Milly's Ass: Facesitting Paths

It's a quick tale, I won't argue with you about that. I'm sorry if you don't get every single detail, but I'll tell you what I remember.
But to make up for the brisk outline, I offer two different endings.
You can choose whichever one seems like it really happened to me: go with the one that feels proper. I'll never tell you outright which fate was mine, but I bet you can guess right if you're intuitive.
The journey to reaching my fate is true though. I'll be sure to note when my path splits into a lie or truth.
So.
I was 18, mowing the neighbor's lawn. She was fifty-nine if she wasn't already in her sixties. And she was a big lady.
Not tall, but average height, and definitely above average weight.
So. Mowing Mildred's lawn. I always called her Milly, cause she told me to, once when I was younger.
Anyway. She's fat, which I am very much on board for, with women in general. But Mildred "Milly" Hayes was pretty fucking chubby. She didn't seem old, just...sharp and sassy.
One day I finished mowing, went inside to say goodbye and maybe, hopefully, get paid.
Milly was tipsy, boisterous, and kind of like...into me...while she dug around in her blue housecoat for cash. Must have been drinking. She smelled like pina coladas or something.
Randomly, she flat out asked me if I was a virgin. I was, but didn't want to tell her that.
I lied, said I had sex once.
She asked me what kind of porn I watched, and I told her as I folded my arms, "I don't."
Another lie.
So, she grabbed me by the shoulders, and said, "What could I do for you, Jack, that would turn you on?"
I froze up, couldn't really think of anything.
Good thing I asked her instead, "What would do it for you, Milly?"
I had my moments.
"I like sitting on my men. Squashing, they call it. That's the kind of porn I watch."
Hell, I only watched basic porn. Just normal sex. But I did prefer big women, and porn was no exception to the rule. I thought it was coop that Milly liked porn too.
I didn't know how to respond to her statement. I just grinned.
"Jack," she said, squeezing my shoulders gently, "Would that be cool?"
I clued in that Milly wanted to sit on me, as in right now.
"Sure," I said, like a true dork.
Milly grabbed my hand, and led me to her leather recliner.
She pointed to the chair, so I had a seat. She turned, presenting her imposing ass, clad in stretchy pajamas.
Milly sat on me.
I had never had anybody sit on my lap before. She was so heavy that my first instinct was panic. But I realized I could still breathe, and it was just a lot of weight, and pressure.
But I was awestruck by how the moment itself was erotic in its honesty.
Like, Milly KNEW she was fat, and KNEW that sitting on me was a crazy thing to do. It was oddly degrading, sensual, funny, and most importantly, so fucking hot. My erection was pinned under her as it grew.
She didn't say anything, just sighed loudly in her contented comfort.
She smelled good, felt soft. She was warm, and alive. And I was buried under her.
I started to find it hard to breathe, and she noticed.
"One thing," Milly said without budging an inch, "Having your air restricted can be a turn on, too."
She was right. The discomfort, the pressure, and the smell of her sweat was all very much a turn on. But my airflow was pinched. And that was an amazing feeling.
She sat up, and I did too, trying to conceal my erection. She told me she wanted to start slow. That next week we'd try more things.
I said this was a short story, but it won't be if I drag out every single sexual moment that Milly and I shared.
But that afternoon was merely the first of many.
The next time I came over to mow Milly's lawn, we did something new after I was done with my lawn care chores.
Milly took me to bed, and removed her housecoat.
Bra and panties, the kind that older ladies wear. But Milly looked quite hot, despite the beige underwear set. She died her grey hair brown, you could see it in the roots.
She climbed on top, squatted over me, and sat her huge ass right on my face, like it was normal.
She smelled great, in a dirty, sexy way, even through the silky panties. I had a feeling she didn't görükle escort shower this morning.
She sat so hard I that I couldn't breathe. I think that was her intention. I kicked with my legs and scrambled to tap her thighs.
Milly sat up, and let me breathe. Then she told me to get naked, so I did.
She got me back in position, still wearing her beige undies.
Milly encouraged me to jerk off, and that was when I clued in to my good fortune: getting suffocated by Milly was the hottest thing I could imagine, and she wanted me to pleasure myself while under her. I had hit the jackpot.
In that novice way, even sex seemed like a runner-up to being smothered, even though I had never experienced the former.
I jerked off, and I came really quick that first time.
We started doing that every week I was over. We never kissed-- she just smothered me while I jerked off. She didn't even pleasure herself. Not when I was around, anyway.
Her only change in style started shortly after: she started to try harder to keep me suffocated by her huge butt. She also encouraged me to delay my orgasms as long as I could.
She got pretty hardcore with it. Sometimes it seemed like she was toying with the idea of smothering me to the point of blacking out.
I would make noises under her that scared me sometimes. Gulps and gasps, whimpers and shouts that were muffles by Milly's big bum.
