>visit family during holidays.
>friend's mom comes over. She's friends with my parents. Since I was literally 3. I'm 25
Now.
>8 pm, everyone is chilling.
>I show up with gf. Haven't seen friends mom in maybe 10 years. I'm 25 now. Friend is a deadbeat. Will never see him again.
>his mom looks amazing. She's like 42. She had him young.
>"anon wow, you're like a grown man now!"
>"thanks" Kinda awkward.
>"you been hitting the gym? You're looking pretty buff. So HANDSOME. Your mom and dad mentioned you're doing that a lot?"
>see wine in her hand, sense GF getting uncomfortable, parents are around. Awkward as fuck. Try to get away ASAP
>"yep! It's fun for me."
>everyone sort of floats around. Watching some movie or something. She brings up again my body. I'm like, okay, I'm just gonna go for it. She's spending the night anyway.
>soon after I convince GF to go home because she has to wake early and has a far commute.
>text friends mom as she sits 5 feet from parents. "How you been? You know how hard it is to have a conversation with them. I figured texting is easier."
>":) I agree."
>"you look pretty good yourself by the way. What have you changed?"
>"thanks anon. I changed XYZ medication. It's helped quite a bit. No working out like you though :("
>"I'll put a routine together for you."
>she goes to bed down the hall an hour or two later. Parents go to bed.
>I sit in bed for an hour. Debating if I make the move. Never make the move.
Did I dun goofed? Or has my longtime milf fantasy found something that wasn't actually there?
>>678328874
>convinced your gf to go home
>she was clearly uncomfortable with the milf
You lucky she's not pissed off at you right now
post more of the chick in your picture
>>678328874
nah, you gotta play the long game. if you wanna man up and fuck the beast, get a phone number or find her on facebook, ask her to get a drink and catch up. Probably nothing happens, if something does, you got the jack pot.
>>678328874
Op, honestly I don't give a fuck about your problem but that chick on the picture is soooooo fucking delicious.
>>678329159
Yeah, I was not thinking logically whatsoever.
>>678329187
Done.
>>678329209
I got the number. It probably helps that her personal life is an absolute disaster. Been married a bunch of times. Etc.
>>678329371
I actually think I know that girl... Wow.
>>678329371
So I'm guessing this is the milf? is so, long game is good but don't make it the forever game.
>>678329508
Wish this was the milf tbh.
This girl is unsauceable
>>678329371
For fucks sake moarrrrrr
Sauce works too
>>678329573
How was the sex?
Fuck that's genius idea.
>>678329726
best pussy I ever had but it was also the smelliest pussy I ever had. Ended up having sex with her for a year or so before I moved out of state.
Did this gilf still,do
>>678330057
How'd you swing that?
>>678330248
Did some work on her house
>>678330380
Moar. How do you steer things that direction? Did she initiate?
>>678330057
tell us story
>>678330763
She bought a bathing suit and wanted to know what imthought. I don't need to be hit over the head with a hammer to know what she was aftet
>>678331219
You're how old?
>>678331440
39. She 59
>>678331548
Seems like a lot of older women can't get down with dudes under 30. They see them as children or something.
>>678330057
Gross
>>678329612
Damn, that sucks. Any pics of the milf then?
>>678330057
damn that's nasty
>be me go to friends house
>see his mom making dinner in the kitchen
>ask her what she's cooking
>she tells me stew then compliments me on my hair cut and shoes
>I say you're not so bad yourself
>oh stop it anon, you're too kind
>you see anon your friend says nice things to me
>aint he a charmer she says
>we sit down and eat after me and friend play games
>and then she asks him he can go to the grocery store to pick up some milk
>i offer my assistance to accompany him
>but she insists i stay back to help her do the dishes
>I stay back and as soon as friend anon goes out
>she goes up stairs
>5 mins later she calls me up
>naked laid down
>i fuck this bitch so much
>move into friends house at age 15
>his moms an alco/going through divorce
>drinking on a friday night
>drunk way to much
>end up in my friends moms bed naked
>last thing i remember was her landing strip
>>678332356
>last thing i remember was her landing strip
my sides
>>678329090
>mfw simpsons shitposting
>>678328874
I've got a story and I don't give a shit if none of you believe me because I crossed milf off my bucket list and I'm extremely surprised and proud of myself for it. Pic related.
>be playing csgo deathmatch
>hear female voice
>act like normal human and strike up non-sexual conversation
>add her on steam, she accepts
>shoot the shit for a few hours after
>tells me she's 42 and plays tons of games
>has 2 kids, going thru divorce, lives 5 hours away
>couple days pass and she tells me she's going to be within an hour of my work, 2 hours from where I live for a expediated medical administration training course for a week, staying in a hotel near there.
