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Teaching Kaylea

Category: Mature
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“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.

“Damn,” she cooed as it sprang into view. “If I knew you had one like this, I would have been blowing you at work months ago!”

“Okay Miss-Know-It-All. Impress me.”

“Easy-peasy,” she giggled, settling on her knees between my legs. “I have sort of an oral fixation.” She licked up the length of my cock, maintain eye contact the entire time. “And I’ve watched a lot of porn girls doing this.” She opened her mouth and wrapped her lips around my aching cock. As soon as I felt her tongue flickering against the underside of my cock, I knew I had stumbled upon a woman who didn’t tell lies about her cocksucking abilities.

I marvelled at Kaylea’s oral abilities as she kept her pretty green eyes on me and worked over my hard cock with her mouth, lips, and tongue. Her skill was unmatched as she used her tongue, never once snagged me with a wayward molar, and came damn close to deep-throating me. She used her tiny hands around my knob and to fondle my balls as she coaxed me brought me closer to an orgasm that rose too quickly inside of me.

There was no way for me to slow her down or slow my rapid ascent to my orgasm. I didn’t try holding back. Instead, I stroked the side of her face, cooed sweet nothings at her about how good it felt and enjoyed her skill until I reached my peak. My heart raced with excitement. Gasping, I came, trusting she wasn’t lying about swallowing. The moment my orgasm began splashing against the back of her mouth, she moaned, swallowed and pumped me hard for the rest of my creamy delight. I embraced my orgasm, allowing it to flow from me and into her with unbridled passion as I moaned her praises.

“Told you,” she giggled, squeezing out one last droplet and licking it up.

“Amen,” I agreed, smiling so hard it hurt it my cheeks. “Guess that’s one lesson you won’t need.”

“Can you do that thing to me again and make me cum?”

“Trade places with me,” I said, pulling her up on the couch. “It’s time for you feel how a real man eats pussy.”

“My boyfriend does this all the time,” she giggled, slouching on the couch with her legs parted and ready for me.

“Except he doesn’t make you cum when he does it,” I reminded her.

“I come close,” she insisted.

“Close doesn’t cut it,” I said, leaning over and kissing her tits for the first time. I spent a couple long moments on her chest, appreciating her youth and the firmness of her nipples. I captured one between my teeth and flicked my tongue across its tip.

“Oh wow,” she purred. “That’s different.”

“That’s why we’re here,” I reminded her before doing the same thing to her other tit. I kissed down her flat, tanned stomach and right before pressing my mouth against her pussy, I put her thighs on my shoulders. She giggled again. I guess she liked that idea. Finally, I held her pussy lips apart and licked her for the first time.

She tasted as sweet and innocent as she looked and I was instantly hooked on eating her pussy. I buried my face against her pussy, rapid firing my tongue over and around the lovely little bump of her clit. “Oh fuck!” Kaylea squealed, surprised and I knew her boyfriend had no idea what he was doing whenever he went down on her.

I pressed my tongue against her clit and did circles that delighted her. I teased her by pulling away and listening to her groan when my tongue left its target. Claire’s instructions again echoed in my mind through the years as they had so many times in the past. Claire had made it clear that eating pussy meant teasing it first. I sucked on Kaylea’s labia, first one half and then the other side. I pressed my tongue inside her vagina as deep as it would go before licking her clit again. She squirmed and I knew all I needed to know before I surprised her.

“Were you serious about that other thing?” I asked, looking up at her with my cheeks and chin wet from licking her.

“Which thing?” she asked. I cupped her ass with both hands and lightly brushed against her tight, puckered asshole.

“This,” I reminded her. “Do you trust me?”

“Yes,” she quickly said though she looked nervous.

I pushed her knees closer to her chest, rolling her into a ball and exposing that cute, puckered butthole to me. I spat on her asshole, rubbed my thumb against it and, watched her eyes go wide, at first with shock and then with surprise as she realized how good it could feel. I didn’t overplay my visit to her backside. I only did it enough to tease before moving my mouth back to her clit.

