This Is What Happens After You Give Your Hot Older Boss Your Cell Phone Number: Part 1

Olivier Sarkozy Sugar Daddy and Mary-Kate Olsen

Two weeks had passed since I built up the courage to send a flirty text mes­sage to Bran­don, the older man at work I was inter­ested in. If I hadn’t made that deci­sion to text him that night, I have no idea where we would be today. It was imme­di­ately evi­dent that Bran­don had some of the same feel­ings that I did. And we were both phys­i­cally attracted to each other.

How­ever, as he con­fessed to me over the phone after two weeks of stay­ing up late and talk­ing, Bran­don was not sure if I felt the same way, or if I was just a flirt—go fig­ure! Need­less to say he was relieved that I had made the first move.

It was one thing for the young, attrac­tive sec­re­tary to be nice and polite, but my flir­ta­tions kept Bran­don confused—was he imag­in­ing every­thing? These were thoughts that Bran­don shared with me dur­ing one of our late night con­ver­sa­tions. I was flat­tered when I heard that he found me sexy, con­fi­dent, and intel­li­gent. And he blamed his cold and dis­tant demeanor around me on his ner­vous­ness. The fact that he was even remotely ner­vous around me filled my ego and made me even more attracted to this man, who hap­pened to be more than twice my age. Bran­don was every­thing I imag­ined a grown and mature man to be, but to see a shy and ner­vous side of him only made me want him more.

When I brought up the pic­ture he had taken of us together—the one where I real­ized later that the top of my blouse was undone—there was a pause. “Lena, I do not at all remem­ber your shirt not being but­toned all the way,” said Brandon.

I laughed and play­fully gave him a sar­cas­tic, “Sure.”

Hon­est to God and on the holy stack of bibles, I did not see that until I was at home and flipped through my pictures.”

And did you delete it?” I asked, hop­ing he did.

Oh, no! Come on, that’s a good pic­ture, but it did come in handy that night!” And he gave off one of his bois­ter­ous laughs. I loved his laugh.

I hes­i­tated on the phone when I caught what he had just said. Ohmygod…I was embar­rassed and a lit­tle thrown off on how to respond back. So I said noth­ing. What if some­one saw it on his phone? What if he shows it to some­one at work? I imme­di­ately started think­ing of every pos­si­ble worst case sce­nario. There was a moment of awk­ward silence, and then he finally spoke again…

This entry was posted in HSD on by .

About Lena

I’d always dreamed of the perfect fairytale prince in storybooks—ready with money and status to come save me from my chaotic, average life and treat me like his princess. Add a 26-year age difference and I found the closest thing to it. Not everything comes as easy as we expect it to, but that’s what makes it all the more fun. At 18 years old, I experienced that “Mr. Right Now” love with a guy my age named Jared. Two years later, I met Brandon, my older man. Jared was the typical playboy who romanced my naïve younger self and made me fall hard for him. That relationship caused me to view love in an entirely different way than I previously had, and I’m actually glad it did. By the time I met Brandon, I had become wiser and more prepared for the reality of relationships. Even though at 20 years old I didn’t show the tell-tale signs of a smart, mature woman, that was exactly what I had become. I started as a part-time secretary for a highly respectable office, while juggling a full-time load of college courses at the local university. It was my first official job where I had to wear heels, pencil skirts, and an occasional suit. I was no longer the high-school girl that found “true love” after graduation and had her heart broken immediately after. The new woman I was now was confident and smart, and when I saw Brandon walk through the lobby door, I knew he’d be a challenge, one I was ready to accept. Now at 22, and Brandon at 48, we’ve managed to keep a two -year relationship feeling like the very first day we met—all the excitement and butterflies are still very much present.