Sexy Sister-In-Law

So this happened, but a little background first.

I'm widowed with kids but they're aging up and mostly out of the house. We're extremely close and they remain the center of my universe. We vacation twice a year - once to the beach and once to ski at Christmas. This story occurs during one of our annual beach trips.

Our beach trip this year was back to Turks and I was going to stay for a couple of weeks and our kids were coming for a week due to work/grad school. I typically rent a large, Grace Bay front condo and this year my sister-in-law and her family were also vacationing with us in their own condo but in the same small complex. We remain quite close primarily because she is committed to maintaining a family connection for her kids. She and her kids are younger and her husband could only plan to join us for the week that my kids were there due to work. Her husband, Jamie, and I get along reasonably well. Neither of us are particularly interesting or great at conversation so I find him tedious and boring. I'm sure he would describe me similarly.

I have known my sister-in-law, Jess, for more than 30 years, since she was probably 14. We've always been close in a cautious way since she had a somewhat obvious crush on me when we met. At that point I was a college student, a summer life guard with a deep tan, and somewhat wild. I was easy to like during those days. Her face bears a remarkable likeness to my wife though Jess is slightly taller (maybe 5'5"?) and somewhat athletic. Her hair is long and wild. It looks like it is permed but it isn't. She is an avid/compulsive runner and when she's training for a marathon she is particularly thin and lithe. She has a beautiful wide smile and is a fun-loving and enthusiastic partier, much like her sister and my wife. She is also fun to talk to because she is one of those people who lacks a filter. She's engaging and can be outrageously shocking.

Because I know specifics are important, I'll say her butt looks fantastic in jeans and her breasts are smaller, maybe b-cup at the very most. I've always found her attractive but, again, from a distance. I have no idea what her weight would be. Best guess is 120 or less, but it fluctuates with her training. Her best look is in a bikini. For my part, I'm 6'1", around 200lbs, and very athletic but in a body that suffers from work, worry, and drive. I'm quite well-educated, gainfully and reasonably successfully employed.

On to the story.

We'd been at the beach now for a week and my kids and her husband were flying out to different parts of the US. Jess and her family lived on the east coast and we lived in the Dallas/Fort Worth area. We saw them off and headed back to the condos. As we arrived, Jess asked if I was heading to the beach. I declined and said I was going to play nine holes at Provo golf club, grab an early dinner and turn in early. We wished each other a good day and headed in our own directions.

I arrived back at the condo around 5pm and ordered fish for dinner, turned on ESPN, ate, and read my book while waiting to succumb to sleep. Jess texted me (thanks to wifi or ATT's $10/day international plan) and asked if I wanted a beer. Not wanting to be anti-social I said sure, come on up.

She arrived within the hour and we sat on the large balcony enjoying local beer.

I asked, "How do you like Turks?"

She answered, "It is incredibly beautiful, with great food, and a fantastic beach. The condo is spectacular and the service can't be beat. I love it and would come often if I could afford it!"

"We've always felt the same. It's been a favorite for years but reserved for special occasions or when bonuses are at their peak. I'm sorry Jamie had to head back. He would've enjoyed the course."

Some silence ensued following which Jess said, "I'm glad to have a break from him. We've hit a rough patch... again. We rarely agree on anything, he has no hobbies, and sometimes I run and train just so I can get away from him."

My wife had told me that they could go hot and cold but they'd been married for almost 20 years. I very suddenly felt awkward and extraordinarily uncomfortable. I'm a prototypical introvert. I'm not awesome from an interpersonal standpoint and am rarely prepared to extend a conversation past topical niceties. I knew it was important to respond appropriately and carefully but was momentarily stumped. Finally, I said, "I'm really sorry." Yeah, that's what I said. Holy crap. Did that just come out of my mouth. I should add more. No, maybe that's enough.

Finally, Jess laughed and said, "Well, I knew you'd struggle with that one."

"I'm sure it will get better" and then I nervously laughed asked, "Have you talked to Jamie?" Where do I get this stuff? I need to watch more Oprah or something.

"Sure, I've talked to him. He's useless, uninterested, and doesn't take me seriously. One of us needs a wake up call."

"Maybe you could try counseling?" I'm amazing at this. My confidence is growing with this font of emotional intelligence spewing from my pie hole. Holy crap. Kill me.

