A week had passed since he had Simon’s cock in his mouth when Sally called Peter over to join her in the living room. He came in and sat down across from her. “Peter, I need to teach you how to make up your face so you can amplify your feminine qualities for Simon. I want him to be attracted to you enough to fuck you. I want to watch him fuck you.” Peter felt the blood drain from his face. He had dreaded this conversation. “As you know, she went on, I have been using a larger dildo on you when I have been fucking your ass recently, and you have not objected too much, I think you like it. If I think about it honestly, you have even ejaculated in your cage.” Peter nodded. “It’s you fucking me that I find erotic Ma’am”. This was true. He did like it when she fucked his ass with a strap on. It was very hot to look at his sexy wife sporting a strap on or as he liked to think about it, “A chick dick.” He said to her “I feel like I am your servant. I will do whatever you tell me to. I am here to please you. On the other hand, I am not bisexual. I do not even like men sexually.” “Oh cuck, you fuck him to please me, not you. You know that. And I want to turn you into a great big sissy so he will want to fuck you.” Peter swallowed hard, “Yes ma’am”. “Good boy, now come lick my pussy.” Peter went over and kneeled on the floor in front of her as she spread her legs and pulled her panties down. He ate her pussy till she climaxed. Then she pushed him away and pulled up her panties saying, “here, I have a gift for you.” She reached into her purse and pulled out a little bag.
To read chastity story part 2 click here.
Chastity Continued – Peter’s Story
Peter opened the bag and found a package inside. He opened the package and found a large stainless-steel butt plug with a blue jewel on the end. “Let’s put this in,” she cooed. He sighed and pulled down his pants and pink panties, he turned around and bent over spreading his cheeks for her. She rubbed the plug with some lube she had handy and coaxed the butt plug into his ass. He was pulling up his panties when she said, “I would like you to wear that plug from morning to night. You may remove it before bed.” He sighed again. At the same time, he sort of liked being her play toy. He was lost in thought when she said, “Come sit in front of my mirror so I can teach you how to put on lipstick.” She stood up and walked up stairs with Peter on her heels.
He sat on the bench in front of the mirror and looked at the image. His wife was standing behind him with her hands on his shoulders. She said, “Step one, prep the lips. Ok, watch me.” She walked over to the sink and placed her head under a towel, draped over the sink, with the hot water running below. “The steam moistens and plumps the lips.” She then took the edge of the towel, stretched taunt, and vigorously slid the terry cloth back and forth across her lips. “This exfoliates the lips.”, then She then dabbed her lips dry and applied a smidge of moisturizer to her lips. Next, she applied a lip primer to her lip, making sure to cover all the cherry color of her sumptuous lips. “This primes the lips for the base color and makes it last longer” She then picked up a deep red lip pencil and bent over his shoulder getting close to the mirror and began to trace the outline of her lips. “It is important to start with your lips relaxed and at your ‘Angels Kiss’, here,” as she pointed to the indented crease in the middle of her top lip. “You will need to draw just outside of the upper edge of your color to accentuate your cherry.” He watched awestruck at her deft ability to trace her smile. “You cross the lines into your color at the apex of the cherry kiss and then fill in some heavy lines of the color on the lower lip in the middle and a half inch on each side.” She watched gleefully as he prepared his lips and began to apply his liner. She told him to be careful with this application, and finally, she applied lipstick to the inside edge of her lips and to the fullness of her color. She grabbed a tissue and placed it between my lips and said, “Blot”. I mouthed the tissue several times to remove the excess lipstick. To finish it all off, she applied a little lip gloss to the center of her lower lip and popped her lips up and down against each other to create an eye-catching shine. Peter was baffled. He had no idea that he needed to do so many things to put on lipstick. He had already forgotten most of the steps and so he asked Sally to please write them down for him. She laughed and said “OK” and she went off to find some paper and a pen. He sat there with his cock in its cage and his butt plugged wearing his pink panties under his jeans and he looked in the mirror at himself and then down at the items he needed to master to make himself “attractive enough to fuck.” He laughed at his predicament. His wife came back and said “OK, let’s go through it again, I’ll tell you the steps and you do it for me and I’ll write it down.”
