Caribbean Awakening Ch. 01

Michael still tingled all over from the afternoon massage. He yearned to take the novel sensual experience to the next level and knew deep down that Laurie would be fully supportive of him meeting Roberto the masseur again that evening. While he had never done anything like this before and had never even imagined that his body would react this way, over the last year, he had learnt to trust his feelings and to sexually do whatever felt most natural to him.

He had not seen Laurie since mid-day but knew that she and her company team were planning a wild time at the disco tonight. In the meantime, Roberto, smitten with Michael's submissiveness and attractive lady-boy looks had eagerly agreed to Michael's suggestion to meet him at the same club. Michael therefore decided to go all out for the evening and to transform himself into a stunning beauty for Roberto. In the back of his mind he hoped to make Laurie a bit jealous as well.

He took his time getting himself looking his best to maximize his excitement from the afternoon. He carefully shaved himself with a fresh blade even though he had done so in the morning. Then after brushing his teeth he rinsed with a mouthwash several times. Stripping off the oily bikini bottom, he stepped in the shower and used the cold water to clean himself all over. He carefully shampooed and conditioned his sun streaked hair. He soaped himself paying special attention to his penis and his behind, making sure he cleaned everywhere. Gingerly he probed his still sensitive ass with soapy fingers to make sure that he cleaned off the massage oil from the exciting afternoon interlude. The jet of cold water rinsed away all the soap. Despite the cold, his erection was stiff all through the bath but in keeping with Laurie's wishes he did not relieve his need. Shutting off the water, he dried himself vigorously.

He applied the expensive skin lotion on his freshly scrubbed body making it smooth and soft all over. Combing out the water from his long wet hair he waited for it to dry a bit. He used the large curlers to help bring some more body to the hair. In the meantime, he started on his face, putting on the darker liquid foundation to match his now tanned face. The eyes took some time as he penciled in the mascara rather heavily for a smoky look and went with the deep brown eye shadow. Then he added long and curled eyelashes to complete the look. He had been to the salon just before their trip and his nails still looked good with the dark red enamel. Now he was ready to style the hair. He undid the large curlers and spraying on some body building conditioner, used a large round brush and the hair dryer to bring out the soft waves and the long fade away bangs and sprayed it into shape. Looking at the mirror he could see a mass of wavy hair in a flattering streaked blonde color. With a matching deep red lipstick and gloss coat he was now ready to put on his outfit.

With all of the care he was taking in getting ready, his erection had softened and he was able to slide it inside the tiny black lace thong he had picked out. The top he put on was a black silk halter that was loose with folds on top but tapered into ties that knotted at the back of his slim waist. The back was totally bare except for his long teased hair and the loose drapery on the front flattered his smooth chest well. The low cut black capri pants that went on next were also loosely cut but the silky material clung to his legs and behind as he moved. He put on his black velvet wrist straps and choker. With black strappy sandals encasing his bare feet, he was now ready to go. He quickly sprayed on some Obsession perfume as he prepared to leave the room for what he hoped would be a night to remember for ever. His heart was beating fast and he tingled all over with excitement.

Just 24 hours ago, he was depressed about his relationship with Laurie. When she had told him about how she planned to spend the time at the resort, he had worked himself to becoming distraught that he would be all alone while she cavorted with her team and the other men at the resort. He was also unsure where their sexual and emotional relationship was going next. The first day at the resort changed all that.

Michael's slim boyish figure was around five and a half feet tall and he weighed around 140 lbs. But his large penis was an exception to his slight frame. Erect it was a good seven to eight inches long with an impressive girth. In the past to make up for his size and build, Michael had sported a straggly mustache and goatee and had long dirty brown hair. But with the help of Laurie's friend Diane, his appearance and his demeanor had been changed to suit his inner self (author's note: please read "Michael, My Sweet Whore!" to learn about this part of Michael and Laurie's life).

He loved his new looks and made sure that his clothes and appearance pleased Laurie. Again with Diane's help, their marriage and sex life had both evolved so that they were very comfortable with expressing their inner desires.

