TheWorldBuilder
Planetary Scientist
- Joined
- Sep 19, 2019
- Posts
- 6,794
In absolute terms: 56 when I was 49
In proportional terms: 48 when I was 24
In proportional terms: 48 when I was 24
The oldest person you’ve had sex with...
- Thread starter MidKnight1378
- Start date
policywank
Literotica Guru
- Joined
- Aug 21, 2007
- Posts
- 3,200
80 or I guess 81 now.
When I was younger my parents were friends with a very nice couple. From my late teens I had a bit of a crush on the husband even though he was nearly 30 years older than me. He was a tall good looking guy with what I recognize now as big dick energy.
I have dated a lot of older men throughout my life. It is not a matter of preference. I like younger men or men my age as well. But I have always been comfortable with older men and they seem to be drawn to me. As either a young woman playing the field or a younger hot wife the nice thing about older men is that they seem less likely to get clingy or want take things seriously. They are just happy to be invited to the party. Anyway the point is that I was comfortable with the idea of dating older men and didn't see anything really taboo about it.
Of course I never made a move on him in those days. That was just too close to home. Plus he was happily married to a sweet woman whom I liked and he did not seem like the type to cheat.
Fast forward to early last year when I was visiting some family out east. Out of the blue he contacted them while I was there and asked to stop by. It turns out that his wife had died a couple years earlier and he just happened to be travelling there at the same time as I was. And it turns out that he lives in Ottawa.
So, when I came back here I contacted him and asked him out for lunch. He was a bit surprised, but non-plussed, that my husband didn't come. I made up an excuse why he couldn't be there, but the truth is that I hadn't invited him. We enjoyed each other's company and had a few more lunch dates. On the fourth such get together I confided in him the nature of my hotwife lifestyle. I was very nervous about doing so, but I thought he would be discrete about it even if he judged me negatively. He was clearly surprised. However, he took it in stride and even asked me a few questions about how it all works. I couldn't tell if he was just being polite or was genuinely interested.
At the end of our lunch I decided to take a further leap and asked him to invite me back to his place. He took a long pause and I could tell that the wheels were turning in his head. This was a situation quite unfamiliar to him and he was a very traditional guy. However, there was also an obvious attraction and he was single and lonely. He said yes so he took me home and fucked me. Obviously stamina is diminished at that age, but he was still quite viral and the big dick energy turned out to be justified.
After that we went on occasional dates - lunch as well as museums, art galleries and performances at the NAC. On many occasion he asked me to tell my husband how grateful he was for sharing me. Although I had always imagined he could have been a ladies man if he hadn't married so early I don't think that he ever was. Knowing that every date with me would end with sex seemed to be a bit of a thrill for him.
A little while later he told me he had started seeing someone closer to his own age and couldn't date me anymore. I told him I understood completely. A couple months later he called me to say that things hadn't worked out with that lady and could we pick up where we left off. I said yes. It has been on and off like that a few times since. I am used to that with many of my lovers, which suits me fine.
Anyway this lovely man seems to be having something of a sexual renaissance. He has the interest of women his age and me as a side piece when that doesn't work out.
When I was younger my parents were friends with a very nice couple. From my late teens I had a bit of a crush on the husband even though he was nearly 30 years older than me. He was a tall good looking guy with what I recognize now as big dick energy.
I have dated a lot of older men throughout my life. It is not a matter of preference. I like younger men or men my age as well. But I have always been comfortable with older men and they seem to be drawn to me. As either a young woman playing the field or a younger hot wife the nice thing about older men is that they seem less likely to get clingy or want take things seriously. They are just happy to be invited to the party. Anyway the point is that I was comfortable with the idea of dating older men and didn't see anything really taboo about it.
Of course I never made a move on him in those days. That was just too close to home. Plus he was happily married to a sweet woman whom I liked and he did not seem like the type to cheat.
Fast forward to early last year when I was visiting some family out east. Out of the blue he contacted them while I was there and asked to stop by. It turns out that his wife had died a couple years earlier and he just happened to be travelling there at the same time as I was. And it turns out that he lives in Ottawa.
So, when I came back here I contacted him and asked him out for lunch. He was a bit surprised, but non-plussed, that my husband didn't come. I made up an excuse why he couldn't be there, but the truth is that I hadn't invited him. We enjoyed each other's company and had a few more lunch dates. On the fourth such get together I confided in him the nature of my hotwife lifestyle. I was very nervous about doing so, but I thought he would be discrete about it even if he judged me negatively. He was clearly surprised. However, he took it in stride and even asked me a few questions about how it all works. I couldn't tell if he was just being polite or was genuinely interested.
At the end of our lunch I decided to take a further leap and asked him to invite me back to his place. He took a long pause and I could tell that the wheels were turning in his head. This was a situation quite unfamiliar to him and he was a very traditional guy. However, there was also an obvious attraction and he was single and lonely. He said yes so he took me home and fucked me. Obviously stamina is diminished at that age, but he was still quite viral and the big dick energy turned out to be justified.
