>>23587695
It's difficult to hook with a mature woman if your penis isn't erect. Sex with a soft penis is near impossible. Make sure you're hard before you have sex with a MILF.

you should continue after 2nd

>>23587695
I'm honestly curious about strategies. If someone has any london related advice I would be glad.

>>23588018
first: milfs don't want anything serious with a young guy. if she is clearly looking for something bull still hesitant, a line like "look i'm not looking to marry you or anything, i'm just looking for some fun" is good.

other than that just be charming and you need to come on to her, can't just sit around and wait. just go up to her and order her something to drink and tell her she's looking really fine.

Can someone please post a story. Ive been trying to ease into this one I work with. I'd love to read about others experiences.

Hooked up with a 39 yo and I was 24. She was super cool, friends with guys my age. A teacher. I didn't go to the school she taught at though. We just hit it off, next thing I know I'm sticking my dick in her hairy, yet groomed vagina. Woke up in her bed, she's on the couch with her 2 kids. Come to find out she had a husband. I felt bad but I didnt know. theres really nothing like a milfs skin. It's so fucking soft

>>23587695
Hey Op is back.
Wow this is a slow ass board.
I continue the story now
>answer her "ok we can try next time" like an idiot
>next meeting
>in her flat
>long hug at the start
>feel her boobs on my chest
>nobra.jpg
>being beta i don't bring up her offer
>it makes her even hornier
>after music
>sit beside me on the couch
>inching closer and closer
>"anon kiss me"
>her tongue pushes through my lips in my mouth
>make out for good 30 minutes
>she stands up an knees before me
>unzips my pants
>blowjob
>cum in her mouth
>do the same routine again 30 minutes later

She became my gf and we were a couple for a year.
Sex was better than with girls my age but not the best i ever had. She loved anal.
We broke up after i found out she was crazy.

So any other stories?

>>23590366
Read nigga

>>23590366
crazy how?

Cant be bothered greentexting.
Not just a hookup but I had a three year relationship with a 37 year old from when I was 18.
She was my music teacher in year 12. There was really nothing at all between us when i was a student up until the last few months when I got chatting with her at a school performance.
Things took a long time to slowly escalate but when they did it was amazing. She was my first everything, had only ever kissed girls before that.
Sex was absolutely off the wall, did everything, and it only got better as the years went on.
Every girl Ive had sex with since then doesn't even come close.
Had to break it off only because she wanted a kid and i didnt.
If the age gap was shortened by 10 years I wouldve ended up marrying her but we were just at far too different points in our lives.

>>23588018
From experience, they are out there. Sometimes on dating sites. I had one that came to me and wanted to do anything I wanted. She wanted to be friends and I did to, I'm not like most guys my age (22) she liked the way I looked and enjoyed my charismatic tone. I made her laugh and she made rocked my world... Very experienced woman. The bees knees....

I had a family friend who I was slept with for a few months when I was 20-21. She was 50

>We had been friends for years at this point.
>I was distant cousin to her kids (related to her ex husband) and had known them for years.
>we met on a school trip to england when I was 15
>she was the cool parent
>all the other parents were jealous and excluded her and kind of bullied her
>I organized a group of kids together to pool in cash and bought her something cool from a little shop
>close ever since
>ffw to 20
>me and my friends hang out at their house and drink almost every weekend
>she usually hang out with us and gets shitfaced
>one night I'm taking a pee and I hear noise coming from her room
>she is hooking up with my bff
>i drunkenly stumble in and try to join
>get rejected
>turns out they had been hooking up for months and nobody knew
>few weeks later friend starts dating his ex and she feels abandoned
>I'm almost black out drunk and stumble in her room cuz I heard her sobbing
>tells me how she feels dumped
>try to console her
>rubbing her shoulders
>slip my hands gradually through the front of her shirt
>doesnt stop me
>go full on and start playing with her tits
>"oh anon"
>somehow hard through the massive amounts of rum and beer
>starts grabbing my dick through my pants
>drunkenly fumble around her clit through her pants
>she starts moaning and I pull down her pants and start fucking her
>insanely wet
>when I tell her Im going to cum she says I can cum inside
>shes post menopause so fuck it
>cum so hard it leaks out her eyes

I felt so awkward the next morning, but she called me later in the evening and told me that we just shared a special moment between friends and that we could never do it again, or keep on going, and we would be friends no matter what.
I continue to fuck her for about 7 months. After a few months I start sleeping over in her room on a daily basis. It was great until the 6 month mark.

