Sugaring: Olivia and Jasmine

"This has been great," she agreed.

"Yeah, what a great start. Hey, I'm going to go downstairs and shower off a bit. You guys should come down, too. It's time."

Olivia's face froze. As Craig walked aft, she turned to see Jasmine looking at her with dread.

"What was that? It's time for what?"

"Shit, I dunno."

"He wants to fuck us. He thinks he's going to fuck us."

"Dammit, I never..."

"What did you tell him?"

"I, I just agreed on this date, nothing else." Olivia searched her head for what she might have missed.

"Shit Liv, I told you these guys only want sex. Did you say 'platonic only' in the profile like I said?"

Olivia bit her lip. "I didn't know what that meant."

"Fuuuuuuuuuck," Jasmine groaned. "I fucking... Never mind. This is on you. You've got to tell him."

Olivia fell back, pressing her hands to her face. She wondered how big of a deal it was. Surely daddies like Craig couldn't expect sex on every date. A thought occurred to her. How old was he really? Fifty five? Older? Could he even get it up? Possibilities swirled through her head.

"Jas'," she said quickly. "Maybe he can't even do it anymore. You know, it's like some guys just want to cuddle?"

"Liv," she said, shaking her head in disbelief. "Guys don't want to cuddle. They want to fuck." Jasmine started putting her bikini top back on. After a moment, Olivia did the same.

No more ideas came to her. She'd have to go down and tell him. If he waited for them it would only get worse.

"Go!" hissed Jasmine.

Filled with dread, Olivia crawled to her feet. Steadying herself on the railing she walked aft and down the little stairs to the cabin. Craig stood with a towel around his waist. He had combed his hair. She caught the scent of what might have been cologne.

"You put your top on," Craig observed.

"Uh, yeah," Olivia said softly. She couldn't bear to meet his gaze.

The man said nothing.

"Hey Craig, I'm really sorry but I think there may be a misunderstanding about our date."

He sighed heavily. "Okay, what? What misunderstanding?"

She groaned inwardly. Couldn't he make this easy? "I feel like you might have been hoping for sex today."

"Jesus Christ," he groaned.

"Look, I'm really-"

"'Sorry?'," he interjected. "No, I wasn't hoping for sex today. We have an arrangement. I wasn't just idly hoping you two would hop in bed with me."

Aging or not, Olivia was suddenly and acutely aware that the red-faced man was more than capable of forcing himself upon her if he so wished. She pulled back.

"I just didn't know what you wanted is all."

"Didn't know what I wanted?" He shook his head in disbelief. "Do you not know any men? Do you not know what a sugar relationship is?"

"There's different kinds."

"No there isn't!" he practically shouted. "There's one kind. Rich guy, young woman, sex, cash. That's it." He threw up his hands in exasperation and went to stare out the port hole. "Fuck," he muttered.

Their conversation seemingly over, Olivia crept back topside.

"That seemed to go well." Jasmine was waiting for her in the galley. Together, the two returned to the bow.

"Yeah, sure. Fuck. I'm really sorry Jas'." There was nothing else to say.

"I guess we'll head back now?"

Before she could reply, Craig stormed back onto the deck. He had pulled on his damp swim trunks but was still shirtless. The wind tossed and splayed his greying hair. He began to gather up the remnants of their earlier picnic, all the while muttering under his breath. It was mostly unintelligible but for one phrase in particular.

"... at least I saved myself a thousand bucks..."

"Wait, what?" To Olivia's horror Jasmine raised her voice to the man. "What do you mean?"

He turned, dumbfounded. "And I thought maybe you were the smart one."

"I'm pretty sure we had an agreement." Jasmine didn't seem intimidated.

"I'm pretty sure we did, too." Craig faced down the curvy brunette.

"So, you're some big CEO, right? Let's negotiate."

He scoffed. "Negotiation is done before the handshake, not after."

Jasmine turned and slunk away, making sure their host got a view of her wiggling butt. Reaching the prow, she reclined against the rail alluringly. Olivia was speechless.

"Now, it seems to me like there was never really a handshake here. Just some assumptions about what was going to go down today. Nothing in writing."

"No shit Nancy Drew. Of course you don't spell it out, but everyone knows what's going on here. To suggest otherwise is negotiating in bad faith. It's bullshit."

"Language, Mr. Craig, language. Don't you even want to hear my offer?"

"Provided it's better than 'motor back home and drop you off', yes. I'll listen."

Jasmine smiled, prolonging the moment. "I offer you, one blowjob."

Olivia's jaw dropped, but before she could interject Craig cut her off.

