As often as I could

Oh I would cum in her after she cums all over my face!

I’ve cum in every lady I’ve had sex with for 50 years no matter what hole I’m in.

yes
 

mmmmmmmmmmmm

I always enjoy reading your posts.

I love cumming in my fiancee's pussy.

Maybe two years ago she asked me why I don't cum inside of her mouth during blow jobs. If I've been drinking, I can get one wad. After she has many orgasms, she wants to be fucked hard and rough. So I can't shoot a wad inside of her mouth and be sure I'll be able to fuck her. I told her that I'd rather cum inside of her pussy than inside of her mouth. She was momentarily incredulous. She thought I was kidding. After she got it that I was serious, she told me that most men wanted her to swallow. I told her that I wasn't like most of her former boyfriends and FWBs. Then I got to tease her about her stereotyping men.

My fiancee and I get along perfectly. We can tease each other about anything.

Why would she be any different?

Yes
 

Absolutely

Yes
 

Yes I'd cum in her but only when she's been pleasured and I'd only cum if she cums with me!