So, this is actually one of my favorite things to think about when I need to blow off some stream if you will. Really makes for good pillow talk too when the going gets good ;-)
Typically edge for a couple hours a day thinking about it and either blow it for her inside my wife’s pussy or on her tits/tummy or, if I can’t make it to showtime I’ll do it myself and send her some evidence of the explosion.
Not very often. I'm caged 24/7 so it's up to my wife when I'm allowed out. If I've behaved myself and kept up well with my chores and housework and she is in a generous mood I might be released for a minute to jerk off. Thats all it takes. Then right back into prison. Sometimes she likes to release me when her girlfriends are visiting so I have to make my sissy cream in front of them. They love the show and laugh and tease me about how tiny I am. I feel very humiliated and embarassed but my wife says it's good for me. She tells me I need to be reminded how pathetic I am and to learn to accept that I'll never be a man.