tagNovels and NovellasJamaican Beauties Jaunt Ch. 03

Jamaican Beauties Jaunt Ch. 03


Jamaican Beauties Jaunt: Beaches Aren't the Only Jamaican Beauties.

Jamaican Beauties Jaunt includes a variety of categories in addition to its primary category of Novels and Novellas. The actual or implied categories in this chapter include: Exhibitionist & Voyeur -- a woman is dared to publically expose herself, Interracial Love -- a Mulatto Jamaican woman and a Caucasian American man, Mature -- a 26-year-old woman and a middle-aged, 41-year-old, man; and Romance -- although at this point in the story the primary characters are Internet friends.

All of the characters portrayed is this story were at least 18 years old at the time they are described by the author as having engaged in any form of sexual activity. However, neither the author nor the characters can or will vouch for any activities in which the characters may have participated outside those described within this story.


Chapter 3 -- Villa Ronai: Denise poses publicly dressed more revealingly.

Wednesday evening after arriving home from a long day at work and a hard workout at the gym, Denise received her third challenge. When she saw that the subject of the email was "Third Challenge: Tourist Spot sans Bra," she hesitated. Although she'd spent the last two evenings relishing the memories of her excitement while completing the last challenge, the thought of going out in public without a bra, not to mention while wearing the diaphanous tan blouse, still worried her.

"Okay," she confessed aloud, "Now that it will soon become a reality, it scares me!"

She remembered and repeated her mother's question to her as she considered whether to take the challenge, "Why bother taking the challenge if you're not willing to do everything possible to win it?"

Emboldened with her mother's intended inspiration and her exciting memories and dreams from the previous challenge, Denise's trembling finger pressed the mouse key to open the email and display the message contents -- the third challenge. As she quickly read it, she could see it was the dare she'd imagined.


From: Will Kruger

To: Denise Johnson

Date: Wednesday November 3

Subject: Third Challenge: Tourist Spot Photographs (sans bra)


As I mentioned in my acceptance of your accomplishment of your second challenge, I was, and still am, concerned that you regressed from the first challenge and opted to wear a bra for your second challenge. Please remember, the purpose of the Seven Progressive Challenges is for you to progress towards your goal, in this case to become more uninhibited, while you learn to overcome any obstacles, recognize when you are regressing, and to take steps to prevent that from happening. Therefore, for your Third Challenge you will again need to wear the outfit I approved for your first challenge, with the top three buttons of the blouse unbuttoned, with your blouse tucked into your skirt and pulled tightly over your breasts, and without a bra, camisole, or any similar form of breast covering.

For this challenge you will again need to go to a well known tourist spot of your choosing (preferably a different location than the one you use for your second challenge), and you will either ask a stranger to, or preferably, have someone you know, take the photographs of you posing at that tourist spot, wearing your new outfit while clearly not wearing a bra or similar undergarment.

Your proof will be at least three photographs showing that you are wearing the new clothes, obviously without a bra, while at an identifiable tourist spot. Again, as you did for the first two challenges, I would also like you to provide a summary of your journal entries about your feelings as you prepared for, performed, and completed the challenge.

In light of your regression in the second challenge, I asked the Societe Internationale de Defis Progressive for permission to place a time limit on this challenge. They agreed to my request and therefore, you have one week (seven days) from tomorrow to submit your proof and obtain my acceptance of your successful accomplishment of this challenge. If you cannot provide acceptable proof that you accomplished this challenge within that timeframe, the society will disqualify you and deem you to have failed the challenge.

Your Disappointed, but Optimistic, Challenger,



She mumbled to herself, "So this challenge is obviously intended to force me to achieve my goal, to push me to become more uninhibited, or, I should say, to be more of an exhibitionist."

She'd once again have to wear her new outfit to a tourist spot, but this time without a bra! That was, she realized, partially her fault. Will had twice mentioned that he was concerned about her regressing, and that he was concerned she had not make the progress he'd hoped for, and he obviously meant this to put her back on track.

