It was Friday and the last day for Ryder to hopefully be in New York for work, Olivia so badly wanted to spend time with him outside of the office and hotel. She groaned at his alarm as he kissed her head and climbed out of bed. "Master please don't leave me" Olivia said, "kitten we need to get ready for work" Ryder said, "I know but just 5 more minutes please sir" Olivia said. Ryder smiled as he lay back down beside her as he let her take over, "please fuck me master" Olivia said. "I can't say no to that" Ryder said as he pushed her down onto the bed and pushed his erection into her and she moaned. "Always so ready for me, I love it" Ryder said, "I love you master so much" Olivia said. "I love you too my beautiful fiancée" Ryder said as he pushed harder trying to make this quick they really did need to get ready for work. Olivia was getting close, "master please" Olivia said, "cum kitten" Ryder said as she clenched and climaxed around him and so did he, "thank you my sweet kitten, now we need to get ready" Ryder said as he pulled her up and she stood before him. "What is the plan for today sir?" Olivia said, "what makes you think I have a plan?" Ryder said. "You always have one, and I am nervous today sir" Olivia said. "Oh and why is that?" Ryder asked her as he put on his shirt, "well yesterday you said you were going to show Kara who belongs to you and um I am a bit nervous what that means" Olivia said. Ryder laughed, "as you should be kitten, but I promise it will not embarrass you in anyway, I know how you feel about the whole humiliation" Ryder said. "Its growing on me sir" Olivia said. "That is my girl, now put this on" Ryder said as he passed her on outfit, Olivia looked at it and knew immediately that he was going to make her go bra and pantie less. Ryder studied her and said, "is there a problem?" "No sir, it is just well an interesting outfit choice" Olivia said, "it is a sexy outfit choice, and I am in charge remember" Ryder said. "Yes master I remember" Olivia said. "Good girl now can you tell me your rules before we go?" Ryder said, "speak only to you sir unless someone asks me something directly. Do not leave your side, and no complaining sir!" Olivia said. "Oh I have a feeling there will be complaints today but regardless, lets go" Ryder said, "no complaints sir" Olivia said. "We will see about that" Ryder said giving her a wink, Blake and Evan with him this time. Parker was picking up Lily at the airport as she was flying in to go dress shopping with Olivia.
They walked into the office and Kara was there, "Morning sir" Kara said with a smile, Ryder stared at her and then he looked to Olivia, and pushed her against the wall and kissed her hard. Kara looked as if she had been slapped in the face, and Paul laughed, "well must be nice having an assistant like that" he said, "it is, what is on the agenda today Paul?" Ryder said as he and Olivia followed him into the office. "We have everything lined up for the EKG just need a company to run it" Paul said, "send the details over to Green-tech they are expecting it, and are prepared to run the program" Ryder said. "Will do, and the MRI's with the new software are running great and there are no more complications" Paul said. "Perfect, keep building more and I will have them sold here soon" Ryder said knowing he probably had a dozen emails to go through. "Will do" Paul said as he left the office, Kara came in with Ryder's coffee, "thank you Kara, and you will take orders from Olivia today, she is your boss" Ryder said. "Oh um yes sir" Kara said as she left the room. "Really sir?" Olivia said, "yup you deserve to be a little bossy today" Ryder said. "Oh thank you sir!" Olivia said giving him a kiss she was really going to enjoy this. Ryder laughed as he checked his emails, and Olivia thought of her first task for Kara, "want anything from Starbucks sir?" Olivia asked, "hmm no I am alright kitten, but you get whatever your little heart desires" Ryder said. "Oh I will sir" Olivia said as she went to tell Kara her order, and she was going to make it super complicated.
