My Mom’s Best Friend

Summary: Lucky nerd seduced by MILF at his parents' Halloween party.

Note 1: This is a Halloween 2023 Contest Story so please vote.

Note 2: Thanks to Tex Beethoven for editing.

My Mom's Best Friend

My parents threw a Halloween party every year. They'd always sent me to grandma's house in the past, but now that I was eighteen, I was going out to a Halloween party with my friends from school.

I was a senior in high school, but was already eighteen, since I'd started school late. My Dad had been in the Navy back then, and we were stationed in Japan when I was five.

Anyway, the party I went to was fun for a while, but then I struck out with Elizabeth, the girl I'd been pining for all semester. She gave me a couple of chaste kisses, but that was it. In homage to the final Indiana Jones movie (which I thought was awesome, even though it didn't do well at the box office), I was dressed in a full I.J costume... I even had a whip! So I returned home just after midnight, and the party was still underway.

I went inside, and the house was rocking... who knew my parents could host such a banger? Good for them! I actually had to give them some street cred. This party was fire! This party was way more dope than the one I'd gone to. Plus, the music they were playing was 1980's classics like You Shook Me All Night Long and Jessie's Girl, which was way better than the generic auto-tune dance shit that had been blaring at the other party.

I chatted with Mom, who was definitely tipsy, with our neighbour Joe, one of my teachers Mrs. Walker, which was a little awkward, especially since she was dressed in a damn hot maid outfit with cleavage down to her navel and the tops of her nylon stockings showing, and with a few other people. I poured myself some punch (which was spiked quite generously), with the intention of jerking off to Mrs. Walker (which I'd done many times, but never picturing her as a slutty maid), when I encountered Mom's best friend Barbara... dressed exactly like a Barbie Doll, all in pink. She also looked a lot like Margot Robbie, who'd played Barbie in the recent movie. My already hard cock inside my pants flinched to salute her.

"Hi, Simon," she greeted, drink in hand.

"Hi, Barbara," I greeted back, trying not to look like I was staring at her big tits, or her long legs in pink pantyhose. I loved nylons, but too few women wore them. My Mom did sometimes, but she didn't count, since although she was hot... well... she was my Mom. Mrs. Walker almost always wore nylons, which is why I jerked off to her so often, and my target at the other party Elizabeth often did... besides being cute, funny, and smart... she usually wore nylons a couple times a week.

"You're home early," Barbara observed.

"Yeah, the party was boring," I said, trying to focus on her eyes, but my own eyes weren't doing a good job.

"You didn't get laid?" she asked bluntly, just as I was taking sip of my punch... and I was so startled by the question I spit out the mouthful all over myself. "Sorry," she giggled, "was that question too blunt?"

"It was quite surprising," I admitted, totally embarrassed.

"But isn't that the main reason for teen parties?" she asked, her tone shifting to sensual, or maybe that was just in my head, "to get laid?"

"I suppose it's one of the goals," I said. Although if that was the case, I had a perfect strike-out record so far. I was rather shy, so I was actually proud of myself for even trying for first base with Elizabeth... even though all I got was a couple of kisses...since that was progress... and even if she was drunk and might not remember it, I would. Forever.

"As it should be," she said. "You should definitely hook up while you're still young. Things dry up substantially once you get to be my age."

"I can't fathom that's possibly true in your case," I said. Barbara was easily the hottest woman I'd ever seen in real life. Besides being absolutely stunning, she owned her own women's clothing shop, so she always dressed in hip, modern clothes.

"You're so sweet," she smiled, taking my hand in hers... and making my hard cock flinch. "But alas, this party is just a bunch of old people trying to recreate their youth for a single night."

"Everyone looks like they're having fun," I observed.

"Oh, they are," she agreed, "but they're only living the lives they were given, the ones they're supposed to be living, according to some arbitrary set of rules."

"I'm not following you," I said.

She continued holding my hand, which had my head fogging up with curiosity about why she still was. Never had holding someone's hand felt better in my life... or at least compared to my very few and brief prior hand-holding experiences.

"Well, ever since Jake died, I've been trying to move on," she semi-explained.

