tagMatureTeaching Kaylea

Teaching Kaylea

byBuckyDuckman©

"My mom's convinced I won't graduate without getting pregnant," Kaylea told me, tucking in her shirt before tying her apron around her waist.

"There are ways to make sure that doesn't happen," I joked. She rolled her eyes at me. "I'm serious, Kaylea."

"I know," she said. "I'm careful. I won't get pregnant, Tim, I promise."

As her boss instead of a teacher or parent, I knew I could say things to her other adults couldn't. "Famous last words of eighteen year olds everywhere," I teased right before adding the words I never should have said. "Tell you what, graduate without getting pregnant and then I'll give you the education high school boys can't give."

"I don't know, some of those high school boys are very educational." Kaylea Nolan flashed me a big smile.

"Uh-huh," I agreed, unable to hold my tongue. "I thought the same thing when I was your age until I met Claire."

"That old woman who comes in here every Wednesday? How old is she? One hundred?"

"She's pushing seventy, but twenty-five years ago, she was thirty-eight and I was eighteen." I didn't explain anything more. Kaylea clocked-in and made it halfway around the sales counter before she stopped, turned and looked at me with wide eyes.

"Wait, you're saying you did her?"

I laughed at how long it took Kaylea to realize what I had said. "More like she did me."

"Wasn't it gross?"

"Not then. Twenty-five years ago, she was hot as hell." In my mind, I flashed back to when I was a cocksure and nervous eighteen year old being seduced by a woman more than twice my age. She taught me things about how to please a woman I will never forget.

"How old are you again?" Kaylea asked.

"Thirty-eight," I joked. Actually, I'm forty-three, but Kaylea wouldn't know the difference and I'm still stinging about turning forty anything.

"You're almost as old as my dad!" she said. "And he's like forty-three or something."

"Get to work," I told her, ending the conversation for three months.

After a wetter than normal spring, the end of May brought hot, sunny days that foretold a scorching summer. Kaylea needed lots of time off, first for prom, then a senior trip to Europe and finally for graduation. "Feels weird thinking I'm done with high school," she said on her first day back since the beginning of May. She looked rested and still sported prom's fake-bake tan. "So, when are we going to do it?"

"Do what?" I asked, busy counting down a cash drawer.

"Don't you remember? If I graduated without getting pregnant, you were going to give me a real education."

I laughed and kept counting down the cash register, trying to figure out why I had five dollars too much.

Kaylea slid up close to me. "I'm serious," she said, running a finger across my bicep. "I want my lesson."

Figuring out the bothersome miscount felt like a victory. I slapped the drawer shut, victorious once again and smiled down at Kaylea. She was so short compared to me. I nearly made a joke about how she wouldn't be able to handle a real man like me but she wore such a sincere and hopeful look that I paused as I gazed into her green eyes. She smiled. Since her braces had come off, she smiled a lot.

"Please?" she asked and I couldn't doubt her sincerity.

"Three o'clock on Thursday," I said. She gave me a puzzled look. "That's when I'll wait exactly five minutes in the parking lot behind the store. If you're serious, get in my car and we'll do something."

"I don't want to do something, I want to do everything," she smiled.

"Three o'clock. Thursday," I repeated before heading to my desk. That gave her four days to think about it.

I didn't expect her to show. Either way, I had made a reservation at nice hotel near the airport. I checked into the hotel before heading to the shopping center. Employees are expected to park behind the building and it wasn't uncommon to see a car parked there overnight. I pulled into the parking lot precisely at three o'clock. Kaylea sat in her car waiting. She wore a big smile as I pulled into the space next to her. She moved from the driver's seat of her car into the passenger seat of my car. She carried an overstuffed backpack and put it between her feet. "I wasn't sure you would show," she grinned.

"A deal's a deal," I smiled, backing out of my space and heading to the hotel. "Nervous?"

"A little," she admitted. I was quiet for a moment as I negotiated afternoon traffic and she filled the space. "Just so you know, I'm not a virgin. I've done stuff. Lots of stuff."

"Okay," I said, willing to let her talk.

"And I'm on birth control, so you can't get me pregnant. Mom made me get on birth control so I wouldn't. . . well, you know."

"Get pregnant before you graduated," I said.

She smiled, nodded and put her tiny hand on my thigh. "I'm glad I didn't so we could do this."

