A Chastity Story Continued

A Situation at Work

Peter was at work and had to attend a meeting in a boardroom with a new consultant. He found a seat at the far end of the table with a good view of the screen and the speaker. The speaker’s assistant, a very sexy woman, was sitting across from him. He was challenged by her presence because every time he looked up, she was staring at him. He started to run stories in his head, “Has she seen my panties?” or “Does she know I am wearing a cage?” and so on. He tried to pay attention to the speaker but found his mind wandering and then he would glance over at her, and she was intently staring at him. It was unnerving. 

The meeting ended and Peter made his way out of the meeting room and headed to the bathroom. He was aware that others were walking in that direction, but he ignored them and tried not to think about her. He was surprised that he had such a strong reaction to her. He had not thought about another woman since he had handed Sally his key and she had locked him in his cage. He was not sure how to process what was happening. 

He walked into the men’s room and waited for a stall. He took a stall as it became vacant and sat down to pee. This was his normal experience these days. He looked at the white tiles on the floor trying to find an answer for his interest in this woman.  When he was done, he pulled up his panties and his pants and absent mindedly tucked the back of his shirt into his underwear. He washed his hands and dried them and came out of the restroom to find the woman waiting outside the door. He was shocked. She looked

at him right in the eye, and she said, “I don’t know what it is about you, but I have to have you.” Peter held his hands up and said, ”Look, I am flattered, I’m sure. You are very beautiful and at another time in life, this might have been a good idea, but right now, it’s not possible. I am married, happily married.” She smiled at him and moved closer. She said, “Let’s go into the bathroom, you were the last one out.” Peter backed away, and said, “Stop. Please stop.” She reached down to his groin, and he instinctively backed away, but she grabbed at his cock and a startled look came over her face. Peter blushed. “Please,” he said, “Please stop.” He took advantage of her confusion to turn and hurry off. He was followed by her laughter as she saw his pink panties sticking out of his pants. 

She started asking around and quickly figured out who Peter was. She researched his profiles and found his wife. She looked up Sally and found a way to contact her. She was on a mission. She was a predator and Peter was her prey. Now she knew he was a sissy in a cage and she was elated. 

Peter was freaked out. He didn’t know how to process what had just happened. Nothing like this had ever occurred to him before. It was a first. She laughed at him. He was so embarrassed. At the same time, he was very turned on. He felt his cage tightening around his now erect penis. It had been several days since his last release. He decided to pretend it never happened. Maybe he had imagined the whole thing.  

He was sitting at his desk, working on a complex table when a message popped up on his screen. It was a photo of him from behind with his panties sticking out of his pants. The person who sent it had a screen name he did not recognize, “Deidra”. He scanned his memory and could not recall anyone on the staff by that name. He recognized the photo as coming from this morning’s encounter with that woman as he

walked off. He blanched as the awareness came over him that this was a serious situation. He didn’t want to be outed at work. It was one of his pressing fears. He called Sally. 

Getting Confronted by His Wife

She answered, “This is Sally,” he said, “Mistress, I have a problem.” She was silent while he gathered his thoughts. He went on, “I am afraid that I am going to be outed here at work. Someone took a photo of me after I had inadvertently tucked my shirt into my panties.” Sally said, “OK, cuck, that is not the end of the world. Who is to say what that photo represents?” Peter was silent for a minute. Then he said, “There is more.” Sally said, “What?” Peter could not get the words out and asked, “Could I talk to you later at home?” Sally was busy and so she said, “OK. See you at home. A spanking sounds like just the right way to start that conversation.” Peter thanked her and hung up. He was shaking. He blocked the person sending the message. He left early and went home. He was home several hours before Sally and so he put on his sissy outfit and made his face up as best he could, and he set about cleaning the house. He vacuumed, dusted, and put everything that was out of place back into its rightful place. He was still at it when Sally arrived home. 

She called him down and he came to the living room and kneeled on the floor at her feet. She was in a foul mood and sat on the couch steaming. It took a minute for her to calm down enough to talk to him. “Who is Deidre?” she asked. Peter almost fainted. He was mortified. “That is what I wanted to tell you about, she is an assistant to the speaker who was at our office today. She stared at me the whole time during the presentation. Then when I went to the bathroom after, she followed me and was waiting for me outside. She grabbed my cock and laughed at me as I ran off. Now I know why. She took that picture.” Sally calmed down a bit, but she was still miffed. “I can’t decide if I should punish you or reward you!” she smirked. Peter looked down at her feet. 