>>23591358
At this point I only had had a few relationships, none of which worked out
>Didn't know how to handle them
I> started getting possessive, and ignoring my friends
>She tried breaking it off sexually , and I was resentful
>She had a party at her house where a few new friend showed up
>She and her family all went to bed early
>After I went home they fucked up the house,
put huge ruts in her front drunk from drunk driving
>Threw a bunnch of shit in her pool (chips, paper towel, beer bottles, garbage) and drank all her liquor and beer
>She blamed me for the incident since I left them there alone.
>that was in 2009
>Still havent seen her or her kids again
>I have no idea if they know what actually happened between us
>or if they think she's still bitter about my friends fucking up her house
>the sex was great but I really regret losing her as a really close friend and her kids friendships as well

>Met a girl online when I was 20, she was 35.
>She is also Australian.
>We cam all the time, she loved to be submissive on cam, would do anything I asked.
>Do this for about 2 months.
>Tell her about my plan to go to Sydney (Already had it planned before I met her)
>She gets really excited, we meet up in Sydney at my hotel.
>I'm not even close to beta, but it was still pretty nerve-wracking to meet someone like that.
>She tells me it's been years since she had a real cock.
>Okay, I'm thinking. This just means I won't disappoint.
>I'm all demanding to her, tell her to get on her knees, which she does.
>I tie her hands up behind her back, she loves it.
>Fuck her mouth, not stopping for gags. Cum all over her face.
>I tell her to wait there, I then go and watch T.V for a bit. (I couldn't get hard again right away.)
>Made her wait on her knees for like an hour. She's moaning the whole time, begging me to fuck her.
>When I can get it back up, I fuck her mouth again. (Cum still on her face)
>When my cock is all wet I forcefully bent her over and spit on her ass.
>"I don't like anal, anon, you know this."
>I just ignore her, fuck her ass. I was being polite and went slow. She moans the whole time.
>"Anon, change my mind, I like anal."
>Pounded her ass at that point, lol
>Make her get on top, she tries going in without a condom on me.
>Tell her to stop while I put one on.
>"No please, I'm on the pill, I promise."
>Told her to fuck off because I don't know that for certain, put condom on anyways.
>Fuck her pussy with her on top, hands still behind her back, she's fingering her ass.
>She cums all over me, I couldn't cum yet because I came earlier.
>Say fuck it, take off condom. Blow load in her.

I still talk to her every now and then. I never went sight seeing in Sydney like I wanted, we just fucked liked animals for that week. Went back once to do the same thing. I'd still go again, shit is just too expensive.

>>23591421
I have more stories with her. Don't know how much longer I'll be on, but I'd love to share if there is interest, and I have time.

>>23591445
More stories!

>be 22
>move to small town for work experience
>struggle to settle in
>spend most of free time at library or bar
>meet mid 30s shot black haired latina woman
>"you're anon right? you just moved here from anonville, my brother and his family live up there. how're you settling in?"
>tell her that im struggling to settle in and that it's been such a dramatic shift in lifestyle that i cant seem to find anything else fun to do
>"theres plenty to do anon, you can start with buying me a drink."
>couple hours and 6 or 7 glasses of wine later we're dancing when a slow song comes on
>slow dance for the length of the song
>she looks up at me with her big brown eyes
>"anon can i tell you something?"
>sure anything you want
>gives me a peck on the lips
>small pecks proceed to full making out
>cab out to my place and make out on the whole way
>finger her a little in the back seat
>get inside and by this point shes saying some shit in spanish and im clueless but it sounds hot so i go with it
>start eating her out and shes moaning super loud
>says that she wants to suck my dick so we start 69ing
>start rubbing her asshole while i eat her pussy
>she starts deepthroating me
>she sits up and starts grinding on my face
>"anon im gonna cum anon im gonna cum anon imgonnacumanon dont stop anon"
>she starts to convulse and shake in fits of orgasmic pleasure
>"oh my god that was amazing"
>she gets off and i get up behind her a pull her ass up and push her face into the bed
>slide my dick inside her and start pounding away inside her
>"oh anon you're so deep inside me"
>more espanol that i dont understand
>start fingering her ass while im fucking her
>feel her starting to clench on my dick
>feelsgoodman
>"anon im close again, cum with me this time"
>tfw im not even close
>"aaaaaaanon anon anon im fucking ugh anon"
>more espanol that i dont understand
>"holy shit you're not even a little bit close"
>she got on top and started riding me
>fuck yes this is it
cont.

