I am at a situation where I'm having sex with someone new, and I would very much like to use condoms with her. I'm used to unprotected sex with a regular partner (10 years, vasectomy) and have always preferred it as such. In this case, a condom is simply non-negotiable. I really want this to work.

The condom thing is not negotiable because neither of us has desire for sexual exclusivity. We are both tested and clean.

I have bought some that are advertised as a little larger and I tried one on myself while masturbating. That worked fine. But when it came to having sex with this girl, i don't know, maybe it was just a case of shy dick? I could simply not stay hard with the condom on despite being absolutely turned on AND having taken Cialis some hours prior. This was weird to me, since my erections have been absolutely rock hard lately even without any ED meds -- i have no actual issues here.

We ended up doing non-penetrative stuff and it was a blast. She was fully understanding about the whole situation and we could laugh about it without any hangups (sex in your 30s is just so unpretentious...) about the matter. She came twice, i came once, everybody was happy.

Thing is, I'd really love to fuck her proper and I know she would appreciate that as well.

Can anyone suggest me cures or practices for shy dick / condom dick and what I can do to overcome this?

Thanks <3