Discovering Sarah Pt. 01

But this was not climax, this was prelude. I gently started licking her outer lips, then probing her hot wet vault with my tongue. Soon I moved to lightly flick the tip of my tongue against her clit so as not to overstimulate her. I inserted two, then three fingers and curled my index finger to rub her G spot. I slowly brought her back to the precipice.

I felt her pussy tighten again, and again she began moaning, "Timmy, oh God I love you, make me cum, please make me come baby."

And, cum she did. JoJo's clitoral orgasms are usually brief and intense when I get her via the g-spot; she has what she calls 'rolling organisms." Not quite as intense but protracted and often multiple ones.

Unlike some women, she does not squirt, but when she comes hard, she floods, releasing a surprising amount of honey. I was rewarded with a sweet musky explosion that covered my face and ran down her crack to the bed.

I rolled off of her to catch my breath. But no sooner had I done so that I felt her warm mouth engulfing my cock. I looked down and saw those beautiful brown eyes staring at me lovingly. She took her mouth off of me and said, "do you like the idea of eating Sarah's pussy? Would you like her to suck your dick like I am now? If she saw this beautiful hunk of meat, she would want to put it in her mouth. She would want you to ram it in her. She would ride you until she came and came."

She then engulfed my cock again. Between the expert work of her tongue, and the images she put in my head; my load exploded down her throat within just a few minutes.

With an evil grin, she said, "my my, it seems that my big boy gets a little excited thinking about my baby sister."

"From the sound of it, I'm not the only one," I replied.

She then gave me a big kiss, rolled over, and said "Don't try to embarrass me,"

Soon she was asleep.

I laid awake with so many thoughts flashing through my mind. What the hell was that?

Is she giving me permission to play with Sarah?

Is she messing with my head to get me warmed up to the idea of taking Sarah with me?

Is she having erotic fantasies about her sister?"

One thing was for sure, I was suddenly more intrigued with the idea of a vacation with Sarah.

Joanne called Sarah a few days later and had her come over to the house. We made our generous offer, and true to form, Sarah's response was underwhelming.

She thought about it for a few minutes and said, "yeah, I guess that it would be cool."

Joanne made it clear to her that she would be sharing a room with me and wanted to know if she was comfortable with that.

Again, she thought a few seconds and said, "yeah, that'll be weird, but we can make it work." She then smiled and said, "I've always wanted to go to the Caribbean. This will be fun, although going with Tim wouldn't exactly be my first choice. But, what the hell."

What she did not say was, "thank you."

I said, "yay, I'm thrilled too!"

If Sarah got the sarcasm, she did not show it. Jo did though, and I got the look.

The three of us spent the rest of the evening going over the trip itinerary and stressing to Sarah what to pack, what she was not allowed to take through security, and of course, things to do while we were there. I stressed the importance of not overpacking.

"It is way easier to get through the airport and customs without check bags. You won't need a lot of clothes, so you should be able to pack everything you need into a personal bag and a carry-on."

Sarah smirked, "I won't need a lot of clothes, huh, perv boy? Are you going to try to get me to go native?"

Embarrassed, I said, "I meant that the resort is casual, shorts and T-shirts are good for almost everywhere we will go. You might need just one or two nicer outfits."

A long second passed, and then both women broke out laughing. Apparently, Jo had briefed Sarah on the resort's nude beaches. Not for the last time, I thought to myself, this is going to be a long trip.

Day 1. "The long and winding road" the Beatles

Because we had a 6 AM flight and lived 2 ½ hours from the airport, I booked a room at a hotel offering free long-term parking. The plan was to drive to the hotel the day before the flight, turn in early and be at the airport by 4:30 or 5 AM.

During the time between our invitation for Sarah to join me in Jamaica, and the day that we were to leave, she repeatedly made it clear that she thought a 6 AM departure time was ridiculous. I had explained that it gave us a nonstop flight and would get us to the resort by early afternoon. My rationale did not impress her, and she groused about it in a couple of texts to me. The upside was that I made her text list!

Departure day came, and Sarah met me at the house. We threw our bags in the car, and I was happy to see that she took our advice; she had only brought a small backpack and a carry on roller bag.

When we were ready to leave, Joanne gave me a big hug and a nice kiss, "have fun, and don't do anything I wouldn't do."