"I'm still so sorry about this passing," I said. Jake had been a great eye, a professional race car driver who got into a serious crash last year, and who'd died from his injuries a few weeks later. The only silver lining had been that he'd been in a coma until he died, and as far as anyone knew... including the doctors and nurses at the hospital... he'd never regained consciousness, so hopefully he hadn't suffered any pain.

"Thanks," she said, with some sadness in her eyes.

"He was a great man," I said, having admired him greatly. Besides marrying the hottest woman ever, he'd worked for a couple of charities in the off-season, so he was a great role model for me. He was like my second dad... a cooler dad... no offense to my real Dad... he was great too... just not especially cool.

"Yeah, he really was," she agreed. Surprisingly, her words conveyed \a slight sexual tension, that I'd think would be crushed by our conversation about her beloved man, who was no longer with us. Then after an odd silence, her sadness seemed to evaporate, as she said, with her smile returning, "He lived every moment like it was his last, and that's a trait of his I try to live by."

"That's a great way to live," I approved, wishing I had the courage to live my life even a small percentage as adventurously as he had. He'd also climbed mountains, jumped out of airplanes, and did motivational speaking at self-realization events. I couldn't fathom myself doing any of those things.

"It is, isn't it?" she agreed.

"Yes," I agreed too. "He was an inspiration." Then I thought again. "No, he still is an inspiration."

"That's sweet of you to say," she said, her hand still holding mine.

"It's the truth," I said, "I wish I could be even one percent as adventurous as he was."

"Do you mean that?"

"I do."

"Mmmmmmmmm," she moaned ever so softly, which made my very hard dick flinch in my costume again... which thankfully was a real costume, not one of those overpriced Halloween monstrosities so cheaply manufactured they might as well be made of paper ... so my dick wasn't very obvious while it saluted this blonde beauty.

She looked around thoughtfully, then apparently decided something and said briskly, "Meet me in the basement bathroom in five minutes."

"Really?" I asked, flabbergasted. There was only one reason she'd issue me such a summons.

Seeing the astonishment on my face, she whispered, "I can tell what you're thinking, and you're correct. So don't make me wait," leaning close to my ear and briefly nibbling on it. Her hot breath made my cock pulse, and a rush of adrenaline to course through me.

"Yes, ma'am!" I said emphatically as she sauntered away. As I followed her shapely back end with my eyes, I saw that her pink pantyhose had sexy seams down the back.

"Hey, son," Dad startled me from behind.

"Hey, Dad," I said, back, breaking my stare.

"How was your night?"

"Just so-so," I said.

"I feel ya," he said, trying to sound cool. Then he offered, "Feel free to hang out with us if you like."

"Thanks, but I think I'll head down to the basement and game a little," I made up on the spot.

"That's okay too," he approved, as 'Hungry Like the Wolf' by Duran Duran started playing. "Oh. I'd better find your Mom. She loves this song."

"She's over there talking to Barbara," I pointed out.

"Jesus, that outfit!" he said.

"Yeah, she's really something," I agreed.

"She sure is," Dad said, checking her out, just like I was doing.

"You do know you're married, right?" I asked playfully. We'd checked out hot women together lots of times.

"I'm married, not dead. There's no reason I can't admire one of God's beautiful creations."

"That may be the corniest thing you've ever said," I laughed.

"Worse than my dad jokes?"

"Far worse," I agreed, still chuckling, as Mom started heading towards us. "Go and dance with your own hot babe."

"Yeah, your Mom is hot, and she's hungry for the wolf," Dad said, doing a Michael Jackson with his crotch, before leaving me to meet his wife halfway.

"Gross," I said, although I had to admit my Mom was aging awfully well.

I filled up my cup with some more of that strong punch, and headed for the stairs. The basement wasn't only where my bedroom was, but also where my entertainment system was set up, including a 60-inch television, surround sound, and a PlayStation 5. It was my oasis.

I was just checking my phone, when I glanced up and saw Mom and Barbara high fiving each other. Then Barbara started downstairs, so I hurried to join her. When we reached the bottom together, she looked around, smiled, and said, "You have your own little oasis down here."

I smiled back, since that was exactly what I always called it. "Yeah, it's my stress-free zone." Then I asked, "Why were you and my Mom high fiving each other just now?"

"Ummm... Oh, that!" she said. "I was just telling your mother what a fine young man you'd become, so... umm... I was actually high fiving her," she said, before taking my hand again and leading me towards the bathroom.

