F32 here. Not able cum during PiV, never. That's basically the main reason why I stopped short of penetration with my (p)AP, because I don't want him to feel insecure and drop me. I gave AP blowjob, but he was still rock hard after cumming in my mouth, still insisted for PiV (wanting to pleasure me in return). I asked him to finger me, but he was too horny to concentrate on handjob, and still made all the advances for PiV - I refused. TBH, I really want PiV sex with AP so much - I haven't ridden any other dick except my husband's for 9 years. I sometimes wonder if AP would allow me to use bullet vibrator while his dick is inside me - I know my body and I know will cum hard and loud like that. But trust me, taking out sex toy during first sexy time makes men even more insecure - it took couple years for my husband to get comfortable with it.

So my options are:
1. PIV, I don't cum, AP is insecure.
2. PIV, I don't cum, fake orgasm, AP is happy about himself. [this I did all my life with partners before met SO]
3. PIV, use clit vibrator, cum hard, AP is more insecure. [I do this option with my SO, and SO is insecure]