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How old was oldest woman you ever fucked and how old were you when you fucked her

Posted Feb 9, 2018 16:48 by anonymous
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  • Commented May 10, 2020 10:08 by anonymous

    My neighbor I help her doing her yard work she was paying me but after we have sex so many times I do it for free. She was in her late 70's I was only 15 at the time I don't remember how many times I had cum in her pussy and ass. Her blowjob was great, her mouth is so wet and she take out her dentures fucking her mouth like fucking a wet tight pussy. My parents said I am such a nice guy helping out the neighbor. I was fucking her the whole time until I join the military we kept it quiet the whole time.

  • Commented May 10, 2020 10:29 by anonymous

    I am 22 my oldest was 74. I have always had a thing for older women. I lost my virginity when I was 14 to a woman who lived near my grandmother she was in her early 60s. I would see her husband leave in the mornings and I would go for a visit. She was so much fun.

  • Commented May 10, 2020 11:00 by anonymous

    I have always been attracted to older women. The biggest age gap was when i was 20 she was 67 was shocked when she told me. At the time I thought she was 50 tops we had a sexual relationship for about 3 years. Until I was in my 30's my usual age gap was roughly 20 years.

  • Commented May 10, 2020 11:21 by anonymous

    When I was 16 I’ve learned everything there is about to learn concerning sex. The 60 something widow in my neighborhood had a lot of fun in her eager pupil to teach him. Always had a thing for old chubby women since.

  • Commented May 10, 2020 12:43 by anonymous

    I was 16 and she was 57 she kind of look like Farrah Fawcett. She didn't look old at all.

  • Commented Jun 24, 2020 19:03 by anonymous

    I was 21 and she was 68 my mother in law

  • Commented Jul 20, 2020 09:33 by anonymous

    I was 50 and she was 86. She was my widowed mother, and I found out how much she wanted a fuck when I came home early from work. She was lying on the sofa, and fucking herself with her fingers. I fucked her every night for just over 7 months, when, sadly, she passed away. She also gave a great blowjob, swallowing my spunk when I pumped it down her throat.

  • Commented Jul 20, 2020 09:50 by anonymous

    I am 26 living with a 70 year old

  • Commented Jul 20, 2020 12:10 by anonymous

    Every Friday evening I’m invited for a diner with my elderly neighbor. She’a a chubby widow of 69 years old, I’m 37 b.t.w.

    After diner we take a shower and fuck until the widow is exhausted, we go to sleep and the next morning, after the widow is recovered and made us a breakfast, we fuck again for an our or so. And damn, that widow know how to fuck!

  • Commented Jul 20, 2020 12:19 by anonymous

    16 she was 71, friends grandma.

  • Commented Jul 20, 2020 12:33 by anonymous

    74. Grandmother's neighbor. I was 19

  • Commented Jul 20, 2020 12:34 by anonymous

    I was 13 when dads aunt came to stay with us for the summer, she was 52 a little pudgy with big floppy tits and never wore a bra. We went to the river swimming when her white tee shirt was wet I couldn't stop staring so she said feel them if your so interested. I went for it so she took her shirt off then her cutoffs and panties and said have fun. We fucked like rabbits three times that day and two or three times a day for the rest of the summer. She let me fuck her a few times where my little sister could see so when she let it would be easier to seduce her. The last time we fucked she was 61 she said I was getting to old for her at 22 she wanted a younger nephew she broke in at least half of my cousins.

  • Commented Jul 20, 2020 14:49 by anonymous

    In my early twenties, I'd hang out in bars that had older women in them. I found a 22 year old could bed a woman from 40 to 60 and the fucking was great. I figure they thought it would be the last dick they ever got.

  • Commented Jul 20, 2020 19:37 by Uta

    “My great-granny had dementia. I started fucking her regularly when she was 81 and I was 14, with my widowed mother's permission. Her grey-haired pussy was so tight as she'd had nothing up it fore more than 11 years. The last time I fucked her, she was 97. That was 3 days before shed died. Mum and I were also fucking each other.”

