Condom hurts? Advice?

Me and my boyfriend mess around and haven't gone all the way but we still like to put the tip in. He wore a condom to be safe the other day but the more we were messing around the more the rubber feeling of it actually started to sting or irritate my entrance. I had to tell him to stop all together in the grand scheme of things. Was it the condom's texture that hurt me or was I not excited enough? I'm confused. 😞