Back to licking her clit, I never forgot that I had two hands or fingers. I played with her tits with one hand while rubbing her pussy with my other hand. I teased the opening of her vagina with a finger, pressing my finger inside of her as far as a single knuckle and caressing the sides, bottom and top. Then I put two fingers part way inside her pussy, splayed and rotated them. Fuck, she was tight. Would she ever be able to handle my big cock? I teased her pussy some more as I ate her, waiting and watching as her orgasm grew closer.

Her breathing went shallow. She tried wiggling her hips and felt the pressure of her thighs against my shoulders. I pressed harder against her clit with my tongue, lashing at the tiny nub and I didn’t stop until she went tense for a moment before thrashing with her second, real orgasm. She bucked up and down and my tongue rode her clit through-out until she relaxed.

“Guess that doesn’t happen with your boyfriend,” I said, looking up at her.

“No,” she gasped, still breathing hard.

“Or this,” I said, lowering my mouth back to her clit.

“Oh fuck!” she cried out, squirming as if she was trying to pull away before giving up and giving herself over to me. That’s what I wanted and a few moments later, she was having another orgasm. “I didn’t know I could do that!” she gasped when it had passed.

“That’s why we’re here,” I said and lowered my head to her pussy a third time. It took only moments and fewer than before. She came again. “Should I keep going?”

Kaylea shook her head. “I can’t breathe,” she said, sucking in lungfuls of oxygen. “You’re killing me.”

“It’s what I do,” I said, brushing against her sensitive clit with my thumb and laughing at how she squirmed before I pulled away. I sat next to her on the couch. She rolled her head towards me, wearing a very contented smile. I kissed her and we kept kissing for a long time. She played with my cock as we kissed, tugging, squeezing, and pulling it back to life.

“I want to fuck this,” she said.

“Go for it,” I told her without moving. She looked down at my hard cock for a moment, flashed me a big smile, and straddled my hips. “Do you know what you’re doing?”

“Yes,” she whined, rolling her eyes. “I’m not a virgin.” She held my cock in her dainty hand before lowering herself on top of me. It took three or four tries before she worked herself down on top of me far enough for it to matter.

“You’re so big,” she gasped, experimenting with moving up and down.

“I’m man-sized,” I joked, grabbing two handfuls of teenage tit. Damn, she felt good. She lowered herself the rest of the way down on top of me and stayed pressed against me as we kissed again. Eventually, Kaylea began moving up and down. I moved my hands to her waist, helping her. We fucked for several minutes before she slowed. “Everything okay?” I asked.

Kaylea nodded, smiling as she said, “I was just going to ask you the same thing. Am I doing this right?”

“There’s not much you can get wrong,” I said, confused.

“You didn’t come yet, did you?”

“No, not yet. Is that okay?”

“I guess. It’s just that, usually, the guys I date? They, um, they usually don’t last this long.”

I nodded, reminded of what it was like to be a young man without any staying power. I had been like that with Claire, too. She had taught me self control, the kind I didn’t have available to me during Kaylea’s blowjob. “When it starts to feel really good for you, stop doing it that way,” Claire had taught me. “Trust me, if you change how you’re stroking, it will still feel good for her. Remember, she’s on a different pace than you.”

Without realizing it, that’s what I had done to Kaylea, too. It’s why my hands were on her hips, guiding her. I was making sure she didn’t push me over into orgasm-land too soon. As good as her pussy felt, and it felt absolutely heavenly, I was pre-programmed to last as long as my date once I started fucking.

“Let’s turn you around,” I said, smiling as she displayed her youthful nimbleness and turned around without ever moving off my hard cock. She crossed a leg in front of me and spun, giving new meaning to the idea of being “spinner.” I sat up, pulling her with me before I pulled her backwards against me. I raked a hand across her front, enjoying the feel of her pert, supple breasts before running my hand down her arm. I picked up her hand and put it between her legs. “Touch yourself,” I instructed.

“How?” she asked.

“The way I did it to you,” I said, pressing her finger against her clit. “Play with yourself the way I did it.”

“You mean, like this?” she asked and I felt her finger starting to make a small, tentative circle around her clit.

“Yeah, like that. Now make yourself cum.”

