Learning Lessons

Story Info
A teacher runs into someone from his past.
4.4k words
4.7
17.2k
30
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I moaned low as I made my first thrust into the moist folds of her tight pussy. I couldn't believe this was happening. She gave a quietly surprised squeal and her flesh gripped me like a fist as I throbbed inside her. I glanced down -- just a little more than halfway in. I could hear her panting, trying to control her breathing, then she released.

I pulled back slightly and thrust again. I hit the mark, then felt her open up, her cunt walls stretching to accommodate more length and girth than she had heretofore experienced. As I crested inside her, she uttered a low, guttural fuuuuck. Then oh, fuck! I leaned down and kissed her lips as her body trembled, then shook. She kissed me back as her pleasure exploded.

--

Hours earlier, I was sitting, nursing a cup of Irish coffee on the patio of Applebee's. My meal had been fine, as far as those things go. Not much to expect from a national chain, but it was what I could afford on a teacher's salary.

I was "treating myself" in hopes of forgetting what the day was -- the one year anniversary of my wife asking for a divorce. Second wife. I didn't learn my lesson from my first failed marriage that had ended 15 years before this one. In fact, I had barely left court -- literally -- when I met the woman who I was now trying to forget, working the coffee cart outside the courthouse.

She was Latina, beautiful, buxom and full of energy. A great cook, and almost as much spice between the sheets as she added to her homemade salsa.

Unfortunately -- damnit, I was supposed to be forgetting her. Please ignore that.

I tossed back the last of my mildly alcoholic beverage and snatched the check up when I heard a voice behind me.

"Mr. Miller?"

I turned to see an incredible mocha-skinned twenty-something brunette in a tight sundress that flattered her slim curves.

"It is you! I thought so. I haven't seen you since... Mr. Miller?"

I realized I had been staring and zoned out. Did I mention I'm not good with learning my lesson?

"You don't recognize me, do you?"

"I -- I'm sorry. You do have me at a disadvantage, young lady."

"I'm Kelsey. Kelsey Chen."

"Kelsey..." Suddenly the light switch clicked on. "Kelsey! Alyssa's best friend, of course!" Alyssa was my former step-daughter from the first marriage. Her mom was also bad with lessons. Kelsey and Alyssa had been almost inseparable since they'd met in Kindergarten.

"I... Wow. I haven't seen you for at least 10 years. You've really grown into quite a beautiful young woman."

Her smile could have launched another Trojan War.

"More like twelve, Mr. Miller."

"Please. We're both adults here. I think it's okay for you to call me Paul now."

She giggled.

"Okay, Paul. It was good to see you. Unfortunately, I was just on my way out."

"Oh. Good to see you too. I'm also headed for the door. Are you alone?"

She nodded.

"My date had to leave early, before we could get any dessert."

"I'm sorry about that. Well, if you have the time, we could walk in the park, catch up, and I could buy you some ice cream, just like old times."

She gave me a funny look, then, her eyes twinkling, she smiled again.

"Yes, Mr... Paul, I think a walk and some dessert would be wonderful."

I smiled back and waved for her to go first towards the cash register. She moved past me close enough I caught a whiff of her light perfume. I watched, spellbound at her almost perfect ass and hips sashaying up the aisle. The last time I saw her, she was 11 or 12, and definitely did not look like this.

I followed her as I reached for my wallet. She was about 5'6", most of her height in her incredible tanned legs. Lean and tight. Not an ounce of fat on her legs and thighs that I could see. What I glimpsed of her breasts appeared to follow that pattern -- firm, probably larger B cups. Long, brown-black hair with a wavy curl that fell in ringlets down her back completed the picture.

I couldn't help but wonder what she looked like underneath her summery clothes. If I recalled correctly, her mom was black and her dad Asian -- maybe Korean? -- and she appeared to have gotten the best of both genes. What I've heard the kids call "Blasian."

"Sir?"

"Huh?"

"How do you want to pay your check, sir?"

I heard a giggle behind me.

"Did I distract you again, Paul?"

I turned and winked at Kelsey, then shrugged.

I paid my tab and followed her out the door.

Once we got outside, she looped her arm in mine, sending shivers up my spine.

We casually walked down the path and into the public park that was still buzzing at 7pm at night.

"So how are your parents? What did you study in college? What are you doing for a living now?"

She laughed, tugging a loose curl and tucking it behind her ear. Her hand traveled across her long, tanned neck, then down to rest atop my upper arm.

"So many questions, Paul."

"Well, I haven't seen you in so long."

"Fair enough." And she began telling me about her life.