"A blowjob? Since a three-way was on the table I don't see how a blowjob is a meaningful counter. There's no such thing as a thousand-dollar blowjob."

"You haven't had one of mine." It might not be an idle boast. Jasmine had on more than one occasion bragged about her oral skills.

"There's no such thing as a thousand-dollar blowjob," repeated Craig. He was grinning though, enjoying the risque conversation.

"Oh, that's not the entire offer. The deal is I get ten minutes to blow you. I get you off in ten minutes we collect the allowance." Jasmine was twirling her hair in her fingers, locking eyes with the older man.

"And if you can't? What happens if you can't make me cum in ten minutes?" Olivia thought she saw Craig's organ stirring in his trunks.

"Oh I will." The two were both grinning at each other now.

"Maybe," admitted Craig. "But let's just say you're having an off day? What's your offer then?"

"Well then, you can fuck me. Hard as you like, really make me earn that allowance." She emphasized the word earn.

Craig considered the offer, eyeing Jasmine lustfully. His eyes flickered briefly to Olivia.

"Okay..." he said.

Jasmine chuckled.

"... with a counter. You can both blow me. Liv here doesn't have to of course, but she can join in if she likes."

"She won't need to," said Jasmine.

"But, if the two of you can't make me pop in ten minutes then I get my three-way. Not just Jasmine here. Both of you, hard as I like. A real three-way like in the pornos."

Fear shot through Olivia, tightening her skin. She glanced at Jasmine anxiously. Craig caught the glance.

"I'll give you ladies some time to talk it over. You know where to find me." He shot Jasmine one more leering glance before heading aft.

Olivia grabbed her friend's arm nervously. "Jas', what are you doing? We should just get out of here."

"Liv, I can do it, no problem." Jasmine was grinning confidently. "I'm serious, no guy has ever lasted longer than five minutes. I know my shit!"

"I don't know... anyway I didn't think you were into older guys like that."

"Sheezus Liv, I'm not 'into' him. I just don't want this day to be a total waste. Tell me you've never blown a dude just to get something out of him. You should be thanking me."

"Look, this is my fault anyway, I'm sorry. I was the one who thought-"

"Liv! Shut. Up!" Jasmine shook her head in exasperation. "I'm going down there. I want you to come along and be the time keeper. Let's go!"

Olivia stayed where she was for a moment. The wind teased her hair as the odd wave slapped against the hull soothingly. The late afternoon sun still glinted off of the water enticingly. She should be blissed out, finishing the last of the wine while Craig motored them home. The glimpse they had given him of their youthful flesh should have been enough for an old guy like him. Fuck.

Glumly she followed Jasmine to the cabin.

Craig was reclined on the bed, propped up with a pair of pillows. He was naked but had draped a towel across his penis, the outline of it unmistakable beneath the white terrycloth. Jasmine was kneeling on the bed in front of him, carefully securing her hair in a tie.

"Set a timer, ten minutes," she said, not breaking eye contact with Craig.

Olivia complied. "Say when."

Jasmine didn't reply immediately. Instead, while the older man looked on, she teasingly tugged her bikini top over her head and began to cup and fondle her own breasts.

"Did you like what you saw earlier?" She raised and kneaded both breasts before letting them fall back heavily. "My soft tits?" Jasmine released a string of drool, hitting a breast. Still without breaking eye contact she swirled the slick glob around her nipple. "Mmmm, feels so good," she said with a moan. "Bet you wish you could suck them."

If Jasmine's intent was to get Craig as aroused as possible before starting the blowjob, it seemed to be working. Olivia watched as his organ swelled, twitched, and moved beneath the towel.

"Oh, I will suck those sweet things," Craig said. "I'll suck 'em until they ache."

"No love," Jasmine said with mock sadness. "You won't. Liv, start the timer."

Jasmine tugged the towel free as Olivia started the countdown timer on her phone.

"Well then," said Jasmine flatly. She was expressionless, staring at Craig's organ. It lay across his belly like a fat sausage. Olivia had seen thicker ones in porn videos, but never in real life.

For a moment Jasmine seemed unable to move. 9:48, 9:47... the seconds ticked by. 9:44. At last the brunette bent to her work. "Big ones are easy," she said, attempting to play off her initial hesitation. "More room for my hands."

Jasmine started low, pressing her tongue flat against Craig's balls. "You shaved your balls. Good," she said, giving a generous wet lick. "You'll really feel my tongue that way. My wet tongue." She slid her tongue around the base of his sack and up the other side. "My tongue on your big balls."

"Yeah, lick 'em," Craig said. "Put that tongue on there."