"I don't know, I have seen you do some pretty naughty things," I said.

She gave me a more passionate kiss and said, "when you get home, you'll see me do some more naughty things!"

Sarah chirped in, "okay, let's not get gross."

Our car trip consisted of 2 ½ hours of me trying to start conversations which quickly fizzled out, while Sarah sent out a constant stream of texts, tweets, and snap chats. We got to the hotel around 4 o'clock and checked in. The desk clerk confirmed my reservation for a standard room with a king-size bed and 8 days parking.

On hearing this, Sarah said, "Hold on, we need separate rooms."

I told her that I made the reservation before Jo had canceled.

The clerk said that there were rooms available and we could get one for one hundred forty dollars.

I told Sarah, "if you want to spring for a separate room, that's fine, it won't hurt my feelings."

She frowned, "I was kind of hoping you'd pay for it, but if not, can we at least get separate beds?"

The clerk assured us that rooms with separate beds were available. On the way to the room, I couldn't help but think, She is going to be pissed when we get the resort and realizes that separate beds are not an option. What have I got myself into?

Once in the room we dropped our bags, and I suggested that we should grab something to eat around 6 o'clock and try to be in bed by 8 or 9 at the latest; as we had to get up by at least 3:30 AM to get the shuttle over to the airport.

She informed me, "unlike you senior citizens, I don't go to bed until midnight. I Don't think I can get any sleep going to bed that early."

Slightly annoyed, I replied, "Suit yourself, but tomorrow is going to be a grind, and 3:30 in the morning comes fast."

With a grumble, she agreed. After supper, Sarah announced that she was going to grab a shower. With that, she disappeared into the bathroom. Just then, my phone chirped.

From JoJo: "how's it going?"

From Tim: "Argh"

From JoJo: "Be nice... what's she doing now?"

From Tim: "shower...getting ready 4 bed."

From JoJo: "ooh la la"

From Tim: "cool off... separate beds.. luv you."

From JoJo: "give her a chance. you'll have fun, I promise... luv you 2... goodnight."

From Tim; "Goodnight,"

I have to admit the "ooh la la" started the wheels turning. I began to wonder what Sarah's bedroom attire would be. I imagined her coming out of the bathroom in a little nighty, or maybe her underwear, or maybe underwear and T-shirt. Maybe I would hit the jackpot, and she would come out in nothing but a towel.

I was inwardly embarrassed by these thoughts, but after all, she is an attractive woman, and I am a guy; which means that I am a horn dog. I reminded myself no matter what she was wearing, not to stare and keep my mouth shut. In other words, enjoy the show but play it cool.

As it turned out, playing it cool was pretty easy. Sarah came out of the bathroom wearing a ratty T-shirt and even rattier flannel lounge pants. I guess you could say she was kind of sexy if you're into that I don't give a shit homeless look. My disappointment quickly evaporated when other thoughts intruded into my head. I came to the realization that I had a problem.

You see, I don't wear pajamas at home, and it did not occur to me to pack any. I looked at Sarah and said, "I'm going to grab a shower too."

She flicked on the TV, "It's all yours."

"Here's the thing," I said "Jo and I don't wear pajamas and it didn't occur to me to pack any. Are you going to be weirded out by my sleeping in my underwear?"

She cocked an eyebrow, and chuckled." I think I can handle seeing you in your boxers." Then she added, "if they are tighty whities though, I am so going to barf."

This is when two more realizations hit me. First, I don't wear boxers, and tighty whities would have been a blessing. A few years ago, Jo had talked me into wearing long-legged athletic briefs made out of that shiny material that supposedly wicks moisture. If you're familiar with these you know they fit skin tight and leave very little to the imagination in covering your package. The truth of the matter was that Sarah was going to get a pretty accurate view of my junk.

Just as troubling was problem number two. Because of the nude beach thing, and the fact I go commando allot, I don't bring a lot of underwear while on vacation. The truth of the matter is I only packed 4 pairs. Somehow, I was going to have to make those few pair work nine days as both underwear and now sleepwear.

The irony of the situation did not escape me. A few minutes earlier, I was secretly letching over the idea of Sarah prancing around in her panties, but as it turned out, she was fully dressed, and I was the one going to do the prancing. Such is karma.

