We've all fapped once or twice over a MILF type, but do you think you could go through with it in real life...

We've all fapped once or twice over a MILF type, but do you think you could go through with it in real life? I have and the most memorable part is I can't get forget how unpleasant it was looking at her wrinkly face while breathing her rotten old woman breath all over me. Yuck.

Can you imagine waking up with a hangover and having to deal with this?

I've always had a fetish, even since a teen...Never have the balls to actually approach though. Drinking and clubs aren't my thing either, guess it'll be a fantasy for a while

i have but she was a young milf escort, like 30s. its was fine, she was pretty chill about fucking so it was ok. she was loose tho, not that im complaining

Eh, don't have to deal with pregnancy lockdown that's forsure.

>I fantasize about MILFs, but will never be man enough for one. I'm making this up to feel better about my shortcomings.

Fixed it for ya.

I think you mean "desperate." Old bitches are bottom shelf.

Are you talking about post-menopausal grannies? Fuck that shit. I'm not a complete animal.

SLIDE IT!

When I was 21 (I'm 36 now) I slept with a woman aged 48. She was a Jazz singer. I came twice.

Did snore a bit (although so do I, so I can hardly blame her).

Yes and no. I went home from a bar with one a couple of years ago. She wasn't anywhere near as rough in the face as OP but no oil painting either. We got to chatting, she was nice, talked endlessly about her recent separation. Felt a bit sorry for her, and then as the booze kicked a bit turned on.

Things changed for the worse when we started kissing (shudder) and went horribly south when I saw her naked. Sorry to admit I excused myself to go the bathroom and high tailed it out the door. Never saw again.

In the end, not worth it. All it did was hurt her feelings.

I suspect this isn't common user. I've bolted from what looked to become an unpleasant sexual experience more than once. Bad sex isn't that hard to get.

>typo
"uncommon"

How did you feel when sobered up and saw her in the light?

My first milf was when I was 16. She was 48. Fucked her good. Took a 10 year break with sex so I could be a single father. When my time was up I fucked a 50 year old woman. I was 36. I've been married for 6 years now to a currently 52 year old lady.

My.point? 50 year old miles like to fuck too.

Grats user, at least someone out there is living their dream

I don't think there's any question they like to fuck, but do you really want to look at an old woman's destroyed face while you're trying to get aroused.

Is your dream to fuck your mother?

If my mom's ass was a bit fatter, yeah probably

I have a few real life stories that are kind of hot
1/2
>Be an awkward 16 or something teen
>Horny 24/7
>One of my friends has a mom with ridiculous 80's country singer hair and gigantic tits an Appalachian draw and a rocky marriage
>stay at my friends house frequently sometime just drop by unannounced, his mom answers the door in a bathrobe, shes a 6.5/10 at best.
>play games all night with bro
>he goes to sleep early because hes in track and field
>Friend falls alseep early start watching cable
>find skinamax, get super horny. raging erection
>hear a small thump
>heart leaps out of chest
>look around in panic thinking ive been found out
>Its just his mom looking for something in the guest bathroom which has a connecting door through and extra unused bedroom
>Get curious
>stealth mode activated
>sneak in the dark twords the connecting door and peek through the door frame
>can see his mom bent over and right down her swinging cleavage
>erection intesifies
>start quietly masturbating
>my breathing gets louder
>she suddenly looks up at the door and says my fucking name
>hurry the fuck out of there
>she goes around the other way and sees me run into her sons room
>heart racing, freaking out
>she quietly lets herself in
>"user I need to have a word with you... now"
>swallow loudly, breath trembling, hear racing
>"O-Oh-OK"
>get up out of my sleeping bad
>almost shaking as I walk over to her
>My face was beet red I'm sure and she knows
>after a long conversation she tells me its perfectly alright to feel this way but its inappropriate to spy on someone.
>She asks me to go home and advises me to never tell anyone about what happened because it would hurt mine and her sons friendship but I am still welcome there.
>Scared out of my mind for weeks
>Neither of us tell a soul

>fast foreward a few years, in community college
>friend moves one state over, his mom still lives down the road there all by herself and god divorced after her son turned 18

grow up

Cont?

I lost my virginity to a 35 year old mother of two when I was 17. I had a lot of fun. She didn't have the best body, but cute face. Only real downside was that the first time we did it I could hear Dora the Explorer playing from the next room (her kids were watching it). It was a strange time, but I still went back for more on several occasions.

