David plunked his suitcase down on the bed. He’d put off packing long enough. Although to be fair, he wasn’t sure when he would have earlier in the week. He’d had to double up his lawn care bookings this week to make up for his trip, so if he needed any new clothes for the trip, today was the day.
Aside from his busy schedule, packing for this trip intimidated him. He wasn’t even sure where to start. He decided to pull up the resort’s website and see if they had any recommendations.
He’d never been on this kind of vacation before and wasn’t quite sure what to expect. His past beach trips had either been at the Family Shores Condo Complex at Myrtle Beach with his parents and grandparents or debaucherous weeks in Panama City with 6 of his frat brothers crammed into a motel room meant for 4. David suspected this would be an entirely different type of trip and would likely require an entirely different packing list. Sure enough on the frequently asked questions page, his suspicions were confirmed.
“What should I bring to Full Moon Coastal Resort?” read the question.
The page went on to answer itself, “That depends on what type of Jamaican Adventure you’re setting out on. At a minimum, you’ll want to bring swimwear, casual clothes for around the resort, and resort casual dinner wear for evenings. Gents, that means full-length pants, collared shirts, and closed-toed shoes. If you’re planning on taking advantage of any of our Caribbean Adventures excursions be sure to bring along clothes you can get active in, that you don’t mind getting dirty, and close-toed shoes that can get wet. If you’ve booked dinner at any of our Premium Gourmet restaurants, long sleeves and coats are required. When in doubt remember, whether it’s what you’re packing for out and about or what you’ll wear back in the room for your partner's eyes only, dress to impress.”
Well, that settled it. David was off to the mall. Sure, he could cobble together something that would technically fit the bill for most of the list, but it would hardly be dressing to impress.
While his wardrobe wasn’t exactly shabby, it definitely outed him as a college boy who hadn’t quite mastered the art of putting a cohesive outfit together. Somehow, he figured the stiff khakis, starched white button-up, and blue and red striped tie he pulled out at the end of each semester for his fraternity’s formal banquet wouldn’t quite knock Miss Kittren’s socks off walking into a “Premium Gourmet” restaurant.
Likewise, his swimwear didn’t seem like it would fit in this setting. When swimming next door at Miss Kittren’s pool he usually wore whatever shorts he’d been wearing for work that day. As far as actual swim trunks, his choices were his bright blue Bud Lite trunks, or another pair mimicking the blue and green floral pattern worn by Patrick Star from SpongeBob SquarePants. Both were baggy and cut below the knee. They both fit in fine at spring break down in Florida, but neither put forward the image of the young man he was hoping Amelia Kittren would see him as.
David groaned. It wasn't that he had any issue spending the money. Business had been good this summer, and it seemed like this would be the only expense he’d need to worry about for this luxury trip, but he was a bit intimidated at the prospect of having to pick all this out. How could he be sure what he picked would be any better than what he already owned. Normally, he’d ask Miss Kittren's advice in a situation like this, but she’d already been so generous in inviting him on the trip - not to mention the fact that, whether he truly admitted it to himself, part of his motivation was the hope, however much of a longshot it might be, that he would have a chance to explore some of his fantasies with his voluptuous host for the week. Asking her advice on how to best dress to seduce an older woman wouldn’t exactly be playing it subtle.
Then, as if an answer to his prayer, David’s phone rang. Ashley Bonpensiero’s name popped up, and David breathed a sigh of relief. Ashley was one of David’s best friends from High School. They didn't talk often after taking very different post-graduation paths, but anytime they reconnected, it was like no time had passed.
