I went through a period where I fantasized about cuckolding. This coincided with a strong interest in chastity. I have mentioned in another thread that I did a one week chastity experiment that did not turn out well. After that my interest in both chastity and cuckolding have diminished considerably.

When I was interested I concluded that cuckolding was best done with a lifestyle domina. Setting one up with a pro domme that you've only seen 2 or 3 times would lack the right emotional dynamics.