Dianas Tales Cruising Pt 02

Disclaimer - All characters are 18 or older.

Author's note - This story was written in collaboration with Diana R.

For those familiar with other editions of Diana's Tales, then you already know what you are getting into if you proceed. This story (like all of Diana's Tales) straddles the line between reality-based fiction and the ridiculous. Racial stereotypes abound. Promiscuity and infidelity are flaunted. If any of these are triggers for you, please find another tale more suitable to your palate.

*****

Diana's Tales: Cruising Pt. 02

*****

I returned to the ship after my beach encounter with Miguel. I was sitting poolside before heading to dinner in an hour. I saw my friends from last night, Javier, Chan, and Nigel, had lit a spark with some other young ladies also on spring break like themselves. They playfully splashed about in the water and held each other. I don't even think they noticed me at first, and I'd almost swear they were purposefully avoiding eye contact with me, although Chan did end up given me a muted wave hello a while later.

Although I wanted to be happy for them, I was admittedly a little disappointed, even though I couldn't blame them. After all, I'd just explained earlier that afternoon to Miguel how we were basically strangers having no strings attached sex. I knew any sex I had on this cruise fell under that code, and though I knew I should be thankful for the time I spent with them last night, the fact they had moved on to other women still stung. I saw my younger competition with their young, firm bodies, and I wasn't sure how I could compete. Besides, they each had their own girl they were shamelessly flirting with, as opposed to last night when they all had to share me. The numbers worked in my favor last night, but I could understand why they would each want a female companion of their own.

Feeling blue and a little less than desirable, I ended up retiring early to my cabin for the night and calling room service for dinner. A half hour later, there was a knock at the door.

"Room service," a voice called out. He sounded familiar somehow, although I couldn't quite place it.

As I opened the door, Ramon, the porter who brought my bags to the room on the first day stood there with a cart carrying my meal. "Ms. Diana, it' s a pleasure to make your acquaintance again," he said warmly. "Please, let me bring your dinner into your room."

Ramon stepped in, and I closed the door behind him, happy to see that he remembered me. Maybe I'd actually made an impression on him on that first day. I know he had certainly made an impression on me.

"Are you feeling a little under the weather, if you don't mind my asking? We offer so many dining options, I'm surprised you are not out enjoying all that we have to offer. A lovely lady such as yourself could be living it up."

"Oh, I've felt better I suppose," I admitted. "But this is lovely. I'm sure I'll be back out to exploring the ship tomorrow."

I sat down and admired his body as he finished preparing my meal. He set it up on a nearby table, placing the plate on a mat with salt and pepper shakers as well as silverware and napkins. He was dressed in the standard worker uniform for the ship. Khaki pants and polo shirt.

"You're serving people all day long. When do you have time to eat?" I asked as he finished up setting the table.

"This is actually my last task for tonight. I'm off the clock after this," he replied with a smile.

"Do you have plans for tonight? Would you care to join me for dinner? I ordered way more food than I could hope to finish. My eyes are always bigger than my stomach."

"Oh, I'm honored, but they don't like us mingling with the guests like that," he replied, clearly trying to let me down easy.

I was still feeling the sting from Javier, Chan, and Nigel moving past me, however, and Ramon must have seen the disappointment on my face.

"I don't mean to offend," he quickly apologized. "It's just, we're here for a job. Some people are unscrupulous, and they'd try to take advantage of guests."

"I don't mean to get you in trouble. I just figured it's nice to have some company and good conversation. I bet you have a girlfriend, anyway."

"Actually, I don't," Ramon admitted. "I'm always away from home to work on cruises, so it makes relationships hard. Some people will try to take advantage of it. Some of the staff would spend all their time hitting on guests, basically harassing them if they didn't have some rules in place."

"Oh, I can imagine. Still, it's too bad they discourage you from fraternizing with the guests. You have needs too," I pointed out. "After all, what's a little fun between adults as long as everything is consensual, and no one gets hurt. I mean, especially if you're off the clock now."

I knew I was guilt tripping him, and I saw the struggle on his face. I smiled earnestly at him, and I could see him looking me over, trying to decipher my intentions. I had flirted lightly with him when he brought my bags to the room, and now I was practically begging him to stay. It shouldn't be hard to read between the lines, but I decided to clear up any mystery for him.