"I've suggested it," Jess said. He laughed at me and said, "No freaking way, but you can go."

"Maybe that's a good idea?"

"Yeah, I tried it," Jess said, "and it was one-sided and difficult to solve without a partner to solve with. I don't think I want a divorce but an extended vacation wouldn't be out of the question."

"Trial separation? Maybe that's his wake up call."

"Yeah, maybe."

By this time we were both struggling and it was getting late (for me). She said she was going to try to satisfy herself and get some sleep. I was appropriately shocked and embarrassed and chose to ignore her comment.

We agreed to meet for breakfast at the local pastry shop with the kids and then head back to the beach for the morning. The normal schedule had us at the pool in the afternoon.

Jess, her two girls, and I met the next day around 9am and enjoyed breakfast outside. It was going to be another beautiful day. We headed back to the condo, through the "portal" and out to the beach. Gathered chairs and began to settle in for the morning. This is when there was a change.

Jess took off her beach cover up with her back to me. This was not a bikini I had seen before and I was dumbstruck as usual.

Now, it wasn't a thong or grossly inappropriate, but, my goodness, it was awfully close. It was one of those bikinis that pull pretty far into your butt cheeks but still has enough material to not be a thong. For sure she had not worn that prior to this day. It was a medium orange color that looks great on a tan and when she turned around she for sure caught me staring before I looked down or away.

The second thing I noticed about the bikini as I stealthily (only from my perspective I assume) studied her in her prone position throughout the morning was that it seemed thinner than normal. It wasn't translucent or anything, but don't most women's bathing suits have pads and such to hide stuff? It wasn't cold outside by any measure (it's almost always low 80's and sunny in Turks) but I was definitely seeing her right nipple. The other one appeared to be depressed.

Obviously I was enthralled because Jess said, "Enjoying the view?"

"Huh?" I stuttered while I tried to come up with a reason for staring at her.

She said, "It's such a beautiful day."

"Oh, yeah, it is." I was so relieved. I wasn't caught. I resolved to keep my mind out of the gutter.

"Talked to Jamie this morning," Jess said.

"Great. Hope it went well." My witty banter is improving, I thought.

"Bought the same, really. I'm thinking of having an affair."

"WHAT THE FUCK?" Oops, I thought.

Jess laughed hysterically, and said, "That was fun."

"Are you serious?"

"I don't know, but maybe. There's this guy I see at our swim-tennis club that I fantasize about."

Crap, I'm uncomfortable again. "Single? Married? Have you guys... done anything?"

"Oh, no, nothing like that. Can't be sure he's interested but I'd sure like to find out."

I blurt, "Well, it sure looks like you've got all the equipment you need to figure that out!" I don't ever say things like this. This is ridiculous. I need to play more golf.

Jess laughs and looks straight at me from her prone position and says, "so you like my new bathing suit?"

"Uh, yeah, it's great. Have you had it long?" I'm a regular James Bond.

"Yeah, but Jamie doesn't think I should wear it. Says it's too revealing."

Well, how the hell do you appropriately respond to that. So I said, "huh."

"What do you think?" Jess asked.

"Well, um, it definitely more revealing than your other ones and it would capture your love-interest's attention. Pretty sure you're getting a fair amount of interest around here."

"Something to think about. I've been trying to figure out how to measure his attention. Any input on that?"

"Capturing his interest?"

"Yeah, sure."

"Hm, well, I'm pretty certain that there is a model for that and as a rule I find men to be really predictable. Men have been groping you in really specific ways since you were probably 16, right?"

"Maybe a little earlier than that but it'd be fun to enjoy an honest perspective."

"Well, seriously Jess, this is not that hard to figure out. Men are shockingly visual and tactile. Women are more emotionally connected. Please don't get your dander up. It's just an observation. I feel like I'm just giving voice to DNA. Don't hate the player, hate the game," I laughed nervously.

Now Jess had lost her tongue. She was sitting thoughtfully while I grew uncomfortable. It seemed she liked to make me/men uncomfortable. Thankfully, she finally added, "A lot there to react to, and it was as interesting as I had hoped."

Was I supposed to say something? I had nothing to say. I felt like I had used up all of my words for the day. I was exhausted and was starting to feel a bit roasted by the sun. I told Jess I was going to retreat to the pool and bar for lunch and beyond. She said she'd join later. I was relieved to have that behind me but it was not to last long.