Kara rolled her eyes but she knew the possibility of getting fired was high if she didn't do as she was told. She took the order and went quickly across to the Starbucks, Olivia waited for it patiently. Once Kara came back she handed her the drink and said, "will there be anything else?" "Not as of right now but I guarantee if you so much as look at Ryder in the wrong way today you will regret it" Olivia said as she walked away. "Bitch" Kara said under her breath, "I heard that" Olivia said, Kara didn't really care. "She called me a bitch sir" Olivia said, "hmm were you being one?" Ryder asked. "I am not sure" Olivia said, Ryder laughed, "I feel like maybe you told her not to look at me" Ryder said, "do you have a recording device on me sir?" Olivia asked, "I don't know kitten, but regardless remember who is in charge of you" Ryder said. Olivia huffed as she sat down and she studied her outfit but didn't see any sort of device. Ryder was going through dozens of emails, and a lot of them were hospitals wanting to buy his equipment, he emailed every one of them back. He also received all the information on Stryker from Cliff and he was trying to make sense of that. Olivia could sense his stress, "you okay sir?" she asked, "yeah just a lot of emails and such, a lot of info to go through" Ryder said. "Can I help sir?" Olivia asked, "yes actually you can" Ryder said and Olivia smiled as she went under the table she knew what he needed. "Always so eager but that is not what I meant kitten" Ryder said, "oh sorry sir" Olivia said, "its fine carry on, I will get the other thing later" Ryder said as he winked at her. Olivia smiled as she took his erection into her mouth after he undid his pants, Olivia heard the door open. "Thank you Kara just set it on the desk please" Ryder said, Olivia felt hot all of a sudden but she kept going. She did not want to complain today as she felt like the punishment would be something she wouldn't like. Kara hesitated and Ryder looked up at her as she noticed Olivia was not there, "Need something else?" Ryder asked her, "I am trying not to be to forward here but I think I would be a better assistant for you then her" Kara said. Olivia felt the anger and Ryder came in her mouth and she swallowed she did his pants back up but stayed under the table. "Well Kara as good as you are, my relationship with Olivia is more than just my assistant" Ryder said, "I get that but I could be that too" Kara said, "as flattered as I am Kara I am not interested. I can't speak for Olivia on this one but if she ever found out you said this she would probably not be so pleasant and I assure you I won't stop her" Ryder said. "I understand sir and I am sorry forget I brought it up" Kara said as she left the room.
Ryder looked down at Olivia he could feel her fuming, "don't overreact" Ryder said, Olivia stood up and looked at him, "she clearly just came onto you and I am pissed sir" Olivia said. "The feelings are not mutual kitten, I don't want you to do anything except sit down and eat" Ryder said. Olivia was angry but regardless she ate her food but she was not really hungry. Ryder did some paperwork, and looked to Olivia, "on the couch" he said and she walked over and sat down. "Lay back and close your eyes" Ryder said as he pulled her legs close to him, and he pushed inside her, Olivia felt his erection but also something cold and it was an amazing feeling. She groaned under it as she had no idea what it was as she kept her eyes closed, Ryder pushed harder and faster and she was getting close. "Please master" Olivia said, "no kitten" Ryder said he didn't want her to cum just yet as he pushed hard and fast and he came inside her. Ryder denied her the orgasm as he pulled out. "Sir!" Olivia said, "Strike one kitten" Ryder said, she knew that was a very loud complaint. "I get you are angry but I know it will be rewarding in the end. Kitten be a good girl" Ryder said as he kissed her head and she was frustrated she had given him 2 orgasms now and he was not letting her have any. She sat in frustration still on the couch as Ryder went back to his desk. "If you are going to continue that I will punish you right here" Ryder said. Olivia didn't care at this point anything from him was better than nothing, she thought about it for a second and walked over to him and sat down. "Do you want me to punish you?" Ryder asked. "No sir" Olivia said, "then drop the pout kitten I will deny you all day if you keep this up" Ryder said. Olivia tried her best to not be grumpy but not only was she bored but she wanted an orgasm so badly. "Please master" Olivia said, "please what?" Ryder said, "please give me an orgasm master" Olivia said. "In due time my kitten but I am working" Ryder said, "I get now why you said that I would complain today, you are not playing fair sir" Olivia said. "No you are right, but you forget that I make the rules, and the more attitude I get the less I want to please you. I am all for denying you today kitten, but if you stop complaining I might let you cum soon" Ryder said.
Olivia tried her best not to complain as she stood up, "I am using the washroom" Olivia said, "okay" Ryder said as he slapped her with a ruler when she stood up. She knew why and she rolled her eyes as she walked out of the room, Ryder shook his head she was never going to learn. Once Olivia finished in the washroom she walked up to Kara, "I would like a milkshake please" Olivia said. "There aren't any places to get one close by" Kara said, "I don't care get one" Olivia said. "Screw you" Kara said, Ryder came out of the office, and looked at them both, "Kara go" Ryder said, "there isn't one close by" Kara said. "If you want a pay cheque this week I suggest you figure it out" Ryder said. She rolled her eyes but went to get a milkshake she needed the money to pay rent. "Making her life difficult I see" Ryder said, "I really wanted a milkshake and she pissed me off today sir" Olivia said. Ryder walked up to her and slapped her, "you will pay for the eye roll later" he said in her ear. Olivia was now convinced he had super powers or something he always knew when she rolled her eyes even when her back was turned.
