A Chastity Story, continued

Mary welcomed Sally into her office. She closed the door and spoke, “Oh My God Sally, that was incredible on so many levels. You are so damn sexy! Thank you for having me over. I loved it. More importantly, Bill was all in. I have never seen him like that. He purchased me some very sexy lingerie, he pampered me, and then when I got home, he literally ravished me. He sucked Simon’s cum out of my pussy and when I took him out of his cage, he fucked me like we were teenagers again.” Sally laughed and said, “Well that does not surprise me one bit. Isn’t Simon’s cock just huge?” Mary sighed, “Oh man, he is hung!” They chatted about the scene and how hot it was for Mary to experience her first time with a Bull while having her husband’s support. Then she said, “I also loved eating your pussy, kissing you and playing with your great breasts. Listen, the other reason I wanted to chat with you was this, I sort of love how you have made Peter into a sissy. I wanted to know what you think I should pay attention to in order to make my Bill a real sissy?” Mary said she wasn’t sure she was the “right person to guide her”, and she went on, “It was really Simon who started the whole thing. He wanted to fuck a sissy, and I wanted him to desire Peter. I like Simon and I want him to stick around, and Peter was sort of into it. If I am honest, he has always had a softer side.” Mary nodded and asked, “Well can you give me some pointers on what you did?”

Sally Describes How She Sissified her Cuck

Chastity – 11 by SafferMaster
Chastity – 11 by SafferMaster

Sally listed her sissification process, “First I had him wearing ladies’ underwear. Then I taught him how to apply his lipstick and his eye shadow, we are still working on the rest of his face. Then I got him that big pink wig. I also retired his cock and caged him permanently, and I got him a face dildo gag so he uses that to fuck me instead of his cock. I started ass training him and now I am pegging him.  I finished his outfit with a skirt, a blouse, mesh stockings and boots. What I plan on doing next, I’m not 100% certain of, but I think I am going to get him a corset and fake tits.” Mary was taking notes and said, “Wow Sally, you have done way more than I realized. I am not sure if Bill will be into it the way Peter is. Frankly, I was stunned to see Peter sucking Simon’s cock!” “Yes, he has really taken to cock in a way that was quite unexpected and sort of hot as far as I am concerned.”  Mary marveled, “I cannot lie, I am surprised, I have known Peter for years and would never have suspected.” “Simon and 5 of his friends used him the other night when he was all sissied up and he loved it.” Mary’s mouth was open in surprise, she was speechless. Sally said, “Look, I have to go, let me know if you have any more questions.” As Mary walked her to the door she said, “Thanks again Sally, this has changed our lives.”

When Sally left, Mary got on her computer and started to research sissification. She found a few resources and she spent time taking notes. The more time she spent on the site, the more she liked the idea. When she was done a couple of hours later, she sat back to think about Bill and what she would do with him. She called Sally, “Hey Sally, it’s Mary, do you have a quick minute to talk?” “Hey Mary, gosh you are on it!” Mary laughed and said, “I’m inspired! Ok, I have been thinking. I would like to train Bill to be a sissy too, but I want to send him off to be trained for me, if that makes sense. I want to fast track his sissification.” Sally was quiet and then said, “So you really think that is a good idea Mary, I mean what if he doesn’t want to?”

Mary thought for a minute. “I have decided Sally. That is what I want. I’m taking your lead and making our relationship a Female Led Relationship (FLR), that is what I am going to do.” Sally said, “Wait Mary, I think you are moving too fast. You need his consent to do this.” Mary said, “Look, we have been in a very unhappy sexless marriage for far too long. If he wants to stick around, then this is what the currency is.” “I am going to ask you to think about this for a very long time before you take any action, why not do it slower, maybe give him panties to wear, make him wear his cage longer that sort of thing and assess how it is going?” “I mean, you make a fair point if I cared what he thought, but I am feeling very certain about what I want, and I want what I want.”

Sally Introduces Mistress Fiona

“Mary, Peter and I see a professional Dominatrix for training. She is helping us become a better kink couple. She may have some excellent guidance for you about sissification.  Here, let me give you her phone number.” She passed on Mistress Fiona’s contact information and made arrangements with Mary to talk again once Mary had connected with Mistress Fiona.  They said their farewells and hung up.

Sally was pensive. She did not want to be the cause of a breakup between Mary and Bill, and she was intrigued by the conversation about sissy training. She wasn’t fond of the idea of forcing Bill to do something he wasn’t prepared to do, but at the same time, she realized that her sissification of Peter was her own agenda, not his. She was a bit conflicted and thought she should sleep on it.