"Just so you know, you wouldn't be taking advantage of me. If anything, I'd be taking advantage of you. We're both adults, and you yourself said you're off the clock. I'm a grown woman, and I can take care of myself. I won't force you to stay. I would never do that."

I could see how uncomfortable he felt. His mouth was almost salivating, but his eyes were darting between me and the door, a worried look on his face, the threat of reprimand from his bosses clearly weighing on his conscience.

"It's okay, you're unsure. Maybe it's not meant to be," I said, finally breaking the awkward silence.

"Please, don't be offended. You're a lovely woman. If it was normal circumstances, I'd - " his voice dropped off.

"I understand," I assured him.

Ramon hung his head in shame as he turned to leave.

"Your tip," I said, as I held out a bill.

"It's okay, keep it. When you're done with the meal, you can just leave the cart outside in the hall. Someone will be by to collect it," he said somberly as he trudged off.

Well, this is a hell of a night, I thought to myself. The cart had a chilled bottle of wine in a bucket of ice, and I immediately grabbed it, figuring it was best to drown my sorrows. I poured myself a glass and pondered my own disappointment. I had fun with Miguel on the beaches of Escambron that afternoon, but this whole evening had turned into a train wreck. I couldn't help but truly feel my age, and the thought frightened me. I'd heard my other girlfriends complain at various points how they felt invisible to men as they turned older. I'd resolved that would never happen to me, but now I wondered if I was relegated to the same fate. Maybe time, my age, was finally catching up with me.

Next door, I heard the newlyweds in the throes of passion, obviously enjoying each other's company. It only further depressed me, and I turned up the volume on the tv to try to drown out the bride's shrill cries of pleasure. I poured myself another glass and drowned my sorrows, falling asleep on my bed watching reruns of shows that I remembered watching as if it was yesterday, although it pained me as I realized those shows were older than the newlyweds next door.

*****

I awoke the next morning to a knock on the door.

"Housekeeping," another familiar voice called out.

As I wiped the sleep from my eyes, Felix stood expectantly in my entryway, his eyes hopeful for a rerun of yesterday's sex romp. In my eyes, he was like a dream, a reprieve after the rejection I'd endured the night before. He was validation that some young men did still find me attractive, that maybe I wasn't destined to be just an afterthought.

A thin smile formed on my face. "Close the door," I told him. "We only have a little time to play since you're on the clock."

He excitedly stripped off his clothes and jumped into bed.

"Do you always sleep naked?" he asked as his eyes feasted on my body.

I nodded in the affirmative.

"Naughty, naughty boy," I playfully scolded him. "I thought the workers weren't supposed to have relationships with the passengers."

"Well, I won't kiss and tell if you won't."

"Tell me, how old are you?" I asked, curious how badly I was robbing the cradle.

"21. Am I too young for you?"

"No, I'd say you're just perfect," I replied as he spread my legs and prepared myself for him to enter me.

Ten minutes later, Felix was done having his way with me, and I laid in bed, a fully satisfied woman with his cum dripping out of my pussy and a smile on my face.

"Same time tomorrow," Felix asked hopefully.

"I'll be waiting for you. You give excellent room service," I complimented him. He laughed as he opened the door to leave.

"Oh, there you are," a woman's voice called out. We're out of toilet paper if you could - "

Then I heard a gasp as the young newlywed bride stood just outside my door and caught sight of me naked on the bed. Felix quickly closed the door, but there was no doubt she knew that Felix was doing more than just making my bed.

*****

An hour later, I was freshened up, and left my room to find the day's adventures. As I closed the door, the newlywed bride stepped out at the same moment with her husband. She looked at me indignantly, and I felt the weight of her judgmental stare. Her husband, on the other hand, looked at me in a different light, almost as if he was looking upon me as a sexual creature for the first time. I figured she must have confessed her suspicions to him, however, unlike her outrage, he seemed to harbor curiosity. She couldn't help but notice his interest and gave him a sharp elbow jab.

I shook my head and moved past them, making my way to the main deck. As I stepped out into the bright morning sun, I was pleasantly greeted by the gorgeous landscape of Montego Bay. As I stepped off the boat, there were various buses staged to ferry people to local destinations, and I was contemplating which destination to explore when a booming voice called out in a thick Jamaican accent, "Hey there, sexy, what is a beautiful woman like you doing all alone?"