Michael was now clean shaven and kept his body smooth and hairless. Laurie had taken him to a laser hair removal clinic and as the result his body was always smooth. Frequent visits to Laurie's stylist kept his hair in an attractive light brunette shade to which the sun had added natural streaks and highlights. Nowadays, Laurie only wanted Michael wearing the outfits that she picked out for him at her favorite boutiques or her pants and tops. He had grown to love the feel of the silky, soft and stunning outfits and definitely preferred them to shapeless jeans and t-shirts he used to wear. As an avid yoga fitness fan Laurie had ordered Michael to also follow a strict regimen to keep his body lithe and fit.

In many ways Laurie could pass for a clone of Michael. She too was slim and willowy and a couple of inches taller than him but a few pounds lighter. She worked out regularly and had a great figure, pert breasts with sensitive dark nipples, rounded and firm behind and silky soft skin. Her hair was styled in a short and sleek dark brown bob to suit her busy work lifestyle and she usually wore conservative business suits during the week.

For this vacation week however, she had packed a completely different wardrobe. Nearly transparent skimpy tops, micro-mini skirts and g-string bottoms with sun streaked gelled hair and lots of makeup should give her a trashy look. This look went with her plan to flirt and fuck shamelessly with the men in the resort. Michael would be seeing her getting groped and making out with her colleagues and other guests all through the week. She had told him that she intended to get her fill of thick hard penis in every part of her body this vacation.

Laurie loved Michael's shyness and her natural assertiveness and dominance came through in their relationship, and recently also in their sex life. Michael now was openly her submissive partner and she assumed full control over his appearance and sex life. While they had only enjoyed conventional sex before, they now had moved on to a new and very open lifestyle. Their relationship was now more akin to lesbian lovers, with Laurie enjoying Michael's skillful attentions on her pussy and frequently taking Michael with a strap-on. She had ordered Michael not to masturbate and recently she had also stopped using her hands to help him come when they had sex. Nowadays she let him climax only when she took him with the strap-on. Because of the more prolonged abstinences, Michael was almost in a perpetually aroused state and in a sexual high.

Laurie was also open in her relationship with Michael since their chance meeting with Diane. She did not mind having Michael please her friends in the same way that he attended to her needs. For quite a while after the trip to see Diane, she had continued her own monogamous arrangement with Michael even as she encouraged him to have sex with her friends. During this period, she had slowly ceased to enjoy having his penis inside her, preferring just his mouth and fingers instead. She also preferred satisfying herself by taking his lithe body with a strap-on.

Since the trip to Napa, this pattern too had evolved a bit as Laurie reacquainted herself with hard cocks. During the trip she had slummed impulsively with their black chauffer and liked the experience immensely. She learnt that she also enjoyed being a slut as well endowed men rammed her every orifice – Michael had watched her fuck the driver and ate her creampie in Napa. Now she wanted to experience more of the same. Michael expected that before this vacation was up that she would be well acquainted with the manly equipment of her male colleagues and several other the bulls at the resort.

Laurie had successfully handled a very important assignment for her IT consulting company at a major client in Japan. The Tokyo trip she undertook had extended to nearly two weeks and had been mentally and physically exhausting. During the trip she had made Michael stay with Carol, her friend and owner of a high-end sex boutique. But upon her return from Japan, she became jealous of Michael's sexual experiences with Carol and the intimacy he seemed to share with her. The two of them then took a short trip to Napa when Laurie opened her legs wide to another man, partly to payback Michael for his straying with Carol.

Just a week later they found themselves at this exclusive and private Caribbean resort courtesy of Laurie's very grateful company. Her team had been selected as the top performer for the year and the trip was part of the reward package. During this sojourn, Laurie hoped to repeat her Napa experience at the resort and packed accordingly. She was horny for cock and looked forward to sharing more than her work with the men in her team and hoped to find other well endowed men at the resort.

