Experience with an older woman.

**muggly** · February 13th, 2019, 10:24 PM

When I was younger and left my first major job to work away as a goodbye thank you to the two women staff , my wife and I treated them to a meal with a lot of drinks thrown in. The youngest was 17 but the oldest was a bottle blonde 38 year old, who was very fit and a little bit like a cast member of the sci-fi series "Space 1999" with the same hairstyle as the moonbase women.
I was the designated driver and left the three women to try any mixture of wine and spirits they desired. By the time we were going home they were basically legless, and I was concerned if someone might throw up, but each was very merry , without nausea. As the youngest lived nearest to the pub I dropped her off first and not wanting my wife to get travel sick I dropped her off next then proceeded to take home Betty (?) on about an other 20 minutes drive. As I neared her district I knew a shortcut to her home and turned off the main roads. Suddenly Betty , who had been so quiet from the last stop I thought she had fallen asleep, exclaimed "ooh that's so naughty of you thinking we can stop". Before I could explain that I was heading to her house via a different route, she said it was ok provided her hubby didn't know anything about it.
I had known Betty for 5years and never thought about her sexually but suddenly I was looking at a gift horse so fancied seeing what she had in mind and pulled into a service area at the back of some shops. I was 25 and was getting quite aroused thinking about sex with a more mature woman. She got comfy and we kissed for a while and I was getting desperate to see her small tight boobs and what I expected to be a hairy black pubic bush, as her head hair was dyed blonde. Unfastening her blouse and letting her puppies free was very erotic and I gave them a good licking and nibble. As I was easing down her tights and panties she suddenly said she didn't want to get pregnant as her hubby had been sterilised, so no way could she say it was his. I hadn't come prepared so just enjoyed her short haired pussy with lots of folds of pink skin, using two fingers and tongue. She was squirming around having by the sounds of it several orgasms, but I wanted some cock action . As I put her hand against my trousers she eventually said she never touched dicks as she was scared she might get something nasty. So my orgasm had to wait. I still keep a good photographic memory of Betty's 34A boobs and pretty pink pussy but regretted that I wasted a strong erection on a promise. As it happened my wife was waiting for me to get back for some all night shagging so maybe Betty did me a favour.
Anyone had one night stands with and older woman?

stiv837 · February 14th, 2019, 08:59 PM

Never a one night stand , but I dated a few older married ladies when I was younger.

**muggly** · February 14th, 2019, 10:20 PM

Quote:

Originally Posted by stiv837

Never a one night stand , but I dated a few older married ladies when I was younger.

Good for you. I wished I could have had the nerve to date my mum's friend who was about 10 years younger than my mum. She used to tease me so much my dick was always hard. All my mum's nieces were a lot older than I was and were incredibly flirtacious as well as sex mad. One of my Welsh cousins used to flash her stocking tops in my presence and whenever she sat on a man's knee she would straighten her dress out with a quick flick to flash her undies too. Got her into trouble with several fellas.

stiv837 · February 14th, 2019, 11:28 PM

I always enjoyed when my mom's friends would come to visit. I really enjoyed jerking off in my bedroom knowing they were only a few feet away.

**Adam West** · February 15th, 2019, 03:18 AM

Gone out with a few in my time. The oldest being 15 years older than me. Really it was only a couple of dates and a necking session, but she felt guilty and went back to her older boyfriend (by a couple of years).

I'm 57 now, so that would make her 72 and her bf/hubby (if he's still alive) around 74 or 75.

The others have only been older by a year or two or five years.

**KissArmy** · February 15th, 2019, 12:17 PM

When I was in my early 20s my buddy knew two older girls who worked in one of our town bars. He set us up on a double date with them. These girls were mid, maybe upper 20s, but to me, they were "Older Women."

