>>937145423 (OP)
My first experience was with an aunt who was in her thirties when I was 6

>>937145423 (OP)
Yes, that's a normal day for me. I'm 41 and my girlfriend is 66.

>>937145423 (OP)
I'm 48 and I'm dating a 60 year old who looks like pic related. We haven't had sex yet but it's bound to happen. I'm hoping she let's me call her Mommy during sex

>>937145658
When I was around 27-28 I had a threesome wih a woman age 23 and a woman age 46. Shit was cash.

>>937145423 (OP)
Six years older is old enough? Lost my virginity to one last week

>>937145423 (OP)
No I'm still a virgin, but I'm 21 and hoping my first time is with a older woman.

When I was 17 I met this girl on meetme. She invited me to her house for a party she was throwing, and to fuck. When I got there it turned out all her photos were from a time when she wasn't fat as fuck, as in person she was fat as fuck. I decided against fucking her but still wanted to get drunk because I was 17 and times you can get drunk are limited at that age.

Her mom was one of those moms that party with their daughters and was thinner and overall more attractive than said girl. She was immediately attracted to my long hair and was drunk enough to start laying on the honey thick as soon as I entered the party. She started feeding me 99 bananas shooter after 99 bananas shooter while crooning over my hair while the girl pouted, and when I started to get retarded drunk off them she then explicitly said she would totally fuck me, and I in my inebriated state said she should. She grabbed me by the hand and led me to her room while her daughter protested loudly and broke down at the sight of this happening. My phone was going off like crazy, missed calls from her and texts saying "please don't fuck my mom, what the fuck, etc." and continued doing so while I gave her mom a nice 17 year old mediocre dicking, and then the bevy of 99 bananas shots finally really got to me combined with the motion of my missionary'ing her, and I threw up directly on her face, collapsed next to her while she freaked the fuck out from stomach acid in her eyes running out of the room, and blacked out shortly after.
I came to on a pile of my clothes in the corner of the room. I think the mom went to sleep on the guest bed or something so I just hastily got my clothes on and saw myself out. I still remember the death stare I got from the fat girl as I tried to nonchalantly shuffle my way out the door into the winter night to wait an hour in the snow for the bus home.
Found out through FB mutuals that the fat girl overdosed a few years later.

>>937145658
How is your relationship with her now

>>937145423 (OP)
Lost my virginity to a chubby mid-30's Korean co-worker during an internship.
Fucked her in her mini-van and she drove home to her husband and kids with me dripping from her.
I've had bad yellow fever ever since.

>>937146746
It's much of a muchness. The advantage of someone older is they know what you don't.

>>937147195
Non existent.

Fucked my gfs mom once

>>937145423 (OP)
Yes all through out middle school. I had this neighbor who was a total slut. My parents did everything to get her out of the neighborhood. but she stayed. Kept sun bathing topless in both the front and side yard.. and She was the very first women i got to have sex with. Up to that point i was ether getting hand jobs from my friend or blow jobs. She just outright asked when she spotted me. I said yes we went in her house and fucked right there in the hallway on the stares. I dumped my load all over her tits.. She thanked me and said i was more then welcome to come back anytime. and i made sure to take her up on that one for sure.
I got to fuck her in her ass why this other guy fucked her pussy.. I dumped my load in her ass.. I got to hook up with this women till the 9th grade when she left out of no where not saying a single word. just got in her car left everything that was too large to carry in a car . Still no clue what happened to her..

>>937145964
>I'm hoping she let's me call her Mommy during sex
At 48? What the fuck is wrong with you?

When I was 20 I dated this 31 year old for over a year because initially she could buy me booze. She had been divorced a couple years, no kids living with her parents. Pretty good shape, b cups and a fat ass. I loved her hairy pussy and she let me creampie her endlessly and never got pregnant. If I threw her legs back behind her ears I could make her squirt. Let me fuck her in the ass. Total slut. She turned into a psychotic alcoholic when I tried to end things with her though. 10/10 would do again. I looked her up on Facebook a while back she married some old dude with teenagers and is embracing the stepmom life.

