Jessi's Bucket List


Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa, Fiction, Cheating, .

Desc: Fiction Sex Story: They were finally going on their long awaited vacation. How could something that started so great, turn out to be so bad?

First, let me apologize to those who wrote me, asking when I would be posting new stories. I have several in my queue and thought I would have them published long before this but life kept getting in the way.

I hope you enjoy the story and please, you know how much I enjoy the feedback.

Thank you.

Jessi and I had been together since we were juniors in high school. Yup, it was love at first sight for both of us. Of course, at the time everyone said it was just puppy love but there we were, twenty years later with one daughter in college and still very much in love.

At least that's the way I felt...

Looking back over our lives together it's incomprehensible for me to believe the events that took place on our long-awaited vacation to the Virgin Islands. It was only for a week but we had been looking forward to it for four years and only with a stroke of luck did all the planets align in such a way that made it possible.

It all started one Friday afternoon when I called Jessi from my office...


"Hi, honey. How's your day going?" I asked, trying not to sound too excited.

"Alright, I guess. Miles, is everything okay? You never call me from work."

"Everything is fine, honey. I just wanted to tell you not to bother cooking tonight ... and put a nice dress on, I'm taking you out for dinner. I thought we'd go to Plato's Place."

"Plato's," she repeated, sounding a little shocked. It certainly wasn't the least expensive of restaurants. "Isn't that place a little swanky for our tastes?"

"Nope, not tonight; I've got some good news and I'd rather tell you across a candlelit table while enjoying some after-dinner wine," I told her.

From the time I got home, till we took our first sip of wine, Jessi tried to pry the news from my lips but I held my ground until I was ready. "Okay, I know you're dying to hear the good news so here it is. On my way to lunch today, I had to stop for gas. On a whim, I bought a scratch-off lottery ticket. It was worth five thousand bucks."

It took a few seconds for the news to sink in. "Fiv ... five thousand dollars?"

"EeeeYup!" I said with a big grin.

"Miles, that's wonderful. Oh my gosh! I'm so proud of you." With that she stood, walked around the table and gave me a passionate kiss right there in the restaurant. As she returned to her seat I hit her with the second phase of my surprise.

"What's this," she asked, taking the envelope from my hand.

"Open it and find out," I responded.

Almost everyone in the place heard the scream as she spotted the two tickets to the Virgin Islands.

Neither of our parents were rich and we got married so young we couldn't afford a honeymoon. Within the first year Jessi became pregnant with our daughter, Sari, and financially it's always been an uphill battle. About ten years ago we got far enough ahead that we were able to start a college fund for Sari but it seemed like every time Jessi and I just wanted to get away from it all, something would come up.

We'd been talking about going to the Virgin Islands for the last four years and actually had twenty-five hundred bucks saved up toward the trip—then our roof started leaking and we wound up spending three grand on the repairs. It just always seemed to be our luck ... but not this time.

"Seven days and six nights," I told her. "In two weeks from Saturday we leave from O'Hare at seven in the morning and land in St. Thomas about one in the afternoon. Coming back we have to leave there early the following Saturday."

For the next couple weeks she was one excited wife. Of course I got all the nookie I could take and thought it was all due to my hard work and good fortune. As it turns out, Jessi had an ulterior motive that I knew nothing about.

The morning of the trip, we had to be up at three a.m. Neither of us got any sleep on the plane so by the time we arrived Saturday afternoon, both Jessi and I were bone tired. We grabbed a cab from the airport and had already decided the first thing we were going to do was take a nap. Then we saw the hotel and that idea went right out the window.

It was like a tropical paradise. Our room was decorated like a tiki hut on the inside and the glass sliding doors opened right onto the beach with the beautiful aqua waters of the Caribbean only steps away. Just down the shoreline there was an open air restaurant where you could enjoy a wonderful meal and a bar that was almost on the water's edge for relaxing with a Pina Colata while listening to the pounding surf. It was heaven on earth.

