I’ve been with my boyfriend for 5 months, before we started dating he was definitley a player. He’s slept with around 30 women, and masturbates regularily. He’s never had this issue before with cumming. In the beginning it was hard to make him *** too, but we got there after 3 hours... I’ve tried so hard, foreplay, role play, new positions, sucking, stroking, everything I could thing of, and research. I asked him for tips and I’ve followed all of them, I’ve been more verbal, I’ve switched things up more, yet I haven’t been able to make him *** in a month. I’ve jacked him off for literally 3 hours once (because I guess he’s used to masturbating so it feels better for him) he still didn’t ***, that’s how dedicated I am. I’ve expressed my concerns that it’s just me, I’m very insecure. He has reassured me that he doesn’t know why he can’t *** but it’s definitley not me because I haven’t done anything wrong and that I’m great at sex. Then why when he masturbates he can come, but when I jack him off (listening to all his advice the whole time) he can’t? I feel so ugly and I feel like it’s completley me... what else could it be? We have also tried him stopping masturbating for a while and it still hasn’t worked. Sex has become a chore for me now, but I feel like I need to please him, yet I feel like I’m constantly left disappointed with myself, sad... I’m trying so hard whenever we have sex, and I also try to be more neutral and not try too! Just to switch it up! Nothing has worked, he smokes cigarettes and is on anti-depressants... which I know can prevent achieving climax, but he can make himself *** so it still doesn’t make sense. Whenever he makes me *** I feel like **** because I’m sad about it, please help me because I’m so upset...