How I ended up NYE in the bed of my best friend’s MILF mom [mF]

“I made you lunch. Sandwiches and chips and a cookie.” Joakim’s mom set plates down in front of us. She looked so pretty with her dark eyes and bronze hair and slim build and that sophisticated form-fitting brown sweater.

I caught her eye and smiled. “Thank you, Ms Gautier.”

She grinned back and tucked her chin, and my cheeks went warm, tingly, like a shiver but without shaking. “Oh, Raff,” she said with a laugh, “You can call me Natalie.”

I was thirteen years old then, and I remember it clear as if it was yesterday, the first time I flirted with Joakim’s mom.

“What are you boys up to this afternoon?” She watched me blush. It was good-natured teasing of course, kidding along with a boy just discovering women. I’d been best friends with Joakim since he moved to my school when we were eight, and it had always been just him and his mom. I was over at his house all the time.

“Nothing, Mom,” Joakim said, “Just video games.” He was oblivious to the epiphany I was having next to him, the one where my pubescent brain was flooding with hormones, and the shape of his mom’s body started to take on so much meaning.

“Alright, have fun then.” His mom shot me a final grin before leaving Joakim’s room.

It’s funny the way that works. I’d always known Joakim’s mom was cute, but in the same way that I knew she worked in marketing, or liked drinking coffee. Being cute was just a part of her. Now, though, that cuteness began to mean something special. It was the beginning of my… ‘obsession’ is too strong a word. An ‘infatuation’ I guess is what it was. Smiling at Joakim’s mom and her smiling back, it was just something fun we did. Our little connection.

As I grew older, when I went over to Joakim’s house, or when she dropped him off at mine, I always made sure to greet her. “Hello, Ms Gautier. How are you doing today?”

And she’d smile back, every time. “Wonderful, Raff. But please, call me Natalie.”

I’d want to chat with her more. I’d tell her about school, about sports. She was kind enough to humor me.

When I started dating, I told her about that, too, and that’s when I saw her take a real interest. Joakim told his mom nothing of his dating life, whereas I was always honest with her. I was in that horrible, awkward, fumbling phase where I’d be spending time with girls who had as little idea how to have relationships as I did, and I’d make a mess of it. Ms Gautier was always there, to give guidance, to be a patient ear.

“Can I get your advice, Ms Gautier?” I was fourteen at the time.

“Of course, Raff, anything.” She closed her laptop lid and leaned forward, giving me her full attention.

And I told her about whatever high school freshman drama I was having. She listened stoically, and gave me some sage suggestions. I don’t remember what they were.

What I do remember was her hand on my knee, the way her fingers felt touching me. She was looking cute, the light glinting off her eyes, off her painted lips. I thought about her that night, her loose blouse, the swell of her tits beneath, as I was jacking off.

By the time I was old enough to drive, I’d head over early, while Joakim was still getting ready. An excuse to chat with Ms Gautier made me tingly. I’d ask her about whatever I could think of, but she was smooth, and she’d turn the conversation back to me.

“Who are you dating now, Raff?” she said, “Any girls you have your eyes on?”

I was sixteen. “Well,” I hesitated, should I tell her what happened? But I was always honest with Ms Gautier. “I was at this party yesterday, and this girl Anna, a senior, we were making out, and then, like, she said her ride took off without her, and I offered to drive her home, and I did, but when we got there we kept making out, and, then, well, she gave me a blow job.” I hadn’t told this to anyone else.

Joakim’s mom set her coffee down and let the silence hang. “Did you like it?”

I blushed. “I mean, of course. Who doesn’t?”

“Well,” she said, “Congratulations, then. Are you going to hang out with this Anna again?”

“That’s the thing.” I scratched my chin. “I kinda got the impression she doesn’t want to.”

“Why not?”

“I’ve sent her, like, five messages and she hasn’t responded to any of them.”

Ms Gautier sipped her coffee and considered. “Probably right, then. If she was interested, she’d respond. Instead, she’s missing out.”

And a few months later, when I had sex for the first time, it was with advice Joakim’s mom had given me. Holly Gordon and I had been dating for a few weeks, and she was just as inexperienced as I. But I was armed with Ms Gautier’s wisdom, a key to reading Holly’s body language, to being considerate and reciprocating.

And when I told Ms Gautier about it the next day, how much Holly and I had enjoyed, she was genuinely happy for me.

After that, even though I was with Holly, I became more brazen with Joakim’s mom. “Looking good, Ms Gautier,” I’d say, and flash her a smile. “That’s a sexy dress, I love it.”

Even Joakim couldn’t ignore it. “Cut that shit out, Raff,” he’d say, “It’s weird.”

“What?” I’d play at innocence, “I’m just being friendly.”

“Be friendly somewhere else,” he’d respond.

But with his mom and me, it was all just chaste flirting, so of course I didn’t stop.

