tagNovels and NovellasJamaican Beauties Jaunt Ch. 09

Jamaican Beauties Jaunt Ch. 09


Chapter 9 - Risqué Tours: Her mother adds spice to the Jaunt.

Notice: The author listed Jamaican Beauties Jaunt under Literotica's umbrella category Novels and Novellas: Erotic fiction with a broader scope. However, the events in this chapter cover a variety of Literotica categories including:

Exhibitionist & Voyeur: this chapter includes the adventures of two beautiful Jamaican women wearing revealing clothing, driving topless, and posing naked for room service.

Interracial Love: this story is about a developing relationship between a Mulatto Jamaican woman and a Caucasian American man.

Mature: the story's primary characters are a young (26-year-old) woman and her Internet friend, a middle-aged (41-year-old) man.

Comments: All comments are welcome and appreciated. Please feel free to rate this chapter and to leave or send the author your comments. The author desires to become a better writer, to that end, your comments will help the author correct any weaknesses and reinforce any strengths.

Disclaimer: All characters portrayed in this story are fictional and were, to the author's knowledge, at least 18 years old at the time they engaged in any form of sexual activity mentioned in this story.

* * * * *

Risqué Dare

The previous week, as they were drinking wine and waiting for their lunches at the Frigate Pub after their salon visit and full body massages, Annika suggested Denise might consider offering some risqué activities during her Jamaican Beauties Jaunt to prove to Will she was not inhibited.

When Denise tentatively agreed, Annika volunteered to check a few places and to talk with some friends to set up a weekend vacation so they could visit each of the locations she had in mind. Denise asked her mother if she could set it up for early April and Annika told her, "I'll check and let you know by Wednesday or Thursday."

Thursday, during their regular daily early-morning phone conversation, Annika explained, "I'm waiting for a final confirmation from the hotel, but I'm confident we'll be able to start out next Thursday after you get off work."

Annika called Denise at work and told her, "I was able to schedule all four activities for the first weekend in April. I'll email you the schedule along with information on what you will need to pack."

That afternoon, after Denise arrived home and stripped off her clothes, she powered up her computer and, with her customary cup of tea, checked her Facebook account, and read her email.

She saved her mother's email for last. First, she scanned through the advertisements from web sites she'd once visited and mistakenly signed up to receive special offers. Next, she reviewed the jokes forwarded by her Internet friends and acquaintances. Finally, clicking on her mother's message, she took a deep breath to prepare herself for the details of her upcoming weekend with her uninhibited mother, while they checked on risqué activities.


From: Annika Johnson
To: Denise Johnson
Date: Thursday March 24
Subject: Risqué Tours Schedule


As I promised last Friday, I contacted some friends and scheduled several tours and adventures you might want to add to your Jamaican Beauties Jaunt. Our tour will begin immediately after you get off work next Thursday March 31 and end Sunday evening April 3. I think you will find these activities will prove to Will that "your Jamaica" isn't just for prudes.

The tour includes a visit to a world famous European-style beach that permits topless sunbathing, a clothing-optional snorkeling tour, sensual outdoor massages at a private mountain plantation, and a tour of a clothing optional beach resort. We will stay at a world-famous hotel and a fabulous and unique bed and breakfast. Below is the itinerary and packing suggestions. As I'm sure you'll be compelled to do, please feel free to pencil in the times.


- Lunch with your father at the Frigate Pub. You can ask him about the first time he and I met.

- Drive to the Villas on the Cliffs Hotel in Oracabessa.

- Tour the Villas on the Cliffs' facilities. We have a 6:30 PM appointment with Roberto Chavez, Hotel Evening Manager, at the concierge desk.


- Morning workouts in the hotel's exercise facilities.

- Breakfast at the hotel.

- Hotel shuttle to James Bond Beach for a morning of sunbathing and swimming.

- Meet with the VSO snorkeling trip manager and discuss the tours he offers.

- After lunch, enjoy a VSO snorkeling trip.

- Dinner at the James Bond Beach Restaurant. Our reservations are tentatively for 8:00 PM but the Maître D' will seat us when we arrive.

- After dinner (if you're up to it) we can go to Club Calypso X for drinks and dancing.


