Charley
“I want to see you tonight.”
It was a text from Harry.
Short, simple. The tone was impossible to identify. Should I be happy or worried? He had left so quickly this morning after my mother had interrupted us. He was probably disgusted that, six years later, Principal Pendleton was still interfering in his seductions.
While I debated how to respond, he sent another text: “Knowing you’re nearby is killing me. Dinner?”
“I could do that,” I thumbed back.
“8 o’clock? My resort has a good restaurant. I’ll pick you up in front of your hotel.”
“Okay. How dressy is your resort?”
Casual dress was common for most restaurants here, but he hadn’t actually told me the name of his resort, so I wasn’t sure what to expect. There weren’t that many on this side of the island. There was a new one a mile or so down the road, but it looked small and elegant and I wasn’t even sure if it was public.
“Cocktail dress casual,” was his response.
My mom was delighted when I told her I had a date. I had to confess that he was the guy from the plane, since she knew damn well I hadn’t met anybody else since we’d arrived. She still hadn’t remembered who he was, and I hadn’t volunteered the information.
She looked a tiny bit concerned. “He seemed a bit abrupt. How much do you know about him?”
“I’m sure he was just tired from the flight.”
“Well, if you’re sure…”
“Don’t worry, Mom. It’ll be fine.”
Harry
When I pulled into the circular driveway in front of Charley’s resort and saw her standing there waiting for me, wearing a short, low-cut, belted sundress, I got an instant hard-on. Holy shit, she looked good. Her cheeks were a little pinker than they’d been this morning—her arms and legs, too—she’d obviously been out in the sun today. The color made her big eyes look greener than ever.
She gave me her dazzling smile when I jumped out to open the passenger’s side door. “I was hoping you’d show up on a Harley.”
“Sorry, babe. Just one of the tiny island rent-a-cars. At least it has air conditioning.”
She climbed in, giving me a flash of leg, and I had to adjust my pants. Whew. Had I ever thought she was prim and innocent? I guess she had been, back in high school.
Her mother was nowhere in sight. Good.
I drove back to my own resort, which had an elegant restaurant and superb seafood. I tipped the maître d’ extra for a quiet table overlooking the ocean. As we devoured the tasty Caribbean food, we fell into a comfortable conversation, just as we had on the plane. Charley was bright, thoughtful and fun to talk to. We shared several interests, and our opinions on matters like politics and religion turned out to be similar. I could see myself spending time with her doing stuff that didn’t even require my dick to be hard and her legs to be spread.
On the other hand, my dick was perpetually erect around Charley, and my lusty brain continued to segue into thoughts of what I was going to do with her now that I had her here.
I knew what I wanted to do, but I wasn’t sure how to begin. She already thought I was a sex maniac, given the way I’d acted during my inglorious career as a teacher at her high school. Not to mention what I’d done on the airplane. And started to do in her room this morning.
I could easily get into a state where I thought of little else besides my dick’s happiness. I know they say most guys think about sex hundreds of times a day; well for me, it was probably thousands. My imagination had been humming all day with hopes, plans and fantasies about the various ways I wanted to fuck her before the night was over.
But not even I was stupid enough to blurt out, “Okay, dinner’s done, let’s go back to my room and fuck.”
I was pretty sure she’d say yes to me. The spark between us had ignited a blaze and I wasn’t the only one getting scorched. Her lips parted softly whenever she looked at me and her cheeks kept flushing. I knew that if I reached out and stroked her breast, she would lean into me. If I dipped a finger between her legs, she would be wet.
So it shouldn’t be difficult. Just take her outside for a walk, slip her hand into mine, pull her into the shadows for a kiss, and guide her down the path to the room that was waiting for us: my room, where I’d been envisioning her ever since I’d checked into the place.
So why was I hesitating? I was 99 percent sure she wanted it too.
When she was a high school kid, Charley had seen my dick pumping into some other woman’s mouth. I don’t get embarrassed easily, but what must she have thought of me then? I hoped it hadn’t been something she’d never seen before. Or done before. She’d been a senior. Surely she’d had sex? Girls had sex in high school, right? When I’d been a high school kid, girls had had sex with me.
But Charley had always seemed so naive. If I’d been caught by any other chick in her class, I wouldn’t have been so floored, but somehow the idea of the principal’s daughter watching me get a blowjob had freaked me out then and was still freaking me out a bit now.
Get over yourself, dude. She came on your fingers on a plane.
“It’s a beautiful night,” she said when I continued to stare at her in silence. “Maybe we could go for a walk on the beach?”
“Sure.” I tried to snap out of it. We could stroll in the direction of my room. Charley was getting fucked tonight, one way or another.