The sun, its warmth, the sound of ocean waves, the sand and the breeze all let me know I was nowhere near home. As I laid out in the heat and let my skin feel alive once again, I kept my eyes closed and thought about how much I needed this vacation. It was overdue and I mentally made a note not to let it happen again. I had let myself get so deep into work and career that I had come close to burning out.
My life at forty was going well by some standards, but it was also a bit of a mess. On the executive career track at the company, my MBA finally paying off, I was putting in long hours and had paid the price. Several prices actually. My marriage had flamed out when I found my husband cheating two years earlier and the divorce was bitter and costly. Making a lot more money than he did turned out to not be such an advantage after all. Paying him alimony was a constant thorn. I had tried to make time for him, but he never could adjust to my success and had taken to playing around with my money, while I was away on business. When he started playing around the neighbourhood, I was taken aside by an irate husband down the street and the jig was up. The thought that my ex was still having a rollicking good time off of my support, was something I just had to let go. It never seemed to let go. Never having time for children as I worked my way up the ladder, was another price I had paid. Well, at least I wasn't paying child support as well.
At forty, I was still a "fine figure of a woman" as my last boyfriend had said. I had managed to maintain my slim figure with my still firm A-cup breasts. I had a conventionally pretty face and kept my hair short but neatly styled. My last boyfriend thought I was more like thirty in appearance, but he also wouldn't put up with a girlfriend who was gone half the time and tired the other half. Why did the men seem to be able to run the world, have a life and still have energy? Because, I thought, they ran the world but the women did the work. At least it seemed that way at the company. All of my business ideas were taken into consideration, passed up and then came back as some guy's idea that I had to implement. It was one of the costs of doing business. I paid the costs. I did try to work out at least twice a week, and always did so when on the road, as it kept me out of the bars and lounges, with their ever present lounge lizards ready to feed. Admittedly, on the road, I had on a few occasions let some guy seduce me, pretending to not know how they played the game. But that was only after the separation. The sex was all right, and on one very special occasion, an older gentleman showed me what a truly skilled lover can do for a woman.
Slow, rhythmic and sultry thrusts, steady and continuous, for what seemed like hours had given me more deep orgasms than I had believed possible. He had played me like I was a fine violin, effortlessly moving me from position to position, his older, poorly muscled body doing what no young lover had ever done for me. His "old man cock", thick and not all that hard, was massaging in me, not unlike a large and soft toy. Occasionally applying more lube, as I couldn't possibly stay wet for that amount of time, he masterfully gave my vagina a sexual feast, complete with hor's deurves, several entrées and dessert. And when he finally shuddered and stiffened, his penis in to the hilt, his face a grimace almost of pain, he came in me and came, until I thought he was faking but it was real. As he finally withdrew his condom covered penis I could see more semen in it than I might normally see in a month. Ever the gentleman, he took care of it himself, discreetly covering it with some tissue, a quick toss in the waste basket and then kissed and caressed, spoke softly of pleasant things and cuddled as we both drifted off to sleep. Where did the men like this hide in my city?
I lay on the beach, my large towel under me, a bottle of water and sunscreen beside me and the sun above. I was in a two piece suit, but appropriate for my age. The older women at the resort, who liked their Wicked Weasels, seemed a bit, well, like they were trolling. It wasn't specifically a "clothing optional" resort, but several women were tanning with their tops off. Apparently no one made a fuss. Maybe tomorrow, I thought. Today, I would just tan and chill. Footsteps in the sand and I came back. I opened my eyes to the glare of the sun and with my sunglasses helping I could see a couple walking by just below my feet. He was very tanned, like a man who lived in the sun. About mid fifties, grey hair, an enormous diamond on one hand flashing in the sun, and not all that fit, flabby actually. The woman was similarly tanned, her skin prematurely aged, and she had several sparklers flashing. She also had a tiny G string bottom, and no top. Her hips looked ridiculously large for her choice of bikini bottom and her large floppy pendulous breasts moved from side to side as she walked. She was not very attractive, even with the diamonds. The man gave me a long and studied look, slowing his gait as he went by. He raised his eye brows a bit and tilted his head. He obviously liked what he saw. I closed my eyes and waited while he walked away, feeling like I was on display. I was, but I didn't appreciate his leer.