>she asks me out for a drink, i suggest sushi too
>get off work and drive 45 min and meet her in her hotel room, she gives me a big hug and tells me i'm hotter than in my pictures, (SHE IS TOO HOLY FUCK, see pic)
>i give her a 3d printed totoro from my 3d printer (she loves ghibli)
>we take off for sushi and have a great dinner, pick up beer after
>go back to her hotel (sorry neighbors)
>we watch some stupid shit on tv for a sec and get close and start making out and then I play with her big tits and go down on her and she starts screaming
>we fuck for a good long time and I know she came at least 3 times.
>we wash off in the shower and then get back into bed...
>her hand starts to wander, so does mine
>end up fucking her again and she asks for anal but I tell her next time (don't want to get my dick sushipoopi) (also was super tired)
we chat occasionally on steam but I don't hear from her much even though she said she wanted to see me again and that she touched herself to my pictures a lot after we hooked up.
>>678333408
More pics
>>678328874
>didn't cheat on gf
good man
>>678329531
Who is this lady?
>>678334562
Random whore
When I was younger I used to get fucked up everyday ( drink and smoke weed) One day I went to the mall to catch the bus, grabbed a 40 ounce and had some weed on me. For some reason I get off near a secluded looking beach stretch. Walk down the beach, eventually come upon a sexy Hawaiian Milf. We start chatting, she has the same kind of 40 ounce as me (Hurricane High Gravity, strong shit) We start chatting, her name is GIGI, she likes to smoke too. She busts out a couple roaches (Im young, broke and stingey) I ask her if she wants to go for a swim. She starts making out with me, I'm a little surprised. She said , well you were the one who was forward, takes off her top. Had her in the ocean, weightless, bouncing her fat ass on my dick. Couple older guys saw from far, were salty. Lol I tell her Ill call her back but never do. Damn she was thick...
>be 26, grad student
>live in apartment in two family house
>landlady is late 40's. got the house in divorce
>knows nothing about home repair
>I grew up with a father who never paid someone to work on his house. he fixed everything and expected me to help
>landlady mentions her door lock is broken
>pull it apart and fix it
>sink dripping. fix it
>now almost every weekend fix something, then sit and chat over wine
>she starts asking personal questions like girlfriend? sex likes/dislikes? (you're not gay, are you???)
>one night she just walks over to me and starts kissing me
>two seconds later we're in her bedroom
>decent body for having a couple of kids
>she unleashes a decade of pent-up sexual frustration on me. rides me, blows me.
>starts to become a regular weekend thing. skip the repairs, saturday night wine and fucking
>I graduate and take a job in another state
>talk back and forth
>year later I'm back in town for business
>she says come over
>she releases another year of pent-up sexual frustration on me.
>>678334222
>>678328874
Do it faggot, things like this don't happen every day
Post some more nasty filthy whores milfs.
>>678329499
of course you do, anon, I went to highschool with here, we all do
>>678329573
Smooth
>>678328874
I wonder if older women are really so easy as most of you try to sell this.
Are they really that cock-hungry that they give you their pussy for just a little bit of attention?
I'm 19 and just curious. Never did an older woman.
>>678328874
bump
>>678331886
They assume that by 30 you've got your fucking skills down. Below that you probably still fuck like a virgin.
>>678335873
It's not easy. There needs to be certain factors. They can't see you as a boy. They can't be married, 99% of the time. They have to be lonely. That's the archetype you find in this thread.
told this story before
>be 15
>best friend lives next door
>his mother is 35
>father died years ago
>mother is what you'd consider "loose". stays out all night, dresses like a whore (boots, leather mini, tight tops)
>mornings I go over to friends house, get him up and get him to school
>both me and my mom help him out to keep him on the right track
>one night go over to his house
>his mother tells me he's at his grandmother's house
>start talking to his mom. she's drinking wine
>she's telling me how much she appreciates what I do for her son keeping him in school, helping with his studies (I'm the smart one in the neighborhood)
>gives me a hug, seems more "love" like than a mom hug
>takes my hand and leads me into her bedroom
>starts opening my pants (I'm a virgin BTW)
>starts blowing me. I'm not sure how to react but damn it feels good
>she climbs up on the bed and lifts her dress up and pulls me on top of her
>she guides my cock into her and tells me how to fuck her (virgin, remember?)
>I last about 30 seconds and cum. feels like my insides are exiting through my cock
>take a second to recover, roll off and pull my pants up
>she tells me never to tell friend or my mother (they both ran in the same gang when they were young and she knows my mother would knife her for "raping" her son)
>from then on her hugs seemed different, but never did anything else
>>678333408
why the fuck do you live an hour away from where you work?