She wiggled against me a few times before stopping. “It’s okay if I do this, too, right?”

“It’s exactly right,” I told her, kissing her neck and moving my hands back to her perfect tits. “You can always do this,” I coached. “This way, maybe you’ll get off, too.”

She moaned, bounced up and down a few times, and then moaned again. “So good.”

“Keep going,” I told her, moving with her, rocking so my cock slid in and out as she played with herself. “I want to feel your orgasm with my big, hard cock so deep inside of you.”

“Yes,” she purred. “Say that again.”

“You like it when I talked dirty?” I asked. She nodded. “You like hearing about big dicks fucking tight pussies?”

“Yeah,” she groaned.

“Big, hard man-sized cocks deep inside your pussy.”

“Oh,” she said, shuddering a bit and pulling her away from her clit.

“No, don’t stop,” I said, pushing her hand back into place. “That’s not a real orgasm.” I waited until I felt her doing it again. “That’s it, Kaylea, finger that hot pussy of yours. Make yourself cum. Cum on my cock. Cum all over my hard cock and then you can suck me again.” She gasped. I kept going. “You can suck your pussy off my cock and then I’ll fuck your ass. Do you want that? Do you want my big dick up your ass?”

“Yes!” she shrieked as her real orgasm began. I wasn’t sure if she was answering my question or announcing its arrival. For the moment, it didn’t matter. I felt her pussy rhythmically squeezing around my hard cock, trying to milk an orgasm from the rock hard stone of my manhood but I had more control than she could understand with her eighteen years. I held on to my orgasm, twitching and throbbing as she came. As she had done earlier, she shivered at the end and then jumped off my cock so quickly I looked around the room as if something had happened that I missed.

Kaylea slipped between my legs, pushing my knees apart and grabbing my hard cock with her tiny hand. She immediately wrapped her lips around it and began sucking me. “Sooo good,” she murmured between long licks and deep sucks. “So fucking good.” That’s when I realized nothing had been wrong, she was only following my instructions.

“Okay girlfriend,” I said, caressing her cheek before taking her hands in mine and pulling her away. She rose with my gesture and I kissed her. I could taste her pussy faintly clinging to her lips. Damn that was hot.

“Are you sure that doesn’t make me a lesbian if I like how I taste?”

“I’m sure,” I laughed. I couldn’t help it. It was too cute how worried she was about that.

She gave me a shy grin as I laughed. She kept stroking my cock until I stopped laughing. Looking up at me with those innocent looking green eyes so crystal clear and bright, she asked, “When can we try to do it up my butt?” I felt my cock throb inside her hand and wondered if she could understand what that meant.

“I guess we can try it now if you want,” I said, trying to sound as calm and casual as I could though I felt my heart racing again at her eagerness to learn. “You need to be really clean back there.”

“I can take a shower if you want.”

“Let’s take one together,” I suggested. When I stood, her eyes tracked my hard cock before she stood, too.

“I like how hard you get,” she said.

“And I like everything about you,” I admitted. She lit up when I said that.

“I’m not being too, I don’t know, too inexperienced for you, am I?” she asked as we walked to the big bathroom.

“You’re perfect,” I said, stopping and pulling her into my arms. I held her against my chest and kissed the top of her head. “Too perfect.”

“What’s that supposed to mean?”

“One day, you’ll understand,” I said, smiling as I again thought how Claire would say little nothings like that to me that I never understood.

We showered together, laughing and playing with the soap. At one point, I held her close to me and ran a soapy finger between her buttcheeks. I poked at her ass and she squealed before giggling. “Two can do that!” she said, returning the gesture.

“Careful,” I laughed. “Guys can like that, too.”

“Gay guys,” she said and I didn’t argue with her.

The towels at the hotel were fluffy and felt soft enough to lose a full grown person inside of them. She raced me to the big bed, climbing on top of it on all fours before poking her ass up in the air while putting her chest on the soft comforter.

“See anything you like?” she asked, waving her upturned ass at me.

