First Day in the Caribbean 24

Story Info
Almost everybody gets it on! More or less.
5.5k words
4.53
14.2k
3

Part 31 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
104 Followers

Charlie and Bill meekly followed Jenny and Karen upstairs, pretending to have only academic interest in the tour. The girls led them up, pretending to be excited about showing off their decorating skills.

"So anyway, see?" began Jenny, waving her arm. "Like downstairs, but we have a smaller great room because there're two more bedrooms, currently vacant, though it's where Asch and Octavia rented when Lydia was here. We got the two that used to be rented by some people I never even met!"

"We'll show you them in a minute, after Jenny cleans up her room," smirked Sharon.

"Hey! You're the messy one," Jenny retorted.

"Shh! I don't want anyone to find out," Sharon kidded. "Anyway, see this trapdoor in the ceiling? It goes to a storage area, where Lydia keeps her telescope, then to the roof. We can take a look. The view is spectacular."

Bill pulled the rope that lowered an attic staircase and settled it into place. "Wish I had some binoculars," said Charlie. "Say! That's what I can spend my leftover picture money on!"

"I have a pair you could borrow, if I had brought them along," offered Bill. "Maybe we can make another trip up here sometime."

"Well, quit talking and get up there. The view is pretty good naked eye, too," and Sharon gave Bill a push.

So they climbed the stairs, one at a time. The storage room was a little crowded, especially since they didn't want to bump the telescope, but they managed to climb the ladder onto the roof without messing it up.

It was dark enough that they could hardly see each other, which was actually fine with everyone. They surveyed the horizon, naturally forming into two couples. The sky glowed to the west because of the town, and barely glowed to the east because of Easthaven. But the sky overhead was, indeed, spectacular. The Milky Way stretched across the sky like a narrow band of mist. Hundreds of stars speckled the sky, and two particularly bright ones Charlie suggested might be planets. They made a contest of pointing out constellations, but they were pretty evenly matched; none of them were astronomers. A meteor streaked across the sky, and Jenny said, "Make a wish!" They didn't know it, but everyone wished for a chance to get away from the other couple.

They ended up on opposite sides of the walk, pretending to watch for more shooting stars. Both guys stole a kiss from his girl. Sharon wrapped her arms around Bill and turned the kiss into several, with lots of body contact. Jenny was a little more reserved, but she and Charlie exchanged several kisses. Jenny smiled contentedly, then whispered, "You've gotten better. Been practising?"

Charlie turned invisibly bright red. "Um, what if I have?" he hedged.

Jenny chuckled and whispered, "Whom do I need to kill?" and gave him a lengthy, open-mouth kiss.

"Nobody, but I'm sure glad I improved," he whispered back.

Jenny spoke aloud, "I'm getting chilly. You guys look for meteors all you want. Charlie and I are going down where it's a little warmer. I won't let him see your room." You could hear the tease in her voice.

"See you in a few."

Charlie and Jenny clambered down the ladder, Charlie leading. At the bottom he made as if to support her the last few steps and it turned into a hug with his arms just under her breasts. Jenny put her arms over his, then lifted his hands to her breasts before raising them in the air so she could turn around. She kissed him. "Let me show you my room," and she led him down the rickety stairs and toward her room.

Inside the room she pointed out some of the decor while he pretended to absently shut the door. She approached him, ostensibly to point out the poster on the back of the door, and he grabbed her, pulling her into him. She stopped mid-sentence to respond to his kiss. He slid his hands under her top and slid them up her back.

"Are you being aggressive?" she asked.

"Yup."

"Good!" and she slid her hands under his T-shirt and ran her fingernails up his back.

Charlie debated whether to slide his hands around to her front, but she decided for him by raising her arms, inviting him to slip the top off entirely. Which he did. She wiggled and stretched. "Ah! Free at last!" She made a wicked face. "Now let me do yours." He raised his arms, and she dove for his ribs to tickle him.

"Hey! Good thing I'm not too ticklish," he gasped. The T-shirt came off and they looked at each other for a moment before coming together for some more kissing.

Jenny ground her hips into him and could feel his hardness. "Let's snuggle on the bed, shall we?" She tossed her head and backed up, leading him by both hands and letting him feast his eyes on her slim figure. When she reached the bed, she fell backwards onto it, arms out, knees somewhat apart. The only thing she was wearing were short shorts.

"Would you like me to be aggressive again?" he asked, stepping closer.

