If so then teach him to masturbate you the same way and see if that helps, if you like your the satnav guiding him where to go and what to do :-)
Yes, I can bring myself to cum on my own.
I have tried doing this with him plenty of times but it never reaches the point it needs to, and I end up feeling like a chore:/
Maybe if I could get him to go down on me or SOMETHING! Lol
Do you go down on him if so say you would like to share the experienced and for him to go down and pleasure you :-)
I think that wild vs conservative thing may be a big part of the problem. Do you think you may be shutting down just before you come because you subconsciously do not want to upset his conservative ways?
I think you may need to work on bringing him over to your wild side but I din't know how you do that.
I have a similar problem with my wife. She seems quite conflicted about sex being ok or dirty. She is not at all adventurous, while I would love to have someone who would want to do wild and crazy things to me and me to her. If my lover wanted to use a dildo on me I would say go for it, let's try it. And several other things I can think of.
Alas the old missionary position seems to be it. After I do her orally to a writhing, moaning conclusion she manages to make me feel she feels we just did something dirty. So I quit oral about 20 years ago. I really miss that too. I was spoiled when I was 19 by a girl who smooshed my face into her puxxy every time we were together and held it there for hours. She taught me to love that.
Given my wife's attitude I just haven't bothered attempting to have sex with her many times when I would have liked to. I settle for masturbating as soon as I'm alone instead.
I've never succeeded in bringing her to the wild side in 47 years but I hope you may have better luck.