Point of no Return Pleasing m...

Von Calyp50

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*If you haven't read my weakest point pleasing my master then this story will not make sense. I suggest readi... Mehr

Chapter 1
Chapter 2
Chapter 3
Chapter 4
Chapter 5
Chapter 6
Chapter 7
Chapter 8
Chapter 9
Chapter 10
Chapter 11
Chapter 12
Chapter 13
Chapter 15
Chapter 16
Chapter 17
Chapter 18
Chapter 19
Chapter 20
Chapter 21
Chapter 22
Chapter 23
Chapter 24
Chapter 25
Chapter 26
Chapter 27
Chapter 28
Chapter 29
Chapter 30
Chapter 31
Chapter 32
Chapter 33
Chapter 34
Chapter 35
Chapter 36
Chapter 37
Chapter 38
Chapter 39
Chaper 40
Chapter 41
Chapter 42
Chapter 43

Chapter 14

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Von Calyp50

Olivia knew it was getting late and she wanted to be alone with Ryder but her mom was still here, "Mom how long are you here?" Olivia asked. "I leave tomorrow morning sweetie, I couldn't take a lot of time off because I booked an entire week for your wedding" Grace said. "Oh well that is better anyways I would rather have you here for my wedding" Olivia said. "Me too, but I couldn't miss your birthday and when Ryder offered to fly me here I just had to" Grace said. "Yes Ryder tends to do nice things" Olivia said giving him a quick kiss. "I do try to please my soon to be wife" Ryder said. "Hmm I can't wait to be your wife" Olivia said, "Oh my god go get a room" Lily said. "I just might do that Lily, but you are all still here" Olivia said. Ryder laughed and Parker whispered something into Lily's ear, "I would love too, I guess I will see you another day. Oh and Olivia enjoy your sex" Lily said. Olivia stuck her tongue out at her friend as she left and Ryder pulled her close. "Well my dear I am off to bed, thank you for a lovely day and this book is wonderful. I love you Olivia and happy birthday, Ryder please take good care of her" Grace said. Olivia hugged her, "I love you too mom and he does trust me" Olivia said as her mom walked away into the house. "Do I take good care of you?"  Ryder questioned, "yes sir, and this was the best birthday ever" Olivia said. "I am glad you enjoyed it, shall we go inside my sweet kitten?" Ryder asked her. "Yes please master I can't wait to see what you have planned" Olivia said. "What makes you think I have something planned?" Ryder asked as they walked towards the house, "you always have something planned if I am not mistaken sir, I do recall asking you earlier what you planned on doing about me being cold master" Olivia said. "Hmm well I guess we are going to have to see what tricks we can come up with" Ryder said as they reached the house. 

They walked upstairs into the bedroom, Olivia sat on the bed and Ryder stood above her, "before we start I have something to say sir" Olivia said, "okay kitten I am all ears" Ryder said. "Before we did the show you gave me a choice on whether I wanted this and if I wanted to marry you, do you remember that sir?" Olivia said. "I do yes" Ryder said, "well I have an answer, and I want this and so much more. I loved doing the show it was exciting and scary at the same time, it was a surreal experience. I would love to do it again someday and as far as our relationship goes I never want it to change. I love you so much and everything this relationship has to offer, I can't wait to marry you Ryder and please for me never take this relationship away sir" Olivia said. "Okay kitten I won't but now its my turn, and I need you to strip all your clothes off and get on your knees. I want you to not speak unless I ask you a direct question do you understand?" Ryder said. "Yes master" Olivia said as she stood up and did as he instructed her, "close your eyes kitten and do not open them until I say" Ryder said. Olivia closed her eyes and Ryder pulled her to her feet, and pushed her onto the bed. He cuffed her wrists and ankles spreading her out completely she had no where to go. He used the clover clamps and pulled on the chain making her moan. "Now my sweet kitten open your mouth for me" Ryder said as she did, and he placed a ball gag into her mouth and secured it behind her head. "I realize you can't safe word me but I don't think you will need to since it is your birthday I am not going to do anything that will require one" Ryder said and Olivia nodded but her eyes were still closed. Ryder sat in between her legs. "Open your eyes and look at me kitten" Ryder said, Olivia opened her eyes and loved what she was seeing. Ryder was in position as he pushed his erection into her and used a vibrator on her clit, "You will not cum kitten until I say, if you disobey me there will be consequences do you understand?" Ryder said, Olivia nodded as he thrusted hard and fast causing her to moan, as he fucked her he turned the vibrator on full power and pulled on the nipple clamps chain. This sent a wave of pleasure throughout her entire body and she was ready to climax, Ryder stopped and turned it all off feeling her clench.

