tagNovels and NovellasJamaican Beauties Jaunt Ch. 03

Jamaican Beauties Jaunt Ch. 03


Chapter 3 -- Villa Ronai: Her challenge is to pose and dance while braless.

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 continues the story of a young Jamaican woman's acceptance of the Seven Progressive Challenges and her accomplishment of the third challenge: to pose braless in a public tourist spot. While completing the challenge she also poses topless with an elderly American tourist and her Jamaican male photographer.

Interracial Love: this chapter continues the 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 your comments to the author. It is the author's desire 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.

* * * * *

Third Challenge

Monday evening after a long day at work and a hard workout at the gym, Denise was enjoying a glass of wine and checking her emails when she received the third of the seven progressive challenges. Seeing the email's subject was "Third Challenge: Tourist Spot (sans bra)," she hesitated. Although she'd spent the week remembering and relishing her excitement while completing the second challenge, the realization that she would have to go out in public without a bra while wearing the sheer tan blouse concerned her.

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

To steel herself, Denise recited a variation of her mother's question to her when she was considering taking the challenge, "Why take the challenge if you're not willing do whatever you must to win it?"

Emboldened by her mother's intended inspiration and her exciting memories from and subsequent erotic dreams about the previous challenge, Denise's trembling finger pressed the key to open the email and display the message's contents—the third challenge. She was surprised to find her concerns overridden by her excitement and anticipation.


From: Will Kruger

To: Denise Johnson

Date: Monday November 1

Subject: Third Challenge: Tourist Spot (sans bra)


As I mentioned when I acknowledged your accomplishment of the second challenge, I 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 continually progress towards your ultimate goal, (in this case to become uninhibited,) while learning to recognize when you are regressing, to take the steps necessary to overcome any obstacle to your progress, and to learn to prevent the obstacle from interfering with your progress in the future.

For the third challenge you will again need to wear the clothes I approved for your first challenge with the top three buttons of the blouse unbuttoned, your blouse tucked into your skirt and pulled tightly over your breasts, and WITHOUT a bra, camisole, or any similar form of covering or undergarment.

For this challenge, you will again go to a well-known tourist spot of your choosing, preferably a different location than the one you used for your second challenge. While at the location, you are to have a stranger or preferably, someone you know, take at least five photographs, preferably many more, of you posing at that tourist spot while dressed as described in the previous paragraph.

As in the previous challenge, your proof will be at least five photographs showing that you are wearing the clothes, obviously without a bra or similar undergarment, while at an identifiable tourist spot. As with the first two challenges, I expect you to provide a summary of your journal entries regarding your feelings as you prepared for, performed, and completed the challenge.

In light of your regression in the second challenge, I asked the Société Internationale de Défis 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, within the established timeframe, you have not provided acceptable proof that you accomplished the challenge, the society will disqualify you and deem you to have failed the challenge.

Your Disappointed, yet Optimistic, Challenger,



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

As she reread the challenge to ensure she knew exactly what Will expected, Denise concluded that the requirement that she wear her blouse tucked into her skirt to prove she was braless and the time limit to complete the challenge were of her own doing. Will had twice mentioned that he was concerned about her regressing, that he was concerned she had not made the progress he'd hoped for, and he obviously meant for this challenge to put her back on track.

Seeing the challenge permitted her to use the same park, but Will preferred that she use a different tourist location, Denise 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 he preferred that she use someone she knew. "Of course," she said aloud, "he's disappointed that I regressed and wore a bra and he wants this to be a real challenge. He wants to push me, to make me face my inhibitions and overcome them."

Denise moved to her large easy chair to contemplate her concerns. First, should she accept this challenge, second, if she did take the challenge, which tourist spot should she use, 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?

A half-hour and a glass of wine later she'd made all her decisions. First, she wanted to accept this challenge because, as her mother had said, how else would she prove to Will and herself that she wasn't a prude.

