of his mind the entire set up. What he could hear was the clicking. If he judged correctly then when the clicking was most, she would be most invested in the game and therefore couldn’t have any distractions. The fan on the computer next to him began to whine. Indicating the game was starting up. Will first began teasing her with his nose. Simple but he knew she liked it. Slowly he began to nibble on the inside of her thigh. He was pleased to hear her gasp. He could feel she was dripping wet. Will had to wonder how long this had been one of her fantasies. Clearly she had not come up with the idea on the spot. He delved deeper with his tongue searching for the spot. She squirmed. Her thighs wrapped around his head. She thrust herself into him. Overhead. Will could hear the clicking had all but stopped. She was sooo close. Will removed his tongue and started to move his head away. He was only stopped because of the her thighs wrapped around him. In any case it didn’t matter. She wasn’t getting any more stimulation from him. “That’s right” he thought smiling. “ you just said distract you. Nothing about giving you orgasms.” He could feel her frustration. She seemed to be hitting the keys harder. Clicking with just a bit more force. Will Waited until she sounded like she was playing again before starting again. ———————————- This had not worked out like Alice had planned. She had expected to lose this dare. But damn had she expected it to be more fun. 7 edges was not what she was hoping for. But she had to give will credit, he had known just how to win this one. He always had been good with his mouth. But this had been unexpectedly frustrating. The matches where over and she had played horribly. Who wouldn’t have. She carefully got up from the chair. Removing Will’s sweat stained shirt. She was about to grab a robe but thought better of it. Why not let the first thing Will has seen in two hours be her body. She unlocked the cuffs and moved the chair out of the way. Will removed the blind fold and climbed out. Stretching out his back and legs. His face was absolutely covered in her juices. Smiling triumphantly he looked at her. “How did I do?” That smile infuriated her. It was the same smile he always had when he won. For a man who had spent two hours handcuffed under a desk, He had no right to be so self satisfied. “You won.” she said simply. Will smiled again “ so how do you want to…? She cut him off “You have earned your orgasm but there was no agreement of how.” Wills smile faltered. “In fact.” She continued. “There is the continuing lack of you referring to me as ‘mistress’. “But…” be began. “Not to mention I think you still owe me a few after this. So I have a way we can satisfy all three conditions.” “I am not sure…” Will began. Nervous now. “Well you can do it my way Or you can choose the cage.” She smiled sweetly. Besides sweetie. You know how anal I can be about rules.” Will’s reaction was everything she could have hoped for. To be continued….