Discovering Sarah Pt. 01

"Truth is, we damn near live on it when we are here."

She studied me closely and then started walking again.

We stayed on the beach until around 5 o'clock and then headed back to the room. We took turns using the bathroom to shower and change and then had a few cocktails on the balcony until supper time. After we ate, we had a few more cocktails at the bar.

After several rounds, Sarah looked at me and asked, "so you and Joanne have gone to nude beaches?"

I kind of felt guilty about revealing personal details about Joanne to her sister but replied, "yes, every time we come to Jamaica."

She looked at me thoughtfully and said, "what you said earlier, it's not that I'm judging people. It's just that I can't imagine myself doing that. I almost wish I was that brave. If I had a better body, maybe I would."

I told her, "you should never do anything your not comfortable with. But, it really saddens me that you're so insecure. You should be happy with whatever body you have. A woman's body... any woman's body, is a work of art, including yours."

She smiled sadly and said, "Nick sure didn't think so. He pointed out every flaw of every woman he saw; especially me. He constantly reminded me that my butt was too big, and my boobs were too small."

I put my hand on top of hers and said earnestly, "I have news for you, your ex-husband was a dick head. The whole family thoughts so. The only reason he ridiculed you is that he was an insecure little baby man. A guy like that can only feel good about himself by tearing others down. He knew damn well that he was an overachiever by marrying you, and probably was afraid that you would realize it one day. Sarah, you are incredibly beautiful, and you have a great figure."

I'm not sure, but I thought I saw her eyes tear up a bit. "If I'm such a catch, how come I haven't had a date since the divorce?"

I told her, "because you go to work, come home and sit on your couch. Unless the pizza delivery boy is the man of your dreams, you are not likely to meet anybody locked up in your apartment. And if you don't mind me saying so, you come off as a little distant."

She rested her head in her palm, "you're right, I need to make some changes and put myself out there. But it is hard, anyway this week I am going to have some fun!"

I couldn't help but think to myself, I can't believe I'm having this conversation with her. She may have a personality after all.

"Tim?"

I looked at her, "what?"

She smiled and said, "Thanks for the ego boost, and thanks again for bringing me here. It's really beautiful."

Hmm, I thought, maybe there's more to her than I would've guessed.

After drinks, we went back to the room. Sarah went into the bathroom and emerged in her T-shirt and ratty flannel night pants. I shucked off my shorts and shirt and headed towards the bed in my underwear.

"Gosh," she said, "I thought Mr. naked beach man would be sleeping in the nude."

I shook my head and said, "Sorry to disappoint, but I don't want to freak you out."

With that, she pulled the covers back and took the long decorative pillow that had been sitting propped against the headboard and laid it out between us as a sort of protective wall. She chirped a friendly goodnight, and we both fell quickly asleep.

Day 3: "She Got Me Half The Way There" Day Tripper, The Beatles

We woke up the next morning, changed and hit the beach. After lunch, we caught a shuttle to Dunn's River Falls. I have to admit that it was a very enjoyable afternoon. First, the falls are always fun and, at least in my opinion, one of the most beautiful places on earth.

Also, much to my surprise, Sarah had come out of her shell a bit more. She seemed to be in a good mood, and we laughed and talked quite a bit. If you've ever done the falls, you know that you spend a considerable amount of time scrambling up slippery rocks and it is important to help each other along the way. The climb, along with conversation the previous night did much to break down barriers. I couldn't help but think to myself that JoJo was right; this trip was bringing Sarah and me closer. She was definitely getting more comfortable around me, and I was surprised to find that I was starting to enjoy her company.

After we got back from the resort, we had a couple of hours to kill before supper. We planned to clean up and then have a few cocktails before going to the restaurant. We sat out on the balcony and had a couple of rum and Cokes. When Sarah finished hers, she announced that she had to get her wetsuit off and was going to go take her shower. I followed her into the room and turned on the TV. I heard the shower running, and I heard her using the blow dryer. I was stunned when a few minutes later, she walked out of the bathroom in her bra and panties.

