My Generous Lover, Part One
I’ve always been a woman of expensive tastes. This is the story of how my expensive tastes led me into the bed of a millionaire.
When I saw the dress in the boutique, the one with a white gauzy skirt, a low-cut, crisscrossing back, and short, fringed cap-sleeves, I fell in love for the first time in my life. It had to be mine, I decided, and I had to wear it somewhere fabulous. But my pocketbook couldn’t afford the three-figure-and-then-some price tag, and so on the rack it stayed. I didn’t even bother to try it on, instead letting myself buy a pair of earrings from the jewelry stand near the counter. On my way out of the store, I gave its skirt one last caress, the material butter-rich and feather-soft, making me want it even more.
But my student loans were always squeezed around me like some kind of medieval torture device, an Iron Maiden of debt destined to hold onto me until I found a job which paid well enough to make some sort of reasonable dent in them.
Maybe I should get a sugar daddy, I thought to myself. The thought was sarcastic, but the sentiment behind it was not. I wanted nice things, things like that dress, like the shoes in the shop windows I walked past, like the meals served in restaurants I knew I’d never see the inside of. Not on my budget, at least. But maybe on someone else’s…
No, it was a ridiculous idea. Just another one of my silly flights of fancy. I walked the ten blocks back to my hovel of an apartment and made myself a bowl of ramen and miso. Yep, this was how it was going to be for a very long time.
But the idea didn’t leave my head for the next few days. I was good-looking enough for it, as long as the man’s standards weren’t ridiculously high, my hair full of body and my lips what one might call “pouty” if they were being kind. After one more day of weighing the idea in my head, I decided to say to hell with my doubts and go for it. The worst that could happen would be a complete lack of replies.
I used the old standby known as “Craigslist” to set my trap. I put a photo of myself in my ad, in which I wore a bikini and reclined on a chaise lounge, a picture taken only a few months ago, so at least it was relatively accurate in terms of what the man would see when he met me. I wrote about how I wanted a “sugar daddy”, about my student loans, as well as my interest in traveling, eating good food, and lounging in bed all day. That last part troubled me a little… would they think I was talking about their bed? Well, admittedly, sugar daddies didn’t just expect you to look pretty… they expected you to act dirty, too. I supposed, if he was attractive enough, that yes, I’d be happy to sleep with him, provided that his wallet was easily opened and hard to put away. And provided that we had chemistry, too; provided that he sparked the fire that caused my libido to rise up and take notice. Money alone wouldn’t get me into bed with anyone, no matter how rich the guy happened to be. I loved sex, sure, but I knew I couldn’t talk myself into fucking just anyone.
The responses came pouring in only minutes after my ad went up. Some men asked if I was a whore, some sent pictures of hard and ready anatomy, but only one out of the fifty-plus replies that came in the first hour caught my eye.
This one had a picture, but it was of a man, not just a penis. He had salt and pepper hair, shaggy and thick, and he was grinning in the photo, his eyes surrounded by what some call “crow’s feet” but what I tend to call “laugh lines.” He was very handsome, and his email was light and funny. He wrote that it was unlike him to answer an ad like mine, but he thought I was sexy (always nice to hear from a good-looking man), and that he thought it might be nice if we went out to dinner at Ophelia, got to know each other a little, and talked over the possibility of us trying out this whole “sugar daddy” thing. His name was Evan, and he was cute, and rich, and had spelled everything in his email correctly. So I replied that yes, I would love to have dinner with him, and we set a date for the following Friday night.
Now came the horror of deciding what to wear.
* * * * *
I showed up at six-thirty, wearing a pale gray pencil skirt and a flowing, silk tank. Hopefully he would approve. Once inside the restaurant, I scanned the room. There he was, sitting at a table in the far corner, sipping a glass of red wine. I slowly made my way over to him, and he looked up when I was halfway there. Fuck, I thought. He wasn’t just handsome — he was incredibly handsome, more than a fair bit better-looking in person.
He stood when I got to the table, walking around to my side to help me into my chair. He obviously came from another era, one where you treated your date the way men my age would never think to. I guessed that he would open car doors for me too, a thought which made me smile.
“You look happy, Diana,” he said as he sat back down in his chair. He was quite well-dressed, I noticed, wearing an expensive-looking gray suit, and his silver cuff links sparkled in the candlelight.
“Yes, I think I am. Happy, that is.” I placed my hand on the table, and moments later he put his own over it, the way a lover might, then slowly rubbed his thumb up and down its side. I couldn’t help it—I shut my eyes at his touch, because I also couldn’t help getting very aroused as his thumb slowly slid back and forth across my skin.
“Now,” Evan said, “Order anything you’d like on the menu, because, as I’ve always wanted to say, ‘money is no object.’”
I opened my eyes as soon as he spoke, and laughed a little at his words. Good, he had a sense of humor.
I ordered osso buco and a glass of Sauvignon Blanc. The food was some of the best I’d ever had, and luckily, the company was just as delightful. Evan talked about his childhood—he’d spent his first five years in England, then moved with his parents to Seattle, and had stayed there for seventeen years, even going to college there. After college, he’d started an advertising firm, where he still worked, but it had grown vastly in size since its humble beginning, and now he was the boss of over one hundred people. Evan told me that he was thinking of retiring now, though, selling the company and moving somewhere else—the country, perhaps, because this big city life was starting to get to him.
“I know what you mean,” I told him. “I’m only twenty-four, and I already want to live somewhere quieter, mellower. Like you said, the country, perhaps. I know my student loans will follow me wherever I go, though, and the pay isn’t as good for farmhands as it is for graphic artists.”
“You’re a graphic artist?”
I took a sip of my wine, nodding. “Yep, it’s what pays the bills. I work for a small company that sells… well, it’s kind of embarrassing to tell to someone I don’t know all that well.”
“You can tell me later, then.” Evan looked amused at my hesitancy—you could almost say there was a mischievous twinkle in his eye as he said this. “Maybe over drinks and dessert at my place. I made a cheesecake in case you were willing to join me there.”
I was surprised to hear he’d baked it himself— didn’t he have a chef who could do that for him? “I can never turn down a good cheesecake,” I told him.
And so we ended up in his living room. It was humongous, sunken a few steps below the rest of the floor, with two long, black leather couches and four matching armchairs. We had sat together on one of the couches, and I was tucking into my first slice of cheesecake. I couldn’t help myself—when he’d asked me how much I wanted, I hadn’t been hesitant about asking for a big slice. He’d grinned when I told him that, and said he loved a woman with a good appetite. “Gotta take advantage of this great metabolism while it still works,” I had responded.
Now I only had one bite left on my plate, and once that bite was gone, I placed the empty plate on the glass coffee table which sat in front of the couch.
“Do you find me attractive?” Evan asked me. He moved a little closer, and moved his face closer, too—it was now mere inches from mine.
“Can I answer that question with a kiss?” I asked. My voice had become breathy, because yes, I did find him attractive, and yes, I was willing—and happy—to sleep with him.
“I think that would be lovely,” Evan said, his voice low and soft.
So I brought my lips to his, and there was our first kiss, and it was not long before I found myself growing very, very wet. Evan was an exceptional kisser, and his hands were skilled as well, skimming my arms with the lightest of touches, making me grow warmer and warmer between my thighs.
While I wouldn’t have minded fucking Evan right there on the couch, he went and suggested we go to his bedroom to shed the rest of our clothes. I was curious to find out what a millionaire’s bedroom looked like, and so I followed him down a long hallway to a large set of double doors. Once they were opened, I was unable to suppress a quiet gasp at the scene that was now in front of me.
… To be Continued!