Jessi's Bucket List

by Laptopwriter

Copyright© 2016 by Laptopwriter

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?

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

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.

Eating dinner was a little surreal. The restaurant was an open air, wooden structure with shutters on the side—for when it rained, I'd guessed. The floor was nothing more than the beach. We both laughed as we were shown to our seats and noticed people dropping bits of food under their tables for the iguanas. As rustic and islandy as the place was, its chef was five-star all the way. Both Jessi and I had one of the finest meals we'd ever tasted ... and when we were all done we fed the iguanas our scraps.

Later we grabbed a cab to another hotel that had a live calypso band. Although the beat was different than we were used to, Jessi and I did our best to keep up with the islanders on the dance floor. The place was only about a mile down from our hotel so we decided to walk back along the beach. We watched the rays of moonlight surf the waves as they crashed at our feet. About midway back I stopped and pulled Jessi into me. We could still hear the music as I pressed my lips against those of my gorgeous wife. I think it was the most romantic kiss we'd ever shared.

That night we made love to one another while the waters of the Caribbean caressed the sand just outside our door. Something in the tropical air made Jessi's body almost over react to my every kiss. Her hands grasped at the sheets and her body writhed wildly at my every touch.

"Oh, God!" she cried out. "Fuck me, Miles. Come on, honey, put it in—fuck me."

Almost immediately, I could feel the inner walls of her pussy contracting and she had her first orgasm as I slipped inside of her. I waited until I saw her eyes open again, then slowly started to stroke back and forth in rhythm with crashing surf outside our door.

She reached up and put her arms around my neck. A few seconds later she locked her ankles around my waist and pulled me as deeply into her as possible. I could feel her hips swaying in tempo with my own. Her second orgasm hit her harder than the first. She tightly clung to my body, jerking with fervid spasms of ecstasy.

I let her catch her breath before starting again. I was getting close myself.

"Oh, oh, oh," she squealed, "yeah, come on, baby. Yes, yes, you too, you come too," she yelled.

I was trying to hold off just a little while. I knew she was close. Just when I didn't think I could prevent the inevitable any longer I felt her pussy clamp down and start milking me. I exploded with every muscle in my body as tight as a rubber band ready to snap.

As our exhausted bodies cuddled on the way to dreamland, I thought this truly was a magical place.

Sunday, after breakfast, we rented a jeep for the week and went exploring. Most of what we explored were the shops in town. If you wanted cameras, jewelry, or liquor, that was the place to go. In one store, Jessi fell in love with some pearl shell earrings so I didn't hesitate to lay out the cash. I wanted to make sure this was one vacation we'd remember the rest of our lives.

The nights were romantic and the days, adventurous. We were both in seventh heaven.

The first few days we had been so busy that on Wednesday morning it struck me; half of our vacation was over already and I had yet to go swimming in the ocean. I wasn't about to go home without swimming in the ocean at least once in my life.

We were eating lunch in a little spot that was professed to be where pirates of old gathered to drink rum and tell tall tales.

"Honey, when we get back to the hotel I'm going to take a dip in the ocean. You going to come with me," I asked, knowing what her answer would be.

"You mean go swimming with the sharks? I don't think so."

"Oh, come on. They don't eat much," I joked.

"No, you go ahead. I'll take a dip in the pool while some great white is picking you out of his teeth," she teased.

So, that's what we did. As soon as we got back to our room, Jessi maneuvered into one the three pieces of string she called a bikini while I slipped on my trunks.

Every time she went out in public like that I got uneasy. I was proud as hell that my wife looked that good and could still wear something like that but I preferred she wore it for me only. Of course I wasn't going to ruin our vacation by expressing that to my wife. I'd learned years earlier that sometimes in a marriage you just have to suck it up. This was one of those times.

We grabbed a couple towels, gave each other a peck on the lips, and headed off in different directions; she turned toward the pool while I navigated to the warm waters of the Caribbean.

The first thing I realized was that it was lot different than swimming laps in the pool at the health club. Fighting those waves was down-right tiring. I hadn't been out there all that long and I was getting pooped. I really hated to go in but I wasn't going to be stupid so I started for shore. By the time I got there I was exhausted and flopped down on one of the lounge chairs. After a few minutes I learned another lesson; you don't lie out in the tropical sun after swimming in salt water. It bakes the salt right into your skin.