Chastity Continued Peter and Sally
After several trials to get it right on his own, Peter came downstairs with his bright red lips. He sat down beside Sally and pursed them for her. She smiled and said, “Oh you are such a pretty picture cuck!” He shook his head saying, “Thanks” and turned to leave when she said, “Don’t go, we need to do the next thing. With those lips, we need to get you a wig. Peter rolled his eyes. “Come on, let’s go to the wig store.” She got up and purposefully walked to the door. “Like this?” he asked, pointing at his lips. She stopped and looked at him and said, “Well they give you a certain look, let’s keep it on and if you are embarrassed, you can just cover your mouth.” He took a deep breath and said, “Yes ma’am.”
He was quiet in the car, deep in thought as Sally drove. He was thinking about their dynamic and his predicament. He loved being her cuck. Loved it. On the other hand, this forced feminization was not exactly his cup of tea. She clearly liked where things were headed, but he was less enthusiastic. He thought about his butt plug, his cage and his pink panties. He thought about the spanking she gave him over her knee and how he had to stand in the corner, and he thought about sucking Simon’s magnificent cock. He was lost in thought when he was aware that she was parking. He looked up to see they were parked outside a wig store. He was immediately overwhelmed. He said, “I have no idea where to start.” She looked at him kindly and took hold of his hand. “Don’t worry Peter, I have an idea!” They got out of the car, and he held his hand up to his face to cover his red lips as they walked inside. Sally went to the salesclerk and said, “Bring me all the pink curly wigs you have.” The salesgirl went off to the back while they sat in a couple of chairs next to each other with a large mirror to one side. She came back with a pile of boxes and set them on the table. She had not paid Peter any mind till just then when she said “Oh, are these for you?” Looking at Sally, “Or you?” looking at Peter. Peter tapped himself on the chest and said, “This girl.” Sally smiled broadly and giggled a bit, and the salesgirl opened the first box and said, “Come stand in front of the mirror.” She took a bright pink curly haired wig out of the box and put it on Peter’s head. She adjusted it a little here and there and said, “What do you think?” Peter did not know what to think. He turned to look at Sally. She was grinning and said, “Oh my, aren’t you a hottie?” Peter laughed and took another look at his new appearance. He was barely recognizable. Other than the stubble on his face, the pink hair changed him completely. They tried on several other wigs, and in the end went back to the first one that seemed to frame his face best. He even found himself enjoying the experience and he smiled at the image in the mirror. Sally noticed and made a mental note to reward him later.
A Slutty Outfit?
On the way home, Sally said, “Now we need to get you an outfit. A real slutty outfit. We want to dress you like a whore.” Peter gulped. “A whore, really?” She responded, “Yes it’s just playtime Peter and Simon prefers that slutty whorish look.” Peter said nothing for a bit and then said, “Can we talk about Simon?” Sally nodded. Peter thought before he spoke, then he offered “I don’t dislike Simon, but he seemed so dominant.” Sally laughed, and said, “Oh he is, he was on his best behavior when he came over. He didn’t want to scare you.” She chuckled under her breath. She thought for a while and then said “He is good for me. He has a massive cock, he loves to pleasure me, he lets me be myself and he also pushes me sexually. From him, I have learned that I am a ’switch’, I dominate you and I submit to him. He has helped me explore my dominance by guiding me in my interactions with you. He naturally takes control of me in a way that I love. And, Peter, when he is in our home, I want you to respond to him as if he is me. He dominates me and he dominates you. Do you understand?”
Peter thought a long time before he answered. He did not really understand all of what was implied, and he started to speak a few times before he finally said, “I understand what you want. I want to please you. So please help me know if I am pleasing you. I will do whatever you want because I love you and that’s all that matters.” She smiled at him as she looked at his red lips. “He did a good job with that,” she thought.
When they got home, she said to him, “OK, cuck, I want you to strip down to your panties and wear your wig and I want you to go to the bedroom and kneel on the floor for me.”