That was hot too, just how lovingly heartless she was with it. Otherwise, she was so friendly, and chatty. Not after the lawn was done. She became a mostly silent, benevolent dominator after that.
We got really good at reading each other's cues. She knew when I needed air at the very last second. She never let me get too far gone.
I knew her pacing, and how long she preferred that I lasted under her. An average session with her was about two hours.
When I came, I came hard. Then we would dress, and she would fetch me a lemonade or bring out some cookies before I went home. It was perfect.
It was the best summer of my life.
Then disaster struck. Milly was going to move.
Her ex-husband was selling his place, and Milly bought it from him, and now she'd be selling this house that we had so much fun in.
I was bummed about her moving, until she invited me to move with her.
I literally didn't even have a job yet. I wasn't sure I could tell my parents I was shacking up with an obese, mature lady.
She suggested I could work for her, in the realty business, if I got my license.
I was too young, and I knew it. I had school to finish up with, anyways.
So I declined. She didn't seem too surprised, or upset. She kissed me on the forehead before she left. After she left, I watched her house go up for sale, a new family moved in, and I was forced to move on.
Five years passed by.
I moved out, got a job. But thanks to Milly, I was hooked on smothering. I always jerked off while holding my breath. I watched BBW facesitting porn.
But nothing was as good as the real thing.
I started drinking a lot in my mid-twenties. I didn't always make great decisions.
After losing my virginity the year I turned twenty, I started to sleep around quite a bit.
I had sex with some bigger women, but a one-night stand provides a limited time to convince a girl to sit on your face.
Heavy women didn't always feel comfortable with the idea.
Not like Milly, who was thrilled to relax her full weight on me.
In desperation, I used an escort once. One that specialized in facesitting.
It was only the one time, and I had to pay quite a bit of money. I couldn't afford the lifestyle I so craved.
But, it was still good times, even if it was just a couple hours long.
Her name was Mistress Sundress, and she was heavier that Milly was. About the same age, too. She always wore a sundress.
She sat on my chest, and my lap. She sat on my face, but not for long enough. It didn't feel intimate, but it was something, I guess. I wasn't allowed to jack off.
I had enjoyed my time with Milly more.
I drank more. I slept around more.
I met Tonya, a thirty-something bartender who was pretty dumpy, and I mean no disrespect, at all. She was fat, and unkempt most nilüfer escort nights we fooled around.
She was pear-shaped, and had a double chin. She didn't shave anything.
We had sex a lot. I felt comfortable with asking her to smother me, and she complied.
She was pretty submissive. I wasn't exactly an alpha male but I think I took advantage of her shy, subservient vibes.
I would get her to sit on me while I laid in bed, with her feet by my hips. She was fine with me choking and gasping for air under her unshaved ass and pussy. Part of the appeal was her lack of energy spent towards washing herself.
I convinced her to smother me constantly, and it started to be the only way I could finish. The booze probably didn't help with that.
I wasn't satisfied with simple smothering. I convinced her to fart on my face. That was probably my rock bottom. I got pinkeye often, and started to wonder what had become of me.
I had sex with Tonya on occasion, but I could never finish. You can't have sex and be butt-smothered at the same time, and that's why I suggested a threesome with her friend, Jo.
Little Jo was thirty, and short. Not curvy, but a girl was a girl. She slept around, so she didn't need much convincing.
We all got drunk, and I ended up with Jo riding my cock while Tonya sat on my face. I had a condom on, and finishing inside Jo felt fantastic as I nearly blacked out from Tonya's stinky smother session.
Then, Tonya went to rehab without as much as a goodbye, and I was alone. Jo didn't do it for me, skinny as she was. Cruel, but true. So I had nobody.
This is where things get weird and hypothetical. I was lonely, and I missed Milly. I was in my late twenties now, and I was a professional alcoholic.
I saw two paths before me:
The first daydream was a likely one. I drink more, I get more depressed, but I ultimately find someone else.
Someone like Tonya. A big woman who will smother me. She'll probably be a drinker too. And if I can't find a fling, I think I'd have to pay for it again. Find a cheaper escort.
Another option?
Stop drinking so damn much.
Get my shit together a little. Get a better job, meet a nice girl. A woman like Milly. Maybe I'd even see her again.
So it depends on you, don't forget: the faith you have in me as an unreliable narrator, in luck, in love, in the plausibility of the outcome, of what really happened.
Or didn't happen.
So that second version goes like this:
I stop drinking completely. Months later, I get in a car accident while sober. Go figure. I end up in the ICU, but I'm expected to make a full recovery. It's just a broken femur.
But in the meantime, I need tons of rest in the hospital as my leg heals.
Then, a miracle.
My nurse is very familiar.
It's Milly, and she's so happy to see me. We reminisce during that first day. She tells me how the property market dried up, and she pivoted into a nursing program.
I tell her about moving out, about my dead end job. I leave out the smother stuff. She kisses me on the forehead when nobody is nearby.
