clitoris too painful to orgasm (kinda tmi)

So, I've never orgasmed. And I've never really wanted to because idk I feel awkward when the attention is all on me like that, but I talked to my SO about it and he was totally down. I can't orgasm from penetration so I laid there while he touched me for a good hour, switching from fingering me to rubbing my clit and he even was super cool about me giving suggestions and telling him when he was right on my clit. But when he started rubbing my clit it felt good, but it also hurt. Like I was so torn between pleasure and pain that I was squirming. And it wasn't like he wasn't being gentle because I've tried it myself before this and it's just so unbearable that I can't imagine doing it long enough to orgasm. This went on for over an hour, him touching me and turning me on and rubbing me and I literally felt like crap afterwards that I couldn't really say I was close. Like, it felt good but I couldn't bear it long enough it get close. And I feel like it really got to him that I couldn't orgasm but I feel like crap because honestly I feel like he did a good job and he was listening to suggestions and everything. Can someone help me :(