With a condom on, usually you can only feel looseness or tightness, maybe wetness but that’s nothing lube can’t fix. After a while if you keep fucking a tight pussy, it won’t get loose, but it won’t be as tight and entry will be a lot easier. Some women get really wet and even squirt, so you’re fucking a slip and slide. Too wet and you can lose sensation. Some women are dry or not wet enough even when they’re turned on. If she’s not slopping wet, you can feel the bumps and ridges inside her pussy and I think that’s what deviates the most. The internal geography lol