“Deidre contacted me cuck. She wants me to let her use you.” She said quietly. Peter felt the blood draining from his face. He felt faint. “I’m considering it,” Sally went on. The room was spinning for Peter. He put a hand on the coffee table to steady himself. “Mistress, can you spank me please?” He asked.  He was desperate to change the subject. How could she consider letting this woman use him? On the other hand, he liked the idea and wasn’t sure what else to say. Sally looked at him and gauged her feelings. She was pretty pent up, and a spanking might not be a good idea right now. She was also processing the data that Mistress Fiona had shared with her and she wanted to try to expand her repertoire as a Top with different implements. She said, “I spent the morning with a professional dominatrix. She had suggested that she coach me with you present so I can learn more about how best to be your Mistress. She put the idea in my head of you being used by other women. This might surprise you, but I find the idea appealing. I was going to share this with you tonight as I have learned a few more things that I want to take on with you too. So, this woman Deidra, if I let her use you, do you think that would satisfy her or will she demand more?” 

Choosing Punishment

Peter looked at the ground. He could not keep up with all that was happening to him or hearing. He shook his head saying, “I don’t know.” He was shaking. He was confused, upset, and excited. He was a mess. “Please Mistress, spank me.” He implored. She nodded and he crawled off the kitchen where he stood and bent over to lean on the table. He had never wanted a spanking as much as he did now. He hoped she would spank him hard. Sally took out the breadboard. She weighed it in her hand. She pulled

his skirt up over his ass and his panties down. She noticed his butt plug. “Good boy!” She thought. She took what she had learned from Fiona into account, and she started hitting Peter lightly with the paddle. 

He was a bit surprised at how softly she was hitting him compared to her previous spankings but was aware that the intensity was increasing. She built the intensity and said to Peter. “Cuck, I want you to think about the spankings occurring on a scale of 1 – 10. I want you to be experiencing this spanking at a 6 or 7. If it gets to a 7 let me know. Where on that scale are we?” She continued to strike his now pink bottom rhythmically. “Fi, fi, five,” he stammered as the strokes kept coming. Sally increased the intensity and he said, “Seven!” She kept the intensity there and continued to hit him hard enough to get a yelp after each strike. She had lost count of how many strokes she had delivered, and his bottom was red. She continued to spank him, trying to calibrate her intensity to his experience. “What number are we on now?” She asked, “Five?” Peter nodded. This was a surprise to Sally who was hitting him harder than she ever had before. She thought, “Wow, there really is something to this calibration idea.” Her arm was tired, and his ass was very red. Peter was tearful when she said, “Toilet.” He crawled off to the toilet, resting his head with his neck on the seat as he leaned back over the toilet. 

Sally came in and pulled her panties off, she pulled her skirt up and squatted over his face. She pressed her pussy hard against his mouth and began to urinate. “Don’t spill a drop cuck.” She said firmly. Peter did as he was told. He felt the hot liquid fill his mouth and he swallowed as fast as he could making sure to press his lips firmly against her so he would not spill a drop. When she was satisfied that she was done, she said, “Clean.” Peter slid off the potty and turned around as she sat down and spread her legs. He licked her pussy clean and kept licking till she climaxed. She stood up and said, “Go to the kitchen.” Peter crawled out of the bathroom and headed back to the kitchen. He was kneeling on the floor, his spine erect, his hands resting palms up on his thighs when Sally returned. She sat in her chair and looked at Peter. He looked like a mess. His mascara was running down his cheeks. She felt a bit sorry for him, but he didn’t seem upset at all. He looked stoned. “Aah, this must be the subspace that Fiona talked about.” She thought. Peter looked at her lovingly. He was aware that while she was spanking him and pissing in his mouth, he had not thought about the events of the day at all. His attention was on his Mistress. She smiled at him, recognizing that loving look and said, I am going to call Deidre back and see what she has in mind. Peters mind snapped to attention. At the same time, he trusted his Mistress. “Yes Mistress,” he said quietly. 

