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Hell if I go for anything older it might be on life support.im 66 I guess 86 ? I can still deposit a hot load.
I've never really been with an older woman its always been younger and even then I'm taking 4or5years.
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tinytim40 Novice Jackinchatter

11 posts since 2021-03-14
78 year old
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I fucked a 50plus woman when I was in my 20's. Puussy is still good, just aged.
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When I was 18 me and my mate went back to this lad's house after a night out. He lived with a 40 y/o woman who hadn't been out but woke up and came to sit with us and chat when we got in. After hanging out for a few hours she said 'well I'm back to bed' and set off to walk out of the room. When she was at the doorway she looked back at me and moved her head in a gesture to say 'follow me'. So off I went having only slept with 3 girls before to having sex with this experienced 40 y/o. It was a completely different experience as she knew exactly what she was doing unlike the girls I'd slept with previously. We were up for hours having sex.

I remember waking up in the morning and seeing her naked lying facing away from me but I had to go. But before I did I slipped my cock inside her from behind one more time and fucked her until I nutted. Then I got dressed and sneaked out. Never saw her again.
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Andiskar Amateur Jackinchatter

269 posts since 2019-04-05
54 year old bisexual male from London
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Late 20s, bus ride home from work, spied this late 60s woman struggling up Conley Hatch lane, which is a very steep hill carrying an obviously stupidly heavy suitcase. Dressed like a total slut. Mini skirt, bright neon boob tube, very big tits and died platinum blonde hair, got off the next stop and walked down the hill. As I passed I casually asked, hey love that looks really heavy can I help you with that, she said oh yes please and I carried it up the hill for her to her flat in some dead end block. Up the lift. She asked if I wanted a drink. Sat on the sofa and my had my tongue down her throat and hands on her huge tits within two minutes. Spent a very enjoyable rest of the evening, eating her out getting sucked off and repeatedly emptying my balls in her cunt. 5 stars, would recommend,
If you like a post of mine please PM me. I always enjoy a chat.
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Wanker78 Enlightened Jackinchatter

3837 posts since 2015-07-08
heterosexual male
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I was wanked off by a woman in her mid-40s when I was 14. If still alive she would be in well into her nineties now confused

I shagged a work colleague- Helen- when I was 32 and she was 54 and she was one hell of a fuck. Thirty years later we still exchange Christmas cards though I havent seen Helen in maybe 20 years. winkrazz
Colossal Pervert- Think I'll treat myself to my third wank today
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My oldest was about 60 when I was about 35 good shape for her age great tits blonde hair nice face even if it was abit wrinkled and boy could she suck and fuck.
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Pocket-sized dynamo in her mid 50s when I was in my mid 20s. Great fun. Mad as a hatter, though.
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hornynstrokin Skilled Jackinchatter

635 posts since 2008-10-01
57 year old bisexual male from arizona, PHX area
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When I was 24 I had a very hot fling with a married 44 yo coworker. Beautiful petite woman who didn't know how sexy she was. Very shy and amazed I was hot for her but when the sex started she was amazing! She was always ready to put out for me and we fucked A LOT for 6 months before I moved away to college. Now I'm 54 and horny AF for my cute 64 yo therapist. She is in great shape, she wore knee high leather boots with jeans that showed off nice hips, ass, and thighs. I wanted her older pussy riding me on the couch as she took notes that day, wow.
I used to think friendly fire was a bad thing.
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FLscribe Professional Jackinchatter

1988 posts since 2014-06-09
55 year old bisexual male from tampa
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I was 38. She was 76, but I would have guessed 60. I made her cum three times just by eating her sweet pussy. She told me I was the second-best "oralist" she'd ever been with ... the best was her husband, who was watching from the corner of the room. He sauntered over and sucked my dick clean. He was pretty good, in fact.
Open to interesting ideas
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ohmy66 Amateur Jackinchatter

452 posts since 2021-11-22
82 year old male from North Wales
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A 48-year old offered it to me when I was 15 but I didn't fancy it. Later, I only had sex with females at least 4 years' younger than me; some 20.
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When I was 49 3 years ago I spent 3 months having a fling with a lady who was 74. We had sex 3 times a week for 12 weeks. She then moved to France and we parted company.
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Oldest to try it on with me was 65.
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staples2287 Skilled Jackinchatter

640 posts since 2011-04-25
49 year old heterosexual from US
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She was mid 30's I was 23. Fucked her really hard and she came, had her legs wrapped around my butt while I was humping into her missionary.
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UKPorn70 Novice Jackinchatter

98 posts since 2016-10-12
54 year old heterosexual male from East
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I was lucky enough to have a fairly long term relationship with an older lady, started when I was about 19 and she about 50. This lasted into her late 60s with her wanking me, sucking me, watching porn with me, and letting me touch her however I wanted, whenever I wanted. Never any fucking, line drawn at that. It was always really exciting. Now 50s myself, I am trying to get off with my very pleasant, friendly, naturist neighbour in her 70s who has the most fantastic big tits!
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UKPorn70 said:
I was lucky enough to have a fairly long term relationship with an older lady, started when I was about 19 and she about 50. This lasted into her late 60s with her wanking me, sucking me, watching porn with me, and letting me touch her however I wanted, whenever I wanted. Never any fucking, line drawn at that. It was always really exciting. Now 50s myself, I am trying to get off with my very pleasant, friendly, naturist neighbour in her 70s who has the most fantastic big tits!

Im guessing that one of the first things you will want to find is is how much creamy spunk those tits can take stroke
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