A petite brunette all-American girl, Ashley always seemed to have that sense of fashion that David lacked, and she wasn’t afraid to show it off. While David’s straight-A record earned him a spot in a prestigious business school, Ashley landed at a state school with an undeclared major. While figuring out her path, she started posting “Outfit Of The Day” videos on TikTok and amassed a sizeable following. Women watched to see her outfit, and men watched to imagine her outfit on the floor. That first summer, Ashley decided to let them do more than just imagine. She launched an OnlyFans account, and by Thanksgiving of her Sophomore year, she made enough every month through OnlyFans and brand deals to pay off the debt she’d accumulated in her first year of school and set aside enough to live on for at least the next few years to come. At Christmas, she dropped out and became a full-time model and influencer. By this point, almost two years later, she’d become a household name amongst the plugged-in social media crowd. It was strange for David to see his friends from school gawking at his best friend from back home on their phones - but always fun to watch their jaws drop when Ashley would come to visit him at school.
“Hey, Ashley!” David said, picking up the phone.
“Davie Boy - I’m in town for the weekend, any chance you’re free tonight?” Ashely chimed, greeting him by the familiar pet name she’d had for him since they were young.
David and Ashley had an incredible chemistry and everyone always assumed they’d dated or at least hooked up at some point in the past, but the truth was they’d always just been friends. Sure, there was heavy flirtation between the two, and a mutual admiration for the draw the other had on the opposite sex, but for whatever reason, the stars had never aligned in that way. They’d come close a time or two when a friendly hug lingered a bit too long and even shared a few drunken cuddles at parties over the year but fate had always kept them from crossing the line.
“Funny you should ask!" David replied, “Feel like going down memory lane and helping me pick out some new outfits to impress a lady friend I’m taking on a trip?”
Despite their chemistry, David and Ashley had always been very supportive of each other's sexual pursuits. In fact, David quickly learned that his dates usually went better when Ashley helped him decide what to wear.
“Wow!" Ashley laughed, “I’d have thought by now you’d have figured out how to dress yourself. Have I taught you nothing?”
“Oh no it’s just...” David stammered to explain himself.
“I’m just busting your chops.” Ashley replied, “It's always a pleasure to play dress up with my Davie Boy. You make a good mannequin and you take direction well. So, a trip? Sounds serious, why haven’t you introduced me to this lucky lady?”
“Well, it’s not exactly like that.” David sighed, “You actually have met her.”
He figured he should be honest with Ashley about his situation. She’d joined him over at Miss Kittren’s pool many times over the years and had often caught him stealing glances at their host. Ashley would tease him about it from time to time, and David would make no attempt to deny that Miss Kittren made him weak in the knees. In fact, Ashley may have been the only person to whom David had ever divulged the extent of his crush on his neighbor.
David explained the entire situation to Ashley, who was dumbfounded.
“Well damn, Davie Boy!” Ashely exclaimed, “A week in Jamaica with Miss Kittren. You really hit the jackpot with this one. I’ll be right over. I’ll take a look at what you have so far and then we’ll hit the mall. If I had to guess, we have a lot of work to do.”
Ashley arrived in no time. A quick review of the dress code and David’s closet confirmed that almost nothing he had would do. This would be Ashley’s biggest task with him yet - but she was up for the challenge. They headed out to the driveway, where David saw a familiar minivan parked. For such a hot young thing, Ashley definitely drove a mom car. It actually had been her mother’s car for years before handing it down to Ashley and upgrading to something nicer for herself.
Getting into the van, David realized Ashley had finally made good on one particular upgrade she’d talked about for years. Ever the tease, Ashley was quick to let prospective dates know that, if she really wanted to, she could take the back two rows of seats out and fit a twin-size mattress on the floor of the van, but to David’s knowledge, she’d never actually tried it until now.
“So the mattress actually does fit?” David jokingly asked, “Does this mean you finally found the guy worth lugging the backseats into your parent's garage for?”
“I wish!” Ashley replied, “I could use some backseat action. No, I’m getting ready to start a cross-country content trip in a few weeks. Van living is all the rage on Instagram now. I’ll stay in hotels and AirBnBs along the way, but I’ve got to keep up appearances for my followers that I’m staying and playing in the van.”
“Hmmm,” David chortled, “your life never ceases to fascinate me. You’ll probably make more money in 2 weeks sleeping in your car than my business will make all summer.”
“You know it Davie Boy!” Ashely sniped back, “Enough about me, we’ve got some shopping to do!”