“Everything I see, I like,” I smiled, climbing on the bed with her. I gave her upturned ass a playful swat. We rolled around on the big bed, laughing and giggling before we started kissing and groping more than wrestling. I started teasing her, playing with her pussy and exciting her without pushing her past the point of being super excited.

“You’re making me want to fuck you again,” she complained.

“Good,” I said, slipping my finger inside her pussy. “Little sluts like to fuck, don’t they?”

“And suck,” she said, sucking my bottom lip into her mouth and gently biting it.

“And what about this?” I asked, moving my slick finger from her pussy to her asshole. I gently pressed against it and watched her expression. “Do little sluts like this too?”

“I want to like it,” she said.

“Kiss me,” I told her, holding my face just out of her reach. She wrapped her arms around my shoulder, pulled herself and pressed her lips against me. As she held herself against me, I pressed my finger inside her ass. Her grip tightened but her kiss never stopped. I wiggled my finger around a bit, allowing her to grow accustomed to the sensation of something being inside her ass before I broke her kiss. “Feel good?”

“More,” she said, kissing me again.

I picked up the bottle of lotion I had snagged from the bathroom as I moved between her legs. I knelt between her legs, keeping her pushed on her back as I squirted some lotion on my fingertips. I smeared that lotion against her asshole before poking the first knuckle of my finger back inside her ass. With my other hand, I thumbed her clit. She shivered with delight. “Not yet,” I told her.

“I can’t help it,” she said, squirming a bit. Was she trying to work my finger deeper inside or wanting more of my thumb against her clit.

“Tell me what you want,” I insisted.

“I want it up the ass,” she said, flashing a bright, eager grin as she said it. I pressed my finger a bit deeper inside her butt. She moaned and wiggled again.

“You like that?”

“Yes,” she giggled.

“Have you ever put anything up your butt?”

“Just my boyfriend’s dick, that one time.”

I thought that was a curious answer. If that was the extent of her anal play, why did she want more? I asked her as much.

“Because that’s what girls do,” she said. “It’s in all the porn and all the guys want it.”

“No shit?” I asked, startled.

“Ew!” she said, slapping me for my exceptionally poor choice of words.

“Sorry,” I said, laughing at myself. “But seriously, guys want this?”

“Don’t you?”

I nodded without explaining. How could I explain without sounding old? Back in my day, we wanted pussy and blowjobs and that was that. Hell, I had never even thought of using a woman’s backdoor for fun until I started renting adult videos on VHS tape from the local video store. Since then, I had been with women who were willing to do it up the butt. For a short time, right after my divorce, I dated a girl who really enjoyed it up the ass and that had been fun. Ass play was something Claire had never taught me.

“You’ve done this before, right?” she asked, apparently reading some of my thoughts.

“More times than you’ll ever guess,” I assured her. “Now roll over.” With that youthful enthusiasm, she bounced her way to her stomach.

“Should I get on all fours?” she asked, doing it anyway.

“Sure,” I said, going back to rubbing her asshole. This time I did it with my thumb. I teased her bright pink asshole, adding a bit more lotion before easing my thumb inside. She moaned and pushed back against me. With an unexpected wiggle of her hips, my thumb popped inside of her.

“Oh yeah,” she groaned and I was surprised with how much of a different her eagerness to learn was making. With my other hand, I reached around and played her clit a few times. “You’re going to make me cum,” she said.

“Not yet,” I said, determined to keep her on the very edge of her desire until after I was inside. “Grab your ass.”

Kaylea rested her face and chest on the bed, kept her ass upturned to me and grabbed her asscheeks. She instinctively knew what I wanted. She pulled apart her buttcheeks and I knew there was no reason to delay. I coated my hard cock with lotion and took my position behind her. I pressed my cockhead against that tight, puckered opened and remained absolutely still.

“If you want this, take it,” I said. I could see her face turned to the side as she looked backwards at me. I saw a small smile on her lips and felt her pressing against me.

“So big,” she groaned, easing away before trying again.

“Take it slow,” I said with a hand on her back. “Just work the head inside until it feels good.”

