Turning Cuckold Part 5
Since it was going to take a few weeks for Robert’s sissy clothes to arrive, Mistress Andrea focused her attention on ensuring that he knew how to apply his make-up, and with teaching him how to walk, sit and in general comportment as a sissy boi. Each day she made Robert endure hours of training, correcting any miss-steps with additional practice.
Robert’s sissy clothes arrived at different times since the orders were placed with three different store’s. Upon arrival, Mistress Andrea had Robert check each delivery to ensure that the orders were complete, and once done, had him neatly set them aside. Mistress Andrea wanted to wait until everything had arrived before proceeding with making him begin to wear his prissy sissy clothes’.
On the day that the last shipment arrived, Mistress Andrea had Robert bring all of his new sissy clothes’ to the living room and told him how she wanted them arranged. She then told him to take off his bra and panty so that he could model his new sissy clothes for her. Mistress Andrea purposefully orchestrated the order of the item’s that she wanted him to model so that he would ultimately wind-up dressed in the outfit she wanted him to wear the rest of the day. As he modeled for her, Mistress Andrea photographed him in everything. After the last photo, Robert found himself dressed in a prissy pink and white sissy dress that had ruffle’s, lace trim and a bow in the back. Under his dress was a sissy bra and panty set that was white with little pink bow’s on them. He also wore white anklet sock’s which also had little pink bow’s on them ,and pink Mary Jane shoe’s.
As he stood there Mistress Andrea placed a blond wig on him and attached pretty pink and white ribbon bows to it. “You are absolutely adorable Sissy Robert.” exclaimed Mistress Andrea, adding “Come look and see for yourself.” She lead him by the hand to the full length mirror in his room. “Now, don’t your agree sissy?” She asked. Robert stood starring at himself, resigned enough that he didn’t protest and simply said “Yes Mistress.” Mistress Andrea laughed as she sensed the resignation in his tone. “Go get the camera, load your new pictures onto the computer, and email all of them to Mistress Michelle so she can she how you look. .Make sure sissy that your email is worded properly,” she instructed. “Yes Mistress. “he replied. Robert emailed the pictures and wrote “Mistress Michelle, please find photos of me in my new sissy clothes; I hope that they please you.” When he finished Mistress Andrea had Robert practice walking and sitting in his new outfit.
About an hour later the phone rang and Robert answered it. “Hello.” he said. “Hello Robert, I just loved your adorable picture’s, you do make quite the sissy.” replied Mistress Michelle. “Thank you Mistress,” Robert said. “Kindly put Mistress Andrea on the phone so we may speak.” She instructed. Robert gave his Mistress the phone and stepped out of the room. After speaking briefly with Mistress Michelle, Mistress Andrea told Robert to freshen his lipstick and put a coat of clear lip plumper over it. She also told him to then wait for her in the foyer as she was going to change into some other clothes. As she entered the foyer, Robert was struck by how beautiful Mistress Andrea was. She was dressed in a silk blouse and tailored slacks, and he thought to himself that no matter what she wore she was always stunning.
“Are you going out Mistress?” he asked. “Yes, I am going to meet Mistress Michelle. Oh, and guess what, you’re coming along!” she answered. Robert’s heart immediately began to race and his face flushed with fear. “Please no Mistress, please no,” his voice trembling. “Robert, you can not stay hidden in the house for the rest of your life. There will be errand’s and shopping that need to be done, and you will be doing them. You’re a sissy now and dressed as a girl is the only way you will be. Now, just relax! It is a beautiful day and Mistress Michelle and I have decided we’re going to take the sissy to the park for his first outing,” said Mistress Andrea.
Robert didn’t say anything as they drove to the park, but kept glancing at Mistress Andrea with pleading eyes. Mistress Andrea didn’t acknowledge him, she just smiled knowing the fear that was inside of him. Mistress Michelle had arrived shortly before them and was standing radiantly beside her car. Like Mistress Andrea, she too was stunningly beautiful. When they parked Mistress Andrea said “come on sweetie let’s go.” Robert hesitated wishing that this was only a dream. “I said let’s go,” this time in a harsher tone.
Robert got out of the car and worriedly looked around. “You look even are more adorable than your pictures indicated, Robert,” said Mistress Michelle. ” I just love this outfit, it is so prissy, just perfect for a little sissy boi.” They all walked together to the park entrance and then Mistress Andrea said “sissy, you are to walk about 20 feet ahead of us so that we can watch you, and see other people’s reaction’s.” “Please let me stay by you, please Mistress,” he begged. “You will be fine by yourself; we’ll be near enough and will not let anything happen to my little sissy boi. Off you go sissy,” replied Mistress Andrea.
Robert began to walk and the Mistresses smiled at each other and waited until he was far enough ahead before they followed. Robert was absolutely panicked and clasped his hands as he walked. Mistress Andrea noticed this and called out to him to walk with his wrists limp and daintily to his sides. He did as she said and he began to relax as no one was on the path they were walking down. However, his slight composure changed quickly as they approached the lake area and people were about. He stopped and turned pleading again to his Mistress. “Keep walking sissy and do so as I have taught you. It’s time for everyone to see what a sissy you are,” said Mistress Andrea in a demeaning tone.
Robert walked around the lake subjected to taunts, laughter and even abject disgust by a few. Mistress Andrea and Mistress Michelle enjoyed every moment of his humiliation and planned as they walked the next steps of his sissification.