Olivia groaned but she didn't want to show him she cared as he started up again, the harder he tugged on the chain the more sensitive her nipples became and she was trying to squirm under him. Ryder flicked her nipples and she groaned again it was insanely sensitive and she loved it even just the slightest touch made her wet. "Oh kitten you like the clamps I can tell" Ryder said, Olivia moaned. Ryder thrusted harder and faster and the vibrator was on full power, Olivia was close to an orgasm, "Not yet kitten hold back for me" Ryder said. It was very hard for her to hold it back and Ryder sensed it as he turned it all off. Olivia rolled her eyes, "Oh kitten you will never learn and just for that there will be no orgasm for you" Ryder said as he pushed hard and came inside her pulling out. "He untied her and she looked at him, "please master"  she said, "No and don't ask me again. I do remember telling you what would happen if you rolled your eyes at me again. This isn't even the half of your punishment, I don't care how mad you get you will never roll your eyes at me again" Ryder said. Olivia tried to recall what he said to her and she couldn't remember she decided not to push her luck. Olivia crawled into bed and tried to cuddle Ryder, "kitten" he said, "master please, I need to cuddle" Olivia said, "you do know what is coming right?" Ryder said. "A punishment of some sort yes master" Olivia said, "you don't remember what I said do you?" Ryder asked her. "No master but I can assume its not good" Olivia said, "you are right its not and you are going to hate me by the end of the day tomorrow but I don't care. At this point I have told you enough how much I hate eye rolls, I feel like this is the only way you will learn not to do it" Ryder said. "I am scared master" Olivia said, "as you should be I will not tolerate it anymore Olivia, you told me you wanted this so tomorrow you will experience your most severe punishment and I expect there to be zero complaints. I will be watching the entire time" Ryder said. "Yes master" Olivia said as she tried to sleep and not worry about what would happen tomorrow.

She knew it was Monday and Ryder would need to go to work, and she couldn't recall what he said would happen. The next morning Ryder woke up just before 6 and went to work out, the view from his gym was beautiful as he let some aggression out doing a boxing workout. When he was done he showered and woke Olivia up, "kitten you have 5 minutes to get up and dressed and to meet me downstairs, the longer you take the more you will suffer today" Ryder said. Olivia opened her eyes and tried to wake up the best she could, and quickly dressed she knew her mom was leaving today. Olivia was super nervous she had no idea what was going to happen, but she walked downstairs and into the kitchen. Mr. Jenkins handed her a coffee and Grace joined them. "How do you take your coffee ma'am" Rose asked her, "black thank you" Grace said, "Grace, I will have Finn take you to the airport and my jet will be waiting for you" Ryder said. "That is extremely kind thank you Ryder, Olivia dear I will see you in 2 weeks for your wedding" Grace said as she hugged her daughter. Olivia hugged her back and she left with Finn who was waiting. "Evan, Olivia is coming with me today we will be dropping her off, Morgan can have the day off she won't be needed" Ryder said. Morgan looked worried but she didn't dare say anything she didn't want to lose her job. Olivia suddenly remembered where he was taking her and she tried to plead with him, "sir please I am sorry" Olivia said, "I don't recall giving you permission to speak" Ryder said, Olivia didn't dare say anything else she was so scared and really hoped he wasn't going to do this. 

"I am ready let's go" Ryder said to Evan as he pulled Olivia behind him she started to cry, "Kitten you brought this upon yourself and I assume the tears are because you remember now" Ryder said. Olivia nodded, "well maybe this will teach you" Ryder said as they pulled up to the club, Ryder entered with Olivia and Drew noticed him it being so early he didn't think it was good. Ryder indicated to Drew to follow him and he did, Ryder needed someone to care for her while he was at work. "Strip" Ryder said, Olivia still crying but she took her dress off and stood before him naked, Ryder cuffed her wrists behind her back and lay her on the table it was very cold, he cuffed her ankles to the floor. He then pulled her arms up and attached them to a chain above her pulling her arms up slightly. "Olivia you will not speak to anyone if you do I will keep you here tomorrow too understood" Ryder said. "Yes master" Olivia said with tears she couldn't believe he was actually going to keep her here for the whole day. "Drew she is to remain in this position until I come get her, I don't care if she is in pain, I also would like water and food brought to her. If she speaks she will be punished further, I am not sure if you are comfortable with this but I give you permission to punish her if you need too" Ryder said. "I will do it if necessary and I will make sure she has water and food. Can I ask what she did?" Drew said, "Tell him what you did Olivia" Ryder said. "I rolled my eyes at you master" Olivia said, "and do I allow that?" Ryder said. "No master" Olivia said with a few more tears, "Take care of her for me Drew, and punish her if you see fit" Ryder said as he left for work. Drew looked to Olivia and said, "I am sorry Olivia, just so you are aware there is a camera in here and Ryder will have access to the feed once I turn it on" Drew said. Olivia didn't reply Ryder told her not to speak and being here for one day was going to be torture enough.

