As the title says, I (M25) have not been able to cum with my current sexual partner any of the times we have had sex. I don’t mind, it’s not the be all and end all, but it would be nice. I suspect I have become conditioned by my masturbation habits to only be able to cum in a certain way (I’ve been single for a looong time). What can I do to change up my masturbation habits over the next month (I’m away travelling for a while) so that I can cum with her when I get home? I have a stroker, and I need to use a condom every time I am with her, so my gut reaction is to wear 2 condoms and masturbate with the stroker so that I get minimal sensation and start breaking down this preconditioning?
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Try doing hands-free maybe. Focus on thrusting, and trying to come from thrusting without your hands choking your dick,
maybe into something propped onto the bed. That way, when you thrust into her, it might feel familiar and you can let go.