--

I held her in my arms, her hands clasped behind my neck, until her shaking subsided.

"OMG. That was perfect," she sighed.

"That... was only the beginning."

Her eyes got wide, and I felt her clamp her ankles behind my back.

I kissed down her neck, then nibbled on her rosy red nipples, hard and pointed like fingertips out from her oblong areolas. My hands on her hips, I started working into a rhythm, fucking her deep and long.

Her left hand strayed from my neck, touched my chest, then down. I glanced down to see her rubbing her swollen clit, doubling down on the friction between her plump love button and my thick shaft.

"Fuck, fuck, fuck. I don't want this to ever stop."

--

As we approached the area near the on-site ice cream stand, Kelsey paused.

"You know. I'm not sure I'm up for ice cream anymore. At least not at these prices."

"Oh, it's okay, Kelsey. I can afford it -- I don't get to do this very often, and I'd like to give you a treat."

She turned and looked at me, her gaze intense.

"That's not what I meant, Mis-- Paul."

I looked down at her in confusion.

She leaned in close, eyes still on mine, and stage whispered, "I do want a treat. I want something different for dessert."

She sighed at my quizzical stare.

"Men really don't get hints."

She reached out and took a handful of my shirt.

"Did you really not know that I've had a crush on you since, well, since I knew what such things were?"

She pulled me close and kissed me, full on the lips.

Thankfully, I had my wits about me enough to kiss her back.

After a moment, we broke the kiss.

"I don't understand," I managed, once I'd gotten my breath. "I thought you discovered you were a lesbian."

She smiled, tucked her arm in mine again and tugged me down the path.

"I guess a lot has changed since we last saw each other. I was 12. What did I know then? I was definitely confused, cause even then, when I found pictures online, the boys still excited me, just not as much as the girls. And then there was you... I am fully bisexual now. Have been since college."

"Well, that's good to know. But, Kelsey, I'm not sure."

"Mr. Miller. Paul. Please don't tell me what to do with my body. We're both adults now, you said that. And I know you've been checking me out. And not in some, I'm trying to remember what she looked like in Middle School, is this the same girl? No. I feel your desire for me."

"You were just on a date..."

"And that's no concern of yours. Look. My place is just a block from here. I want to take you there, and take you. No strings attached. Just some good hard fucking between old friends. Unless... Oh, I should have asked. You can still have sex, right?"

"I'm not that old."

"Then it's settled. Let's go to my place and I'll give you a night to remember."

"Lead on!"

--

I pushed her legs up, ankles onto my shoulders as I pounded inside her young, hungry flesh. Her fuck, fuck fuck, echoed the rhythm of my cock plunging inside her.

"Gawd, I love you," she murmured.

I tried to ignore it. Then my mind shifted to more pressing matters.

"Oh shit, I'm, fuck, I'm close. Do you want me to cum --"

"Inside me."

"But I'm not wearing a condom. Are you --"

"Yes. Yes! YES! I want to feel you explode inside me, fill me up. Please..."

--

We were barely in the door when Kelsey pulled off her sundress, then her sports bra.

"Sorry if you wanted to go slow, but I've been waiting a long time for this."

"No apology necessary," I groaned, looking her up and down.

As I mentioned before -- no fat on her whatsoever. Her tan went all the way down, no lines. Her tight, toned tummy was accented by a tiny gold stud. Her firm, perky young breasts had dark areolas about the size of a half dollar coin, with fat, but short nipples that I knew were going to be super sensitive.

I quickly unbuttoned my shirt and pulled it off, suddenly self-conscious of my paunch. I quickly unhooked my belt as Kelsey came over and kissed me. Her hands roamed all over my chest and back. She paused and looked up at me.

"It's okay. Dad bods are hot."

I chuckled.

"I doubt that, but hopefully I can take your mind off of that."

"Oh, really!?"

She stepped back, grabbing my trousers and yanking them to the floor, almost falling down with them. Then she leaned back and gasped. I felt her tiny brown hands caress my heavy balls, then grip my thickening shaft, barely fitting around.

"You were not kidding, Paul. Oh, fuck. Look at this thing. THIS is Mr. Miller, right here."

She squeezed my nearly nine-inch cock harder, then took the mushroom head into her mouth to taste my precum. I felt her tongue swirling over the head, then she released it and licked up and down the shaft, even slurping on my balls. I was in heaven.

"Fuck, Kelsey, you are so damn good at this."

"You should see me eat pussy."

"Fuck!"

I slid my fingers in her hair, gently guiding her as she worked her mouth up and down my shaft, even taking it deep in her throat, til she gagged a little.