Frankly, I was scared of what my date was going to do to me. I had a preconceived notion that a barmaid was a jaded, rough girl who was going to expect me to put out for her. I wasn't ready for a one-nighter and I was damn sure I couldn't satisfy such a woman. I was pleasantly surprised... she was a nice person and it was a fun date. We had a proper kiss at the end and that was that. The only hint of her "rough" past was her passing comment that her father was a mean drunk. Never saw her again, but she broke my preconceived notion of barmaids and older women.

**muggly** · February 15th, 2019, 10:41 PM

Quote:

Originally Posted by KissArmy

Frankly, I was scared of what my date was going to do to me. I had a preconceived notion that a barmaid was a jaded, rough girl who was going to expect me to put out for her. I wasn't ready for a one-nighter and I was damn sure I couldn't satisfy such a woman. I was pleasantly surprised... she broke my preconceived notion of barmaids and older women.

When I was 17 as a holiday job I used to work as a glass collector in a working men's club and the stewardess got the idea I was 18 so I was promoted to barman. I had to work with a real floozy called Linda who was 20 years older than me but that didn't stop her flirting and making all sorts of lewd suggestions, but she was damn sexy with it. I also worked with the daughter of the stewardess and she was 19 and decided I was old enough for a fumble behind the club building one Friday night. She was sucking my tongue out of my mouth and her fingers were inside my trousers dragging my cock out of my Y-fronts . I was so excited with what she was going to do I nearly blew my load before she got my cock out, then a voice came from the kitchen door telling her to leave my cock alone as there are still glasses needing washing. It was her mother. I also worked with a Geordie 36 year old who had the best pair of legs I have ever seen, under a short check skirt and every time she bent down to get a mixer from the bottom shelf I was treated to a peek of panty heaven. We got friendly and once had a water fight which soaked her top, revealing two brown nipples and a pair of huge tits under her top. I think I got a bit carried away with her saucy comments and teasing and ended up squeezing her arse a few times plus as we were squashed into the glass cleaning area it was easy to feel her tits and stroke just below her tummy. In fact she absolutely loved me pretending i was going to grab her tits and it made her quite aroused as her nipples stuck out like hat pegs. So one boozy night after a mad evening i got hger into the corner and she asked (all innocent) what i wanted to do with her. I said i wanted to get her tits out for a suck and slip my fingers down her knickers for a finger fuck. She giggled and moved away but 5 minutes later came back and it looked like she was up for it. Most of the other staff were getting drunk in the other bar and i had her pinned up a corner. My hands were moving up her sides and as i pulled on her blouse a couple of buttons popped and the top of her tits came into view. She slipped her hand down over my trouser fly and squeezed my erection checking me out so I went for the inner thigh and slipped under her skirt to feel hot damp tights. Then a familiar voice came from the bar area asking where she was. It was her hubby. As it happened a few weeks later I was dating her 16 year old daughter who became my wife. What a difference her attitude to me was once daughter was courting me. I went from young stud and pet toy boy to her 'son', and she denied we had been inappropriate anytime. I know I never would have fucked her but I was pretty close to feeling my future mother in law's fanny, between those incredible legs.

Desnudez · February 19th, 2019, 03:02 PM

I had a dalliance with a woman in her fifties ten years ago, when I was in my thirties. She was busty and cute. We knew each other, but after we became friends on Facebook, we worked our way into conversations about sex and we ended up getting together one night.

Swinger would probably be the wrong term, but she definitely had a very open view of sex. Our first time together, she insisted on taking a bath together, which was kinda tough given the size of her tub. This should have given me a clue about her.

She was older, but curvy with surprisingly firm breasts. She had a wonderful hairy pussy that was light brown, almost blond. After the bath, I went down on her for ten minutes or so, and she came...squirted all over me. I was kind of surprised, but it just made me want to keep going. After a while, I started fucking her and she squirted again and screamed. I kept going. She must have squirted three more times.

