Point of no Return Pleasing m...

By Calyp50

8.4K 70 0

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

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 14
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 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 27

120 1 0
By Calyp50

It was taking a little extra time to get to Dominican Republic via ship because they had to pass through Canada first. Ryder was with his security team going over details for the next few months. "Sir there are no major storms along the way but I am keeping an eye out for anything I can" Blake said. "Perfect thank you, Morgan I am trusting you to keep Olivia safe if I am not there. I mean not leaving her side at all for any reason understood" Ryder said. "Yes sir I will not let you or her down" Morgan said, "Blake you will help Morgan I want all eyes on her even if she protests. We are in foreign land and I will not have her getting hurt" Ryder said. "Understood sir" Blake said, Ryder felt he didn't have to tell Evan and Parker they were with him but he did anyways, "Evan, Parker you are with me" Ryder said. "Always sir" Evan said and Parker nodded he would kick anyone's ass who even tried to touch Ryder. 

The servers brought out drinks for everyone and Ryder took his as he sipped it Olivia walked into the room. She was wearing one of his shirts and she didn't say anything she just sat on the couch beside Ryder and curled into his lap. "Kitten I left you asleep" Ryder said, "yes and I woke up and you weren't there I was cold sir" Olivia said. "I see well I am just briefing my team on what they are doing over the next bit. Do you need a refresher too?" Ryder said. "I plan on being with you the whole time sir" Olivia said. "Most of the time yes but there will be a few times that I will need to work so you will be with Morgan and Blake. Olivia I can't stress this enough Morgan will not leave your side ever. She goes with you everywhere bathroom included, I am not going to have you disappear on our honeymoon" Ryder said. "Of course husband I get it I love you" Olivia said, "I love you to wife, now do you need a rule reminder or are you okay?" Ryder said. "Umm, I am assuming I am not allowed to talk to anyone, keep some sort of clothing on my body at all times and stay in sights of Morgan and Blake. If I am forgetting anything I am sorry sir" Olivia said. "No that was good all those rules apply, the one you forgot is that I am in charge so if I say something you do it no hesitation got it" Ryder said. "We will see sir" Olivia said kissing him. Ryder kissed her back as she became aggressive and pushed him down onto the couch to a laying position. Ryder grabbed her arms and pulled her up, "rule breaking already, looks like we need to mark that sexy butt of yours" Ryder said. "Sir please let me touch you" Olivia said, "too late for that kitten come let's go" Ryder said as he pulled her to her feet and took her to their bedroom.

"On the bed kitten face down" Ryder said and Olivia listened as Ryder pulled her shirt up and smiled as she was not wearing underwear. He grabbed the paddle he had in the drawer and said "why are you being punished kitten?" "I didn't ask to touch you master and I was aggressive" Olivia said. "I will smack you 10 times kitten" Ryder said as he slapped her on the ass, Olivia closed her eyes counting as he kept hitting her after the 10th hit she felt Ryder rubbing the lotion on her butt. "Bedtime kitten" Ryder said as he went to the bathroom to get ready and he came out and crawled in next to her. Olivia hesitated before cuddling up to him, Ryder pulled her closer and kissed her forehead. She wanted so badly to just take action and fuck him but she could tell he was tired. She closed her eyes and listened to him breathe as he fell asleep beside her. Olivia watched him for a few minutes before falling asleep herself, she hoped tomorrow would bring some new surprises.

