Author's note: Sexual fantasies often require a suspension of disbelief to enjoy; written sexual fantasies are no different. Still, most of my stories attempt to be at least somewhat grounded. Even for less likely scenarios, my hope is that with proper setup, they're at least plausible.
But in the real world, the 'unrealistic' happens all the time. Lotteries are won daily. A blind man has climbed Mt. Everest. A woman survived a 6-mile fall from an airplane parachute-free. You get the idea.
This story focuses on a man who experiences the sexual equivalent of winning the lottery. Unbelievable? Maybe. But unbelievable doesn't mean impossible.
Please note: this story contains no incest, orgies, or lesbian encounters. Sorry to disappoint or happy to reassure, depending on your sensibilities. Also, this story is a story in the full sense—there is plenty of sex, yes, but there's much more going on too. Don't expect a quick dive into the action.
It's also my longest story yet.
The good parts are scattered throughout, so I'd recommend working through the story a little at a time.
It's your choice, of course, but as the main character observes later, it's meant to be sipped, not chugged.
And the usual disclaimers: all characters are fictional, similarities to real-world people/events are purely coincidental, everyone involved is of legal consenting age, etc.
"So, we're still doing this—aren't we, Dad? You promised!"
Alex leaned over the kitchen island, looking at me expectantly.
I sighed. "I did promise, didn't I? In that case, I guess I'd be a real jerk to say no now."
"Yes, you would. We'd never forgive you."
"In that case, fine. I guess we can still go. Go ahead and talk to your friends. Make sure their parents are fine with it first." I made a show of begrudging acceptance.
"Yes!!" Alex screamed, fists pumping the air. She ran over to me and pulled me into a tight hug. "I love you so much, Dad!"
"I love you too, Little Goblin," I said, messing her hair affectionately.
Alex—Alexandra on her birth certificate—was my seventeen-year-old daughter. I'd promised a free trip to Jamaica for her and her four closest friends once they finished high school. My offer was given out of desperation, and although it had worked at the time, it appeared the time to pay up had arrived.
I would have done it again in a heartbeat.
I'm a single father. Technically a widower, but it feels odd to use that term since I'm only forty-two. My late wife (and Alex's mom), Emily, was killed in a car wreck after we'd been married about ten years. Alex was only eight at the time. The two of us were devastated; our lives destroyed as thoroughly as the car Emily had been in. But somehow, we persevered.
Alex's circle of friends was critical to her recovery. Rachel, Cari, Jasmine, and Macy. Those four girls have my undying gratitude for helping Alex through the most difficult time of her life. And it wasn't just Alex—they were a godsend for me too, supporting my only child through an unspeakable tragedy. I have no doubt: those four girls are why Alex can see joy in the world again.
I won't pretend it was easy. We had plenty of hard times. Alex would sometimes lock herself in her room and cry for hours. Nothing made me feel so helpless as a dad as to watch Alex fall into depressive episodes... and be totally unable to stop them. The anniversary of Emily's death was always a trigger, but just about anything could remind Alex of her loss. Old pictures. Certain songs. Even an omelet at a restaurant that tasted like the omelets Mom used to make.
But year-by-year we made it through.
Until spring semester of Alex's junior year. By then, Alex had gone almost ten years without her mom. That black anniversary had hit her hard enough, but then it was worsened by another realization. In a year, Alex would be graduating... and her mom wouldn't be there to see it.
Alex spiraled hard. I pulled out every trick in the book to bring her back, but nothing I tried worked. Medicine, therapy, a new puppy... nothing. Alex's friends did a phenomenal job of offering comfort and support, but even they only had limited success. Alex began to skip meals, and her grades dropped. I panicked.
I don't know if my Jamaica-trip offer was what made the difference. Maybe Alex had just finished working through her grief on her own. But in the end, it didn't matter: Alex improved. My daughter was back, and I cried tears of joy for the first time since Emily's passing.
One day when Alex's friends were over at our house, still trying to comfort her, there was a commercial for an all-inclusive resort in Jamaica that played on the TV. I was struck by inspiration and made the off-the-cuff remark that if all five girls made it through their junior year without failing a class, I'd offer to take them all for free after they graduated.