She went home to find her cuck kneeling at the front door for her. She instructed him to prepare for his daily spanking and he crawled off to the kitchen. She came in and found him with his trousers down and his panties around his thighs bending over the table. She took the new flogger she had purchased and started flogging his backside asking for a number count from time to time as his butt reddened and her arm tired. When she was satisfied, she said, “Toilet.” And followed Peter who was only wearing his panties now to the toilet. She watched him obediently lean back over the toilet and she admired his obedience and discipline to do exactly as she said with just a word. She pulled her panties off and squatted over his open mouth. She pressed her pussy against his lips and relieved herself. “Clean.” She barked. Peter slid off the toilet and turned around to clean his Mistress. She spread her legs for him and basked in the pleasure he gave her.

Chastity – 11 by SafferMaster
Chastity – 11 by SafferMaster

Peter Learns What’s Next

“Come to the kitchen, I want to talk to you,” she said.

In the kitchen, she poured herself a glass of wine and offered Peter some too, He declined. She inhaled deeply, nosing the wine, and then sipped on the table red taking in its earthy tones. She said, “I have been thinking. I am interested in taking your sissification further. I want to know how far you would like to go, or if you are content in leaving it up to me entirely?” Peter bit his lip. “How far are you thinking?” he softly asked. She cocked her head to one side and thought for a minute. “Mary is going to send Bill to sissification training. You are already quite far along. I was thinking of having you start taking female hormones to help your shape. I am going to get you a corset to help make your waist thinner.” Peter took a deep breath. He looked intently at Sally. His mind was running a million miles an hour. “I am not sure Mistress. I love you and I trust you. I have never been happier than I am now, but what will it mean for me to be a full time sissy? Will you still love me the same way?”

Sally reached for his hand. He was shaking and clearly worried. “My sweet cuck, I love you deeply, and I have learned so much more about you and about me too. I will always love you. I think I just prefer you as a sissy than as a man. I don’t know why exactly, its complicated, but when I watch you suck cock for example, or when I watched Diedre fucking you, I was so turned on. I want us to explore your sissy side fully. It’s very erotic!”

Chastity – 11 by SafferMaster
Chastity – 11 by SafferMaster

Hormone Therapy

Peter nodded. He said, “Look, I am not opposed to being your sissy. I enjoy Simon and I’m glad he is in our life. I want you to feel supported by me completely as you explore your sexual power. I loved when you let me spank and then eat Deidra’s pussy. I loved that you let her fuck my sissy ass. I love that you gave me to Simon and his friends to use. It has been amazing to experience. At the same time, I was still Peter underneath all that. I am worried that I will disappear.” He had tears in his eyes as he was speaking. She took a tighter grip on his hand and leaned forward. “Sweetheart, I love you. You! You will always be Peter. The same sweet man I married. We are exploring a part of you that has not been allowed to flourish. I want to experience all of you!” She smiled at him. “Just like with the panties, makeup and so on, we won’t do everything at once. We will go slower so you can adjust. Go get the tape measure, I want to measure you for a corset. Peter fetched the tape measure from the kitchen drawer. “Take off your shirt.” She measured his chest and waist and wrote down the measurements.

“Tell me about the hormones, how do they work?” Sally spoke softly and looked directly at Peter as she did. She leaned forward and made sure she had his undivided attention. “Hormone therapy, Peter, is designed to alter the secondary sexual characteristics so that you appear more female. The hormones generally have an impact on breast tissue, hairline, fat and muscle distribution. They are called  estrogens, antiandrogens, progesterones and gonadotropin- releasing hormone modulators. These hormonal influences are not permanent – you still are a male – but they will impact the way you appear. To the viewer, you appear to have a more feminine shape. Now we won’t go nuts with this, because there are potentially side effects. We will have to monitor your energy levels, your mood, your appetite and so on. It is my intention to combine this approach with choices in clothing that accentuate your curves and you will see cuck, the sissy in you will come to life.” Peter was quiet. He thought a long time before he said anything. His mouth was dry, so he got up to get a glass of water from the fridge. He poured a tall glass of cold water and took a long sip. He sat down again and looked at her with an inward smile. He said, “Mistress, thank you for seeing me. For taking care of me. For stretching me. Thank you for being so loving and thoughtful and kind. Our life is completely different now that we are in this D/s dynamic, that you are leading our marriage, that you are a Hotwife and that I am your cuck. It’s been nothing short of remarkable. I love it. I will do anything you ask. Your happiness is my reason for living.” With that, Sally stood up and went over to him and leaned over to give him a long passionate kiss. “Of sweetie, you make me so happy. Go upstairs and put on your face dildo, so you can fuck me.” She watched him leave on his hands and knees, and she opened her laptop to order the corset.

