Shattered Hero

Its been a long time since I've contributed a post, but for years, unfortunately, there have not been any escapades in my life worth writing about. Since my last story, I've gone to law school and, until a few days ago, I worked at a large firm in New York.

Law school was bad, but working as a first year Associate was worse - far worse. A good week was 70 hours. A bad week was 100. I was on the road almost constantly researching cases and meeting with clients. I spent four or more nights a week in some hotel room somewhere - many were quite nice, courtesy of overbilled clients, but I didn't have the time to enjoy them. I made a lot of money, yet didn't have time to spend it. My apartment had a bed, yet it was still filled with moving boxes, unpacked since I moved in a year ago.

After 15 months of exhausting work, I finally took a much needed vacation. Without much planning or forethought, I booked trip to Antigua with mileage and hotel points. I thought I might as well get something in return for all that work related travel! This is the story of that trip and how it changed my life.

Day One

I left early on a Saturday morning. I stretched out in my first class seat and promptly fell asleep, stirring only on arrival. Going straight to the hotel, I checked in and was shown to a luxury suite, complete with private balcony and a view of the ocean. I had packed quickly the night before, throwing the few bathing suits I owned and some summer dresses and shorts into my bag. Now that I was in the hotel, I sorted through the bathing suits and found one that still fit half decently, or should I say, half-indecently.

I still have a great body, though I will admit I've put on a pound or two over the last year and gotten just a bit softer; visits to the gym are few and far between. Not having seen the sun in months, I was also as pale as the sheets on my large and inviting bed. Nonetheless, checking myself out in the mirror, I thought I still looked pretty good. Slim waist. Good hips. At the age of 29, my D cup breasts stood out proud, firm, and full. I was satisfied with how I filled out my suit and felt ready for some fun. I soon wandered out to the pool to get some sun. Absorbing as much vitamin D as possible, I dipped into the water to cool off periodically.

After a couple of hours, I ordered a massage and went back to my room. When I arrived, a tall, incredibly attractive Black women with long braided hair was setting up the massage table and heating up her oils. She introduced herself as Dani. I stretched out face down on the table and she began her magic, first on my tight and knotted shoulders, second on the small of my back, and then, starting with my feet, she worked her way up my muscled calves and thighs. She was a goddess - and it felt heavenly. I felt the waves of exhaustion roll through my body - and then evaporate into the tropical air.

After I rolled over with some effort, Dani started on my front. She rubbed my neck and shoulders, and then started kneading my large breasts. It had been so long since anyone had touched me there. As she applied more oil, my sensitive nipples grew erect and hard. Tingles began to race through my body. Dani then switched to my feet once again, working her way back up my legs. At this point, I could feel myself oozing from my long neglected vagina. Even I could smell the musky odor emanating from "down there." As her hands got ever closer to paradise, I drifted into a pre-orgasmic stupor. All I could think about was the amazing sensations rippling through my body - and all I could hope was that the masseuse would continue her tender ministrations.

Finally, she began rubbing around my cleft, where my legs join my torso. I raised myself a bit, silently pleading with her to continue higher. Dani's fingers started on the outside of my labia. I felt myself gush. Now slippery from my juices, her fingers continued to massage my vulva.

Moaning loudly, I subtlety urged her on. One finger penetrated me, the other started circling my clit. I don't know how long this continued. I was dazed, lost, unable to comprehend anything other than the intense pleasure that was sweeping through me. At long last, a delicate finger brushed the tip of my clit - and I exploded like a rocket bound for outer space, and indeed, I think I left the earth's gravitational field for a minute or two, positively levitating myself off the massage table.

As I was coming back to earth, I felt an incredible new sensation as Dani's tongue replaced her fingers, lapping up the flood between my legs. Soon, her licking was supplemented by a gentle sucking on my clit. My normally little but highly sensitive nub grew to what felt like enormous proportions. It was engorged, a tiny dick that needed to be licked, nibbled, and sucked - and my masseuse appeared more than willing to fulfill my need. This time, I felt myself traveling to the stars - perhaps beyond, to heaven.