    My friend, when I was young (11 - 16) did something similar. She had a grandpa who was 83 and demented. Sometimes he was awake and clear and at other times, he though about any woman around him, is his (dead for over 10 years) wife. I think, my friend must have been 13 or 14, when she told me, that she had jerked her grandpas cock. later she told me, she has sucked him off.

  • Commented Aug 5, 2020 21:11 by anonymous

    Has it been you, Uta?

  • Commented Aug 6, 2020 07:23 by anonymous

    My landlady of 68 for five years during study when I was 17.

  • Commented Aug 6, 2020 08:22 by anonymous

    Neighbor and my MiL are both in their sixties. Neighbor is a black woman with a slight foreign accent. Pretty, petite with small tits, nice long legs. Struck up a relationship after doing some work in her garden. Lady can deep throat to my balls, doesn’t even need to swallow.

    My MIL is the conservative type, goes to church etc. Big ole tits and in decent shape for her age. She just lets me fuck her, she’s a little too uptight to be sucking dick etc. I’m good with it though, her pussy is good enough.

  • Commented Aug 6, 2020 08:34 by anonymous

    In our late teens my best buddy was raised by his dad and stepmom, but his birth mom would visit a couple of times a year and she wasn't welcome at his house. She stayed at a hotel and had us over when she visited. His birth mom was crazy, 48 and chubby, smoked weed with us like it was no big deal, and bought us beer. At the hotel and we hung out with her, drinking, smoking, and fucking. I still can't believe my friend fucked his mom with me.

  • Commented Aug 6, 2020 09:20 by anonymous

    I was 22 and was doing a job at the home of a widowed lady who was 67. She got me into bed and we ended up fucking her all afternoon. The dirtiest and most horny woman have ever fucked.

  • Commented Aug 6, 2020 09:29 by anonymous

    15 lost my virginity to my 66 yrs old widow neighbor instead of paying me money to do yard work she pay me with sex.

  • Commented Aug 6, 2020 13:31 by anonymous

    29 SWM I don't go for a woman just for her age. I like to fuck. No surprise there right. The bar we go to pretty much sets the age of the crowd. Some are older like 50's creepy dudes and divorced or unhappy women crowd. I hooked up with women there I guess in their 50s. Some were really fun not too depressing.

    Oldest woman I got with I meet through work. She owns a company that subcontracts for us. She is in her 60s and seriously hot - no word of a lie. Slim with shortish hair in the messy chic look dresses young in jeans and tanks and a nice body. Her husband died several years ago. We've known each other for years. We worked on a lot of jobs together and she id on site a lot. We hit it off like any guy and girl does. Kidding and flirting. I have to go to her office to pick up prints and stuff so I see her a lot. Our flirting got more serious and we had a vibe. The first time we hooked up was after a end of project dinner. She had a few drink, not drunk and probably could have driven herself home just fine. But I offered and she accepted. I was probably 26. I spent the night at her house.

    We hook up pretty often. She is totally cool with it. Sex is great straight up sex. She give head and lets me go down on her. I don't ever even think about her age.

  • Commented Aug 6, 2020 14:08 by anonymous

    Coach's wife. I was 15 she was late 40s. She was fun. A drunk, but a fun drunk.

  • Commented Aug 6, 2020 15:58 by anonymous

    I was 24 and she was 73. We had a 4 year relationship before she ad a stroke and eventually passed away. I truly miss her.

  • Commented Aug 7, 2020 23:56 by anonymous

    At 17 yr old she was 45yo married teacher
    At 19 a 55 married woman I met in a bar
    At 30 a 70yo widow
    Now at 50something I'm fucking a woman in her early 70s and has been looking at me like I was dinner for years and an 82-year-old married woman whose husband wanted to find her a regular bull. For 82 she fucks like a mink and is one of the most sexually responsive women I have ever been with. She's also totally addicted to anal now, much to her husband's delight!