>sucking on her breasts while i pound up into her
>she collapses on top of me and starts sliding her pussy up and down the length of my cock
>stops while im half inside her and starts grinding against me
>"anon thats it keep doing that fuck im gonna cum again"
>she clenches around me and my dick pops out
>"anon i dont think i can keep up with you like this"
>dont worry about that
>i get on top and start pounding her furiously
>shes moaning and yelling things in spanish
>oh fuck THIS is it
>michael jackson's this is it
>here i cum
>feel her legs wrap around me and her feet lock at her ankles
>"inside. cum inside anon."
>"please cum inside me. i need your hot cum inside me"
>that sent me over the edge and i blew the biggest load in my entire life
>"aNON IM CUMMING DONT STOP"
>fuck her through her final orgasm and that was it
>"holy shit that was amazing anon"
>pop my dick in her mouth and she sucks me clean
>"anon nobody can find out about this, this is a small town"
>dont worry i wont tell anybody if you dont

i have more stories i'll dump a few more when i get time if the thread is still up

>>23591466
You got it.

>I tell her before I go my second time, she has to get another girl to play with.
>She is all freaked out, but I'm persistent.
>She meets a girl on Craigslist, they became fuck buddies like a month before I arrived.
>I would play with both of them on cam.
>This time, she picks me up from the airport, with her new friend.
>I kiss her pretty passionately when I see her, her friend looks at me kind of jealous like.
>"Want one too?" I ask her friend.
>She perked right up and went for it (cutest thing ever, it was pretty nice.)
>I tell them no bullshit, we check into the hotel, and I want to SIGHT SEE. Didn't get to last time.
>Go to my hotel, check in for all three of us, go upstairs to unpack.
>Her friend pushes her down on the bed and goes ham making out with her.
>Okay, at this point I'm thinking, whatever. One fuck, then sightsee.
>Her friend's backpack is literally packed with nothing but slutty clothes, and toys.
>"You're going to dress that slutty the entire time?" I asked her.
>Apparently they both decided that before hand.
>I figured out at this point, my friend is still submissive as shit, but to the other girl as well.
>She proceeds to tie her up in a weird way. (I don't really have experience in BDSM and shit, I'm pretty vanilla but with a slight dom side.)
>Her friend looked at me kind of upset, "Is it not okay if we dom her together?"
>I'm not an experienced dom by any means, so whatever.
>She plugs her ass for the entire time.
>I started fucking her pussy without a condom (I know now that she was on the pill, so no worries.)
>She is wet as fuck in anticipation, and how her friend tied her up. (It was like with her legs tied to the bed wide open and her arms on her neck?)
>Her friend is sitting on her face making her eat her ass. Weird, but okay.
>Her friend turns, forces to have her pussy licked.
>I'm still just fucking the pussy.
>Her friend looks at my cock, obviously wanting it.

Will continue.

>>23591553
>I offer let the friend have a turn at the cock.
>"No, not while I'm in a dom mood.
>Untie my friend.
>Bend her over, take the plug out.
>They start to 69 while I fuck some ass.
>Cum in her ass, other girl catches it. (Hottest thing I've ever seen, probably will never see anything better.)
>They continue to play while I showered.
>I go sight seeing with them while they are dressed preeeeetty damn slutty.

It was a fun week. I fucked both of them a lot. This time, I felt more like a third wheel but it was okay. Whenever I fucked one, the other didn't want to be fucked. Which was kind of weird, but whatever.

>>23587695
if you are after worthless sex
any age is fine

if you are interested in a relationship
and perhaps a family
the girl must be in her 20's

>be 19 year old me
>serving in Okinawa
>meet pretty decent looking local girl at bar
>we talking, she speaks amazing English
>think nothing of it
>see her again a few weeks later and she had cut her hair
>find out she is 37 and married
>think nothing of it
>we get intimate and fuck
>it was kinda meh
>find out she was using me to get back at her husband who is an American and cheated on her

>>23591500
>>23591567
Great stories guys, I'm hoping I can get a milf for some nsa sex in my area.

>>23591421
Cool story bro. I'm game for more.