The Other Woman

Chastity – 8 by SafferMaster
Chastity – 8 by SafferMaster

Sally called the number Deidre had given her and she answered, “Hello?” Sally began, “Deidre, this is Sally, Peter’s Mistress.” Diedre laughed and said, “Great, are you going to let me use him?” “Deidre, I don’t know you. I don’t know what you think you have on Peter that would have you make such a demand. And, Deidre, I understand you assaulted him today?” Deidre was quiet. She said, “I’m sorry, I don’t know what came over me, I think it must be pheromones.” “Deidre, do you understand that Peter belongs to me and that I am his Mistress?” It was Deidra’s turn to be quiet. She paused for a long time and said again, “I’m sorry Mistress.” “Deidra, you behaved very aggressively and very inappropriately today. I think you need to be punished. A spanking sounds in order, don’t you agree?” Deidra gulped. “Yes Mistress,” she said quietly. Here is my address Deidra, come over now and receive your spanking.” Deidra wrote down the address and said quietly, “I’ll be there in 20 minutes.” 

Sally said to Peter, “Let’s go upstairs and put on your face.” 

Sally looked at Peter and was happy. He looked so slutty. She heard the doorbell ring and said to Peter, “Go down and kneel in the living room.” He started to crawl down the stairs. When he was in the living room out of sight, she answered the door to find Deirdre standing there. She had long black hair and was wearing a “little black dress” that showed off her curves, she had thigh high boots on that had her looking eye to eye with Sally. She was perhaps 30 years old. Sally looked her up and down disapprovingly. She invited her in and said, “Come into the living room.” Deidre followed Sally into the living room, and she gasped when she saw Peter kneeling there. At first, she didn’t recognize him, but she felt instantly attracted to Peter again and looked quizzically at Sally. Sally pointed at the couch, “Sit.” 

Deidre sat. She looked back and forth from Sally to Peter and back. Her mouth was open in wonder. Sally said to her. “Deidre, first I want you to apologize to Peter for assaulting him today.” Deidre teared up and said, “I’m sorry Peter, I don’t know what came over me. I am so attracted to you I just don’t know why.” She looked at Sally who went on, “Now Deidre, you need to request that to make amends, that you ask me, his Mistress, to spank you appropriately.” “Yes Mistress,” said Deidre. “Mistress, I have been a bad girl and I request that you give me a spanking for assaulting Peter and all that I did this morning.” Sally nodded, and then said, “One more thing, you need to promise to let this drop after tonight.” Deidre nodded, “Yes Mistress, I promise to let this drop after tonight.” Sally looked at Peter. “Are you satisfied with Deidre’s apology?” Peter nodded, and Deidre teared up seeing his sad face. 

Spankee Becomes Spanker

Chastity – 8 by SafferMaster
Chastity – 8 by SafferMaster

Sally said, “Come to the kitchen,” and she walked out with Deidre following and Peter crawling behind her. She bit her lip when she saw the bread board paddle in Sally’s hand. “Lean over the table and put your hands palms down on the table. Do not take your hands off the table till I tell you to,” she said sternly. Looking at Peter, she said, “Stand up.” He stood. She handed him the paddle. Peter took it and looked at her. She gestured toward Deidra’s rear end with her open hand. Peter shook his head. He did not want to spank her. He handed the paddle back. Sally said, “Cuck, she assaulted you. I think it’s only right for you to punish her.” In his ear she whispered, “After you do, I will allow you to pleasure her.” Peter looked at her, and a wry smile crossed his lips. He reached for the paddle. Deidre was tearful. She stayed put and her tears dripped onto the table making a little pool. She was not ready for the first stroke. Peter brought the paddle down on her with a firmness that surprised him. He was not aware of Sally who was seated behind him, with her skirt pulled up and her hand down her panties. She was very aroused watching her sissy spanking this misbehaved slut. Peter brought the paddle down again and again. Deidre was in shock. She was not used to anything like this, and she wailed with each stroke. Her tears flowed freely now. She cried out, “I’m sorry!” over, and over again. Sally was masturbating furiously now, and she came hard with a massive moan that had Peter turn to watch her. He felt good about pleasing his Mistress, and when he looked back, Deidre’s ass was bright red. He put the paddle down and encouraged Deidre to sit down. She tearfully followed his lead. He got on his knees and spread her legs. He pulled her G-string down and spread her lips so her swollen clit popped up. He lowered his lips onto her clit and put his tongue in action, bringing her to a massive orgasm that had her clutching his pink hair. All the while, Sally was stroking her clit watching her sissy eat the slut out, and she was as hot as she had been in a while, which caused her to climax again, this time at about the same time as the slut.  

She pulled her panties up and told Peter, “Go upstairs and wait.” She told Deidre, “It’s time for you to go.” Deidra asked, “Please Mistress, please can I fuck him?” Sally thought for a minute looking at this

now disheveled slut with makeup running down her face. She said, “He is in a cage, so with a strap on you can, yes. Come up stairs.” 