Ryder's alarm was going off and 7 am and he rolled over and turned it off hearing Olivia groan loudly. "You don't need to get up kitten" Ryder said as he kissed her and went to get ready for the day. Olivia debated on getting up but she ended up falling back asleep as Ryder went to do a workout. He had a small gym on the yacht it wasn't like what he had at home but it was enough to get him something for the day. After his workout he went back to his room and found his girl still curled up in bed. He crawled up to her and kissed her head, "kitten you need to wake up" Ryder said. "You stink sir" Olivia said noticing he was all sweaty, "hmm well come join me in the shower" Ryder said pulling her to her feet, she knew she couldn't protest. Ryder turned the shower on and pulled Olivia in as he kissed her pushing her against the glass and she responded by wrapping her arms around his back and scratching down it with her nails. "Fuck kitten" Ryder said as he grabbed her legs and pulled her up as he pushed his erection inside her. Olivia moaned as he fucked her hard and fast while the hot water hit them. Olivia moaned and released her climax around him causing Ryder to orgasm as well and he set her on her feet. "I love you so much" Olivia said, "I love you too" Ryder said as he kissed her again grabbing the shampoo off the shelf and washing her hair. "Thank you Master" Olivia said, "your welcome kitten" Ryder said, as he let her wash him as well. Once they were done in the shower Ryder wrapped her in a towel and she dried her hair. "Breakfast will be ready soon kitten" Ryder said as he put his shirt on, "yes sir, um anything specific you want to me to wear?" Olivia said. "I like what you are wearing now kitten" Ryder said as she stood in front of him naked. "As much as I would love to oblige master I feel going to breakfast naked might be a bit much" Olivia said. "Hmm okay if you insist" Ryder said as he grabbed a dress from the closet and handed it to her, "Thank you sir, but is this it?" Olivia said. "What else did you have in mind kitten?" Ryder asked, "oh I don't know underwear sir" Olivia said. "No need this gives me easier access" Ryder said as he slapped her on the ass and she huffed at him. Ryder laughed as he left her in the bathroom and she pulled the dress on.

Olivia followed Ryder out of the room and everyone was already up and waiting for breakfast, the servers brought it out and served coffee to everyone. Olivia smiled at Ryder when they brought out a smoothie for her, she sat beside Ryder and stole one of his pieces of bacon as she sipped her smoothie. "Kitten did you just take some of my food?" Ryder said watching her eat the bacon. "I did sir" Olivia said, "hmm well something will have to be done about that" Ryder said, "bring it on master" Olivia said, "she is asking for it Ryder I would watch yourself" Drew said laughing at him. "Oh I have big plans don't worry when I am done she won't be able to sit for week" Ryder said. Olivia looked worried but she hoped that it was more pleasure than punishment, Olivia wanted to take more bacon. She watched Ryder and he said, "need something?" "I was hoping for more bacon please sir" Olivia asked, Ryder called a server over and he brought her some of her own. "Thank you master" Olivia said smiling at him, "you ask I deliver" Ryder said. "Will I get to touch you today sir?" Olivia said, "we will see kitten, after breakfast I will need to work for a bit and you can do whatever then we can play" Ryder said kissing her. "Yes master" Olivia said she was sad he needed to work she looked at him with sad eyes. "Awe kitten don't do that, if we were at home I would be going to work" Ryder said, "I know but this is our honeymoon sir" Olivia said, "she has a point there" Parker said, "We are not at the destination yet and I can't ignore work I need to do something" Ryder said, "I can help sir" Olivia said, "ugh you are making this hard for me, would it help if we played first?" Ryder said, "yes sir" Olivia said. 

"Alright then show me you want this kitten and strip" Ryder said, Olivia looked to all the people in the room and she took a breath as she took her dress off. "Have fun Ryder, if you will excuse us Jade" Drew said as he stood up and Jade followed him out of the room. The security went to a separate corner but stayed close. "Kneel and head down" Ryder said as Olivia did, Ryder left the room briefly and came back with a few toys. Olivia didn't dare move as she felt him behind her and he pushed a butt plug into her ass and turned it on. It vibrated hard right out of the gate and she moaned. "If you cum Olivia there will be consequences" Ryder said, "yes master" Olivia said, Ryder grabbed her wrists and tied them up as he secured them to the table leg. Ryder spread her legs apart and also tied them to the table leg pulling them up spreading her open. Ryder placed clamps on her nipples and these ones vibrated as well and he turned them on, Olivia was already getting close and she knew it was only going to get more intense. Ryder pushed his erection into her and she moaned under him, not being able to move at all. 

