Caribbean Surprise

The inevitable "empty nest" -- that phenomenon in which parents experience feelings of sadness and loss when the last child leaves home. Its timing is usually known in advance and can be prepared for; like marriage and fatherhood and other life changes, though, you really don't know what it will be like until it happens.

I imagined the empty nest period, beginning around 2012, to be one of renewal for my wife, Susan, and I. We'd be free of high school events and homework and relationships, and could refocus on our health, fun activities, and relationships with friends. And we could fire up our sex life and even take it to higher and deeper levels.

Susan saw it differently. She was sad and at a loss without the last of three kids around to engage with. For the first year after our final kid left, we had sex maybe three times. She sat in her recliner and watched football and NASCAR endlessly on Sundays, never changing from pajamas. Her drinking increased, as did her waistline. Her reply to anyone who asked was that she was 'waiting to be a grandma.' None of the kids were even married yet.

Over these next five years several things happened: deaths of parents, a move to another city. Employment issues and thus money issues. Arguments, ignoring. Counseling, and ultimately divorce. More deaths of elderly relatives and other family issues. The post-empty nest period had gone not at all as I imagined, and in the summer of 2017 I decided to make a move. I left work as a kind of sabbatical, researched and bought a fifth wheel recreational vehicle by Thanksgiving, and hit the road for a few years of solo travel the following February.

Right away I experienced hours alone while driving across the country. There were days when I wouldn't talk to anyone, sometimes nearly a week straight. Stimulation while driving ranged from classic rock satellite radio, Audible books, and simply silence. The time allowed me to sort out some of my skeletons, including anger from my recent divorce and a traumatic issue with one of my sons. I wasn't running away, per se, but I did need to get away and do some heavy thinking about how my life would progress.

I'd had a girlfriend right up to the point of buying the RV. She wasn't thrilled with my upcoming lifestyle and broke it off, although after hearing later about the places I'd gone to and the hikes, tours, and other activities, she was quite remiss in her decision.

You might think, as I thought, there would be exciting sexual activities on the road. Lonely waitresses, fellow travelers. Strippers in dingy clubs, hot pickups in bars. Adult theaters, glory holes. Always careful about my safety, those moments didn't happen. Instead, I jerked off to those situations that I saw from afar, fantasizing how they would transpire and typing some out for future Literotica submissions. It was a lonely but good life, and I knew I'd have a real relationship again soon enough.

Here's one of those situations -- real in structure, embellished for fun, and recalled many times for the memory and self-pleasure.

After six months of solo RV road life and a crossing of the Lower 48, I headed back to California for repairs and to visit family and friends. A few months earlier I'd been in contact with Robert, a former work friend also in his 50s, who invited me to accompany him and his wife, Jenny, and 12-year-old daughter, Bobbi, on a family vacation to Puerto Rico in July 2018.

I was thrilled to go, not just because of the location where I've never been, but because I'd be around Jenny every day for over a week -- I found her extraordinarily beautiful, youthful, sexy, and smart. Early 50s, brunette, athletic. Medium breasts, maybe size 34 or 36. Big eyes and a smile that went on for days. Robert, on the other hand, is overweight, smokes heavily, drinks nightly to drunkenness, and continues to have hip and knee problems. He tells me ahead of time that he's glad I'm going so I can help take care of the girls and ensure they have a good time. I tell him beforehand that he can count on me!

With my RV in-work at the dealer, we fly out of San Francisco and arrive in San Juan without incident. For the first half of the ten-day trip, we stay around our luxury hotel in the Condado area and walk to the nearby beach and shopping/bar areas to get acclimated and relax. Behind my dark sunglasses I watch Jenny in her cute tops and the sexy one-piece bathing suits she wears at the beach and at the hotel pools, especially with Robert often next to me staring at his phone or napping. She seems to notice me but politely keeps her distance and focuses on Bobbi, and outright ignores Robert. Based on my experience and the books I've read, they will have a difficult empty nest period if he doesn't wake up.

I take stock of myself: 54 years old, 6' tall, and a little heavy at 210 pounds but it's all in my belly and I can suck it in well. A full head of hair, with some salt mixing in with the pepper. Tanned from beach time on my travels and while not muscular, and well-toned from hiking and bike riding. And quite happy with my nearly 7" dick when hard, and how it looks in the snug shorts and jeans I like to wear.

