Sisterhood of Sin -- 14 -- The Courage Jars - Sex Stories

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Sisterhood of Sin -- 14 -- The Courage Jars

Date: 8/7/2017, Categories: Anal, Author: LastWife, Rating: 5, Source: LushStories

plays out and he looks very uncomfortable and anxious. In terms of submission, this is way beyond a short chastity session. It is potentially very humiliating. I have to play this carefully, to choose correctly between Cate Confidence and Sister Cate. I choose Cate Confidence. Maybe I can graduate him to Sister Cate the next time this card comes up. "Sir, I promise I will make this as good as I can for you. I want you to enjoy this. I'm willing to do whatever it takes to make it enjoyable. I can help you prepare. I can wear whatever you want me to wear. I can do whatever you want. You can have as much control as you want." "Do you even have the uh... necessary equipment?" "Yes, Sir. I've never done this with a man, but I have what it takes." I want him to have a mental image of me fucking a woman with a faux cock. "I want to make sure that it isn't too big." "Certainly, Sir." I bring him my strap-on and put it in his hands. He sees that I did not supersize it when I bought it. The dildo is about the same size as his erect cock. My plan is to point out the similarity if he claims it is too big, but he doesn't seem alarmed by it. He also sees that my end of it will penetrate both my pussy and my ass while I'm wearing it. "Where did you get this. I've never seen one like it." "One of the sisters is very creative. She works with metal, wood, plastic, latex, leather, and glass. She also made my chastity belt." He wraps his fingers around the post that goes in my ass. "So you will ... need to prepare, too?" "Yes." I don't like to talk about the cleansing steps, but of course we both go through them. I think that helps ease his anxiety, because we both laugh nervously as we prepare. When we return to the bedroom, I give him a tube of lubricant. "Sir, would you like the honor of fitting this into me?" "Sure." By doing this, I let him penetrate me with the posts that I use to grip and hold my cock. It seems to ease some of his anxiety. He lubricates the anal post and gently pushes it in. The other post slips easily into my pussy, lubricated with my natural juice. I use my anal and vaginal muscles to make my cock move without moving my hips. He seems fascinated by it. I decide not to clip the metal balls on, this time. I don't want to seem too masculine. As he ties the straps behind me, he says, "You're already very wet. You're enjoying this." "Yes, but I'm also very nervous. I don't want to abuse your generosity." "That's a good name for it. My 'generosity'. I'll probably think of this in my ass whenever somebody says generosity in the future. I hope I don't regret it." "I won't give you reason to. I think it is an honor, Sir. Now, do you want me to wear any special clothing?" We're both completely naked and his cock is limp. The difference in size between our cocks makes up for the advantage he has in height and I do feel what Kyra's husband referred to as 'the power of the cock'. "No, Cathy, and you don't need to call me 'Sir'. I think I would like to make ...