My whole body was suddenly on fire. I jumped up and made a dash for the room. I jumped into the shower and turned the cold water on. At first it felt like a thousand bees bombarding my flesh but eventually it put out the fire. I gently washed my red, irritated skin then found some lotion in my wife's bag and gingerly rubbed it in.

Not wanting to put clothes on just yet, I flopped on the bed and closed my eyes for a quick rest. I actually drifted off for a two hour cat-nap. It was just what I needed. I felt like a new man again, and although my skin was still a little sensitive, I had no trouble dressing.

When I finally looked at the clock I was surprised Jessi hadn't returned yet. I got worried that she might have fallen asleep herself and was getting sunburnt so I started toward the pool.

I didn't see her at first but spotted them on my second scan of the area. Yeah, "them." They had two chase-lounges pulled up close to each other. Jessi was resting on her back in one with you know who sitting on the other with his back to me. There was a tube of sunblock lying next to him and I knew without a doubt that he'd had his hands all over my wife's body again. Their heads were so close together they were almost touching and they were talking so low it was like they were whispering to each other.

I wasted no time in approaching them and was finding it harder and harder to keep my cool around this jackass. They seemed to be so involved in whatever they were talking about they didn't see me until my shadow covered them. That's when my wife shielded her eyes and squinted in my direction.

"Oh, Miles; are you done with your swim already?"

"Already? It's almost five-thirty."

"Really? I didn't realize it was so late. We've been talking. You remember Carl."

"Yeah, I remember Carl." I looked him straight in the eyes. "Always johnny on the spot with that suntan lotion aren't you, Carl," I snidely remarked.

Somehow Jessi missed the sarcasm in my voice but he didn't.

"Well-I have to get going," he uttered while standing up. He stretched his hand out in my direction. "It was nice seeing you again," he said with a grin.

I didn't say anything and the grin disappeared when I didn't shake his hand. As he left I was hoping he got my message. I also decided, vacation or no vacation, I was going to have a talk with my wife who seemed to be oblivious to my feelings.

That night, over dinner, Jessi seemed just a little anxious. Maybe she did sense how I felt after all; maybe she was looking for an opportunity to apologize. Okay-I'd give it to her.

"What's going on with you and this Carl guy?" I had expected to hear an, "I'm sorry," but instead I got denials; although she hesitated before answering, almost like she was going to say one thing then changed her mind and said something else.

"What do you mean, honey? Nothing's going on. He's just a nice young man, that's all."

"Bullshit. He's hanging around you like a dog in heat. What were you two whispering about this afternoon?"

"We weren't whispering. For crying out loud, Miles, are you really that jealous over some kid?"

"It just seems like every time I see him with you it involves a tube of sunblock. I'm not crazy about some stranger having his hands all over my wife, I don't care how old he is."

She didn't say anything in response and I thought I'd made my feelings clear so I was ready to drop it. "Okay?" I asked, driving home my point.


"Good--enough said then. How's your red snapper?" I asked with a grin.

That night we went out to sample some more island nightlife. When we got back, uncharacteristically, Jessi didn't wait for me to initiate anything, she literally jumped my bones. Within thirty seconds after entering our room she had my pants down around my ankles and my cock in her mouth.

If this was her way of finally apologizing it was worth the wait, I thought. She licked, slurped, and deep throated me. Within a minute or so I was so hard it hurt. That's when Jessi stood up and hurriedly reached under her skirt to pull her panties off. She climbed on the bed with her hands and knees and stayed like that.

I knew she was wet and wasted no time guiding cock into her waiting slit. I took ahold of her waist and rocked her back and forth.

"I want it hard," she snarled. "Fuck me hard, give me your cock."

I did my best. I gave her just what she asked for. I plowed into her with our bodies making that slapping noise every time I rammed my penis to the hilt. It didn't take long before both us erupted in euphoria.

After catching our breath we made slow, gentle love to one another. I'm not sure how many times she climaxed but after my third time I had nothing more to give. We cuddled in each other's arms and slipped into dreamland.