While she'd confirmed what her intent was, her leading me to the bathroom, instead of to my bedroom, was making me a little doubtful. But there was no innocent reason for her to lead me into the bathroom either.

Immediately after we'd entered the bathroom, she closed the door, shoved me back against it, grabbed my head, and started kissing me... hard.

I kissed her back in awe. I was kissing my second girl of the night, and this one was my dream MILF!

After a couple minutes of passionate kissing, her tongue slid into my mouth. So I slid mine into hers. Then after another minute or so, she broke the kiss, seized my very hard dick and squeezed it. Then she asked, "Ready for an adventure?"

"God, am I ever," I moaned. My Mom's best friend was squeezing my dick!

"Mind if I check out your snake?" she asked, as she lowered herself to her knees.

I appreciated her Indiana Jones reference, even though it didn't make much sense, since Indiana hated snakes. But I was in no mood to quibble, so I just moaned, "Don't mind if you do," as I looked down in utter awe at my dream woman on her knees, pulling my pants down.

"This is the kind of snake I really like," she said in a sexy tone, as with my pants already around my ankles, she pulled down my boxers... and I was super happy I'd decided to wear my classy SAXX boxer briefs, as my hard seven-inch cock suddenly sprang out... energetically saluting her. Once she saw it, she cried out, "Wow!" obviously impressed, and she wrapped her hand around it, making me moan. "Oh my, what an impressive cock!"

"Thanks," I moaned, and I watched in amazement, as she leaned forward and took my cock into her mouth... thus, my first ever blow job was being performed by my Mom's best friend. "Oh, fuck!" I added. The sensations from her lips wrapped around my cock were exponentially more pleasurable and intense than using my hand... even though I always used lube.

"Mmmmmm," she purred, as she began bobbing on my cock.

Unfortunately, after not even a dozen bobs, I was ready to come. I apologized as I moaned, "Sorry, but I'm already on the verge of coming!"

To my surprise, she just kept bobbing and moaning, and a few seconds later, I was coming in her mouth, groaning, "Ohhhhhhh, God!" The intensity of my orgasm was much more extreme than any I'd ever given myself by hand... and its duration was also extended immensely, because she kept sucking me all the way through it and beyond, not slowing down even after I'd shot my entire load down her throat.

After another minute, she finally backed away from my dick, stood up and said, "Yum! I hope you can generate another load for me before too long."

"No worries," I said confidently, and I grabbed her by the hips and lifted her onto the sink counter.

"Oh, my! I like a man who goes for what he wants," she gasped.

While I'd never had a blow job before, and only one ineffective hand job, I'd done a bit of pussy eating last summer at camp. One of my fellow councillors had let me go down on her a few times... although she didn't repay the favour... except once when she rubbed my dick through my shorts and made me come in my underwear.

"Now I want to taste you," I said, as I parted her legs to discover she wasn't wearing pantyhose at all, but thigh-high stockings... and I couldn't help stroking my hands up and down the sheer silk. "I have a thing for nylons," I added.

"I know you do," she responded.

"You do?"

"You check out my legs all the time," she said. "But only when I'm wearing nylons."

"It's hard not to be conspicuous when the sight of them is so amazing," I said, as she lifted her ass off the counter to pull the hem of her one-piece costume even higher, revealing she wasn't wearing any panties.

"I removed my underwear and stuffed it in my purse just before coming down here," she said, while I stared at her almost completely shaved pussy, with just a tussle of hair above her slit, with undeniable wetness glistening on her labia.

"You're so hot," I said, as I directed my head towards her pussy. "May I taste you?"

"You'd better! I've just swallowed your load," she complained playfully.

"Then you're entitled to come on my face," I said, before extending my tongue and lapping up the wetness that had collected between her pussy lips.

"Fair's fair. You're welcome to squirt your next load on my face too," she moaned, as my tongue made contact, and I began making slow, paint-stroke-like movements.

"Mmmmmm," I said, both because of her offer, and the taste of her pussy.

"Or if you prefer... on my tits, or in my pussy, or on my feet," she listed off.

"Or all of the above," I replied, without skipping a single movement... each choice was so utterly delicious to imagine my doing.

"You may certainly do all of those, if you can reload that many times," she promised, as her fingers went gently through my hair.

