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. He complimented me often and when I asked him if he knew my age he said numbers didn’t matter and so I didn’t tell him I was only sixteen. Sometimes he’d ask me to do things because he liked watching me do them. Although he didn’t specify when I should do them, and I didn’t for one minute imagine him sat wherever he was waiting all day I’d do them two or three times for him, maybe more. And when his next email arrived he was always very grateful for me complying.The things he wanted me to do weren’t too odd, so far at least. I enjoyed doing the more unusual ones for him like sliding my fingers inside my bottom because it felt very naughty and I was definitely decidedly curious. It felt good, and I imagined him thinking about his fingers going inside me there as he stroked himself to climax. But mostly it was positions he’d like to see me in. On all fours with my tiny breasts pointing to the bed and my hand between my legs, flat on my front, laid sideways and many more. I knew from.
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