Charlotte's Dilemma

by Diane Leyne

  “If you insist, but don’t try to wake me up in the middle of the night for sex just because you can’t sleep.”

  Chapter 5

  JJ was having the best sex dream ever. He could almost feel the lips wrapped around his dick, sucking hard enough to remove paint from a wall. He groaned and flexed his hips, reaching down to take care of his morning wood. This dream was too good to waste.

  He realized he wasn’t dreaming as his hand encountered Charlotte’s short mop of hair and the events of the day before came rushing back. She was kneeling between his legs and diligently trying to suck the cum right out of his cock. Groaning, he felt her cup his balls and squeeze lightly as she did something with her mouth and took him so deep that he could feel her nose pressing against his pelvis.

  And that did it. He could feel his balls draw up and the long ropes of cum shooting directly down her throat, as she kept the suction while she continued swallowing until he was spent. Then she slowly released him, licking his cock clean before kissing her way up his body.

  “Good morning, sleepyhead.”

  “It’s a very good morning, and I loved the sleeping head. It’s the perfect way to wake up. Forget alarm clocks. I want to wake up every morning to your mouth sucking me dry. You have a mouth like a vacuum cleaner. Why did I ever turn you down last night?”

  JJ smiled as she blushed delightfully.

  “Because you are a dumbass?”

  “Probably.”

  Rolling, he pushed himself on top of Charlotte. Smiling, he kissed her face, avoiding her mouth. He kissed her forehead and her nose and her jawline. He nibbled on each earlobe, teasing her until she grabbed his head and tried to reposition his mouth.

  “Naughty, naughty. Where did I put your hands last night?”

  “Over my head.”

  “And why aren’t they there now?

  “But I want to touch you.”

  “It seems to me you already touched me plenty this morning.” JJ levered himself up so that he was straddling Charlotte’s hips. “And as delightful as it was, it was unsanctioned touching. I think I may have to punish you.”

  “What are you going to do, spank me?” JJ grinned down at Charlotte and her mock pouting. Laughing, he moved quickly as she shrieked in protest.

  “Not a laughing matter now, is it?” he demanded as she lay across his lap, her ripe round buttocks in the air just begging for his hand.

  * * * *

  Charlotte shrieked and wriggled, but she was held tightly across JJ’s lap, his erect cock pressed against her side, his right hand on the small of her back holding her in place while his right hand moved lightly over her ass.

  “Legs apart,” he ordered.

  When she didn’t move, his hand came down sharply on her left ass cheek.

  “Legs apart.”

  Still she hesitated, and this time he slapped her right ass cheek. Quickly she moved to obey, widening her legs a few inches apart.

  “You can do better than that.” Smack, smack. He slapped both ass cheeks, and she moved her legs further apart and kept moving them wider until the swats stopped.

  “Good girl.”

  Now he was massaging the very spots he’d just hit, rubbing the heat and seemingly spreading it. Charlotte had never been spanked before, not even as a little girl. It was just as arousing as she had imagined it to be. Or maybe it was just JJ and his magic finger. She could feel her clit starting to ache and the moisture seeping out of her pussy onto his leg.

  “Someone’s getting horny,” he teased, moving his hand between her legs, one large finger sliding inside her. She felt him swirl it around and remove it. Then she heard a sucking sound.

  “You taste just as sweet this morning. But you’ve been naughty. I had planned to start the day by worshiping your tits, but you have to be spanked first. Then I’m going to use our last condom, have a shower, and then get some breakfast. Then I thought we could walk into town and pick up a new supply of rubbers before heading to my boat. I know a nice, private beach where we can spend the day. How does that sound?”

  Charlotte thought it sounded like an excellent plan, well, except the spanking part, but he was playing with her again, pressing his fingers inside her and using his thumb to stimulate her clit, and suddenly she wanted to feel his hand on her ass again. She remembered how much Lindy seemed to enjoy it. Hell, after he spanked her, Jake had used a strap, a paddle and even a cane on her ass before fucking her to a screaming climax. Would she climax if JJ did that to her?