- Drive to Adam and Hilda's Cockpit Plantation outside of Falmouth (they run a private B&B in the middle of their coffee and banana plantation).

- Check in and hike to Adam's Eden, where we can change, (i.e., undress).

- Brunch with Adam and Hilda at the plantation house.

- Hike to Karen and Peter's for a sensual massage demonstration. We have reservations for around 1:00 PM.

- Dress (i.e., put on clothes) and hike to the Sandy Bend River Raft Pier for our Martha Brae River raft ride to the Green Goose pub for dinner. We won't need reservations.

- Taxi back to the plantation and hike to Adam's Eden.


- Breakfast with Adam and Hilda at the plantation house.

- Drive to the Sans Souci resort in Ocho Rios.

- Tour the resort and have lunch with Marilyn, an assistant manager at the resort.

- Spend an afternoon enjoying the resort's facilities, (i.e., its clothing optional beach).

- Drive to Kingston where we will meet your father at your apartment and go to dinner at a restaurant of his choosing. (He insists on taking us both out to celebrate my birthday.)

If you need me to make any changes to the itinerary let me know by tomorrow morning and I will do what I can. However, keep in mind; your father had to call in several favors to get us into the Villas on the Cliffs Hotel on such short notice.

Packing Suggestions:

Comfortable skirt, peasant blouse, and sandals for the drive.

Pack a short wrap-around skirt, lightweight blouse, and sandals. Cargo shorts and a tank top. Tube dress and stiletto-heeled sandals. Sturdy sandals that are comfortable and suitable for hiking in a wet environment, (i.e., Tevas). Stylish and appropriate workout clothes, (i.e., no sweats). Minimal makeup and any undergarments you think you must have for a risqué adventure.

A large beach bag with a small bikini or stylish and appropriate maillot swimsuit, i.e., no old-lady or old-fashion swimsuits, a beach cover-up, casual wrap skirt and loose pullover top (no running shorts or T-shirts), flip-flops or Beach Mocs, beach towel, and lots of sun block (SPF 35 or higher).

Looking forward to a revealing trip,



Denise sighed in frustration; her mother had scheduled them for four days and three nights of exhibitionism and nudity. She thought, "I wonder what she means by the phrases "where we can change, (i.e., undress)," "Dress (i.e., put on clothes)," and "enjoying the resort's facilities, (i.e., its clothing optional beach)? I'm afraid I know!"

Leaning back in her chair, Denise realized she may have been overconfident, may have made a mistake, when she agreed to spend a weekend participating in her mother's idea of risqué activities.

She sipped her tea as she considered the reason for the tour and finally said aloud, "I asked her to set this up. I told her I wanted to prove to Will that I'm no longer inhibited, and mother believes that taking him to places she considers risqué would accomplish that goal. Therefore, I will do anything and everything mother suggests during her little risqué tour. Besides, the price of backing out, in terms of my mother's and Will's teasing will be as bad, if not worse, than the costs of going through with the tours. So I guess it's, in for a penny, in for a pound."

* * * * *

Risqué Wardrobe

Denise printed her mother's email and reviewed websites Will had mentioned in the past in an effort to get ideas about the clothing her mother and Will would consider proper attire for risqué adventures. Once she knew what she wanted to buy, Denise dressed in a pair panties, but not a bra, a tan wrap around skirt, one of her father's old dress shirts tying the shirttails around her waist, and her tan, stiletto-heeled, sandals. Because she didn't want to carry a bunch of shopping bags and boxes home, she drove to a parking lot near the three stores where she had shopped for her Seven Progressive Challenges clothes. She knew that if she didn't show up with revealing clothes, her mother would tease her all weekend, therefore it was her intent to find and buy clothes similar to her mother's stated choices, but much more revealing.

Remembering her lesson from her earlier clothing purchases, she went to the store with the most revealing clothing first. She quickly found half-dozen sheer, milk-chocolate-colored, thong panties to bring along on her trip. She'd already decided it would be futile to take a bra along—her mother's email statement that she could pack "any undergarments you think you must have," meant only one thing. However, she wasn't as confident that she would have the nerve to do normal activities in public places without wearing underpants.