It was a short drive to the three star hotel. We crossed the lobby to the elevator. The staff ignored us. It wasn't until the doors closed to the glass enclosure that I realized we were really going to do this. Until that moment, it had felt like a fantasy, a tease between a teenager with overactive hormones and her much older mentor. For the first time, I worried I could live up to my hype.

At forty-three, I didn't feel old, but I couldn't feel young anymore, either. I had been an athlete in high school, but high school had been a very long time ago. Longer than Kaylea had been alive. I pushed that thought away and reminded myself she was eighteen and completely legal. She was only a couple years younger than the girls at the strip club I sometimes visited. I wasn't in great shape. Middled aged spread was beginning to show around my midsection. I pushed away my concerns. If it didn't matter to the strippers, why should it matter to her? I led the way to our room, pushed it open and allowed her to enter first. She was impressed.

"Wow, nice!" she said, immediately inspecting every corner of a room that included a small sitting area, a square coffee table, and a very big flat screen TV. The big kingsized bed sat around a corner. The bathroom included a separate shower and a deep tub lined with jets. She inspected the wet bar. I shook my head when she asked about the tiny bottles of liquor but allowed her to have a Coke.

She turned on the TV and scrolled through the pay-per-view offerings. "Can we buy some porn?" I travel often enough to know how the adult pay-per-view channels worked. We bought the unlimited block of 24 hours that would allow us to watch any of the adult movies. The dollars were adding up and I didn't care. She picked a random movie and I turned off the sound. Is there anything worse than the soundtrack of porn?

"Should we get naked?" she asked, filled with more energy and excitement than I expected. She fluttered around like a caged hummingbird. I realized she was nervous and I needed her to calm down.

"Let's slowdown," I smiled, taking her hand and leading her to the window. We were on the tenth floor facing the city. The bright afternoon sun glimmered off windshields of tiny cars below. Fluffy white clouds dotted an otherwise blue sky with gravity defying ease. I stood behind Kaylea and put my hands on her shoulders, keeping her in place with a light touch. I waited a long moment. She looked up and over her shoulder at me. I gave her a smile. She stared out the window and quieted. I caressed her deep ruby red hair, the color she had wanted for prom and decided to keep for now. "Is it okay if I touch your breasts?"

"Yes," she said and I could see the faintest ghost image of her reflected in the glass. She was smiling. I could guess the question felt funny to her and that was okay. I slipped a hand over her shoulder and across her breasts, gently caressing her chest without grabbing or clutching at her while I memorized the feel of her young tits. She was wearing a thin bra. Her nipples weren't hard, not yet. Her tits had the resilience of youth. I caressed her shoulders and neck, too, careful to pay attention to more than just her tits. "That feels good," she softly said.

"Everything I do will feel good," I promised, kissing the top of her head and inhaling the sweet, flowery scent of her hair conditioner. I took a deep, calming breath. I needed that to calm my beating, pounding heart. Touching Kaylea's tits had made what we were going to do very real for me. I ran both hands in front of her, cupping her breasts and gently massaging them. "Do you masturbate?"

Kaylea giggled. "Do you?"

"Yes," I said and waited for her answer.

"Sometimes," she said, her voice small and quiet. I could tell it embarrassed her admit something so private.

"Do you ever use toys when you do it?"

"Just my fingers," she sighed. I found her nipples and gently rolled them between my fingers and thumbs.

"When was the last time you did it."

Kaylea was quiet for a long moment. I moved my hands away from her hard nipples and breasts, once more caressing her pretty hair. "Last night," she finally revealed.

"Did you have an orgasm?" I asked, moving my hands back to her tits.

"I think so."

"You don't know?"

"I mean, I guess I did. It feels good when I do it and then it feels really good before I sort of stop."

"You're stopping too soon," I said, kissing the top of her head. "Have you ever had an orgasm?"

"Maybe. Once."

"I'll change that today if you'll let me."

"Promise?" she asked, looking up at me again.

"It's up to you," I said. "Can I take off your shirt?"

"Yes," she said, turning back to stare out the window. When I pulled her t-shirt up and over her head, she moved her arms automatically, allowing it to happen without helping. The cups of her thin bra were lined with twin rows of lace and I could guess her panties would match. I asked for permission before undoing her bra. Her tan never stopped.

