Jamaican Beauties Jaunt Ch. 07

Excited that Max was interested, Denise started with the first time she exposed herself to the sales clerk when she selected the clothes she would wear for the remaining challenges. She progressed through each challenge, only briefly explaining the specific challenge, since she'd shared that earlier at the Quad, instead, she focused on how she felt as she prepared for and accomplished each challenge and answered all of Max's subsequent questions. Denise continued sharing her experiences through her final challenge, when she had her first lesbian experience and danced naked at the Quad, before giving up the challenges.

Several glasses of wine and numerous questions later, the young ladies decided it was getting late, and Max was too intoxicated to drive, so they agreed to sleep together in Denise's double bed.

As they laid side by side, naked under a lightweight duvet, Max placed her hand on Denise's breast and asked, "Would you mind... would it bother you... if I fondled and suckled your aroused nipples?"

Denise mentally debated whether she should accept Max's request, "Would it make me a lesbian? What will Max think of me if I said no, or if I said yes? Is this a test? Did my mother put her up to this? If so why?"

Before Denise could decide, Max decided for her. She pulled Denise so they faced each other, leaned in, and gently suckled Denise's erect nipple.

As she had with Michelle, Denise focused on her pleasure and responded to the actions of Max's lips and tongue. She soon lifted her breast so her aroused nipple was easily accessible to Max's lips.

Max responded by sucking the nipple deeper into her mouth, holding it in place with her lips, and lapping it with her tongue. Denise's moans were music to Max's ears and she quickly kneeled over Denise. Max alternated suckling one nipple between her lips as she pinched the other between her thumb and index finger.

Denise responded in kind, caressing and fondling Max's large, heavy, hanging breasts and pinching her nipples just as Max was pinching Denise's erect nubs.

Assuming Denise would be open to enjoying their experience, Max took a calculated risk and crawled upwards and kissed Denise's lips. Denise immediately returned the kiss and Max rolled onto her side, pulling Denise onto her own side and closer, chest to chest, as she French kissed her receptive and responsive friend.

As they continued to kiss, as their tongues touched and danced, Max placed her hand back onto Denise's nipple and again pinched and flicked it. Denise continued to respond to Max's attention and Max reached between Denise's thighs with her free upper arm. Denise bent her knee to open her thighs, giving Max both permission and the ability to access her private bits.

Max took her time and enjoyed the feeling of her willing friend's body. She kissed her lips, working her lips and tongue against Denise's, responding to Denise's implied requests. Max pulled back, looked into Denise's eyes, and offered, "If you have any objections, say so now."

Smiling at her old best friend, Denise told her, "I cannot imagine anything you would do to me that would cause me to object."

"Good, than pay attention. I will teach you what I enjoy and you will repeat each lesson, you will practice doing the same thing to me until I move to the next lesson. Later, while you show me your skills at giving me the pleasure I desire, I will explore your body and we will learn what you enjoy."

Max kissed Denise as she reached down and pinched and twisted Denise's nipples. Denise repeated those actions on Max's erect nubs. Pleased with Denise's receptiveness, ability to learn, and demonstrative skills, Max showed her everything she wanted her to do, and as Denise complied and reciprocated, Max whispered her delight and pleasure into Denise's ear.

Finally, Max told her friend, "You were a very good student. You now know how to please me. Now, let me learn how to please you."

Max pinched, sucked, flicked, and kissed Denise's nipples as she massaged, squeezed, and caressed her large breasts. Denise echoed each of Max's actions and then showed Max what she wanted her to do to please her. As Max learned, the two ladies moaned in simultaneous pleasures for several minutes.

Satisfied that she knew what Denise liked and that Denise knew how to please her, Max moved her hand down to Denise's trimmed pubic patch and slowly massaged her pubes and later her labia.

Denise opened her thighs and offered herself to Max's probing fingers. After slipping her index finger between Denise's moist labia and into the wetness of her vulva, Max circled her finger inside Denise's pussy before pulling it out and sliding it up to Denise's aroused nub.

Denise raised her hips, wanting Max to place her finger back inside her pussy. Instead, Max tapped her index finger gently on the hood protecting Denise's clitoris before she put it under the hood, pressed directly on Denise's erect clitoris, and gently massaged it.

Two minutes later Denise shuttered and cried out, "Oh yes Max, like that!"