"Thought you'd never ask, but if you take anything off me, you have to take it off you, too."

Charlie reached for her waistband and pulled, revealing a slim triangle of hair above her pussy. He forced himself to look into her eyes and unfastened his own shorts, then let them drop. Her eyes widened when she looked down at him, erect and eager. "Ah, free at last!" he quipped.

She smiled. "Come here, big guy. Next to me, so we can snuggle," and she patted the bed.

Charlie was tempted to just dive between her legs, but there's good aggressiveness and bad aggressiveness, so he climbed onto the bed next to her, on all fours, member hanging conspicuously.

Jennys eyes were riveted on his manhood. "Can I touch it?"

"Thought you'd never ask." He shifted so he was at an angle to her, a hand on each side of her rib cage.

Gingerly she reached down and took hold of him.

It was the most wonderful thing Charlie had ever felt in his life, and he nearly climaxed right there. He gasped, and she immediately let go.

"Did I do something wrong?" she looked concerned.

"Ohnonono, It was, uh, wonderful. Exciting. The biggest turn-on of my life. If you had held on a second longer I'd have exploded all over you."

"I thought it took longer." She wrinkled her brow in puzzlement.

Charlie heaved himself up so he was kneeling. "Maybe if I get used to it, but right now if you do anything, well, I'll think I died and went to heaven."

Jenny smiled, staring at the penis pointing so directly at her. "Well, I want you alive for a while at least. If I behave, do you want to be a little bit aggressive with me?"

Charlie gave a shaky sigh. "I'd love to. Tell me what you like and don't like. Suppose I start with a back rub, only on the front?" He reached for her shoulders and gently ran his hands down her chest to her belly.

Jenny closed her eyes in pleasure. "Yes. Do that some more. I like how gentle you are."

He experimented with different strokes, making circles on her breasts, playing with the nipples, stroking her belly, working toward her crotch. When she spread her legs in encouragement, he continued down, passing his fingers softly over her mound. He hitched himself so he was at her waist facing her. He continued with the one hand at her vulva, and stroked her cheek with the backs of his other hand's fingers. When he got to her chin, she turned her head and began to suck on his finger. Charlie didn't know what to do, so he concentrated on her pussy, doing his best to caress her cheek and chin with his free fingers. Her slit was wet, and when he pressed a little, his finger slid right in, He left it in a little and stroked slowly up and down.

Jenny began to moan, arching her back and hips, meeting his strokes with her own movements. She began to toss her head from side to side, and Charlie moved his hand down to a breast, squeezing gently, sometimes pinching the nipple. Her moans grew louder, so he moved his fingers in her slit more aggressively Suddenly she yelled "AAH! UH! OH!" and trembled reflexively. Again suddenly she reached over and grabbed Charlie's penis and pumped vigorously. It took about three strokes before he convulsed, bucking and spewing all over her arms and belly.

She fell back, heaved a big sigh and smiled up at him. "Let's do that again." She scowled a little. "But not right now. I'm—exhausted. No, satisfied. Done."

Charlie knew how she felt. He reached over and grabbed his T-shirt from the foot of the bed and offered it to her. She absently wiped herself off, looking at him. "You willing to do it again? For real next time?"

Charlie laughed. "Is water wet? Are we on an island? Are you the most beautiful woman in the world?" He rested his hand on a breast.

"Well, I don't know about that last one, but I guess that's a 'yes,' I guess."

"You said 'I guess I guess.' " He smiled and leaned over, and kissed her.

She returned the kiss, but had a look of concentration on her face. "I can think of so many variations I want to try. Maybe we should make a list."

Charlie rolled his eyes. "Whatever you want, my dear. I'm at your service." He gave her a suggestive look.

It was Jenny's turn to roll her eyes. "Okay, lie here next to me and help me think of what to put on our list."

So he did.

——————-

Up on the rooftop, Sharon was leaning back against Bill, his arms around her while they pretended to look for meteors.

Bill nuzzled her neck. "Should I put my hands here," and he cupped her breasts underneath her blouse, "or here," and he moved his hands down toward her womanhood.

She wiggled her hips. "Too bad you don't have four hands. Three hands." She moved her feet apart. "Last weekend in the water was fun."

"I agree."

"Y'know, I think Jenny was only pretending to be cold. I think it's perfectly nice out. But I'm getting a crick in my neck looking for these shooting stars. Let's get on that cushion to look."

