Jamaican Beauties Jaunt Ch. 06

Without thinking, Annika asked with honest curiosity, "Why bother with swimsuits at all?"

"Actually mother, you may have a point. I'm concerned that buying clothes might be a waste of my time and money. In fact, Will has mentioned that if I'm willing to try it he would change his reservations so we can stay at a resort where I wouldn't need to wear any clothes," Denise confessed.

"Do you think you would be able to go naked in public?"

"You know mother, since Lars cheated on me and then dumped me, I've been trying to take your advice to heart, to quit acting like a prude, to start enjoying what I have. Will is always telling me that I'd be much happier if I'd stop being so inhibited. I now realize that I was happiest during the progressive challenges. So I'm really trying to change."

"And do you think that you've become uninhibited enough to go to a clothing optional beach or resort and spend a week naked, with a man you've just met?"

"I'm not positive. But I'm hoping that you will help me to continue to overcome my inhibitions so I can put an end to Will's teasing," Denise begged, and then continued, "I need to get some more clothes for the Jaunt and now for Will's Hedonistic Pursuits. I want to get some things that will make Will stammer and admit that I'm not a prude."

"Then why don't we go shopping tomorrow afternoon?"

Denise smiled and nodded her agreement to her mother's offer and added, "You have to admit that I'm much less inhibited now, than I was before I met Will."

Slipping into her psychologist role, Annika asked, "What do you think was the primary factor that led to your recent change in attitude?"

"The positive factors have been father, you, and my experiences during the Seven Progressive Challenges. Although I had a major setback or breakdown during the challenges, I've learnt from that experience and I think I've matured."

"Nevertheless, how are you going to maintain that attitude the next time you're faced with adversity, like when your former Arts School roommate and her friends ridicule you," her mother inquired.

"Well, there's one other thing, it is my desire to always be a winner. I enjoyed my experiences whilst I was doing Will's progressive challenges; I adored the feeling of accomplishing them. I was thrilled as I wrote about them and excited when Will congratulated me for my accomplishments. I don't ever again want to live my life without those feelings. It is my resolution that this year I will be a winner. To do that, I know I'm going to have to take every challenge presented me and accomplish it, fully and completely. That's what I was doing with the progressive challenges and that's what I hope to do for the rest of my life."

Annika was pleased with Denise's new attitude. She only worried about one statement Denise made, her comment that she was, "excited when Will congratulated [her] for [her] accomplishments." That was an ominous statement. It meant that Denise placed a great deal of value in Will's opinion. Annika, noted that she would have to monitor that situation, to make sure it didn't go too far, to make sure Denise didn't "fall in love," with her Internet friend.

* * * * *

When they returned to the house, after having lunch and several glasses of wine at the Frigate, Annika reminded Denise about her shipment of clothes and suggested she should try on each of the new clothing items. She also requested, actually dared, that since it was such a nice day, Denise should model the new clothes in the backyard and allow Annika to take photographs so they could see how the clothes looked and fit on her.

Denise had few options other than to accept her mother's offer, after all, she'd just told her that from this day forward she was going to accept and accomplish every challenge presented to her.

As Denise modeled each new piece, her mother had her go into the backyard and pose for her as she took photographs, "To show your father how good you look in your new clothes and how well you're doing with your workout program and new attitude."

Denise first tried on the black tank swimsuit. Its low cut front revealed the top of her breasts and a bit of cleavage, the high cut sides exposed her hips and, because it was a thong, it revealed all of her buttocks. As she modeled it for her mother, Denise remembered that she'd selected it because she knew Will would appreciate it. It was, after all, a black, thong version of the Bay Watch television show swimsuits.

As she posed for her mother, Denise automatically followed Andrew's advice when she was modeling for the progressive challenges photo shoots, and posed with her legs apart about shoulder width, standing erect, stomach sucked in, shoulders back, breasts thrust forward, head up, eyes focused on the camera or another object, and a huge smile on her lips.