She took Deidre by her hand and led her upstairs. In the bedroom, they found Peter kneeling on the floor. He looked like quite the sissy slut. Sally said, “I have given permission to this naughty slut to fuck your sissy ass.” Peter looked up and smiled at Diedra and to his Mistress he said, “Thank you Mistress.” 

Two Horny Women with Strap-ons

Sally went to her chest of drawers and pulled out two strap-on harnesses with two similar sized quite large dildos. She handed one harness and a dildo to Deidra and said, “Strip, leave your sexy boots on.” Diedra stripped in front of Peter, and she stepped into the strap-on harness with the cock attached. She made adjustments to get it correctly positioned. She put her boots back on and stood in front of Peter looking very sexy. Sally also stripped naked and donned the other harness and cock. “Suck her cock,” said Sally as she made final adjustments to the harness. Peter did his best cock worshiping and Deidra allowed him to service her cock smiling at his efforts. She felt the urge to fuck his face and she held the back of his head while she slowly fucked his face. Peter was gagging with the deep strokes, but his gag reflex was improving, and he was proud of himself. 

Sally lay on the bed and said, “Now come suck your Mistress’s cock slut.” Deidre let go of his head and Peter climbed on the bed with his ass in the air, to suck Sally’s cock. Sally indicted that Deidra should fuck his ass. She took the bottle of lube from Sally and lubed up her cock. She lifted Peter’s skirt and pulled down his panties. She smiled when she saw his pick panties. Then she saw the sparkle of the butt plug. She reached down and pulled the plug from his ass and set it to one side. She kneeled behind Peter and while he was sucking Sally’s cock, she pressed the end of her dildo against his rosy pucker. Peter, feeling the pressure, relaxed his ass and let her enter. He was in heaven. Being fucked by a ‘hot chick’ while he was sucking Sally’s cock was not a scenario he could have imagined would ever have come out of the day. Sally was aroused watching that skinny slut with small tits fuck her sissy while he gagged on her own cock. It was clear that Peter was enjoying himself. She pulled his head off of her cock to hear him moan. “Change positions,” she said looking at Deidre. Now it was her turn to fuck her sissy. Deidra positioned herself at Peter’s head and she gently held his head while Peter sucked her cock. Sally fucked him hard and deep. Peter, feeling the familiar rhythm and depth, had an orgasm squirting his cum all over the place on the bed. Sally told Deidre to get off the bed and then said, “Clean up your mess Cuck.” 

A Slut Fucks a Slut

Deidra got off the bed and Sally said to her, “Come here, bend over, I am going to fuck you.” Deidra did as she was told, and she buried her face in Peter’s ass as he was cleaning up his mess,  while Sally fucked her. She felt herself building to a massive orgasm as she grabbed Peter’s balls and caged cock with one hand and fingered her clit with the other. Sally pounded her pussy relentlessly causing her to scream out in ecstasy as she climaxed. Sally left Deidra in a heap on the bed and told Peter, “Bathroom.” Peter crawled into the bathroom to drink his wife’s piss as Deidra looked on with curiosity. She walked into the bathroom to see Sally relieving herself down Peter’s throat and said, “I need to go too.” When Sally was done and Peter was about to get up to lick Sally clean, Sally said, “Her too.” Deidra squatted over Peter’s face and was about to let go when Sally said, “Press your pussy into his mouth.” She lowered herself onto Peter’s mouth and it took some coaxing for her to allow herself to piss, but when Sally came over

and kissed her full on the lips as she squeezed one nipple hard, she let go. Peter obligingly drank her piss and when Deidra got up, Sally sat down and said, “Clean me then her,” and Peter did as he was told. 

Deidra was getting dressed when Sally said to her, “You are a naughty little slut and I think I might like to have you back again someday. I have your contact information.  I will be in touch.” She went downstairs and soon Peter joined her in the kitchen. They were sitting at the table, when Deidra came downstairs all cleaned up. Sally thought to herself that she had not really looked at her critically before and she noticed that Deidra really looked quite sexy. She examined her thinking to herself, “I didn’t think I would ever do anything like that.” When Deidre left, she said to Peter, “Well that was something.” Peter nodded and said, “Honestly Mistress, it was the hottest thing we have ever done together. I was not expecting that at all.” 

To be continued…

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