After the first few days around the pool and checking out foreign men in their speedos and the looks they are getting, I realize the swimsuits I brought are long, loose, and boring. One morning before we get together as a group, I slip away alone to buy several new ones. Not speedos, as my tan lines are still at my quads, but definitely shorter and tighter. The looks are mutual now as I often catch Jenny staring at me and my crotch and ass, and I see her getting a little jealous as other women stare, too.

At night Jenny wears nice tops and makeup and perfume, and I notice that she takes it up a notch a little more each night. I've always loved her big eyes and long lashes and try not to get caught staring but can't help myself. I get away some of the days to go snorkeling and bike-riding and leave them alone for family time, then I can't wait to see her again later for our nightly dinner and drinks.

On the seventh day I rent a car and take the gang on an all-day drive to the El Yunque National Forest on the east side of the island. Jenny is dressed in a gray cotton t-shirt and black shorts, nothing too sexy, but still cute to watch as she runs around with Bobbi while Robert sits on benches and smokes. I sit with him for a moment before he tells me to go join the girls. I keep my distance, but my eyes are glued to her every move and smile.

Back at the hotel we do a Chinese sit-down dinner then head to our separate rooms for the night. I splurged on my room with its secluded balcony looking north out over the ocean, and its plush king bed. I often sit on the balcony and watch sunrises and sunsets, both improved by the hurricane that is glancing safely past the island that week.

My doorbell rings around 9pm. Expecting one of the female maids, or maybe the handsome male butler (hmmm...) I am surprised to see Jenny at the door, alone.

"Well, hello. Is everything OK?" Maybe Jaz or Bobbi got sick or something.

"Yes, all is good. I just need someone to talk to," Jenny replies. She seems nervous and is looking over her shoulder. Unsure of what's going on, I invite her in and guide her to the balcony where I am drinking red wine.

"Would you like a glass of wine?"

"Yes, please." She discretely glances around the room as she passes through and goes out onto the balcony and stands at the railing, looking into the darkness. The beach is not far and the waves crashing on the beach are audible. I know she is a light drinker and thus hand her a small three-ounce pour.

We're silent for a few minutes, just staring outward, then she speaks. "Robert drank way too much at dinner and is asleep already. Again. And Bobbi is watching You Tube videos on headsets; I just want someone to talk with." Turning to me and smiling, she continues.

"Thank you for the fun day. We never get a car on our family trips. Robert wants us to just sit around the hotels. You're different; you move, you seek adventure."

I ignore the comment about Robert and focus only on her. "You're welcome. And thank you for including me and allowing me to be close. But I worry that Robert is getting mad."

"It's OK, don't worry about it. He is OK with you being here or he wouldn't have invited you. He wants Bobbi and I to have a great trip, and you're definitely helping with that. It's his fault if he can't keep up."

We talk for another half hour about some of the sights we'd seen that day. I come closer to show her pictures on my phone, and my bare bicep makes the lightest of contact with her arm -- another pulse hits my cock. Jenny finishes her wine and turns to leave, then pauses to kiss me on the cheek and give me a modest hug before leaving. She feels magical in my arms and then breaks away; I hold open the door for her and watch her disappear down the hall.

The next day I take the group to the west side of the island. One of the stops is a hike down a hill to Cascada Gozalandia. The sign in the parking lot describes a waterfall and pool, then a half-mile hike uphill to another fall. Robert laughs nervously and tells us to enjoy as he heads to the bar and covered patio near the park entrance to sit and smoke and drink and talk to people as we excitedly head off down steep steps. More and more it seems I am Jenny's husband and Bobbi's dad for the trip, a status which I enjoy but don't gloat about.

As we get to the first pool, Jenny peels off her shirt to reveal a sexy snug one-piece black-and-white checkered suit and makes a slow spin so I can see it all as Bobbi bounds off ahead towards the waterfall. I take several pictures of Jenny, which she seems to accept and encourage by striking modestly sexy poses before slipping away to catch up to Bobbi.

Later that night we have a nice steak dinner at a nearby restaurant. Jenny is in a sexy black strappy top and black shorts and matching heels, and her hair is up. Robert is drinking and droning on about soccer, but I can only pay attention to Jenny's beautiful eyes and big smile, and her slightly more tanned shoulders and neck. Back in my room I wait for her to knock, and just when I am about to give up and get ready for bed, she arrives.