True to her word, Jess plopped down about an hour later in the chaise next to me. Her kids happily splashing in the pool and hot tub.

Without much preamble she blurted, "So... first, what do mean by 'visual' and 'tactile'?

I was not prepared for this and remained somewhat spent and uncomfortable in plotting her affair. Despite that, or perhaps due to it, I forged ahead with more bluntness and detail than I would typically employ with the hope that it would somehow put her off her game. "Well, I think evidence would say that men like to see and touch, and they like it a lot. I don't have any quantitative analysis but there has to be some reason that 'gentlemen's clubs' outnumber the same for women by multiple orders of magnitude, right? I'm not saying that women don't like that but I think in a Maslow type hierarchy, it might be subtly less than men. Or, it might be significant. I don't know. But I know that women can easily attract men visually."

Jess interrupted, "But you didn't say anything about 'tactile'?"

"Oh, right. Well, I'm not sure what to say about that."

Jess asked, "Be direct, open, shocking."

Not my specialty, but again I plowed forward. "Jess, it can't possibly come as a shock to you that men have some base, animal need to grope toward specific parts and they find it surprisingly satisfying to reach those goals. I know we've both experienced it. I think women could easily use that in a motivating way."

"I think you're right," Jess replied thoughtfully.

Not something I'm accustomed to hearing outside of an office and I found it satisfying so I continued with more confidence. "Don't you think if you showed off to your new interest that you could reasonably gauge his willingness to pursue you?"

"Well, yesssssss, but how do I show off?"

"In theory it should be easy. From a practical perspective it may be more difficult. I'll assume he sees you at your pool and therefore in a bikini. That's a pretty good start."

"Yeah, he's seen me like that, but how do I get him more interested?"

For the first time Jess seems mildly self-conscious. "More is more, Jess, and that applies to Jamie as well."

"Huh? What do you mean?" Jess asked with a confused but very interested look.

"Since we're only working with visual right now I can only say seeing more or as much as humanly possible is motivating and helpful to you in measuring or growing interest."

Jess adds, "Jamie has pretty much seen it all, I'd think. How does that help him?"

Now I'm uncomfortable but Jess seems energized. "Ok, have you satisfied yourself in front of him?"

Finally, Jess is dumbstruck, bright pink and it isn't the sun. So I laugh.

She says, "No, that hasn't happened and I'm not sure I could."

"I guarantee he'd enjoy it."

"Voice of experience?"

"Oh, well, no, unfortunately. Voice of male DNA again."

"Ok, then. What about the guy at the pool?"

"C'mon, Jess. You're creative. You figure it out."

"I'm sure I will but this is fun for me."

"I see that. Ok, then. How about your wear that bathing suit to your pool. It shows off more than, uh, normal."

"I'd be a pariah to the other moms who happen to be my friends. This thing is barely there."

"Your goals seem to be in conflict."

"Yes, they do," she says resignedly. "I'm going to take the girls in for some quiet time. Dinner tonight?"

"Sounds good. See you around 6."

I was so relieved to have that behind me. I thought dinner would be safe with the kids and we could all relax. I headed back to the condo and took a nap. I'd like to say that I wasn't thinking of Jess in her bikini but that wouldn't have been true. I couldn't help but to wonder if I'd actually seen her nipple. I'd also been trying to look lower in that attractive netherworld of mystery. There wasn't anything there to see but a slight bulge but I'd wanted to imagine more. I'd been discreet in staring at her, but it was hard to know if she'd noticed. I'm hopelessly awkward.

Six rolled around pretty quickly and I dressed in typical dad casual. Ratty cargo shorts and a t shirt. Practically a uniform for me.

Jess and her kids showed up out front and perfectly on time. I hate when people are late. Her girls are amazing little people. They're well behaved, sweet, and incredibly smart. They were dressed like me. Jess was not. She had on a t-shirt like dress that dropped to mid-thigh. It was a very light pinkish color, thin, and tight in the best/worst places. There was absolutely no way that she had on any underwear. I stared. She couldn't have missed it and I think she was enjoying it. It was breezy and cooler after a hot day. Why did I only see her right nipple? Not important but this is what I was thinking about.

