Tell us about it

Been with 4 who were over 10+ years older than me. No gilfs. Had more opportunities but never happened. The sex isn't always as amazing as people say it is. I’d say every time, a younger, attractive man is super validating to their self esteem. Coupled with not having dick/good sex in a long time, they’re easy.

Friends mom picked me up at Walmart a couple years ago. She was in her 49's and I had just graduated high school. Second female I had sex with, and a great fuck.

Pic related: that night

>>937894190
How did she do that?

>>937893194 (OP)
Can we get some more of this milfy lady

>>937894314
She picked up a case of beer and said "I'm going to the motel, you cumming?"

She even let me get one picture (no face)

>>937894521
so a couple years ago (2018 i think) i was visiting my sister in idaho with my mom, sister and dog when out of no where i felt like there was an extra presence in the house

On bali, during yoga camp, i was around 16, she was 30

>>937893194 (OP)
fingered your mom when she was drunk. she didn't smell so good.

>>937893194 (OP)
Lost my virginity to my best friend's mother. I was 15, she was early 40's.

>>937896364
How did that go down?

My babysitter milked me, i was 14 she was 23

I got to stay with my mom's best friend 5 years ago when mom and dad went on a trip right before Christmas.

She was 40 and I was too young.

My wife is older than me by about a month :)

>>937897100
You always remember your first. Been with 4 girls since and she was still the best.

(She'd be pissed if she knew I took this one)

Age gap not a big deal now, but I feel like I was mildly groomed as a high school freshman by a senior that was a notorious whore.

>>937897169
She'd be pissed if you took it from where? Google images? Ya fuckin goof

>>937897169
That's a hell of an ass anon. Did you eat it? How old were you?

Not like a major age gap. But when i was 21 this 29 year old asked for my number. 5’2 Latina with huge tits and a nice ass. Took her to a nice restaurant to get to know her. She must have majorly peaked in high school because she kept bringing up high school as if nothing had happened in her life in the last 10 years. She knocked 3 or 4 drinks and then demanded i go clubbing with her and her friends. She’s sloppy the whole night, talking to other dudes, telling me all the guys shes hooked up with in the club. I only stick around because i wanted to be nice and at least give her a ride home. She pisses herself on the dance floor and we get kicked out. She sucked me off while i drove her back home. Fucked her because she was begging me to stay the night. Blocked her number when she texted me the next morning.

Craziest blowjob I’ve ever had

Her son was spying on us

She is 52, I am 19.

She was pissed at her husband, and I was right place, right time

>>937897877
She is pretty hot too. And was nice and wet,

>>937896876
>>937897100
>>937897763
What happenned?

>>937897169
Great ass!

>>937893194 (OP)
>Tell us about it
She took out her dentures, I pulled out my wiener

>>937896876
>>937897944
We were playing doctor, she noticed that i got huge boner, she massages IT through pants and said she knows how to Cure that bit we need to hurry before parents come home. Took me 5 mins

>>937898005
WOW! Did you enjoyed? Did something happened later?

>>937898042
Well it was so good, especially when she did it with her feet for a while, that i wanted to Play doctor every time she was at our place. She only agreed Like 2 times more when i was extra naughty and she wanted to calm me down and put to sleep

I was in the military going through a divorce (typical for us), and using dating apps and trying to get laid as much as possible to get over my ex wife. Met up with this Filipina woman, I was 24 and she must've been...idk, 35+? Old enough to have two teen sons.

She's very specific about the time we can hook up, opting to drive to the hotel instead of being picked up at her place. Kind of had a feeling she was married but she never mentioned and I didn't pry. Went to the hotel, she tore off my clothes, we're making out, she's making "aye caramba" noises.

I'm hard as a rock sucking on her titties, but that all comes to a stop as I pull her pants off. Just a pure, nasty whiff of stank pussy. I almost gag, but I try to soldier through it. She puts a condom on for me and is already soaked, bent over in front of me. It's clean-looking enough, but the scent is just too much. I slide inside, and with each thrust it's like I'm pushing the odor out into the air and deeper into my nostrils. I try to power through, I really did, but it's too much for me, and I can feel myself getting softer with each thrust. After about a minute or two of this (idk how long, I think I hit fight or flight at that point), I pull out of her, take off my condom and run to the bathroom. I come out and she looks concerned, asking me "papi what happened? Did...did you cum already?"

I lie and say I did, and she just starts laughing. She's literally chuckling that I came too soon, so I say "okay, actually, no offense, but I lost my boner because it smells like death between your legs." I'm pulling on my clothes as I tell her this, and she looks baffled, bewildered, maybe even a bit bamboozled.

She asks where I'm going and I look at her weird and say "uh, back to the barracks so I can jerk off?" She asks if we can do this again sometime and I tell her no thanks. Hop in my car and drive away.