I was also pleasantly surprised by her taste in lingerie. I'm not sure why, but I sort of assumed that her underwear was just the typical everyday variety. But the vision that walked out of the bathroom was more like a Victoria's Secret ad. Both her bra and panty were a matching vivid red with black detailing. The bra was obviously a push-up that created some impressive cleavage. The panties, what there were of them, were obviously made of a very lightweight, almost flimsy fabric. The tiny patch of fabric did not so much cling to her as it just hung on her hips. Although not see-through, they left little to the imagination.

The overall effect was mesmerizing. She noticed me taking her in and said, "you've been walking around in your underwear, I guess I can too, right?"

Trying not to appear overly enthusiastic, I said: "sure whatever you're comfortable with."

It was hard not to stare. Her long shapely legs transitioned into the gentle curve of her generous hips. It was obvious Sarah was well-groomed because her panties barely covered her mound and no hair was showing. Her tiny waist led the eye to her breasts, which were practically pouring out of the bra cups. When she walked past, I discovered that her aversion to thong swimsuits did not extend to panties. There in plain site was that plump ass I had scoped out so often. It was round and firm... and perfect.

I get that underwear is really not much different than a bikini, and seeing a woman in underwear should not be a big deal to a grown man; but seeing an attractive woman walking around in lingerie, especially in a bedroom, makes an impression. In this case, that impression was acknowledged by swelling in my shorts. Here was shy little Sarah, casually lounging in her underwear, especially such sexy underwear. To her, it was probably no big deal, to me, it was a very big deal. If I stayed in that room, I was going to embarrass myself, so I headed for the shower.

It took 20 minutes to shower and, shall we say, relieve some tension. When I came out of the bathroom, I expected Sarah would be dressed and ready to go. But I was pleasantly surprised to find her still in her panties and bra, stretched out on the bed watching TV. Lying there, she looked so long, so languid and feminine. To my embarrassment, my dick began to swell again. Standing there in my too-tight underwear she had to notice. I turned away and found my shorts. If she saw my reaction to her, she did not acknowledge it.

Either fortunately or unfortunately, on seeing me, she said: "I'm hungry, let's get dressed and get going."

With that, she jumped off the bed and slipped on a sundress, and off we went to dinner. In my head, one word was repeating over and over... Busted!

Dinner was once again followed by drinks. To my surprise, Sarah visited with several people in the bar. She was coming out of her shell! I suspect some of her newfound social confidence may have been alcohol-fueled. Frankly, we were both more than a little drunk by the time we stumbled back to the room. On the way, we passed one of the pools. It was a beautiful night, and the gorgeously lit water looked inviting. Sarah suggested that we put on our suits and go for a late-night swim. The idea sounded good to me, and so we had a plan.

While Sarah went into the bathroom to put on her swimsuit, I quickly changed in the bedroom. After a few seconds, I heard a loud "fuck!"

"What's wrong?" I inquired.

"I just tore my suit, dammit" was the reply.

She came out of the bathroom in her robe holding the suit.

I asked, "How the hell did you do that?"

She replied, "Da, I'm drunk dammit, and when I tried to step into it I lost my balance. I tried to catch myself, and my foot ripped the crotch out of it. Now, what am I going to do?"

I said, "relax, we can get you another suit tomorrow."

She pouted, "but I wanted to go for a swim tonight."

Smiling, I halfheartedly threw out the suggestion, "we still can."

Sarah thought about this for a second and said, "I am drunk, but I'm not that drunk. I'm not going skinny-dipping with you."

I was encouraged that it took her a few seconds to say no to skinny dipping, even though I had not suggested it. I pointed out," just go in your underwear, it sorta looks like a swimsuit. Besides, I doubt anybody will be there but us."

She didn't say anything, then turned and went back in the bathroom. When she returned in her bathrobe, she announced: "I'm ready, let's go."

When we got down to the pool, I told her that I wanted to get in the hot tub before swimming. She liked the idea, and we walked over to a secluded little spa tub surrounded by plants. I hopped in and noticed that she was hesitating by the edge of the tub. I asked, "what's the problem?"

"I'm not sure how well I'm going to be covered when I get wet."

I told her, "it's just us, and I won't look." With a smile, I added... "much."

Like a little girl she raised on her tiptoes and said 'promise not to tease?"