Sometimes, when the hospital is quiet, she smothers me in bed. Feasibility-wise, she's not able to mount me. But she wears soft shirts, and rests her heavy tits on my face.
Other times, she uses her soft hands to pinch my nose and mouth shut. She just smiles, and bites her lip as I twitch.
I get better, leave the hospital, and finally move in with Milly.
We start a real relationship, which takes a little bit to settle into. But after the initial awkwardness, it turns out Milly and I are very sexually compatible. But our favorite is still facesitting while she wears silky panties.
Even though it's still early in our relationship, I feel like this is just the start to a great story. Not the end.
So.
To play devil's advocate: how often is life so perfect?
I propose a more likely outcome-- the first path:
I don't stop drinking. Because it's hard. Way too hard.
So I move on from Tonya, and even the memory of Milly. I can't get a date. I settle for cheap prostitutes. High-end escort services are too pricey.
I start to pay for the services of Hilda on a weekly basis. Hilda is morbidly bursa sınırsız escort obese, and does as she's asked. She sits on me in sordid hotel beds. She sits on me naked, while I jerk off.
Her ass is saggy, and her skin is loose. Her asshole smells like cigarettes. I don't ask why. But she's heavy enough to get the job done.
I'm often drunk for this. Hilda is too. One night, Hilda passes out against the headboard while sitting on my face. My nose is crammed inside her thoroughly used, mature, ass crack as I jack off.
But when I finally come, I wait too long to try and move her.
As I shudder out an orgasm, I sense that her relaxed weight isn't something I can do anything about. My arms are pinned.
I suck in air, but saggy flesh is sucked tight against my mouth and nostrils.
I convulse. I realize the danger. Immediate, and immovable.
Hilda snores. I want to scream, but my head is cemented under the enormous ass of a heavy prostitute.
I gasp, and struggle. Kicking minus the screaming.
Then sensation of my impending death is all around me. I start to accept it as I lose myself, lose my life, lose it all.
I die within her darkness.
So, again, two fates:
Does Milly nurse me back to health? Does she enact our fantasy every day? Does she expertly bring me to death's edge, for our shared pleasure? Do we live happily ever after?
Or is that too much? To sappy?
Maybe that's the hypoxia-inspired fantasy my brain treats me with as I lose consciousness under the meaty ass of Hilda the whore. No offense. That's just her profession.
I admit both seem equally...extreme, with unbelievable aspects.
Maybe this story isn't a humble brag of true love. Maybe it's my death rattle, and you're the figment of a dying mind.
At least I died the way I lived.
Poor Hilda. I hope they don't blame her.
Maybe I'm just full of shit.
Maybe I don't want to admit things will be more...middle of the road.
Maybe its better to speak the truth.
The truth is, I struggled with the decision to cut out the booze. I ran many scenarios in my mind. Some of my worst case scenarios involved dying in a motel bed.
Some daydreams were more positive, and seeing Milly again was the most positive outcome I could imagine.
Ultimately, I decided to join AA.
I wasn't struck by a car. But I never saw Milly again. I guess she was always meant to ignite my passions, but never meant to stick around to stoke my fires.
I didn't end up dead under a massive hooker, either.
But I did meet a woman in AA.
Tessa.
She looked like she could be related to Milly, but unlike Milly, Tessa was in her early thirties. She said she never knew any Milly.
She was tall, blonde, and incredibly chubby.
We dated, and Tessa and I turned out to be a good match. We quickly bailed on AA, but we both enjoyed each other enough sober that we weaned off the sauce without much fuss.
I tried really hard to seem like a cool guy. A normal guy. I didn't tell her about my fetish for a year.
When I told her, we were about to sixty-nine. I told her my preferences so she wouldn't feel self conscious.
And so, my obsession bled into my relationship with Tessa too.
She humors me with some facesitting here and there, but we have sex way more often, and that's probably a good thing. She brings out the best in me, and I love being around her, even if she can never be as special to me as Milly.
So, three choices-- I lied.
I'll give you the Goldilocks options...
Too hot: I get my dream girl Milly, and all is well. Maybe too well?
Too cold: I expire under the weight of Hilda. It's a hero's death, of sorts.
Just right: Life is predictable, and Tessa and I get hitched. It's not a fairytale, but it's also not an ending. Just a humble beginning.
So, take your pick.
But me personally? I think that the one that gets me off is the one where my last moments are spent as spasms under hundreds of pounds of sleeping, female mass. Pinched between globes of gluteus, dying in that abyss of an ass.
But the romantic side of me still pines for Milly, and to once again be engulfed under the weight of her as she treats me like a throne. The goddess that I barely deserve.
I can still dream about my other lives. Paths not taken.
But being with her just feels...right. I think it's clear who I mean, but you think what you like. It's your fantasy too, right?
THE END.
(special shout out to...thatotherguy008...for offering me the framework of this story. Hope you enjoy bud!)