“Wow, new hairdo, Ms Gautier, I like it. Looks good on you.” “That color blouse, Ms Gautier, very nice, bring out your eyes.” “Rockin a new tennis outfit, Ms Gautier? You look good in it.” “Wow, got a hot date tonight, Ms Gautier? He’s a lucky guy.” “Your smile always warms me up, Ms Gautier, you know that.”

“Call me Natalie,” she’d say, every time.

It wasn’t all one-sided, I wouldn’t have kept it up if she wasn’t appreciative, sending me flirtatious grins, doing little twists and turns to show off her outfits. She liked getting the attention as much as I liked giving it, but it was always just a game. I wasn’t actually hitting on her. She was just cute, and I wanted her to know that I noticed. I was just being nice, right?

And I thought I really was.

Last night, New Year’s Eve, Joakim was hosting this party at his mom’s house. We’ve both got our bachelor’s degrees now, and it’s his first year at grad school, my first year in ‘the real world.’ He invited me and our other high school friends over for a little reunion and to ring in the new year or whatever. His mom had some of her friends over, too, and the two crowds mixed, at least once the liquor started flowing.

Throughout the evening, I was chatting up this pretty blonde girl, Amy. I’d always thought Amy was cute, but she had met her soul mate freshman year of high school and only ever had eyes for him. They were going to be together forever. But of course in college they’d broken up. So here was my chance, and I thought things were going well, but by midnight when we watched the ball drop on TV and someone shot off some fireworks in the street, Amy was with some other guy and I was by myself. Even Carla, my backup plan, was grinding her ass into Joakim’s lap. I cheered in the New Year without feeling it, not wanting to be a downer.

“Happy New Year, bro,” I gave Joakim a hug. He was grinning ear to ear, Carla dragging him to his bedroom.

I sat down on the couch and waited. Joakim said I could crash in his living room, but the music was blaring, people were dancing, the party showing no signs of winding down. The world was oblivious to my eagerness for the night to end. And then someone plopped down next to me.

“Nobody to kiss, huh?”

I looked up. “Oh, hi, Ms Gautier. Happy new year.”

“I saw you talking to that blonde girl earlier,” she said, “No dice, huh?” She was looking voluptuous in this sparkling gold dress, the type of thing a person could only get away with on a day like today. She draped her arm over my shoulders, leaned her head against mine. It was affectionate, nothing more.

“It’s ok,” I said, “Can’t win ‘em all.”

“Back in high school, you used to come to me with your girl woes.” She sipped from a flute of bubbly wine. “You never were very good at keeping girls. But oh my were there a lot of them. Don’t worry about tonight, somebody new will come along, and soon you’ll forget all about what’s-her-face.”

She had me smiling already. Old habits. “That hurts, Ms Gautier,” I said, “There weren’t that many girls.”

She chuckled, turned her head to give me an incredulous look. “Every week, Raff. Every week you’d be sitting here in this living room, telling me about some new teenage crush or another.”

“Oh, well.” I blushed. “I just liked chatting with you, and that was all I knew to talk about.”

“We did have some good chats, didn’t we?” She grinned.

The song changed, something to slowdance to. The crowd thinned as people found quiet corners to make out. The click of glasses echoed from the kitchen, people pouring another drink. There was a couple in the easy chair next to us, wrapped deep in each other’s arms.

It just seemed like the natural thing to to, putting my hand on her leg, rubbing her knee. “I told you about everything,” I said.

She took another sip from her flute and whispered into my ear. “I also didn’t have anyone at midnight,” she said, “To kiss, I mean.”

“Oh,” I said, running circles around her kneecap, fingers brushing against the hem of her dress, “I’m sorry to hear that, Ms Gautier.”

“Raff,” she said, grabbing my wrist. Her fingernails were manicured ovals, painted in gold fleck, matching her dress.

“Yes?”

“Call me Natalie.”

I turned my head, our faces were nearly touching. “Ok, Natalie.” And I kissed her.

She kissed me back, but then broke away. We looked into each other’s eyes, letting the moment linger. Then she said, “Dance with me, Raff.”

We swung and spun, her arms on my shoulders, my hands on her waist. As I pressed into her, I could feel her heat, her tits. “You’re beautiful, Natalie.”

“You’ve always were a smooth talker.”

“It’s not smooth talk,” I said, “You were my first crush.” I twirled her around. “I never really got over it, either.”

“I’m too old for you, Raff.”

My hand slid down to her ass. “I want you.”

The song ended. And in the silence between tracks, we kissed again. My world spun, Joakim’s mom, Ms Gautier, her lips pressed against mine, so soft, so warm. My tongue in her mouth, I needed this, needed her. Her perfume permeated, something elegant, an undercurrent of lust. I pulled her into me.

“You’re enough to make a woman’s night,” she said, panting.

She let me guide her towards her bedroom.

I closed the door behind us and looked around. I’d never been in this room before, wasn’t sure what to expect. But it was dark and elegant, like the rest of the house of course. Solid furniture, a king bed dominating the space, a view down the hillside through the sliding glass doors.