So that was one of my experiences with an older lady lol.
>pic unrelated

>>937898106
Did she made you cum in your pants with her hand both times?

>>937898175
Who is on the pic?

>>937898263
Once she did it with her foot, once with Hand, two times dryhumping doggystyle and missionary and once she put her hand inside my pants od my pajama

>>937898263
No clue. I just save pics to my massive porn file labeled "This is just porn"

>>937897763
>>937897944
Well we realized her teen son is spying on us, because we caught glimpse of him next to the slitghtly open door bit we decided to continue

>>937898348
Nice titties!

>>937898332
Did you cum on her hand?

>>937898388
Oh yes i did with a load i was saving for 3 weekd

>>937898453
How did she reacted?

>>937897286
Kek. The larp here is strong lately

>>937898492
She tucked me in, put to sleep and went to wash her hand laughing and smilimg

>>937898572
You think she liked it? Why didn't she made you cum more?

>>937898605
Well i came everytime, even during dryhumps. Well she definetly was surprised by amount of it i saved for her.

Yep. I was 18, she was 35ish with two kids. We were in a course together. She was just getting divorced.

It was great. She was a complete slut and wanted to fuck constantly. I think the idea that she was desirable to a younger guy really got her off.

>>937898692
Why she stopped?

Older cousin made sure that i know what sex is and feels like

>>937898781
Parents decided i dont need babysitter anymore when i hit 16

>>937898808
Details?

>>937898852
What a shame......
Did you tried to contact her?

>>937898866
When i was 15 and i told her i'm still a virgin she gave me godlike footjob, blowjob and she let me stick in few times

>>937897286
lmao

>>937894190
nice anonymity spic.

>>937898893
Yeah, but she said she isn't intrested, that i Had pretty okay cock but i was caring too much about her feet and that she did the same to almost all the boys she was taking care of

Closest was being 18 and I had a gf that was 23 and a pot head, cute slim blonde but had a skinny fat fridge body. Pussy and head was OK, shaved of course. Because squatch crotch is foul lol.
I was on a 6 month dry spell and was a lot more desperate than usual. Haven't really been that desperate since that time period, I was broke and having trouble with worthwhile income. She had her own place, tons of groceries and cold beer lol.
After that summer I got myself organized and finances in order, so I've never been in a desperate situation like that since.

>>937898175
Yeah that pic is about 10 yrs too fresh to be 35+ lmfao.

When i was 15 at concert, pissing next to the toilet stall because line was too long, this 30ish looking woman approached me, started laughing (she was drunk), asked if i knew that Man can use penis for something other than pissing, held my cock through the whole piss, then shaked it and jerked.me

Condensed version cause I'm on break from work.
>me recently turned 21
>at a bar, run into ex co worker from a restaurant
>she's late 40s l, light wrinkles forming on her face but still had a slender mild body, perky tits, peach shaped ass. Her face was almost 50, but her body was still 30 something.
>she's drunk and flirting it up, I flirt back
>she ends up grabbing my dick
>instant diamonds
>she asks if I wanna go back home with her
>shityea.jpg
>we're both drunk so we catch a ride with her sister and the sis's boyfriend
>me and milf and making out in the backseat
>I start to finger her
>completely shaved, smooth as can be
>sis and bf are up front, arguing over some dumb shit
>drunk ass bf jumps out the moving car, at 45mph
>he's fucked up, road rash everywhere
>end up in a hospital instead of that sweet milfs pussy.
>had to have a friend pick me up at the hospital to get me out of the situation
>never did get to smash

My only attempt and it failed miserably

Yes. Met her in London. She had a very big house.

>>937893194 (OP)
The majority of women I’ve had sex with were older than me. Age gaps have ranged from 6 months to ~30 years. All but two were prostitutes. Sex has ranged from outstanding to awful. Best was this girl who was 19 when I was 17. Cheated on my at the time girlfriend with her, and she let me cum in her, which was the first time I did that. She was also into being dominated, so I learned I was into that. Worst was this fat landwhale that edited her pictures on the prostitution website, so when I got to her place, I was immediately turned off. I already drove out there and had the money, so I did fuck her, but I only came once, couldn’t bring myself to do another round. I remember going to the mall after and walking around solemnly. I don’t have pictures of the first girl, but I can post the landwhales page if anyone wants lmao

My first time was with my mom's friend/co-worker when I was 16 and I fucked a 30+ year old chick who was hitchhiking when I was 17.

I've been a male stripper for the last 18 years, in the UK. Mainly, it's birthday parties and bachelorette parties (or hen parties as they are called here).

In some parties the ladies are all very well behaved, look but no touch.

But it's pretty common for the ladies to get excited and drunk and to start grabbing my dick. And once one lady has done it, others follow. Inevitably they start to jerk my cock and put in in their mouths.

