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How to stop comparing our sex life with his past relationship

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?
Have you two been exclusive for two years? Because I think if he was 35 when you started dating him and 37 before you were ready to have sex with him and he has stayed with you all that time then...... yea...... he really likes you! Not at all belittling your virginity but he's obviously isn't in the relationship for only sex.

I feel that if there was something left for him with his ex he was have gone back a long time ago. So..... you need to remind him how much you love being with him, remind him how special he is to you and let him know you still desire to be with him sexually but now understand that that might be a work in progress.

The worst thing you can do for your relationship is to start building up drama in your head that doesn't need to be there. HE WANTS TO BE WITH YOU which is why he is there with you. At 37 I'm sure he could find another woman who he could easily have sex with and he has made the decision not to do that but has chosen to be with you because you are the one he wants!!!

So focus on what is good about him and your relationship. Don't freak yourself out because that will definitely affect you physically. And as far as his keeping an erection he could be feeling he's not adequate for you or you're not finding him desirable etc. You've been together a long time at this point. You both should freely discuss what happened and work through it and know you can discuss matters such as these with each other. It would be bad if you were both thinking terrible things about yourself that the other person doesn't believe. Talk it out...... and he wants to be with you or he wouldn't be!

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