Headphones won't fit, how to replace jack?

When I try and put in any headphones they get stuck around the second black ring, any amount of force doesn't work so I probably need to replace it, is this possible?

crwdns2934089:0crwdne2934089:0 crwdns2934093:0crwdne2934093:0

crwdns2934109:0crwdne2934109:0

crwdns2889612:0crwdne2889612:0 0
crwdns2934285:0crwdne2934285:0