help sex is hard for me

ive tried to have sex 3 times but every time me and my boyfriend stop because we get frustrated. evey time he tries to put it in it will not fit and it hurts alot. he put it in once and i screamed to the top of my lungs. getting lube is hard because i dont know how to ask for it. also every time he wants me to go down on him i dont feel like im pleasing

him enough because he never cums and when he does i make him take it out my mouth because i dont know if its okay to let him cum in my mouth. am i wrong please help me!