How old was the oldest woman you have been with and how old would you go?

[the biz]

hi all thought i would add some of my experiences as well

i will do this in order as well

when i was 18 minus 1 year i brother snuck me into the local pub/club had a few drinks was all new to me didnt know any better so went and had a dance and started dancing with this lady
blonde hair curvy nice round arse big tits anyway i said hi we danced more then she offered to buy me a drink
so we sat down at a table had a couple of drinks started kissing it was getting late i put my hand up her skirt and rubbed her pussy a bit and she said stop
i thought i was in trouble or something lol but sge said lets get out of here and go to her house my jaw dropped and i followed her out of the pub and we walked a couple of blocks to her unit
as soon as we got inside she grabbed me and we started kissing she undid my jeans and my cock sprang out i was hard still from the pub
and she dropped to her knees and gave me my first deepthroat blowjob i almost came straight away she was very talented
anyway i stopped her and we went to her bedroom
were i went down on her she sucked me some more slid a condom on me and rode me till we both came i found out later on she was was 39 was a great night but never got toether with her again .

[the biz]

when i was 24 i was sleeping with my boss secretary she was 43 blonde and curvy we got along great at work anyway she was moving house to live with a friend and her son and asked me to give her a hand
we grabbed the work van and moved all her crap took all day got it all in and i went home had a shower was lying on my bed
relaxing when i got a txt msg from her that said thanks for the help today but i was want some more help
one thing about her was that she spoke what she thought witch was good for me
i said what do u need help with she replied my pussy i replied you dont have a cat lol she said you know what i mean
and to grab some beer and come back around
so i grabbed some beer and sent her a msg and said im on my way
i was driving along when i got another msg from her that said you better be comming over dont stand me up
because i need cock
so i drove a bit faster lol
i got there her friend was there we had some drinks then her friend had to go pick up her son so we were alone outside having a smoke and a beer she was wearing a just a nightie
we started to kiss and i went straight for her pussy rubbing it and fingering her she sucked me off for a bit then her
friend came home with her son and had to pull ourselves together
we all had a another drink not the son then we all decided it was bed time yay for me
but my friend hadnt put her bed togeher yet and asked her friend if we could have her sons bed
she said ok so we went to bed shut the door and i went down on her she sucked me another deep throater amazing all the down and then manged to get her tongue out and lick my balls was fantastic
we 69ed for a bit then i got between her legs and fucked her then she rode me then we switched to doogy style her favourite position she had a dirty mouth to saying all the things we love to hear
then i got got on top of her again and she was saying cum on me cum all over me well i didnt last much longer after hearing that and pulled out and blew all over her stomach and tits
she loved it and rubbed it all over herself she was amazing

anyway after that we would fuck at work yes on the boss desk my desk the floor the bathroom and plenty of blowjobs as well
and at her house as well we had alot of fun thats for sure
we didnt see each other for a while but we got together for a drink at her house a couple of years ago i was 32 and she 51 and that ended with me getting a blowjob and her getting a face for of cum he he

[the biz]

now my oldest and biggest age gap was with a lady who was 67 i met her on a dating/sex website
i was 26 at the time we started chatting hit it off she was a big lady brunette huge tits as well
she used to be a swinger back in the day
anyway we decided to meet at a hotel/motel she turned up with a bag full of dildos after we said hi and had a drink we started
kissing and fondling she was on the side of the bed
i stood up and undid my pants and she started sucking me off i grabbed her bag of dildos and said your turn i got her naked
and started licking and sucking her tits while i put the first dildo in her pussy
then i went down on her sucking her clit i used a few different vibrators and so forth on her until i got to the last one witch was huge
she had no problem taken it at all watching it go in and out of her was so hot i pulled it out
and started fingering her two fingers then three then four and finally i went with the full hand it popped in nicely
she was moaning and bucking i was fisting her it was great
i finally stopped and jumped on top of her and started fucking her she was a bit loose but it still felt great
we swapped positions a few times her on top doogy style a quick detour for more of a blowjob the me on top of her
for the big finish
i was going as fast and hard as i could we were both working up a sweat
i pulled out and shot my load all over her but it was more powerfull than usuall the first three or four spurts plastered her face got her staight in the eye
witch she was not expecting after i had finished we were a sweaty cum soaked mess we had a shower and went to bed having sex three more times that night and in the morning before parting ways great night thats for sure

now some advice to you all if you havnt havnt fucked an older woman you are defentely missing out always great fun to be with they know what they want when they want it and usually arent afraid to tell you that gotta love em

cheers

[relish10]