Strolling into the mall, they hit all the familiar spots. For resort casual, they found some lighter slacks and linen shirts that would feel more at home in the island setting. Modeling the new look for Ashley outside the fitting room, she took note of her friend’s improved physique.
“Davie Boy,” she remarked, “Another summer behind the mower has done you well.”
Never shy, Ashley unbuttoned one more of David’s top buttons, telling him, “Don’t be afraid to show off a little chest hair. And, speaking of showing off, let’s see this same shirt a size smaller. With a body like yours, it’s a shame to hide behind ill-fitting clothes.”
David turned red. It was true, he always wore his clothes on the looser side, feeling self-conscious when he could feel the fabric tugging at him, but he decided to trust his friend and give it a try.
After a trip back out on the sales floor and a quick change into the new size, David emerged again.
“Much better!” Ashley grinned, “just don’t forget to keep those top buttons open. Let it breathe.” Reaching up again to adjust his buttons, Ashley’s hands lingered a few moments longer and then slid over to his arms.
“Easy,” David warned jokingly, “this show isn’t for you, remember?”
“Of course,” Ashley smirked, “Come on, we can get these in a few different colors and styles for resort casual but we still have a lot of work to do.”
Working their way through the mall, David and Ashley worked their way through the packing list: A few slim-fit dress shirts and silk ties for the formal dinners, new shoes and sandals for various footwear needs, v-neck t-shirts that hugged David’s muscles far better than anything he had worn before, and a few pairs of thigh-length chino shorts for around the resort. Ashley even provided a few pointers for David on things that may subtly get Miss Kittren to see him as a prospective mate: new boxer briefs that accentuated his ample package just right to give it even more shape and definition, and a pheromone cologne that Ashley claimed she found so nice that just a few whiffs was enough to get her nipples hard and her pussy wet. David just hoped it would have a similar effect on Miss Kittren.
“Do I need Pajamas?” David asked. He usually slept nude at home and for traveling with others he had some fleece Joe Boxer lounge pants that definitely wouldn’t do in the Caribbean.
“That’s what the extra boxers and v-necks are for, silly!” Ashley snapped back, “Put the goods on display for her!”
That seemed a bit bold for David, but if he was going to get what he wanted out of this trip, he'd have to be bold.
They were down to one final item. Swimwear. Walking back to the swimwear section of yet another department store, Ashley pulled a few options for David. Solid colors and basic patterns, much more mature than David’s Bud Lite trunks. She pulled out one option that David thought had to be a joke. It was a more European cut that barely came down below his ass. Trying it on in the fitting room, David filled it out well. If it had been any shorter the tip of his cock would peak out the bottom. It seemed like a lot of skin, but then again Miss Kittren had shown him a lot of skin over the years in her bikinis. The least he could do was return the favor. He walked out to get Ashley’s opinion.
What he had failed to realize was that thinking of Miss Kittren in her bikini had once again given David a firm erection and the tight swimsuit hid nothing.
“Damn, Davie Boy you really are packing!" Ashley laughed, “I think from now on I’m gonna have to call you Davie Man!”
“Haha - is it too much?” David shyly replied.
“Not at all!” Ashley quickly replied. “Trust me, you’ll see plenty of other guys in these on the beaches in Jamaica. Probably some even shorter and tighter. Baggy trunks are a thing of the past - or at least they should be for anyone over sixteen.”
“I’ll take your word for it. Shall we head to the register?" David asked, hoping to make it out of the changing rooms before anyone saw him with such in gutsy look.
“Not quite,” Ashley said, “While you were in there, I found something for myself. I think I’m gonna wear it for a photo set on my page, but I want to get your opinion, if you don’t mind. Go get changed, and I’ll try it on and show it to you when you come out.”
David was happy to take a look, but Ashley asking for his opinion on clothes did give him a bit of a laugh. She was so fashionable, what did she need his advice for?
