Gay or "guy guy" and how it feels?

ok im bi n im dating ym nice cute emo boy <3 and well if i ver see him at the house he lives in id prolly wana kinda cheer him up sine he got outof the hospital and hes a lil freaked out, so if i do id prolly wana hav with him im 14 hes 15 and i nvr had it but he did, how does it feel and will it hurt too much at first, hell use a condom and would tht hurt les or gv me ur expeirience and things to show soming going wrong plz ty