Jessi and I decide that if we had to rest up we'd do it on one of the many chase lounges the hotel supplied along the beach. We both popped open our suitcases as we started to strip. That's when I saw the first of three new bathing suits Jessi bought for the trip.

I was a little surprised. At just thirty-eight, we were both still in pretty good shape, Jessi especially. She still had a dynamite body, I'd just never known her to display so much of it in public before. "Damn, Jessi, I hope you didn't pay a lot for that. There's probably no more than twenty-five cents worth of material in the whole thing."

"You don't like?" She asked with a pouty face.

"Oh, I never said that," I replied with a grin.

Even though it was our first time there, we'd read all about the dangers of the hot sun, so after slipping into our suits we rubbed each other down with an ample supply of sunscreen and ventured out through the scorching sand ... and I do mean, 'scorching.'

We quickly found two empty lounge chairs side by side and claimed them for our own. We stretched them out so we could lay back and enjoy a well-deserved rest. I hadn't actually planned on going to sleep, just rest my eyes, but the hypnotic sound of the waves was like a lullaby. Within minutes I was drifting off with visions of mermaids and sunken pirate's chests permeating my dreams.

Just as I was about to declare the King's treasure for myself and rescue Black Beard's female captive from a fate worse than death, my hallucinating revelry was disturbed by an invading force ... voices. They were pulling me back into reality. I was awake but hadn't opened my eyes yet. I just laid there enjoying the warm ocean breezes.

I was actually thinking about going back to reap my rewards for liberating the fair damsel when I heard it again and recognized it as what had awakened me; it was the sound of my sweet wife moaning with pleasure. Suddenly the thought hit me, if I'm laying here, who the hell is pleasuring my wife?

I opened my eyes and saw a good-looking young man massaging more sunscreen onto her back. I was so shocked I froze for a second as his hands moved down to the exposed cheeks of her ass, covered only by the thin piece of material that did little more than hide her butt crack. "Uh umm," I said as if clearing my throat. "May I ask just what the hell is going on?"

Romeo looked over and smiled. He was just about to say something when Jessi turned her head toward me with a big grin. "Well, welcome back to the living. I needed more sunscreen and you looked like you were enjoying your nap so much I didn't want to disturb you. Carl here saw me trying to reach around my back and volunteered to help," she nonchalantly explained.

"Hi," he said, showing all his teeth. "As your wife said, I'm Carl. I'd shake your hand but I have lotion all over mine. Jessi said it's your first time here. I teach scuba diving. You and your wife should sign up."

"Yeah, maybe we will," I said, knowing there was not a chance in hell. I reached my hand out. "I think I can take it from here."

Romeo politely gave me the sunscreen. "I live here at the hotel so I'll probably see you two around. Think about those scuba lessons. It's a whole different world down there. Once you try it you'll be hooked."

"Thanks, I'll give it some thought," I said while squirting lotion into my hand. I started rubbing the back of my wife's legs as he walked away.

I guess it was innocent enough, after-all they were both in plain site with me right beside them, but I was still a little miffed and wanted Jessi to know it. "Since when do you let strangers feel you up like that?"

"Oh come on, Miles, he wasn't feeling me up," she replied dismissively.

"He had his hands all over your ass," I growled. "I'd say that was feeling you up."

"Honey, I doubt if he's much over twenty. He was just being helpful," she said while reaching into her bag to look at her phone. "Oh, it's after five, honey. We should get cleaned up for dinner."

I knew she was purposely changing the subject and we were on vacation so I certainly wasn't going to allow myself to get angry over it.

As soon as we got back into our room, Jessi did a little striptease for me. Of course there wasn't a lot for her to strip off but the suggestive little dance she was doing had me hard even before she pulled the string-tie on her bikini bottoms and let them fall to the floor. We both needed a shower and I could see no reason why we shouldn't be good tenants and conserve water so we hopped in and lathered each other up. I won. She got me off once to my getting her off twice. She demanded a rematch later that night and I was only too happy to accept her challenge.

.... There is more of this story ...

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Story tagged with:
Ma/Fa / Fiction / Cheating /