I solemnly gave my word. She dropped the robe, and happily, I saw she was still in the same red and black lingerie from earlier. She eased her way into the tub. I noticed that when she sat down, she kept a respectable distance between us.

We soaked for about 5 minutes before fate intervened. Another couple made their way to the hot tub and joined us. As soon as they got in the tub, Sarah slid over close to me with a panicked look on her face. I liked the feeling of her body next to me, knowing how nearly naked she was. But I was worried about how she must be feeling; she was trapped in a hot tub practically naked in the presence of strangers.

I whispered, "don't worry about it, you look fine, and besides you'll never see them again."

They introduced themselves as Rich and Connie. They seemed like nice folks, maybe in their mid-50's. She was quite friendly and small talk quickly ensued. Rich was keeping up with the conversation, but obviously, his attention was focused on Sarah. I think he tried his best not to be obvious, but he was constantly trying to catch glimpses of her.

Sarah must've noticed, and apparently she was not as mortified as I thought she would be. After about 10 minutes, she announced that she was getting too hot. To my utter amazement, she stood up and then sat on the edge of the tub. When she stood up, the look on our companions' faces was worth a picture, especially his.

Sarah's panties were practically sheer, and they slid down to the point where they were barely covering the top of her pussy. In fact, a wisp of pubic hair was showing over the top of the panty. Her bra was holding up better, but even it had slipped down enough that a small portion of her left areola was peeking out. Her dainty bra was poorly disguising her very prominent erect nipples.

She adjusted herself as best she could and then brazenly sat on the edge of the pool on full display. She continued the conversation as if nothing was out of the ordinary. I'm sure that our friend had a hard-on, God knows I did.

A few minutes later, Sarah suggested that we hop in the pool and cool off. We said our goodbyes, grabbed our robes, and walked over to the pool. I have no doubt that our new friends got quite a few of Sarah's thong-clad ass as she walked away. Incredibly, she did not bother to put on the robe, and I detected a little extra sway in the hips as she walked.

There were two couples at the pool lounging by the sides chatting. Sarah moved to the opposite end of the pool, tossed her robe aside, and jumped in. We enjoyed the pool together, just silently floating and immersing ourselves in the cool water and warm air. It seemed that Sarah was having a hard time keeping her bottoms on and was continually adjusting them.

After a few minutes, Sarah suggested that we head back to the room. She worked herself to the edge of the pool and pulled herself out. When she came out of the water, her panties slid halfway down her thighs. I was off to one side and could only glimpse a bare butt cheek. However, I am sure that the folks across the pool got quite an eyeful if they were looking. She stood, pulled up her panties, put on her robe, and hurried for the room.

When I caught up, I said, " That must have been a little embarrassing."

She replied with a grin, "Actually it was a little fun. I think you are corrupting me."

I chuckled," I'm pretty sure you're going to be in Rich's fantasy's tonight."

To which she replied, "Just Rich?" The implication did not escape me, and again,, I felt my cock starting to swell.

When we got back to the room, we took turns getting ready for bed. I went first and used the bathroom to change out of my wet suit, dry off, and put on my sleepy time underwear. Sarah followed suit, only this time the funky flannel jammies were replaced by a crop top and panties. She explained that her jammy pants were getting a bit ripe. She climbed into bed and told me to sleep well. I could not help but notice that there was no pillow between us.

After a minute or so, she giggled, "I like Jamaica!"

I thought to myself, I would never have thought I would hear her giggle, I liked it.

Day 4: "When I Saw Her Standing There" the Beatles

When I awoke the next morning, I found myself spooning a warm slim body. My face was buried in her hair, and I found the smell of it intoxicating. During the night, my hand had found its way to her breast, and a morning erection was pressed against her buttocks. Reluctantly, I moved my hand away from her breast and to her tummy. She sighed and stirred.

I apologized, "sorry, I didn't mean to wake you."

She nuzzled a little closer to me and said, "it's okay, I've been awake for a little bit."

As I lay there enjoying the moment, it occurred to me that she did not move my hand when she woke up, nor had she pushed away from my morning wood.

Almost as if she was reading my mind, she said, "it has been a while since someone was holding me when I woke up. It's nice. She snuggled closer, "I don't miss being in a relationship, I don't even miss the sex that much. I do really miss being held in someone's arms. This isn't too weird for you, is it?"

