Charlotte's Dilemma

by Diane Leyne

  “Sorry, Sir.” He watched as she straightened quickly, placing her hands behind her back even as her face flamed with embarrassment as she snuck a look at their rapt audience, who were drinking in every word.

  He stood. “Normally, I’d train you slowly, bringing you along bit by bit until you didn’t just tolerate the cane, but craved it. But today, this is a punishment. It’s not meant to be erotic. It will hurt, and you will take it.”

  “Yes, Sir.”

  “But when I’m done and I fuck you in front of all of these people and you show what a good sub you are by coming for me after I set your ass on fire, then the past is wiped away. We will start our relationship fresh. You will stop obsessing about our age difference and we will both forgive and forget any hurt caused or received. Can you do that? That’s a hard limit for me. I don’t want to have the same conversation over and over and over. I’m the Dom. I’m your Dom, and I am putting my foot down. As for the rest of our hard and soft limits, we can start working out together what will work for us. I won’t impose any other rules on you but this one. Can you agree to it?”

  “Yes please, Sir.”

  “Then stand, subbie, and approach the spanking bench.”

  She moved to kneel on the bench, but he stopped her.

  “Last chance, subbie. There’s no shame in saying no. I won’t be angry or disappointed.”

  “I don’t want to say no, Sir. I love you and want to prove to you that I’m ready to move forward with our relationship, Sir. When I saw you holding Valentina, I pictured you holding our baby, and it felt right to me. I knew then and there that you were my future. I understand what you need to do, and I need it, too. This will let us both put the past behind us.” She stepped away from him and took her position on the bench.

  * * * *

  JJ’s hands were shaking as he strapped her down. He fastened each strap carefully until she could only move her fingers and toes. He then went over each fastening, making sure that she was as comfortable as could be expected and nothing was pinching and nothing was going to come loose when he got started. He needed her to remain perfectly still.

  “Even though this is punishment, because it is your first one, we’ll be using the stop light system of safe words. Green for go, yellow for slow down, and red for stop. If you say red, I’ll unstrap you and your punishment will be over.”

  “No it won’t be. It’ll be unfinished. That’s not the same thing. I want you to do this, Sir.”

  He gave her a quick kiss on the forehead. “Good girl.

  “I’m going to warm you up, first with my hand and then the flogger and the crop before giving you five stripes with the cane. Then I’m going to fuck you from behind and you will not come until I give permission. When you find release with your climax, we will also release all of our baggage. Do you understand?”

  “Yes, Sir.”

  JJ hunkered down until they were face-to-face.

  “I love you, too, subbie!”

  He could feel Charlotte brace herself, but at the first strike of JJ’s hand on her bare ass, he could tell she was relaxing. He moved quickly, covering her ass evenly and not leaving a spot untouched. Then he slid a hand over her warm pink buttocks before slipping a finger inside her.

  “You are wet, subbie.”

  “Yes, Sir.”

  “Does that mean you are turned on by getting spanked?”

  “Only when you do it, Sir.”

  “Then I’m going to have to spank you regularly, won’t I?”

  He didn’t give her a chance to answer as he laid down a second layer of handprints over the first ones. He could hear her moaning now, and whimpering a bit, too. He squatted down and saw she was crying.

  “What color are you, subbie?”

  “Green, Sir.”

  He wanted to badly to drop his leathers and sink his cock into her hot, moist pussy. She was dripping wet now, and when he slid two fingers inside her, she clamped down on her.

  “Don’t you come yet, sub.”

  “I’ll try not to, Sir.”

  “To quote Yoda, do or do not, there is no try. You will obey me, sub. No coming without permission or I’ll tan your ass so hard you won’t sit for a week.”

  “Yes, Sir.”

  He almost didn’t want to use the riding crop on her, but he had said he would, and as the Dom, he had a responsibility to keep his word. He walked over to the table where it had been laid out along with a cane. He’d picked them out thinking that Cy would be using them on Lydia. He would have to have a word with them afterward, to thank them. Clearly they’d been plotting with Charlotte, and he’d be eternally grateful.

  He made quick work with the crop, sprinkling strikes over her round ass and every four or five, striking her plump pussy lips and once, her clit. She moaned, and he could see the liquid flowing down her thighs. He clapped her clit again with the crop. More honey. Well, well, well, she liked this, didn’t she?

  But he didn’t want to give her too much to start. He walked over to the table to pick up the cane. He knew that to her, accepting this symbolized forgiveness, so he would give her what she needed. Raising his arm, he brought the cane down on her ass.

  “One.” He looked at the red mark left across her buttocks even as she screamed out with the pain and shock of the impact. It wasn’t nearly as hard as he could have made it. He was making a point, but the last thing he wanted to do was cause damage. It was her remorse and her expectation of what the cane would feel like that caused her to scream. The next four strikes would be even lighter, but he expected her to scream her head off. She wouldn’t realize the truth until she checked her ass in the mirror later and realized just how light the strikes had been.

  * * * *

  Charlotte screamed as she felt the fire across her ass from the first strike of the cane. Shit, it hurt worse than anything she’d ever felt. The spanking and even the crop had been erotic pain, but this just plain hurt. Was she nuts to want it?

