Monday Again
Chapter 5

Copyright© 2008 by Lady Ilsa

Erotica Sex Story: Chapter 5 - Another chilly Monday, like any other winter's day. Linda's lunch plans are canceled at the last minute, but her husband has something - and someone - else in mind for her afternoon.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   MaleDom   Light Bond   Swinging   Oral Sex   Anal Sex   Sex Toys  

As Jim and Linda lay there, relaxing, he thought back to the conversation he had had with John this morning.

From all the chats with Linda online, he knew that John wanted her to be able to enjoy anal sex as much as he did. John also wanted her to enjoy it with men whose cocks were bigger than his. But Linda was tight. It took a lot for her to be comfortable and enjoy anal penetration. To that end, John had her wear a butt plug for at least 2 hours a day. He had purchased 3 sizes and Linda was just now able to take the medium one easily but still required his help taking the largest.

Linda and John had been exploring her submissive nature for a few months. John would give her instructions to carry out, sexually, and if she obeyed, then she was allowed to cum. If she didn't, she was "punished". She had a list of punishments and it was up to John to pick and choose the appropriate one. The anal training was his top priority.

During the conversation with John, Jim had learned that sometimes Linda didn't follow his instructions. In fact, she had not done her training in 3 days - but Linda didn't know that John knew this. John decided that Jim could administer her 'punishment' today. They had discussed her limits, her expectations and what John would prefer, but it would be Jim's job to see it through. He smiled at the thought because he knew just what she needed - and all their previous conversations on the subject had given him insight into her desires.

"Darling? Did you wear your plug today?", he asked, knowing the answer, as he gently caressed her hip and thigh.

She slowly shoot her head. "No, not today. I wasn't home", she replied as she almost purred at his touch.

"What does being home have to do with it? Didn't John instruct you to wear your plug every day for 2 hours? I don't think he said 'at home only', did he?"

"Well, no, but I can't wear it to the store..."

"Why not? Who would know? Doesn't really matter though, you've been a bad girl and you know what happens when you're bad. You are to be punished for each day you didn't wear it and according to John, that's been 3 days...", he said with an air of authority - cool and calm.

Linda looked at him. How could he know? How could John know? But looking at his face she knew that they had already talked about this and that she was going to be punished. The thought sent a delicious shiver down her spine. What would he do? What would he demand?

"According to your list, you are to receive 10 smacks on the ass for each day of disobedience but I think that may be a bit much, so we're going to modify it a little. First you are going to take MY butt plug and keep it in. Then you are going to pinch your clit while I administer your punishment. If you let go, that will be another punishment. I also think you will need to count for me, only to 10, but I won't use my hand, I like my flogger better." As he said this, he slowly got off the bed, retrieved his toy and looked down at her. She could see that he was serious and that his toy was bigger than any of hers.

He undid one of her ankle straps and turned her onto her stomach. Pulling her hips towards him, he raised her ass into the air. Her legs were spread apart and the ankle strap secured as before. She could feel the coldness of the lube as he spread it over and in her anus, plunging his finger in and out, then slowly inserting two fingers and spreading them apart. The feeling of fullness was very pleasurable to her and she found herself anticipating the plug.

When she was loosened a bit, he lubed up the plug and began to slowly insert it - she couldn't believe how big it felt! At the widest point, she guessed it was just over 2 inches in diameter with the flared portion at over and inch and a half - that would hold her ass open and when withdrawn, leave her loose. After a few minutes, she felt the almost unbearable pressure and then it was in! All of it! She felt like it would split her in two but knew that it wouldn't really.

 
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