A Chastity Story – Continued

Peter had his sissy outfit on and was kneeling in the bedroom waiting for Simon and Sally to come upstairs. He was sitting in his Nadu pose with his palms facing up resting on his thighs. It was a bit uncomfortable in that pose in his high heels, but he let the heel sit outside of his shins so he could bare it. While he was waiting, he traced the swirls of the pattern in the carpet with his eyes. He imagined that he would have a fun evening and he reminisced on the first time he sucked Simon’s cock. He smiled to himself and then he heard voices. 

To read my previous chastity Story click here.

He was sure that there were more than two voices, but he could not quite tell. He leaned into his listening to try to discern what he was hearing. His heart started to race, and his breathing quickened. He felt himself getting hard in his cage. His ass squeezed around the butt plug. 

Chastity Story – 9
Chastity Story – 9

A Big Surprise

Sally entered the room. She stood in front of Peter looking very sexy and all dolled up in her emerald, green evening attire and 4” heels. Her hair was up, and she looked beautiful. Peter was confused. He started to ask a question, “Mistress?” She held up her hand and said, “I have a special evening planned, I am going to the Ballet with my girlfriends, and I have given you to Simon to use for the evening.” Peter blanched. This was not anything like he had anticipated earlier, when Sally was making up his face to turn him into the real sissy that he was. He was a bit nervous now, and even though he trusted his Mistress completely, he had only been with Simon one time. He asked, “Simon and friends?” Sally nodded, and kissed his forehead, “Have fun sweetie, I’ll be back in a while to join the fun!” Peter sighed. “Shall I wait here then?” he asked. Sally said, “Yes, wait here. Bye!” and with that she left the room. Peter was really nervous now. “Simon and friends,” he thought. After a while he heard the front door open and close and more voices. Now he was almost hyperventilating. He was shaking with nerves. 

Simon came upstairs and entered the room. “Hello, cuck,” he said, “We have a big evening ahead. Sally gave me the evening to play with you, so I have lined up several gents to come over to use you. I think we will have 6 in all, although only 3 of us are here now, so it should be a world of fun!” Peter gasped. “6 men, to use me?” he sputtered. Simon nodded. “Oh my God!” said Peter. Simon took his pants off and his boxers and then his shirt and he stood there in front of Peter with his over-large limp cock. Even limp, it was still a mind-blowingly large cock that was much bigger than Peter’s erect cock, swinging in front of his face. Simon said, “Suck!” and Peter began his evening with Simon’s cock getting hard in his mouth. He was trying not to gag on the cock as it achieved full erection, and his eyes were closed, so he was not aware of the two other men who had entered the room. They both stripped and stood on either side of Peter who, when he opened his eyes, noticed that they were there with slightly chubby cocks. He reached up with each hand and took a cock in each and continued sucking on Simon. One of the men, George, was getting impatient. “Suck my cock slut,” he said urgently, and Peter let go of Simon’s cock to take George’s cock into his mouth. It wasn’t nearly as large as Simon’s, but it was hard, nevertheless. “More long and thin rather than thick,” he thought. George had the back of Peter’s head and was face fucking him while Simon moved to the other side changing places with George. Peter grabbed Simon’s massive cock and beat him off as he sucked on George’s cock. The third man was now getting impatient, and he said, “Come on George, give a fellow a go.” George let go of Peter’s head and he turned toward Larry who had a very thick cock that stretched Peter’s lips painfully. He was beating off Simon and sucking on Larry when George said, “I want to fuck you slut.” Simon then lay on the bed on his back so Peter could suck his cock while he got ass fucked by George. Peter kneeled on the bed ass up, feet hanging off the end and bent forward to deep throat Simon. George pulled Peter’s butt plug out and lubed up his cock. He pressed into Peter’s ass and fucked him vigorously, cumming quickly.  He pulled out and Larry replaced him. Even though gagging with Simon’s fat long cock down his throat he managed to gasp in surprise when Larry stretched his ass out with his even fatter cock. Being air-tight with these two massive cocks inside his mouth and ass was heaven for Peter. He felt himself ejaculate. Larry shot his load into Peter’s ass and Simon ejaculated in Peter’s mouth with such a massive stream that he had cum dribbling down his chin. George said, “I want to spank his sissy ass!” Peter was already in subspace, so he did as he was told and lay across George’s lap. George lifted his skirt and then, with his bare hand, George got Peter squirming as he gave him a vigorous and very hard spanking like none he had ever experienced before. His ass was crimson when he became aware of three other gents standing in the now crowded bedroom. 