My oldest so far is my wife, who's 50, and she's the only one I've been with since we met at 20. But, when I was 15 my mom had a party, and one of her nurse friends who was 32 had been to an Andy Gibb concert and seemed interested in younger boys. I helped her get her bag from her car when it was clear she had drank too much, we made out a bit out there, then stripped each other on the living room floor -- even with some other "too drunk to drive" people passed out in the same room. She didn't want my mom to know, so she kept saying for me to come visit her at her place in the city, where she had two gay roommates who wouldn't care what we were doing. She said we could just stay in bed all day. Unfortunately, being 15 and living with my dad, I couldn't just disappear for a day without an excuse, and it never happened. Oh well, the visual memories are still vivid in my mind.

[maxdibble]

Ok it was the late 1980's I was 35 No cell phones no micro sized video Cameras. Mine was full sized tapes. I was asked to video tape a property for sale. And Duplicate the video and show the ranch house and the property and the Crop. I met the owner and his lady who worked as his Secretary and house keeper of sorts. He was in his late 70s and was an arrogant British ass, asked all the part of the lord of the manner. However his House keeper for 30 plus years was a real sweet lady. He asked if I knew anyone who could trim the trees rubbing against the roof. I told him I could do that and would come to do it said the next day. The house keeper was 87 that year and a boxed red head that had gray roots showing more than she liked and she was very friendly showing me where the tools and saws were. She always was elegant as she moved around the property. So I trimmed the trees and came down pretty dirty and sweaty. Her name was Jessie but she said her friends all called her Pinky. She said to go get ready for a shower in the bathroom off the hall near her room. She said to strip and she would wash my clothes while I showered and she just waited for me to take them off. She stood there looking at me as I undressed and then took my clothes and left me getting into the shower nude.

When I shut off the shower and got out there she was with warm towels from the dryer. She said turn around and she dried my back and then said turn around again she toweled my legs and then my shoulders and chest stomach and my cock and balls. She then sucked my penis into her mouth and said nothing as she sucked me until I came. She said relax on the couch wrapped in the towel until my clothes were out of the dryer. She made me a grilled ham and cheese and gave me a cold beer. Shit head was taking a nap mid afternoon so we were on her side of the Ranch house. I said thank you for everything and she says no she wanted to thank me. And so the next nine years years I did handy work around the ranch. I have more if you want just let me know.

[Mr and Mrs W]

Mr here.... I lost my virginity at age 17 to my then girlfriend's mom who was 38. It was a great way to learn from a MILF with experience. I never did have sex with the girlfriend, because she was too stuck up, but her mom certainly delivered.

[xxxxenophile]

Originally Posted by maxdibble

When I shut off the shower and got out there she was with warm towels from the dryer. She said turn around and she dried my back and then said turn around again she toweled my legs and then my shoulders and chest stomach and my cock and balls. She then sucked my penis into her mouth and said nothing as she sucked me until I came. She said relax on the couch wrapped in the towel until my clothes were out of the dryer. She made me a grilled ham and cheese and gave me a cold beer. Shit head was taking a nap mid afternoon so we were on her side of the Ranch house. I said thank you for everything and she says no she wanted to thank me. And so the next nine years years I did handy work around the ranch. I have more if you want just let me know.

For some reason I love this story - it's hysterical and awesome. Clearly older people still have desires, and I wonder how much further her service extended? I don't hear enough like this, but thanks for sharing this!

[xxxxenophile]

Originally Posted by maxdibble

I have more if you want just let me know.

Whoops, I forgot to say - please tell us more!

[Emanon13]

I'm 40 and currently seeing a 58 year old woman with a body to die for and she loves to fuck!

Perfect Package!

[Uncle_Bud]

During the 60's and 70's with my cousin 8+ yrs. older

During the late 80's, early 90's in my 30's, woman was 12 yrs. older