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Started By
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The First time you made love to an older woman
Posted on 2/3/24 at 5:55 pm
Posted on 2/3/24 at 5:55 pm
(no message)
25
Posted on 2/3/24 at 5:56 pm to OWLFAN86
Mom fantasies for you again?
Posted on 2/3/24 at 6:00 pm to OWLFAN86
Think you meant to type this in your pornhub search
Posted on 2/3/24 at 6:00 pm to OWLFAN86
I feel like this is a classic bait and switch thread
Posted on 2/3/24 at 6:00 pm to OWLFAN86
My wife is older than me. So does that count?
Posted on 2/3/24 at 6:01 pm to OWLFAN86
quote:
The First time you made love to an older woman
Go on
Posted on 2/3/24 at 6:01 pm to OWLFAN86
Posted on 2/3/24 at 6:06 pm to OWLFAN86
I was 14.
What do you want to know?
What do you want to know?
Posted on 2/3/24 at 6:09 pm to OWLFAN86
did it again, then again in the AM
Posted on 2/3/24 at 6:10 pm to OWLFAN86
At my age its easier to find younger women.
Posted on 2/3/24 at 6:11 pm to OWLFAN86
When my wife and I started dating 
Posted on 2/3/24 at 6:11 pm to OWLFAN86
Nailed a woman bout 25 years older than me in college. I image she is dead now or at least on wheels like OP
Posted on 2/3/24 at 6:19 pm to OWLFAN86
Never have. Always went for the younger ones. Mine is 13 years younger & that's borderline too old.
Posted on 2/3/24 at 6:19 pm to OWLFAN86
Gross
Posted on 2/3/24 at 6:21 pm to OWLFAN86
Your grandmother.
Next question.
Next question.
Posted on 2/3/24 at 6:21 pm to OWLFAN86
Your mom made me a sandwich.
This post was edited on 2/4/24 at 6:32 am
Posted on 2/3/24 at 6:24 pm to OWLFAN86
There was nothing special about the first time I made love to an older woman. The 4th time though was special. I was living in Miami and Hurricane Irma was threatening. I was at the hospital doing my OB/GYN rotation in medical school and could not book tickets for evacuation. The girl who I had been on a few dates with was 10 months older than me. She was able to get us a flight out that night. When I got to the airport I found out that her dad was a billionaire and we were evacuating on his private plane. I joined the mile high club about 90 minutes into the flight.
ETA: Unfortunately she turned out to have borderline personality disorder. The old saying is true that money can't buy happiness and eventually pussy stops offsetting crazy.
ETA: Unfortunately she turned out to have borderline personality disorder. The old saying is true that money can't buy happiness and eventually pussy stops offsetting crazy.
This post was edited on 2/3/24 at 6:32 pm
Posted on 2/3/24 at 6:26 pm to OWLFAN86
Was 19, fricked 3 of my mom’s friends. 45,46 and 51. All of them knew what they were doing by far, one tried the whole neglige thing when I came get a “snake” from inside her closet. The other himmed me up against the front of somebodies jeep in front a bar room. But the 46 year old kept me around for quite some time. Once we called it off, we would hook back up if we were free. It was pretty cool.
Posted on 2/3/24 at 6:39 pm to OWLFAN86
Knocked the dust off several back in the day. Made 2 of them cry when they experienced their first orgasm. Couple of others lost control of their bladder from violent orgasms. After sex, one of them got up crying and ran to the bathroom to throw up. Discovered dirty talk really gets them hot. That’s about all I got.
Posted on 2/3/24 at 6:46 pm to OWLFAN86
...I caressed her dentures lovingly.
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