  • Commented Aug 23, 2020 02:02 by anonymous

    My first job I was 17 working as mail clerk at a legal firm, I flirted repeatedly with one of the legal secretaries Mandy & she responded occasionally with sexual innuendos, it wasn’t until we went out for a work function we were both tipsy when we left together, telling her I to go home she invited me stay at her place in a spare bed, there was no spare bed, she took my virginity that night I found out later Mandy was 55 year old & married., more than triple my age but I’ll always remember my first.

  • Commented Aug 23, 2020 04:47 by anonymous

    I’m always nice to old women, I like the chubby ones the most. I’m friendly to them and they are to me, always give me their biggest smile.

    And I found out they like to have sex with a young man (I’m 30), it gives them the feeling they still count in.

    I know a few so when I’m horny sex is just a phone call away.

    The women I’m talking about are 60-70.

  • Commented Sep 18, 2020 12:05 by anonymous

    My current FWB is 81 i'm 58--she gets wet as hell sucking cock--so after some oral we fuck--alot

  • Commented Oct 13, 2020 14:29 by anonymous

    36 y o married neighbor when I was 17. every few days. She told me her husband was lousy in bed.

  • Commented Oct 13, 2020 14:42 by anonymous

    I was 14 she was a 63 year old neighbor. I was being molested and then having willing sex with older women since i was 9. I pursued this 63 year old woman she had large breasts and really nice legs and ass for an older woman. She let me do anything i wanted with her. She like my enthusiasm about exploring her body. I would cum at least 3 times everytime i would go see her.

  • Commented Oct 13, 2020 14:44 by anonymous

    I was 24 and she was 70.
    I met her when I was 19 and we had a wonderful loving relationship

  • Commented Oct 13, 2020 15:28 by anonymous

    I was 17, almost 18 my senior year in HS. She lived next door, divorced and somewhere in her early forties. I'd get out of school at 3 p.m. Mom got off work at 5:30 p.m. The woman next door went to work at 6 p.m. So, we had about an hour, to an hour and a half to play. We were having sex several times a week, and a couple of weekends when mom was out of town visiting her sister.

  • Commented Oct 13, 2020 18:25 by anonymous

    I fucked a toothless whore. She said she was 35 looked more like a hard 75 years. I am 24.

  • Commented Nov 3, 2020 15:08 by anonymous

    I was 17 and she was around mid thirties and married. I lied to her and told her I was 18. i looked older for my age. I was fucking her twice a week while her husband was at work. She eventually found out I was underage, and stopped fucking me.

  • Commented Nov 3, 2020 15:16 by anonymous

    I was 14 and she was 65. She was an amateur porn actress when she was younger and still kept a high libido. She always grabbed my butt and fondled me. I was a horny kid so I let her. I was supposed to be in her house to help move boxes out of her basement. Instead, she sat and took my pants down to inspect and suck my cock. She was good and made me cum in her mouth quickly. She kissed me and made me taste my sperm before she had me kneel and lick her old hairy pussy. I got hard again and she let me fuck her on her living room floor. Her husband came home and acted like everything was normal as I shot my cum in her old pussy. I kept fucking her until I graduated high school. Her husband had ED and just watched or he would suck me and lick her to prepare us. She got me into trying bi sex and I enjoyed it.

  • Commented Nov 3, 2020 15:24 by anonymous

    I took over my dad's lawn service business right after high school one of dad's long time client she is 88 offer me a glass of water it was a hot day. I went inside as she handed me the glass of water she said sunny I love to have you make my wish come true. I said what do you mean she said I haven't have sex for years can you help me out. You guessed I got me a blowjob more like gum job as some of you might say then I fuck her afterward. That was the beginning of my extra service to her, never regret it I make her wish come true and leave her with a happy ending.

  • Commented Nov 3, 2020 15:29 by anonymous

    “I took over my dad's lawn service business right after high school one of dad's long time client she is 88 offer me a glass of water it was a hot day. I went inside as she handed me the glass of water she said sunny I love to have you make my wish come true. I said what do you mean she said I haven't have sex for years can you help me out. You guessed I got me a blowjob more like gum job as some of you might say then I fuck her afterward. That was the beginning of my extra service to her, never regret it I make her wish come true and leave her with a happy ending.”

