Andrea
Mistress Andrea had been dating her newest boyfriend Robert for two months. She had met him at a local bar and purposefully seduced him. She was looking for someone to cuckold and had sized up that he might be perfect for that. Robert was average in height and weight, a firm but not overly masculine build, had a soft attractive face, and was rather shy. It was clear that he was easy to seduce, and was very timid around a beautiful woman such as Mistress Andrea. During this period, Andrea had kept the fact that she was a Domme from him, She wanted him to grow more and more infatuated with her which would make cuckolding him all the more enjoyable.
It was a Saturday afternoon and Andrea said to Robert, “sweetie, our plans have changed for tonight we’re not going out.” “Oh”, said Robert, “I thought you really wanted to go to that new restaurant and then for drinks.” “I have something else in mind, it is a surprise.” Just then the door bell rang and Andrea said, “be a dear an answer the door, it should be a friend of mine that you haven’t met yet.” Robert innocently answered the door and let Michelle in. Like Andrea, Michelle was a beautiful woman, and Robert’s shy, timid demeanor immediately came through as all he could muster was a “hello.” He walked her friend into the living room, and said, “guess I’ll leave you alone.” “Andrea responded, “before you do, please be a dear and get us some wine.” Robert brought them some wine and simply smiled as he shyly walked out of the room.
As they sipped some wine Michelle said, “you are right, he is perfect for you to cuckold; he lacks confidence around us and it’s evident that he is infatuated with you.” “We’ll wait a little while and then call him in, I want to start this afternoon while you’re here,” said Mistress Andrea. “I’ve decided that he will be a sissy as well. He has somewhat feminine facial features and his body is firm but not muscle ripped. I’ll start him off with wearing panties. I’ll give him a little time to get used to that then get him into full fem attire and make-up. Once I get him sissified, I will then train him on cock sucking and eating his cum, and when he’s ready fluffing and clean-up. I don’t want to push it too fast as I have no intention of being embarrassed when I make him service my lovers.”
After a second glass of wine, Mistress Andrea called to Robert, when he came into the room she said, “there’s a package on the bed, please get it for me, it has a surprise in it.” “Sure,” he responded. When Robert returned he handed Andrea the package and thinking that the surprise was for Andrea, he began to walk away. “Where are you going?” She said, “the surprise is for you silly.”
Robert meekly turned around and softly smiled standing before them. “Why don’t you kneel, it will make showing you your surprise easier?” she said. He hesitated for a second but did as she directed. Andrea took from the bag several pairs of panties all either in silk, or silk with lace trim in floral’s, pink and white. “What do you think?” she asked. “They are very pretty, they will look very nice on you.” Robert responded, “mmm,” they aren’t for me Robert, they’re for you,” said Mistress Andrea. “For me? What am I going to do with them? He asked. “You’re going to wear them.” she answered. “Wear them, I’m not wearing them!” he said with an indignant tone. “Yes you are, and in fact
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