Evan drove them to the office and Ryder didn't say anything as he went to his office, Melanie brought him is coffee. She hovered for a second, "what is it Melanie?" Ryder said, "I am not sure if you will be angry but Kara is here and would like to speak to you sir" Melanie said. "Fine" Ryder said with a bit of anger and Melanie left the room and Kara entered, "this better be good Kara, I am not really in the mood today" Ryder said, "I am hoping I could have a job here sir, I promise I will not come after you or your whatever she is" Kara said. "You had a job that you left, and I am not sure exactly why. Olivia is my fiancée and I will be marrying her in 2 weeks time. I don't give a shit about you and that needs to be made very clear, what makes you think after you quit the job you already had that I would be willing to give you another one?" Ryder said. "I was just hoping sir, I am sorry and I promise I will do my best to work super hard and not come after Olivia" Kara said. "You will work for James, and do whatever he says, Kara you have zero strikes if you do even one thing to piss me off you will be gone understood?" Ryder said. "Yes thank you sir" Kara said as she left the room. She was disappointed that she wouldn't be working for him directly but she found James hot as well and she was happy just to have the job. "Melanie send James to my office" Ryder said. "Yes sir right away" Melanie said, a few second later James was standing in front of him. "James, Kara is your new assistant, I suspect you to make sure she earns her keep. I will not tolerate bullshit from her so I want a progress report at the end of each day" Ryder said. "Yes sir" James said as he left the office, "Kara coffee" James said, "yes sir" Kara said as she made coffee as per Melanie's instructions. Ryder answered emails and checked the camera feed at the club, Olivia was still crying. 

Ryder felt bad but he was not going to tolerate eye rolls anymore and he did warn her that this was going to happen. It was noon and Olivia had been tied up for 4 hours like this her arms were starting to hurt, and she was cold. The room was not exactly warm and the table even though she had been on it for 4 hours was still freezing cold under her. Drew walked into the room, "drink this" he said, Olivia drank from the straw she was thirsty, and she realized she needed to go to the bathroom. She knew she wasn't allowed to speak, she cried again, "Olivia are you okay?" Drew asked her, she shook her head. Drew called Ryder, he felt bad and he figured she needed something and Ryder was the only one she was allowed to speak too. "Drew I am watching the feed, what is wrong?" he answered his phone. "I don't know you are on speaker" Drew said, "Kitten talk to me are you okay?" Ryder asked, "No master I hate this and I need to pee" Olivia said, "Drew can help with the bathroom part but Olivia you brought this upon yourself and you will accept the punishment without complaint. I love you and will see you in a few hours" Ryder said as he hung up. Drew knew he needed to keep her in position and he brought in a portable toilet, "you can go to the bathroom" he said. Olivia was mortified she didn't want too, "Olivia you are not the first sub to get punished like this and we have this set up for a reason, I assure you its not anything I haven't dealt with. If you would feel more comfortable if I left then I will" Drew said as he left the room. Olivia was alone and she had the toilet under her and she was able to go but she hated doing it this way. She was angry at Ryder and she was going to make sure he knew it later. 

Drew came back in a few minutes later with Jade she had a tray of food with her, "Jade you will make sure she eats all of this, and you do not have permission to speak to her, I am watching. if you so much as utter one word I will do the same to you understood" Drew said. "Yes master" Jade said as she sat on the floor in front of Olivia and fed her. Olivia didn't want to eat she was not hungry but she knew Ryder was watching, she had so much anger and sadness inside her she just cried. Olivia finished all her food and Jade gave her more water and left the room, Olivia sighed as she tried to move but she was stuck. Her arms began to ache and she had no idea what time it was. 

