Losing your virginity


I’m 19 and I’ve just got into a new relationship and we tried to have sex the other day and he couldn’t put it in as it was too painful. This happened with my ex boyfriend too, we tried about 4 or 5 times but every time we did he would get a bit in then when he tried to go in further it was just too sore and he had to stop. I’ve never had sex before but done everything else. Him using his fingers doesn’t hurt me and I’m always really turned on before he goes to do it can anyone please give me some advice