  She felt JJ’s hand come down hard on her ass again. Four smacks this time, two on each cheek, before his fingers worked their way inside her again. She suddenly needed to move. And she wanted stimulation on her clit again. She tried to rub it against him, but he pulled his fingers out and smacked her ass again, harder this time, before reaching between her legs, touching her clit lightly.

  Just a little more and she would come. She knew it.

  “You don’t have permission to come, Charlotte. Last night, I told you that I’d make you come over and over. This morning, the rules are different. You don’t have permission to come until my cock’s inside your pussy. Come now without permission and you don’t get to come again for the rest of the day.

  Charlotte groaned in protest. How had she ever thought JJ was easygoing? He was clearly a Dom through and through, and damned if it wasn’t turning her on, even though she was not happy about his order. A Dom? Where had that thought come from? Did he ever visit Libertine Island? Would she see him there with some young hottie, come to play?

  And then his fingers were inside her again and all rational thought was driven out by the strength of her arousal.

  “Please, JJ, I need to come.”

  “Begging’s not going to help, sweetie. In fact it may just annoy me enough that I won’t let you come again today. Hmm. Would you like that?”

  “No, Sir!”

  JJ’s hand froze, three fingers deep inside Charlotte.

  “What did you say?”

  “No?”

  “You called me Sir.”

  “I did?”

  “You did, and I like it. Let’s just finish your spanking, and, what the hell, I give you permission to have one orgasm once your spanking is over, but not until I give the command.”

  Then his hand rain down slaps all over her ass. He never hit her in the same spot twice and it hurt. A tear seeped out and then another. She was on the verge of some kind of breakthrough. She just needed more of something. More pain? She didn’t know what, but she was on the edge of something big, but then his hand moved and he was slapping her pussy lightly and then pushing his fingers inside her and pressing on her G-spot. Then another slap and another stroke inside her and then the waves of pleasure started growing inside her as if she was on the edge of an orgasm.

  She could hear his laughter. Did he feel it, too?

  “You may come at any time, sweetie.” And then he was slapping her harder, his hand moving down so that he was hitting her clit along with her pussy before sliding inside her again. He did it again and again, and on the fourth strike, it was like she was breaking into a thousand pieces as she came hard, bucking against his restraining hand as he finger fucked her hard, drawing out her climax as waves of pleasure tore through her until she lay across his lap, spent.

  With a laugh of sheer delight, JJ maneuvered her limp body until she was lying on the pillow again, her spread legs cradling his body as he positioned himself at her breasts. She closed her eyes and lost herself in the feeling of his mouth and fingers on her breasts and nipples, massaging and pinching and soothing and tugging and even biting lightly until her arousal rebuilt and she was begging him to fuck her again.

  Finally he donned the last condom and pushed inside her to the hilt with a single stroke, and then he stopped.

  “Wrap your legs around me and hold on tight. And I’ve changed my mind. You have permission to come as often as you like for being so good during your spanking.”

  * *
* *

  Charlotte couldn’t remember being so happy in a long time, or so sexually satisfied. It seemed like she and JJ made love or fucked or somewhere in between several times a day. She didn’t end up seeing much of St. Maarten other than on their first morning together.

  They walked into town following along the beach. It was impossible to get lost, and the walk was beautiful. Great Bay was just that, a horseshoe-shaped bay. Her hotel was on one side and the docks were on the other, and Philipsburg, the capital, was in between.

  It was an easy walk, too. The sand was packed down to form a path for part of the way. Then they met up with a street that ran along the water, with the public beach on their right and stores on their left.

  Charlotte was surprised by the lack of vendors or general pushiness toward tourists. There were a few small stalls set up selling souvenirs, and a couple of women braiding hair. They’d started to ask her if she wanted their services, but then they’d all laughed. Charlotte’s hair was short and spikey, perfect for living in areas where a shower was a luxury. JJ, on the other hand, had hair that went down past his shoulders.