I awoke the next morning wishing we could just stay there and never go back home. The place was paradise in every sense of the word as far as I was concerned.

I was hoping for a replay of the previous night when Jessi woke up but she didn't seem in the mood so getting each other off during our morning shower was about as good as it was going to get until later.

I couldn't believe how the time had just flown by. It was Thursday already. We had only two days left and Friday was already booked. Before we even left home we had signed up for a full day sail to one of the other islands. It would be us and two other couples plus the boat's three man crew. When we got there we'd anchor in an isolated bay and go snorkeling. We'd stop for lunch then do some more snorkeling before heading back to St. Thomas. We would leave at nine in the morning and get back about seven in the evening.

Jessi and I talked over breakfast. Since we were going to spend most of Friday on the boat we decided to just hang around the hotel for the day and enjoy the beach. As the morning progressed, Jessi seemed to become more and more antsy. I should have known something was in the works but I assumed, like me, she just didn't want our vacation to end.

It wasn't until we were eating lunch that things started coming to a head. Before we were done the alarm on Jessi's phone went off. She immediately reached into her purse, pulled it out and shut it off.

I couldn't figure out why she would have her alarm set for the middle of the day. "Were you expecting to be taking a nap?" I asked.

"No," she quickly answered, "the alarm must have gotten turn on by accident somehow."

She had been picking at her food through lunch and half of it was still on her plate when she excused herself.

"Where are you going?"

"To the lady's room," she snapped. "Why, want to come and hold my hand?"

Again, I contributed her little burst of temper to the fact that we had such little time left.

I watched as she traipsed through the sand and headed toward the front entrance to the hotel. I wondered why she'd use the public bathroom in the lobby. The back door to our room was just as close.

I finished eating my lunch and sipped on my ice tea while waiting for Jessi to return. After several minutes our waitress came over and asked if we were finished. I wasn't sure what to tell her. I went ahead and paid the bill but asked if she'd leave the salad for right now. I told her my wife was in the washroom and I wasn't sure if she was done or not.

When she still hadn't come back after fifteen minutes I decided to see if she was okay. I motioned to the waitress that I was leaving. I spotted Jessi as soon as I walked into the hotel. She was standing on the other side of the lobby talking and who do you think she was talking to? At least he didn't have a tube of sunscreen in his hand.

This time he saw me before I even got close. He quickly said something to Jessi then turned and walked away while she turned around to face me. "Checking up on me?"

I figured she was coming out of the washroom and ran into Carl. It all looked very innocent so I wasn't even going to say anything. "No, but you said you were going to the bathroom and then didn't come back. I came to see if you were okay," I answered.

She had kind of a weird look on her face and I was starting to wonder if there WAS something wrong.

"Miles, let's go to the room. There's something I need to talk to you about."

Now she was starting to worry me. There was a determination in her voice and I couldn't imagine what could be so important unless it had to do with our daughter. She was away at her first year of college.

"What's going on?" I asked as soon as we entered the room. "Is it Sari? Did something happen to Sari?"

"No, no, Miles, it's nothing like that. No one's sick or hurt. Everyone's fine."

I'm sure she saw my relief but it didn't seem to matter to her. She still looked anxious. She looked at me and actually started wringing her hands. She hadn't done that in years.

"Jessi, what the hell is wrong? You're really starting to scare me."

"I'm sorry, Miles. It's really not that bad, I'm just trying to figure out the best way to tell you."

"Tell me what?"

"Here," she said motioning to the bed, "let's sit down."

We both sat down then stared at each other for a couple seconds before she started talking. "Miles, do you have a bucket list?"

At first I had to think about what she was even asking. "A bucket list? I'm only thirty-eight years old. No I don't have a bucket list ... why?"

"Age doesn't really mean anything. I think everyone has things they want to do before they die," she replied.

"I guess, but I haven't really thought about it." Just then a terrible notion hit me. "Are ... are you sick?"

"No, I'm not sick but I do have a bucket list."

I still couldn't figure out where she was going with all this. "Jessi, stop beating around the bush. You said you wanted to talk to me about something. Spit it out, please."

"Okay," she said, taking a deep breath. "I'm going to have sex with Carl tonight."

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