Stepping back to the changing room, he took a little bit longer than usual changing back into his street clothes, to give his erection time to subside. When he finally felt relaxed, he gathered his things and exited back into the lounge. What he saw on the other side of the door caused his jaw to drop and his cock to once again stand at full attention.
Miss Kittren’s bikinis were usually a classic pin-up style. They certainly showed off what she had to work with, but they required a good deal of padding and support to hold her heavy naturals in place. By contrast, what Ashley had on was best described as three small triangles of shiny purple fabric, each no bigger than a post-it note, held together by string only slightly heartier than dental floss. It made sense, Miss Kittren had ample assets to support while Ashley’s petite twenty-one-year-old body was still pert and perky, supporting itself, while the minimal fabric left almost nothing to the imagination. Both shapes and styles were incredibly alluring in their own ways, and David was more than happy to examine both in great detail.
Glancing down at his cock Ashley devilishly said “Well, there’s our little friend again. I guess he likes it! That’s all I need to know. Give me a minute, I’ll get changed and we’ll head for the registers.”
The checkout and walk to the car were fairly quiet. David struggled for words. It wasn't often he was left speechless but seeing Ashley nearly nude, moments after her remarking on the size of his cock did just that. Back in the car, Ashley started needling her friend about his coming trip.
“So Davie Boy, be real with me,” she began her interrogation, “You swear nothing has happened between you and Miss Kittren already? This trip just fell into your lap”
“Pretty much,” David replied, and once again recounted the whole story Miss Kittren had told him regarding the circumstances of the trip.
“So as far as you know, she has no plans for any funny business on the trip, just a relaxing weekend with the twenty-one-year-old neighbor boy?” Ashley doubled down.
“Well - I’d be lying if I said I hadn’t considered it or thought about how I could make it happen, but as of now we’re just two friends going on vacation together,” David explained. He was somewhat confused by the line of questioning.
“Got it," Ashley said somewhat definitively, "then Davey, I just have to say, you need to be careful or you’re going to put that poor woman’s eye out with that monster cock of yours”
“Excuse me?” David burst out, shocked by Ashley's blunt statement.
“I’m just saying we were at the mall all of about 3 hours and you've been walking around looking like you overdosed on Viagra every time Miss Kittren comes up. You need a release before this trip or I think you’re going to explode.”
“Very funny!" David snapped back, "I’ve been trying. I’ve been jerking off nonstop this week, practically rubbed my cock raw, but as soon as I cum, I think about the week ahead and I’m stiff as a board all over again”
“That’s not what I’m talking about. You need the real thing,” Ashley said, pulling into a parking lot that David didn’t recognize. “You swear, you and Miss Kittren are just friends, nothing is going on between you two…yet?”
“Yes,” David replied confused.
“Then let’s cut the bullshit," Ashley said, as she shut off the engine, "I’ve spent all afternoon pawing you up and down and looking at that ladykiller in your shorts, while you drool over your neighbor lady. I’m not saying you don’t have a chance with her, but that’s tomorrow in Jamaica. Today you’re here. You're single. I’m single. We’re both horny as hell, and I have a mattress in the back of my van. Are you following?” With that, Ashley slid off her shirt and shorts revealing she was still wearing the skimpy bikini from before.
David was briefly conflicted before deciding Ashley was right. He didn’t owe Miss Kittren any fidelity yet - and he’d certainly enjoy a chance to fool around with Ashley before setting off on his trip. While he'd never actively pursued her, David always enjoyed a good long look at his friend in her skimpy outfits. She had a body to die for and she was throwing herself at him. He knew he’d have to work much harder with Miss Kittren in the week ahead, and decided this might help calm his nerves.
Turning to face Ashley, their lips met and their hands began to wander. Ashley’s hand wandered under his shirt and felt David’s muscles up and down, taking every moment to enjoy the fruits of his summer of labor. Likewise, David treated himself to a handful of Ashley’s bubble butt and it's youthful firmness. Before long, their playful exploration turned to an animalistic groping, fumbling for pleasure wherever it could be found.