Flying to the resort seated next to her in a nearly deserted first class section, Michael first heard Laurie's wanton plan for the trip. She told Michael that she hoped he would find a partner or two at the resort as she was going to be spending most of the time getting soaked with cum from her company friends and strangers. She encouraged him to try out new vistas and experience the resort's amenities and the spa as the company was paying for everything. Hearing this Michael felt a twinge of sadness and regret at having strayed further away from her. He felt guilty about his intimate time with Carol and how in his sexual excitement, he had not really missed Laurie's absence. He hoped that after this holiday, their relationship could get back to the way it was. In a way, he was now weirdly jealous of Laurie's potential sex partners.

However, they were holding hands and he felt safe and warm next to her. He snuggled up next to her and she rested her head against his. Soon they had had several drinks each. The heady liquor made them light headed and uninhibited. Laurie squeezed his hand and placed it on her damp crotch indicating her arousal. The lights had long been dowsed because it was a red eye and there did not seem to be anyone around. Michael ever compliant to her need felt himself stir in response to her excitement. He slipped down and onto the bottom half of her stretched out seat. Raising her thighs from the cushion and pushing up her very short skirt with his hands, he began kissing her smooth crotch all over. As his lips caressed her inner thighs, he reached up and slid her wet thong down her legs. He then spread her wide and hungrily kissed her moist bare pussy.

He gave her slit a good finger workout pushing in and out of the wet folds. The pussy lips quickly became swollen and flowing with her arousal. Moaning she twisted and stroked her sensitive nipples through her flimsy top, enjoying his services. His tongue licked her fragrant slit in long strokes lapping up her juices. He spent his time slowly laving her outer lips teasing her with his tongue. Her fleshy clit reared up eager to feel his attentions. When his tongue finally brushed all over her clit she grabbed his ponytail urgently and ground his face up and down on her pussy. As he feverishly licked her fleshy knob, she tensed up stiffening her body. She came hard bucking on his face and had to bite down on her lip, clenching her fists in his hair to stop from screaming aloud.

Enjoying the afterglow, she started to relax when she felt something new and very dirty. Michael had pushed his hands under her bottom raising it up towards him and his tongue was now laving the area below her pussy and then licking her asshole. She was going to push his head away, but a thrill shot up her spine and she tightened the hold on his hair to hold him steady. His tongue traveled up from her asshole to her clit and then back down again, probing inside the puckered opening like a small cock. She didn't think anything could feel so good but his probing tongue sent electric chills up her spine. Then his fingers began stroking her clit and with his tongue continuing to lick her rear, she climaxed again, this time shuddering into a long and slow orgasm. It must have lasted for minutes before she pushed Michael away, breathing heavily. She pulled him up towards her to kiss his wet face and her tongue invaded his mouth tasting her juices. Michael certainly knew how to use his mouth and fingers to take her to the heights of pleasure. She felt his stiffness pushing urgently against her body but spitefully decided to deny him release. She had realized that he must have learnt the ass licking from his time with Carol and her jealousy took over. Pushing him off to his seat she rolled to her side drifted off to sleep Exhausted Michael too stumbled into dreamland very soon, with his cock still engorged and unsatisfied.

At the resort, they spent the first morning in their suite trying to get some sleep and recover from the overnight flight. After a late room service lunch, Laurie put on a wisp of a bikini – a halter top with tiny yellow triangles covering her nipples and a high cut thong with a correspondingly small sized fabric swatch in front of her bare slit. She looked naked from the back. Michael could see that the small front of the panties was already discoloring from her excitement. He knew that she was aching to get some cock from just about anyone at the resort. Laurie gave him a quick peck on the cheek as she grabbed and stroked his cock through his bathrobe. She told him that he should go down to the beach for a while and then head to the spa for an appointment she had made for him at 4pm. She was going over to the bar where she hoped to meet her team for drinks and more. She said that she loved him and hoped that he would have a good time in the afternoon and be up to meet her and the team tonight at the nearby disco for some serious partying.