"You are your mother's daughter," Max cooed. As she continued rubbing Denise's nub, she explained, "You orgasm easily and often. I'll bet you love sex."

Between moans of pleasure Denise replied, "I liked sex with Michelle. I like sex with you—so far."

Max withdrew her index finger from Denise's clitoris and told her, "Okay, if you have no objection, I'm going to move on and show you some more pleasures."

"Please," Denise begged.

As she slid down Denise's body, Max kissed her chest, stomach, navel, and pubes along the way. Denise instinctively reacted to Max's gentle push, rolled onto her back, flattened her legs onto the bed, and spread them as far apart as she could.

Kissing Denise's labia, Max knelt between Denise's separated thighs. Denise responded, lifting her hips off the bed and forcing her covered clitoris between Max's lips. Max reciprocated, kissing Denise's nub and using her tongue to push the clitoral hood back before suckling her exposed clitoris until Denise again shuttered in an orgasm.

"Should I stop?" Max teased.

"Please, no!" Denise begged, putting her hands on the back of Max's head and lifting her butt off the bed to push her sore clitoris between Max's lips and teeth.

Max gently nibbled on the blood engorged and now raw nub for a second before she licked down one side and up the other spreading her saliva and Denise's orgasmic juices over Denise's labia.

Her hips still in the air, Denise begged, "Please!"

Max forced her tongue between Denise's pussy lips toward her vagina. After only a few minutes of attention Denise's vaginal muscles flexed and she convulsed in multiple orgasmic shutters.

When Denise again lowered her butt onto the bed, Max raised her head and with a big smile, asked her friend, "Why don't I get our wine glasses so we can cool off and rest?"

"Please," Denise whimpered.

They enjoyed the rest of their wine and Max again showed Denise how much she knew about pleasing Annika, and thus, about pleasing Denise. Denise showed Max and herself, how much she could enjoy sex. Especially, sex with a skilled, knowledgeable, and willing partner.

Later, as they slept, they took turns wrapping one another in their arms.

* * * * *

Early Saturday morning as they sat naked drinking hot tea, Denise in her easy chair and Max sprawled across the love seat, Max asked, "Do you remember when we were young, before I began working full time at the haberdashery and you went to Arts School, and we were best friends?"

"Yes, you were like the big sister I always wanted. You seemed to understand what I was thinking and what I needed to know," Denise answered, her eyes closed and a smile on her lips as she remembered life with an older friend that cared about her.

"Would you like to be friends again? Best friends?"

"Yes, I would. I miss not having someone I can talk with. Someone my age, who understands what I face every day, at work, trying to find someone to date, looking to find a lifestyle that works for me. How about you?"

"Yes, me too. We always seemed to hit it off when we were younger, but when you went to Arts School, everything changed. Would you like to try again?" Max almost begged.

Denise moved over to the love seat and sat next to Max, before she answered, "Yes, I'd like us to be best friends, and more. I'd also like to continue to see if we can be compatible lovers."

"Me too. I'd love to be your friend and to see if we could become lovers. However, why don't we take our time and move slowly. Let's just focus on our friend..."

Denise did not hear the last part, because she was lusting after Max's big, full, red lips, and Max could not finish her sentence, because Denise had leaned forward and kissed Max's lips. Denise did not relent, instead she showed Max how well she'd learned her lessons the previous night. In return, Max showed Denise the same desire, need, and lust Denise had shown her the previous night.

They spent the day naked in Denise's apartment. When they weren't sharing themselves in Denise's bed, they sat on the love seat, first reminiscing about their childhood together and then catching up on their lives since they'd drifted apart.

That evening, Max asked Denise if she'd like to go clubbing with her, but Denise politely demurred, telling Max, "Last night I cut my chat with Will—my Internet friend—short, saying I was tired and now I miss him. I don't understand why, but if I don't chat with him, I feel like something is missing in my life. I've come to rely on him more than I do my mother. I don't want to go another night without having a conversation with him. I don't want to cut him short two nights in a row."

Max grinned and teased, "It sounds like you really like this guy."

Denise frowned, "He's a good friend. Just a friend."

"Okay, have your chat with your just a friend. I have to go. Please, promise me you won't stay away so long this time."

