I was 20 and his wife was 68. Followed them into woodland at local dogging spot. Incredible toned legs in a tiny mini dress. Was called over when I found them in the long grass to join them. When they told me they were retired I was gobsmacked. My next was the same age when I was in my early 30s. Married frustrated off a swinging site. Pulled up on her moped in a skirt, down the canal toe path, hand up her skirt before she was on her knees like she was starving, but she knew what she was doing. Ended up back at the car park bent over in car although she never played on a first meeting. Great Times with hungry older women

I was 25 and I fucked a woman who was 35. It was fun she knew what she was doing and I made her cum twice before I unloaded in her pussy.

lost my virginity to a friend of my mom's when i was 18. she was in her late 50s. she and her husband used to stay with us when they would visit. one time they were all going to see a movie and she said she was going to stay in because her back was bothering her. after everyone had gone, she asked me if i would rub it for her. after i started she said i wasn't getting to the muscle and she needed to take her shirt off. once those huge tits came out it was all over for me. we would fuck every time she would visit, well into her mid 60s. I miss those days.

I had lost my viginity a few months earlier and I was 28, she never told me her age but it was the same as Cher and that was 28 years ago, she was thicc, and we had talked about going to a nudist resort with her and a young friend of hers (whom I really wanted to see naked (never did :'( )

My bosses ex-wife.....she was 52, I was 18

One nighter with a mid 50s when I was about 20. Very assertive, quite vocal and surprisingly great tits (knew they were big but was pleasantly surprised gravity hadn't had its way with them).

Then a relationship for a few months with a mid 30s when I was about 24. Most adventurous partner I've had, even had a 3 way with her.

I was about 25 and slept with a friends mother in law who was 48. He was in hospital and I went to help her look after his kids. I ended up looking after her instead! She was so tight after years of being on her own. She was also an alcoholic so I saw her a few times after that, with a cheap bottle of Lambrini in hand!

When I was about 23 I had a fantastic sexual relationship with a co-worker who was in her mid 50s
She discovered early on that I had a thing for older women in stockings skirts and heels
We were alone in the office one day and she smiled and lifted her skirt up to show me her suspenders telling me she wore them especially for me
Lasted about 2/3 months and I will never forget her

I was 21 and she was 42.I met another woman at my friends company party. She was there. A week later the older woman and myself hooked up. She had just moved to town and was divorced. She has given me the best oral I have ever had. We hooked up a couple of times after that. She was a Great Lover! I took care of her sexual desires also.It was Great! Masturbate to how Great she was at oral sex.

I was 32 she was 68, bbw with big jugs 38F we fucked a couple of times but it was more mutual masturbation

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When I was age 15, I had sex with my aunt she was age 68, she was not my first but the best sex. We lasted a good 2 1/2 hours, she also squirted and had sex with her so many times after that first encounter.

In my late 20s i had a short term fling with a divorcee in her mid 60s. Never had any mileage as a long term relationship but had a lot of fun with her for a few months.

When I was in my early thirties, I worked with an older woman - late 50s. She would wear very 1950s style clothing, tight pencil skirts and blouses.
I found her really attractive and we started to flirt. She would let me feel her suspenders through her skirt and I was really turned on by the thought of her wearing stockings underneath. She would often rub her arse against me in the office and I would have to rush to the toilet to wank myself thinking about her.
Nothing happened between us until one evening we had a staff dinner and she had a few too many. She needed to fetch something from the office and insisted that I came with her.
Once we were in the office, she bent over the desk and wriggled her bum towards me. I needed no second chance and unzipped her skirt and slipped my hand into her panties, feeling her wet cunt. Unfortunately, she was not not wearing stockings that night, but the silk panties slipped easily to the floor.
I suddenly realised that she wanted more than my hand in her cunt and I unzipped my trousers and pushed my very hard cock inside her.
She grunted and squealed as i fucked her hard and begged me to fuck her hard, but not to cum inside her.
I reached the point of cumming and pulled out (like a gentleman) and she finished me off with her hand - I spunked in her mouth and she swallowed it all.
We sort of came to about where we were and , a bit sheepishly, tidied ourselves up before returning to the restaurant.
She was about thirty years older than me and it was one of the best fucks of my life - quick, but so exciting. Unfortunately, we never had the opportunity of a repeat performance and it was never mentioned again.
Wonderful - I am hard now, just remembering it.

Two different women in their 70s, both were a lot of fun and to my surprise no one had put in the work to help either of them cum more than once in a while. I made it a point to help them both cum hard 2x. Again wish that I could find another.