The following morning, Deidra came by Peter’s office to say “Hi!” Peter said, “Deidra, can we talk?” She nodded and came in and sat down, Peter got up and closed the door. She looked at him as he sat down. He was staring at her intently. “What is it?” she asked. “Did, or do you find me attractive as a sissy?” He was almost pleading with her to say she did. She smiled broadly and said, “Peter, that was singularly the hottest thing I have ever done. You are not just attractive as a sissy; you are sexy, erotic and naughty. I love you as a sissy and I am hoping Sally will let me play with you two again. That was so much fun.” Peter sighed with relief. He said, “Well, Deidra, Sally is going to push on and take me further.” “Oh Peter,” she said, “I am fully in support. I think you are a cute sissy.  I am always here for you. Please give my best to Sally, I have to run.”

Chastity – 11 by SafferMaster
Chastity – 11 by SafferMaster

Mary Explains Life to Bill

Mary got home in the late afternoon and sat in the living room waiting for Bill to return from the office. He wasn’t far behind her and came in humming. “Hello, my queen!” he chortled as he saw her sitting there. She smiled and waved him over. “Have a seat cuck,” she said, indicating the seat next to her on the couch. He sat down, leaned over and gave her a peck on the cheek that she leaned into. “Bill, my love, I am going to take you in a new direction. Starting today, you will wear the cage all week. Two days on, one day off. Understand?” He gulped. “I guess, but why?” This is what I want, and I want you to start wearing ladies’ underwear.” He raised his eyebrows. “Really? Why?” She smiled at him, “Because I am your queen and I get what I want.” He took a deep breath. He looked down at his feet. She said, “Go get your cage please.” He dutifully got up and went out to get his cage. She sat there wondering if she was doing the right thing. He came down with his cage and handed her the lock. She had the key around her neck, and she unlocked it. He stripped down and she put the cage on while he assisted her holding the pieces together as she slipped the lock on and snapped it shut. “There you are, a good little boy, just the way I like you.” Bill stood there naked other than his cage and said, “Why ladies underwear, I think that’s too far.” “Put some clothes on cuck, let’s go out for dinner and we can talk about it. I have a lot to tell you.” 

They ordered dinner at the local pub, and were sipping their beverages when Bill asked, “What is it you want to tell me?” Mary looked in her beer glass as she thought about how to proceed. She finally said, “I have made the decision to completely feminize you, to send you to sissification training. I want you to be my sissy.” Bill almost spit out his beer. “What?” he said, aggressively raising his voice. “What do you mean?” Sally took a pull of her beer, a Guinness Stout, her favorite, and leaned back as the server delivered their burgers. When the server left, she said, “First of all, we agreed that this would be a FLR. You suggested it; I accepted your offer. I love you and that made sense to me, and it still does. Second, as your “Queen”, as you put it, this is what I want. I want you to be fully feminized and transformed into a sissy for my pleasure. You have never explored your feminine side, which is perhaps why our relationship petered out,  so, I want you to do this for me. If you refuse, cuck, it’s simply a deal breaker.” She let that hang in the air, then said, “That is what I want, and I will not take ‘no’ for an answer.” The blood drained from Bill’s face. He was speechless. She was giving him an ultimatum. It seemed unfair. It seemed extreme. He felt a lot of resistance and at the same time, he was a little turned on by her dominance. He liked her to be direct and forceful, it made him feel like she was leading him the way he needed her to lead him. He also processed in those minutes how much more alive he felt as a cuck, especially while wearing his cock cage. He took a deep breath. “Mary, I am at a loss. I don’t know what to say.” She swallowed a bite of her burger noticing that he had not taken a bite of his. She said, “Eat Bill. Look, just say you will go along with me on this.” He took a bite and slowly chewed, and swallowed, then said, “For now, I will say yes, OK, but I am not convinced.” She smiled at him and said, “Bill, you will see. I am going to turn you into a beautiful sissy slut. It will be fun and sexy.” He sighed and they ate in silence.

Big Black Cock

The following day, Mary sent Bill a message saying she was going to be home late since she had a date with a new Bull. This excited Bill and he felt himself experiencing the excitement about being able to clean her out later. He had taken the initiative to go to the store to buy ladies lingerie and had been wearing them all day. He was excited to show Mary. He immediately hoped that she let the Bull cum in her pussy. She sent Sally a message. It read “Sally, I have a date with a Bull!” Sally called her immediately, “Tell me everything?” Mary laughed and said, “I met him online and we texted a few times. He is hung, but not like Simon, he seems nice, he is a banker.” Sally sighed. She said, “Mary, you have to manage STI’s. Until you know this person is not a carrier, you have to use a condom.” Mary agreed, “Yes, I know, I am excited though. Two new lovers in a short time after 10 years with that bore!” Sally laughed at Mary’s excitement. “Play the long game Mary!”