"I don't think I've ever had a real one so big before, Paul. Thank you."

"Thank me? No, darling. It's the other way around."

She hopped up and moved to crouch on the couch. She pulled down her tiny black panties and spread her ass cheeks so I could see her treasure. Her pussy lips were perfect, the skin slightly darker than the rest of her, thin and tight. She pushed a finger in and teased her own clit, then slipped it out again.

I leaned down and sucked on her digit, tasting her sweet Blasian sex. So good. I leaned in, my tongue lapping and teasing at her pussy flesh as she moaned and begged for more.

Finally I stood up, slapped the thick head of my cock on her thin lips. She reached back, grabbing the shaft and guided me into her tight love canal.

Fuck, she was tight. Both my exes had been, lets say accustomed to size before they met me. Kelsey seemed to know her way around a bigger cock, but whatever she'd fucked before hadn't left her as opened up.

As I pounded inside her, she pushed herself up, reaching to grab my neck, kissing me. The pressure on my cock was glorious, and I gripped her perfect tits in my hands, teasing them as she worked me.

As I suspected, her nipples were key. After a few moments, a lot quicker than my usual doggie style fuck would reach it, she was moaning and gasping. I felt her orgasm on my member, then kept teasing her nipples as waves of pleasure rippled through her.

Finally, she collapsed, slipped off my cock and the couch, back down to her knees.

"Feed me," she moaned, licking, then slurping her own juices off my penis before taking me as deep as she could, over and over. She reached around and slipped a finger into my ass, probing and got her reward.

I convulsed and suddenly I'm pumping her mouth full of hot semen. She sucked down every drop, then licked at the shaft, making sure it was clean.

Behind me, I heard a key in the lock. What the...

"Oh, good. My date is home. Just in time."

I freaked out, tried to get away, get my pants up, but Kelsey had a hold of my cock and wouldn't let go.

"Relax, Paul. It's okay. She wanted to meet you."

I slowly turned as the door opened...

And my ex-wife entered.

Except it wasn't. It wasn't Alyssa's mom. It was Alyssa's mom looking even better than when I first married her. I looked her up and down. Her breasts were considerably larger. Her hair was lighter, longer, more red than brunette. She smiled at me.

"Hi, Daddy."

"A-a-Alyssa. You. You shouldn't see me like this. I- I"

"Oh, Daddy. We're not related. You know that. You're just a hot older man in my apartment who, I'm guessing, just filled my girlfriend's mouth."

Kelsey nodded, grinning. She hopped up and went to kiss Alyssa, both of them making sure I could see Kelsey sharing my recent discharge with my former step-daughter.

"MM. Yummy, Daddy."

"Alyssa, this is very... I don't know if I can. I should go."

"Daddy!"

Every time she said that, my cock pulsed and throbbed.

"Sorry. Should I call you Paul? Would that make it less weird?"

"Yes. No. I don't know..."

"it's kinda hot, calling you Daddy. It definitely helps me get ready."

"Get ready?"

Kelsey walked over to me and kissed me. In spite of myself, I kissed back.

"Alyssa is... well, she's not a virgin. She's mostly been with girls. Although lately she's been a little, jealous, I guess, of my boyfriends. The boys she tried things with were.. inadequate. If she is going to make an informed decision, she needs to know what a real man is like. So..."

"You... you want me to fuck her -- you -- my daughter."

Alyssa came closer.

"Step-daughter, Daddy."

She took my no longer flaccid cock in her hand.

"And I can see it turns you on. We're not blood related, so... will my Daddy fuck me? Let me know what a real cock feels like?"

She dropped to her knees, then yanked the flowy poet's blouse over her head. Her breasts were at least D, if not DD. Kelsey knelt next to her and teased my balls.

"Start by licking the shaft. Take your time with it."

I couldn't help myself. I looked down to watch my step-daughter working her tongue up and down my dick.

"Nibble on the head a little," Kelsey instructed.

"Would you help me?"

"Of course."

Now I was watching my step-daughter and her best friend, who I had just fucked, wrapping their tongues around the head of my cock, kissing it and each other, as they stroked me to hardness.

Alyssa reached back and unhooked her bra, letting her tits fall free. Bigger, but still perkier than her mom's when I first knew her like this, her areolas oblong. Kelsey reached out and grabbed both of Alyssa's nipples, tugging on them. They plumped in her hands, sticking out almost a half inch from Alyssa's breasts.

Kelsey dipped down and started sucking on Alyssa's nipples as my step-daughter did the same to my raging boner. While she was nowhere as good as Kelsey, she made up for it with enthusiasm.