Where the fuck were these women when I was under 20 fuck...

the older the better for me. young women make me feel nervous.

Eh. It was fine.

I mean, hey, Gillian Anderson is 49, and just posed nude (for PETA sadly), and she looks fucking stunning. I'd give my right nut to be with her.

Same here. I can't talk to women my own age. I like being around my Mum's friends.

Really it's a time and place thing. Single moms are usually in a hurry and don't get much attention. If you attend a place they work quite a bit or visit similar places as them (i.e. grocery stores/markets), then a little attention can go a long way. It just takes some confidence and not looking like a total troll.

Well, her husband apparently cheated on her multiple times with a 19 year old chick, so this was like, her retribution. He had no problem with it at all and actually picked me up to go and see her lol. Felt dodgy at first, but wasn't in the end.

No shit. I was deprived!

I'm 27, gf is 46, would't ever fuck any woman under 40 (ex was 42, while I was 26). Best sex ever.

In my early 30s I fucked a mid 40s milf for a couple years. She had a tight and petite body though. Best sex I’ve ever had.

Idk I probably just don't have enough experience with cold approaches.

I used to do them, but the rejections got to me, then again I was like 17, things are a bit different now, maybe I'll have a better chance.

That shit is still engrained in my psyche though, which is probably why I haven't done any approaches lately

Fucked a 43 year old 5 times in one night.

She had a tight as fuck body, and a pussy that just dragged my cock in... almost painful but so fucking amazing

I'm 21, she kept hitting me up for ages after. Horny maniac

...

The majority of cases, it comes down to luck. More often than not, the situation just has to kind of present itself, and you have to nut up and take advantage of it.

My experience was sleeping with a friends aunt who lived down the street from me. She was over at his house once, met her, mowed lawns in my neighborhood, was invited in because she recognized me and it was hot as balls outside. She flirted a little bit, and then it escalated from then. Did it a handful of times, then I moved graduated and went to school. Wasn't the best sex of my life now, but back then it was pretty awesome.

I fuck them doggystyle. I dont look at their faces.

yeah, see that's way too old and low class. i wouldn't go anywhere near that.

Sounds like you're in the realm of fantasy now.

2/2
>in town for spring break, swing by to see her son but she says hes not gonna be there till tomorrow
>shes is happy to see me and offers me some food
>gladly accept because starving college student
>we get to talking about life and stuff asks me if Im seeing anyone ect
>never in a million years did I suspect she would ask me what she did
>"are you legal"
> I choke on my orange juice
>"to drive yet?"
>I immediately recall that one night I almost busted a nut on her bathroom door
>"yes ma'm, I got my licence right before I left"
>she smiles and asks to see see it, tells me I'm handsome in my photo
>Face gets red again start to chub up
and get embarrassed
>Think she must be fucking with me
>"are you seeing anyone"
>look right at her tits
>she smiles and says
>"ahhh I guess not, do you want to see them then?"
>She starts to touch the buttons on her blouse
>pounding erection
>I said "Amom, are you sure this is OK? I mean um you know?"
>"know what? Know that were both adults who can keep a secret right?"
>realize since I kept my mouth shut all these years I might have a chance with her
>become %1000 less nervous
>reach out and start unbuttoning her blouse
>she giggles and takes my hand away
>No, no, no I'm in control here, you just sit back and don't move until I tell you
>she stands up and reveals her big tits
>I actually drool on myself a little bit
>she giggles again, leans over and starts kneading my crotch
>"ok user you take it out now"
>she starts blowing me
>crazy hard
>trying to steady my breathing and enjoy this wondrous gift without cumming too fast
>tell her how hot she is (shes average at best)
>tell her I'm about to come
>she opens her mouth and I cum right. down. her. throat.
>she swallows most of it and chokes a little bit while laughing "been a while since Ive done that hahah"
>cant believe what the fuck I just experienced
>asked her why she swallowed
>"Well I didnt want you to mess up my hair sweetie"
>ask her if we can fuck someday

That puts you in a weirdo beta camp. Must be awkward socially.

sure you do. you pick them up without looking at their face, have doggy and go. no kissing. no talking. yeah, i'm buying that.

Banged this hot single mom on holidays recently. Best fuck I've ever had but fucked if I could deal with the baggage of kids, and all the other mom bullshit. Those tits though.