I had been at the resort for three days. The first day I was tired from travel and just rested by the pool. The resort nightlife didn't appeal at all that night and I went to sleep early and alone. The second day, rested and ready, I had walked the beach in the morning letting my life slow to the rhythm of the waves. In the afternoon I went horseback riding at the resort stables and took in a guided ocean ride, letting the horse walk and trot in the water until I was soaked and laughing. Riding bareback in the waves, I could feel the power of the horse, its rigid spine working against my labia and clitoris. Without trying to attract attention I purposely let my body rock as the horse trotted through the ocean, and after several minutes felt an orgasm starting. Trying to maintain facial composure I let it take me and the continued motion of the horse under me brought on another, then a third. God, what was I doing? Thankfully the ocean water had already soaked my shorts so at least my gush of fluids was not apparent. The guide gave me a special smile and I realized that he must have noticed. Then I also realized he had probably seen this daily. No wonder the ocean rides were so popular with women. I wondered how many riders of my gender all hot and bothered from the ride had continued to ride with the guide. None of my business, I thought. What happens on vacation...
That evening, I dressed in a casual sun dress, low heeled sandals and went to the nightclub to let my hair down. I danced, checked out the guys and let several bring me a complimentary drink and considered having a casual sex session. Most of the people there were couples but there were also enough singles to make for a marketplace. I enjoyed the posturing, the flirting and the music. Several times I watched as a woman would flash a breast and the flashing got better as the night and the free alcohol progressed. It seemed like everyone there was in a sexy mood, and I felt myself get caught in it. A couple of young women there were kind of playing a game of truth or dare. As the night went on, the dares became more and more risqué. Flashing breasts gave way to serious dirty dancing and flashes of panties. Most of the men were glued to the show, even if some of the women were unhappy that they were. A young man asked me to dance. As soon as we were on the floor, his hands went to my ass and he held me tight to grind his bulging tented pants to my pubic area. With several drinks on board and with the location, I actually ground back. He beamed at me thinking he just might have a score for the night. I wasn't sure so I just let it continue. He had noticed I was by myself and asked me to sit at his table. I thought, why not, it was part of the entertainment. There were several others there, all younger than me and he seemed the only one unattached. We chatted, laughed, danced and drank. The truth or dare show continued and it became obvious that the two young women had removed their panties. They were getting less and less inhibited and were clutching themselves and rubbing each other, laughing and carrying on as if this was routine. The guys at the table were wide eyed and thoroughly enjoying the performance. The girls made a few catty comments, then got into it and got up and did some dirty dancing as well. It all seemed like fun and even I tried a bit of it, giving the guy a quick drop of my sundress top to expose a bra enclosed breast, and giving him an "oops" childlike look. He smiled and danced behind me, rubbing up to my ass and holding one arm around my middle, let the other run up and down my thigh, finally lifting the dress bottom to flash my lacy ice blue panties.
Back at the table I let him put his hand on my knee and wondered how long he would take to move it closer to the object of his affection. It wasn't long. As one of the now very drunk truth or dare girls was stroking her exposed vulva and the other dropped down to give her some quick oral, he moved up my thigh and under the dress, to run his fingers up and down my pussy. I let him, even to the point of putting my own hand down to move aside the panties. He tried to pretend we weren't making out at the table and did reasonably well. With all eyes on the girl-girl oral show, he put a finger to my now very moist vagina and massaged. I held his hand, pushing it to me firmly and just watched the show. As the crowd cheered on the girls, he worked as well as he could and I felt a thrill and a chill go up my spine. His palm was massaging my hardening clit and I was sure that only a few minutes would produce an orgasm. Unfortunately, the oral show ended fairly quickly and both girls just raised their arms and danced around each other. As faces turned back, he quickly moved his hand to my knee. Yes, I was going to get laid tonight and felt very good about it. It was only then that I asked him his name. "Phil," he said.
"Kathy. Pleased to meet you, Phil."