Using the Hitachi
She came up to find Peter just as she had requested. She went to her chest of drawers and brought out the Hitachi. She plugged it in and told Peter to lay on his back on the bed. She took the Hitachi and she started using it on him just above his cage. She told him to hold onto it and eased the butt plug out of his ass, then she lubed up a finger and looking in his eyes, she eased fingers slowly into his ass. Then she felt for his prostate and found it swollen and full. She used her other hand to handle the Hitachi, taking it away from Peter, she used her finger to stimulate the rigged gland while she moved the Hitachi around Peter’s pelvis. It didn’t take long, and Peter started to climax. He ejaculated all over her hand as she fucked his ass with her fingers. She pulled out his ass, turned off the Hitachi and she presented her hand for Peter to lick clean. She watched him as he eagerly and with exaggerated sensuality as he licked her hand and fingers with his red lips and pink hair, and she was happy. Then she kissed him passionately on the lips. “I love you my sweet plugged cuck.” She held the butt plug aloft and said, “Turn over.” He did and, on his hands and knees, he relaxed so she could insert his plug. “One thing,” she said, “In this position, arch your back and stick your butt out as if I am going to fuck you or spank you. Always do that in this position.” “Yes Ma’am,” he said quietly.
Peter and Sally woke up on a Saturday morning and she nestled into his chest while they chatted. She stroked his cage and balls as they talked. Peter loved these morning weekend rituals, and he was looking forward to fingering and eating his wife out. She was feeling it too. She rolled onto her side and she leaned up against him with his arm around her neck. He held onto her breast, fingering her nipple. At the same time, he used his other hand to spread her legs and finger her pussy. While she was being fingered, she kept a firm grip on his balls. She moaned as he squeezed her nipple and stroked her clit. It did not take her long for her to cum. He continued to stroke her and she began cumming in waves. She suddenly pulled his hand off her pussy and released his balls. She got on her knees and crawled up to his head. She kneeled over his face spreading her knees wide and slowly lowered herself onto his mouth. His tongue lapped at her juicy pussy. She tightly gripped his hair as she began to grind her pussy into his face. She squirted onto his face soaking him and the bed. She then jumped up, heading off to take a shower and saying over her shoulder, “Clean up and meet me downstairs, we have some chores to do.”
Peter stripped and made the bed with fresh sheets. He took a shower, dressed and came downstairs. They sat drinking their coffee and eating cereal for breakfast when Peter asked, “You mentioned chores?” Sally nodded, “Yes, we have some shopping to do.” Peter looked up. She said, “You need heels, a skirt, stockings and a blouse.” Peter gulped. “Really? You want me dressed like that?” “Sweetie, we need to make you into a little slutty gurl so Simon can fuck you for me.” He felt his face flush as he thought about the sinking feeling he had imagined being taken by her Bull. At the same time, knowing that his wife wanted that and that he would be eating her pussy, he felt a little aroused by the idea. He finished eating his breakfast and slowly sipped on his coffee. He sighed. “Ok Ma’am, anything for you.”
They went to a sex shop that had a large selection of slutty clothes and they picked out and tried on various items of clothing. They left with bags filled with all of the items that Sally had referenced, including a pair of 4” heels which really got Peter’s attention. “How the hell am I going to walk in those?” He thought. Sally grabbed his hand and gave it a light squeeze as they neared the car, “We need to have you get used to walking in heels.” He laughed and nodded. When they got home, she told him to put on his lipstick and wig and to put on the short black skirt, mesh stockings and low-cut blouse. She directed him to come downstairs so they could practice in the heels. Peter rolled his eyes and did what he was told. He came down looking quite different than he had ever looked before. He looked like a tramp. Sally said, “Ok… put the boots on.” He took the black boots out of the box and sat on the edge of the couch to put them on. It felt odd to stand in the heels in that they changed his center of gravity. He wobbled as he tried to walk up and down the hallway pretending as if he was on a runway. She stifled a giggle as she watched him struggle with his balance. She said, “I know, why don’t you vacuum the house. That will take your mind off walking.” She jumped to her feet and hurried off to retrieve the vacuum cleaner. She watched him vacuum obediently and was quite turned on. After a while she waved at him to stop and called him over. She rapidly stripped off her panties and said, “Eat my pussy.” He dropped to his knees and with his pink hair and red lips, he ate her out. She had a big orgasm. She pushed him away and said, “Go redo your lipstick and I will meet you at the vanity.”