She noted that the challenge permitted her to use the same park, but Will preferred that she use a different tourist spot. She smiled as she thought, "He undoubtedly intends to remove as much comfort and familiarity from each challenge as possible."

Again, Will allowed her to have either a friend or a stranger take photos of her, although Will noted that he preferred that she have someone she knew take the photographs. "Of course," she said aloud, "He's obviously disappointed that I regressed and wore a bra. He wants this to be a real challenge, he wants to push me, to make me face my inhibitions and overcome them."

After reading the challenge again to be sure, she knew what Will expected; Denise made a cup of tea and sat in her large easy chair to contemplate her concerns. First, should she take this challenge, second, which tourist spot should she use if she did take the challenge, third, should she have a friend go along to take the photographs or again ask a stranger, and fourth, if she asked a friend, who should she ask?

* * * *

An hour and a second cup of tea later she had made all her decisions. She wanted to take this challenge because, as her mother had asked her, "How else will you prove to him and yourself that you are not a prude?"

For her next three questions, she first picked the Villa Ronai as the tourist spot where she would pose for her photographic proof, because, since it had been purchased and remodeled by the head of a modeling agency, it had often been the location used for many model photo shoots and if she was going to have photographs taken of her with her breasts practically exposed she at least wanted it to be in a beautiful setting.

Next, she decided that it would make sense to have somebody she knew take the photographs, because she could never be sure if anybody at the tourist spot would be available or willing and, of more concern, if they would be trustworthy.

As it turned out, the first three questions where the easiest to resolve, deciding which of her limited number of friends she was willing to allow to see her dressed in such revealing clothing, especially since she was sure that Will's challenges would soon require her to reveal far more of her body. As she thought about each friend, she concluded that she didn't trust most of them to keep a secret and even suspected that a few might secretly use their cell phones to take photos of her in her revealing clothes and would have little compunction about sharing the photos with everyone they knew, even posting them on the Internet.

Eventually, she decided she'd ask an old friend she'd known since high school to be her photographer. Andrew and she became close friends while they attended the Arts School together. As it turned out, he was her only real friend while she was there and based on their friendship she believed she could trust him to keep her escapades a secret. After all, Andrew had kept the fact that he was homosexual a secret. Only a handful of Andrew's closest friends knew he was gay, and fewer were aware that his best friend, Jackson, was also his lover.

Andrew was polite, good looking, and a good dancer. She went to parties with him whenever Jackson was working out of town. When they were at a club together, she always danced with Andrew. She like him, not just because he was cute and a good dancer, but because she felt safe with him and because neither he nor Jackson teased her for being too big or too fat and they never made lewd advances toward her like many of the other guys. In addition, she knew Andrew was a good photographer. While they attended Arts School, several fashion design students asked Andrew to do photography work for them, including Denise's former roommate.

* * * *

After thinking about it for a half hour, Denise decided she would ask Andrew to be her photographer and, if he agreed, she would take the challenge.

She called Andrew and explained that she would like him to be her photographer as she completed one of a series of dares from another friend. He did not ask any questions and quickly agreed. He did request that in return she would agree that right after their "photo shoot" they would go to his favorite bar for a couple of rounds of drinks and perhaps a couple of dances. Denise agreed only because she knew that if she didn't like the looks of the bar she would just refuse go inside. She was sure that Andrew was too good a friend to object, he would understand her reluctance, and he would accept her decision.

She asked, "Will tomorrow be alright?"

"It will be fine. It will give me an opportunity to try out my new Nikon camera."

Denise remembered that she wanted to maintain control of the photographs and asked, "Will your Nikon take a standard two gigabyte memory card?"

"Yes, of course."

"I will bring my own memory card. You will use only this card. I expect you to return it to me immediately after the photo shoot. Is that acceptable?"


The next day was Thursday and she worked a half-day shift in the morning. When Andrew told her that he only had morning classes, Denise told him, "I will pick you up outside your apartment house around one-thirty tomorrow and drive us to the Villa Ronai for our photo session."