She had a good time. We fucked like that two more nights. Then, we started having troubles. One night she insisted on watching porn first. I'm not anti-porn, I'm here right? I just couldn't figure out why she would want to waste time on it given we knew how to turn each other on without it. I took her to a nudist club and she didn't understand why it wasn't a place we could fuck in public. Then, she started saying insulting things about my religion. She didn't know she was being insulting, she just said the first thing that came to mind. I started getting weird text messages from her that made all sorts of assumptions about my past. It was obvious I had to just stop. None of these were deal killers, but I started getting the impression she was a bit crazy.

I still see her around once in a while. I say hi and leave it at that.

Doverben · February 19th, 2019, 03:38 PM

I was 33, she was 45 and had had 4 children.
She was a Slim, athletic, husky voice brunette.
Gorgeous and filthy but completely incompatible. Still had a lovely summer with her in 2009: (filth alert!) the only lady who has ever sucked my cock after it's been in her dirty bottom and spray my load in her face. Quite naughty.....

**Sir Honkers** · February 19th, 2019, 09:04 PM

Quote:

Originally Posted by Doverben

I was 33, she was 45 and had had 4 children.
She was a Slim, athletic, husky voice brunette.
Gorgeous and filthy but completely incompatible. Still had a lovely summer with her in 2009: (filth alert!) the only lady who has ever sucked my cock after it's been in her dirty bottom and spray my load in her face. Quite naughty.....

Sorry...but I have to ask. She didn't kiss you with that mouth did she?
My first serious girlfriend and the one I lost my virginity to was nineteen and I was seventeen. I thought she was incredibly knowing and sophisticated. That was also my first heartbreak when her family left to go back to America. If they hadn't, I think it's a real possibility that we might have eventually gotten married.

February 13th, 2019, 10:24 PM	#1
muggly Vintage Member Join Date: Jan 2012 Location: England Posts: 707 Thanks: 2,443 Thanked 6,631 Times in 683 Posts	Experience with an older woman. When I was younger and left my first major job to work away as a goodbye thank you to the two women staff , my wife and I treated them to a meal with a lot of drinks thrown in. The youngest was 17 but the oldest was a bottle blonde 38 year old, who was very fit and a little bit like a cast member of the sci-fi series "Space 1999" with the same hairstyle as the moonbase women. I was the designated driver and left the three women to try any mixture of wine and spirits they desired. By the time we were going home they were basically legless, and I was concerned if someone might throw up, but each was very merry , without nausea. As the youngest lived nearest to the pub I dropped her off first and not wanting my wife to get travel sick I dropped her off next then proceeded to take home Betty (?) on about an other 20 minutes drive. As I neared her district I knew a shortcut to her home and turned off the main roads. Suddenly Betty , who had been so quiet from the last stop I thought she had fallen asleep, exclaimed "ooh that's so naughty of you thinking we can stop". Before I could explain that I was heading to her house via a different route, she said it was ok provided her hubby didn't know anything about it. I had known Betty for 5years and never thought about her sexually but suddenly I was looking at a gift horse so fancied seeing what she had in mind and pulled into a service area at the back of some shops. I was 25 and was getting quite aroused thinking about sex with a more mature woman. She got comfy and we kissed for a while and I was getting desperate to see her small tight boobs and what I expected to be a hairy black pubic bush, as her head hair was dyed blonde. Unfastening her blouse and letting her puppies free was very erotic and I gave them a good licking and nibble. As I was easing down her tights and panties she suddenly said she didn't want to get pregnant as her hubby had been sterilised, so no way could she say it was his. I hadn't come prepared so just enjoyed her short haired pussy with lots of folds of pink skin, using two fingers and tongue. She was squirming around having by the sounds of it several orgasms, but I wanted some cock action . As I put her hand against my trousers she eventually said she never touched dicks as she was scared she might get something nasty. So my orgasm had to wait. I still keep a good photographic memory of Betty's 34A boobs and pretty pink pussy but regretted that I wasted a strong erection on a promise. As it happened my wife was waiting for me to get back for some all night shagging so maybe Betty did me a favour. Anyone had one night stands with and older woman?

