What's the biggest age gap sexual encounter you have had?

lol

holy fuck

21 and 16 which given the date started with me thinking she was 19 really made the gap feel larger

When I was in college I used to do stuff for this old guy in his 60s or 70s, can't remember how old he was but I used to get paid so much I didn't care.

I was 28 she was 47

>be me
>18 year old freshman in college
>working as barback at nightclub downtown
>some ~38ish year old lady is in town for convention
>she flirts with me for hours
>comes back at 4:30am as I’m wrapping my shift up
>comes home with me
>takes my virginity, also lets me in her asshole
>turns out she’s married
>3 kids, two my age
>sends a postcard to my bar later on
>addresses it to “Marshall”, the fake name I gave her
>coworkers open it and read it because there is no Marshall
>says I’m a sweet and generous lover
>gives me all her personal info
>never contacted her, probably a good idea
>works for Raytheon
>terrified to even try

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>works for Raytheon

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As a Freshman in college, I met a girl at some social event, ended the evening in bed.
The next day, she asked me how old I was. I told her the truth, "Seventeen."
She just about shit. She was a 23 year-old Grad student.
We continued our hot AF relationship until she graduated with her Master's degree two years later.
...years pass, I get my degree, get a job in the Tech industry...
One of the women in the Head Office takes a shine to me, we go out together, end up in bed.
We subsequently go to a music venue, where I tell her it's my birthday, so she offers to buy me a drink.
I show my ID to the bartender, who says "Twenty-one today? Your drink is on the house!"
She just about shit. She was 31yo
We continued our hot AF relationship until the company was taken over, and we were both laid off.

25 16, and 31 21

>be me, 30
>my wife had just left me, so I had a REAL hate on for women
>found an OLD lady online
>we talk for a few days, and she comes over to my apartment
>this was a total dom/sum relationship
>she did everything I told her to
>she was old, and grey
>milkers sagged nearly to her belly-button
>shaved bald pussy
>fucked 3-4 nights a week
>she was 52
>that's a 22 yr age gap
>found out later, that a few years previous, I had fucked her niece

I was 18 she was 43.

>First reply wins
Damn user.
Me, I was 19 she was 30. Summer of 1979. Taught me how to fuck that girl did.
Thanks Candis!

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19 and I was 29

19 and I'm 23

I got cucked hard by my age twice in one day
>Backpacking at 18
>Doing one of those guided tours with a bunch of other people
>Hit it off with this 25 year old qt, tight body blonde hair, cute voice, we spend most of the time chatting
>It becomes flirting real fast and by the end of the trip it's becoming clear she's coming back to my place if I ask her
>Fuck up and mention in passing I'm only 18
>She gets this look on her face like I just said I hadn't grown pubes yet, cancels her plans to join the group for drinks that night and I never see her again
>I'm pretty pissed but fuck it, I'll go out with the group and have a good time
>Night improves, I start flirting with this American Indian girl, she's into it
>We discuss celebrity crushes, I heavily imply I want to fuck her, she's up for it
>I'm not drinking because I've need to stay sober before my dive trip the next day
>One of the guys makes a joke that I'm not old enough to drink
>Girl gets the same look as the last one, asks how old I am
>18 is apparently a deal breaker because she's 26

I will never be as blueballed in my life as I was that night

26 when I was 43

Me 31
Her 59

i'm 58m and fuck 25 and younger females

She was a former school teacher. Took it in every hole. Had an anal orgasm

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How much do they charge per hour

HAHA
i don't have any wrinkles have natural black hair and not balding at all
most think i'm in my late 30's
most think

17 years old, with a 29 year old manager. I was a pasty white kid, thin as a rail and working at an understaffed supermarket and she was a 429 pound black woman with an ass wider than a car. When I told her I wanted to quit she offered her body in exchange for me continuing to work there. I took it and kept that job for about 12 years (she had a husband for 8 of them).

19 yo when I was 36.
Sex was great but we had zero to talk about when we hung out.

20 with 55yo, mom of the girl I had just dumped

15 and 78. Not my proudest but definitely my favorite.

No one thinks a 60 year old is 30

19yr old with 36yr female widow. she did it all
28yr with 50yr mom of friend good times

45y old with 18yr female. she had my dick in her mouth when her dad callled. he was younger than me

55yr found a 25yr female who liked daddy kinky roleplay

fuck yea

had a 18 ye old gf for a year when I was 34

19 while I was 33

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how did you find each other?

turning 60 soon. wife died have money want a young toy

I went up 3 years down 8 years.

my wife, who is 20 years younger than me.

I was 25 and she was 49. Was a little weird, but we had been flirting most of the night and it was fun

When I was 23 I fucked a 42 year old coworker. Divorce papers had already been filed but she was still someone's wife.

>needing to exaggerate
GTFO fgt pls

>divorce papers had already been filed
>still someone's wife
does any of that really matter to anyone, let alone a person like you?

fuckin nice. how'd it even start?

Me 30 she 19, and me 32 she 41

what did you even do to attract her attention like that? did her husband ever find out?

I was 13 my gram was 64

I was 11 she was 39.

There was no need to exaggerate but it emphasized the point. Find me one celebrity past 50 people think might still be in their 30s. That's some denial level shit right there.

Yes it made me harder

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Was over at a friends house while he wasn’t home to pick up a game, his grandma was in the living room with her walker, she was fucking massive then, and had an ass so big she would regularly get stuck in doorways and would need help. Was gonna go to his room but she stopped me because she needed “help”. She led me to her bathroom and coerced me into helping her get undressed, turned her ass to me and wobbled it back and forth like a massive plate of brown jell-o. She took my into the shower, had me wash her then we fucked on her bed after. Hitting it from the back was almost impossible, I was a small teen so the top of her asscheeks were slapping against my chin. Still fucking amazing though, fucked her 7 times after that and never told friend. He ended up being a dick so the jokes on him.

>Find me one celebrity

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I was the youngest guy in the whole store, white, and not a total deadbeat drug addict. I eyed her up constantly during work and never thought she noticed but I guess she did. I think her husband might have known about it but didn’t care.

I was 26 she was 62. Big saggy tits, a gut and a really fat granny ass. Her pussy was surprisingly wet. Surprisingly energetic too, she crouched on my dick and bounced on it pretty hard for a good 10 minutes. Came twice inside her, enjoyed it.

Others include
30 - 58. Slim granny basically.
20-29. A slightly autistic oddball with an incredibly solid round ass.

It's your argument/you're agreeing with the op. What a retard

Holy fuck nice. I’m and it was pretty similar to that. Especially the energetic part, don’t know how she kept it going but she was shouting and doing all the work. Took a couple minutes to get her going but when she did holy fuck the only word to describe it is “gushy”

>It's your argument
Lrn2argument, retard