The response from Alex's friends was electric. "Are you serious, Mr. K?", "Don't say it if you don't mean it!", and "Alex, your dad is the best!"
And so on. They began researching Jamaica on their phones, assessing the various excursion options, and designing itineraries for their unexpected dream trip. Their excitement had a subtle but profound effect on Alex... for the first time in weeks, I could see her take an interest in the world again. Over the next few days, the girls continued to plan their island escape... and Alex joined in. The travel bug had bitten her.
Fast forward to that summer—Alex had returned to her old self and was ready to cash in on my offer. Neither she nor her friends had failed a class; my conditions had been met.
I was more than happy to pay for everyone to go. Emily had a sizeable life insurance policy that paid out after her death. Some of it I had earmarked for Alex's college, but there was plenty left for everyday life... and special occasions like this. We weren't rich, but we were comfortable. Which is its own sort of rich, I guess.
But now that this theoretical trip was becoming real, I faced a challenge: coordinating everyone's schedules... and getting permission from the other girls' parents. The girls would all be eighteen by the time of the trip, but for now, they were underage. I wasn't going to whisk them all to a foreign country without an explicit go-ahead from their families.
Surprisingly, with one exception, all the parents agreed. They all knew and trusted me, but there's a difference between supervising a sleepover and supervising a week-long trip in a foreign country. I suspect most of them were swayed by their children's excitement... and by sympathy for Alex's situation.
All of them except Macy's parents. They were reluctant to send their only daughter so far away without a family chaperone. But after I visited them personally and offered them my reassurances of Macy's safety, they too came around.
Next step was passports and booking. This went smoother than expected. The passports took several weeks to arrive but were otherwise a breeze. I picked the resort—I wasn't about to take the girls to a party hotel—but let the girls pick the rooms and other add-ons. Then came flights and other travel concerns.
And then we were done. Three rooms booked for a resort in White House, Jamaica, arriving on a Sunday and leaving on a Saturday. By this point, my own excitement rivalled that of the girls... even knowing I'd be babysitting them.
With the trip locked in, all that was left was to wait for it to arrive.
Alex's senior year flew by. Her troubles from the previous year had vanished, and although Alex still had the occasional bad day, they were rare. Alex aced her classes, won some academic awards, and was accepted into her first-choice college. When she walked at graduation, my tears flowed openly.
And just like that, it was time for Jamaica.
We all met at the local airport; family goodbye-hugs and more reassurances of safety. A trip through security. Waiting for our plane.
During this downtime, Alex and her friends chatted excitedly about their upcoming adventure. Moments like this, I marveled at their friendship. They were a diverse group. If it weren't for their mutual support of Alex over the years, I suspect they would have drifted into other circles. But they hadn't. And now, they were friends for life.
Each girl brought something unique to the group.
First, there was Rachel. Alex's friend circle didn't have a designated leader, but if they did, it would have been Rachel. Rachel was the social media queen—think airbrushed photos and adventurous outings. I had no doubt that this trip would be a goldmine for her. She was outgoing, rambunctious, and very image-conscious. But she had a sensitive side too. She was Alex's most frequent go-to when Alex needed someone to confide in.
Then there was Cari. Cari could come off as quiet, but she was every bit as extroverted as Rachel. She just preferred to listen first, then talk after. She also had a mischievous streak. When she and Alex were kids, she once snuck a handful of water balloons into their bedroom during a sleepover, unleashing havoc. Yet somehow, her pranks seemed endearing rather than malicious. Maybe because she always made herself a target as well... like soaking herself with her own water balloon. Within the group, Cari was closest with Jasmine—they played competitive volleyball together.
Jasmine was a bit of a mystery to me. Like Cari, she was an athlete, but that's about all that was obvious about her. She was very quiet, generally speaking. I don't know if she was just shy around me or if she was subdued all the time. Either way, she was hard to read. She was always very polite, though, and I liked her even though I sensed I'd yet to see the real Jasmine.
