Charley
I swore to myself that I would not feel as if I was doing the Walk of Shame the next day when Harry dropped me off at my own resort. My mom was on the pier. She liked to go down there to watch the daily noon-time feeding of the fish. A worker from the resort was flinging bread crumbs to the fish who milled around there. Even though bread was not the food of choice for fish, they always attacked the stuff with enthusiasm. I guess it coaxed all those mighty schools of fish to live in the coral reef near our dock, and that pleased the tourists!
Mom was pretty chill about my absence last night. All she did was cock her eyebrows and ask, “Do did you have a good time?”
“I did.”
“Going out again tonight?”
I searched her words for…I don’t know…disapproval? Curiosity? Snark? But there was something else there. I frowned at her, puzzled. My mom and I can read each other pretty well.
“I think so.” Actually I knew so. Harry had said he’d pick me up at seven. He’d tried to convince me to spend the rest of the day in bed with him. I wished I could have done so, but Mom and I had a snorkeling trip scheduled. “Is that okay with you?”
“Sure. Actually, I have some plans of my own this evening.”
“Really? What’re you planning?” The resort was advertising a karaoke sing tonight. Maybe she wanted to go to that? Had she been hoping I’d go with her?
But she blushed. I blinked in surprise. My mother actually blushed.
“I’ve been invited out to dinner.”
“Who with?”
“While I was walking in the surf yesterday, I met a very nice man. His name is Tom. He’s staying at that other timeshare place down the beach. We chatted for quite a while and had a drink together. While you were out. I liked him. So when he invited me for dinner this evening, I said yes.”
My eyes must have been bugging out of my head. My mom was going on a date? My dad had been gone for four years and I was pretty sure she had never done that before.
“You don’t mind, do you?”
I realized she was much more anxious about what I might think of her date than I’d been about how she might regard mine. I’ll admit it gave me a jolt to picture Mom dating. She wasn’t planning to have sex with this guy, was she? Oh my God. Perish the thought.
“No, of course not. I’m just surprised.” I felt protective. “Who is this guy? Tom What? How much do you know about him? I mean, how do you know he’s, not, like a creep or something?”
Her eyes crinkled and she laughed out loud. “Hey. Who’s the mom around here, Charley?”
I had to laugh, too. “Well, just be careful, Mom. It’s been a long while since you’ve been out there.”
“I know. I’m so nervous. Come back to the room with me, okay? Help me figure out what I’m going to wear.”
“Sure. But—” I hesitated. “I don’t want to know anything that happens on this date of yours, okay? I mean, afterwards. You’ve got your phone, right? Call one of your friends back home if you need to share. Because, you’re, like, my mom.”
She laughed at me again. “I’ll tell you just as much as you ever tell me about your men. How does that work for you?”
Since I hardly ever told her anything about that stuff, it worked fine. I certainly didn’t want to talk to her about Harry.
If he and I kept seeing each other, though, I would have to tell my mother sometime. And that was going to be awkward.
Chapter Seventeen
Charley
Our vacation was going much too fast.
I was spending time with Harry every day and sleeping in his bed at night. It was a good thing I’d gotten such a bargain on my room, since I was hardly ever there. When we weren’t enjoying the beach or the water, we were lounging with a book or some music in a deck chair, or hanging out at his resort bar, chatting with the other guests and the friendly staff. It was so relaxing.
Harry and I went snorkeling and scuba diving. He drove me all over the island in his rental car. We took a sunset cruise on a catamaran with reggae music and plenty of pina coladas. We went to swim with the stingrays, fed them and petted them as if they were puppies.
We both loved to swim and we were intermediate-level divers. Grand Cayman has some of the most beautiful reefs in the Caribbean, so both sports are amazing there.
Just being with him was great. He made me laugh, he was super-smart, and for all his rakish bad boy elements, especially in the bedroom where he was deliciously inventive, he was, at heart, a really sweet guy.