As they kissed, Denise promised, "I won't, I'll make it a point to visit you at the Haberdashery the next time I visit mother."

"Great," Max exclaimed as she picked up her jacket and headed out to go clubbing in her revealing leather outfit.

* * * * *

Jaunt Preparations

Denise worked diligently to finish the preparations for her Jamaican Beauties Jaunt. The previous three Sunday afternoons and any other free time she had during those three workweeks she'd reviewed and collected her information on the attractions, museums, hotels, bed and breakfasts, restaurants, and nightclubs. This last week, she'd spent Monday through Wednesday evening and Thursday afternoon reviewing and revising the detailed itinerary covering each day of her Jamaican Beauties Jaunt tour.

Thursday evening, she reviewed her itinerary and was satisfied that it was, at last, viable and robust enough. She was happy that she could finally email the proposed schedule of her tour to Will. It was refreshing to relax and enjoy her wine without worrying about this or that detail of her tour.

Will's immediate response in their private chat that evening was, "Thank you for the marvelous schedule. I'm very excited about the tour. BTW: You may be the only person in this hemisphere that is more detail-obsessed than I!"

Denise smiled as she read the comment. She had wanted Will to be impressed with the tour; she wanted Will to enjoy the tour. She wanted Will to see and appreciate the beauty she saw in her Jamaica. She was pleased to learn that she'd already accomplished the first item on her list.

When Denise didn't reply, Will sent a request, "As soon as I receive your email with the price for the tour I will send you the money and once you've given me the dates for the tour and I've booked my flights I'll email you that information."

They continued to negotiate the terms for the tour and finally agreed that Denise would treat their tour as if Will were a regular customer. As the tour guide, she would be in charge of their itinerary, serve as the driver, and pay for all their expenses, except any shopping Will might want to do. However, Will insisted that he pay in advance for the full amount of the tour, including the costs for a rental car, all accommodations, entry fees, and the salary of the tour leader. Because this was her first tour, Will insisted she allow him to advance her a "bank" to cover the estimated costs for their meals, drinks, gas, and tips. They agreed that during the tour, Denise would use that bank, to pay for their meals, alcoholic drinks, incidental expenses such as gasoline, and any associated tips. However, because alcoholic drinks weren't included in the tour, Denise would keep a tab and Will would settle with her afterwards.

* * * * *

During the subsequent week while Denise was busy completing her tour arrangements, Will, made several more efforts to convince her to take a second week off from her job so that upon finishing the Jamaican Beauties Jaunt they could take a vacation enjoying the hedonistic pursuits available at a couple of Jamaican North-shore, all-inclusive resorts.

Monday morning, when she was talking with her mother on the phone, Denise mentioned Will's offer. Annika became excited and reminded Denise, "That would be a wonderful opportunity for you to be exposed to Americans, Canadians, and Brits, and to see how they live, love, and enjoy life. In addition, you might even learn to loosen up, enjoy life, and perhaps prove to Will that you're not a prude!"

Before Denise could respond, Annika added, "I know you had to overcome your anxieties in order to go on your tour with your European boyfriend and when he turned out to be a cad it was very difficult for you and nearly destroyed your self-esteem. I suspect, as a result, you felt you weren't appealing to men and you didn't deserve to have someone love you."

Remembering how miserable she felt when Lars dumped her, Denise muttered, "Yes, I remember."

Her mother continued, "But, if you'll remember, I tried to warn you about him, albeit at the last minute. Moreover, as for your current decision to take another man you've never met in person on another tour, I have not objected. In fact, I've tried to be supportive and to encourage you in that endeavor. Although, if you wouldn't mind, I'd be much more comfortable if I could at least meet this man before you left on your tour."

Denise frowned, but remembering that, as always, her mother really had her best interests at heart, she told her, "We'll be in Kingston for the first two days of the Jamaican Beauties Jaunt. If you wish, I could take Will to the Frigate for lunch the first day so you could coincidently pop in and I could introduce you to him."

"I would really like that. And, I'd be happy to give you my opinion of the gentleman." To stop Denise's forthcoming protest, Annika quickly continued. "I promise that you will be free to accept or disregard any opinion I share with you, but please remember that I am a psychologist."

"Thank you mother, I appreciate your offer," Denise answered in one more effort to avoid an argument.