"I can definitely paint you white that many times," I said, thinking to myself, Or die trying!

"I appreciate a man with stamina," she moaned, tugging my face a bit more tightly against her pussy.

"You taste so good," I said, wanting her to know that.

"I know," she said. "Your Mom loves the taste of my pussy too."

"What?" I gasped, my eyes going wide at such a shocking revelation!

"Your Mom and I have been playing together since before either of us met the love of our life," she added. I kept licking, while I tried to process that my sweet Mom could possibly be cheating on my Dad like that.

"Wow!" I said, not knowing sure what else to say.

"And don't worry," she added as I wiggled my tongue up and down, first in zed-like, and then backwards zed-like patterns. "Your father knows all about it."

"He does?" I gasped, her hot confessions getting stranger and stranger.

"He does," she assured me. "And he's known since before they got married. They tell each other everything."

"Wild!" I said, still gasping while I processed this plethora of revelations, added to the equally shocking facts that I'd just gotten my first blow job from my Mom's best friend, and now I was eating her pussy.

"Mmmmmmm-hmmmmmm," she moaned, as my tongue flicked her clit while I felt her legs twitching against my head. "That's it, right there Simon, right fucking there! Don't stop, baby."

Spurred on by her increasing moans and stimulating words, I accelerated my attack on her clit by sucking it into my mouth and tugging on it.

"Oh, fuck! That's it, baby," she moaned, her forceful hand shoving me hard against her pussy. "I'm so close!"

Using my lips and tongue, I attacked her clit, as she lifted her ass slightly, and a few seconds later, I tasted and felt gushes of her sweet cum while she erupted all over my face... surprisingly not vocalising at all while her orgasm struck... which hadn't experienced before in my limited pussy eating.

I hungrily lapped up her delicious, addicting pussy cum, while she continued holding my face pressed against herself. I felt her body trembling from the orgasm I'd just given her. But wait, I need to say that again: NEWS FLASH... I'd just given the hottest woman I knew an orgasm!!

"Oh, God was that good!" she gasped out a couple minutes later, while she finally let go of my head.

"Agreed," I said, my face slick with her juices, as I gazed up at her deliriously.

"Now it's time to fuck me," she said. "I need that dick inside me right now!"

"Um, okay," I said, standing up, my dick still completely hard, and ready for round two. I was still finding it unbelievable that I was about to fuck her... was about to lose my virginity to my Mom's best friend!

"You do want to fuck me, don't you?" she asked a bit worriedly, hearing the hesitance in my response.

"I've never wanted anything more," I said point blank. "But I think you need to know that I'm a virgin."

"You can't be serious!" she said, genuinely shocked by this particular revelation.

"Yeah," I said sheepishly. I was pretty sure there weren't very many eighteen-year-old virgins around.

"Then are you sure you want to lose your cherry to me?" she asked with a look of genuine concern.

"No question about it. I've had a crush on you since before I even knew what a crush was."

"That's so sweet," she said. But still concerned, she asked pointedly, "but you know you can only lose your virginity once?"

"Yep. And I can't think of another gorgeous woman on this planet I'd rather lose it to," I replied, and I kissed her.

We kissed for a couple minutes, before she broke the kiss and said, "Then if you're sure you want to, go ahead and slide that big, virginal dick into my cunt, and fuck me good."

Hearing such a nasty invitation coming from her mouth was exhilarating, and a major turn-on!

She reached for my dick, and placed it against the entrance to her tunnel.

I took a deep breath, and slid it inside her.

"Ooooooh!" we both moaned in almost perfect unison, as I lost my virginity to the sexiest and most beautiful woman in the world!

"That's it, baby," she moaned, as I slid all the way inside her.

I didn't respond with words. I was completely in awe of the situation I was in, and the surreal sensations of actually having sex.

"Now fuck me, baby," she moaned once I was all the way inside.

So I started pumping... and obviously the act of fucking was so different with another person taking part.

"Ohhhh," I moaned, watching my dick slowly sliding in and out of her pretty pink pussy.

"That's it, baby. Give me that big cock," she moaned. My self- esteem was flying through the roof from what was happening, as well as from her complimenting my dick. I knew I was above average, I'd noticed I was substantially larger than most of the other guys at school, including most of the so-called popular people, since there was no disguising your manhood in the locker room.