
To be fair, my first time didn’t hurt at all. Maybe a slight pinching, but if you stretch or do a sport that engages those muscles your body can accommodate better. I did horseback riding for example. I also think some people are just tighter. I myself have always been looser, like tampons don’t phase me or what not. It may take stretching, lube, or just time. Also some guys just aren’t pleasant to fit down there.
I have vaginismus and that’s what penetration feels like to me, like being ripped open. The medical way is to start with dilators. The smallest is usually a about a finger size, the largest is a little longer and a little slimmer than the average penis (According to google stats), work up to what size you need to be comfortable and learn to control your muscles. Once the dilator you’re on fits and you can have it inside and move it without discomfort, move onto the next. Sex sucks when it hurts.
Oh and don’t listen to people that say do kegels. If you have vaginismus (which talk with your doctor but it’s relatively common and treatable) and your vagina is spastic (involuntary muscle tightning) then strengthening those muscles is the last thing you want to do, you need to train them to relax first and learn control, then you can make them as strong as you want later.