Denise next modeled the white gauze peasant blouse with three-quarter length sleeves, a diamond cut back, and ruffled trim on the sleeve opening and the front closure. Although it was gauze, the blouse would have been even more revealing if not for the tie strings at the bust in front that held it closed.

As she walked around the backyard, her navel and hips were visible and depending on her motion or the breeze, her cleavage and the bottoms of her breasts were often exposed. Denise joked to her mother, "I know it's a little revealing, but not nearly as much as the blouse I wore for the Challenges, especially when it was unbuttoned."

"In that case Denise, why don't you untie the strings on that blouse and let's take a few more photographs so we can see how exposed you'll be?"

Denise surprised herself, when, without hesitation or consideration, she untied the single set of strings and repeated all her earlier poses as her mother took photographs. As she did, she enjoyed the same feelings of joy and freedom she'd experienced when she was completing each task for the Seven Progressive Challenges. She felt uninhibited and extremely happy.

The last piece of clothing she modeled was the black halter dress with straps that tied at the back of her neck, a deep V-neck front, and a low open back. She'd selected it just for Will. She was sure that he'd like the dress and she was confident that she could wear it in public, especially if he asked her. As Denise modeled the dress, she pretended it was Will and not her mother that was taking the photographs. When she completed her mother's directed poses, Denise explained that the dress could also be worn as a keyhole as she untied and retied the neck to show her mother.

Once Annika had taken photographs with the keyhole design look, Denise retied the dress as a halter, but she let it slip lower on her body, exposing more of her cleavage and breasts, and tied the straps loosely with a single loop. As she walked about the backyard and posed for her mother, the deep V-neck opening in the front of the dress was nearly low enough to expose her navel and the dress straps barely covered her breasts. In fact, her breasts swayed with each movement and as the breeze blew aside the top of the dress, they were often exposed.

Denise grinned and asked, "This is how I thought Will would want me to wear this dress. What do you think?"

Annika smiled at her daughter's new found freedom and audacity before she told her, "First, you look great in that dress. Second, I think Will is going to like you in anything you wear. Third, if you wear that dress like that, Will is not only going to love it, he will likely want to take you back to your room and fuck you repeatedly."

Later while they reviewed the photographs, Denise commented to her mother that she thought she looked good enough to be a model for one the ladies clothing websites on the Internet. She was now sure she would be comfortable wearing the swimsuit and clothes while at Will's resorts.

Annika smiled and asked her if she had considered entering photographs to the websites' customer competition, to see if other people agreed with her assessment of how good she looked wearing the outfits she'd purchased.

Denise thought for a moment before she explained, "I first want to find out if I looked good enough to have a chance in the competitions. I might ask Will to take photos of me in these clothes when we're on the Jaunt or at his resorts. If he's pleased with the photographs, I'll send them in to the customer contest to find out how well I do against all those other great looking customers."

* * * * *

Challenge Lessons

Saturday morning, while Denise was at the gym, Annika selected eight of the photos of Denise modeling three of her new and quite revealing clothing items she'd taken the day before. With the expectation it would generate a positive response and thus reinforce Denise's improving self-image, she submitted them to the customer photos contest of the clothing website where Denise had purchased them. When the clothing items arrived, Annika had visited the website and noted the customer contest. Reviewing the photos of the current contestants and the winners from the last several months, Annika had been positive that Denise would easily win the contest if she entered.

That afternoon, after Denise returned from her workout, Annika prepared a light lunch for the two of them, which they enjoyed along with several glasses of wine. Annika took that opportunity to have a long talk with her daughter about the dangers of sex and a longer discussion of the pleasures of sexual activities. Denise was surprised to realize that it was only the second time in her life she'd thought of her father having engaged in a sexual act. The first was on Christmas Eve when she witnessed a practically naked, yet obviously unconcerned Max behave in a deferential behavior toward Denise's father and even kissed him, rather sensually, on the lips.

After refilling their wine glasses, Annika asked Denise, "Dee-Dee, on a completely different subject, I understand that it might be difficult for you, but would you be willing to talk about your experiences, emotions, and lessons whilst you completed the first five of Will's Seven Progressive Challenges?"