“Are you sure about this, Raff? It’s–”

I pulled off my clothes, set them on a wicker bench in the corner.

Her gaze dropped to my crotch. “Fuck.” My dick swung between my legs, thick and long as a tallboy beer can.

I walked up behind her. “Let me help you with your dress.”

“You’re serious,” she said.

“Yes.” I wrapped my arms around her, one hand squeezing her round tits, the other sliding down between her legs. My dick pressed against her round ass.

She whimpered, then said, “Sit down, little boy.”

“I’m not a boy any longer.” I squeezed her harder, fingers dug in deeper.

“Sit down!” she snapped. I obeyed. It had been years since I’d heard it, but nothing had changed in her ‘mom’ voice. Sitting next to me, she curled her legs beneath her. “You always were a shameless little flirt.” She rubbed my chest, fingers running along my musles.

I said, “Do you remember back in middle school, you used to take us to the beach. You’d wear this wrap, like a real thin robe. Japanese print, see-through.”

She stroked my shoulders, my arms.

I continued, “And beneath, you had on your black bikini. The first time, I didn’t know what hit me, you were so sexy. We were swimming and I came back to the towels, I don’t know why, get a drink or something, and you were sunbathing, the wrap open, arms folded beneath your head.”

Natalie smiled, rubbing my leg, pushing my knees apart. “It was cute when I’d catch you staring.”

“It was those dark sunglasses, I thought you were asleep.” She brushed my skin with her gold fingernails, dragging them up my inner thigh, the touch so light, so teasing. “When you said something, I jumped, ran back to the waves, trying to hide my erection.”

She purred in my ear, “Did you masturbate, thinking about me?”

“All the time. Three or four times that night alone.”

“What did you imagine me doing to you?”

“Back then, I don’t think I even knew,” I said, “I just wanted to be near you, to see you undress.”

“For me to touch your fat cock.” She batted at my erection, pushing it down, releasing it, making it bounce against my belly. I gasped. She turned her back to me. “Unzip me.”

She stood, walked into her closet with a smirk. Came out a minute later and made my heart stop.

“This bikini?” she said.

I whimpered. “That’s the one.” Top stretched tight, cupping her large tits, pushing tanned skin out. The bottom, a narrow triangle of fabric, straps riding high over her hips. “I thought I remember wrong, no way would you really wear something so sexy.”

She did a twirl, letting her long dark hair loose. “I liked the attention. Still do.”

I stared, ogling, stroking my cock.

“You just can’t help yourself, can you?” She stood in front of me, pulled my hands off, then bent over, tits in my face as she knelt between my legs. “Such a strapping young man you’ve become,” she said, my erection swaying in her face, “So full of cum.”

I gasped as she reached out, teased my balls with her gold-painted fingernails. She slid them over my taut sac as she watched my cock twitch, me suck in breaths. Her fingertips orbited, slowly, gently, firmly. She pulled and squeezed. A bead a fluid dripped down my thick shaft.

“Do you like it when Mama plays with your balls, Raff?” She tugged and massaged.

“Yes,” I nodded.

“They’re so full and heavy,” she said, “Do you want Mama to drain them?”

“Yes,” I nodded again.

She squeezed them, hard. “Are you going to be a good boy for Mama and give her all your cum?”

“Yes,” I whimpered, “All of it.”

“That’s what I like to hear,” she said, grabbing my shaft, stroking its base, bumping its head against her tits. My pre-cum smeared against her skin, the sight made me delirious. “And this is what Mama likes to see, a nice fat shaft, so full its dripping out.”

“Mrs Gautier…” I moaned.

She pulled back, slapped my dick. “Call me Natalie.” Then she opened her mouth and caught my swinging dick with her lips.

My head spun as she took my length into her, sucking and slurping my manhood, her eyes locked onto mine. “Natalie,” I moaned.

She grinned. And then her mouth slid down my length, her tongue and lips getting me off with decades of experience pleasing cock. My shaft would disappear into her mouth with a wet choking sound, then she’d suck me clean as she pulled off, over and over. Her fingers curled around my balls, her fingernails returning, an unbelievable thrill.

She was tireless, never wearying, never slowing, knowing exactly how to build me up up up. And when I was right there, she pulled off and said, “Give me your cum, Raff.” She held her mouth open and stroked me with two fists, thumbs running up my underside.

I groaned, loud, and unleashed the biggest load I’ve ever made, a firehose between her lips. And that was just the first blast. She pumped, and I squirted, more and more. Then she closed her lips and swallowed. I dropped to her bed, nearly fainting.

She came back a bit later, makeup washed off, dressed in sweats, pajamas I guess. I hadn’t moved. She sat down next to me. “You ever need your cum drained again, Raff,” she said, “Just call me, I’m here for you. But now, I need to sleep, so get off my bed.”

I sat up and kissed her. “Happy New Year, Natalie.”

Source: reddit.com/r/sexystories/comments/rtthhr/how_i_ended_up_nye_in_the_bed_of_my_best_friends