Sharon lay down on her back, hands behind her head, knowing that the position of her arms enhanced her figure. She took a deep breath for that reason, too, as Bill settled next to her, on his side, facing her. "You're not looking up at the sky," she pretend pouted.

"Plenty of stars in your eyes," he said, smiling.

"Oh you're such a romantic, aren't you?"

He smiled and leaned over to kiss her. The kiss turned into several, which had been happening a lot that evening. He felt her move, and discovered that she had begun to unbutton her blouse. She left it over her breasts and returned her hand to its place under her head. He brushed the fabric aside, exposing her breasts for kisses, then he let his hand drift downward, and she made "mm's" and wiggles of enjoyment as he moved his hand over her mound and tongue over her nipples. She managed to get her close hand into his lap and played with his hardness through his shorts. Eventually he unfastened the button at the top of her shorts so he could get his hand inside.

"I have a confession to make," she murmured. "I'm a virgin."

Bill withheld his surprise. He had at first thought that she was going to confess that it was her period, but this was unexpected.

"I like to flirt and lead guys on, but somehow I never got into bed with anybody. Maybe people were afraid to bonk the mayor's daughter. I dunno." She let go of him and unzipped the little zipper on her shorts, then wiggled out of them. She put her hand back in his lap. "Maybe I'm not attractive."

Bill chuckled. "Fishing for compliments, are we? You're gorgeous. Stunning. Guys look at you and walk into telephone poles."

She smiled at the image and gave him a squeeze, which made him jump a little. "You like how I flirt?"

"Do I ever." He paused. "I have a confession, too. He paused several moments. "I am also a virgin. Never had sex with a woman."

Sharon didn't withhold her surprise. "What! You seem to know how to please a woman—me anyway—that's for sure. How come? Never?"

"Well, I've just never had any luck trying to land anyone. Maybe because it's because I'm bald and have a big nose. Not built athletically. Smell funny? Don't know. Women just don't look at me twice."

Sharon rolled toward him and made a big sniff. "Grrowff!" She smiled. "No smell problems. I've always thought of you as experienced and wise. Baldness never entered into it. At least you don't do a comb-over. Means you're not vain. Which I also like. Um, do you know what to do?"

"Well, in principle." He gently placed his hand on her mound, resting his middle finger so it slightly entered her slit. It was already pretty moist. "I've read several books, watched some movies. So I know what goes on, but it's all, uh, academic."

Sharon smiled. "Well that makes two of us. It's supposed to hurt the girl the first time but I haven't heard whether it hurts the guy."

"I don't think so, but I'm willing to find out. I'm pretty sure I'll be okay as long as you don't squeeze my balls" He smiled. "How does this feel?" He drew his finger up her slit.

"Exciting," she murmured. "Go a little deeper."

Soon he was stroking her clit and inner lips, and she was moaning with pleasure, squeezing him through his shorts, which made him moan with pleasure. Then he found her opening and experimentally pushed the tip of his finger in.

"Hmm. It's kind of tight. I can feel it pulling, or stretching or something," she said.

"I don't think it's quite big enough for more than my finger."

"Of course not, dummy! That's how I get to not be a virgin. You plunge into me and rip me open!"

"You put it that way,it sounds kind of barbaric. Maybe that's why rape sounds like rip."

"Well, it's not rape if I'm conscious, not drunk, and willing." She gave him another squeeze. "Why don't you take those shorts off?

He carefully removed his finger and struggled out of his shorts. "Want to try it, see how it is?"

Sharon wrinkled her brow. "Hmm, I'm lying here naked, legs spread, with a guy who I just told to take his pants off, a guy who I happen to like and who appears to want to be gentle with me, um. —Yes!"

He got up, kicked the shorts out of the way, and kneeled between her legs. They hitched themselves closer together, and she guided his member toward her opening. Bill slid the tip up and down her slit, wanting to get her excited again, and he succeeded. Her moaning increased, and presently he pushed her opening, slowly pressing harder and harder. Then he chickened out and backed off a little.

"Do it again." So he pressed into her again, a little harder. Suddenly he was inside, and she gasped. "Don't pull out. Stay there." she demanded. So he did, until she started to move a little at a time, then more and more. "Can something hurt and feel good at the same time?"

Bill was on the verge of coming. She was so tight, hot, and wet. Experimentally he began to match her thrusts and she thrust back, harder, encouraging him. "Uhh, I can't stop," he moaned.

"So don't! Do me!"