We had a great seafood dinner at a place that was within pretty easy walking distance. The company was as good as the food and her kids were hilarious in the way that only kids can be. We stopped for ice cream on the way back and retired to our respective condos by 9pm. Exhausted I face-planted in the bed and didn't wake up until almost 7.

I had missed a text from her the previous night. She asked if I wanted have a beer and walk on the beach. I was mildly happy to have missed the text. I texted back and apologized for sacking out early. Told her I was heading for breakfast at the local café around 8:30.

To my surprise, they were there and looked ready for the beach. I greeted everyone and sat down, apologized again and said, "What's the plan?"

Jess said, "More of the same, thankfully." There didn't seem to be any awkwardness and Jess was pretty happy so we ate and walked back to the beach, situated ourselves, and... wait, Jess had another of those bathing suits. This one was white.

Jess again lays down and promptly launches. "Talked to the idiot."

"OMG, Jess, it can't be that bad."

"It probably isn't. Just felt appropriate. So, what should I do to attract Mr. Wonderful?"

I'm already exhausted. "Reality and history says he isn't."

"But tell me with brutal honesty and without fear of reprisal, what could I do if I wore this suit, which I already see you like, to take it up a notch or two?"

I swear I could still see her right nipple which only made me more interested in seeing her left. I wasn't particularly willing to be more insightful, so I said so. "Jess, I'm really not sure you can be more revealing than that."

"But if I could, what would it be?"

It was clear, because she wasn't trying to hide it, that she was planning to enjoy the day and be even less delicate, if that were possible. It also felt like she was willing to test her own resolve. I resolved to employ the same tactic. I sat up and faced her and studied her as if she were in a petri dish. Her skin was brown. Her suit was white. I felt like I should be able to see more with the contrast but I couldn't despite my best efforts. Her legs were long and the slight bulge between her legs was really impossible to ignore. I found myself thinking it should reveal more.

"Enjoying yourself?"

"Just trying to satisfy you, Jess."

"As you said, shouldn't be that hard, and it seems more like you're satisfying yourself." She said this with a bit of a bite and smirk that startled me from my reverie.

"Well, what can you do? Let's see. The bathing suit is all anyone could ask for. It's really more about what you do with it, then, isn't it?"

"What should I do with it?" She asked with a challenge.

"More is more, you agree right?"

"I don't have an alternate theory, so I guess I do."

I forged ahead, "Why don't you pull your bathing suit into your lips? That should generate a reaction."

"WHAT?" She exclaimed! "Are you talking about my... well my, those, I mean down there... what?"

Finally, I had won. Jess was all but panting with surprise and frustration and perhaps just a touch of embarrassment. "More is more, right?"

Jess was flabbergasted and without response, so I continued, "Don't you think that would capture his imagination?" I was a little concerned that I had gone too far at this point. I was still sitting above her and staring. Her nipple (singular) was mildly at attention but I was more interested in her lips. She was clearly a little agitated but not trying to cover herself.

Jess was calming herself, but still surprised. She replied, "I'm not sure how to respond to that. That's pretty out there, right? I mean, how could I do that? Do people do that? I wouldn't want anyone else to see that? Do guys like that? What the heck?"

Jess, guys like everything. Despite your sensibility's guys want to see girls with their ankles behind their ears. I know it might be shocking or distressing to hear out loud, but it remains a fact and I'm still convinced, without research or analysis, that it is just a guy thing that cannot be changed. So... yes, I think it would get a reaction, or maybe two, and that might get you guys started.

"I'm not sure I could do that." Jess says.

"Maybe not, but now two data points make a trend."

"Huh?"

"You said you can't do that for your husband or Mr. Right, so your reluctance may be the only thing holding you back from either."

"Well, thanks, Dr. Ruth."

"No problem," I lay back and put my hat over my face to enjoy the sun. Jess sighs and turns over signaling the end of our exchange. I put it behind me and hope we're not damaged by our friendly fun.

Jess jabs me awake some time later. It's getting toward lunch and she says, "I have more questions."

"Of course you do."

"So, his reaction?"

"What?"

"You said doing THAT THING would generate a reaction, or two. What are they?"

"So do you mean what will happen if you do that?"

"Yes, of course I want to know how he'll react."

"I need to think about that. You mean like right then and there?"