Kara came back not to long after finding Olivia her milkshake, she practically threw it at her. "Here, anything else?" Kara asked with an annoyed tone, "no, thank you but I guarantee if you ever so much as look at Ryder again you will regret it. I heard everything you said to him, and he is mine so don't forget that" Olivia said with aggression and this made Kara even more annoyed. Olivia walked into Ryders office and he looked up at her, "I suggest not making her out to be an enemy, we don't need that in our life. Since I pay her I don't need her seeking revenge on my fiancée, I would hate to fire her" Ryder said, "please fire her sir" Olivia practically begged, "despite your hate for her she is good at her job and Paul likes her so no. Also after this weekend you will not see her again so why does it matter?" Ryder asked. " I am worried she will end up in Chicago sir, working for you" Olivia said sadly, "kitten she won't, I have Melanie and I happen to like her, trust me no one will ever come between us" Ryder said pulling her towards him and kissing her. "I love you master" Olivia said as she cuddled into his chest, "I love you too but I need one more hour of work, then we can go have fun" Ryder said. "Okay but Lily will be here so not to much fun sir" Olivia said, "I am not worried about Lily, and if you complain then I will punish you more than I already plan too. I brought Parker for a reason and he knows how to distract her" Ryder said. Olivia huffed and Ryder laughed at her, he was going to enjoy tonight very much he had something interesting in mind.
As promised Ryder finished work an hour later and instead of going back to the hotel, Ryder was taking his kitten somewhere else. She was in for a real surprise, as they entered a club. "Um sir where are we?" Olivia asked, "I owe you a punishment for the eye roll, and this is sort of like the one in Chicago but it's not private. The public has access to it" Ryder said. Olivia looked around it did seem to be super busy, she followed Ryder into a room there was a few other people in there. "On the table, on your stomach" Ryder said to her, "sir there are people watching" Olivia said, "I won't ask you again" Ryder said with a serious tone, Olivia did as she was told. Ryder grabbed a cane off the wall he needed her to get how much he hated eye rolls, he didn't care who was watching. Plus it was practice for a show in Chicago, he was going to have Drew line it up for the Saturday after they came back. Ryder hit her with the cane 10 times, Olivia took it even though it hurt, she was not about to show weakness in front of the others. The men cheered in the background and Olivia cried she hated this so much. "I'm impressed kitten, but I can tell you are angry with me. This was for the eye roll earlier and you know I hate that. If you don't start dropping this pout I will ignore you for the rest of the night." Ryder said, "whatever" Olivia said she was mad and she wanted him to know about it. Ryder pulled her in close and hugged her, "I am sorry you are upset, but I have something exciting planned for you. I need you to behave yourself and I promise you will enjoy it." Ryder said, "I just hate you made others watch me get punished sir" Olivia said, "this is nothing compared to what I will have you do in a show" Ryder said. "We are still doing that sir?" Olivia asked, "you bet my kitten, I have it all arranged now answer me this are you going to behave?" Ryder asked her. "Yes master" she replied and Ryder gave her a kiss as they left the club. They were meeting Parker and Lily for dinner, Ryder handed Olivia a bra and another dress, "change" Ryder said, "why sir?" Olivia asked, "you want Lily to see you dressed like that?" Ryder said giving her a look. "No, thank you sir" Olivia said as she changed, Ryder watched her and smiled he loved her so much.
