First Day in the Caribbean 14

Story Info
Satisfied flight attendant, then waitress, finally our hero.
4k words
4.71
14.4k
4

Part 21 of the 31 part series

Updated 06/07/2023
Created 12/06/2015
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Ennis Piceo
Ennis Piceo
105 Followers

When Mary's alarm went off, she immediately grabbed his semi-stiff member and got it nice and hard. "See what a good alarm clock I am? I got you right up." She climbed onto him. "You just stay there; I need a quickie," and she rode him, sliding her body on his, plunging him into herself faster and faster until she stiffened and trembled in climax. Asch was almost ready to come himself. "Ah, thank you. That was nice. Your attention means a lot to me, Asch. It's something to remember you by. I'll let Octavia finish you off," and she smirked and left him hanging. They got up and headed for the café.

Around a couple strips of bacon Mary said, "Well he's all yours. I used him this morning, but didn't use him up."

Octavia got a knowing look on her face. "I don't think we'll ever completely use this guy up. But it'll be fun to try."

Mary took her leave, insisting that Asch stay put, so he ate slowly and enjoyed the female scenery while he waited for Octavia to finish her shift.

"Are you staring at me, mister?" Octavia asked after a while.

"Yup," he leered.

"Well you just better keep it up or you'll get yourself into trouble," she scolded.

"I'll do my best, Ma'am," he said pretending to be contrite. "I can offer my hotel room as penance if I'm not fresh enough here."

"Hmm, that's right. Closer than your place." She looked at him through lowered eyelids. "There's no way you can be fresh enough to satisfy me here, so I'll take the penance. I could use a little sleep."

A fellow about three stools down looked at Asch with admiration. "I don't know how you do it, man, but a lot of guys would pay big bucks to learn your secret," he nodded his head toward Octavia, "She's fun to look at, but normally she has a heart of ice."

Asch made a stage whisper. "I spiked her coffee earlier."

Octavia overheard. "You did not. I spiked it myself! What you spiked was—well, never mind." She looked at the man, "actually, Asch and I have known each other for a while, and sometimes our banter gets suggestive. But I assure you, he's a perfect gentleman and he has never made me the least bit uncomfortable." She brought coffee refills. "Don't give up hope, though—someday you might be as lucky as him. Different girl, of course."

The three continued the conversation. It came out that the fellow kind of liked a woman at work but hadn't even approached her for fear of causing harassment problems. Asch and Octavia agreed that a neutral out-of-work activity based on some mutual interest was his best bet. "And don't say or do anything about sex until after she does."

Octavia's shift ended and they headed out. "Good luck," she wished the man as they headed out. On the street she said, "I gave my notice. They begged me to be available for emergencies and to train my replacement. And to find one if I could."

"It'll be nice to have you around more," Asch agreed, "and I think it'll be good for you to have a more normal schedule, too. Think of it—sleep at night and play during the day!"

"And just what kind of play did you have in mind, pray tell?"

"Well, we could take scuba lessons..."

"You might recall, sir, that I have advanced and nitrox certifications. But I can hold you under water if you like."

"You can hold me any place you want," Asch deliberately misinterpreted her remark.

She picked up the ball. "Can I hold you here?" She squeezed his arm. "How about here?" She stepped in front of him and reached behind to grab his crotch, which she discovered was already showing interest in her. "Hmm. I guess that's a 'yes!' "

At the hotel desk, Asch asked to keep the room until the last possible checkout time and slid a twenty across the desk. "I'll leave something in the room to make up for the cleaning crew's inconvenience," he said. "about 4:00, right?"

The concierge smiled and the twenty disappeared. "Or five; whenever."

When they got to the room, Octavia put her arms around his neck, enjoying the contact. "You sure know how to smooth things out, don't you? Sometimes I wish I had that kind of money. And thank you." She kissed him.

"Well, I ain't got nuthin' else to spend my money on, and you're worth a lot more to me than a couple twenties." He started to unbutton her blouse. "And you're welcome."

She closed her eyes to savor the sensation of being undressed, feeling his light touch down her front, the top sliding down, his arms reaching around her as he stood closer than necessary to unfasten her bikini top. "Hmm. Y'know, we never have gone swimming together," he murmured, taking her naked torso in his arms and kissing her neck.

Keeping her eyes closed, she reached for his T-shirt and pulled it up. He kept their bodies in light contact, and the sensation of her breasts contacting his chest was pretty fun. "Okay, now the shorts."