“Bend over,” said Simon and Peter scrambled off George’s lap to lay across the end of the bed with his feet on the floor. One of the new men in the room lifted his skirt to see his pink ass with handprints all over it. He laughed and said, “Wow George, you thrashed him!” George laughed as well, saying, “My hand is still sore!” Peter gasped as this new person drove his cock into his ass. He found a cock in front of his face to suck, and he went to work. The two men changed position, and both ejaculated in their new location. With his ass filled with cum and his mouth dribbling cum down his chin, he heard Simon say, “Get naked Cuck and go kneel in the shower.” 

Chastity Story – 9
Chastity Story – 9

Fucked and Now Pissed On

Peter did as he was told. “You first,” Simon said to Milo who was the only man in the room who never fucked Peter. Peter was kneeling in the shower, naked except for his cage and his tattoo, heady from being so soundly fucked and spanked. He was trying to make sense of things when he saw a man standing in front of him with this limp dick about to piss. Spontaneously, Peter opened his mouth.  One by one the men peed on him for what seemed like a long time. He was soaked, head to toe in piss, He had swallowed some and he had tried not to get it in his eyes. One by one the men left, and it was only Simon who remained in the bathroom. 

He said to Peter, “Take a shower Cuck, then come down and tend to me while I wait for Sally.” 

Peter sighed, He pulled off his wet wig, and tossed it on the floor. He turned the shower on and watched as the last of the piss drained off the floor. He was a bit bewildered. First of all, as the water warmed up holding his hand in the stream, he thought about getting gang banged. He was not sure he was prepared to process it. He liked it. He felt dirty and naughty, and it was sort of hot. On the other hand, he was quite a piss slut now and he actually enjoyed the piss shower he had. That was definitely dirty and naughty, and it made him realize how differently he was interacting with himself since he handed Sally his cage. 

He took a long shower and washed off his makeup and cleaned his body off. He stepped out into a room filled with steam and toweled off. He thought about how to dress. His sissy clothes were a mess, so he put them in the laundry hamper, and chose a simple white t-shirt and a pair of shorts. Barefoot he went downstairs to find Simon watching his TV. “Soccer on the telly,” he thought as he heard the commotion. “Can I get you something Simon?” “Yes cuck, pour me a stiff whisky, something with peat.” Peter went to the kitchen and pulled two whisky glasses from the cabinet. He pulled out the Cal Isla 12 and poured both he and Simon a stiff drink. He added a drop of water and carried them both out to the family room.

He handed Simon his whisky and Simon remarked on the aroma, “Smells wonderful cuck, good selection. Did you add some water?” Peter nodded, “Just a drop Simon, I can get you more if you desire.” Simon took a pull on the glass and shook his head, ”No, this is fine, thanks.” 

They sat there in the family room in separate chairs, drinking their aromatic whisky watching football absentmindedly, when Simon said, “Wow cuck, that was quite a scene!” Peter nodded and was silent for a while. He said softly, “Thank you Simon, that was both weird, amazing and sort of mind blowing. I had no idea I would love cock that much! Being a cum slut for you and your friends was sort of sexy in a weird way. I don’t know what will happen next, but I trust Sally and will follow her lead. Thank you for being such a good lover for her. She has grown so much with your attention.” Simon smiled and nodded. They watched the game in silence sipping their whiskys. Simon finished his drink and said, “Well, I’m off, thanks for a great evening cuck!” Peter stood and shook Simon’s hand. He realized that he really liked Simon and was glad that he was part of his life now. “Have a good evening, Simon,” Peter said as he walked him to the door. 

Peter was asleep on the couch when Sally returned home. She turned off the television, kissed him awake and coaxed him to bed where she cuddled up with him and they both fell into a deep sleep.

Peter woke up and took a groggy shower. Sally was not in the bathroom or the bedroom. He dressed and wandered downstairs. He found her reading the paper in the kitchen. “Hello sleepy head,” she said.