I turned around and was greeted by the sight of a 6'2" chiseled Adonis of a black man. He smiled, and his gleaming white teeth contrasted sharply with his coal black skin. The sight of him left me shaking in excitement.

"Welcome to Jamaica. I could be your tour guide if you like," he kindly offered.

I'd read about older women who visit Jamaica and end up in relationships with young local men. I knew right away that's what I was facing. There's no such thing as a free lunch, as they say. For the women, it gave them companionship and sex with men more handsome and younger than they could ever attract back home. Back at home, those older women were expected to be grannies who acted with propriety, but here they were free to pursue their lust fueled fantasies in a foreign land where their friends and family could not judge them. For the men, the women often showered them with gifts and money that their country's poor economy otherwise afforded little chance of obtaining.

I immediately recognized that was likely the case here, but I made a brief calculation and quickly decided our relationship could be mutually beneficial.

"And your name is?" I said with squinted eyes.

"Sanka," he replied in a deep booming voice.

"Sanka, it is a pleasure to meet you. I am Diana."

He took my hand and bent down to give it a kiss.

"Sanka, tell me, where would you take me?" I asked, curious what kind of services he would offer.

"What does the lovely lady like to see?" To the Doctor's Cave. To the Rose Hall Great House. Or all women love shopping."

He stepped up close to me, and he was tall enough that I had to crane my neck to look up into his face.

"Shopping sounds nice," I replied. "Maybe I can model some outfits for you, and you tell me what looks good on me."

"Perfect. But it is the woman who makes the outfit. I can already tell you that everything will look lovely on you. There's a shopping district just a short cab ride away."

"Flattery will get you everywhere," I said with a laugh.

"It's not flattery if it's true," he said with a wink.

A few minutes later I was modeling various bikinis for Sanka. It was a small shop with a tiny changing room in the back corner and only a small curtain for privacy. The curtain didn't quite close all the way, and I caught glimpses of Sanka eyeing me as I changed outfits.

Each bikini I tried on was skimpier than the one before, as I went from trying on a French cut bikini to a thong and then a G string.

"Wahoo!" Sanka applauded with excitement as I emerged with an ever-shrinking bikini. "You have a banging body. Show off them curves, mama. Sexy, sexy."

I ended up buying the thong and the G string bikinis, figuring they would come in handy later on in the cruise, or maybe even later that day.

"How about something for me?" Sanka protested. "If am I with such a beautiful woman, you want me to look good, also, right?"

I knew he was hinting that I should buy him a treat, and soon he had a new pair of Air Jordans to replace the sandals he was wearing.

As we emerged from the shoe store, Sanka's hands were all over me. Part of me wondered if I was almost paying for sex, although I could feel how firm and taut his muscles just from when his arm draped across my back, and I quickly decided that it was a wise investment.

"What would the lovely lady like to experience next in Jamaica?" Sanka asked.

"I'd like to experience Sanka," I answered eagerly.

"Wahoo, I love a woman that knows what she likes!" he exclaimed. His voice radiated a jubilant excitement. "I can give you all the Sanka you can handle."

A few minutes later, we were checked into a local hotel. The front desk clerk eyed me suspiciously as I registered for a room. When Sanka left briefly to examine the tropical fish tanks in the lobby, the clerk leaned across the counter and whispered, "Ma'am, I should warn you that he is just using you for your money."

"It's quite alright," I answered with a wink. "Trust me, I'm using him every bit as much as he's using me. I'll be on a ship by nightfall and will never see him again."

"Very well then. Room 336," the clerk said tersely as she handed me a key card. "Enjoy your stay."

I waved the key card at Sanka, and we were on our way up to the third floor.

I entered the room and walked over to the sliding glass door by the balcony. I was momentarily mesmerized by the sight of the white sand and blue waters of the beach below when Sanka came up behind me and his strong hands gripped my shoulders while his mouth leaned in to kiss the side of my neck.

"You said you want to experience Sanka. Are you ready?" he asked.

"I've been ready since I first laid eyes on you."

"I can tell you came to party," he said as his hands raced across my body.