He was sitting at the vanity looking at himself in the mirror trying to take it all in. She stood behind him and said, “Good work, now we are going to teach you how to do eye shadow.” “First you need to prepare your eyelids with an eye primer.” She applied a bit of primer on her ring finger and gently dabbed until the cream was all absorbed. “It is important you don’t pull on your eyelids, as it causes wrinkles…just dab.” She then applied a bit of concealer to an eye brush and gently swirled it all around her lid and upper brow to the edge of her eyebrow. and she showed him how to do that and then she applied a little powder saying, “This will keep the creasing away.” Next, she took a simple brown eyeshadow, and applied it to her lids, carefully blending it from the middle up and outwards. She then showed him how to apply and blend on his own eyes. She told him to repeat the steps on the other eye. He did a pretty good job in her mind. He looked at himself in the mirror and he started to see the transformation that was taking place. Then she took a clean brush and “polished the look” by making sure to smooth the eye shadow and keep it off his eyebrows. Then she said, “Now for mascara.” She took a mascara brush and carefully drew it up and outward against his eyelashes. As she gave him the brush to do the other eye she said, “This creates a sexy doe eye.” He managed to not put his eye out as he applied the mascara. It was remarkable. She smiled at him and said, “Ok, you look quite cute, and there is much more to learn, but that’s enough for today. Stand up and let me look at you.” Peter stood up and walked around trying not to fall. She giggled and said, “Good.” She looked at him and said, “Tell you what cuck, you get to spend the day in your new look. When then heels become uncomfortable, tell ask me and I will let you take them off.” Peter, almost forlorn said, “Yes Ma’am.”
Chastity Continued to conclusion
She went about her business and was prepping veggies for dinner in the kitchen when she noticed that Peter was not wearing his heels. She thought for a moment and then sternly said “cuck, come here!” He looked up and realized that he had taken off the boots without thinking and he thought “Oh shit!” He hurried over and she opened her mouth to talk when he blurted out “I’m sorry Ma’am, it slipped my mind”. “Sally flushed and said, “Bend over and put your hands on the table, legs apart.” He did what he was told. He dreaded what was to come next. She went through her drawers and found a wooden bread board that had a handle. She stepped behind him and lined up the bread board with his butt. She said firmly, “Count.” He grimaced with what was to come as she pulled his skirt up and his panties down. She took up a good stance and took a couple of practice swings to measure the distance. The bread board felt solid in her hand, and she liked the weight of it. She swung with a solid intent to get his attention. The paddle landed on his butt with a loud thwack taking his breath away. The pain signal rushed to his brain on unmyelinated fibers, arriving just after he heard the sound. He grimaced again and stammered, “1.” Feeling the weight of the board and finding her rhythm she struck him repeatedly as he counted the strokes. “10,” he stammered. His butt was turning red and she kept going. “15,” he said through gritting his teeth. His ass was throbbing, and she stepped back to look at her work. There was her sissy, with her pink hair, black skirt pulled up across her back, white blouse with her panties pulled down to her knees, displaying a very red ass. Peter was softly whimpering, leaning over the table. Sally smiled at the realization that she had succeeded in beginning to sissify him. She was beginning to see her cuck as a gurl. She said, “Ok sweetie, that’s all. Pull your panties up and come give me a hug.” Peter looked so sad with his make-up smeared from his tears. Sally hugged Peter tightly. “I gave you clear instructions and I expect you to adhere to them.” He murmured in agreement and then hugged her tighter for a time. “I’m going to finish the dinner prep sweetie; You go change out of your slutty gear.” Sally cheerfully skipped off to the kitchen and continued to prepare for dinner. Peter could hear her singing to herself. Sally looked up from the sink and noticed Peter was hovering awkwardly. She realized he still had his make-up on. “Oh dear,” she said, “I need to show you how to remove that makeup.”