Denise thought for a moment before answering, "Mother, I know you only want to help. However, it's over; I resigned from the Seven Progressive Challenges and I'm not sure if I'm ready to talk about it."

Annika frowned and asked, "Will you at least listen to a couple of my questions? If you do not wish to answer them I will understand."

"Okay, I'll listen and try to answer."

Wanting to ease into her real concern, Annika asked a preliminary question to get Denise to talk, "I remember that your last challenge had two levels and three tasks, and that you had to be photographed whilst fully exposed as you danced in a nightclub with a friend. But, so I might better understand what happened, would you give me an overview of the events of that evening?"

Denise thought for a moment and mentally prepared as concise and yet explanatory a description as she could, "That evening I skipped my workout and came straight home after work. I showered, trimmed and shaved my quim, and dressed in preparation for my photo shoot. I walked to the Quad and met up with Andrew and Jackson."

"Sorry to interrupt, but I remember you saying that you had decided to dance with Andrew for the dare. Why did you invite Jackson along?"

"I wanted to dance with Andrew because I trusted him. Andrew suggested we use Jackson to take the photographs. He told me that Jackson was a good photographer and that I could trust him."

"That was a logical solution," Annika agreed.

Denise continued her synopsis, "I was still going for all or nothing, so for the first task I removed my skirt and blouse and posed naked in front of the Quad."

"Again, I'm sorry for interrupting, but are you saying you weren't wearing underwear when you walked to the Quad?"

"It seemed reasonable given I was going to expose my private bits anyway," Denise answered before she immediately continued her description of events, "Inside, we found a secluded place by the back bar in the Oxygen Room, and I again exposed myself at the bar whilst Jackson took photos as my proof for the second task. Jackson then asked an American woman tourist to take pictures of the three of us. Afterward, as Jackson was taking a couple of pictures of the American woman and me, we kissed, she fondled my breasts, and one thing lead to another, and she gave me oral sex—"

Annika interrupted, "Denise, I'm sorry to interrupt once again, but I just want you to know that if you ever wish to talk about your experience with the woman, I'd be willing to listen to you and offer you any help, advice, or counseling you may want or need."

"Thanks mother, but I'm quite okay with that experience, it was very... pleasant and enjoyable," Denise explained with a faraway look in her eyes and a smile on her lips.

"Good. But remember, I'm not just a psychologist, I personally understand what you experienced, and I'm sure I can offer you some insights to your feelings," Annika noted.

"Thank you, I'll keep that in mind," Denise acknowledged, and without fully understanding what her mother had shared with her, she continued, "The American and I danced and talked, and after she left, I decided to complete the last task. As Andrew and I were on the dance floor with Jackson taking photographs, my old Arts School roommate showed up."

Annika saw the sadness in her daughter's expression and again interrupted, "I think, based on past experience, I have a good notion of what happened, but, if it's not too difficult for you, please tell me specifically what transpired?"

Denise frowned, but without considering the ramifications of her honesty and forthrightness, answered, "I was dancing and dreaming that I was on a balcony and teasing Will, wanting him to know how much I needed to have sex with him. Then my former Arts School roommate and her cohorts criticized me. They reminded me that I was big and disproportionate and that I shouldn't be dancing naked at the Quad nightclub."

Annika smiled as she reminded Denise, "I've told you before, they're jealous of you. They're compensating for their own shortcomings by ridiculing your good looks," then she asked, "But, what I'd like to know is how did you ever find the strength to finish the challenge?"

Reliving that moment and holding back her tears, Denise told her mother, "To this day, I don't know how, but I forced myself to finish the dance. I felt shame for exposing my big, ugly body and that's when I first thought about giving up the Seven Progressive Challenges. Yet, I also knew that no matter how I felt, I had to be sure I had enough photos to accomplish the fifth challenge. I pulled Andrew's arms around my waist and danced around the floor until I saw Jackson taking photographs and I began chanting aloud, "All or nothing."