Exquisite pleasures flowed through me until I could not hold back any longer. I gave into a wonderful, shattering organism the likes of which I had not known for over a year. Dani scooped up the quivering mass of protoplasm that was me and carried me to the bed. She kissed me softly on the lips, then pulled the sheet over me. I mumbled something about putting a huge tip on my bill, and immediately fell into a deep, deep sleep.

I woke around 11 PM feeling better than I had in a very long time. A massage, two wonderful orgasms, and a good sleep will apparently do wonders for a working girl. It was late but I was starved, not having eaten since breakfast.

Feeling wonderful, I quickly took a shower, got dressed, did my makeup, and went down to the hotel bar in search of food and fun. Dani had awakened something in me that had been forced into dormancy for the last year. Or perhaps it was vacation time on a distant tropical island where I knew no one. I had sex on my mind, and it was a delightful thought.

The restaurant was closing at that late hour, but the bar was still serving food. I ordered a nice glass of wine and a steamed local fish and began to check out my surroundings. It appeared that most of the guests were there as couples - or at least had hooked up with one another by that time of night.

Over in the far corner was, however, a single guy who, from my distant vantage point, did not look too bad. I watched him for awhile. He looked reasonably tall, though he was sitting at a table so it was hard to know for certain. No obvious defects. Yet, he was alone. I glanced in his direction periodically, waiting to see if a woman or perhaps even a man - you never know - returned to keep him company. By the time my fish had arrived and I quickly devoured it, I gathered he was alone - at least for the night. I decided to join him and, in what for me is still a bold move, picked up my wine glass and asked if I could sit with him. He introduced himself as Brandon.

Reciting the usual orienting facts, he said he was a real estate developer from Chicago who was on the island with his boss looking at properties for his company. He was actually pretty cute up close and we connected over shared jokes about being single at a resort hotel on the beach, though he was working and I was not. We chatted for awhile and then he excused himself, saying he was meeting his boss early in the morning and needed to get some sleep. Sensible man I thought to myself. Foolish, because he almost undoubtedly would have gotten laid if he had continued to play his cards right. But sensible.

As he walked away, I noticed first his beautiful rear end, and then that he had a small limp. A few moments after he left, he came back and asked if, perhaps, I might be free to join him for dinner the following night, at a more sensible hour. We made plans to meet at 8 PM in the lobby. With little other action in the bar, I went back to my room with a small smile on my face, hopes for tomorrow, and a still empty pussy that wanted - no needed - to be filled.

Day Two

I woke late the next morning. After a room service breakfast served on my balcony, I decided I needed a new bathing suit. The one I wore yesterday was quite nice, but the others looked, well, too conservative. At the hotel store I found a Brazilian bikini that was far more revealing than anything I'd ever worn in public before. The top showed my enormous breasts to their full advantage - covering only the areolas and nipples, but leaving little else to the imagination. The bottom was barely a ribbon in the middle with two ties on the sides. The strip disappeared into my crack, barely covered my labia, and let a few hairs poke out from my landing strip. It was perfect - with the matching semi-transparent cover-up. I then booked myself for a catamaran cruise for the afternoon that promised swimming and snorkeling on a reef several miles off the coast.

At 1 PM, I showed up at the dock and was helped aboard the boat by two handsome crewmen. One, a giant who towered above me and had, perhaps, the broadest shoulders I've ever seen, introduced himself as Paul. Long, curly sun-bleached hair covered his head, and a short, stylish beard completed the look. The other, quickly introducing himself as Sam, looked almost petite by comparison, but was probably about normal height. He had the most beautiful blue eyes. The afternoon had potential.

The other passengers ranged from couples in their forties to a group of young 20-somethings who were already one-sheet to the wind, so to speak. Paul and Sam were very solicitous. As I lay out on the foredeck in my new swimsuit, they quickly provided a towel, applied more lotion than absolutely necessary to my back, and offered cool drinks. As the boat moved toward the reef, I chatted with a couple from New Jersey, probably in their late forties. The woman, Janice, was a beauty: maybe 5'10", toned abs, long blond hair, and a nice if slightly saggy pair of tits. John was fairly good looking as well, though as with many men his age he had a bit of a paunch. We made small talk in the wonderful sun and breeze until we arrived at our destination.

Paul and Sam helped everyone into their snorkel gear, making an extra effort to adjust my equipment. The water was delightful, the fish were beautiful and plentiful, and we even got to swim with a few harmless sharks.