Next, Denise found a black one-piece swimsuit that would be perfect. While looking for a mesh cover-up, she spotted a white string bikini she knew Will would like and decided she should buy it. Finding a white mesh cover-up she liked, Denise decided to replace the black maillot with a white one. Thanking Will for convincing her to get a credit card, she charged the clothes and put the bag in her car trunk before walking to the store where she'd purchased her clothes for the challenges.

As before, the second store had clothes that were much more to Denise's liking. She spotted the clerk she had met and worked with twice before and asked for her help. Reading from her mother's packing list she decided to start with the blouses. It took a while but they finally found two short sleeve blouses and picked out a short, front buttoning, tie-waist wraparound skirt to go with them. The store clerk found a Khaki skirt and a matching loose fitting tank top that Denise liked.

Denise next told the clerk that she needed a slinky, black, evening dress and when they arrived at the racks of formal dresses, she saw exactly what she wanted hanging on a mannequin. The only problem was that the only similar dress in Denise's size was royal blue. The clerk, noting Denise's disappointment, promised she would find shoes to go with the gown. They combed the shoe racks and found a pair of Royal Blue sandals. The sandals had four-inch heels and buckled straps over the tops of the toes and around the ankles. While the clerk removed the gown from the mannequin, Denise found two other three-inch heeled sandals, one in brown and the other cream colored. With the items in hand, Denise headed, with the clerk and the rest of her selections, to the changing room.

It was then that Denise noticed the clerk was not dressed as modestly as she had been the two times before. While the clerk hung Denise's selections on a rack outside the changing room Denise asked, "Have you changed the way you dress?"

The clerk blushed and said, "Yes! You were my inspiration. You always looked so good and so comfortable in the sexy clothes you tried on, that I decided to try dressing like you."

"How has that worked for you?"

"I used to work all day and watch TV all night. Now I have a date every night this weekend," the girl grinned broadly.

Hugging her, Denise told the clerk, "I'm happy for you and proud to have been you're inspiration."

In the changing room, Denise removed her clothes, including her panties before she tried on the new clothes she and the clerk had selected. As she modeled them, Denise explained the purpose of each outfit, her objective in wearing it, and asked the clerk's opinion. The only change they made was to replace a lime green blouse for one in a cream color, the clerk noting, "The green doesn't really match the brilliance of your eyes, and your dark nipples will look wonderful under the sheer cream color of the mesh."

When Denise modeled the royal blue evening gown the clerk noted, "Normally, I tell my customers that a dress like that shows too much, but on you it's perfect. Wearing that dress, you can have any man you want."

"Great. Now I'd like to get one more outfit, something to wear around town. I want it to be pleasant to look at but not to attract too much attention. Can you help me?" Denise asked as, not bothering to use the changing room, she slipped off the evening dress.

"Yes, put on the shoes you wore here and wait, I'll be right back," the clerk chirped as she ran off to find an outfit she had in mind.

When the clerk returned, she told Denise, "This should get you some attention without actually stopping traffic."

Handing Denise a light brown, cropped-waist, tie-front, long sleeved, opaque blouse and a dark brown, wrap-around, hip-hugger, twelve-inch long, leather skirt, with a two-inch wide belt, and three inch overlap in front hiding an eight inch split, the clerk explained, "I wore a cream colored skirt and white blouse just like this to the club Saturday and no one complained."

Denise, in her heels, but otherwise naked, stepped into the skirt and pulled it up to her hips. She next slipped on the top, tied the long ties in the front of the blouse loosely around her waist. Sitting in a chair in front of a mirror, she was satisfied to see that the short skirt did not expose her waxed labia. Next, she tightened the knot on the blouse, stood up, and shook her shoulders. Again, she was pleased to see that although the blouse only slightly restrained her breasts it still contained them.

"Great choice, I'll take it and I'll wear it home."

"Excellent. It's always a pleasure to serve you," the clerk said with a grin on her lips and a leer in her eyes.

Denise charged her purchase and left the store carrying two bags of shoes and clothing and wearing her new skirt and blouse.

* * * * *

Risqué Preparations

Saturday afternoon Denise first packed her beach bag. It was the easiest; she first threw in her two new swimsuits, and the white mesh beach cover-up she found at the first store, her thongs (flip-flops according to her mother), her largest beach towel, a tube of Ban de Soliel (SPF 8) for tanning, and a bottle of Coppertone Sport Lotion Sunscreen (SPF 50) for protection. Finally, she found and tossed in an old wrap skirt and one of her father's white dress shirts that she used to wear around the apartment before the challenges.