He thrust hard several more times, climaxing so hard he fell forward onto his hands squinching up his face and gasping. He opened his eyes to see Sharon looking into his, smiling a little. "You liked that, huh?

"Ah yes." He kissed her, then kissed each breast. "Next time Let's concentrate on you having fun."

"Oh it was fun just watching. Next time I'll be healed and none of it will hurt, right?"

"If I have anything to do with it, it won't."

"Well, I don't plan on giving anyone else the chance."

Bill carefully backed out, then reached over and pulled a hanky out of a pocket. "Want this?"

"Ooo you're prepared! See how wise you are?" She smiled and wiped her crotch, making a bright red stain on the hanky. She sighed. "Guess this is my first laundry for us, eh?"

Bill stood and pulled on his shorts. "Do you feel okay? Anything I can do?"

She reached up so he could pull her standing. "You could hand me my shorts." She made no effort to gather her blouse as if her nakedness was the most natural thing in the world.

Bill grabbed the shorts and kneeled, holding them so she could step into them, then he pulled them up. She took over and did the zipper and snap at the top. She grinned at him. "All ready!"

"First I want to kiss you again," and he took her in his arms and the kiss, as usual, turned into several. As they began to head down, he asked, "Um, don't you want to do your shirt?"

"Not really. I'm a flirt, remember?" She spun around in the narrow storage area, arms straight up, displaying the curves of her torso in the dim light.

He shook his head. "Woman, I don't think I'll ever not have an erection when you're around." He grabbed her and they exchanged a bunch more kisses. He backed down the stairs planning to get her to back into his arms when she came down. What happened, though, was that she came down the stairs forward, shirt open, then fell into his arms from the last step, her arms wide. He caught her and nuzzled her neck.

"Lemme quick show you my room." She broke away and led him to her bedroom. It was neat as a pin.

——————-

"Why don't you guys get in here with us?" Rick asked. Troy and Lucy had ridden in the back of Rick's beat up pickup coming up to the event. "It's getting cool and it might be cozier in the cab."

Cozy was right. Lucy sat on Troy's lap, and Karen scooched closer to Rick, putting one leg on each side of the floor shift and her hand on his leg. All four of them enjoyed the ride back to town. All four had shorts on. Karen was pretty adventuresome about where she ran her hand on Rick, and Rick followed suit, using the excuse of needing to operate the shift lever. Lucy wiggled her behind on Troy's lap and inserted her hand between them, ostensibly to scratch her posterior, but she left her hand there and clenched her fingers on Troy as soon as she could feel his hardness, which didn't take long. Troy kept his hands on Lucy's legs, pretending to hold her secure, but finding the occasional opportunity to run his thumbs under the cuff of her shorts. Conversation started out animated, then dried up the closer they got to town.

When they pulled up to Lucy's place, she and Troy hopped out, said a quick goodbye and thanks, then trotted into her apartment without looking back. For her part, Karen stayed seated where she was and got even more adventurous with her hand in Rick's lap. "Let's see—the apartment is closer than the store. Get my drift?" She gave him a squeeze.

"Like a high wind pushing a boat sideways," he replied, and stepped on the gas.

Troy followed Lucy into the apartment. "I'm glad the week's over. Well, sort of. I'm sorry I had to spend so much time at the recruiting center, but at least I got this extra weekend out of it so I got to see you again." He paused, turned a little red, and said "I, um, stopped at the drugstore and bought a raincoat."

Lucy frowned in puzzlement, then the light dawned. "Ha ha. So did I, only I didn't call them raincoats. What kind did you get?"

He reached in and fished a pack of condoms out of his pocket and handed it to her. "What kind did you get?"

She looked at his offering. "Thin skin studded! I don't believe it. I got the same kind!"

"I didn't know what to get, so I asked the pharmacist which were the best and that's what he suggested."

"I did the same thing. Did you go to Pfamily Farmacy by chance?"

"Um, yeah! You too? Ha. I wonder if he put one and one together." They both snickered at the thought.

"Well," she said. "This is a three-pack. Let's waste one and see what they look like." Gingerly they opened a packet and carefully withdrew the little circle. "Eww. It's greasy."

Troy was reading the package. "Prepared with natural-feeling lubricant for greater enjoyment and sensitivity." He read aloud. "Place over end of erect penis and unroll. Pinch the end when starting, to create chamber for ejaculate. Avoid sexual contact until condom is in place." He snorted. "I can tell which part was written by marketing and which by a tech writer."

Ennis Piceo
Ennis Piceo
104 Followers
12