About to

>>937145423 (OP)
I fucked this 38 year old blonde when I was 22. Big tits, almost hour glass body, nice plump ass. She looked young for her age (Looked 25-26) and holy fuck she was such a freak. She begged me to cum inside her mouth. I also called her all kinds of names like slut and whore while she called me daddy. I also fucked her raw and creampied inside of her. She eventually moved out of state but fuckk I still think of her because she def left a mark on me

>>937145423 (OP)
Not yet, but I will soon. I'm 27, currently seeing a 47 year old. I can tell she wants it, I'm looking to set up the opportunity to make it happen soon.

>>937145423 (OP)
Almost and I'm still so sad it never went actually went anywhere
It wasn't even that much of an age difference she had just turned 31 and I was 25 but she kept hitting me with the ol' "oh im so old you don't want a woman like me!" And I kept reassuring fine shit that I know what I want and even if she wasn't dtf I was gonna keep flirting with her and I guess she really liked the attention because we were really close during that time. She even gave me some nudes at one point and tried to play it off in a joking manner like "this is crazy no way you actually want this~" but she even gave me like a strip tease video and I lost gallons to that shit and then one day her back was sore so she asked me to give her a massage and she let me touch her butt and it was very soft.
The furthest I got was one night I went out dancing with her and we had a really nice time and when she was dropping me home I kept joking about her at least giving me a kiss goodnight and she actually did.
Then a few weeks later I guess she was desperate for some action and hooked up with some bald nigga and then I moved out of the city so I lost contact with her
:'(

Handjob From my drunk auntie "to Reach you something about life"

>>937145423 (OP)
I was 16, and she was 19. And another lady when I was 20, and she was 27.

>>937145423 (OP)
yeah it was terrible and she ruined my life. her body was a bit of a horror show and her kids were messy and her brain was beyond fried from all the fuckin stuff. my life was so fried but then it got a little tolerable so I was idk feelin good and what went from hanging out at her place while even her ex current bf was also there ended with idk everyone dead

One time in high school I went to visit a friend but they weren't home but their mom was and mom was VERY excited to see me gave me a hug invited me in for tea it was nice but my friend wasn't there and her mom didn't have pants on so I left and yet still the next day in school she hits me with "Dude wtf are you hitting on my mom?"
Like damn I guess I should've if she was gonna snitch anyway

I'm 22 my gf is 28.

Went to a friends bday party and his girlfriends mom was there.

I alpha’d at the second table and she came over. Ended up making out with her infront of her daughters at the next bar.

It became wildly sexual and her bf never found out. My golf group did though and they were raging.

I hear she’s still with the bf, but I’m not touching that. Apparently he’s a jealous guy.

>>937145423 (OP)
Danni Ashe is so goated.

When I was twenty I was working at a grocery store and the lady that ran the flower section was always flirting with me. She was a 42 Hispanic chick with a slim body and a rocking ass. I finally let her convince me to go to her home during a lunch break as she was right down the road. 30 seconds after we got inside she was all over me. I ended up fucking her on her daughter's bed. Damn near blew a load in her before my sense of self preservation took over and I pulled out and nutted on the carpet. Her ass was great, but her tits weren't. Still a pretty good lay and for a twenty year old barely-not-a-virgin it was awesome. I expect I was lucky as fuck that I didn't pick up an STD.

>>937146992
That is honestly really tragic.
Not for you, but for the daughter and mom dynamic

>>937157783
Where did you cum? On her hand? Your belly? Her hand?
Was she fully clothed or half naked?

>>937145423 (OP)
My step-mom came onto me while she was drunk, but I pussied out

>>937163530
Was there any awkwardness after it happened?

>>937164774
No. I didn't understand it at the time, but I have a bad habit of going through people's drawers and I found a prescription for Xanax in her bathroom drawers years later. She was mixing alcohol and Xanax, which fucks with your inhibitions and your memory. She never brought it up, and neither did I.

>>937157783
Sounds like she was doing it for herself

>>937145423 (OP)
Had sex with a mom only because I lied about my age on a dating app. Had enough facial hair to look older than I was and after two dates she took me back to her place since her ex husband had the kids. Was incredible, but I freaked out after that she might find out my real age and ghosted her.

