*What are you thinking this year? Nice? Santorini? The Maldives?*
It’s become a tradition since you went off to college. For the last three years I’ve looked forward to our summer vacation more than I did growing up as a kid begging for school to end. Now I’ve got more exciting diversions to fill my time than riding bikes and playing video games with my friends. Namely, you and your friends.
With a certain level of wealth comes expectations. Every public appearance becomes an opportunity for shareholders and tabloids to speculate on far too many aspects of your life. Spend the afternoon riding jet skis instead of your yacht? Must be trying to save money and avoid layoffs coming soon. Bring the same date to two events in a row? Suddenly everyone has to search for skeletons in her closet and insert their opinion on whether or not she’s appropriate match or some gold digger.
Five years ago, I got tired of that endless circus. I realized I was getting too old to try and romance B-List Hollywood Celebrities or hire Instagram models to escort me to all the parties and events my lifestyle demanded. Black Tie Charity Galas. Grand Openings. Corporate Parties. Just the logistics of having to reach out and find a date for each and every one was stressing out my assistant. It was time to settle down and find a wife.
Your mother was just what I needed. We had a whirlwind romance and went from dating to engagement to marriage in less than a year. We both knew what we wanted and just felt comfortable together. She quickly fell in love with the luxury and security I could provide her. In turn, I no longer had to endure those awkward questions about my date being young enough to be my daughter. For someone who had spent most of her career as a teacher, she picked up the etiquette and charisma needed to thrive in our stressful social calendar. Most importantly, she came with an instant family, making me look like the down-to-earth multi-millionaire CEO my publicist tried to sell me as. She was beautiful and sweet and would have been perfect if I hadn’t been spoiled by decades of gorgeous women who couldn’t tell me no.
It took me almost two years to get bored of her. I thought I could sneak away for a weekend or two here and there to get it all out of my system, but I missed those young enthusiastic coeds wrapped around each arm. Knowing better than to embarrass the both of us and get caught, I continued sneaking around as covertly as possible. Your mom never noticed, but I should have known you’d be more attentive. When you pulled me aside and asked how my last “work trip” went and what I’d been up to, but I knew something had to change.
An idea came to mind. One so fucked up, it took me a few days to come to terms with it. Some father-daughter bonding would be a hell of a lot less suspicious than a solo vacation. Maybe we could find an arrangement that satisfied both of us. And so, I started slowly shifting my attention towards you and telegraphing the question I was about to present.
In hindsight, I probably laid it on a little too thick. I needed the signs to be obvious though. The way my laptop always seemed to be left open to your Instagram, like it was my homepage. The fact that my phone screen was the three of us, not just your mother and I. How I insisted you host parties at our house, pretending to worry about you drinking with some stranger while I fired up the grill and enjoyed the parade of bikini-clad coeds you brought in the door.
You’re a smart girl. I should have known you’d pick up on it fast and that all that effort was overkill. Spring Break was coming up and your friends knew exactly how rich I was. Funding a vacation that would blow their minds would be a rounding error on my income this year. You saw the way I looked at you and figured batting your eyes would have me wrapped around your finger at any request. This was my opportunity for a proposition of my own.
One week. You pick the destination. I surprise your mother with a girl’s trip for her and her friends on the opposite side of the globe. My secretary lies about a work trip and I pick you up in my private jet. Then we spend a week having the time of our lives. Shopping for outfits you can’t afford. Sightseeing at places you’d always dreamed of visiting. Beaches. Boats. Drinks. All you’d have to do is be my date, instead of my stepdaughter. A girl like you knew how to have plenty of fun and we lined out the strings that came attached with that fun.
I paid more than any summer job you or your friends could pick up, even if you climbed to the top of the charts on OnlyFans. As a show of good faith, I went ahead and covered the cost for your Spring Break trip for you and your friends. and made sure you had plenty of spending money to tide you over until summer came around, the semester ended, and I had you all to myself.
The first trip was nothing short of incredible. I’d never met any woman I’d had so much chemistry with. If it wasn’t so taboo, I think both of us might have reconsidered this arrangement as a more frequent one. Each year it seemed like we went bigger and wilder and kinkier, having the time of our lives together.
This year I want to make it one we’ll never forget. After spending a weekend on a yacht last time, the only thing that could make it more perfect would be inviting your friends to join us. We’d talked about it before, but I’d never really pressed the issue. Sending you a picture of a pair of strappy bikinis laid out on my bed with a few stacks of hundred dollar bills, I tried to make my intentions for this trip crystal clear as I followed up my text from earlier.
*What about your friend Kendall? Think you can convince her to join us? I’m dying to see how you’d both look in matching swimsuits.*
Thanks for your time and interest. I’m eager to hear a little more about your ideas on our characters and directions we could take the story. [This link](https://imgur.com/C4CgDeE) has a little more info on my kinks and limits. Please tell me a little more about your own and your writing style in your reply. Hope to hear from you soon.