My only reply was to gently stroke her hair for a few seconds and pull her closer.

She wiggled her ass a bit, "ok, maybe I lied, I do miss the sex a little."

And then we drifted back to sleep.

When I woke up again, I was alone in the bed. I heard Sarah moving around in the bathroom. I got up and saw that the door was open, so I pattered in to get a drink of water. She was standing at the sink in a pair of extremely cute yellow underwear and a matching bra, brushing her teeth.

As I downed my water, she spit out her toothpaste, wiped off her mouth, and asked, "did I act too stupid last night? Did I embarrass you?"

I laughed, "are you kidding? Last night was a ball, I enjoyed every second of it." I chuckled and added, "I can tell you for sure that Connie and Rich will never forget you."

She said, "I felt a little slutty."

I shook my head, "don't sweat it."

She cocked her head, "I said I felt slutty, I didn't say I felt bad about it."

We dressed and went to breakfast. Afterward, we went to the resort gift shop to look for a swimsuit. In the best of circumstances, swimsuit shopping is frustrating for women and absolute hell for the men who go with them. In this case, it was also fruitless. The suits were expensive and generally very racy.

After looking at several, she announced that there was not a single suit that she would wear at home, and she did not want to pay $100 for a one-timer. I suggested a duty-free mall near the resort.

"Maybe we could go there later that afternoon and have better luck."

She thanked me for being so patient, and we headed back to the room. It was about two hours until lunch, and she asked what we should do. I told her I would really like to go sit on the beach for a while.

"Well, without a suit I can't go swimming, but there is no reason I can't sit in the sun," she said.

So, I put on my suit, we grabbed our towels and our beach bag and went down to the beach. We camped out in some loungers at the far end and ordered drinks. It was getting hot, so I took off my shirt to get some sun. An hour and three rum runners later, a lady just down from us took off her top.

Sarah looked at her for a long second, then announced: "This is stupid, if she can go topless I can damn well take off my shirt."

And off it came. It was hard to believe that this woman who wore jammies to bed was now laying on a public beach in broad daylight in her bra. Even more surprising is that a few minutes later, off came the shorts as well. The sight of her lying there in some very sexy lingerie for all the world to see was a turn on. There were a few women with a little less on than she, but the idea of her being in her underwear in public was exciting. Seeing any woman in her underwear in public would be exciting, but especially Sarah. It was so out of character, it seemed so erotic because it was so daring for her.

Even more exciting was the fact that once again, her bra was vainly attempting to restrain aroused nipples and her panties had a distinctive wet spot. Obviously, she was turned on by displaying herself, and she was doing it in front of me. I developed a full-fledged erection my swimsuit could not hide.

She looked over at me and said, "this is kind of sexy being exposed like this."

I answered, "I have to admit, you look pretty hot."

She looked at my crotch and said, "are you hard because of that topless woman over there or because of me?"

I put my hands on my lap and replied, "no comment."

"Don't sweat it, it's okay either way."

Later, we ate lunch and went swimsuit shopping at the mall. It actually was a good day for knocking around, and we had fun. Just as importantly, she found a suit that would work; and because I knew that she couldn't afford it, I bought it for her. I was rewarded with a kiss on the cheek.

That night the resort held a special buffet on the beach. They had numerous tables set up each accommodating three couples. After getting our food, we were waved over to the table by Tammy and Mike from the bus. Sitting with them was a couple Tammy introduced as Diane and Darren. She told us that they had recently met them on the au naturel beach.

Diane was nothing short of stunning. She had dark brown eyes and dark hair that cascaded halfway down her back. She had olive skin that gave her an exotic look. Her face was of classic beauty. Although she was sitting, it was obvious that she was tall and well built. I could not help but notice that she had very prominent breasts that had that gravity-defying quality that only augmentation can produce. She and her hubby appeared to be in their mid-30s and from her dress and jewelry they obviously had money. When they said hello, I picked up an accent and asked where they were from. They said they were from San Antonio Texas but had just moved to Chicago. He was an investment banker, and she was an interior designer. I liked them both, and apparently so did Sarah.