For her second question, she selected the Villa Ronai as the tourist spot where she would pose for her photographic proof. Since it was remodeled and landscaped, it was frequently the location of beauty contests and model photo shoots. She'd decided that 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 made sense to have somebody she knew take the photographs, because she could never be sure if anybody at the tourist spot would be available, willing, or, of more concern, trustworthy.

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

Eventually, Denise decided she'd ask an old friend to be her photographer. Andrew and Denise first met in secondary school and became good friends while they attended the Arts School. As it turned out, he was her only real friend while she was there and based on that 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 and roommate, Jackson, was his lover.

Besides being trustworthy, Andrew was polite, nice looking, and a good dancer. Whenever they were at the same club she made it a point to hang out with Andrew; she always danced with him and frequently with Jackson. Denise often went clubbing or to parties with Andrew when Jackson was working, out of town, or otherwise unavailable. She liked Andrew, 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 about being awkward or buxom. Moreover, they never made lewd advances toward her like many of the other guys at the clubs. Just as important, she knew Andrew was a good photographer. He worked part-time as a photographer's assistant and as an assistant instructor at the Arts School. Many fashion design students requested Andrew to do fashion photography work for them.

Denise concluded she would ask Andrew to be her photographer and, if he agreed, she would accept the challenge. With all her decisions made, she called Andrew and explained that she wanted him to be her photographer while she completed one of a series of dares from her Internet friend. He did not ask any questions, he simply stated, "I've been looking for an opportunity to try out my new Nikon camera. I'll be happy to do it for you"

She asked Andrew, "Would you be able to do the photo shoot Thursday afternoon?" It was her next free day, when she worked a half-day morning shift.

"I only have one morning class on Thursdays, so that would be great for me."

Andrew's only request was that after their "photo shoot," she go with him to his favorite bar for a couple of drinks and perhaps a few dances. Denise readily agreed, knowing that if she didn't like the looks of the bar she could just refuse to go inside with him. She was sure Andrew was too good a friend to object, he would understand her reluctance and accept her decision.

Denise, remembering she wanted to maintain control of the photographs, inquired, "Will your Nikon take a standard two gigabyte memory card?"

"Yes, of course."

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

"Sure," Andrew answered but wondered why she was concerned about the photographs she wanted him to take.

"Good," Denise told him and added, "I'll pick you up outside your apartment house around one-thirty Thursday and drive us to the Villa Ronai for our photo session."

"I'll be ready," Andrew agreed.

Denise emailed Will her acceptance of his third challenge, 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."

During the next two days, she repeatedly convinced herself that she was correct to accept the third challenge and she should go through with it. She told herself that the excitement and satisfaction of accomplishing the challenge would more than compensate for the concerns and fears she faced leading up to it. She repeatedly told herself that she wanted, no, she needed to go to Villa Ronai with Andrew for her "sans bra photo shoot" wearing a nearly transparent blouse—a fact she had confirmed when she reviewed the photos from her second challenge.

* * * * *

Villa Ronai Jaunt

When Denise awoke Thursday morning, she had the memory of yet another dream fresh on her mind. She'd dreamed she was dancing in her favorite nightclub wearing her challenge outfit, as she and her mother now referred to the skirt, blouse, and heels she'd purchased for her first challenge. As she danced, she unbuttoned, stripped off, and tossed her gossamer blouse into the crowd. Topless, she did a Calypso around the dance floor. She next untied her short wrap-around skirt, let it drop onto the floor, and kicked it into the crowd. Wearing only her heels, she again did a Calypso around the dance floor. As with her previous dreams, she was uninhibited and happily accepted the praises and compliments about her beautiful body and her impulsive, guileless, and sensual behavior.

Throughout the morning, her thoughts wandered to her upcoming third challenge that afternoon, "Did she have enough willpower to go to Villa Ronai with Andrew and let him photograph her wearing a sheer blouse whilst "sans bra?" Would she have the will-power to continue to pose with her knockers effectively exposed as people walked past her?"

When her workday ended at one o'clock, she grabbed her duffle bag and headed to the ladies restroom to change. After retrieving her "challenge outfit" from the bag, Denise took off her loafers and jeans, stuffed them into her bag, and pulled on the short tan, suede, wrap-around, tie-waist skirt. She then rolled a hose up each leg and stepped into her stiletto-heeled sandals. Next, she pulled her lightweight hooded sweatshirt over her head and dropped it into the duffle bag.