But there was one puzzling thing about him. Every time I’d tried to learn what Harry did for a living, he’d ducked the question. I’d soon heard more about my mom’s hookup Tom’s career as an investment banker than I had about Harry’s occupation.
I’d probed gently a couple of times, but I hadn’t wanted to push it. He’d been fired by my mother. Given the circumstances of that dismissal, it must have been tough for him to ever get another teaching job. Had he been forced to accept some job that he hated? Or maybe even something that he was ashamed of? If he didn’t wish to tell me, I figured I didn’t have the right to pry.
As for Mom’s summer romance, I could hardly fail to notice that her bed hadn’t been slept in lately, either. She must be spend her nights with Tom.
When I wondered aloud whether I’d still be having sex at her age, Harry laughed at me. “Your mother isn’t old, Charley. What is she, in her mid-fifties or so? Some people still have sex well into their eighties. I had a great-uncle who lost his wife when he was seventy-something and remarried at 81 to his old high school sweetheart. She had married some other guy. When they both ended up widowed, they found each other on Facebook and hooked up again.”
“Really? That’s so romantic. Must be true love.”
He’d grinned and kissed me. “I love the idea of finding someone from years ago and getting a second chance.”
“It’s not as if we ever had much of a first chance,” I laughed.
“True,” he said, kissing me deeply. “I don’t know about your mom, but for me, this isn’t just some hot summer hookup, babe. I want to keep seeing you when we get back home. That’s my plan for us, anyway.”
I knew now that Harry lived not far from me in the suburbs of Boston. I was going to be teaching at Rolling Meadows Regional High School and he lived in the neighboring town of Cranton, close to Penshurst College. It could hardly have been any more convenient for us.
“Do you still have that Harley, by any chance?”
He gave me a wicked grin. “You bet I do, doll.”
“Then your plan works for me.”
Chapter Eighteen
Harry
It was our last weekend on the island, and I figured it was up to me to resolve the unease that Charley was still feeling about her mom and me. She obviously didn’t want us to meet, although I think her concern was for my sake, not her own.
But I was okay with what had happened. The anger I’d felt at the airport when I’d realized I was face-to-face with my former boss had cooled. I was a few years older now, and a lot more mature. I’d fucked up. I didn’t bear a grudge.
Besides, I was going to have to meet Adele again sometime. She and her daughter were close. This thing with Charley was working. Even though we’d only spent a little over a week together, it had been fantastic, and I don’t just mean the sex. She and I fit together in all sorts of ways. I could imagine the future stretching out in front of us. No matter how I looked at it, I liked what I saw.
When I went to get my girl that evening at her resort, I showed up early, parked in the lot out front, and walked around the building to the beach side where her mother’s timeshare was.
Charley’s mom was outside on the condo’s patio arranging tropical flowers in a vase. There was a big orange cat prowling around, tail high, with two kittens prancing behind her. I noted a saucer on the patio. Like many of the resort guests, Adele must have been feeding the local felines.
She
looked up as I stopped on the path beside her glass-topped patio table. “Beautiful flowers,” I ventured.
“They are, aren’t they?” She smiled and nodded at me. The first level of recognition dawned. “Oh. You’re here for Charley? I saw you at the airport…” her voice trailed off. Another level must have kicked in. “Wait. I know you, don’t I?”
I held out my hand, which she took automatically. “You knew the man I used to be. The kid, actually. Harry MacCallum. I worked for you once. You fired my ass.”
“Harry MacCallum. No wonder you looked familiar. Wait. So you and Charley—”
I nodded. “Yep. But I swear, I no longer do the wild and crazy stuff I was stupid enough to pull at the age of twenty-three.”
She put on her severe Principal’s face. “I certainly hope not.” But then she softened and grinned at me. “You were the talk of the faculty lounge for quite some time, Mr. MacCallum. Lucky for you, there was no video. If there had been, you might have ended as a social media sensation.”
No, dammit, I didn’t blush. I have a little sunburn, that’s all.
