Your BF could practice at home in private how to operate the condom properly and get comfortable with it.
Also, the both of you can practice together how, when and who puts the condom on him without the intension of having sex, just to get used to the action itself and feel more comfortable with the whole thing. I have to admit putting on a condom is not the most romantic thing to do during a intimate moment. BUT, a safe one and safety always comes first!!!
Good luck!!!
Yes, it can be in his mind. It would be helpful if you could know if he had had any negative experiences with condoms or if there are any physical reasons for it, e.g. there are some reports of people having allergic reactions to condoms. It can be also helpful to try different kinds of condoms (extra-thin, ribbed, dotted...), be careful: some condoms designed for longer performance have desensitising effects and they can make erections weaker.
If it is mainly a psychological issue, it might help if condoms were introduced into foreplay activities, before penetration, in some kind of playful or exciting way during the activities which he prefers.
Good for you for wanting to be even more safe. Even though your on the pill you have a 1% chance of becoming pregnant. Condoms can help protect against pregnancy and STD's.
This sounds like it's a problem that's all in your boyfriends mind. Keep working on it and he'll get used to using condoms.
I hope your Dr told you that you have to go through at least one cycle of being on the pill before having sex without any other protection. Take care. Remar