Another drink, a few more dances, each one more sexual than the last and the guy was almost shaking, he was so turned on. "My room or yours?" he asked his voice husky and urgent. "Mine" I answered. I was reasonably sure he had condoms, but I knew I did and my favourite lube was there as well.
He wasn't able to keep his hands off me as we went up to my suite. I knew everyone at the nightclub was well aware of our intentions. So what? I was on vacation. The sex was a disaster. The guy, about mid twenties, not much taller than me, not very fit and with little knowledge of how to pleasure a woman, seemed so hopeless after the older gentleman lover. His idea of oral was to stick his tongue out and shake his head back and forth over my clit. Where did he learn that? He ignored my breasts, didn't pay any attention to kissing or caressing and seemed bent on getting his rocks off and then getting out. His penis was average length I guessed but slim. It felt okay but nothing like the thicker penis that had pleasured me so well. Despite having a rock hard erection, he felt.....inadequate in me. He came quickly, long before I felt much and lay on his back, panting. After a few minutes, during which I felt cheated, he said, "Give me a few minutes and I'll fuck you some more." So romantic, this one, I thought. I realized he wanted me to deal with the condom so I tried to remove it sensually but he just slipped it off and tossed it aside.
"Suck me hard and I'll really fuck you."
'As if' was all I thought, but I got up, went to the bathroom and returned with a warm damp cloth to clean his semen from his penis. Somehow, I just couldn't bring myself to suck it off of him.
I gave him oral, slowly and sensuously, as best I could, hoping that maybe he would learn something. After about ten minutes of this, he seemed impatient. His penis was almost fully erect and he obviously wanted to get back to fucking. I put a second condom on him and he asked me to "assume the position". Knowing what it meant but irritated at his attitude, I did get on all fours and offered him my back way, after quickly applying a bit of lube to my vagina opening. He quickly started thrusting into me, slapping his hips against my cheeks. After about one half of a minute he was bucking at me like a high school kid.
"Fuck, this is good. Fuck, you have an ass!" With that he withdrew and put the head of his penis to my ass and pushed roughly. Damn, but this guy was a jerk! My ass didn't take him of course, and it hurt.
"Stop, not like that", was all I said and turned over. I was okay with anal, but not like this.
I was about to tell him how to do it properly when he said, "I thought all you older women loved it up the ass. What's wrong with you?"
That was it. "Get out, right now." I got up, went to the closet and put on my robe. He was still on the bed.
"Cock teasing bitch," he muttered and got up, put on his pants and glared at me. "Fuck! My first older piece of ass and you turn out to be a fucking cock teasing cunt!" After several more outbursts of crude vindictive he left, leaving the door open. I closed and locked it, leaned back against it and tilted my head back against the door and let my breathing slow. It was absolutely the worst sexual experience I had ever had. I showered, and paying particular attention to washing away any trace of him from my unfulfilled pussy, I just seethed.
"Fucking little shit head" I muttered and got out of the shower. Masturbating was out of the question. I was too angry. I poured a drink from my supply and sat in the easy chair, wearing only the robe, put my feet up and picked up the TV remote.
I turned on the set, went to movies, adult movies and then the selection. It was extensive. I seldom watched porn but it seemed like a release. I picked a title and watched the usual array of porn offerings. Huge tits, amazing cock, blow, fuck and the requisite cream on her face. Gangbang with the girl drenched in cum. Two guys, one girl and the inevitable double entry scene. Two massive cocks, stretching both pussy and ass, the girl moaning in ecstatic pleasure. Two girls, one guy, who fucks like a machine on overdrive. The inevitable girl-girl scene with two women, in make up, serious hair and loads of jewellery, skanky clothes and high heels, who never seem to take off the heels. At least the women seem to be okay at giving each other oral. And finally, the two ended dildo scene with both women having endless orgasms.
Porn made, produced and directed by men, for the male audience. No wonder the guy I had kicked out earlier was so bad.
Two drinks, more porn and I was finally ready to sleep. Almost mechanically I massaged my self to an orgasm and fell asleep. I awoke in the morning with a headache, vague memories of disturbing dreams and a renewed appreciation for decent lovers. Another quick shower, breakfast by the pool and now I was on the beach.