Sorry guys, but if your gf/wife has ever been to a bachelorette party with a stripper, this might have happened. They cheer each other on and even the shy sensible ones start doing it from the peer pressure.

Last week I was working at a bachelorette party. The bride was korean so there were lots of Asians there, which I'm really into. They were really shy at first but once they got comfortable were totally wild. I ended up cumming in the mouth of the mother of the bride

>>937901251
why would he jump out the car

The first time I was 10 and she was 18. She was hot and the daughter of my mom's friend who I would stay with occasionally when both of my parents were working and not going to be home for days at a time. They were team truck drivers. She called me "quackers" which was the name of these duck shaped goldfish like crackers back then. Started off as cuddling on cold nights watching movies on VHS from Blockbuster. Started kissing and touching each other under the blankets. She started sucking my cock, I wanted to nibble and lick her pussy and amazing tits. Not a bad smell, just a bit like pee and a tart saltiness I liked. Had my first orgasms in her mouth. I figured out my post nut hypersensitivity was just like hers. Learned her clit was just a tiny cock like mine over her piss hole. So applied the same that worked for me to her. Started having vaginal sex with her within a couple of weeks of when the touching started. They moved away when I was 12. Years later, I found out it was because she got pregnant and claimed to not know who the father was, to protect me, and keep herself out of trouble. Didn't meet my daughter until she was 25. Next older woman. I fucked I was 16 and she was 29, my English lit teacher. She was going through a nasty divorce with her soon to be excop husband. We just enjoyed talking to each other, she was hot with massive tits and amazing thighs. Sex with her was mind-blowing even though I was getting around. We were pretty intense for almost a year. Longest girlfriend I had before my 20's. Her divorce went through and she moved several states away. I even road tripped the following summer to tear some off. We spent a whole week nearly fucking each other to death. Then, just stopped talking to each other after I went back home. That kinda stung.

>>937904909
He was drunk. They were arguing. Apparently he was talking to some other girl at the bar and his sober gf(she was the DD) saw him. I never met him before that night but I'm just assuming he was a dumb fuck. I really couldn't tell ya though. We were all just as shocked and confused.

A coworker who wanted to hang out with me (pic related. It's not her but she was identical)
I was too young, 18 to be precise and she was 30 if not almost. So instead of just have fun I had delusions about marry her and stuff. She started to have the same delusions, probably thinking that she would get rid of her promiscuity, and have a good like with a young man
Whatever, I did had previous experience with making out and grabbing tits, ass and legs, however I was a virgin. Not gonna lie, sex with her was amazing, even though I'm tall (6'3), and she was petite (4'11), it still felt great
My first time with her, I got hard after undressing ourselves and the foreplay. Then I took out my underwear, and started to stick my cock in her pussy. It was fairly tight and too fucking wet and sloppy. After a minute or two on missionary, we swapped and she was on top, on cowgirl position, I instinctively took her hands and interlocked our fingers together
>This is just how I wanted to have you, Anon!
After a while with her riding and me playing with her small tits, she told me to try doggy style. I laughed, and she was like
>C'mon, it feels good!
And so I put my dick inside her, and I can't describe how good it felt because she prostrated herself perfectly, I felt all of her nice shaped ass
After that we changed positions for like 3 hours, she put me a condom using her mouth, and I ended up cuming when I fucked her again in doggy style and I couldn't help it for how good it felt. And she wanted me to put my dick inside her again, and this wouldn't be the first time with her showing me that fetish
After that we had more sex, she gave me plenty of blowjobs, handjobs, but my favorite position was reverse cowgirl, I can't describe how good she was in that position
Anyway, as I said she liked to keep going after I cum. Many times she cleaned my cock with a towel and put it inside her again, and didn't care how horrible it felt to me. Two times she used her mouth, plain torture

Met her when I was 28-29, she was 16 yrs older than me. Been together for 6-7 yrs in total. Sex was cash, she was up for a lot of stuff, gave me my first blowjob while driving, loved to be eaten out, was exhibitionist a bit which was great by me since I am also somewhat exhibitionist. Even posted some pics and videos on our national forum. Eventualy got tired of her jelaousy, plus she developed bipolar disorder so I ended it and then met my now wife. She contacted me few months ago asking to smash, but kinda not worth it, think she'll end up spilling the beans. Haven't saved a lot of pics, all the videos are deleted. Pic related is her.

>>937907517
She was 45-52 and looked like in the pic? Definitely worth to smash

>>937907718
Yeah, you'd imagine having three kids she'd be looking a lot worse, but thankfully seems she has great genes.

Wasn’t an older woman but an older man, I was 18 (f) at the time and he was like 31 or 32. Went on a car ride with him at around 11pm and it started off like normal had some random ass small talk. Then he pulled into an empty car park and just turned to me and took off his seatbelt, locked the doors and told me to take my shirt and bra off. I was pretty scared so I just did as he said, he started groping me and kissing my chest and then he took off his pants and put my hand on his cock.