OK anons i need your help. This 38 year old woman wants to fuck with me. What to do? Im 18. She is decent looking and i kinda wanna fuck her. Is it a good idea. She is also married but her husband is ok with it.

fuck her, jesus christ mate if her husband is letting her do you then you cant lose

Ok I got one. That happened to me a couple of few year ago

> 23 7/10 working as waiter on island
> Start fucking 18yo 7/10 dark haired white skinned Goth chick. Hell of a tight pussy.
> Over weeks, stole her virginity & emptied a load of my juice into her fine dark, long haired but sweet tasting young pussy
> Made her come so hard she squirted all the time. Urinesmellnasty.jpg
> Convinced her to try anal & went to town on her tight asshole over & over again
> Summer season's over & I'm thinking of leaving for the winter snow season
> But tall posh english Milf starts work with me & I follow her fine long brown haired Amazonian ass around like a dog in heat
> Milf's 35 but hot to trot
>Start flirting with Milf who's hot for it. But not too much to lose Goth chick
> Milf chick saying dump Goth & fuck me.
> Milf flashes to me her amazing tits & lets me touch em. I'm like whatdoman.gif Fine Ass vs Old Fine Ass
> Catch boat to mainland for party weekend without Goth Chick but stay at Goth chick city apartment. Nice freebie!
> Meet up with Milf & get drugged up severe
> After heavy clubbing fondles and anchovy fingers, Milf drags me by my boner back to Goth chicks place & we just go fucking mental on each other
> Fuck her in Goth chicks bed. Feelsbadman.gif not
> I went down on her like a dog eating hot chips.
> She actually had muscles around her pussy
> Amazonian Milf has finest toned body & round perfect ass
>Milf's panting like dog when I'm pumped her hard & blow my load deep into her pussy
>Her pussy was big but she squeezed her thighs to make friction
>Fuck her 2 more times, sleep & wake up in morning
>Milf wakes drugged up, rolls over & says fuck her asshole
>It was hella tight man. BlowQuick.gif
>She squats & lets my cum drip all over Goth's bed. SickbitchdoesSnailTrails.jpg
>Milf fucks off in cab & 10 mins later Goth chick appears to surprise me
>Spend day eating out her hairy pussy as my cock was so raw
>Got away with it
>fuckthatwasclose.com
>Best time ever

Bamp

>>23591500

around 7 or 8 months later
at this point we're definitely more than friends but not quite a couple. she stayed at my apartment quite often though.

>around xmas time go back to home city to spend time with family and such
>"anon i dont really have many people i want to spend this time with. my brother and his family go overseas so there isnt very much for me to do"
>offer to take her to my parents for xmas
>"are you sure? you know what that makes us though right?"
>seemingly fine with being official with this woman that lets me stuff every hole she has with my dick
>next day pack bag and drive up to parents house
>get a few blowjobs during the drive, finishing in her mouth and once on her face
>get to mcdonalds and she wants to keep the cum on her face while she goes to order
>she goes in
>dick is diamonds
>so fucking turned on by this
>follow her in and she just ordered
>take her to bathroom
>pull her tights down and proceed to push balls deep into her tight slit
>pound her hard and fast while my hand is covering her mouth
>dont last long at all
>bust a thick load deep inside her
>she sucks me clean and then goes back to get the order
>get back to car and eat
>drive was fairly relaxed, some music and singing
>she fell asleep for about a half hour while i was driving
>then we arrive at my parents house
cont.

>>23591567
dang dude. How did you meet her?
How can I meet a girl like that?

>first few nights were fairly chill
>couple nights before xmas was when shit kicked off though
>found out my mum didnt like my girlfriend
>found out my dad absolutely loved her
>disregarded negative shit because its xmas time and nobody needs that vibe
>that night Gabi and I were making out in my old room
>hear a knock on the door
>mum comes in to talk to us
>ohgodnopleasenogodno.webm
>we stop for a bit except Gabi reaches under my briefs and starts rubbing my cock
>mum is standing there talking to us saying that if Gabi makes me happy then she's happy
>blablabla wasnt playing attention was trying hard to not bust all over myself
>Gabi kisses me on the cheek and quickly whispers
>"cum for me"
>fuckit
>proceed to ninja blow load all over my briefs
>mum says that if we ever need anything at all that she's only a phonecall away
>thanks mum
>doorshutting.flac
>she pulls her hand up and licks it clean
>flip her over and start eating her pussy while her ass is in the air
>quickly return to semi-hard
>she says she wants to try something different
>puts on some stockings and starts giving me a footjob
>not really doing it for me
>starts fingering herself while giving me a footjob
>okay thats doing it for me now
>say i wanna fuck her and she doesnt let me
>start begging to fuck her and she starts teasing me
>after some soft teasing from her feet, she gives me the approval to fuck her but without the use of my hands
>fuck yes
>shes bent over slowly rubbing her clit
>i grab my cock and she pulls away
>"no hands mr."
>okay.jpeg
>harder than i thought it'd be
>finally got the head in and she pushes back into me all the way
>start moving in and out of her tight wet pussy
>my cock is glistening, thats how wet she is
>start pounding faster and faster
>then she starts whispering shit in spanish while telling me to fuck her harder
>push her head into the pillows because shes getting way too loud and my parents are 2 rooms over
cont.