  Laughing, the three of them convinced him to take a seat. In the end, he wound up with two braids on each side, with brightly colored beads covering the last few inches. Charlotte and JJ had pulled out some cash at the exact same time, but in the end, he had gotten his way and paid. Charlotte wasn’t happy, especially when she saw how little money was in his wallet, but she didn’t want to embarrass him, either. Just because he was a guy didn’t mean he had to pay, especially since it had been her idea. She kicked herself for putting him in the position where he felt the need to pay for something so frivolous when he clearly didn’t have much. Most of his clothes were well worn and a couple of his T-shirts were so well worn that they should be used as rags and not worn.

  She, on the other hand, had had nothing to spend her, albeit measly, salary on for the last five years. Her investments had grown, too, and she had the proceeds from the sale of her condo before she’d gone overseas to work. In short, she was no Bill Gates, but she didn’t have to work for a few years, if she didn’t want to. She was now taking yet another job that included room and board, so her savings were just going to keep growing.

  They had an early lunch at a charming outdoor patio, and then they’d walked back to the hotel following the main street that ran parallel to the water after first stopping at a pharmacy. Again, JJ had insisted on paying. In fact, he wouldn’t even let her go in. While she was waiting, her eye was caught by a shop across the street. Prada. And it looked to be the real deal. In particular, she saw a silvery gray golf shirt that would look amazing with his eyes.

  She kissed his cheek. “Fine. You pick up the necessities. I’m going to splurge on a little something. I’ve got five years back pay to blow.”

  “Not all at once,” he teased. “I’ll be sitting on that bench over there waiting for you.”

  “You won’t come in and help?”

  “No. I’ll be waiting to be surprised at a private fashion show tonight.”

  Charlotte moved quickly, heading into the store. She wouldn’t need much time. She walked in and pointed to the shirt she was interested in and checked the label, the seams, and the price. Definitely the real deal. She thought for a moment. The dark-silver shorts it was paired with would look amazing on JJ along with the white boat shoes.

  She told the salesman to wait and dashed out. JJ smiled inquiringly.

  “You have to come in and try something on for me. I have found the perfect outfit for you.” She grabbed his hand and tugged, but he tugged back.

  “What’s wrong?”

  “Don’t you know how expensive that place is?”

  “Sure, but I wanted to get you something nice. Your tee will probably fall apart the next time you wash it, and your shorts aren’t much better. Let me get those for you. They’ll definitely impress the tourists you are going to be schlepping around. Or you can just wear them tonight. I’m not trying to change your style. You have great legs. We can go down to dinner, and you’ll look all fancy in your new designer shorts…”

  Slowly her voice trailed off as she realized he wasn’t answering or smiling or even reacting. He was just standing there, his face almost blank of emotion, his cheeks bright red. Was he angry? Embarrassed? She realized that he’d dropped the bag from the pharmacy and crouched down to pick it up.

  “I’m so sorry. I didn’t think. I just wanted to do something nice for you. You wouldn’t even let me pay the hair braiding lady. And, well, you…”

  She’d taken a peek in the bag as she started to hand it back to him, and her eyes nearly popped out of her head at the stack of condom boxes JJ purchased.

  “Are you sure you have enough?” she’d asked dryly.

  “I think we’re good.”

  “But we’re going there in just over forty-eight hours.”

  “You’re right. We need more.” JJ shoved the bag toward Charlotte and then fled back into the pharmacy. Fled. That was the right word. Like he needed to get away from her. On the plus side, though, he was going to buy more condoms, which hopefully meant that he wasn’t dumping her over some stupid shorts.

  Charlotte peeked in the bag and started chuckling. She wouldn’t be able to walk by the time they left for the resort if he thought they needed more.

  She saw a movement out of the corner of her eye. It was the salesman from Prada. He caught her eye and smiled. She shook her head and shrugged. He just gave an obvious sigh and disappeared back into his store.

  When JJ came out, he looked like himself again. She laughed with relief. When he asked what was so funny, she figured she needed to change the subject and told him her thoughts about not being able to walk if they used all the condoms by Monday.