Annika grinned and continued her discourse, "I do have to admit, from what you've told me and the emails and messages you've shared with me, Will seems to be quite different from that asshole Lars."

After they finished laughing at their oft-repeated little joke about the man that dumped Denise, Annika added, "Will's clearly more experienced and, I expect, more intelligent, fun, and sensual. As I'm sure you've already figured out, I like his advice to you about being open to new experiences, but I reserve judgment on his advice that you should be proud of your body and reveal more than a hint of cleavage. Don't misunderstand me. I agree with the advice and the basic reasons for it. I would just like to know in whose interest he is giving that advice, especially when he's offering to show you the hedonistic pursuits at an all-inclusive, clothing optional resort."

* * * * *

Wednesday, Denise completed the arrangements to take a second successive week of unpaid vacation. It turned out to be far less difficult than she had imagined it would be. Just as when she'd scheduled her first week off, the assistant accountant explained since she wasn't taking any classes during the summer she would be happy to work the extra hours and collect the extra salary.

Nor did the office manager, their boss, object to their plans. He had hired both girls because they were capable and polite, but primarily because they were both pleasant looking. He hated dealing with finances and he wanted to have someone in the accounting department who was both competent and attractive, so he would have something to look forward to whenever he had to go into the small office next to his to resolve an accounting or financial problem.

When Denise went to his office and to ask him if she could take a second week off, he stared at her cleavage and smiled, happy that she'd finally stopped wearing sweatshirts or buttoning her blouses up to her neck. He agreed to her request, but reemphasized that although it didn't matter to him which girl was working, whoever was there had to be available to answer any questions he might have and had to stay up-to-date with the accounts.

That evening, during their Internet chat, Denise informed Will, "I have arranged to take off a second week and I am looking forward to having you show me "Your Jamaica." In addition to the previously arranged nine days off for my Jamaican Beauties Jaunt (Friday June 10 until Saturday June 18), I've extended my time off from work through Sunday June 26."

Will replied, "I am ecstatic to hear that you will be joining me for my weeklong vacation at two North-shore resorts. Let me reiterate, you do not have to worry about the costs during our week at the two all-inclusive hotels. I will select all our activities and cover all of our expenses during the Hedonistic Pursuits Vacation."

Denise paused for a moment, wondering what would be included in "all our activities" but decided to take her mother's advice and focus her energies on enjoying her week as a tourist at a North shore resort.

The next day, Will booked his flights to and from Kingston and three nights at the first all-inclusive resort. Although the resort was generally conventional, it had a liberal attitude toward topless sun bathing. He next booked four nights at a second resort that offered a designated clothing-optional pool and beach as well as a conventional swimming pool, beach, and facilities, which they could use and enjoy in case Denise was unable or unwilling to overcome her inhibitions.

He then booked two nights in the Jamaican Pegasus Hotel in Kingston at the end of his vacation. His first reason was that the best flights (those with first class accommodations) between Dallas and Kingston via Miami arrived Friday morning, the first day of Denise's tour, but did not depart until the Monday morning after his vacation. Moreover, it would give him two days to do more touring in Kingston if he wished, or, if things worked out between them, to take his tour guide out for farewell drinks, dinner, and perhaps dancing.

Will emailed Denise the details of his flights and the dates and generic information about the resorts he'd picked—he didn't want her to be concerned. However, because he wanted to surprise her, Will did not let Denise know that he'd booked suites with separate bedrooms. Nor did he tell her that both resorts had both clothed and clothing-optional beaches, so she would have the option of going clothed, topless, or nude, depending on the lengths to which she was willing to go in order to prove to him she was no longer inhibited.

* * * * *

A Fitting Revelation

Thursday after work, Denise went shopping for some new clothes for work and her vacation with Will. Ever since the progressive challenges, she'd given up her usual sweatshirts, jeans, and sneakers and had begun wearing short skirts, revealing blouses, and heels to work. Because She'd accepted Will's offer to spend a week in hedonistic pursuits, she wanted to be sure that her clothes would be appropriate not only for her tour of Jamaica, but also for a week at a North-shore, clothing-optional resort. Denise didn't think she'd actually could, but she wanted to try to look like an American or British tourist on vacation. She returned to the three stores her mother had shown her when she was looking for clothes for the Progressive Challenges and when they'd gone shopping for clothes a month earlier.