He kissed his way down to her belly and unfastened the snap. then he kissed where the snap was. Then he slowly unzipped the zipper, following the slider down with his tongue. "Walk backwards," he ordered. When she got a couple inches from the bed, he said, "fall backwards," which she did. He slid the shorts off, dropped his own, and moved himself between her legs, which were dangling mostly off the edge of the bed. He kneeled and pushed her knees apart. Knowing it would appeal to her exhibitionism, he said, "Mmm spectacular view," looking at her wet slit and baby-soft labia, and seeing her hands on her breasts in the background. "May I touch?"

"Quit procrastinating!" she moaned.

He leaned forward and ran his tongue around her outside, then up and down her slit, working his way inside. Her breathing became heavier, and she gasped when he made circles around her clit. He grabbed her hips to pull his face closer into her, kissing and sucking more and more aggressively, matching her moans and thrashing. She came suddenly, crying out and trembling, finally heaving a big, satisfied sigh.

"All morning I've been thinking about you two making out, and having Mary tell me that she didn't use you up really turned me on." She sat up suddenly. "And here I've left you hanging just to satisfy my own lust! Get on the bed! No wait." She hitched herself closer so she was barely on the edge of the bed. "Do me here, now. I want you inside me," and she pulled him toward her.

Asch spread his feet apart to lower himself a bit, but she was still a bit too low for comfort.

"Hang on," and she rolled part way over, bending her feet to keep his legs trapped close to her, and grabbed the pillows and tucked them under her hips. "Now do me."

The height was just enough, and Asch slowly moved himself toward her. She pulled on his legs in her eagerness, and as soon as the head touched her, she scooted forward onto him, then grabbed his waist and pulled, falling back, pulling him onto her. The balance was wrong, and in spite of himself, Asch slid onto his knees on the floor.

"Hmm. You must really like my tongue!" he chuckled.

"No! Well, yes, but I want you in me!" and she scooted farther onto the bed. "Come here, big boy. I want to please you. Have your way with me, please," she said with a pleading tone in her voice.

Asch locked eyes with her and climbed onto the bed between her wide-spread legs. He put his arms beneath her knees and took her hands in his, forcing her legs into the air. Still looking at her, he pressed his member against her until he slid in, slowly, deeper and deeper until he was buried all the way in. Then he pulled almost all the way out and stopped. "I really like looking at your breasts, and feeling myself inside you. I think I'll do both some more."

The intensity of what she could feel was already making her head spin. "Yes, and don't stop," she moaned.

So he didn't. He accelerated his pace as slowly as he could, but her hip rocking and moans were exciting and kept encouraging him to let his reflexes take over. Finally her moaning signaled that she was about to come again, and that pushed him over the edge, and he pounded into her with such urgency that they climaxed at the same time, her crying out matching his primal grunts as he filled her. He stayed inside her, motionless for several moments, until he sensed that she was relaxing.

When he lay down next to her, she smiled and said, "I'm glad we're not keeping score, because I'd be way ahead."

"Score? I scored big time when I met you. I'm having the time of my life, and I'm happiest that I please you. Are you pleased enough to get a little sleep?"

"Mmm hmm," she nodded, suddenly realizing she was sleepy. She pulled herself closer to him and snuggled down. She heaved a contented sigh and was asleep.

Asch let himself drift off for a while, but he had gotten a fair amount of sleep already, so he woke up while she was still deeply asleep. He rolled out when she moved and sat in the easy chair to read up on scuba and Caribbean island tourism.

After an hour or so he drifted off again, naked, right there in the chair. He was startled awake by the feel of two soft, warm hands on his penis. He looked at Octavia grinning at him. "I thought this'd be the nicest way to get you up." Pretty soon he was hard, and with a smug smile, she plopped herself onto his lap, making sure to impale herself in the process. "Now, if only I can keep you up, I won't be late for work. Of course, I have a whole hour," and she began to rotate her hips sensuously, closing her eyes and smiling contentedly at the sensations of feeling him moving around inside her.

Asch spread his legs, forcing hers apart and enabling her to bury him deeper. She put her hands on his shoulders, moving to get the sensation of him inside her and the pressure of his pubic bone on her clit just right. He put his hands on her breasts and squeezed her nipples between his fingers. She kept her eyes closed, alternately bowing her head and tilting it back, concentrating on the sensations in her womanhood and nipples. Her breathing grew more ragged, and she moved her hips more urgently. Asch felt himself getting more excited. He began to buck his hips in time with her movements, and his breathing became more ragged. They bounced harder and harder until she started to convulse and tremble, squeezing her eyes shut and crying out in passion. Then Asch came too, thrusting reflexively, squeezing her breasts as he gasped, emptying himself into her.