Tiring of armrests in the way, David and Ashley contorted out of their seats, and into the mattress in the back of the van. Ashley’s hand reached into David’s shorts and wrapped around his cock. David instinctively thrust himself forward as he shuttered with satisfaction at the sensation.
“Now, that I have you where I want you, just a few ground rules,” Ashley said “This is for today and today only. We’ve got a good thing going and I don’t want to ruin it. I’ve always been curious what it would be like to be with you, I’m sure the same goes for you. After today, you go back to chasing Miss Kittren and I’m going to go back to enjoying whatever cock suits me. We’re going to swap sexy stories with each other and there won’t be any jealous bullshit. Today is just two horned-up friends helping each other get their rocks off, deal?”
At that point, David would have agreed to anything, but it didn’t matter. Ashley had said everything that had gone through his head in his brief moment of hesitation.
“Deal,” David affirmed.
“Good, because I need this” Ashley signed, slightly loosening her grip and allowing her soft silky hand to slide down his shaft. “I’ve been looking at you in those new tight clothes all day, hoping I’d get a taste before you left town.”
Ashley released her hand, allowing David to wriggle out of his shorts. She crawled down to the other end of the mattress and David guided his cock into her mouth, firmly petting her on the back of the head.
“Then taste away," he whispered to her.
Always a bit more of a free spirit than David, Ashley had a bit more experience between the sheets, and it showed. She expertly took him all the way into her mouth without pausing or gagging and bopped her head up and down without missing a beat. David could have settled for this masterful oral performance, but he knew Ashley wanted more.
He gripped her hair by the back of the head and pulled her off his cock. Looking down at her, he motioned with his finger for her to come back up to lie next to him. She laid back on the mattress and spread her legs, and David quickly climbed on top of her and positioned himself to enter.
“No going back. Show me what that big cock can do Davie Boy," Ashley teased him, "show me what Miss Kittren has waiting for tomorrow.”
That lit a fire within Davey. Ashley's sweet pussy was already dripping from the scent of his cologne and with one thrust he slid right in, basking in the euphoria of her tight slit. The warm pressure made him shudder. He looked down at the slender body so many men had paid online to just glance at online and felt a sense of pride, as though he'd conquered something almost mythical. He thrust into her over and over, pinning her down onto the mattress as he released weeks of pent-up sexual frustration.
Ashley's eyes rolled back into her head. She struggled to speak, barely getting out, “That’s it Davie Boy, fuck me hard, make this van shake. Oh yes.”
David knew he couldn’t hold on much longer. He pulled out, kneeled over Ashley, and stroked his cock until his load spurted out of him, covering her perky little tits in a thick glaze.
“Damn - I needed that,” David said, feeling his head clear for the first time in a week. He fell onto the mattress beside Ashley.
"Me too! Thanks for helping me break in the new mattress," Ashley said, smirking. She continued, "If things don’t work out with Miss Kittren, let me know. I meant what I said, that I don’t want this to make things weird, but as long as you can keep to that, I’m always down for a casual fuck. If things do work out, and she’s as freaky as I hope she is, let me know that too. A three-way with the two of you sounds like heaven. I'd love to get my face between those tits she's rocking. Now let’s get cleaned up and get you home,” Ashley said reaching for the towel she kept stashed at the foot of the mattress for just this type of occasion.
"You’ve got a plane to catch in the morning!" Ashley quipped, wiping herself down.
A few hours later, David sat on his bed, fully packed for the day ahead. His phone buzzed.
“Thx for the good time, ur gonna knock it out of the park with Mz Ktn stud! See you in a few weeks," the text from Ashley read.
David smiled. He was glad he’d gotten a little action before his trip and was certainly glad Ashley had helped him figure out what to wear to impress the true object of his desires.
His phone buzzed again. This time it was from Miss Kittren.
“All set for tomorrow? I’ll pick you up at six A.M. and we’ll head for the airport. See you soon ;)”
And just like that David’s erection returned, as he tried to get a little sleep before heading off for what he was sure would be one of the best weeks of his life.
