I've bottomed before twice but the person had a small dick and it felt good . I tried to use a toy on myself a lot bigger and it hurts everytime is it just a process or will it always hurt if its big ?
A baseball bat is always going to hurt. But I guess some people like that. Most people can enjoy toys within the normal anatomical size-range without pain. It can still hurt if you jam a toy in sideways or fail to relax. Maybe start with something a bit smaller to warm up.