Soon, in spite of myself, I was lacing my fingers through Alyssa's hair, long and curly like her mom's, just a deeper shade. If I just kept focusing, telling myself it was Kathryn I was face fucking and not her daughter, I could. Fuck... nope, still hotter with the daughter.

I gasped as I felt air on my cock. Alyssa had released me from her mouth, but she rose and grabbed my hand.

"This'll be easier in the bedroom."

In a haze of lust, I nodded and followed her. Her butt was a round peach, just like Kathryn's, but Alyssa's was somehow even more alluring in a skirt than her mom was butt-naked. Pun intended.

Alyssa and Kelsey directed me to sit at the head of the bed, legs akimbo. They climbed up on either side, straddling my lower legs.

Alyssa laid on her side and kissed my balls, then licked her way up the shaft and suckled on the head. It wasn't the best blowjob ever, but it was young, and hungry, and hotter than it should have been, due to the taboo nature of it.

Kelsey kissed my thighs, then stretched over me and unzipped Alyssa's tight skirt. She tugged it down, revealing my little girl was wearing no panties. I hazarded a look -- her pussy lips were plump and soft and she had a tiny patch of reddish brown hair right above them.

Kelsey kissed Alyssa's thighs, as she had done mine, then traced the outside of Alyssa's pussy lips, making her moan on my cock. Kelsey used her fingers to caress and probe, then leaned closer and took my step-daughter's pussy in her mouth, pressing so close, she had to be holding her breath.

"Oh fuck, Daddy. She's so good at eating me. She makes me cum over and over."

Alyssa kept slobbering on my cock, as much as she could while being slightly distracted by Kelsey's talented tongue.

I eased Alyssa off my dick, gently caressed her face and leaned down to kiss her.

"Why don't you two play for a while. Daddy'll just watch."

She smiled so very big at me, then rolled over... She and Kelsey kissed and licked. Watching them both, sensually kissing and touching each other, was incredibly hot.

Eventually, they shifted into a 69 position, and I could see that Alyssa was just as talented as Kelsey in the pussy licking department. Each of them brought the other to the brink several times before they kept going, and waves of orgasm wracked both their young bodies.

"Are you sure about this, Princess?"

Alyssa nodded.

"Yes, Daddy. I want to feel you inside me. I need it to be someone I trust, not some random hookup or college kid. I want my first 'real time' to be special. If I'm going to be reborn as a bisexual, I want it to be with the man I love more than any other."

"Okay, baby. If that's what you want."

She grinned, then moaned. Her hand went down and pulled Kelsey's face off her crotch.

"Daddy's turn, babe."

"I got her primed good for you, Paul. Lord knows, she'll need some lubrication for that beast between your legs."

"You say the nicest things."

"Hey, don't mock. After this, I want you inside me one more time before we send you home.

"Deal."

Kelsey backed up, then crawled up behind Alyssa, taking her in her arms, holding her for me.

Alyssa's legs were wide, I could see the wetness of Kelsey's tongue and my little girl's arousal shining on her pale skin.

I knelt close. I gently stroked Alyssa's clit and plump pussy lips with the shaft, before positioning the head right at her tiny fuck hole.

I moaned low as I made my first thrust into the moist folds of her tight pussy. I couldn't believe this was happening. She gave a quietly surprised squeal and my step-daughter's flesh gripped me like a fist as I throbbed inside her. I glanced down -- just a little more than halfway in. Alyssa was panting, trying to control her breathing.

"Just let go, baby girl. It'll hurt just a tiny bit, but the pleasure will be intense."

She nodded.

"Okay, Daddy, I trust you."

Her body tensed for a moment, and then she released her kegel muscles.

I pulled back slightly and thrust again. I hit the mark, then felt her open up, her cunt walls stretching to accommodate more length and girth than she had heretofore experienced.

"OH, DADDY!"

As I crested inside her, she uttered a low, guttural fuuuuck. Then oh, fuck! I leaned down and kissed her lips as her body trembled, then shook. She kissed me back as her pleasure exploded.

I almost came right then, as my step-daughter, my Princess, the spitting image of my first love, took my cock deep into her body and orgasmed over and over.

I held her in my arms, kissing her, her hands clasped behind my neck, until her shaking subsided.

"OMG. Daddy, that was perfect," she sighed.

"That... was only the beginning."

Her eyes got wide, and I felt her clamp her ankles behind my back.

I kissed down her neck, then nibbled on her rosy red nipples, hard and pointed like fingertips out from her oblong areolas. I love long, fat nipples. It had been one of my favorite things about Kathryn, Alyssa's mom, that I missed with my second wife.

12