"You're beautiful," I whispered, careful not to press against her back as my cock began growing firm inside my pants. Pulling her hair to one side, I kissed her neck. She inhaled sharply. I kissed her neck again.

"This is a nice room," she said though she was still facing the window and the view of a day that unfolded in miniature beneath us. I kissed along her shoulder a few times while caressing her chest and feeling my cock swelling until I was completely hard.

"Will you get naked for me?"

"All the way?" she asked, as if there was another way to be naked.

"Yes," I whispered in her ear before kissing just behind and beneath it. She undid her shorts and wiggled her hips as she peeled them off her body and revealed her matching panties. She glanced over her shoulder at me before hooking her thumbs inside the elastic band circling her lower torso.

"Why am I getting naked first?" she asked, hesitating.

"Because I asked for it," I said. I lowered my head and kissed her lips. "Either you trust me or you don't."

"I do," she said right before peeling off her panties. She stepped out of them and tried to turn around. I pulled her against me, preventing her from doing it. My hands were on her bare breasts. "Will you get naked, too?"

"In time," I said.

"Do you think anyone can see us?"

"Only if they have a helicopter," I said, caressing her flat stomach. She reached between us. Her hand cupped my crotch and she felt my hard-on.

"You feel good."

"You feel better," I said. Our height difference limited my reach. I hunched over, running my hand farther down her flat stomach until I brushed across her pussy. I didn't try to finger her, I only caressed her. "You're shaved."

"Waxed," she corrected. "Brazilian. For you." I wasn't sure I believed she had done it for me but didn't challenge her on it. I ran my hand around her hip and caressed her firm, pert ass.

"Brazilian means they waxed back here, too, doesn't it?" I asked, checking what I believed to be true. She nodded. "Have you ever done anything back here?"

"I tried it. Once. It hurt, a lot."

"Is that something you want to do?"

"Do you?" she asked, looking at me again. I kissed her again. Her full lips felt good against my lips. I could tell she wanted a deeper kiss. That would happen, but not yet. I pulled away, still raking my hands across her naked body with one hand on her front and the other along her back. I didn't focus on her tits and ass but I didn't ignore either place, either.

"We can do that if you want and I will make sure it doesn't hurt."

"Do other girls do that?"

"Some do," I said, enjoying how eagerly she rubbed and caressed the swollen bulge inside my pants. When was the last time I had felt a woman rubbing me with such eager zeal? I couldn't remember. Was it a function of age? When I was eighteen, was I all about grabbing the most important body parts first? As best as I could remember, that's precisely how I had been. I accepted her clutching grab as a sign of desire. She wanted my dick and, in time, I would give it to her, just not quite yet.

"I want to do everything," she said. I reward her with another kiss.

"I'm going to give you an orgasm," I said without considering how difficult or practical of a statement I had made. "I'm going to do it right, right now, with you facing this window. All you have to do it let it happen."

"H-how will I know when it does?"

"Trust me, we both will," I told her, caressing her breasts again. Her nipples were two tight pebbles between my fingers and I rocked them to side. "But you have to help, too. You have to tell me what feels good and what doesn't feel good. Promise?"

"Yes," she agreed, squeezing the lump inside my pants. "Is it okay if I keep doing this?" I told her it was as I hunched over and slipping my hand farther down her front. I had brushed over her smooth, waxed pubic area several times. My hand shouldn't feel like stranger there.

"Are you wet yet?"

"I think so."

"Let's find out," I said, slipping my middle between the puffy, swollen lips of her pussy. I instantly felt her warmth and how slick she felt. "Mm, you're really wet," I whispered against her ear.

"That's a good thing, right?"

"A very good thing," I assured her, playing with her smooth outer lips.

More years ago than I cared to remember, Claire had taught me how to play with a woman's pussy. "Don't just go shoving your fingers up inside of her all willy-nilly," Claire had instructed. "No woman will like that. Treat it like an inside out dick. Caress her. Play with her. Make her want more." I had used her advice for years with great results.

I lightly caressed between Kaylea's pussy lips, gently exploring the territory. She made a soft gasping sound when I brushed over her clitoris. "That's your clit," I told her. I circled around the sensitive spot, analyzing her reaction. I knew some women enjoyed more direct contact that others and I needed to figure out how Kaylea was wired. "Is that where you touch when you're doing it yourself?" Her answer surprised.

"Usually I, um, touch lower. Inside. Like when someone is fucking me."