He made me jerk him off for a while before pushing my head onto it, made me deepthroat it n everything, I figured the way to get it to end quicker would be to make him cum, so I started using my tongue on the tip and he started to use my throat like a fleshlight, just completely fucked it, made my eyes water and tears running down my face, finally he busted but he didn’t let me pull it out of my mouth, he instead pushed my deeper onto it so I was forced to swallow all of his cum and clean up his cock.

Then he made me get out of the car and he drove away leaving me shirtless in a random car park at night.

I worked with an older woman for a couple of years in the alps, I was 25, she was 49. What started as a drunk kiss in winter, ended up in a year of sex. I would stay over during the summer, either at hers or where she was dog/house sitting. Might have only been a couple of times where I didn't cum inside her. Some of her friends would ask her if there was anything going on between us, but she would always deny it and use work as an excuse. Her son came out to visit once, I took him out skiing a few days, he was around the same age as me.

I was always really shy in school and lacked confidence, so never had a girlfriend growing up. This older woman was the first person I had sex with, really want to meet an older lady again, it was amazing! Taught me a lot in a short amount of time!

>>937893194 (OP)
Sadly yes. +35 yo, fatties and other ugly women should be killed as they are waste of space and oxygen.

>>937898175
Her peng peng smelled like Bagoong?

>>937893194 (OP)
Yep, I was 10 and my 19 year old babysitter let me fuck her one night. We were sitting on the couch and she looked at me, asked if I had ever touched a boob and then it went from there. She just got naked and started teaching me about sex. Let me touch her boobs as much as I wanted, finger her, and lick her pussy. Then she sat me on her chest and sucked my dick, then slid me down and taught me how to hump her pussy. I came pretty quickly, but it was my first orgasm with actual sperm, and I nearly got her pregnant.

>>937893194 (OP)
Most of the hookers i've been with have all been older than me. Oldest was a 40 something year old latina. It was nothing special. Condoms kill the sensation so that doesn't help

>>937896796
After she lost her husband, she sort of became wild, staying out all night. Me and my mother watched out for my friend (her son) and made sure he got to school and was fed. One day I went into his house and he wasn't there but his mother was. She basically thanked us for taking care of him, dragged me into the bedroom, blew me and rode me.

>>937893194 (OP)
I had a dream of a girl on her wedding night wearing a wedding dress, and she asked me to help her get the garter on.

>>937893194 (OP)
When I was 23 I had sex with a 37 year old colleague of mine after a work party. She was short, brunette, nice ass but no tits. We both got pretty wasted at the pub and when it came time to leave we both agreed to share a taxi because we lived pretty close together. In the car nothing happened, no vibe, nothing saucy just general chit chat.
My house was closest and when I was getting out of the car I just suddenly had the urge to invite her up. I asked her if she wanted to have a coffee and see my place (I had just moved in and wanted to show it off because it had cool architecture) and I think because she was put on the spot she said yes out of politeness.
We got up to my place, I put the kettle on and gave her a little tour.
After I made her a coffee, we chatted a little more and both sobered up a little. Still no vibe at all.
She asked if she could use my bathroom and then was gone for about 15 minutes. Then I heard the shower turn on. I wasn't completely sober yet so I thought fuck it I'll knock to see if she needed help or had spewed or something. I knocked on the door and she said "you can come on it's okay" and when I opened it she was stark naked and just about to hop in the shower. I was a little shocked and asked her if she needed anything. She just winked at me and hopped in the shower. I then started to strip off and was immediately hard. She said "oooh that looks like it's gonna hurt" and before I knew it we were both in the shower and kissing and fondling each other. She had a perfect little pornstar pussy. She gave me head in the shower for a while and then when the water started to get cold we hopped out, dried off a little and then fucked doggy-style on the couch. I was about to pullout and cum but she told me not to stop because she was about to cum too so we ended up cumming almost at the same time. After we were done she complimented my dick size, thanked me for the evening, got dressed and left. Then the social drama began lol

Other people's sex lives read like a foreign language to me.

Hey there, I'm a 20-year-old girl from the US, a little on the adventurous side, and I absolutely love the thrill of naughty chats! There's something super exciting about getting guys to lose control while I keep things fun and spicy. I'm a total flirt, and I can't resist pushing boundaries during our chats. I prefer this over the whole meeting-in-person scene since I deal with some social anxiety. If you feel the same and are looking for some steamy conversations, I’d love to connect! Hit me up on my app: S-o-p-hie xu l be r (just make sure to remove any spaces and dashes). Can't wait to hear from you!

I've never had a woman older than me, and I'm a 55 year old swinger with a slightly younger wife (52). I prefer the other direction, the best being a 22 year old when I was 52. That's how it's supposed to work, mein negers.