Her decisive moment had arrived. Taking a deep breath and reconfirming her commitment, she removed her bra. Her breasts swayed freely as she bent at her waist and dropped the bra into the bag. In the restroom mirror, Denise could see her unconstrained breasts swaying and bouncing as she slipped on her blouse, buttoned the front, leaving the top three buttons undone, and tucked the hem under the waistband of her skirt. She noticed that in the sunlight, the thin, nearly mesh material of the blouse revealed everything from her waist upwards.

Denise picked up her duffle bag and following an old bit of advice from her mother, held her head up, stood straight, and walked to her car with a purpose, ignoring that her breasts jiggled and bounced with each step she took in her stiletto-heeled sandals.

Traffic was unnaturally light and Andrew, as he'd promised, was waiting near a bus stop when she arrived. Other than the unnerving feeling of having a purported gay man stare at her all but unconcealed 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 beautiful landscape and marvelous views of the Caribbean Sea, the surrounding hills, and the city of Kingston. It had nine acres of well-tended gardens, stone terraces, fountains, and sculptures that Andrew could use as backdrops in the photos he would be taking of her posing in her sheer blouse.

When she arrived at the villa, Denise was anxious seeing she'd have to walk a hundred yards from the parking lot to the nearest location that would identify the villa. Andrew, apparently unconcerned with Denise's predicament, pointed out the location he wanted to use, one that was even further away. Denise initially thought to argue with him, but decided that although she would have to walk further to his preferred location, it would be away from the crowds of tourists roaming between the villa's main building and the parking lot.

Thinking of her mother's admonition that she, "Loosen up, quit acting like a prude," Denise again followed her mother's advice, and with her shoulders back, stomach sucked in, and chest thrust out, she walked carefully in her stiletto heels while trying to stay beside Andrew.

On a small hill on the seaward side of the villa, Andrew found a patio, with concrete benches and a surrounding railing, perched between a clump of twenty-foot tall cypress trees on a grassy slope that ended at the edge of a cliff and overlooked Kingston.

Andrew walked around considering the view and direction of the sun before he posed Denise. The position he finally selected was on a small hill behind the concrete patio with cypress trees on both sides and the villa visible in the background.

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

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

Andrew again took dozens of photographs from several different angles.

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

"Thank you, but in order to win this challenge I will need photographs that prove I'm at a tourist spot. From here you can't tell if that's the Villa Ronai in the background," Denise complained.

Andrew apologized for his misunderstanding, his mistake, as 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.

Denise noticed that although the location she'd selected was a perfect place to prove she was at a tourist spot, it was also 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 discernible to anyone who looked as they walked past, she decided to let Andrew pose her and take the photographs she needed to prove she'd accomplished Will's third challenge.

Andrew asked, "Would you like to review the photos I took earlier?"

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

Andrew placed her where she would be in the frame along with the villa and the identifying sign visible in the background. He next positioned Denise so the bright sunlight increased the transparency of her blouse. He had her pose to accentuate her shapely legs, curvaceous body, large breasts, and erect nipples. When he was satisfied with her position and pose, Andrew directed, "Okay, remember your earlier poses, stand erect with your feet apart, and head up. Good! Now, as you did earlier, look at your lover so he knows you desperately need him, so much so that you're ready to let him go down on you right here! Show him you're ready to have him "jook" you right now! Oh, yes! That's fantastic!"

Andrew moved from one side to the other taking dozens of photographs of Denise who was blushing as she followed his direction and tried to look as if she wanted her lover to "jook" her, to fuck her.

* * * * *

Tourist's Request

Just as Andrew announced he was finished, Denise noticed a visibly nervous gentleman approaching her. He was obviously an American tourist. 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 the cruise ship's logo and name printed in blue, and had a sticker on his chest with the cruise line's logo and a number identifying him as a member of "Tour 7".

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