She wanted to cum so badly, but she didn't have permission and Ryder stopped everything causing her to groan. Ryder laughed, "oh kitten and we just barely started the sass is coming out early" Ryder said. Olivia didn't say anything as he pushed harder and faster turning the vibrators back on. She moaned under him and tried to squirm but it was no use and she tried to hold back her orgasm. "Please master" Olivia begged, "not yet kitten try harder" Ryder said and she was very close now and her mind was telling her to let go, Ryder noticed her tense up as he stopped again and she rolled her eyes. "Oh kitten, now there will definitely be consequences, and I am thinking maybe you don't deserve to cum" Ryder said. "Please master I am sorry it was an accident please" Olivia begged him, Ryder fucked her hard determined to finish his orgasm, "cum kitten" Ryder said. Olivia exploded around him and she moaned as it hit every nerve in her body as he climaxed around her as well. Ryder pulled out of her and said, "now I am going to work" "um sir?" Olivia said looking at him. "Yes?" he questioned looking back at her, "are you going to untie me sir?" Olivia asked. "I wasn't going to no, I think you need to learn a little lesson. You know what you did wrong and if you complain I will only keep you here longer" Ryder said. "Master please I am sorry" Olivia whined, "I will gag you if you keep this up kitten, I will be back" Ryder said as he left. Olivia was annoyed that he left her in an open area completely exposed. She cried she knew she rolled her eyes but he was frustrating and she couldn't control it sometimes it just happened. 

She was crying as she could tell people were in the room she just so badly wanted him to come back. Drew and Jade came back into the dining room, and Drew sighed, "Olivia are you alright?" he asked her. She didn't reply she knew Ryder didn't say she couldn't talk but she didn't want it to get worse. Drew knew it was only a matter of time before the servers came in to set the table for lunch and he knew they didn't know about this lifestyle. "Jade go and get Ryder for me please" Drew said, "master" Jade begged with her eyes, "go little one now" Drew said sternly and she listened as she went to find him. Drew stood guard over Olivia and it was oddly making her feel better. "Thank you sir" Olivia said, "your welcome tell me what did you do? things this morning were going so well" Drew said. "I rolled my eyes" Olivia said, "ah I see well we all know how much he loves that" Drew said. Jade came back without him, "he said he is busy but you are welcome to untie her and she is to go sit in their room and wait for him sir" Jade said. Drew nodded and helped Olivia up and handed her the dress she was wearing earlier. "Thank you" Olivia said as she went to their room she sat there and cried she was angry and she didn't know what to think. She knew she loved him and that wasn't going to change but she felt sometimes he sucked.

An hour later Ryder came out of the small office and found Drew in the living space, "I take it she didn't like that?" Ryder said, "no and I mean the servers were wanting to set the table, do they even know about your lifestyle?" Drew asked, "no but it is not there place to question it either, I pay them they keep their mouths shut. Is she in our room?" Ryder said, "some people might not be so understanding, and yes she is not to happy with you" Drew said. "Well she broke a rule and I warned her that wasn't even the half of her punishment" Ryder said. Drew laughed as he went back to talking to Jade and Ryder went down to his room. Ryder found Olivia crying in the bed and he sighed he knew she was upset and he was just going to make it worse. "Kitten I know you are upset but we are going to get the punishment out of the way, firstly because you rolled your eyes at me and you know I hate that. Secondly you made Drew take pity on you and when my mentor questions me it upsets me so I will punish you for complaining. Third you spoke to him when you know your rule is not speak to anyone do I make myself clear?" Ryder said. Olivia didn't say anything as she looked up at him she nodded but remained silent. "You can speak to me kitten tell me you understand" Ryder said, "yes master" Olivia said still crying she wanted nothing more than to take him in her arms and hold him. Ryder flipped her over onto her stomach and slapped her on the ass. "Don't move" he said as he went to grab a paddle, he came back and said. "I am going to hit you as many times as I see fit, and you have your safe words if you need them" Ryder said. Olivia felt the impact of the paddle and it hit her hard, she knew what one it was. She also knew she wouldn't be able to take to much of it as she hated how much it stung. SMACK! Ryder slapped her again, he and now hit her 10 times, and the tears were streaming down her face. She knew her butt was going to be red and most likely have bumps on it but she was going to let him punish her. After the 15th blow she screamed loudly "RED!" she knew she couldn't take it anymore. 