After that we went on occasional dates - lunch as well as museums, art galleries and performances at the NAC. On many occasion he asked me to tell my husband how grateful he was for sharing me. Although I had always imagined he could have been a ladies man if he hadn't married so early I don't think that he ever was. Knowing that every date with me would end with sex seemed to be a bit of a thrill for him.
A little while later he told me he had started seeing someone closer to his own age and couldn't date me anymore. I told him I understood completely. A couple months later he called me to say that things hadn't worked out with that lady and could we pick up where we left off. I said yes. It has been on and off like that a few times since. I am used to that with many of my lovers, which suits me fine.
Anyway this lovely man seems to be having something of a sexual renaissance. He has the interest of women his age and me as a side piece when that doesn't work out.
Last edited:
HotwifeBrooksideKC
Literotica Guru
- Joined
- Dec 27, 2023
- Posts
- 890
I was 19 and he was 45
HotwifeBrooksideKC
Literotica Guru
- Joined
- Dec 27, 2023
- Posts
- 890
Lol
I have a question for the women on here who have had sex with much older men than themselves.
How did you meet and what was it that drew you to the said older man? I am not terribly old myself soon to be 34 but have eyes for a woman whose 22 years old. Maybe not as old as some of the other age differences on here but still one nonetheless.
How did you meet and what was it that drew you to the said older man? I am not terribly old myself soon to be 34 but have eyes for a woman whose 22 years old. Maybe not as old as some of the other age differences on here but still one nonetheless.
trucker6142
Really Experienced
- Joined
- Nov 30, 2007
- Posts
- 166
I was 25, she was late 40s. My 50. But damn 
Me too
BoredAsianWifey
Bored house wife
- Joined
- Dec 13, 2020
- Posts
- 630
I was in college 18-21 and they were in there 40s-50s.
Now I am seeing a 20s and he told me I am the oldest he been with. Not sure how I feel about that.
Now I am seeing a 20s and he told me I am the oldest he been with. Not sure how I feel about that.
ShaneoD
Literotica Guru
- Joined
- Nov 19, 2018
- Posts
- 10,973
Like you need to do things that he won't experience again in his lifetime and leave him wishing he could find someone like you in the future but he won't, maybe
BoredAsianWifey
Bored house wife
- Joined
- Dec 13, 2020
- Posts
- 630
Like you need to do things that he won't experience again in his lifetime and leave him wishing he could find someone like you in the future but he won't, maybe
More like I am happy I still can attract someone, but I am old now.
UnexpectedLuggage
Wannabe writer
- Joined
- Nov 8, 2024
- Posts
- 344
Late 30's, just the other day with my wife.
TorontoShane
Literotica Guru
- Joined
- Nov 20, 2007
- Posts
- 915
She was in her 70s and I was in my young 20s...
lick_ur_kitty
Virgin
- Joined
- Sep 15, 2024
- Posts
- 406
You are still SMOKIN HOTTT!!
ParkerSteve66
Sex is FUN
- Joined
- Dec 26, 2016
- Posts
- 1,305
Pussy is never too old for me.
Kissjoanie
Very Experienced
- Joined
- Jul 3, 2016
- Posts
- 467
Please tell us more sounds like the mature woman taught you a few things.
40sBiCuckCple
Experienced
- Joined
- Oct 2, 2024
- Posts
- 841
She was 67 and that was 2 years ago, he was 69 in May of this year. I have just turned 48. I had sex with her twice and it was wonderful. I might have had sex with men with a greater age gap when I was in college, but I really didn’t keep up with it. My wife has definitely had sex with wider age gaps than I have.
JustaguyinSouth
Virgin
- Joined
- Jul 27, 2025
- Posts
- 92
Islander55
Literotica Guru
- Joined
- Jun 22, 2020
- Posts
- 4,151
The biggest age gap was a year ago when I hooked up with a 25 year old guy and I was 65. He had just gone through a bad break up and needed some attention. Sexual and otherwise. I had sex with a 45 year old man when I was 23. Not my fault. He had a nice sailboat and his wife did not like to sail. Too good of a deal to pass up. Sex on a gently rocking boat can be really amazing.
OskarSpewbang
No title
- Joined
- Aug 19, 2025
- Posts
- 9
When I was 22 a 60 something neighbor. She was hot. Now it would be my wife. Late 60s.
WetMyKitty
Literotica Guru
- Joined
- Dec 4, 2020
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- 2,792
I was 35 and he was 60
SouthernMatureM
Back Again
- Joined
- Jan 10, 2025
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- 269
call_me_sarge
Really Experienced
- Joined
- Nov 7, 2016
- Posts
- 2,846
I was 18, just barely. She was 40 and married. We met where we worked, carried on an intense 3 year relationship, which included me seeing her daughter behind her back for awhile.
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