>>937145667
damn I'm 26, i hate being alive but there might be hope

>>937167117
How old were you?

>>937167363
Had only just turned 18 after our first date. She thought I was 29.

I’m 32, it’s was with a 42 year old women from my work. She used to be an alcoholic and got clean 8 year prior. We talked a lot at work and it raised some suspicion. We had such a good thing going on, that I went to rehab too. Once I came back to work she was overjoyed to see me and when I told her where I had been and that I’m clean, well you could guess the rest. Thin and horny, just like me.

These threads always bring out the larpers and the hiding schizo.

Fucked my ex mil, 58, I was 32

When I was 30 I spent about a year fucking this 46yo milf

Was starting college and there was a sudden boom of black women on my area. Go to my Walmart see this black granny massive ass white short hair wearing see thru leggings. Small crop top. Was staring at her ass. She noticed I freak out because she calls me over. Asks me what did I think of her body I was apologizing but she said I didn't need to. I tell her she looks real hot. I was damn horny. Tells me to help her with her groceries to her car. I do and then tells me if I wanted to go to her place. My horny ass says yes I ask her age like a dumb ass but she was cool tells me she 71. We make it inside has that old weird smell. Gives me a joint and a shot of Hennessy then next thing I know she pulls out her denture and proceeds to smoke some rock. I was like wtf but she already between my legs. I get a blow job for like an hour non stop and my first gumjob. After we also fuck for a long time. Amazing we still in contact my woman knows her but doesn't know we fuck.

>>937145423 (OP)
I banged older hookers when I was younger. All the women were older. I met up with a 35 year old, a 40 something year old, it wasn't anything special.

GF is 3 months older than me, does this count?

>>937145423 (OP)
Several, including a couple of relatives. I honestly think the only way it doesn't happen is if you actively try to avoid it. (For both men and women)
The last one was my former college professor. First time we fucked, I was still her student and she felt awful about it until my dick was inside her.
We eventually stopped and she won't fuck me again because she feels bad that her husband is too old to get a side piece (he's around 20 years older than her and she's 56 now). So, I'm literally just waiting for the dude to croak and I'll have a post menopause human flesh light for the rest of her life. I'll probably get something big in her will because I make her feel young nad wanted.

>>937145423 (OP)
Yeah, she was 16 and I was 12

I fucked this dirty old cigarette woman. Her son lived with her and was about 2 years younger than me. We smoked a bowl while she cleaned her room up and when it was time I pscked him a new one and told him it's all his and went and railed his mom. She lifted her legs up and did some shit that made me cum instantly, and I mean that literally. Never felt anything like it since. She gave me gonorrhea

>>937176749
Was it worth it? Shit, it better be good if it gives you gono

when I was turning 13 we went trick or treating in Australia, its a 50/50 on houses saying fuck off we're not Americans blahblah and my friends and I finally get to a loud house with music playing its like 6pm the sun hadn't set yet

Some drunk as fuck lady answers the door and cracks up laughing at our very 'too cool, too old for this' Halloween outfits we got from kmart and brings us inside to show her drunk friends

they were having - im not sure what they're called, like early 2000s MLM party? normally its perfumes or tupperware type things for sale, one girl buys $5000 of it then has to pawn it off on all her friends with a presentation etc, but it was all sex toys and sex related stuff, dildos, handcuffs, vibrators, whips, mostly dildos, instead of having 50 settings they just had 50 dildos that did different settings

its all kind of a blur there were 4 of us, 2 left at some point and me and my friend stuck around they were asking us sexual questions asking if we know what this is, asking if we've seen tits before asking if we know what a pussy is etc

it all got a bit overwhelming, the lady hosting the presentation basically pushed us out and apologised - no candy and we went back to trick or treating, trying to find our friends etc, it was dark by now so we were in there for over half an hour at that point, went trick or treating and walked back that way home and the music had stopped and the cars were gone at that house so we knocked on the door as a dare to each other and "lol do you have candy now you said next time"

the woman ended up taking us in, showing her tits, pussy, letting us hold a dildo and fuck her with it in doggy position and sucked both of our dicks, neither of us finished

I think it was pretty traumatic, my next relationship after that was with a type A/bossy girl 2 grades above us who took the same bus and the sexual dynamic there got super weird, like before school meeting at the bus stop to go fuck but she would set limits on it like

>>937145423 (OP)
Sadly yes. Not my proudest moments.

