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 your going to put the floral panty that is right in front of you on now!" Andrea said in an authoritative tone.

 He stared at her and went to get up and walk away when Andrea said, "before you make the decision to not do what I've told you let me make things very clear for you. If you walk out of this room now without those panties on you better pack-up your clothes and leave, and know that you'll be leaving for good.  Likewise, know that if you put those panties on you will be embarking on a whole new life with me.  I intend on fully feminizing you and making you into my cuckold.  This the only reason why I seduced you in the first place.  I have no interest in you as my lover, you're not man enough for me, but you do have usefulness to serve me as I see fit."  He continued to knell before them in shock from what he had heard, his mind racing with fear and anxiety. "Decide, and decide right now!" ordered Andrea.
He looked at her and then at Michelle who simply smiled.

 He stared at the panties not fully comprehending what this all really meant, and looked up at Andrea again. 
"Decide!" she repeated in an angry tone.  Robert stood up and meekly opened his pants and pulled them off.  He stood for a second again staring down at the panties, hesitating to take off his briefs." Get those off and get the panties on or get the fuck out right now!" Andrea screamed at him. His face grew pale and tears began to run down his cheeks as he took off the briefs and slid the floral panties up over his hips. "Come closer to me!" she ordered. He moved closer and she reached into his panty and pulled his cock and balls back between his legs and then  fixed his panty. "That is the way you are to wear your panties, no male hood showing," said Mistress Andrea. "Now walk a little and turn so we can see how you look." Both women chuckled and gave approving nods." Get those other clothes out of my sight and then come back in here and pour us some more wine. From now on you are to respond to my orders with "Yes, Mistress." "Do you understand?!" she said.  

"Yes Mistress" he responded and hurried teary eyed away.