Ryder on the other hand was trying to get his work done as he kept an eye on his sub, he called Drew noticing she was uncomfortable. "Hello" Drew answered, "can you adjust her arms to a different position I still want her tied down, but she looks like she is hurting, also add your largest butt plug please" Ryder said. "Of course," Drew said as Ryder hung up, Drew walked into the room and unhooked her arms, and he cuffed them to the floor in front of her. Olivia was relieved her shoulders were aching and this position was more comfortable. Drew was behind her, and he said "This is a present from you master" as he pushed the lubed-up butt plug inside her and it was even colder than the table. Olivia shuddered she really felt this one and she did at least feel a little better that he was watching her. She hated the feeling of being alone, and she just wanted to hold him despite how angry she was at him she missed him. Olivia tried to get through the rest of the day without crying but she just felt so much pain and she was freezing cold. She hated this punishment so much it was worse than when they were in New York, Olivia couldn't get comfortable, and the butt plug was not helping as it was cold too and she just wanted this to be over. 

Ryder was getting ready to leave from work and James handed him the progress report, "she did well today" James said. "Thank you, James, I will see you tomorrow" Ryder said as he left the office, and Evan was waiting for him. "Should I be concerned that Kara is here?" Evan asked, "I don't think so she works for James, and I am keeping an eye on her. I am hoping we won't have any issues I told her that she has zero strikes." Ryder said, "I understand, your mother-in-law landed safely according to Finn" Evan said. "Perfect let's go get Olivia" Ryder said as Evan drove them to the club. Ryder walked inside it was just after 430, "How did she do?" Ryder asked Drew, "she cried most of the day, most subs get angry, but I think she is just became sadder as the day went on" Drew said. "She doesn't like being alone, and I have done this before but never to this extent. She took it hard so I can only imagine how she is feeling right now" Ryder said. "I don't tolerate eye rolls either and Jade knows better, Olivia did well though she didn't break any of your rules" Drew said. "Olivia knows better too and sometimes I don't think she realizes she is doing it, but I did tell her this would happen, and I will not hesitate to do it again" Ryder said. "Well, the dungeon is available to you anytime you need it" Drew said, "thank you and I appreciate you keeping an eye on her" Ryder said. "Anytime" Drew said as Ryder walked away and went to the dungeon. He knelt down in front of Olivia, and she turned her head, "I suspect you are angry with me and that is fine, but I need you to tell me Olivia did you learn something today?" Ryder asked her. "Yes, master I am sorry I rolled my eyes" Olivia said, "I forgive you and I will do this every time you do it. I need an honest answer here kitten will you do it again?" Ryder said, "No master" Olivia said, "good girl, now I was watching you today and I noticed a few things, one you cried all day how are you feeling now?" Ryder asked. "I am upset sir, and sad" Olivia said, "I see and is it directed at me?" Ryder said, "yes sir" Olivia said, "Alright, well I will let you take the lead today but there will be no rule breaking Olivia otherwise I will bring you here tomorrow too" Ryder said as he untied her. Olivia stood up she was grateful to not be on the cold table anymore. 

Ryder took the butt plug out and put it in the bin to be sanitized as he handed Olivia her dress and she followed him out of the room. Olivia so badly wanted him to cuddle her even though she was super angry she craved his touch, they climbed into the McLaren and Evan drove them home. Before Olivia even climbed out of the car she said " Please master let me cuddle you" Olivia said. Ryder pulled her out of the car and hugged her kissing the top of her head as she cried into his chest. "Kitten I really hate punishing you like this but you know how I feel about the eye roll" Ryder said. "I know master and I am sorry" Olivia said, "I know kitten, come on let's go inside" Ryder said as he grabbed her hand and took her inside. Evan went downstairs and Ryder sat on the couch with Olivia he cuddled her trying to calm her down. "Kitten are you good?" Ryder asked her, "no master I am hurting" Olivia said, "Physically or mentally?" Ryder asked, "mentally sir" Olivia said. Ryder kissed the top of her head, and flipped her over so he was on top and she was below him. Ryder kissed her hard and took his pants off, he knew she wasn't wearing any underwear as he pushed his erection into her. Olivia moaned under him she missed him all day and she needed this. Ryder went fast and hard causing Olivia to climax quickly she didn't know if she was allowed to so she tried to hold it back. Ryder could feel her tense up, "let go kitten" Ryder said and Olivia orgasmed hard around him as he also came inside her. "Better?" Ryder asked. "Yes master thank you" Olivia said, "good lets eat then we have something to discuss" Ryder said. Olivia nodded as Ryder went upstairs to change she had no idea what he wanted to discuss but she was nervous. 

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