  But if Lydia could take it, so could she.

  Two. Another line of fire across her ass, but this one didn’t seem as bad as the last one. Maybe the adrenaline or endorphins or whatever were kicking in and overriding her pain receptors.

  Three. Four. Five. And then it was over. It hadn’t been as bad as she’d expected. The first one had been, but then it had seemed to get easier. And now she could feel him moving behind her, his hands running lightly over her poor abused ass before one big hand moved between her legs to lightly rub her clit before a pushing a big finger inside her.

  She knew she was dripping wet, and even the pain of the caning hadn’t dimmed her arousal. She wanted, needed him inside her. And then he was. His thick cock pushed against her entrance, slowly opening her up to him. She whimpered as she tried to move against him but was prevented by the restraints.

  “Please!”

  She felt a smack on her ass.

  “Please, Sir.”

  “That’s better.”

  During their short exchange, he’d kept pushing into her and now he was buried to the root. His hipbones pressed against the cane stripes, inflaming her ass and her libido. She’d seen this happen in the playroom, but she’d never experienced it before, except when JJ had spanked her. This feeling, though, was like the spanking magnified by one thousand.

  If this was punishment, she’d be trying to piss JJ off on a regular basis. Then she stopped thinking and concentrated on his cock moving inside her and desperately trying not to come.

  “Sir, please, Sir. I need to come.”

  “Not yet, subbie. Not without permission.”

  Charlotte desperately tried to tamp down her climax, but it seemed to be taking on a life of its own. Then JJ leaned down so his front was pressed against her back. Then he reached around and took her nipples between his fingers and pinched hard.

  “Ahhhh!” He pinched again, this time tugging on them and twisting slightly as he started moving his hips again.

  Charlotte’s body was pounded by
contradictory feelings, arousal, pain, desire. She couldn’t take much more, and then she heard the magic words.

  “Come for me, subbie. Come for me, my love.”

  And she did.

  * * * *

  When she could think again, Charlotte realized that she was wrapped in a blanket and sitting on JJ’s knee on a lounger in her bedroom. She cuddled into him.

  “You’ve come back, now, have you?”

  “Yes, Sir.”

  “No, not Sir. We’re not in the playroom. Here I’m JJ.”

  “The other Doms want their subs to use their titles all the time.”

  “I’m not other Doms. How’s the ass?”

  She considered his question.

  “Not bad, considering.”

  “Considering I whaled on it?” He grinned. “I’m really not that into giving pain. I’m a control freak when it comes to sex, not a sadist. I’ll give you just enough pain to enhance your pleasure. I don’t like dishing out pain for the sake of pain, even in punishment. I hope you are going to be okay with that. If you turn into an extreme masochist, I’m going to have to find you a new Dom.”

  Charlotte leaned in and kissed him. “No, I think I have the right Dom, right here with me.”

  “Even if I’m unemployed?”

  “Even if you are unemployed. You know, this doctoring business I’m in generally pays pretty well. And I didn’t really have many expenses for the last few years. I think we’ll be just fine on one income.”

  She watched JJ struggle to say something. Oh no. Was he going to break up with her anyway?

  “Really, JJ. I–if you prefer to live here, I’ll renew my contract with the resort. I like it here. As long as I can spend time at the Jesperson Clinic every week, or one like it, I don’t care where we live. As long as it’s together.”

  “You really like working there?”

  “Oh, JJ. The staff is great. The patients are great. And they need me. They need new equipment, too. Cy and Lydia are getting them a new ultrasound machine. I’m comfortable but don’t have a ton of cash, not enough to get them all the things they need, but I want to do what I can to help them out. If I could, I’d work there full-time.”

  “You’ve got eleven months left in your contract at the resort. Maybe you can sign on full-time at the clinic when your contract’s up.”

  “Do you think so?” She brightened for a second, but then reality hit home. “I don’t think they can afford to pay me, and I need some income.”

  “You never did ask me my full name. Aren’t you curious as to what JJ stands for?”

  “You’ve always just been JJ to me. I’ll bite, though. What does JJ stand for?”

  “Jedidiah Jesperson Junior.”

  “That’s three Js.” Charlotte laughed, and then something struck her. “Wait. I’ve heard that name before. Jesperson Clinic?”

  “Started by my father in return for Roy and his family looking after me in the summer.”

  “And Jesperson Software?”

  “Used to be mine. I sold it last month. When I ran into you at the airport, I’d just gotten my freedom from the rat race.”

  “So you aren’t a beach bum?”

  “Oh, darling. I am that. But I’m a rich beach bum.”

  “How much?”

  She could see his puzzled expression, but he answered her. “Fifty million, more or less.”

  “Fantastic.”

  “My money makes a difference. Should I have told you sooner?” His tone was ice cold, and she could feel his emotional withdrawal.

  “You bet it does.” The chill between them rose. “I’ve got a fair bit in the bank, but not enough to quit working for a pay check. Now I can quit the rat race, too, and volunteer at the clinic full-time once Duncan finds my replacement here on the island. And we can afford to renovate and expand the clinic. And maybe hire another doctor. I love your money, JJ. Just think of the good we can do with it!”