After she left Michael decided to not sit in the room all by himself but make a day of it. The resort looked lush and pretty and he could hear the surf at the beach. The spa too promised to take his mind away and he needed something relaxing like that. Laurie groping had stiffened him again and not having come for a while he needed to do something. He picked up a reasonably conservative bikini bottom to wear. But thinking of Laurie's scanty clothing he threw caution to the wind and picked up a very small g-string bottom that Laurie had packed for him. It was like a piece of elastic black floss and rode high up on his waist with a tiny piece going down between his ass cheeks and expanding into a soft pouch between his legs that concealed held his penis securely. For a top he selected a short white tank top. The thin cotton was cut loose and ended at the top of his trim stomach nicely showing off his belly ring. He put his long hair in a ponytail, applied some lip gloss, put on an oversize pair of dark glasses and a pair of coir sandals and slipped out of the room.

Strolling to the beach, he caught the eye of the few guests at the resort and some of the staff. Roberto was one of the staff eyeing him. Roberto immediately coveted Michael's slim body. His mind quickly fantasized about using a compliant Michael. He envisioned Michael's lips wrapped around his stiff rod and pounding Michael's petite frame hard. Roberto enjoyed dominant sex, especially with slim and fragile looking partners. He preferred effeminate boys and the occasional submissive woman. He loved using their mouths and their pretty bottoms for his own satisfaction. The resort provided ideal fodder for Roberto's special lust. As a massage therapist, Roberto had a fairly easy job in getting his hands on the right partners. Every other week, his radar would detect a potentially compliant guest whom he would seduce during the massage and then take his pleasure somewhere else on the island, typically to mutual satisfaction. Today he hoped would be no different. He had last slaked his lust well over a month ago and his cock twitched for something smooth and submissive. He was in heat and needed a silky soft bitch.

The attentive waiters plied Michael liberally with rum coladas and he was soon feeling painless. The tanning chairs looked inviting and he decided to take in the sun. Lying on his back he reached for the tanning lotion that was available next to the chairs. Just then the sun was blocked by a large staff member who asked Michael if he needed help with the tanning lotion. Before Michael could reply, the staff member picked up the lotion and was pouring it into the palm of his large black hand. The staff member was Roberto and he grabbed the opportunity to gauge his chances by getting his hands on Michael.

Brusquely, Roberto took control and helped Michael lie down on his stomach. He pulled off Michael's tank top saying that tanning oil would damage the fabric and that Michael would not want tanning lines on his body. Sensing Michael's innate submissiveness, Roberto progressed to the next stage and began feeling the rest of Michael's body. Roberto started rubbing the sun block at his neck and moved over his slim shoulders and then down his arms. It felt more like a sensual rubdown to Michael than a quick covering of sun block. Roberto liked groping the smooth and sleek form and enjoyed stroking the compliant Michael's lithe limbs. Roberto did not miss his sides and as he reached around underneath to his front, Michael wondered if he purposely felt up his nipples.

Roberto ebony hands rubbed more of the oily sun block onto Michael's pale back and down to his string bottom paying special attention to the two ass cheeks. Michael felt his rod getting excited as Roberto started on the tops of his thighs and the bottom of his ass. Roberto could see Michael's arousal as he made sure the lotion did not miss an inch of his body, leaving Michael panting with desire.

Michael had not seen Roberto very clearly but enjoyed the long and powerful fingers coating him with slick oil. But before Michael could take a better look Roberto finished up and walked away. Just then, another waiter handed Michael another rum colada. Soon the drinks and the sun helped Michael doze off on the chair. Roberto had already figured out that Michael was compliant and receptive and he definitely wanted to have his way with this guest/quarry. Having done this many times before, Roberto knew just how to make this happen.

Just before 4pm a staff member woke Michael up with a refreshing glass of ice water with lemon and courteously directed him towards the spa. As he was escorted to his spa room and the attendant told him that his masseur should be there momentarily. An hour ago, Roberto had arranged the schedule with the other staff to make sure he would be the one taking care of Michael. Roberto's plan was to further build up Michael's excitement during the massage so that he could arrange to meet Michael away from the resort at night and have his way.