"Mmmmm, you like it I know." Doing her best to maintain eye contact, Jasmine continued to swirl her tongue around and across Craig's ball sack, periodically drawing one ball into her mouth, sucking and releasing it.

"Ahhhhhh, yeah," he groaned. "So good."

Jasmine turned to Olivia long enough to flash a confident smile before returning to her work. Still tonguing Craig's sack, she reached a hand to his shaft, raised it from his belly, and began to stroke it.

"Your balls are fat," she said. Her hand slid the full length of his shaft. "How long has it been since you came?"

The older man eyed her for a moment, enjoying the show. "Just over two weeks."

"Oooh," Jasmine moaned. "You're ready to pop then. Those balls full of cum." She was still stroking him while probing his sack with her tongue. "Don't worry, I'll empty you."

"Maybe," he admitted. "Maybe I'll empty in your pussy. Or Liv's."

Startled, Liv checked the timer. 8:25. Still plenty of time. Surely Jasmine knew what she was doing.

"Who did you cum with, last time?" The voluptuous brunette was starting to work her mouth up Craig's cock. "Or did you jerk off?"

Craig smiled indulgently. "No, I don't jerk off any more. Did that when I was married, not now."

"Who then?" Jasmine briefly met Craig's eyes before returning to his shaft, kissing up his length toward the waiting head.

"My regular sugar baby. She's twenty." He was eyeing Jasmine, looking for a reaction. He got one.

"Oh, you're a naughty man Mr. Craig." She had kissed and licked the entire length of his shaft and was finally poised over the head.

"I like variety."

Not taking the time to reply, Jasmine lifted Craig's cock and slipped her lips over the bulging head. Olivia looked on in amazement as her friend's mouth stretched to accommodate him. Straining, she pushed past the head and gobbled another inch or more of cock before stopping. After a pause she withdrew, leaving behind a slick trail of saliva. Breathing roughly she glanced up to assess Craig's reaction.

"Yeah, that was nice. Do it again, deeper." He moved one hand to rest it on Jasmine's shoulder, subtly encouraging her forward.

Adjusting her position slightly, Jasmine attacked Craig's cock from a better angle. As before she stretched her mouth to get past the head before sliding down the shaft. Olivia watched as a thick vein disappeared past her friend's lips. Jasmine pulled back part way before plunging her mouth down again. Faster this time she gulped him down repeatedly before pulling back with a gasp.

"Nice," said Craig. He was clearly enjoying himself. His cock, full but somewhat soft when Jasmine started, was now rock solid. It looked especially large in her small hands. Saliva dripped from the bulging head to his full balls. On the other hand, the man himself didn't seem anywhere near climaxing. He looked more pleasantly content than he did aroused.

7:28

No longer engaging Craig in dirty talk, Jasmine got to work in earnest. Cupping his balls in one hand she resumed her plunging assault on the shaft. Again and again she pushed her lips past the head and onto the first several inches. As before, Craig rested his hand on her shoulder, and as she kept up the pace, moved it to the back of her neck.

To Olivia, Jasmine's sucking motion seemed awkward. She had to stretch her mouth to fit, which slowed her pace. Also whether from fatigue, or difficulty breathing with her mouth stuffed with cock, she had to break off every so often to catch her breath. During one such break, as she bent panting over Craig's drenched organ, Olivia caught sight of the first real concern her friend had shown. Jasmine's confidence was fading.

6:15

"Get up," said Jasmine after a series of strokes. "I want you standing."

Obligingly, Craig rolled off the edge of the bed and stood. His cock swung heavily, glistening in the light from the port hole. "That's cool," he said with a grin. "I want you kneeling."

Jasmine ignored the remark. Kneeling on a pillow, she tugged Craig's balls forward to tongue them once more. The trick had drawn a reaction from him earlier, and seemed to do the same again.

"Mmmm, my balls. Yeah, be a good girl and suck your daddy's balls." He eyed her possessively as she worked his sack over with her tongue.

Still holding his balls toward her mouth with one hand, Jasmine began to stroke him with the other. Curling her fingers around the base she drew her hand up and began sliding it around the top of the shaft and tip.

"Fuck," Craig groaned. To Olivia it was the first sign the man was starting to lose control.

5:04

Olivia watched nervously as the time remaining slipped under five minutes. Jasmine had already gone over the time she claimed to need. Although she did at last seem to be getting through to Craig, was it too late? He was a hard man to read.