>she starts rubbing her clit and before long she cums and forces my cock out of her pussy
>"fuck anon do that again, no hands" followed by more espanol
>push slowly into her this time
>wtf is that
>shes suuuuper tight this time
>espanol followed with"ohhh fuck im so tight you feel so big inside me anon"
>she says to go slow
>fuckthat
>start pounding in and out of her and she stops functioning
>wriggling and convulsing in what i imagine are fits of orgasmic euphoria
>pull out and this white creamy shit comes out of her pussy
>???? but i didnt cum
>"fuck anon i wanna suck your dick, let my pussy rest for a moment holy shit that was intense"
>shes still shaking, legs crossed and her breathing is really shaky
>fuck she just came hella hard
>feelsgoodman.png
>she deepthroats me instantly and starts trying to swallow
>shit i never last when she does this
>pull out of her mouth and turn her around
>"anon ive barely recovered and you wanna fuck my pussy again?"
>you have no choice here
>grab her ass and pull her backwards onto me and start sliding my whole cock in and out of her slowly
>"aaaaaaaaaaaNOOOON OH SHIT"
>feel this wetness at my knees
>think nothing of it and it mustve just dribbled down from my cock
>"anon i just squirted"
>start pounding even faster and cover her mouth so she cant wake up the parents
>you know that feeling when you're about to cum and nothing can stop you? like a lion could be charging at you and you're balls deep about to cum and not even that could stop you
>the door opens
>my dad walks into the room to ask for a lighter
>push deep into her pussy and cum uncontrollably and collapse on top of Gabi
>Gabi is at this point speaking in espanol and saying things that make no sense while shes having a mini seizure with the biggest smile on her face
>and my dad sees the lighter, walks over to the night stand literally a step or two away from us and grabs it
>"thanks" as he shuts the door
>roll off of Gabi, pull the blankets over us and pass out

33/F here
Hooked up with a 20/M. It was absolutely a waste of my time. He didn't even last a minute. Literally two pump chump.
Now he wants me to train his girlfriend. I said no. There's no sexual reward for me, and he can't satisfy me, so why would I engage in a training threesome for kids? Jesus christ.

>>23596362
And then there's 20 year olds like me that nearly can't cum in those fucking dead fish 18-22 year old girls that think just them lying around passively is already more than good enough and who are not able to do anything else.

>>23596368
THIS. 32 M here and I feel exactly the same. Give me 30s+ only, fuck that young princessy dead fish shit.

>>23596371
>tfw never fucked an older woman
I'd like to though. I remember, just like 3-4 years back I was like "ugh, they're all old and shit".
But now, when I see 30-40 year olds? Daaamn. Especially because they should at that point have realized/learned what fucking means and arent just letting themselves get served all day

>>23590824

Crazy like literally all good/hot women are, anon.

>>23596362
I bet he didn't even eat your pussy...

>>23596368
This guy actually told me he hardly ever came during sex. He talked a really big game and said he was interested im being my sub, which is why I gave him a shot. Sweet kid, but he had nothing to bring to the bedroom.
>>23596396
Nope. It went
> Kissing, me biting, slapping, roughing him up
> Noticed he wasn't getting hard enough, so I blew him and he fingered me
> got up to get a condom now he was ready, he puts it on
> I bend over with my hands on the wall and tell him to fuck me
> he does, seems to tire in that position, so I get on my back, put legs in the air, and tell him to fuck me in the ass
> he tries but isn't hard enough, I notice and tell him
> he admits he came while we were standing up and though he could just keep going
> no orgasms or marathon hole fucking for me

I wasn't nasty to him after. We talked and all. Nice guy. Zero stamina.

>>23596486
I'm >>23596368
I know everybody always says they hardly ever cum, especially at my age, because "lel I can fuck so long bby".
For me, it's actually a chore. With my past gf, I hardly ever orgasmed because she became sore and came fairly quickly, so she was so sore I had to stop before cumming like 50% of the time. At least she did the good old courtesy blowjob after if I didn't.