When she came back to earth, she stood up, still shaky, and heaved a deep breath. "Wow. I make the best alarm clock in the world!" She paused some more, reveling in the afterglow. "I need a quick shower. Come and scrub me."

"Okay. You make the best alarm clock in the world, by the way," Asch quipped.

They were both still recovering from their lovemaking, so the shower was, except for some flirting and suggestive scrubbing, fairly businesslike.

Asch left a twenty on the bed and they headed out for Rita's, arms around one another.

"So what were you reading?"

"In the chair? I was getting some background on what Bill would be doing if he had a tourist business with a boat."

"Not reading porn, eh?"

"Woman, I have no need to read, or look at, porn." He gave her a squeeze. "I don't even own a pornograph. And, we actually have two unplanned hours before us!"

"Let's stop by the bike shop and see if there's any news from Jenny about Easthaven."

Jenny was waiting on a customer, so they killed a little time looking at brochures. On earlier occasions Asch had been gathering information; this time he looked at them with an eye to going on an excursion himself. They turned out to be uniformly not quite interesting. It looked like the island's infrastructure was pretty much a couple fans of roads from where they were to the east side, with a couple roads along the east coast connecting several villages. Easthaven appeared to be the largest. There was nothing south of Easthaven, and no roads paralleled the south coast of the island.

Jenny sent two parents and a very excited 10-year-old out the door, and came over. "Well, now all three of them have bikes. I see happy times ahead." she looked at Asch. "Their first trip is going to be to Pirate's Cove. That seems to be a good one for that age group. I'll bet you guys came by to get the latest Easthaven scuttlebutt." She scowled, "Too bad Sharon just left. She works here mornings now." She brightened. "Bill let me hire her! But anyway, wait'll you see tomorrow's paper. Should be an interesting read."

"So you're going to keep us in suspense until tomorrow?"

She looked mischievous. "I probably should so you'll get the official version, but here's my version of what Sharon told me." She leaned back against the counter and counted off on her fingers, "First, everyone is pretty happy that Mr. Oily or should I say Waheed got his comeuppance. The FBI is keeping the original contract as evidence, but everyone considers the whole deal to be off. Second, Mr. Conner is very apologetic; he admits being hornswoggled and blinded by the "gifts," isn't putting any spin on it at all, though he does say he thought at the time that it would be good for the town. Third, he's encouraging everyone to come to the rescheduled town meeting Tuesday, council quorum or no, so I think it'll be a full house—it'll be a citizenry discussion and Mr. Conner has indicated he'll do what he can to persuade the council to do its job and follow the wishes of the town. Mrs. Needle is having the time of her life getting interviews and doing other newspapery stuff." She paused long enough to look philosophical, "I guess our posters are obsolete now, but it was fun for Sharon and me to get excited and actually do something for a worthwhile cause." She paused again. "Maybe 'fun's' not the right word. Enlightening. Motivating. Anyway, it really affected Sharon. She actually looks older; more serious."

A group of tourists came in in a hurry to return their bikes, so Asch and Octavia left Jenny to her work. "I wonder where Bill is," remarked Asch.

Octavia had a good guess. "Remember mentioning that storefront up at the north terminal? Wide and shallow two storeys? He mentioned that he's negotiating to buy or lease it from the old guy who's in it now."

"Well good for him. I hope he isn't too hard on the guy." Without particularly thinking about it, they walked north toward the terminal. They could see Sadie's place in the background, but Asch turned toward the potential bike store. They saw Bill and the old guy shaking hands and nodding. They both sported big grins. "Looks like we got here just in time for the celebration," Asch said.

They were heading straight for the store, so Bill noticed them, and waved. "Here's my friend Asch and my beautiful sister, Octavia. Guys, meet Pete Penny. We just worked a deal that I think'll make both of us happy."

Pete recognized Asch. "Weren't you the feller who came by about a week ago asking a lot of questions and acting interested in my place here?"

Asch acknowledged that he was, and apologized for not bringing Bill by in person.