Jasmine kept up with the handjob and ball teasing. Perhaps like Olivia she sensed that Craig was vulnerable to that particular combination. Perhaps her mouth was tired. Her hand was a blur, stroking and circling the bulbous head of the older man's cock. Still slick from her earlier attentions, his head and shaft slid easily between her fingers.

"Ah, that's good baby. Stroke it. Stroke my fat dick." Unlike Jasmine, Craig hadn't lost his taste for dirty talk.

Jasmine stopped again, panting. She flashed Olivia an unreadable look before turning back to Craig. Still stroking him, she seemed to be looking for any sign the man was close to cumming. She spit on his dick messily. Gradually she caught her breath.

"Yeah and suck it, too," he said with a groan. "You said blowjob, not handjob."

"Fuck," said Jasmine softly, but obliged. Craig pointed his rod directly at her, Jasmine parted her lips, and took him into her mouth. He groaned in pleasure.

4:35

Opening her mouth as wide as possible, Jasmine pushed her lips over the head and to the thickest part of the shaft before stopping. Olivia heard her gag before she withdrew. Her friend repeated the motion, then once more. She was pushing herself to the limit, stretching her mouth and gagging with cock. Jasmine struggled to find a steady pace.

Olivia looked on in wonder. She watched as strings of saliva popped free from Jasmine's mouth, slapped against her neck or fell to her breasts. Her eyes were watering.

"Guh, guh, guh, guh..." The sound of Jasmine's rhythmic gagging echoed in the tiny cabin. The brunette gripped Craig's hips with both hands, kept her eyes closed, and pumped as best she could.

"Oh, you're so good," Craig groaned. He had raised one hand to the ceiling to steady himself. His head was back, and his mouth open. "That mouth. That tight little mouth. Fuck!" Occasionally he would steal a glance down toward Jasmine, drinking in the sight of the young woman vigorously swallowing his shaft.

As she watched, Olivia recognized a growing arousal. It was like watching a porno. Jasmine plunged her mouth as briskly as she could over Craig's swollen organ while he groaned in ecstasy. The rough gagging sounds and the older man's dirty talk were the soundtrack. Perhaps she shouldn't be getting turned on from watching, but Olivia's fingers nonetheless sought her damp slit. She probed.

"Your friend..." Craig was looking at her now, his eyes slitted. "Your friend's sucking my dick so good." He was resting one hand on the back of Jasmine's head, encouraging her. "Her hot mouth." He rolled his head back before returning to meet her gaze. Did he notice her fingers slipped inside her bikini bottom?

"Tell me Olivia," he said in between groans. "Do you want me to cum in her mouth, or hold off so I can fuck you?" His hips had begun to move, trying to plant his rod deeper into Jasmine's mouth. His breath was ragged. "Be honest."

It wasn't a fair question. In truth her increasingly damp slit ached for attention. Her initial probing was quickly turning into something more like masturbation. A hard cock would feel so good. Moreover Olivia was curious what it would feel like to be stretched by an organ as thick as Craig's. Would it feel good or hurt? Or both?

Before she could respond Jasmine pulled free, gasping. Her eyes were wide, wet with the tears that streaked her cheeks. For a moment she cast about wildly as if confused to find herself in the middle of a blowjob. Finally her eyes found Olivia. "The time!" she pleaded. Her chin and neck were slick with saliva.

It was Olivia's turn to be confused. She just stared at her friend for a moment before she understood the question. She fumbled for the phone.

"Three twelve."

"Fuck," she cried out. She was desperately trying to catch her breath. "Liv, you gotta do his balls."

Fear and adrenaline shot through Olivia. Guiltily, she had hoped Jasmine's oral skills would save her from having to touch the older man. Now she found herself staring at his shaved sack with no other option than to pleasure him.

"Hurry!" There was an edge to Jasmine's voice.

Scrambling, Olivia knelt next to her friend and tried to reach the moving target of Craig's balls. As Jasmine resumed swallowing his shaft from above, his sack bounced and shifted about. Plus, with Jasmine in the way it was difficult for Olivia to get close enough. She made tentative contact more than once but each time Craig's bucking hips or Jasmine's arm would get in the way. Precious seconds slipped by.

"Dammit!" Jasmine cursed again. "On your back on the bed. Hang your head over."

Olivia did as she was told. To her surprise, Jasmine lay atop her, soft breasts pressing against Olivia's taut mid-section. Her friend's face was inches away.

"Here." Jasmine called to Craig.

"I like it!" The older man approached, grinning. Understanding Jasmine's intent at once he placed one leg either side of Olivia's head and lowered his balls to her waiting mouth. She closed her eyes and began sucking and licking his sack. He moaned.