Jamaican Beauties Jaunt Ch. 02

"Although the society's purpose is to offer challenges that are increasingly more difficult, daring, and risqué than their predecessor, the society reviews all challenges to ensure they are safe. The society will not ask, expect, or have any participant do anything dangerous. Nothing you do during the challenges should cause you any physical, mental, or emotional harm or get you arrested. Further, you can resign from, that is quit, the challenges at any time without having to specify your reason."

"I need to think about it," Denise responded after she'd read his messages.

Will immediately responded with three additional messages he'd prepared in the hopes they might keep her focused on the dare he'd placed before her and perhaps convince her to accept the challenges. It was Will's hope, that he could entice into considering them and because she'd willingly accepted her father's dares, she'd be inclined to accept his.

The first message, after Will quickly revised it, read, "I am taking your response, i.e., "to think about it," as your agreement to consider accepting the Seven Progressive Challenges. Assuming your interest is piqued and you will see the positive aspects of the challenges, I will send you an email with the subject: "Seven Progressive Challenges Offer." That email is a formal offer, approved by the society, which you can accept or reject. You may take as long as you need to decide whether you are interested in taking the challenges. Once you are prepared to make your decision, open the email containing the formal offer. You will have the option to reject, continue to consider, or to accept the challenges."

A subsequent message continued, "If you decide to reject the offer, use the email containing the offer to reply, stating you are "REJECTING the offer to participate in the Seven Progressive Challenges." If you wish to continue to consider your acceptance, you may do so, but only having opened the first message. Please do not open the second email unless you have decided to accept the Seven Progressive Challenges."

The final message stated, "With the formalities out of the way, let me make one last attempt to convince you to accept the challenges. I truly believe that should you accept them, you will find the Seven Progressive Challenges exciting, informative, insightful, and a great deal of fun. I hope, for your own reasons, you will accept the challenges and make every effort to complete all seven."

Will hoped the challenges would help her overcome her apparent repression and obvious inhibitions. That, through the challenges, she would learn to become uninhibited in her approach to dressing, life, and sex. It was his desire that the challenges would push her toward becoming a woman that enjoyed all that life had to offer.

Previously, Will sent a request to the Société Internationale de Défis Progressive explaining the reasons for presenting the challenges and his desired outcomes and goals, and received the society's approval to present Denise with her first challenge. Wishing to be in a position to move things forward, Will also developed a obtain approval for a preparatory challenge, one that would test her will power but not require her to expose herself too far outside her comfort zone. Since he had official approval, Will sent Denise the email explaining the first challenge.

* * * * *

Later that evening, after considering her options, Denise concluded she wanted to take Will's dare, to accept his Seven Progressive Challenges offer. She still wasn't confident that she could complete all seven of the progressively daring and risqué challenges that Will would undoubtedly present her. Despite her doubt, she opened the first email knowing she would consider and most likely accept Will's challenges.

_______________

From: Will Kruger

To: Denise Johnson

Date: Sunday October 10

Subject: Seven Progressive Challenges Offer

Denise,

You have agreed to consider the Seven Progressive Challenges and, should you accept them, to make every effort to complete each of the challenges presented to you. Remember, each challenge is progressively more daring and risqué than the previous until you either resign or successfully accomplish all seven challenges.

The first challenge is preparatory to several of the subsequent challenges. You should only accept the first challenge if you are willing and committed to completing the remaining six challenges and thus earning the Seven Progressive Challenges certificate from the Société Internationale de Défis Progressive, verifying that you have proven you are uninhibited and not a prude.

Please keep in mind that the things you will be challenged to do will not, in and of themselves, cause you any physical, mental, or emotional harm or result in your being arrested, although, they may cause you some difficulties if you are not careful. As you are completing the challenges, you always need to be aware of your surroundings and the people around you, especially those who can see you, and therefore take photographs and videos of you and what you are doing.

If you are still unsure of your commitment or ability to complete all seven of the challenges that I will present to you, please stop reading this message and send me a return email stating that you are REJECTING my Seven Progressive Challenges offer.

Read the next email message ONLY if you are committed to accepting and completing the Seven Progressive Challenges.

Your Hopeful Challenger,

Will

_______________

Although she'd read it, Denise didn't pay attention to Will's request or warning at the end of his first email. She only knew that she was interested in learning more about the challenges. She knew she wanted to prove to Will that she wasn't the prude he thought she was, that she could be uninhibited like her mother. Therefore, disregarding Will's conditions regarding continuing, she opened the second email.

_______________

From: Will Kruger

To: Denise Johnson

Date: Sunday October 10

Subject: Seven Progressive Challenges Offer -- Continued

Good!

First, if you wish to verify that the society officially sanctioned and approved these Seven Progressive Challenges, you may go to the society's website. Entering the International Society for Progressive Challenges in any Internet search engine should give you a link to their home page. Once there, you can enter my name and the challenge number (10-28295) in the website's search box.

I hope you will take the challenges in the spirit intended: as a means to allow you to test your will power, to push your exhibition boundaries beyond your current comfort zone, and to learn to enjoy the freedom of uninhibited behavior. Below are instructions you need to follow in order to accomplish your first challenge, which in turn will prepare you to complete the Seven Progressive Challenges.