February 19th, 2019, 03:02 PM	#8
Desnudez Member Join Date: Dec 2015 Location: Southern Arizona Posts: 53 Thanks: 772 Thanked 733 Times in 50 Posts	Odd One I had a dalliance with a woman in her fifties ten years ago, when I was in my thirties. She was busty and cute. We knew each other, but after we became friends on Facebook, we worked our way into conversations about sex and we ended up getting together one night. Swinger would probably be the wrong term, but she definitely had a very open view of sex. Our first time together, she insisted on taking a bath together, which was kinda tough given the size of her tub. This should have given me a clue about her. She was older, but curvy with surprisingly firm breasts. She had a wonderful hairy pussy that was light brown, almost blond. After the bath, I went down on her for ten minutes or so, and she came...squirted all over me. I was kind of surprised, but it just made me want to keep going. After a while, I started fucking her and she squirted again and screamed. I kept going. She must have squirted three more times. She had a good time. We fucked like that two more nights. Then, we started having troubles. One night she insisted on watching porn first. I'm not anti-porn, I'm here right? I just couldn't figure out why she would want to waste time on it given we knew how to turn each other on without it. I took her to a nudist club and she didn't understand why it wasn't a place we could fuck in public. Then, she started saying insulting things about my religion. She didn't know she was being insulting, she just said the first thing that came to mind. I started getting weird text messages from her that made all sorts of assumptions about my past. It was obvious I had to just stop. None of these were deal killers, but I started getting the impression she was a bit crazy. I still see her around once in a while. I say hi and leave it at that.

February 14th, 2019, 08:59 PM	#2
stiv837 Senior Member Join Date: Feb 2013 Location: North of hell Posts: 373 Thanks: 18,176 Thanked 5,105 Times in 386 Posts	Never a one night stand , but I dated a few older married ladies when I was younger.

February 14th, 2019, 11:28 PM	#4
stiv837 Senior Member Join Date: Feb 2013 Location: North of hell Posts: 373 Thanks: 18,176 Thanked 5,105 Times in 386 Posts	I always enjoyed when my mom's friends would come to visit. I really enjoyed jerking off in my bedroom knowing they were only a few feet away.

February 15th, 2019, 03:18 AM	#5
Adam West Vintage Member Join Date: Nov 2007 Location: Indianapolis - The Racing Capitol of the World Posts: 650 Thanks: 8,517 Thanked 6,205 Times in 635 Posts	Gone out with a few in my time. The oldest being 15 years older than me. Really it was only a couple of dates and a necking session, but she felt guilty and went back to her older boyfriend (by a couple of years). I'm 57 now, so that would make her 72 and her bf/hubby (if he's still alive) around 74 or 75. The others have only been older by a year or two or five years.

February 15th, 2019, 12:17 PM	#6
KissArmy Vintage Member Join Date: Dec 2010 Posts: 1,125 Thanks: 21,188 Thanked 12,380 Times in 1,106 Posts	When I was in my early 20s my buddy knew two older girls who worked in one of our town bars. He set us up on a double date with them. These girls were mid, maybe upper 20s, but to me, they were "Older Women." Frankly, I was scared of what my date was going to do to me. I had a preconceived notion that a barmaid was a jaded, rough girl who was going to expect me to put out for her. I wasn't ready for a one-nighter and I was damn sure I couldn't satisfy such a woman. I was pleasantly surprised... she was a nice person and it was a fun date. We had a proper kiss at the end and that was that. The only hint of her "rough" past was her passing comment that her father was a mean drunk. Never saw her again, but she broke my preconceived notion of barmaids and older women.

February 19th, 2019, 03:38 PM	#9
Doverben Senior Member Join Date: May 2014 Posts: 341 Thanks: 17,784 Thanked 7,408 Times in 332 Posts	I was 33, she was 45 and had had 4 children. She was a Slim, athletic, husky voice brunette. Gorgeous and filthy but completely incompatible. Still had a lovely summer with her in 2009: (filth alert!) the only lady who has ever sucked my cock after it's been in her dirty bottom and spray my load in her face. Quite naughty.....