Knowing I was likely to run into the guy who was such a disappointment, I considered how to handle any negative comments. "You're an immature jerk" seemed to work.
In the afternoon, I decided to get out of the resort and explore. The surrounding area was considered safe, if you weren't looking for trouble and didn't stay past sundown. I walked through a market, admiring the locally made crafts. A beautiful wrap caught my eye. I put it on and admired myself in a mirror. Only minor bargaining so as to not look too stupid and it was mine. The older teen girl at the table smiled and said, "It was made for you, Senorita." I smiled back. Instead of putting it in a bag, I decided to wear it as a sash and walked away. Some more looking at jewellery, clothing, leather goods and I was ready to walk back to the resort. To my surprise, the table where I purchased the wrap was now being looked after by an older woman and the younger one was not there. As I walked out of the market, a hand took mine. It was the girl.
"My aunt was pleased at how much you paid, Senorita. She let me go early." She smiled again and I smiled back, touched by her child like innocence. She walked with me and chatted about her aunt, how she worked at the table sometimes and what school was like. She looked to be about late teens but acted younger. She had a child like manner that made me think she might just be handicapped in some way. She was treating me like we were old friends, instead of strangers who just met. I chatted with her, wondering if it was appropriate to be walking her away from her aunt.
"You are a very nice girl, but don't you think you should be getting back to your aunt?"
"No, Senorita, I can play now until I want to go home." She had yet to let go of my hand and I felt like I was walking with a child of eight, not an older teenager.
"You are from the resort, Senorita? I have never been. It is for," she paused, thinking of the word, "from away..."
"Tourists?" I offered.
"Si... you know." She was really not mentally a teenager. That was obvious. "Can you show me the resort?" Her eyes beamed like a child on Christmas morning.
"Don't you think we should ask your aunt? She will worry."
"No, I come back later. She will know." I thought 'what harm then' and we walked the distance to the resort chatting like school girls. She was very pretty, big bright eyes and a wonder about the world I almost hoped would never go away. Her hand was still clutching mine.
"What is your name," I asked.
"Isabella, "she said.
We walked around the resort and her eyes grew bigger. She had obviously never seen swimming pools, manicured lawns, gleaming bright buildings and resort staff in crisp white and red uniforms. "Your room, Senorita, which one is it?"
"Would you like to see it'" I asked, enjoying her banter and happiness.
"Oh...please, yes." And we went to the room, her eyes registering a bit of confusion at the elevator. When the door opened and we were on a different floor, she clapped her hands. I opened my door and we went in, the room immaculate after the housekeeping staff had been through. She walked around, wide eyed at the room with a large bed, comfortable furniture and carpeting. "Senorita, you must be a princess."
"No," I laughed, "just another tourist." There was bottled water on the desk and I opened a bottle and poured her a glass. She took it and sipped hesitantly, then smiled when she recognized water. There were many things here new to her. We continued to chat and I found it hard to picture an older teenager when she was so much younger inside. Her body was slim. Her hips were narrow but not childish. Her breasts were slightly bigger than mine and plainly not surrounded by a bra. They were firm and self-supporting, as if they were just swelling. She was wearing a simple skirt and a tee shirt that was partially covered by a traditional native vest. Her long black hair shone in the sunlight. She really was a beautiful young woman, an older teen going on eight. I wondered what her life would be like.
"Are you hungry at all," I asked.
She looked around and said, "yes, but there is no kitchen."
I gave a little laugh and said," That isn't a problem. We can just call for some food." She looked sceptical but nodded. I got out the room service menu and asked, "How about some dinner." It was about five in the afternoon.
"But what is there here?" she asked. I gave her the menu but it was quickly apparent she couldn't read it.
"How about some pizza?" I asked, thinking that would be a safe bet.
"What is pizza?" was the reply.
I smiled again and said, "You will like it." I called and ordered the pizza, some salad and a bottle of chilled white wine for me and milk for her. When the food arrived she was ecstatic. She liked the pizza and was hungry, eating most of it while I had some salad and sipped the wine.