Again, I thought this is going to be a long vacation.

I took my shower, dried myself off, and put my underwear back on. By the way, there is no worse feeling in the world than putting on used underwear after a shower. I looked at myself in the mirror, and there was my bulge prominently silhouetted in detail. (well, bulge may have been a generous word.) The thought of Sarah seeing me like this was a little unnerving, but also a little bit exciting.

Let her look, she might just like the view, I thought, and with that idea, Mr. happy started to swell a bit. Then panic set in.

Crap, I thought, all I need is for her to see me walk out with a chubby. The embarrassment of that thought took some of the enthusiasm out of Mr. Happy.

As I prepared to leave the sanctuary of the bathroom and strut my stuff for Sarah, I thought, this is weird, I don't believe I am doing this.

By the time I walked out of the bathroom, I was only half aroused, which actually worked in my favor! As my bulge and I walked out in my suddenly uncomfortable underwear, I caught Sarah sneaking more than one peak.

"Well," I thought," that's kind of interesting."

As I got into bed, I heard, "Hey Tim, cute butt!"

"Shut up," I said, and I turned off the light, and we tried to get some sleep.

Day 2. "A Hard Day's Night" The Beatles

Anyone who has flown to Jamaica knows that it can be a long and grueling day. We woke up at 3:45 AM and took turns getting dressed in the bathroom. We then hustled our way down to the lobby and on to the shuttle. The trip went smooth enough, but as always there was the grind of getting through TSA lines, and then sitting on your ass for an hour and a half waiting to get on the plane. Then there is the joy of a four- hour flight in a stuffy, overcrowded plane. On landing in Jamaica, there is the long walk to immigration then standing in line for an hour. After immigration, you get to stand in line for another hour waiting for customs.

Sarah was tired and so sullen and quiet. By the time we made it into the departure terminal, we were both wrung out and hungry. I was not looking forward to a two-hour bus ride. But I reassured Sarah that the ride to the resort would have a lot to see. Although she was exhausted and obviously cranky, she did perk up when we got into the departure terminal, and she got her first feel of the warm tropical air. It also helped that we got some snacks and a couple of beers. One of the first new discoveries I made about her was that Sarah liked her drinks. She quickly pounded down to glasses of Red Stripe. It was the first discovery, it would not be the last.

On the bus ride to the resort, we met Mike and Tammy. They were a young couple, likely close to Sarah's age, from Wisconsin. Mike seemed like a nice enough guy but was pretty quiet. Tammy, on the other hand, was one of those people who never met a stranger. She immediately struck up a conversation with Sarah and me and pretty much talked from Montego Bay to Ocho Rios. Tammy explained that this was their second trip to the resort, and they just loved it. She then went on to give us the lowdown on the resort, and what to do and see. I did not have the heart to tell her I had been there several times before.

At one point, she asked if we were going to try the nude beach. With just a touch of dismissiveness, Sarah said she didn't think so. Tammy excitedly explained that the nude beach was the highlight of their first trip. They'd worked up the nerve to try it last year and absolutely loved it.

Sarah, who typically has little to say about anything, volunteered that she couldn't imagine having the guts to try that.

Tammy said, "you really should give it a shot. I was scared too, it took us five days to finally work up the nerve. I really regret waiting that long. You really should try it on your first day. If you don't like it fine, but you will."

Tammy then assured her with all the passion of a newborn nudist, that it was wonderful and so liberating.

She then tried to relieve Sarah's obvious apprehension, " it's like jumping into a chilly pool. The fear is worse than the reality. If you just jump in you find out it's great. Within 15 minutes, I felt so sexy and free!"

Sarah replied, "I think I'll have to take your word for it."

With that, Tammy changed the subject. "If you don't mind me saying so, I would not have guessed that you 2 were a couple. Are you married?"

Before I could answer, Sarah volunteered, "no, we're not married, we just work together. He's my boss, and he offered to take me on this trip."

With a confused look on her face that slowly morphed into surprise then disapproval, Tammy said, "oh that's cool."

She then promptly turned around and started talking to Mike.

I leaned into Sarah and whispered, "what was that bullshit about?"

She chuckled, "I thought it sounded weird to say that we were going on a vacation as brother-in-law and sister-in-law."