    Kind of the same with me took over my uncle lawn service business couple of his long time clients asked me about the extra service if I provide or not, came to find out the extra service was sex with the clients.

  • Commented Nov 4, 2020 10:22 by anonymous

    The oldest women i ever fucked was 75 years old. I was 15 she was my next door neighbor I was fucking her granddaughter when she caught us. I ended up fucking her and her granddaughter together that day What surprised about the older women was how tight her cunt was for her age.

  • Commented Nov 4, 2020 10:41 by anonymous

    She was 34 and I was 12. I was at her house pulling weeds for her and she invited me in for some lemonade. She said Tommy I really wait something else from you right now. What I said. You know about sex right and I shock my head yes. She said don’t tell anyone as she took off her dress, panties and bra. Your turn and I stood there shock looking at her pussy. Come on it your turn and I stripped for her . She reached out grabbed my hand and pulled in grabbing my cock and putting between her pussy lips. Then she said fuck me and I push it in and started fucking her like a rabbit and was done in about a minute. Ooo that was great she said then she paid me the pulling the weeds about twice what she paid last time and I didnt even finish. I know what she paid me for.

  • Commented Nov 14, 2020 12:02 by anonymous

    I was dating a girl back in the mid '70s. I was 19 at the time. I'm at her house one day and her parents were getting ready to go to a Halloween party. Her Mom (who was very tall and slender) She was dressed as the "Jolly Green Giant" and had on a green leotard and matching green pantyhose. Actually green tights. I said Mrs. Stewart! You have really nice legs!!"
    A couple of days later my GF told me her Mom was very flattered by that. A couple of weeks later I stopped over to call on my GF but she wasn't home. Her Mom said she wasn't sure where she was or when she'd be home. I was disappointed but she offered me a drink and we chatted for a few minutes. She asked me if I meant waht I said about her having nice legs. I said yeah! They're wonderful. Long, slender and they lead right up to a very nice ass!
    With that, she stood up. Walked right over to me and pulled my head into her crotch area. She had on a skirt and I immediately lifted it up te reveal her underwear clad pussy. I began kissing and licking that pussy through her panties and she was shaking all over. But just then we heard a car pull in the driveway and it was my GF so we had to stop. Damn!! Unfortunately my girlfriend and I broke up a couple of weeks later. So I never had another chance with Mom. But I was never worried about age difference after that. And had many trysts with women that were easily 20-30 years my senior. Most of them were short term but very satisfying...

  • Commented Nov 14, 2020 13:09 by anonymous

    First "old" woman I fucked was a 50yo on her birthday when I was 20. She introduced me to her friends and I fucked a few of them, oldest was 54. For my 25th bd, just for the hell of it I went out looking for an old woman to fuck. Ended up fucking a woman I met online, she had claimed to be 70, but after I fucked her she admitted she was actually 78. Since then I've fucked several other women in their 70's and one woman 82. Also had my dick sucked by 85yo man.

  • Commented Nov 14, 2020 13:16 by anonymous

    My moms friend she was 38 and I was 20..she had a disabled husband after a accident...we came to a arrangement I'd service her when she want to.best sex ever

  • Commented Nov 14, 2020 19:25 by anonymous

    Flirted with my bosses wife she was 57, I was 17.

  • Commented Nov 16, 2020 10:07 by anonymous

    I was 21 and she was 67. I just came back from Iraq in 2004. "Helen" was my mom's friend and she was a slender dirty blonde woman. Helen and mom drank together on the weekends. While I was home on leave, Helen was buzzed and she told me how horny she was and felt me up. I let her and I got her to show me her tits. For a 67-year-old woman, Helen had nice semi sagging tits. I sucked on them as she pulled my cock out and stroked me. I was always horny and didn't care about Helen's age. I stood up and had her suck my cock. I got Helen naked and I ate her hairy yet trimmed pussy and asshole. While my mom was passed out, I fucked my mom's friend three times that night. In the morning my mom woke and found Helen riding my cock. Mom and I never spoke a word of what she saw but Helen told her everything in hopes of getting my mom turned on.