Instructions for First Challenge

For the first challenge, and to prepare for the remaining challenges, you need to obtain 1) a short skirt with a hem at least four inches above your knees, preferably six inches; 2) a sleeveless, front-buttoning, lightweight, preferably transparent or at least diaphanous, blouse; 3) a pair of three-inch, preferably at least four inches, stiletto heeled pumps or sandals; and 4) optionally, but preferred, at least one pair of opaque, thigh-high, stay-up or hold-up nylons.

If you already have any or all of the items, you are well on your way to completing the first challenge. If, as I suspect, you do not own any of these items you need to purchase them at a clothing store.

When you have gathered the required clothing items, dress in the clothes and have someone, preferably someone you do not know, take at least five photos of you, somewhere other than your apartment, while you are wearing the clothes, and email three or more of those photos to me so that I can approve your selections and the accomplishment of your first challenge. An option to save you some money would be to have someone take photos as you try on and model the clothes at the store. That way, you won't need to purchase the clothing items until I have approved them. Once you have selected and I have approved the specified clothing items, let me know how much the clothes cost and I will reimburse your expenses.

To aid you in achieving your goal of completing the Seven Progressive Challenges and to practice documenting your proof of having accomplished each challenge, you need to prepare a journal. That journal should document 1) your preparation, (e.g., getting dressed and getting to the location); 2) executing the challenge, (i.e., the actions you took to accomplish the challenge); and 3) your feelings as you performed the challenge and just after completing it.

You will also need to take numerous photos throughout each challenge. Once you complete a progressive challenge, as your proof, in addition to a required minimum number of photographs, you will need to provide me a narrative of the events and your feelings along with any additional photos you believe are necessary or will add to your story and my understanding.

After you complete a challenge and I have accepted your proof, I will send you the next challenge. The challenges will continue until you accomplish the seven challenges or elect to resign and thus admit to the world that you are an inhibited prude.

It is my preference, but not a requirement of the challenges, that you email the photos of you modeling the clothes and specified descriptions within seven days of accepting the challenges.

Your Challenger,

Will

_______________

After sending the emails, Will picked up his wine glass, sat on his love seat, and wondered, "Will this push her too far or too fast? Am I asking her to do something she will find too uncomfortable to attempt? What if I'd misread or misunderstood what she has been telling me, or at least hinting? On the other hand and more importantly, what if I'm right in believing she subconsciously wants this, wants me to make her do this?"

He knew it was a risk, but, if he was right, if she had indeed been sending those signals that he believed he was receiving, and he had correctly interpreted and understood those signals, if, as he believed, she was unconsciously begging him to help her, it was his duty and his desire to do that, to help her.

To justify his actions to himself, he said aloud for the world to hear, "After all, she's my friend," and then said only to himself, "Friend? When did that happen?" He finally thought, "And is that what I want her to be, my friend, or am I hoping, wishing, praying for more than friendship?"

Will, wine glass in hand, leaned back in the love seat and considered all the things the two of them had shared in the last six months. He recalled and analyzed their chats to see if he could discern a pattern or a message. Later, as he got up to refill his glass, he reminded himself, that unlike computer systems, the patterns of human emotions were convoluted and difficult to discern and analyze, and talking aloud to himself he concluded, "This would normally be a difficult task, but given Denise's history and inhibitions, it will be nearly impossible to understand what signals she's sending. But, as her friend, I believe I owe her the effort."

* * * * *

Although she wanted to accept the challenges, Denise took most of the week to decide if she could and should go through with all seven challenges. On Friday at lunch with her mother, Denise mentioned the challenges in hopes of getting a fresh perspective, albeit one that would surely be excited about the idea of the challenges and pushing for her to accept every dare.

At first, they debated the benefits and problems with accepting the challenges. Annika pointed out, "I'm sure you'll find them to be thrilling and exciting."

Denise responded, "No, I'll probably find them unnerving and embarrassing."

Annika told her daughter, "It sounds like it would be very exciting," before giving Denise her usual motherly advice, "So why don't you loosen up, quit acting like a prude, and enjoy the bounty God and my good genes gave you!"

Denise expressed her reluctance to accept a series of challenges, "Mother, the challenges will undoubtedly involve escalating degrees of exhibitionism, designed, and intended to force me to expose ever more of myself unless I'm willing to concede that I'm indeed a prude."

The debate ended when Annika, after reading and considering Will's emailed assurance the challenges would be safe, insisted Denise take them and do everything asked of her. Annika asked her daughter, "Why would you even consider taking the challenges unless you're willing to do everything necessary to win them? Think all or nothing. How else will you prove to him and yourself that you are not inhibited, not a prude?"

After carefully considering her mother's arguments, Denise reluctantly acquiesced, "If you're sure it's the right thing to do, I'll take the challenges with the intent of completing all seven."

Now that she had committed to going through with the Seven Progressive Challenges, Denise reviewed the email and sat down with her journal—she had kept one since her first year in Secondary school when she decided she wanted to become a writer and had learned that maintaining a journal was a wonderful method for developing one's writing skills.

