If you kiss someone or have oral sex without barriers you already risk spreading stds so I do not think the condom helps as much as people think. Also if you want to breed you almost might as well forget about the whole condom thing altogether.
so all that needs to be assured of is the freedom of your body from illness. I hope you don't take offense to that, but in today's society, you can never be too careful.
Nothing feels better than bareback. That said trust and knowing your partner is paramount. I have had a vasectomy so its never an issue from that point. Hey when you are super aroused nothing like eating your own cum out of her to bring her to even more orgasms.