I shook my head, "so you thought it would sound better for me to be a dirty old man who was into sexually harassing his employees."

She chuckled again, "yeah, that sounds about right. And besides, it shut her up, didn't it?"

I asked, "so do you think we will run into Tammy on the naked beach?"

"Dream on boss," was the reply.

We finally made it to the hotel and checked in. During check-in, Sarah asked, "do you have rooms with two queen beds?"

The desk clerk laughed, "no my lady, this is a place for romance. Did you and your man have a bit of a fight on the way here?"

Sarah replied, "no, it's all right."

"Well then my dear, I suggest you makeup and enjoy our hospitality!"

"Thanks," she said, but there was definitely a pensive look on her face.

When we got into the room, she looked around and then looked out the windows. The views were breathtaking, and the room was beautiful.

She looked at me with a huge grin on her and face said, "Wow, this is awesome."

I was happy to see her so animated and replied, "I told you that you would love it."

Then she frowned as she looked at the bed. "It's going to be weird sharing a bed, I wasn't ready for that."

Trying to be funny, I said: "Just keep your hands to yourself, and we'll be fine."

It was about 1:30, so I suggested that maybe we should grab something to eat and maybe take a tour of the resort.

Sarah replied, "I'm all for getting something to eat, but I am too tired to tour anything right now. How about we just go crash on the beach this afternoon."

We had a great lunch at the buffet and went back to the room to change into our suits. As expected Sarah went into the bathroom to change. As I waited for her, I wondered what kind of swimsuit she would come out with. A lot of women will wear an extra daring suit when they are on vacation under the assumption that they are among strangers. But, since I was there, I expected Sarah to wear a normal bikini. I was surprised when she came out of the bathroom. Here was a very shapely young woman wearing a very modest one-piece swimsuit.

I laughed, "did you borrow your aunt's swimsuit for vacation?"

With hands on hips, she defensively retorted, "don't give me any shit, I use this suit when I swim at the YMCA. It's the only one I own."

I put my hands up in a defensive posture and said, "No, no, it's all good. Let's go to the beach, Mildred."

My charming wit earned me a scowl.

We packed a beach bag with sunblock and towels and walked down to the beach where we found a couple of open lounge chairs. We lazed around for about 40 minutes and 3 mojitos each, then decided to take a walk on the beach. During our walk, we passed people of all shapes and sizes. We saw modest (older)women in one-piece swimsuits and many women in various bikinis. Happily, I noticed more than a few extremely tiny bikinis and even some micro thongs.

As we passed a particularly daring woman, Sarah said: "I would never have the guts to wear something like that."

"Why," I asked.

"First, I'd be afraid of what people would think. Secondly, I don't have the body to pull it off."

I looked at her and said, "I don't really think she cares what people think, and why should she? And secondly, don't sell yourself short. You are a bit of a hottie, and you would look pretty good in almost anything you wore."

She gave me a funny look, and I immediately regretted the comment.

After an awkward silence, she punched my arm, "so you really think I'm a hottie?"

I smiled and said nothing. As we got to the far end of the beach, we came across a clutch of braver sun worshipers. A few men were wearing Speedo's, and several of the women were topless. In fact, one woman was walking out of the ocean wearing nothing but an incredibly tiny bikini bottom that looked more like shoelaces. Sarah frowned and turned on her heel to head back the other direction.

She muttered, "I thought the nude beach was on the other side of the resort, what the hell are they trying to prove."

I'm not sure why, but her comment bothered me. I should've let it pass, but I didn't.

I said, "The nude beach is full-on naked only. This is the regular beach. Besides, they're not trying to prove anything, in fact, I don't think they really give a shit what we think. They feel good about their body, and they're comfortable in their own skin. They are enjoying themselves, why should we care what they do."

I added, "Don't hate on them just because they are braver than you."

Sarah looked at me defensively and said, "I don't see you wearing a Speedo." I replied, "I think they're goofy looking. I'd be more likely to just go naked."

Sarah laughed and said, "yeah, like you would go naked on the beach."

I smiled back and said, "would, and have."

With a look of shock on her face, she exclaimed, "you've been on a nude beach? What did Jo think of that?"

"She was there too," I said.

Sarah just shook her head and muttered, "I'll be damned. Jo told me there was a nude beach, she didn't say you tried it."