"Well, that's okay. We struck up a fair deal, and I thank you for sending him to me. We're gonna change most of the inventory to bicycle stuff, I get to learn about renting bikes, for a commission, and get to keep my place upstairs. And he gets the mortgage! heh heh. All we need ta do is ta go do the paperwork at the bank."

Octavia gave Pete a kiss on the cheek. "Pete, welcome to the family. It's good to have you. Maybe you can keep Bill in line!"

"Oh, I'll keep him in line, all right. I happen ta know sumpthin' about him that he'd prefer I keep secret, so yup, we'll get along jiss fine."

It was getting to be time to head for Rita's, so Asch and Octavia took their leave.

Pete looked at Bill, "Nice boyfriend yer sister's got there. They'll make a nice couple. I think yer a pretty lucky guy."

Bill asked, "I think you're right. But what is it you know that I want to keep secret?"

"Uh-uh, sonny boy. Now it wouldn't be a secret if'n I told, would it? But don't worry. I'm glad ta be working with you, an' yer secret's safe with me," and he gave him a friendly jab with his elbow. "Now I'm gonna start movin' some a' these here crafts ta get ready for the bikes. Meetcha at the bank at 9, right? Saturday Charlie an' I'll start puttin' in the bike furniture like we talked about, right? Can ya tell I'm kinda excited?"

Bill confessed that he was excited, too. They shook hands again and Bill headed for the shop to talk to Jenny and Charlie about the new situation, wondering all the way what it was that Pete had on him.

On the way to Rita's, Octavia coordinated her schedule with Asch. "I think I'll just put in an appearance at home tomorrow morning, then come up and sleep in your bed, if that's okay?"

"Woman, you have never asked permission to get into my bed! And you never need to. And I'd never tell you 'no,' anyway, for that matter."

"I guess that's a 'yes'," she giggled. "Say, I wonder what Pete has on Bill to keep him in line."

"I'll bet he doesn't have anything; he just said it to keep Bill worried, so he'd be a good boy."

Octavia laughed, "You really think so? That would be a stitch if it were true."

"Well, what previous contact have those two had? What opportunity might Pete have had to pick up any dirt on Bill? For that matter, what actual bad thing would Bill have done? He's just sneaky enough to have a not-quite-clean conscience, so he's gonna be careful."

"Ha. Well, the deal sounds fair to both of them, and might work out pretty well for the store to boot." They reached Rita's back entrance, she gave him her usual fond farewell, and he headed for his room.

He saw the mayor's SUV in the driveway when he arrived. It turned out that he and Lydia were in the kitchen having a bite to eat. "Your timing is perfect tonight," she said. "Grab a bowl. We're having stew."

Asch helped himself and sat down. "You don't usually eat this late," he remarked, "But I'm glad you did. I'm hungry."

"Lydia knew I was coming and she fixed this outstanding comestible." Her gave her a nod. "I got here only a few minutes ago, so your timing is indeed good." He looked down and sighed. "And since you were instrumental in saving our town, I think it's good that you're here to hear what I have to say. First," he turned to Lydia, "I can't thank you enough for taking Sharon under your wing at the meeting. It helped her a lot. At least she's speaking to me again," he added ruefully.

"Hey I'm a motherly type, that's all. But I'm glad to hear she's feeling better."

He nodded acknowledgement. "Second, I haven't heard any calls for my resignation, but I'm considering resigning. I allowed myself to be completely buffaloed by that guy. I don't think that degree of innocence and gullibility is appropriate for someone in public service, at least not on the executive side. I feel that I would be remiss to leave while this issue is still being dealt with, but when things return to normal, I think it'll be appropriate to suggest a change of leadership. I suppose I'm okay when nothing is going on and all I have to do is pass out awards to school kids and make proclamations, but when it comes to insightful leadership, I'm a patsy." He held up his hand to stifle comments even though no one started to. "Finally, I got a call from Mike Martin today—he owns the car dealership. I won't be donating the SUV to the police department. The certified check that that guy wrote bounced. He said, in summary, that I need to pay up or he'll have to repossess it. He wasn't any happier about it than I am. Ordinarily it can take months for one of these checks to bounce, but he was suspicious of Waheed's demeanor, so he gave his bank a heads up on it, and it got expedited. Maybe he should be mayor. Ha. I never thought I'd say something like that about a used car salesman! But that's the deal. I'll deliver it to him tomorrow. I sure don't have $33,210 plus tax and destination charges."

Ennis Piceo
Ennis Piceo
105 Followers
12