Denise began her Seven Progressive Challenges journal by listing what she understood about the challenges, what she believed she would need to do to accomplish the challenges, and what would be required of her. Knowing that the first challenge involved being photographed wearing revealing clothes, Denise expected subsequent challenges would involve someone taking photographs of her, in public, wearing those same revealing clothes, and less. Based on what she knew of Will from his emails and their Internet chats, she suspected the subsequent challenges would eventually include public displays of her most intimate body parts and possibly sexual activities.

Denise then remembered her mother's admonishment, that if she took the challenges—an action that her mother favored—she should do it as an "All or nothing," proposition. With that mantra rattling in her head, Denise believed she had everything she needed to take on the challenges, except her mother's uninhibited attitude towards her body, sex, and life in general.

For one of the few times in her life, Denise envied her mother. She wrote in her journal, "I believe I can force myself to accomplish any challenge that involves exposing my body, it's the exposure of my inner thoughts that concerns me. As for sexual encounters, I'm hoping, based on Will's previous statements that the challenges will not cause me any harm, and believe that because of his awareness of my concerns about sexually transmitted diseases and unwanted pregnancies, that I will not have to face that decision. Therefore, I've decided not to worry about continuing with the challenges until, and if, a challenge requires me to engage in a sexual activity. Only then will I consider and make a decision about quitting."

* * * * *

Sunday morning Denise woke up early, feeling excited and surprised to find that she was still willing to accept Will's Seven Progressive Challenges. She climbed out of her bed and, without dressing, prepared a cup of tea, sat at her computer, and prepared her email to Will.

_______________

From: Denise Johnson

To: Will Kruger

Date: Sunday October 17

Subject: Acceptance of the Seven Progressive Challenges

Will,

I am sure of my commitment to completing the first and any subsequent challenges you wish to propose. Thus, I hereby officially announce my willingness and intent to participate in the Seven Progressive Challenges. Within the week, I will send you an email, containing relevant excerpts from my journal and the specified photographs of me modeling the required clothing items. I hope that one email will be sufficient to permit you to review and approve the clothes I selected and thereby certify that I completed the first challenge.

Uninhibitedly, Denise

_______________

Afterwards, she sat back in her easy chair, enjoying her tea as she contemplated what challenges Will would present her and how she would go about accomplishing each one. She'd already decided she was willing to bare her body as necessary to win the challenge. "After all," she reassured herself, "I'm not giving anything away. I know, when I complete the challenges, I will still have all my body parts. Will promised no harm would come to me. He assured me I won't have to worry about being arrested or fired from my job because of anything he will asks me do in a challenge. Thus, once I've completed the seven challenges, I will still be me. As for exposing my inner thoughts, given the preparation for the challenges I don't see that being a problem. It appears, for now, that Will is simply pushing me to dress provocatively and flash strangers as a means of proving to him that I'm not a prude. Moreover, if I remember that I've already effectively done those things whilst dancing in Bacchanal Road Marches, the challenges shouldn't be difficult. I think, no I know, I can complete the seven challenges and prove to Will that I can be uninhibited."

Getting up to make one more cup of tea before she had to get dressed and go to the gym for her workout and swim, Denise almost shouted, "I will complete the Seven Progressive Challenges and he will have to admit that I am not a prude!"

* * * * *

First Challenge

Deciding to take advantage of her mother's obvious knowledge of revealing and risqué clothing, Denise asked Annika if she knew of any shops that sold clothes similar to those specified in Will's email. Annika, excited that Denise had accepted Will's challenges, gave her the addresses of three shops in the New Kingston area that sold the kind of clothing she suspected Will wanted Denise to wear—the kind of clothing Annika wore.

Friday morning, after her workout and swim, Denise grabbed her small digital camera and headed out to shop for her new revealing clothes. She'd decided to take Will's advice and to save some money by having a clerk or customer photograph her as she tried on and modeled the clothes in the store. That also appealed to her because she found it difficult to decide which of the few people she knew she trusted to photograph her as she posed in what would obviously be revealing clothes.

In the first store she visited, Denise found a short skirt she liked, but she couldn't find a transparent or diaphanous blouse or stiletto heeled sandals and if she was going to do the challenge, she was going to follow her mother's advice and "go all-the-way."

The second store had everything she needed, a short, hip-hugger, suede skirt with a hem that fell six inches above her knees, a sheer, tan, sleeveless, front-buttoning blouse, a pair of brown sandals with three and a half-inch stiletto heels, and tan, thigh-high, stay-up stockings.

Denise found a clerk—a mousey girl wearing a very conservative, grey skirt and jacket suit with a white blouse buttoned to her neck—and asked her if she would hold the clothes for her. When the clerk agreed to her request, Denise walked to the third store to see if it had any useful clothes. That store had some of the most revealing and risqué clothes she'd ever seen. She knew immediately it had to be her mother's favorite store. While she was sure Will would love any of the clothes in the store, she also knew she wasn't ready to go out in public wearing anything she found in the store. Besides, she believed most of the clothes were so revealing that should she ever have the nerve to wear them in public the police would likely arrest her for indecent exposure.