After an hour or so in the water, I climbed back aboard the boat and dried off. If my suit had left little to the imagination before, it left none now. After some pretty vigorous swimming, it had apparently drifted completely up into my vaginal opening, leaving my labia on either side of the narrow strip of fabric. No wonder it had felt so good! As discretely as I could, but knowing that both Paul and Sam were staring pretty intently, I adjusted myself and reclined once again on the foredeck. The two crewmen were on me in a second, offering whatever assistance or beverages they could. They were not very subtle, but I enjoyed the attention.

As we approached port after a long afternoon in the sun, water, and then more sun, Sam quietly asked if I wanted to continue the tour to the neighboring harbor where they were due to pick up a group for a dinner cruise. He explained that the other docking area was about equidistant from my hotel. I knew immediately that more was being offered. Taking a hard look again at Paul and Sam, I accepted.

After the other passengers disembarked, and saying a special goodbye to Janice and John, who said they hoped they would see me around the town, we sailed a half-mile or so off the coast and dropped anchor. With the boat now to ourselves, and far from prying eyes, I shed my tiny bathing suit. This was just the signal the guys needed, and they were on me in a flash - the very result I had intended.

As they pulled off their uniforms, I checked them out. Both were in great shape, as I would expect of such outdoorsmen. Paul, the giant, had actually only a medium-sized cock, at least in its half-aroused state. Despite his smaller stature, Sam was actually far better endowed. I smiled, laid down on the cushions on the foredeck, and beckoned for them to join me.

Sam started kissing my forehead, working his way down. Paul started at my feet, working his way up. Their hands roamed everywhere: testing, fondling, squeezing, rubbing. I reached for their now hard cocks and stroked one in each hand. Sam stopped at my breasts, licking and sucking on my sensitive nipples, causing me to moan rather loudly. Paul finally reached by pussy, sliding a couple of fingers into my dripping gash and gently kissing and licking my clit. I was all theirs, lost in their attentions, completely under their control to use as they wished. Fortunately, they seemed eager to please me, for I likely could not have denied them anything at that moment.

Paul mounted me, sliding his cock into me to the hilt on the first thrust. It felt so good to be filled. Sam moved around to my face, and I eagerly sucked his now steel-like enormous prick. As I curled my legs around Paul and urged him on, I wrapped my lips around Sam, and took them both deep inside my willing body. Enjoying this overwhelming stimulation, I came relatively fast and hard. As my pussy clamped down on Paul's dick, I felt it swell within me, and spurt several large loads of cum onto my cervix.

Still rippling from my orgasm, I turned around, pushed Sam onto his back, and impaled myself on his huge cock. Well lubricated with Paul's copious load, he went in easily despite his enormous girth and length. I started to ride him hard, bouncing up and down on his erect member. I wet my fingers with the fluids being squeezed out of my pussy and began rubbing my clit in earnest. I kept my fingers still, but each up-thrust drew them across my screaming clit, and each down-thrust did the same. Doubting that Sam would last that long, given I'd been sucking on his cock already, I was desperate to cum again.

As we both neared orgasm, his cock felt like it got even larger - if such a thing was possible. His girth stretched my pussy to its limit, his long cock provided near constant friction as it plunged in and out of my sopping wet cunt, and I was reaching for the sky. Suddenly, starting in my toes, came a distant but all the same familiar spark that electrified every nerve in my body.

As I was nearing the peak, Sam's thrusts became harder and his cock exploded within me. Given how tightly I was stretched, I felt each spurt travel down his length as the mass itself filled me to overflowing. This was all I needed and I spiraled out of control. Contraction after contraction wracked my pussy, squeezing the essence out of Sam who almost seemed to wince in pain. I collapsed onto his chest as his cock began to slowly deflate.

All this while, Paul had been watching and stroking his once spent cock back to life. He looked like he needed more - and who was I to say no. I sucked him deeply into my mouth, tasting his cum and my juices together. On my knees before him, I gave him a blowjob that I knew he would not soon forget, using every trick in my book.