“Morning my love, “ answered Peter. “How was the ballet?” Sally looked up and said, “Oh it was amazing, we had such a good time.” Peter poured himself a cup of coffee and spilled a little on the counter. He was wiping up his spill with a sponge when he asked, “Who did you go with?” Sally looked at his back as she answered, “Mary, Celeste, Gretta and Veronica.” He put the sponge back in the rack on the sink and turned around. Sally asked, smiling, “How about you, how was your evening?” Peter looked at her. “Did she know?” he thought. “Well Simon invited about 6 men over to use me. Were you aware of this?” Sally’s smile broadened. “Not exactly,” she said, “mainly, though, I am curious if you had a good time?” Peter looked at the ceiling as he held his cup under the crook of his left shoulder with his arms folded across his chest. He then said, “Surprisingly, yes, it was very bizarre and quite new, and I wasn’t sure what I was in for. I got fucked, spanked, and pissed on by so many men that I was not sure who’s cock I was sucking and who was fucking me. I don’t even know who gave me a very hard over the knee spanking that had me drop into a trance.” Sally was surprised. She had not discussed the details with Simon, although she knew he had invited a few friends over. “I’m glad sweetie, I want you to explore your sexuality fully.” Peter laughed and said, “Oh, I am.” 

Meeting a Pro Domme

“I hope you have the energy for more though,” she said, “I want to introduce you to someone special today.” Peter raised his eyebrows and took a long pull on his coffee. She went on, “I met Mistress Fiona recently and she is the one who has been helping me with how I manage the spanking that I give you every day. Well, I want you to come with me to her dungeon so she can guide me with you in person.” Peter felt his stomach turn a somersault. He tried to speak. “Mist, Mist, Mistress Fiona?” Sally nodded. “Her dungeon?” Again, Sally nodded. “I’m not going to lie Mistress; I am a little afraid.” Sally stood up and came over to give him a hug. “I love you my sweet cuck, nothing bad is going to happen. This is as much for me as it is for you. It’s so we can be a better kink couple.” She nuzzled herself into his neck kissing him sweetly. She said, “Be a good boy and I will milk you when we get home.” 

Chastity Story – 9
Chastity Story – 9

Consent and Aftercare

When they knocked on the door, it opened, and Peter met Mistress Fiona for the first time. She was dressed just as he expected a Dominatrix to be dressed. She had a tight black latex catsuit on with tall thigh high boots with 4-inch heels. She was wearing an eye mask that hid her features and she had bright red lipstick on. She had long back latex gloves. She looked amazing. She literally took his breath away. “Come on in,” she whispered. Peter was surprised as he and Sally stepped into the front office. It was not anything like he had expected. Sally laughed at his confusion, and said, “The dungeon is in the back.” Fiona unlocked and opened the door into the dungeon and Peter blinked as his eyes adjusted to the red light in the dark space. He made out several objects and his eye settled on the wall of spanking implements. He was trying to imagine what would come next when he felt Fiona take his hand and lead him to the bed. “Sit down.” She said and both he and Sally sat on the bed. Looking at Peter she said. “First, you will address me as Mistress. Is that understood?” “Yes Mistress.” Said Peter. “Good boy, now, are you here of your own free will?” “Yes Mistress.”  “Sally has asked me to help her learn how to use various implements in impact play on you. Do you understand and agree to this?” “Yes Mistress.” “OK, first of all I want you to strip.” Peter looked at Sally, who nodded. Peter stood up and stripped down to his cage. “Good boy,” said Fiona. “Come.” She took Peter by the hand and led him over to a darker area of the room and Peter finally saw a large St Andrews Cross on the wall. He gulped. She felt his resistance and said, “I need your consent to tie you to the cross.” “Yes Mistress, you have my consent,” he mumbled. “Good boy, now put your hands here, and your feet here and here,” indicating with her foot where his feet should be placed. “I am now going to tie you to the cross with rope. Do I have your consent?” Peter nodded, not wanting to share the fear he was feeling out loud. “I cannot hear you cuck,” said Fiona. “Yes Mistress, thank you Mistress.” 

