Teaching Kaylea

"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.