We again go to the balcony where we look out over the beach and up at the stars. When she has trouble seeing a particular star I am alluding to, I stand behind her and grasp her wrist and stretch out her right arm as a pointer. My cheek is just behind her ear so that I can help her sight down her arm, and I whisper into her ear as I smell her perfume.

I caress her soft skin of her shoulder and bicep to guide her in locating any other star I can find. When she moves her body back into mine, I grasp her left shoulder while maintaining my grip on her rights wrist and begin caressing her blade and move down her back. My dick grows hard in the thin pants I'm wearing and contacts her hip as she backs into me more; after a pause she pushes back again, deliberately, and there is no question of intentions.

She begins to drop her right arm and I guide it all the way down so that her hand touches me. A tipping away of her head reveals her neck to me which I take as an invitation and lightly kiss her warm skin, sensing her pulse and heat rising. Her fingers wrap around my cock and start to stroke it in my pants, as my hand slides down her back and onto her ass in the short open skirt.

I'm not sure how far to go, though, and I instead turn her to me so that we can kiss for a few moments. We both enjoy it but are hesitant, and after another hug, she excuses herself and is gone.

The next day is our last full day before we fly home. Having explored the island the past few days and now without a car, we are on foot in the Old San Juan area and visiting Castillo San Felipe del Morro, a 16th century Spanish fort. Robert attempts to keep up on the long entrance walk and up and down interior stairs but is in great pain. I know there will be much drinking later and an early night for him.

Jenny is in a pretty pink top, snug white shorts, white sneakers, a fun floppy hat and perfect makeup. At first, she is a little distant from me but then begins to get closer and playful, posing for more pictures when we are alone. It's as if we are newlyweds, playful and light. After lunch in a small café she slips into a bathroom and comes back with fresh makeup and powerful red lips that I would love to kiss and have wrapped around my cock. My intense stares at her communicate my desire and I am hard all afternoon. Several times she notices and even whispers to me amidst giggles that she could take care of it for me later.

At dinner in the hotel restaurant Jenny is tapping my foot under the table with hers, then running her heeled foot up my shin and into my crotch, pushing on my growing cock and almost making me cum in my pants. Her and I share a bottle of red wine while Robert gulps down a six pack of beer. He is soon trashed and the family heads upstairs to put him to bed. I grasp Jenny's hand at the elevator and give her a quizzical look; she smiles and nods, and I know she'll soon come to my room for the final night.

An hour later she arrives. I've showered and shaved and put on my best shirt and am amazed to welcome her in a colorful snug dress and 4" heels that she tells me she bought locally just for me. Her hair and make-up are perfect, and I catch a wonderful alluring perfume as she passes me.

Once drinks are in hand we go to the balcony and immediately are standing in close contact as we stare out at the night sky. She doesn't stop me as I turn her face to kiss, nor as I caress her back down to her ass to feel its curve in the silky tight dress. As my other hand goes to her front to palm her medium-sized breasts, hers drops to my dick hardening in my pants.

We kiss for several more minutes, then she turns towards the room. I dread that she is leaving already but instead she stops at the bed and lowers one of the straps, revealing her bare breast. I quickly come close and take her nipple into my fingers, then into my mouth and suck it, and then her inhibitions are gone.

Jenny sits down the corner of the bed and unbuttons my shirt, kissing my bare chest and sucking at my nipples as she undoes my pants. She pulls out my cock and strokes it in her strong soft hands, then takes it into her mouth. She is awkward at it but wants to pleasure me and I caress her head and face and hair as she sucks me.

Not wanting to cum too soon, I pull out and guide her back onto the bed. Starting at her feet I kiss her toes as they peek out from her heel. Next I kiss her arch around one heel while stroking the other, then trail kisses up one ankle, calf, and inner thigh until I am at her crotch. Her pink panties are thin and wet and easily moved to the side as I kiss and then lick at her pussy. My licks are at her lips, then deep inside her as my nose and lips push on her clit.

Within moments she orgasms, then pushes down at her panties so I will remove them. One look tells me she wants me, and I slowly slide my hard cock into her. We make love soft and slow this first time; there will be times later for hard and fast. Once I get her to another orgasm with my thrusts, I cum myself deep within her, then roll off her to hold and kiss her. After a sigh and a smile, she stands to dress, and with a final kiss she returns to her room.

We both sleep well and have a long yet enjoyable trip home the next day. I almost dread getting my RV back and heading out on the open road, alone. Surely not for long.