Curious to see if anyone else has had this issue too haha

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Okay so he's not forcing me like everyone's assuming, and I know that he's clear of STDs as am I. He says that we can of course try to use a condom but in his past it hasn't worked and he's gone limp and it's embarrassing to him. We're both not seeing anyone else either. He's not a bad guy like I feel you all are assuming 😂 he says it's my choice and we'll try with a condom too if that's what I want. We've known each other for a little while and recently started seeing each other intimately for a few weeks. We're also not planning to have sex asap, we do want to wait a little. 

I know that the pill is 99% effective, I just wanted to know if there's a way to still use a condom where he won't go soft? If anyone has had experience!