Annika nodded and Denise continued, "At that moment I was committed to finishing the challenge I'd already started, so I asked Andrew to help me finish our dance and he did everything I asked of him without question. After we finished the dance, I dressed, left the club, and walked to my apartment where I submitted the proof that I'd completed all three tasks of the fifth challenge. Then I resigned."

Annika almost whispered, "You had accomplished five of the seven challenges. Why did you resign?"

Denise, tears now falling, whimpered, "I never again wanted to be reminded of how miserable those girls made me feel."

Knowing she had to get it out in the open, Annika asked what she suspected would be the hardest question, "How did you feel when you resigned from the challenges and afterwards?"

Denise caught up in giving her mother honest answers, confessed, "When I resigned I was miserable and angry. I felt ugly and unloved. Yet, to my surprise, much of my new behavior didn't change. I still slept and hung around my apartment naked. I still wore short skirts, high heels, and undid the top three buttons of my blouses while at work. I continued to dream every night about wanting to have sex with Will. I still masturbated in my sleep every night, and most days—even as I read, wrote, or just dreamt."

Annika had a thousand questions, but wanting Denise to know she was free to work through her problems as she saw fit, told her, "Again, if you want to talk, about anything, you know I'm always willing to listen, and I promise I will give you advice only if you ask for it."

"Thank you mother, I appreciate your offer and I will keep it in mind. However, for now, it still hurts too much to think about. I just want to move on with my life. When I'm ready to talk about it, I will— with you and Will."

* * * * *

Wardrobe Renewal

Later that afternoon Annika announced, "Okay Denise, I think it's time we changed and went shopping for some new clothes."

"Why do we need to change?"

Annika smiled, "First, if we are going into town, we need to wear something nice. Additionally, because we'll be trying on clothes, what we wear should be easy to take off."

"I didn't pack very much. You've seen what I brought, what should I wear?"

"Why not wear your new peasant blouse? I could let you have one of my wrap skirts to go with it."

"I can't wear that in the afternoon, especially into New Kingston."

"What happened to your new years' resolution?" Annika teased, and before Denise could answer, offered, "I'll make you a deal. If you'll promise you'll wear my new duster dress in the proper manner, I'd like to try out your peasant top."

Trapped, Denise had little choice, and agreed.

Annika changed first, and returned wearing the white sheer jersey peasant blouse with the front closure closed with a loosely tied bowknot, along with a black, pleated, hip-hugger mini-skirt, and white sandals with three-inch heels.

After modeling the outfit, by turning around once, she announced, "I laid the duster on your bed. I want to remind you that you promised to wear it in the proper manner. Therefore, what I've laid out on your bed is everything you will need. That is what you will wear if you intend to keep your New Years' resolution and your promise to me."

Denise frowned, but her only response was, "Yes ma'am," as she walked into the spare bedroom to change.

Lying on the bed was a white linen front-buttoning duster dress with rose bandana short puff sleeves, a two-inch wide rose bandana around the hem—which fell four inches above the knees—and a two-inch wide waist tie-string around the waist—actually, it was just below the bust and was the only means of closing the front of the dress. Next to the dress was a small package with a note.

Denise read the note, "Your father was afraid that I would push you further than you could handle. He bought these for you and allowed me to decide when and if you needed them. They are somewhat modest because your father believes you probably have not yet shaved your pubic hair."

At the bottom of the note was a quickly scribbled addition, "I think the white would go best with your dress. Keep in mind that you may have to remove them in order to correctly and properly wear some of the clothing items you said you were interested in buying and wearing. Love Always, Mother."

Denise opened the package and found three, lace "boy shorts." Except for color, they were identical with V-cut waistbands and bottoms cut to reveal her lower buttocks. They were white, black, and pink. Denise smiled and tried to decide if she was angry, embarrassed, or pleased.

The anger was because her mother and father were talking about her and conspiring to push her to become uninhibited. She let go of that feeling, concluding that her parents weren't interfering with her life. Instead, they were assisting her in her effort to achieve her goals, her resolutions.