I licked his head and up and down his shaft. I loosened my throat and took him beyond my gag reflex; breathing through his pubic hairs, I swallowed, squeezing the head of his dick as it filled my throat. As he was obviously nearing his climax, I withdrew him from my mouth and pointed his blood red dick at my breasts. He understood. With his hand now gripping mine, together we brought forth another enormous load that covered my chest, ran down my cleavage, and slowly oozed over my tits and dripped from my nipples. This is one of my favorite ways to finish a guy. With both hands, I rubbed Paul's cum into my chest and, finally, licked my palms clean.

At this point, Sam pointed out the time and that they had to get to port. We gathered ourselves as best as possible and docked only a few minutes late. The dinner party was already waiting. Paul and Sam looked disheveled. I had managed to crawl back into my tiny bathing suit that was now increasingly inappropriate in the cooler evening air. My pussy was still squishing with cum. As Paul's cum dried on my chest, I looked and smelled like sex.

As I disembarked, no one boarding the boat had any illusions what their crew for the evening had just been doing. I smiled as they began to board. Walking back to my hotel, my bathing suit could not absorb the liquid leaking from my vagina. Cum was slowly dripping down my thighs. I scooted through the lobby as quickly as possible to my room. Looking at the clock, I realized it was nearly 7:30. I had to meet Brandon in half an hour! A shower was certainly in order.

I arrived at the lobby 10 minutes late. Despite the rush, I took great care with my appearance. For some reason, it seemed to matter a lot to me. Checking myself in the mirror before I left, I decided I looked gorgeous. Tight dress. Pushup bra that displayed my, um, assets to their fullest. A nice glow on my skin from the day's sunshine. He should be interested, I thought.

Brandon was waiting patiently for me, wearing slacks and a jacket. We took a taxi to a nearby restaurant on the beach, where he had reserved a table overlooking the water and where we could just see the sun setting over the horizon. It was beautiful - and very romantic. A delicious bottle of wine was followed by perfectly prepared seafood, which I ate with gusto.

After a long afternoon in the sun, and the thorough fucking I'd received, I expected to be exhausted. Instead, Brandon's attention was like water on parched soil; I flowered. The conversation flowed easily. After college, Brandon had joined the Marines, serving two terms in Iraq. He did not want to supply details, and I did not push. He enjoyed his job at the real estate development company, not least because it took him to exotic locations to identify potential properties for the firm to buy. He turned out to be several years older than I, very stable, polite, and someone that I warmed to immediately. We talked about our families, our dreams, our expectations. It was as nearly perfect as a date can be.

After a slow, leisurely dinner, which I did not want to end, we decided to walk back to our hotel along the beach. We lingered along the surf, me getting my feet wet in the waves, Brandon cautiously stepping out of them as they rolled to the beach. I took his hand in mine, which he warmly grasped. As we neared the hotel, I drew closer to him, putting my arm through his. He then wrapped his arm around my waist, I did the same to his. As we stepped onto the veranda of the hotel, he leaned down and kissed me tenderly. I melted inside.

Straightening up, he said he had another early morning tomorrow, and then thanked me for a wonderful evening. I was horrified. Despite my full day, I was expecting him to come with me to my room. I certainly did not expect to be left outside the lobby. I guess I pouted more than a little, which he sensed. He apologized, but said he really needed to go.

As he walked away, I noticed his slight limp again. That's it, I declared. He's not perfect. I could never fall for a guy with a limp! Exhaustion then settled over me. Returning to my room, I slept fitfully. What's wrong with me, I wondered? I pulled out all my charms. I sent all the right signals. Or really, what's wrong with him? I thought he liked me. Why didn't he want to spend the night together?

Day Three

I woke in a bit of a funk. After coffee on my balcony, I decided I needed another massage and called down to the spa to see if Dani was available to come to my room this morning. Fortunately, she had just received a cancelation and could come up shortly. My tight muscles needed relief, or so I told myself.

Dani did not disappoint. As before, she set up her table, heated her oils, and began the massage. I relaxed under her excellent hands. Again, as she began working on my front, I began to get aroused. She had to notice. As she worked on my thighs, I started to arch my pelvis, beckoning her to touch me. Finally, she turned her attention to my nether region, which was by now soaked in anticipation. Suddenly, I sat up, took her by the hand, and pulled her to my still unmade bed.