"Our house will be ready soon, did you want to furnish it or have me hire someone?" Ryder asked her. "I think you should decide I trust your judgement sir" Olivia said. "Alright then hire it is, I am excited to move into our new home. I also can't wait to christen it with you" Ryder said. "Sir!" Olivia said, Ryder laughed he knew she wanted to do it as well. They arrived at the restaurant and things became serious as Lily went straight into wedding talk. Olivia and Lily would be going shopping for dresses tomorrow, Olivia's mother was not able to make it but she trusted Lily to help her daughter. Olivia was anxious to get through this dinner and wondered what Ryder could possibly have up his sleeve for tonight. Everything in New York has been exciting for her so far, and she wanted to experience everything with him. Finally the bill was paid and they headed back to the hotel, Parker was staying with Lily in a different room. "Thank you Ryder for bringing me here and all of this for my girl. She deserves everything" Lily said. "I agree 100 % and you are welcome Lily, I hope we have more dinners like this one" Ryder said. "Me too and I also want to thank you for him" Lily said pointing to Parker. "Well that one was all Olivia, I genuinely would have rather he work all the time but I guess I was told that is not healthy" Ryder said. "No it is not and we are very excited to work with Stryker" Lily said, "I figured your team could handle it and I am glad, I would have not know where to start with that" Ryder said. "It looks like fun, and we love robotics and stuff so it fits up our alley perfectly" Lily said. Ryder noticed Olivia yawn and he laughed, "are we boring you?" he asked, "oh um no I am just tired" Olivia said. "She is lying doesn't want to disappoint you she is totally bored out of her mind" Lily said. "Shut up Lily" Olivia said, Lily laughed as they reached the hotel and went there separate ways.
As soon as they entered the presidential suite Ryder went straight into Dom mode he wanted to take her right there. "Strip" Ryder said, Olivia didn't even hesitate as she removed her clothes, "good girl now, arms up on the wall and legs spread for me" Ryder said. Olivia did this without hesitation, "stand further back and bend your back" Ryder said. Olivia was quick to get into position as Ryder pushed his erection inside her and fucked her hard. "Kitten, stand up" Ryder said and Olivia did and it was as if everything changed. The feeling of him inside her while standing was insane and she could barely keep her legs from shaking. Ryder was thrusting fast and hard causing her to get close to a climax, "please master" Olivia said, "not yet" Ryder said as he slowed down slightly, bending her forward again. "Master please" Olivia said she was desperate for an orgasm now as he denied her today and she just wanted to cum. "No" Ryder said slapping her hard on the ass. Olivia was frustrated as she felt Ryder cum and he pulled out not giving her an orgasm again. "Follow me kitten" Ryder said as he took her to the bedroom, Ryder tied her legs to the bed posts and pulled them up so they were above her as he spread them and pulled her arms down tying them as well. Olivia was completely exposed to him and at his mercy. "The only thing I want to here is red or yellow, you will know when you can cum understood" Ryder said. "Yes master" Olivia replied as he blindfolded her and left the room, she had no idea what was happening. Ryder came back a few seconds later and he had ice with him as he placed one on each nipple. Olivia yelped a bit as she was not expecting it, she couldn't move at all and he left them on her nipples. Ryder also pushed an ice cube inside her and this caused her to scream.
"Do I need to gag you kitten?" Ryder asked, "no master" Olivia said as she shivered a bit, the ice cubes on her nipples melted and he started slapping her with a crop. He kept torturing her with ice and it was very stimulating as the ice made the sting of the crop more intense. She so badly wanted him to fuck her again but she wasn't allowed to speak unless it was her safe words. She was no where near ready to safe word him yet. She was loving every second of this as she felt a vibrator on her clit and his erection slide inside her. Olivia moaned he felt amazing and she was getting close to a climax quickly. Ryder felt it as he pulled the vibrator away and slapped her clit with the crop. Olivia gasped but it was an amazing feeling, he sped up his pace and added the vibrator again. Every time Ryder felt her get close he would slow down and remove the vibrator making her even more desperate to cum. He denied her a few more times and kept the vibrator on this time and said "cum kitten" as she screamed and exploded around him. It being one of the longest orgasms she ever had as she felt it rip through her body. Olivia's heart was racing as Ryder came inside her and pulled out leaving the vibrator. He knew her body was not done yet as he turned it on full power. Olivia continued to moan as the vibrator kept pushing her closer and closer, "cum kitten" Ryder said. Olivia came again hard and fast as her whole body tensed under the restraints. Olivia knew he would keep going if she didn't say red but her mind was trying to catch up too her body. She orgasmed again as the vibrator continued to torment her, "red" Olivia said and Ryder stopped and untied her. She lay there tired as she closed her eyes, "you alright?" Ryder asked, "yes master" Olivia said. "I love you kitten, get some sleep I believe you have some shopping to do tomorrow" Ryder said. "Yes and thank you master for everything I love you too" Olivia said as he gave her a kiss and tucked her in. Olivia was asleep quickly, and Ryder pulled her in close as he also fell asleep beside her.