He pulled the straps of my dress to the side, and the garment slipped down off me, leaving me standing in only my sandals and a thong.

"You have beautiful tits," he commented as he leaned over and suckled on them. "So firm and juicy."

The curtain right behind me was wide open. "What if someone sees us?"

"Then they will see that I am making love to a beautiful woman. What is there to be ashamed of?"

My arousal was quickly overcoming my common sense as Sanka's hand slipped inside the waistband of my panties and his fingers began to probe my pussy.

"You're a wet mama, ain't you?" he declared.

I leaned back against the glass sliding door as he pulled my panties down and inserted a finger fully inside me. I spread my legs slightly to let him access me even more easily.

"Oh God, I've been needing this," I sighed.

Sanka knelt on the carpet, and he brought his face to my pussy and inhaled deeply.

"I love the smell of an aroused woman," he said aloud.

I could only smile at his awkwardly obvious observation.

And then his finger spread my labia, and he began to lick my exposed pink flesh.

"Oh God, that's it," I sighed deeply.

"You just enjoy yourself, and let Sanka take care of you, Diana."

The stimulation of his tongue made me lean back even more heavily against the sliding glass door, and it suddenly slid open, causing me to fall backwards naked onto the balcony. I felt the warm ocean breeze and the smell of salt water in the air. As I regained my balance, Sanka directed me to sit on one of the wicker chairs on the balcony.

I sat down and then spread my legs, inviting him to continue pleasuring me. He smiled naughtily as he scooted over to me on his knees. Then he buried his face back in my pussy and resumed eating me out.

We were only three stories up, and I could hear people, mostly tourists, passing on the walkway just below. Luckily, the balcony had a solid concrete wall for a guardrail, so no one could see what Sanka was doing to me. I raised my legs and rested my knees on his strong shoulders as he continued administering cunnilingus to me.

I leaned back in the seat and placed my hands on the back of Sanka's short dreadlocks as his tongue worked magic on my pussy. He found my clitoris, and I knew that I was like putty in his hands.

"Oh, you're so good at this," I marveled. He looked up briefly, his pearly white teeth grinning at me, the juices of my arousal practically dripping off his chin.

"You want the full experience, right?" he intoned as he stood up before me. I licked my lips at the sight of his defined arms, his six pack of abs, and strong chest. He was 6'2" of pure manhood, built like a professional athlete. Then he dropped his pants and 8 inches of dark chocolate appeared, and suddenly my eyes were transfixed on his massive shaft. He was fully erect, the veins in his penis nearly popping out. It slowly swung back and forth before me, almost like it was placing a hypnotic spell on me.

"Is this what you came here for?" he asked.

"Yes," I whispered hoarsely, barely able to talk. I'd had many affairs over the years, and I was used to being in control of sexual situations, but I felt completely at Sanka's mercy.

He was an impressive physical specimen, and he knew it. He lifted my feet onto his shoulders as I lay spread before him while he positioned himself to enter me. My eyes nearly rolled to the back of my head as his manhood parted my pussy and the head of his cock easily pushed into my soaked pussy.

"Welcome to Jamaica," Sanka smiled as I took in the full length of his cock.

I was conscious of all the tourists and passerby's only a few floors before, and I tried to keep my voice down, but the effects of his cock and my arousal overwhelmed me. My body convulsed involuntarily as he thrust himself into me.

"Is this what you came here for?" he asked, repeating his earlier question.

I couldn't even speak, but I whimpered softly, fighting to control myself. My arms reached around the back of the wicker chair to brace myself as he slowly ground himself into me, his cock turning my pussy into a gaping hole as if he was parting the Red Sea.

My eyes welled up with tears, and I cried softly in pleasure as Sanka reached down and fondled my tits as he continued to plow my pussy.

"You're so big," I finally answered him.

"I love seeing a mature woman like yourself lose your inhibitions."

He was right. I had completely lost any sense of propriety, of decency, of shame.

"You brought me outside on purpose, didn't you?" I asked him.

"You looked so elegant and sophisticated when you stepped off that boat. But I knew deep down inside what you wanted. I knew you were a cougar on the prowl. Did you find what you were looking for? I know I did."

I growled at him, spreading my legs wider. "Fuck me harder," I told him, no longer trying to keep my voice low.