Lost my virginity over a month ago and since then have "done it" about ten times. I've had one or two times where it's not so painful but for the most part its extremely painful still. I make sure I am properly turned on and use hyposensetive lubricant (I have had awful reactions to most lubricants including durex and ky and all types of condoms - I am on the pill and he was tested for STIs beforehand).
This is further made harder because he has trouble coming inside me. We tried abstaining for two weeks and used vibrating rings (he sometimes goes soft after going for so long). We once went two hours and he still didn't manage but it just left me in tears from pain.
My sex drive is going through the floor and I'm starting to feel like anything physical is a chore. We're getting so stressed and frustrated. I just get upset and he is now terrified I am going to leave him (I'm not cos Iove him to pieces). we're both in our 20s and he's not very experienced either. I feel like I've waited so long and now it just doesn't feel worth it.
Sounds like you are both trying waaay too hard. If he knows that you are in pain and not enjoying sex, he will go soft. Sex should be about mutual pleasure and intimacy and knowing that you are hurting will kill his arousal too. It seems like you need to explore each other a little more before sex. Try things like mutual masterbation, oral sex, etc. Maybe change things up - have sex, if it starts to hurt stop and either arouse each other orally or manually. As the arousal grows and you want to try sex again, do it. Switch up positions. What rubs or feels uncomfortable in missionary might feel different with you on top or with him entering from behind. The two of you should just be trying a variety of things to try to keep it intimate and enjoyable. With time, things may loosen up, you will become more comfortable and familiar with what each other likes, and you will find what works.