"You mean like this?" I asked, pressing my one finger part way inside her pussy. I stopped at my second knuckle, far enough inside that I was finger fucking her without pressing too deep or hard.

"Yeah, like that," she sighed.

"What about here?" I asked, caressing her clitorial area again. "You touch here, too, don't you?"

"Not so much," she said over her shoulder, as if checking to see that she was giving good answers. I gave her a reassuring smile, kissed her once and touched the outside of her lips with my tongue. I felt her lips parting, wanting my tongue. I didn't give that to her. Not yet.

Kissing is a tease, too, Claire had taught. She told me I shouldn't try to tongue-fuck a woman's mouth the moment our lips met any more than I should try finger-fucking her the first time I touched her pussy.

"Next time, spend more time touching here," I said, circling her clit. "This is the important spot, not deep inside yourself."

"That feels really good."

"It's going to start feeling even better. Just go with it."

"Okay," she murmured, leaning backwards against me and I knew she trusted me. I played with her tits, enjoying the feel of her stiff nipples with one hand while caressing her sex with my other. I experimented with up-and-down motions on her clit and side-to-side motions. When I went up-and-down, she subtly moved her hips side-to-side. When I went side-to-side across her clit, she wiggled back and forth a bit. I figured out what that meant and went back to doing circles and that locked her hips in place. "Fuck, that feels so good."

I moved my finger a little faster, zeroing in on her clit and pressing harder against it when I felt her pressing harder against my finger. "Do it," I whispered. "Come for me."

"Uh-huh," she groaned.

"Don't force it, just do it," I coached.

"Finger me," she gasped and I knew she was asking me to finger fuck her again.

"No, like this," I insisted, unable to resist a smirk that she caught. "This is all you get until you cum."

"I want it inside," she begged.

"Good," I replied and gave her something more. It wasn't what she requested or expected, but it was what she needed. I added my ring finger to my caresses of her clit. Holding both fingers tightly together, I squished against her clit and dug in as I rubbed. Some girls like it firmer, some didn't. I knew which one Kaylea was.

"Ooo . . ." she groaned from deep inside her body as her orgasm neared. "Ooo!" her cry grew and I knew she only seconds away. "OOO!" she called out as her first real orgasm clutched her body. She bucked backwards against me, pressing her entire back against my front for support as she fought against trembling knees she couldn't trust. She doubled over and would have bounced her head off the window had I not been holding her chest, too. She came, thrashing and bouncing with each pleasurable surge coursing through her body until she shuddered and was done. "Oh fuck," she said as a finishing statement and shivered once more before I felt her standing firmly of her own free will.

I don't know why I did what I did next. I'm going to claim it was because I was drunk with the lust of the moment. Hell, I don't know why, only what i did. I shoved my two wet fingers inside her mouth. "Suck my fingers clean," I hissed in her ear. She didn't argue, she just did, sucking and licking my fingers with glee until I pulled them out.

"Does that make me lesbian?" she asked.

"Not yet," I laughed. "Did it taste good?"

"Am I lesbian if I say yes?"

"No, you're you, that's all," I assured her, already knowing the answer. She lightly leaned against me, still facing the window.

"That felt really good."

"I bet."

"That's never happened to me before, not even when I do it myself."

"It's going to happen to you a lot today."

"Promise?" she asked, looking over her shoulder at me.

"Promise," I said and this time when we kissed, I allowed her to feel my tongue against hers. She turned to face me and we kissed in front of that window for a long time. I finally pulled away and smiled down at her. "Ready for lesson number two?"

"Are you going to get naked for this one?" she asked.

"Yep. Now it's time for you to give me an orgasm."

"Do I get to blow you? I'm really good at that!" she said with excited eagerness of youth.

"Do you swallow?" I asked.

"Always," she grinned as her tiny fingers began working the front of my pants.

"Whoa," I said, stopping her. "Let's get comfortable first." I took her by the hand and moved to the small seating area in front of the big TV playing porn. I don't remember what was playing on the TV, only that some guy and some hot chick were naked and having sex. Compared to the naked nymph in front of me, it didn't matter what the paid performers on screen were doing. I sat on the couch and considered slowing her down as she pulled open my pants. I considered the value of a lesson about blowjobs and gave up on it. She was too eager and I was too excited. I allowed her to pull off my jeans and underwear, baring my long, hard, excited cock to her.

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