Multiple Partners Stories

A "WouldaShoulda" story is a moment from my real life where I made a decision that I later regretted or seriously wondered about. This is what might have happened if I hadn't replied with a friendly smile, said "Good Morning," and quickly continued on my way when that man showed me his very impressive penis in the street. What if...

My first wife confessed to being harried by a number of guys, although she was reluctant to go into too many details. What I do know was these incidents scared her early sex life and it took many years before she became comfortable with her own body, especial with her large 'D' cup tits.

Yacht Club
Our protagonist visits a summer vacation island and learns about its unusual traditions