Fuck user, she's like the hottest chick I've ever seen on Sup Forums. Get the kids adopted out and keep tapping that fine ass.

Cont.
>she says "hmmm maybe darling, as you can keep a secret"
>nod my head in excitement
>we hang out for a bit and chat some more about life and stuff
>I go on my merry little way
>Kind of embarrassed around her son next time I see him, purposefully distance myself from him
>cant really brag about what happened
>if he found out there would be real problems
>a couple more years pass
>have a steady GF now
>mom tells me Amom was asking about me the other day so I swing by thinking I was going to get laid on the side
>see a new sports car in the driveway
>I'm polite and say hi but I can already guess the story, she is dating a new guy
>play it off real cool, meet him shake his hand
>she gives me a hug on the way out and whispers, your growing up to be such a man user and kisses me on the cheek

pic sorta looks like her

>I'd give my right nut to be with her.

If you did, she'd probably laugh at your half-empty sack and you wouldn't be able to get it up.

moar!

>Can you imagine waking up with a hangover and having to deal with this?

Yes. I'd deal with it again in the morning.

OP I have fapped -maybe literally- a million times to my hyper-teasing milf neighbor. She has a boyfriend even. I'm too big of a shy virgin to act on her obvious signals, so every time she visits and e.g. puts her foot on my thigh and starts wiggling it close to my raging boner I wait for her to leave and then go masturbate.
She's like 45 with wrinkles but I've seen her younger pics, fucking model.

How much did you pay her?

I love Goldie Blair

My dream is to fuck your mother

fuck, you know this rough bitches name. how sad are you

Tight pussy, extremely tight ass
Fucked all three holes

Nothing to do with her. Probably stole her pic.

>tight
lol, why do virgins always talk about pussy "tightness"

Don't judge, buddy. I think she's hot

Recent account, just two posts... yeah, okay. I'll buy that.
It's a Ruskie site. Fuckin thieves.

Dude, this is a MILF thread. MILFs have flaccid pussies like an worn out leather shoe. That and the wrinkly old faces caked in foundation is the main attraction. Go back to your trap threads.

are you like 100 years old

Good question. It was that way when I was a virgin, decades ago, too.

I had a 'very tight' girlfriend. It wasn't entirely pleasant.

fellas, who is she?

susie slopbucket, retired stripper from kansas

Lurk moar

generic garbage milf posted as a placeholder

ehh, she's all right. 8/10 for her age (which is probably mine), would motorboat and eat out

Sucks to be you

Fucked a woman twice my age (20 or 21, don't remember)

So you're 10?

Kek

Was curious about it after a frat bro claimed it was the shit. Picked up a cougar (or rather, let her pick me up) at local college bar, went back to her place, drank some more and pounded her 40yr snatch. Was... a weird but alright experience overall. Some turnoffs with wrinkles and drooping bellyfat but she was thicc in the right places and wanted it hard. A lot more padding than some skinny sorority slut and in the right places to grab or smack. Gave me this weird energy drink thing (small blue/red bottle I saw at a gas station in the middle of nowhere once) which made me feel like a drunk energizer bunny. Fucked her 3 times that night, passed out, woke and sobered up ~4am. I'm lying in bed naked trying to process what happened.

Started checking out the room, her kid's pics, half-empy box of Trojans, the same brand of body lotion my mom uses on the nightstand (bonerkiller right there). And her. She looked a lot better back at the bar. Now, smudges on her face and the sheets, all the wrinkles underneath and it looked like I licked and scrapped the foundation from one side of her face with my teeth. And yes, old lady smell, kinda a mix between piss, expired drugs and lavender. She noticed I was awake and we just started talking. Started getting emotional about how she she's not a slut and doesn't just pick up random guys. Then it got kinda sad, her divorce because of her drinking prob, ex got full custody of kids because her backstabbing sister hooked up with him and told stories in family court, how I kinda looked like her oldest son (creepy). Wanted to just get dressed and leave but couldn't remember how I got there or how to get back. Made me breakfast, drove me back to campus, bros all asked how'd it go etc etc. Gave an abridged version without the weird stories. Never got her number, she never asked for mine, never saw her at the bar again. Would've tried to hook up with her again if I did. Can say it was one of my most unique sexual encounters

Interesting.