Sally watched with awe as Fiona expertly bound both his arms and legs to the St Andrews Cross. Peter was as vulnerable as he could be. “Right,” said Fiona, “Let’s begin with the light flogger.” She went and came back with several floggers. She set them on a table nearby and organized them from light to heavy. She picked one up and walked over to Peter. She said into his ear, but loud enough for Sally to hear. “I am going to demonstrate how to use the light flogger cuck, and then Sally will have a go, do I have your consent to proceed?” “Ye, Ye, yes Mistress.” He stammered. 

Sally stepped back and marveled at how comfortable she looked with the flogger in her hand, and thought, “Wow, she is so sexy.” Fiona stepped behind Peter, standing about 3 feet behind him. She whipped the flogger round saying to Sally, “See how I manipulate the flogger with my wrist?” She whisked the flogger in a figure 8 pattern with ease. She said, “The fronds, which we call ‘the fall’, must land on the bottom together, so you need to generate enough force or speed to keep them all together, like this,” and with that she stepped toward Peter and started landing the flogger on his back. She said, “See the forehand lands and then the backhand stroke also lands in about the same spot, which we call ‘the target’, but the fall is all together.” She continued for several strokes and Peter started to feel his back warming up. The flogger was not hurting him at all. Sally was mesmerized by watching this very sexy woman expertly flog her cuck. After a few minutes, she stopped and handed the flogger to Sally, “Right, now you have a go.” Sally felt the weight of the flogger and noticed how the tip of the handle was a bit heavier. She did a few practice strokes in the air trying to emulate Fiona’s ease of movement. Fiona said, “Good, now a little harder to keep the fall together as you swing.” Sally increased the speed of her movement and found that it made everything easier. “OK, Sally, now on your cuck.” 

Sally stepped forward and tentatively started to flog Peter. “Harder Sally,” said Fiona, and Sally increased the tempo, noticing that the fall landed more or less together. She kept at it figuring out how to manipulate her wrist to get the movement just right and in a minute, she felt like she had it. Peter noticed that it felt about the same as Fiona’s effort and he said so. “Oh good,” said Sally. “OK, Sally, now let’s go to a heavier flogger.” Sally stopped and handed the light flogger to Fiona. She stepped in front of Sally and took up station behind Peter once again. She said, “OK, now I am going to use a heavier flogger, do I have your consent cuck?” “Yes, Mistress” said Peter confidently. His initial fear had resolved, and he was enjoying the experience now. He was really appreciative that Sally was learning how to do this correctly. 

Fiona stepped into the flogging and began to rain strokes down on Peter’s back. The flogger was longer and heavier, and the fall landed with a thud much louder than the first flogger. Peter jumped a little with each stroke, but he still found the experience a lot more tolerable than being spanked on his bottom with the wooden paddle. He felt himself drifting into subspace and was really enjoying the flogger when it stopped. “This is a little heavier, so two things, the weight of the handle balances the flogger in your hand, and because it’s heavier, you have to swing it quite a bit harder.” She handed the flogger to Sally. 

Sally was immediately impressed that the flogger was weighted differently, and it took her a few practice throws to find the rhythm of the implement. Fiona said, “As the thrower, you are trying to whip the fall at the right moment so they all land together on the target of the catcher.” Sally nodded and continued to practice with the flogger. She started to get the weight and feel of it and stepped forward to deliver the strikes onto Peter’s now quite red back. She had difficulty keeping the falls together and Fiona urged her, “Faster and harder Sally,” and Sally increased the tempo noting that the falls came together nicely. Peter was jumping with each stroke. Peter was in subspace and feeling the adrenaline that he enjoyed from his spankings. However, this was very different from being spanked with a wooden paddle. He really liked it. 

Fiona said, “OK now it’s time for the heavy flogger.” She took the flogger from Sally and indicated that she should step aside. She traded the flogger she had taken from Sally for a still heavier flogger. She said, “This one is a buffalo hide. It’s quite heavy and it’s super well balanced. She flicked it around with her wrist and Sally felt the air that it moved. She handed it to Sally. The flogger felt heavy and light at the same time, which surprised her. “I see what you mean about the balance,” she said, handing it back. “Alright cuck, I am going to use the heavy flogger, do I have your consent to proceed?” “Yes Mistress,” Peter said confidently. “Also, I want to make sure that I calibrate the intensity to your tolerance. Has Sally introduced you to the number system?” “Yes Mistress.”  “OK, Good, now I don’t want this to occur to you over a level 6 do you understand?” “Yes Mistress.” And finally, if it gets over a 7, please say ‘Yellow’ right away. OK?” “Yes Mistress.”