"That was easy enough. Now, I need to make a check list from mother's email and gather all the items I need the pack in my carry-on bag," she told herself.

Denise spent the rest of the week putting her wardrobe together and preparing herself, physically and mentally, for her "Risqué Tour" with her uninhibited mother.

The Wednesday night before the tour was to begin, Denise, as a test to see if she was ready to do "normal activities in public places" while wearing her new clothes, dared herself to wear one of her new outfits to work. She settled on the skirt and blouse the clerk had chosen for her, knowing she had already worn it in public, albeit on a short walk to the parking lot while carrying shopping bags. She hung the skirt and blouse on the closet door so they would act as a reminder the next morning.

She decided that her concession to modesty at work and later at lunch with her father would be two safety pins. The first held closed the three-inch overlap that covered the eight-inch split on the front of the wrap-around skirt. The second pin prevented the knot in the tie-front, of her cropped-waist, opaque blouse from coming undone.

Thursday, the first day of her upcoming Risqué Adventures, Denise arose early, surprised to notice that she was excited about wearing her revealing skirt and blouse to work, and afterwards to the beginning of her risqué adventures with her mother. While enjoying her morning tea and checking her email, Denise mused that being naked in her apartment was one of her many exhibitionist behaviors that were holdovers from her challenges. Since she started the challenges, she no longer bothered wearing her nightgown, an old XXL cricket jersey, to bed and instead of or her old cover-up, one of her father's old tuxedo shirts, she usually remained naked while she was alone in her apartment.

After her shower, she put on minimal make up, brushed out her hair, donned her new outfit, and slipped into her brown, stiletto heel, sandals. When she'd tried on the outfit the night before, she'd neglected to put out a bra or panties. That morning she decided it was an omen and thus she should wear the outfit as she and the sales clerk intended, with only a pair of tan hold up stockings underneath and her heels.

As Denise stood before the full-length mirror on the back of her bedroom door she saw, in a moment of honest assessment, what her mother had constantly told her. She had her father's build, tall and thin. However, she had her mother's figure, a well-proportioned hourglass shape highlighted by large breasts, a nice bubble butt, and long shapely legs. She saw that she was indeed a taller, younger, bustier version of her beautiful, mulatto, Jamaican mother. She also saw that the clothes looked fantastic on her body and against her light caramel-colored skin and dark-brown, curly hair.

Her day at work was surprisingly uneventful. A few of the construction company's site managers visiting the office did double takes when they passed her office, but no one said anything. Her boss made his usual late morning stop after his coffee break and although he never ceased ogling her cleavage, his only comment about her clothes was to point at her breasts, grin, and stammer, "I-I-I like your... new look."

Her only problem was her concessions to modesty—the two safety pins that kept the split in the front of her skirt closed and prevented the knot in the blouse's tie-front from coming undone. They worked as she had hoped, except they each created an irritation. One scratched her thighs when she walked or shifted in her chair and the other constantly scratched her upper abdomen.

Three hours into her workday, Denise took a break, went into the building's restroom, and removed both safety pins. The walk to the coffee room and back to her office was the first time she'd been comfortable since putting in her "concessions to modesty."

"Well that's certainly a lesson in the benefits of living an uninhibited life," Denise thought as she returned to her office and sat at her desk.

* * * * *

That afternoon, when Denise arrived at her parents' house, Annika asked, "Denise, why did you change your clothes?"

"I didn't mother, these are the clothes I wore to work."

With a huge smile, Annika told her daughter, "I'm pleased to see you're trying to be more uninhibited."

"Thank you mother, I'm trying my best to follow your advice."

"But, did you remember that we're having lunch... at the Frigate... with your father?"

"Yes mother," Denise smiled, reveling in her mother's rare moment of discomfort, "I'm aware of today's schedule. I assumed that clothes good enough to wear to work would be good enough to wear to the Frigate. Do you disagree?"

Annika regained control and gave a small polite laugh, mostly at herself, "No Denise, I don't. I'm sure your clothes will be good enough for the Frigate. So if you're packed, let's put your suitcase and beach bag in my car and go to lunch."

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