That evening could not come fast enough for Mary. She went to the store and purchased new sexy lingerie. She got changed in the bathroom at the office, and carefully put on her makeup and looked in the bathroom mirror at her appearance. She approved of what she saw. She was not thrilled about the dress she was wearing, but she reasoned, “I’ll be out of it soon enough.” She turned on her heel and went downstairs.

She called an Uber and got dropped off at the front of the hotel. She walked into the bar and scanned the room. It was not very busy, so she quickly picked out her date. She confidently walked up to the single black man sitting at the bar and tapped him on the shoulder. He turned with a big smile. He was devilishly handsome and smelled great. He leaned over to give her a kiss on the cheek. “Nice to meet you Clive,” said Mary.

They talked for a minute and Clive said, “I have a room. They walked arm in arm to the elevator. On route, Clive asked the steward to send up a bottle of chilled champagne. In the elevator, Clive kissed Mary firmly and passionately on the mouth. She melted into his arms and returned the kiss. She was very aroused.  She reached down to his crotch and started to fondle his hardening cock. He was clearly hung and much bigger than her husband’s tiny cock. She smiled inwardly given her mouth was occupied. They arrived at the floor, and they walked hand in hand to the door. He opened the door and they entered. As the door closed, she dropped to her knees and undid his belt and zipper. His pants dropped to his thighs, and she pulled his boxers down. His massive thick cock sprung out and she immediately started sucking his cock. She was deep throating him when there was a knock at the door. She stopped and he pulled up his pants. She went to the bathroom. She stripped down to her lingerie. She touched up her make up and when she heard the door close, she stepped out in her lingerie and heels. She knew that she looked ‘hot to trot’.

Clive poured two glasses of champagne and handed her one. “You look like a million bucks” he said. “To us!” They clicked glasses, she took a quick sip, then put her glass down and said, “Where was I?” She immediately dropped to her knees attacking his belt again. He assisted and got undressed quickly taking his shirt off as his cock disappeared down her throat. He held the back of her head and face fucked her till he was about to cum. He pulled out and picked her up at the shoulders bringing her to standing. “You look lovely, now, let’s get you out of your packaging!”  He undid her bra and sat her on the bed. He pulled down her panties and slipped them over her shoes. “I want you to keep your heels on,” he said as he spread her legs and dived into her pussy. He spread her lips to expose her swollen clit and he went to work with his superior oral skills. In no time at all, she was screaming in ecstasy.

He stood up prepared to fuck her and said, “Because it’s our first time Mary, I am going to use a condom, ok with you?” She nodded and waited while he pulled out and fit a condom on his massive cock. She admired his muscular body as  he prepared himself and she noticed that he put a bottle of lube next to the bed. She smiled thinking that she was in for a long night of fucking. He flipped her over and entered her from behind, she loved that feeling of being taken. He simply just fucked the shit out of her. She had orgasm after orgasm, and they were both working up a sweat.

“I’m going to fuck your ass.” He said perfunctorily as he lubed up his cock. “With that?” she asked in fear. He laughed and said, “yes, with this!” he pressed his cock against her ass. She was not used to ass sex since she had not done it in ages. She tried to relax, but he was too big and was moving too fast. “Please go slower,” she said. He backed off. He added more lube to his cock, and he squirted a dollop of lube into her ass. “Lay flat,” he said, “It’s easier that way.” She said, “Let me,” and she kneeled up on all fours and reached back to take his cock. She directed it and eased it into her ass slowly, then they lay down with him able to enter her fully. They locked legs and he fucked her ass to completion. She was surprised at how erotic it was and she experienced one deep G-spot orgasm after another.

When they were done, she said, “Wow, Clive, that was hot. I have never had anal like that” He smiled as they lay together, her head on his chest. He said, “Yes, very. Listen, I have a thing for you. You really turn me on. I want you for myself. Are you seeing other Bulls?”  “Hmmmm,” she sighed, “I think I would like that; you are dreamy.” He said, “I want to see you again soon; can we arrange that?”  “Oh, I think so,” she laughed, “it’s not like you have to twist my arm!” They lay together quietly in the afterglow, when she said, “I need to send my cuck a photo,” Mary got up and went to the bathroom to grab her phone. She came back and licked and stroked his cock till he was hard again. Then she gave him her phone and said smiling, “Take a picture of me with rigid your cock.” She posed and he took several images. She looked through the photos, selected the best one, and sent it off.

At home, Bill heard the text message arrive. He had been pacing the floor feeling trapped in his cage and excited about his wife getting fucked. He loved the feeling of being left out of her sexual escapades. He had been thinking about her decision to sissify him. He was not bought in yet, but he was getting more comfortable with the idea. Then he opened his text message and when he saw his wife, obviously recently fucked with that giant black cock, he felt his heartbeat accelerate appreciably. He said to himself, “I can’t compete with that.”


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