So... I'm 22 and I recently attempted (Key word here!!!) to have sex with my boyfriend of 2 years. He is 15 years older than me, so we have a considerably large age difference here. Despite that, I love him and I felt ready to give him my virginity. Well we tried multiple times and it just wasn't working. It was really painful for me and also, it was hard for him to keep his erection after putting on the condom and applying lube. It really made me doubt myself and wonder if he was truly as attracted to me as he claimed to me. We finally got it to the point where his penis was all the way inside my hole but it hurt so much that i could only take it for a short amount of time and he never came inside me. After that, I really have been reluctant about trying again and I keep comparing myself to his ex. He told me that for his first time with his ex, he had sex seven times in a row with her in one night. And that really bothered me because we can't even seem to have sex ONCE! I've just felt so depressed and un-sexy lately. Like i feel abnormal and terrible at sex and wondering if he was more attracted to his ex girlfriend than me and it just is driving me crazy. I pictured my first time to be so special, I never expected it to take multiple tries to get it right, or for it to be so painful, or worry about him losing his erection. It really hurts my feelings. My self esteem just feels rock bottom. I dont know how to deal with this or to stop comparing our sexual experiences with his past ones.
He is my first sexual partner, so everything is new and exciting to me. But for him, sex is old news. I just want him to feel the same way. How do I deal?