She started winging the flogger and Peter felt the air that it moved. He relaxed waiting for the first blow to land. He was surprised at the force of the flogger and how it moved his whole body, even though it didn’t hurt as much as he expected. “4 Mistress” he said. She increased the intensity and after a few strokes, he said, “6 Mistress.” Sally marveled at how Fiona was able to increase the intensity by ever so slightly raising the tempo. She was mesmerized. Fiona kept the intensity at the same pace and then Peter said, “5 Mistress”. Fiona increased her tempo again slightly and Peter said, “6 Mistress.” Peter’s back was bright red now and they were in a mesmerizing rhythm. After a few minutes, she stropped and handed the flogger to Sally. Sally swished the flogger around and found that even though it was quite heavy, it was also so well balanced so that she could swing it without much extra effort. She started to

find her rhythm and then stepped toward Peter. She brought the flogger down on his back in a solid figure 8 pattern and had to calibrate her intensity to get the falls to land together. Peter said, “4 Mistress” and Sally tried to move more quickly. She struggled to get the timing right as the falls separated but after a minute, she mastered it and then Peter said, “5 Mistress.” She tried again to increase the intensity and finally Peter said, “6 Mistress”. She worked to keep the intensity there and then Peter said, “5 Mistress” and she realized that she would have to work even harder. Her arm was tiring from the heavy flogger, and she finally stopped and said, “Crickey, that’s harder than you made it look!” Fiona laughed and said, “Well I have had more practice than you,” and to Peter she said, “Cuck, now we are going to paddles, how are you holding up?” Peter said, “I’m doing fine, thank you Mistress.” 

They went on with Sally’s training turning Peter’s butt into a bright red-hot bottom. They used several paddles of different materials and all in all spent a couple of hours between paddles and floggers. When Fiona finally took Peter off the St. Andrew’s Cross, he was shaking and in deep subspace. She said to Sally, “Now we have to provide some aftercare. Your sub could go into shock if we do not warm him up.” She fetched a blanket from the blanket warmer as Sally walked with Peter over to the bed. Fiona wrapped Peter up in the warm blanket and offered him some orange juice out of her little fridge nearby the bed. He gratefully drank it and felt himself calming down as he warmed up and his blood sugar returned to normal. 

Fiona said, “Now we need to do a little debriefing. So Cuck, how was that experience for you?”  They chatted for a while and then Fiona sent Peter to get dressed. She said to Sally, “That went well. Next time we can do some training with bondage.” 

A Cuck’s Reward

When they got home, Sally said to Peter, “Go wait in the bedroom for me.” Peter took himself off. Sally emailed Fiona a thank you note and made an appointment for their next visit. She walked into the bedroom to find Peter kneeling on the floor. She appreciated what a good submissive cuck he was. She wanted to show him how much she appreciated his devotion and obedience this weekend. She said to him, “Lie on the bed.” Peter did as he was told. She crawled onto his chest and leaned over him to kiss him passionately. She said, “I love you so much,” and she kissed his cheeks and his neck. Little by little she unbuttoned his shirt and kissed down his chest. She pulled off her top to reveal her full breasts with her erect nipples and the key dangling from her neck. She made her way down to his tummy and then she undid his belt revealing his pink panties, she smiled. She unzipped his pants and pulled both his pants and his panties down his legs and off.  She then carefully unlocked his cage and took it off with a little difficulty due to his partial erection. He immediately sprung into a full erection and Sally licked his penis all over and sucked on his balls. Peter was beside himself and was trying to avoid ejaculating immediately. She held tightly onto his balls and took his throbbing cock all the way into her mouth and with that Peter ejaculated. She swallowed every drop and crawled up next to him and put her head on his chest. She stroked the hair on his chest as she said, “I love you cuck, I love you so much.” 

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