Sex Advice/Oral Sex/Can't lose my virginity
I can't lose my virginity and it's not by personal choice. I have been with my boyfriend for two years, with almost the entirety of it being long distance as I moved away to go to school shortly after beginning to date. I am 24 and he is in his early 30's. He has had many sexual partners and I have had none. We are very open talking about sex and he has been tested and is clean. He has no problem become erect or ejaculating through either a hand job or oral but soon as he puts a condom on to have sex he becomes only partially hard. I have tried to get him hard again through stimulation but it just results in him ejaculating. I have also tried to keep stimulating him while he puts on a condom but soon as we go to haves sex he losses it. This happens both if I am on top or if he is.
This has never happened to him before (but it has happened with us three times). All of his past sexual relationships have been "meaningless" to him as they were one night stands or friends with benefits. I know it is making him more nervous for the next time and I know he works himself up because he wants to make it "perfect" for my first time. I reassure him that it's completely fine we never had sex and that "it will happen when it happens." I make it seem like it is not a big deal at all and I'm just happy to be with him and to be fooling around (which I am).
I know that there is an added pressure because as we are in a long distance relationship (ending the distance in 6 more months for good) so we never have a lot of time together. I also know he was (maybe still is) afraid that because I am a virgin he might be pressuring me-he is not, I want to and have told him numerous times I want to. He also blames the condom saying that condoms make it harder for him. I am not willing to not use a condom (even though he has been tested and I'm on birth control). What can I do to help him stay hard so I can finally have sex with the man I love.
It would help if he could abstain from masturbation for about a week before attempting intercourse with you. After a week, it is much easier for a male to do something different sexually. If he has an above-average sized penis, then a larger condom might be the way to go. A condom that is too small can be constricting for a man.