Ryder rubbed her butt with the cream and pulled her in close as he hugged her, she cried into his chest. She wanted nothing more than to keep holding him with everything she had even though she was upset with him. "Kitten I need to go have lunch, you are welcome to stay here or you can come join me. I will have time with you after lunch as I have done what I needed for today" Ryder said. "Can you just be my husband right now please sir" Olivia said, "I am always your husband but what can I do kitten?" Ryder said, "I just need to hold you please Ryder I am hurting and you hurt me" Olivia said. "I am sorry my love, I am here for you the rest of the day, if you want it to just be us no rules then I am okay with that but I do need to eat" Ryder said. "Okay then just us please after lunch sir" Olivia said. "Deal, come kitten" Ryder said as he handed her the dress and she followed him to lunch. Drew could tell she had been crying a lot but it seemed she was okay with Ryder as she was clinging to him. They sat down and lunch was served, and Ryder was happy to eat. Olivia nibbled at hers but she was not really hungry, "Olivia please eat love, you had only a few pieces of bacon and a smoothie for breakfast" Ryder said. "I just don't have the stomach for it right now" Olivia said and Ryder sighed he wasn't going to force her either. 

Ryder finished eating and went to the top deck to sit and relax, Olivia, Drew and Jade all followed. Ryder pulled Olivia onto his lap and kissed her as he wanted her to know he loved her. Olivia melted into him despite her being so angry, she loved him, and she knew no matter what she couldn't stay mad. The rest of the day was going well and Olivia was finally starting to feel better, "husband?" she said, "yes wife?" Ryder said, "I am hungry" Olivia said, "then you should have eaten your lunch" Ryder said to her. Olivia huffed and Ryder laughed as he called a server over and he agreed to bring her some food. "Thank you" Olivia said giving him a kiss, "anytime kitten" Ryder said as he could feel Drew giving him a look. "What?" he said, "we just dropping rules today?" Drew said, "yes she wanted to just be husband and wife for the rest of the day so I am allowing it" Ryder said. "Well I guess that is fair then, I hope that works out for you" Drew said. "I have zero complaints so far" Ryder said as he pulled her back onto his lap and kissed her with passion making her moan under him. Drew laughed as he hoped one day to have that he was not exactly young anymore. "Drew when are you and Jade going to get married?" Olivia asked and he almost choked on his drink. Ryder laughed he knew how he was with his subs but maybe this was different, he waited for his mentor to answer. "Jade is strictly my sub" Drew said, "really because I can see how much you care for her. I also think she cares a lot for you and I could see you both married" Olivia said. Drew looked to Ryder and he just shrugged he didn't know what to say. He had to admit Olivia had a lot of courage to even mention this he didn't know how Drew felt but he could see the wheels turning. Jade remained neutral the entire time as she studied her masters face, he looked to her and then to his friends. He sighed before standing and walking away and Olivia looked to Ryder, "did I say something wrong?" she asked. "I think he is confused, I mean I don't really know I don't see their relationship outside of the club" Ryder said. 

"Our relationship is complicated" Jade said speaking for the first time, "do you love him?" Ryder asked her. "of course I do so much but he is always so serious and I am not sure what to think" Jade said. "I will see what I can do Jade, Olivia if you will excuse me" Ryder said as he went to talk to his friend. He wasn't sure how this was going to go but he knew what Olivia said to him spoke a great deal and Drew was struggling. Ryder found him on the couch, "are you angry because it said something or because you are unsure?" Ryder said, "I am not angry I am just confused I guess. I mean I own Seductive and I am not supposed to marry my sub what kind of club owner would I be?" Drew said, "a damn good one, showing all the clients that it is okay to have this kind of relationship, Drew you told me its okay to love your sub" Ryder said. "I know, I mean I never really thought about it" Drew said as he sighed, "well maybe this trip will help you make up your mind, I can see how much she cares for you" Ryder said as he clapped his friend on the back and went back to his wife. 

They were do to arrive in the Dominican Republic within the next few hours and Olivia was very excited. She knew this was the one place she dreamed about visiting and she couldn't wait to spend her time relaxing on the beach with Ryder if he allowed it. 

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