“You and my daughter met on the plane? And she gave you a false name?” She was rapidly assembling the pieces. “Then at the airport, when you saw us together, you realized who she was and who I was and—”
“Yeah. Sorry for being rude. It was a bit of a shock. But I’d always liked your daughter—well, that’s not to say—I didn’t go after students back then, no matter how reckless I was in other respects.”
“I know, Harry,” she said tolerantly. “Believe me, after what happened I had a lot of uncomfortable discussions with the staff. If you’d been messing with students, I would have heard about it.” Her eyes twinkled the same way Charley’s did. “Believe me, I heard all about your antics.”
I seriously doubted she’d heard all. But there are some things that are best forgotten. “I’ve changed. I’m a responsible citizen now.”
She rolled her eyes. “You were quite the player a few years ago. Am I supposed to be happy that you’re playing around with my daughter? Is this just one of those hot vacation flings?”
Just then, the sliding door opened and Charley, looking amazing in a bikini, stepped out onto her mom’s patio. “Harry? You’re kinda early.”
“I wanted to meet your mom.”
She was blushing in that cute way of hers. She looked back and forth between her mother and me. I could tell she was reading the situation, and, as usual, she read it well. She propped her hands on her hips and gave me a mischievous look. “Well? Answer the question, Mr. MacCallum. Is this one of those hot vacation flings?”
She already knew the answer to that, the little minx. Right in front of her mom, I grabbed her wrist and jerked her into my arms. “No way, girl. This is something special.” I kissed her on the forehead and then tucked her against my side. “No one’s firing me this time. This time I’m here to stay.”
Chapter Nineteen
Charley
On my last night on the island, which, sadly, was one night before Harry’s last night, he took me for dinner to a restaurant where there was a large dance floor. At what must have been a prearranged signal from him to the DJ, they started playing Don’t Stand So Close to Me. Harry had a mischievous look on his face when he insisted we dance.
“I have a little surprise planned,” he whispered, holding me close as we swayed to the music.
“I love surprises.”
“I don’t honestly know whether you’ll love this one,” he said, his blue eyes gleaming wickedly.
When we got back to his hotel room, he’d no sooner shouldered open the door before his hands were all over me. “So, I have to go back to work soon, and I need to do a little research.”
“What sort of research? Are you finally going to tell me what kind of work you do?”
“I will tell you, yes. After the research. Don’t know about you, hon, but to me there’s something irresistible about the forbidden schoolgirl fantasy.”
I laughed. “Well, from my perspective it’s the forbidden teacher fantasy, but, yes, I agree.”
He took a large cardboard box off the table and handed it to me. “Go into the bathroom and put this stuff on for me.”
Lingerie? Sexy undies? I pulled the top off the box and separated the tissue paper. I lifted out a navy blue garment that puzzled me for a moment. A short pleated shirt? There was a white blouse and something that looked like a feminine necktie and blue knee socks. A uniform? A schoolgirl’s uniform?
I didn’t see any undergarments.
“What exactly are we researching, Harry? Please don’t tell me you’re a porno movie producer.”
But as soon as I said that, I thought, shit, what if that is what he does? “I mean, it’s fine…I don’t care what you do for a living. Porn entertains a lot of people, so it wouldn’t be a problem—”
I glanced quickly around the room, looking for a camera. Thank goodness I didn’t see one!
Harry was laughing at me now. “No, I don’t make pornos. Go put that on.”
I shook out the clothes. “Where on earth did you get this?”
“In some of the schools here on the island, they wear uniforms in the old British style. Not designed for mature figures, but I think it’ll fit you. I picked out a shop-girl who was about your size and made her try one on.”
“I’ll bet you did,” I laughed.
“There’s even a hair ribbon so you can tie your hair back in one of those cute ponytails.”
“Okay, but what about you? You don’t exactly look like a British schoolmaster in your shorts and T-shirt.”
