I want to create a website with following specifications but couldn't figure out how to handle email sending part
- Users will select bunch of email addresses of companies to send an email
- Emails preferably should be sent using user's personal email address to keep emails away from spam folder
- User MUST NOT know who they are sending email to (email list is private)
- After mail sent to company X, company should be able to reply back to user's personal email address

It might sound complicated but it is basically a email sender web application to send some emails to private email addresses. I want to keep these email addresses private to prevent them to expose publicly.

Closest solution that I could find is, sending an email from my own domain but setting user's personal email as Reply-To field. However, I doubt that these emails might end up in spam folder of the receipent. Also, since that so many emails will be sent from this website, my domain might blacklisted after I while I'm afraid.