  She could feel the relief flood his body as he laughed out loud.

  “You little minx. I ought to tan your hide for this. You are a very, very bad girl to scare me like that.”

  “I’m sorry, Sir. I couldn’t resist.”

  “Over my lap, now!”

  “I thought that was only for the playroom.”

  “I’ve changed my mind.” He laughed. Then he hugged her closer. “But I’d rather cuddle right now. I’ll spank you tomorrow. Don’t let me forget. Oh, and remind me to tell Duncan he’s going to have to find another doctor for the resort.”

  “Yes, Sir.” She cuddled close to him.

  “Or maybe, I should get you to tell Duncan. He’ll spank you himself, and save me the trouble, when he finds out he’s going to be losing yet another doctor.”

  * * * *

  Eleven months later, Duncan’s Office, Libertine Island Resort

  “You sure you really want to leave? We worked out something the first time you quit so you just had to work a few hours a day and we sent staff to the clinic to help out.”

  JJ reached around Charlotte and linked his hands over her heavily pregnant belly while he stared over her shoulder at his friend.

  “I had to ask, man.” Duncan shrugged and grinned. “You never know. Maybe she was getting tired of your sorry ass.”

  “JJ…”

  “Just a sec, babe. Duncan, you did and it is my pleasure to tell you that my wife and I are both moving to St. Maarten and taking over full-time running of the clinic.”

  “You are both leaving! Dammit, JJ. I’m not going to miss you, but your wife was serious eye-candy and she’s a doctor. How am I going to replace her?”

  “JJ…”

  “Give us a minute. I wanted her to leave you in the lurch months ago. She insisted on working out her contract after giving almost a year’s notice. If you haven’t found a replacement by now, it’s not our problem anymore.”

  “JJ…”

  “What, honey?”

  “JJ! I think the baby’s coming.”

  JJ felt himself going pale.

  “Are you sure?”

  Then he heard the sound of water and looked down. He saw the moisture on the ground and Charlotte wince as a contraction hit.

  “Oh, god. What am I going to do? I’m not taking a woman in labor on a boat. I can’t. What if the baby comes? Oh, god. What am I supposed to do?”

  “I’m a doctor, JJ. It’s going to be fine. You helped me deliver Valentina. You can do this.”

  “I passed out.”

  He heard Duncan snicker.

  “Laugh all you want, buddy boy, but you are going to be my assistant labor coach.”

  “Ahhhhhgggggg.” Charlotte gripped his arm with a strength he didn’t know she possessed.

  “Is she having contractions?”

  “No, Duncan, she’s just doing an acting exercise pretending she’s in agony. What do I do? Don’t just stand there. Help!”

  “What do you want me to do?”

  “We have to bring her inside. Maybe, maybe the lounge or one of the rooms.”

  “Good idea. Can you carry her? Do you want me to get a stretcher?”

  “I can walk between contractions, guys. Just hold onto me, JJ.”

  “Duncan, your wife just had a baby. You should be able to handle this. Now go get things ready.” Charlotte’s voice was firm. “Run ahead, Duncan. Boil some water. Get clean towels and get Lydia. She’ll keep a level head.”

  Duncan ran off to do JJ’s bidding without question, clearly happy to be away from the woman in labor. Charlotte would have laughed if another contraction hadn’t hit.

  “Are you sure you are okay? Maybe we should try to the mainland. There’s a clinic there.”

  “The baby’s not going to wait that long, and I don’t want to give birth on a boat when there’s a perfectly good gynecologist’s table back at the resort.”

  “I don’t remember one of those in your clinic.”

  “It’s not. It’s in a room that has given us many hours of fun, o
rgasms, and for me, occasionally, some pain in my ass.”

  JJ looked at her with a quizzical look on his face.

  “JJ, honey, Master. How could you forget? It used to be our favorite piece of equipment before you knocked me up!”

  “Oh my god! Our baby’s going to be born in the playroom.”

  * * * *

  Eight hours later, Charlotte lay back cradling her newborn son in her arms while his father lay back on the bondage table, still recovering from the ordeal of watching her give birth.

  “You know, JJ. You really are going to have to get used to this. You know I want more than one.”

  “But everything you went through…all that pain. You still want another baby?” She saw him struggle into a sitting position. He still looked a little pale.

  “What’s a little pain when you get something wonderful at the end?” She cuddled their son close. “I can’t wait to have another one or two or three!”

  “Two or three?”

  “You don’t want JR to be an only child, do you?” She frowned. “I had six brothers and sister and kind of hoped…”

  “You are not having six more babies! I forbid it. I’m your husband and your Dom, and I forbid you to put me through this six more times!”

  “Come over here and hold our son and tell me you don’t want to give him a little sister. And maybe a brother. Or two.”

  JJ moved carefully until he was standing beside her. Reaching down, he carefully picked up the small precious bundle, and Charlotte watched as he melted. “Okay, maybe just one more.”

  THE END

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  ABOUT THE AUTHOR

  Diane Leyne moved to Toronto as a young girl and she still lives and works there when she’s not travelling. In addition to writing, she’s also a passionate photographer.