Denise emailed Will her acceptance, simply stating, "I have read your third challenge and I accept it. I will do my utmost to meet all of its specified conditions." She signed it, "Your Challenged Friend, Denise."

The rest of the evening she had to keep convincing herself to go through with the third challenge, to go to Villa Ronai with Andrew for her "sans bra photo shoot" wearing a nearly transparent blouse -- a fact she confirmed when she reviewed the photos from her second challenge.

* * * *

Villa Ronai Jaunt

When Denise awoke on Thursday morning, she had the memory of yet another dream fresh on her mind. In this dream, she was at her favorite nightclub wearing her challenge outfit, as she and now even her mother referred to it. While she danced, she unbuttoned, stripped off, and tossed her diaphanous blouse into the crowd. After going around the dance floor, she untied her short wrap-around skirt, let it drop onto the floor, and kicked it into the crowd. She continued dancing wearing only her new heels. As with her previous dreams, she was completely uninhibited and happily accepted the praises and compliments about her beautiful body and uninhibited behavior.

Throughout her workday her mind wandered back to her upcoming third challenge, "Did she have enough willpower to go to Villa Ronai with Andrew and let him photograph her 'sans bra' while she wore an all but see-through blouse? Could she continue to pose, her breasts virtually exposed, while people walked past her?"

When her workday ended at one o'clock, she grabbed her gym bag and headed to the ladies restroom in the office building to change. After removing the challenge clothes from the bag, Denise removed her jeans, stuffed them into her bag, and put on the short tan, suede, wrap-around, tie-waist skirt. She took off her loafers and dropped them in the bag before she rolled a stay-up hose up each leg and then stepped into her stiletto-heeled sandals. She next pulled her lightweight hooded sweatshirt up over her head and dropped it into her gym bag. Now came the moment of truth. After taking a deep breath and confirming her commitment, she removed her bra. Her breasts swayed freely as she bent over and dropped the bra into the gym bag. In bathroom mirror she saw the reflected image of her big, unconstrained breasts shaking and bouncing, as she slipped on her tan front-buttoning mesh top blouse and tucked it under the waistband of her skirt. Again, she saw that in the sunlight, the sheer material of the blouse revealed everything from her waist upwards.

Reciting her mother's oft stated request of her, "Loosen up and enjoy the bounty God and my good genes have given you," and following an old piece of advice from her mother, Denise grabbed her gym bag, held her head up, stood straight and tall, and walked to her car with a purpose, ignoring that her breasts jiggled and bounced with each step she took in her three and half-inch stiletto-heeled sandals.

Traffic was unnaturally light and Andrew was waiting near a bus stop when she arrived. Other than the unnerving feeling of having a purported gay man stare at her barely concealed breasts, the drive to the Villa Ronai was uneventful.

The Villa Ronai on Old Stony Hill Road was a restored 1940s villa. Denise had chosen the villa because of its views of the Caribbean Sea, the surrounding hills, and the city of Kingston. It had nine acres of well-tended sculptured gardens, stone terraces, fountains, and sculptures. Additionally, she liked that the villa had often been the site for model photo shoots and beauty contests.

When she arrived at the villa, it was obvious that she would have to walk more than a hundred yards from the parking lot to get to any location that would identify the villa and its public park. Andrew, without apparent concern for her predicament, identified a location he wanted to use, but it was further away. Denise initially thought to argue with Andrew, but decided that while she would have to walk further to his selected location, she would also be further from the crowds roaming between the villa's main building and the parking lot.

Repeatedly thinking of her mother's admonition that she, "Loosen up, quit acting like a prude," Denise followed her mother's oft repeated advice, and pulled her shoulders back, sucked in her stomach, thrust out her chest, walked carefully in her stiletto heels, and tried to stay beside Andrew as he led them to the location he'd chosen.

At a small hill on the seaward side of the villa, Andrew found a patio, with concrete benches and railing, perched between a clump of twenty-foot tall cypress trees and on the edge of a thirty-foot cliff overlooking Kingston. Once they arrived, Andrew walked around considering the view and direction of the sun before he posed Denise. His choice of the location where he wanted her to pose was a concrete patio just behind the concrete railing with the cypress trees on both sides.