“Okay,” she said, pressing backwards again. It took three tries before it happened. Slowly, her butthole eased open as she taught herself to relax enough for entry. I knew that would be the key. She had to relax and take it on her own. I felt myself slipping inside of her and she groaned. Was that a good groan or a bad groan? I wasn’t sure, but I knew how to turn it into a good groan.

I leaned over her back and reached around her trim, tight body. I worked my fingers between her legs and rubbed her clit, following her body as she eased back and forth.

“Sooo good,” she groaned. She pressed backwards against me, taking me deeper in her ass and I remained still, allowing her to work at her pace. “Oh God, don’t stop,” she said, putting her hands in front of her and moving back to all fours. With better positioning, she was able to thrust with greater ease. Not wanting to risk hurting her, I remained still, except for the fingers I had pressed against her clit. With those fingers, I rubbed and clutched at her lovebud.

“Yes!” she cried out. “Fuck that ass! Fuck it! Fuck my ass!”

In truth, she was fucking her own ass, which was good and bad. It was good, because I knew she was in control and wouldn’t hurt herself. It was bad, because I didn’t feel as if I could make those little adjustments to moderate my excitement. I felt my passion rising and began panting with her. “Give it to me,” I groaned. “Give me that tight ass!”

“Yes!” she cried. “Yes! Yes!” And that’s when I felt her orgasm beginning. It’s different when you’re inside a woman’s ass. You can feel the contractions of her butt trying to close around the intrusion of your hard cock and when it can’t, it sends her to new heights. At least that’s the way it was described to me by that chick I dated who loved anal and that’s how it feels being on the receiving end.

I came inside her ass. She was too hot, too passionate and the squeezing of her asshole as she came was too much for me. I came, throbbing in counterpoint to her orgasm and revelling in every moment of it until we collapsed on the bed. I slid out of her ass, knowing it wasn’t the same as a pussy.

“Okay, that was intense,” she sighed. “Um, but I think I need to visit the bathroom.”

I understood. I used bar towels and the sink near the bar to clean the lotion off of me. I celebrated with one of the small bottles of booze from the bar and washed it down with another five dollar Coke before kicking back on the sofa and staring at silent porn on the TV. Dusk was beginning and I glanced at clock. It was after seven. Kaylea came out of the bathroom wearing a happy smile as she curled up next to me.

“Thank you,” she said, playing with my cock. I wasn’t hard, though I felt confident I could get that way again in a few more minutes. “That felt amazing.”

“I’m glad,” I said, unsure how else to respond to her thanks. Should I be thanking her? Claire flashed to mind and the way she always smiled wistfully whenever she came into my store. I realized we had a deeper connection that just a friendship following a single summer of fooling around. Would Kaylea and I have that? Only time would tell.

“What’s been your favorite part so far?” she asked, still caressing my dick.

“Easy, making you orgasm,” I said. “What about you?”

“Everything,” she said, making my answer feel too specific. “If I suck it, will you get harder faster?” I laughed and said I would right before she leaned over and performed her oral magic on me. It got very hard, very fast before she sat back up again. “What’s the next lesson?”

“I think I’m out of lessons,” I admitted.

“Can we still fuck again?”

“Definitely,” I said, leading her to the bed where we fucked for a long, long time. I guess Kaylea was trying to impress me with all the positions she knew because as soon as we found a good position, she wanted to change. We ran through the gamut from missionary and doggie style to cowgirl and reverse cowgirl. I’m not even sure of the names for some of the other ways we did it.

I had Kaylea finger herself and made sure she had another orgasms. After half an hour of gymnastics, Kaylea made me promise I would come inside her pussy again. I made her promise to have one more orgasm before I did and I made sure we came together, mostly because I have that kind of control.

It was almost nine before we left the room. I drove her back to her car. We kissed before she got out and drove off.

The next morning, I stopped by the hotel before work and settled the bill. After I left, I realized we had left the TV on. Oh well, maybe the maid would have some fun watching a bit of free porn. Kaylea had the next week off from work. This time, it was a family vacation and I guess that was for the best. Just the same, I smiled all day long.

Kaylea worked for me the rest of the summer. We got together twice more, but neither of those times felt as right as the first time. Still, we shared a secret that I think remains special for both of us.

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