>>678328874
Those are some massive tits
I fucked a 32 year old married mother of 2 when I was 19. Fucked her multiple times in multiple places, including the family business I worked at (owned by my father). Probably had a good fuck buddy relationship with her for at least a few months. Best head I ever got, woman was a vacuum cleaner and loved cum. Tubes were tied, so was the first time I could cum safely inside a woman. She used to say that if my cum wasn't in her pussy or down her throat, she thought it was a waste. Never got to fuck her in the ass though. Sex was amazing.
>>678328874
Those are some massive boobs
>>678332256
>>678336853
did she work at your dad's business?
>>678335873
>I wonder if older women are really so easy as most of you try to sell this.
>Are they really that cock-hungry that they give you their pussy for just a little bit of attention?
>I'm 19 and just curious. Never did an older woman.
Women's sex drives peaks in their 30s b/c their biological clock is ticking.
>>678337688
So you say that I might as well go for it and approach older women?
Where my milfs at guys? I wanna she them milfs.
>>678338085
Online dating sites usually.
>>678338085
everywhere. not all of them dressed like whores though. some of them dress modest.
>>678337936
fuck it, go for it
>>678337666
No, she was a customer. It was a small computer store and I was the only tech, she came in for the company she worked for to get her computer worked on and she and I hit it off. Should would make up excuses to visit from work that were supposedly work related. She became friends with my Dad and I. I would invite her to hang out in the back room with me while I worked, and I usually got a blowjob while working on computers, sometimes she would wear a skirt and no panties and I would pump her pussy full of my cum and she would head back to work. She and I met up at different places too, fucker her at her house while her family was away once, fucked her there after her kids went to bed once (her husband was military and deployed and she had only married him because he helped her out of a jam years ago and she felt she owed him something). Fucked her in her jeep she had, outside a few times, etc.
Bumper
>>678339222
How did you make a move? Where?
>>678339222
>I usually got a blowjob while working on computers
How many computers did you fuck up because of this awesomeness?
>>678339222
AYO JODY BOY
>>678336779
>better payroll
>normal people
>not shit boss
>actually job one enjoys
choose one
why do you care if you travel 15 min or 2-3 times that? at least you are not a neet
>>678338402
>>678338429
kek. I didn't mean meet them. I'am too much of a beta to do that. I wanted some pictures to fap to.
>>678340212
I did the whole 2-hour 1-way commute for too long. Think of how much life you waste in traffic. 10 hours a week in your case. That's a full day that you could have worked. I'd rather get there an hour early and leave an hour late than deal with traffic.
>>678339498
Honestly hard to remember. She made it pretty obvious to me that she wanted me at the time but I can't remember the details of how exactly it started. It was a LONG time ago.
>>678340022
Lol, honestly, none. Different era with computers then, it was before infections and such were the primary thing so I spent a lot of time working on individual computers rather than short time on lots of computers. And she wouldn't blow me while I was working at the time, she would be my break, sit back, relax, watch her swallow my cock, nut down her throat, then get back to work. It was pretty fucking amazing.
>>678336779
>why the fuck do you live an hour away from where you work?
Pretty common way to enjoy nice life away from urban hive/prison. I like being able to swim naked in my pool, smoke weed in my back yard, and target shoot on my own property.
>>678339222
Trips checked. Someone has to keep that thing from healing shut during deployments. (That's why the Navy has multiple crews for most ships.)
>>678336853
How do you fuck a vaccum who's tubes are broken?
>>678342078
kek. A lot of people do the same things in the city too. I 100% agree with you though. Property prices tend to be cheaper too. I just would rather do actual work than be sitting in traffic all day (even if it means getting there an hour early)
>>678336779
I said WITHIN an hour. its anywhere from 30-50 depending on traffic. Detroit Metro area sucks.
>>678342282
Honestly if it was a "happy marriage" I would have avoided it. As it was, like I said, she didn't love him, didn't have her kids with him, he helped her out after she was on her own with her two kids, gave her a place to stay, etc, she felt she owed him, so married him but was pretty miserable, hence why she was wanting to fuck a 19 year old. Never met the guy, so pretty meh about the whole thing even now. As far as I know, she's still married to the dude wherever she moved to.
>>678342334
Very carefully. Her mouth was a vacuum...she could make me cum almost instantly with a blowjob, never had anyone before or since then that could do that, usually takes a lot of work. She was just amazing with her mouth and loved cum. And I mean LOVED cum.
>>678342929
>Detroit Metro
I can see why you want to live away from the city. In all honesty, there are actually some decent mansions (former car families) in your area for sale that are pennies compared to those in other major cities. The neighborhoods are pretty, meh, though.