“Go change, little lady, and when you come out, you’ll be properly disciplined for that remark.” He opened a dresser drawer and withdrew one of those wooden rulers. He slapped it into the palm of his hand and quirked his eyebrows at me. “This is an old-fashioned establishment. Not at all like a public high school. We have rules. Pupils do not talk back to the schoolmaster. If they do, they suffer the consequences on their lovely round bottoms.”
Oh dear. Bad Prince Harry was back after all these years. I swept up the box and headed for the bathroom. What a devil. I was totally turned on.
Harry
Charley looked scorching hot when she came back. I’d never actually seen a schoolgirl in a uniform, having attended and taught in public schools, but this was a sensual dress-up thing, and I was grateful that Charley was willing to have fun with our sex life.
I was definitely thinking of it as “ours” these days, which was quite a change in my worldview, and entirely due to her. Thinking back on it, I couldn’t believe I’d spent as long as I had with Portia, my ex, who had hardly ever cracked a smile. Charley could be serious, but she also had a playful spirit that I adored. It was if she’d carried a little beam of sunlight with her wherever she went.
She had a huge irrepressible smile that reminded me of the young Julia Roberts. When that grin materialized on her face, it filled me with joy.
I didn’t actually have a costume, so I’d just slung a tie loosely around my neck and torn off all my clothes.
“That’s not very school-masterly, she teased when she sashayed out of the bathroom in her outfit.
“This is the school-masterly part,” I said, brandishing my ruler. “Come here and spread your bottom on the bed, you naughty girl. I’m going to wallop your ass for not doing your homework.”
“No way! I always did my homework. I was such a good girl.” She paused, grinning, “And you were such a wicked, Harley-riding boy. Bad Prince Harry. I still think of you that way.”
“Yeah? Better bow down to your high and mighty royal lord, then, babe.”
She held the pleats of her ridiculous skirt out to the side and curtseyed. She did it quite elegantly. Then she strolled to the bed and stretched herself out on it. She was lying on her tummy. My cock throbbed with anticipation.
I went to the side of the bed and flipped up the back of her shirt. No underwear. I loved her rounded as
s. I’ve always been something of an ass man.
But it would be hard to find any part of Charley that I didn’t love.
She pressed herself up on her elbows and shook her head. The pony tail whipped back and forth. She wriggled her ass for me. “I dare you, Mr. Schoolmaster. I’ve always wondered what if would feel like to be spanked with a ruler.”
“Wonder no more,” I said and gave her what probably didn’t amount to more than a light tap. Charley liked it kinky, as did I, but I didn’t want to hurt her.
I smacked her again. She squirmed in a very appealing manner. “Hmm. I think I can get into this impact toy thing, Mr. Schoolmaster. Maybe we can order a flogger when we get home. Do it again.”
I did it harder, which made my cock happy. I wasn’t sure about the ruler, though, so after using it a few more times, I tossed it on the bedside table and spanked her with my hand instead. After about a minute of this, my hand was sore and her bottom was red. Her moans and her squirms had escalated, as had my arousal. When I slipped my finger in between her legs, her pussy was drenched.
She rolled over onto her side and grinned up at me. “I’m beginning to see why so many schools banned this corporal punishment thing. I could feel every single blow in my clit. I think I might be able to get off with erotic spanking alone.”
I fell on the bed beside her. “You’re a lovely little discipline freak, aren’t you?”
She giggled, stroking my hard and heavy dick. “And I knew you were bad to the boner.”
“Don’t make me laugh,” I protested, chortling. “It’s a good thing I never got my hands on you when you and I were student and teacher, or your mom would have had a much better reason to fire me.” I kissed her mouth and felt her slide her tongue against mine. We rolled on the mattress, her legs widening to let me rub my pelvis against hers. She already felt so dear and so familiar to me, after the past few days of frequent lovemaking. My dick always seemed to be stiff around her, my whole body ready to claim her, establish and re-establish possession.