>>937177868
Set limits on like, "you can only thrust this amount of times" or "im only going to bob my head up and down 20 times if you dont cum we're leaving" and after her I didn't want to do anything with other girls for a few years until I was 17ish

The other friend who stuck around pretty immediately got kicked out of school got into drugs, moved to his dads house and ended up killing himself, he was already kinda from that type of family I don't think it was related but its not like he ever bragged about it either, it wasn't a super cool experience and I get a visceral reaction anytime older women get caught with younger men/boys and the obvious podcaster/whoever says "durrr I wish these women found me when I was 13"

>>937145423 (OP)
Define "older woman"
Is there a particular age difference that you have in mind?
"Older woman" is such a vague term.

>>937145423 (OP)
Got sucked off by a 34 year old when I was 22. The only woman to ever make me coom from pure blozza.

Not sure if this counts because I was 35 at the time and she was 38...
My 1st and only sexual experience, was with my step sister. I live with my mum and step father, my step sister was having problems with her abusive fiance so she moved in to our place. One night she was so drunk she just came in my room and flat out asked "have you ever fucked anyone before"... she knows that i am a social retard...she left my room
next thing i know she comes back in my room, doesnt say a word, just throws her mini vibrating dildo at me while i was in bed watchin tv...(it was wet so she clearly just used it to get off) i knew this was my only chance to lose my virginity in life so i flirted back with her...
1 thing led to another and i started fingering her milf pussy, smelt my fingers cause i was curious to know what pussy smelled like (just smelled like a bar of soap, not fishy or musty like i was forewarned)....
well after that i tried to fuck her, but anxiety hit me and i couldnt get my dick hard...
went back to fingering and licking, apologised for being such a pathetic loser by not being able to get it up... she got dressed again and we havent spoken about it to this day... she turns 41 next month.

>My friend went out of state for school two years ago, but his family treated me like their 4th son.
>A while back his mom invited me over for dinner, which wasn't unusual, so I agreed to come over.
>When I got there my friend's dad and brothers were nowhere to be seen.
>Friend's mom told me they went on some church trip for quizzing, so she was home alone.
>She was lonely and thought spending some time with me would be fun.
>She cooked a big meal, and even though she doesn't drink had a bottle of wine and another of Jack.
>Dinner was great, and she drank the bottle of wine herself, and had a few shots of Jack with me.
>She was pretty wasted, and couldn't even walk. She asked me to help her to her bedroom to lay down.
>In the bedroom she asked me to help her get her dress off, so I naturally did.
>Hot little MILF in her white bra and panties then passed out, face down half on and half off the bed.
>My dick got hard as a rock, and all 5.5 inches were standing at attention.
>I had been wanting to fuck her since her son and I started hanging out when we were 13. 5 years of longing.
>She didn't wake up when I pulled her panties down and off, so I didn't even get naked before fucking her from behind, pants on the floor around my Vans.

Pic related

>>937178338
>I busted my nut that first go in about 15 seconds.
>She was still out of it, so I got her bra off and got her on the bed.
>I got one picture of her after I got her on the bed, damn she is a fine MILF.
>At that point I realized I nutted in her without a condom, and started to get hard again.
>I figured at this point there was not point in finding a condom, and I was already hard again...
>So I fucked her missionary and played with her little nipples while I took long strokes.
>I lasted about 5 minutes that second time, pulled out and loosed a load on her belly and tits.
>My cock was done for the night, but I did get a pic of my handy work
>I got a wash cloth from the bathroom and soaked it the sink, then used it to clean her up some.
>I found her dildo in her nightstand and slid it in her and turned it on for her.
>I then tucked her into bed naked, and locked the door on my way out.