  “That’s not funny, not at all,” he insisted. “In fact, it’s my goal in life. That, and making you come so hard you pass out from the pleasure.”

  Charlotte turned to JJ, her eyes wide with amazement, relief, and just a little arousal. Considering he’d fucked her senseless last night and again this morning, she couldn’t imagine what it would feel like to actually be rendered unconscious by the intensity of an orgasm, but she was willing to find out.

  * * * *

  The time seemed to fly by. They spent all of day two on the private beach swimming naked and making love and then swimming some more, using up a shocking number of condoms. Charlotte would have loved to be with JJ without the latex between them, but even though she was on birth control, she didn’t know JJ’s sexual history and wasn’t willing to take a chance. To be fair, though, he never pressured her. He seemed to have no problem gloving up.

  It was like there was just the two of them left in the world, their very own Blue Lagoon. Of course, they also had the food packed by the chef at the hotel. Foraging off the land would not have been romantic. Neither would sunburn, but they were in no danger of that. JJ had taken a particular delight in rubbing sunscreen into every square inch of her body, including those that never saw the sun, and she’d returned the favor.

  The one thing they didn’t do much of was talk. JJ had tried to start a conversation that went deeper than what’s your favorite color more than once, but Charlotte put him off. She knew their relationship wasn’t going anywhere, so she was trying hard not to get emotionally entangled. This was a fling. A sexual escapade. A…a…an affair, that was what it was. A three-night stand. She was determined to keep it light and not get involved. He’d also asked where she was going to be working, and she put him off by grabbing his cock. She didn’t refuse to answer outright, but she did avoid saying where she’d be working until she’d distracted him to the point where he forgot what he’d been asking. And when he tried to talk about his job, she dropped to her knees and took his cock in her mouth and all conversation stopped.

  * * * *

  In no time at all, it was Sunday, her last day in St. Maarten before heading to Libertine Island, and the day of the Dupris family barbeque
. She tried to back out, but JJ wouldn’t let her. He’d been so sweet and accommodating and easygoing, but on this he was firm. She’d promised to go and he’d promised to take her, and Roy would have his hide if he didn’t present her to Marie this afternoon.

  Charlotte wanted to argue. She’d only met Roy the once. She was a stranger. She had nothing to wear. JJ had gotten stubborn and dug in his heels. They were going if he had to throw her over his shoulder and kidnap her for the day.

  “Besides,” he added, checking his watch, “Roy will be here in half an hour.” He lay back on the bed and grinned up at her.

  “Fuck. Fuck, fuck, fuck.”

  “Now that isn’t very nice language for a young lady to use. I hope you don’t plan on talking that way in front of Marie and Roy. I might have to spank you again.” He sat up and swung his long legs over the edge of the bed, reaching for her arm and pulling her toward him. “Now just lean over my lap and get it over with, like a good girl. Then we’ll have a quickie and you can have your shower.”

  “There’s no time,” Charlotte protested half-heartedly as she let him lay her across his knees. She could feel his hard cock pressing against her side, and then his big hand was coming down on her ass and she wasn’t thinking anymore.

  * * * *

  JJ stepped out of the shower. He’d let Charlotte flee to the bathroom alone after their quickie before having his own. He’d have liked to shower with her, but he knew that if he joined her, there was no way they would be ready on time, and Roy, damn him, was always early.

  JJ slipped on his shorts and then donned a short-sleeved shirt with a bright tropical print. It would have to do. All the rest of his clothes were on Libertine Island. Hell, he probably should have let her buy the damned shorts and shirts in Philipsburg. They weren’t that expensive. It’s not like she’d offered to buy him a car or something. Besides, she’d told him that she had saved almost all her salary for the last five years and had tons of cash in the bank, so the money wasn’t a problem for her. She wasn’t spending her last penny buying him a present, but it did serve to remind him that he was lying to her, even if only by omission. She wanted to buy him those things because she thought he was poor and felt sorry for him, not as genuine gifts as if they were equals, a couple, one of which wanted to buy the other a present.