  • Commented Nov 16, 2020 10:12 by anonymous

    When I was 14 I had sex for the first time with a 73 year old woman. She technically "catfished" me because she used fake photographs of a girl my own age and we had an online relationship for almost a year before we met. I liked her personality and ended up having sex with her around 10 times before we ended it. She told me she couldn't do it anymore because she felt really guilt and was scared her family would find out. I am 20 now and still think about her almost every day....

  • Commented Nov 16, 2020 10:15 by anonymous

    I was 22 she was in her 40s and HOT

  • Commented Nov 16, 2020 11:29 by anonymous

    My 65-year-old mother-in-law, but it was a crappy fuck.

  • Commented Nov 16, 2020 16:04 by anonymous

    I was 11 when my senile grandmother decided to masturbate on my bed totally nude and she was really going to town. I got scared and ran out of the room she ran after me saying oh jerry it’s ok come back. My name is Jason she grabbed me and pulled me into my room and pulled off my clothes she was maybe 50 but had a head injury from a motorcycle accident a few years before and her acting out was because of it. She kissed me on the lips and gave me my first blow job. After I orgasmed, nothing came out yet I got up grabbed my clothes and ran to my room. I couldn’t stop thinking about what happened and played with my dick most of the night. It was a couple days later she was off again. I had been going into her room every day after to see if she would do it again but I knew she was acting different and as soon as I got home I hung out very close to her and even just started walking around in just a t shirt and my underwear. I actually got a little hardon and that’s when she saw. She was sitting at the table and pulled me close kissed my lips and then got right to sucking my little dick. I was shown how to lick her pussy and ass. She loved kissing and I loved how her tongue felt. We would be naked and fucking sucking and a lot of other really perverted shit. She would always finger my ass as she sucked my dick and always lick it while she licked my balls. We fucked until I was 17. I’d rush home and immediately run to her room and eat her pussy. I loved it. She passed away 2 years ago but I still jerk off thinking of the sick shit we did. I know she was probably fully aware most of the time when we did things and she was just a pervert and I loved every second of it.

  • Commented Feb 25, 2021 12:33 by anonymous

    when I was 13 my neighbour was 65 she lost her hubby and was very horny we fucked for many years she had no teeth and was great at sucking my cock

  • Commented Feb 26, 2021 09:04 by anonymous

    I was 16 when i fuck the 75 year old women that lived next door to me. I was surprised when she told me her age. I though she was about 50 years old because she does not look 75 years old.She has the body of a 45 to 50 year old women she still has firm set of tits and ass for her age. I been fucking her two to three times a week some days a couple times a day. She told when we first started fucking that she was lucky if her 80 year old husband got a had on that would stay hard long enough to fuck her.

  • Commented Feb 26, 2021 10:45 by anonymous

    “I was 13 when dads aunt came to stay with us for the summer, she was 52 a little pudgy with big floppy tits and never wore a bra. We went to the river swimming when her white tee shirt was wet I couldn't stop staring so she said feel them if your so interested. I went for it so she took her shirt off then her cutoffs and panties and said have fun. We fucked like rabbits three times that day and two or three times a day for the rest of the summer. She let me fuck her a few times where my little sister could see so when she let it would be easier to seduce her. The last time we fucked she was 61 she said I was getting to old for her at 22 she wanted a younger nephew she broke in at least half of my cousins.”

    Sounds like my dads aunt, her husband passed out by 7 every evening. She was the first Hippy I ever met and smoked MJ for the first time. Her tits have been without a bra since she got them in 1980 are still as pretty as ever. She loves to suck dick and fuck even if she's a little homely her body makes teenage girls jealous even a little chubby it shaped perfect.

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