This was March of 2024, and she didn't get pregnant. She also never said anything about it, and I've been over to their house about 20 times since then.

I keep hoping she gets a wild hair and wants to have dinner alone again.

probably my sister-in-law when I was 7 and she was 17, I don't remember exactly

>>937145423 (OP)
I'd gotten hj's and bj's from girls my own age but was still a virgin at 16. Started working at a restaurant right after I turned 16. Turns out the 35 year old butter-face assistant manager liked teen boys and would often service them.
A week or two after I started we closed together and she asked if I wanted a ride home because it was raining. I accepted but instead of driving home, she parked her truck in a secluded spot behind the business next door and I ended up sucking her tits and fingering her and she gave me a bj.
A few days after that we closed again and she asked if I wanted a ride home so of course I said yes. When we got in her truck she asked if I wanted to go to her place so she drove to her apartment, we showered and then fucked. I wasn't an expert at it but wearing a condom kept me from cumming right away and she was able to get off as well.
Never hooked up with her again because she moved on to her next teen boy conquest.

>>937181315
Should have given her a cream pie

>>937145423 (OP)
Came close when I was 25. She was in her late 50s. My buddy and I had lawn/GA tickets for a concert and her and her old mom friends were next to us. She randomly said my buddy and I made a cute couple and I corrected her that we weren’t gay. Then she got super embarrassed and bought us drinks as an apology. We got friendly. We got them a round of drinks. This woman was kind of grinding on me. Like ass swaying on my thigh, but not fully grinding on me. I finally ended up grabbing her hips and putting her directly against my dick for a song or 2.

She turned and was pressed all up against me and started asking if I thought she had a tight body for a 50 whatever year old and she went on about yoga or Pilates or whatever the fuck. I put a hand under her shirt and started it creeping up to her little titty, the whole time just telling her she was so fit. Incredible body. Blah blah.

She used one hand to pull my jeans and underwear away from my body and put the other down my pants. She had an awkward grip on my cock, I had a hand slipped under her bra and was rubbing her stiff nipple with my thumb. She got on her tiptoes and licked my neck and ear lobe and whispered that she was married, as if it wasn’t obvious by the rock on the hand currently pulling my jeans away from my body.

She shoved her hand a little deeper down my pants and we got interrupted by one of her friends and she got pulled away. She came back and said they were leaving to go back to their hotel. I wasn’t sure if that was an invite, but they didn’t wait for me to get the message if it was.

>>937181583
Didn't really give me a choice in the matter and I wasn't going to not get laid just because she made me wear a condom.

Currently talking to this 50something lady. No kids and doesn’t look to want to settle down but down to go on dates. Had a huge feet kink. I’m 28 first time with someone much older.

Advice?

>>937145423 (OP)
Dani ash

>>937145423 (OP)
I had a very close encounter with my mother's vagina

Yes. I lost my virginty to a 50 year old Lithuanian prostitute.

fucked a 46 year old when i was 27. We roleplayed mom and son. best sex ever

>>937149347
story now!!!!!!!!!!!!!!

>Be me, 27y/o
>Work for a small family business
>Manager is rude af
>kinda turn me on
>she is 43, married with two children in high school
>Christmas party.exe
>Everybody get drunk af
>few staff members flirt with me
>I joke about I want to bang the manager just to get rid of them
>She touch me a little bit too much
>I grab her and take her apart
>omg we are kissing each other
>She use tongue very good
>I am super horny
>She can feel the tent in my pants
>Got interrupter by another staff
>nothing else happened
>Days later hear that she told to her husband and now they have problems.
Times flies, tough wouldn´t happen again

>another staff party
>Another girl start touching the manager boobs.
>"Don´t do that. It makes me jelous"
>"You can touch my boobs if you want"
>Holy fuck they are perfect
>start kissing again
>She moves like a 20 y/o
>She makes me hard
>Got interrumped again
>Holy fucks. Have to wait again
>She´s getting married soon
>I need to fuck her soon

>>937168165
Isnt it like bad for ex addicts to date