"Stand erect and look up toward the Villa," Andrew instructed as he moved to one side so the sun outlined her breasts through the thin material of her blouse. He took several photographs from various angles.

Andrew then turned her so the outlines of her erect nipples were visible under her blouse before instructing her, "Spread your feet apart. Now, stand erect, lift your shoulders, pull them as far back as is comfortable, and lower them. Good! Gently suck in your stomach until you feel strain in your abdominal muscles. Excellent! Look at me as if I'm your lover and you want me to make love to you right here and right now! Perfect, now smile and don't move!"

Andrew again took a half-dozen series of photographs from several different angles.

"Fantastic! You can relax now," Andrew told her with a big smile.

"Thank you, but to win this challenge I will need photographs proving I'm at the Villa Ronai," Denise complained.

* * * *

For their next photo shoot location, Denise led them back up the hill to a spot where she could pose in front of the villa's main building while standing next to a sign that identified it as the Villa Ronai. As they walked, Andrew asked, "Would you like to review the photos I just took?"

After a short pause, Denise concluded and explained, "It was difficult enough to convince myself to come up here and pose for those photos. Right now, I feel like I'm dressed and therefore covered. I don't think I want to confirm my belief that when I'm wearing this blouse in this bright sunlight my breasts are fully exposed."

When they arrived at the spot she'd selected, Denise noticed that while it was a perfect place to prove she was indeed at a tourist spot, the location was just off the main pathway between the public parking lot and the location where the tours of the villa began. Yet, despite knowing her breasts would be clearly discernible to anyone who looked as they passed by, she decided to go ahead and let Andrew pose her as he took the photographs she needed to prove she'd accomplished this challenge.

Once he placed her at a spot that allowed him to frame her with the villa and the identifying sign Andrew positioned Denise so the bright sunlight increased the transparency of her blouse. Andrew again posed her to accentuate her shapely legs, curvaceous body, large breasts, and erect nipples.

"Okay, remember the last pose, stand erect with your feet apart, and head up. Good! Now, as you did earlier, look at your lover so he knows you need him so desperately that you're ready to have your lover go down on you right here! Show him that you desperately want him to fuck you right now! Oh, yes! That's fantastic!"

Andrew moved from one side to the other taking dozens of photographs as she posed.

* * * *

Tourist's Photo Request

Just as Andrew announced he was finished, Denise noticed a gentleman nervously approaching. He was obviously an American on tour -- he wore a blue baseball cap with "Dam Ships" embroidered in gold on the front, a light-blue nylon Columbia short-sleeved fishing shirt, carried a white canvas bag with "Holland America" printed in blue, and had a sticker on his chest with the Holland America logo and a number identifying him as a member of the cruise ship's tour number 7.

He smiled broadly as he stopped and asked her, "Pardon me miss, but aren't you one of the Jamaican Carnival dancers on my grandson's poster?"

Not knowing what he meant, Denise looked questioningly at the gentleman before answering, "I've danced in the Road March, but --"

"My grandson has a huge poster of you and another beautiful young lady on a Carnival float wearing headdresses, smiles, and apparently nothing else."

"I've danced on a Carnival float, but --" Denise muttered, remembering the time she'd accepted a dare from fellow float dancers and was topless as they rolled into Road March Reviewing Area at the end of the parade -- a vacant field off Oxford Road with an oval track around it and temporary grand stands surrounding the field.

"Can I have a picture with you? My grandson will never believe I met you unless I have a picture," the gentleman stammered as he pulled a camera from his Holland America bag.

"Are you sure you don't have me confused with Dani Sperle from Rio?"

"My grandson has a poster of her walking in the Carnival parade wearing only a headdress, sandals, and a tiny, glued-on, triangle as a G-string. No, I'm pretty sure you're one of the two topless dancers in his Jamaican Carnival poster," the American explained as he openly ogled her breasts which were barely concealed as they jiggled under the sheer, tan, mesh of her blouse.

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