Scarleteen

Long time no see... this is embarrassing to talk about but I feel concerned/embarrassed and not sure who else to talk to right now

We never planned a specific time or anything, but there have been a few times my boyfriend and I have tried to have sex. He'd get the condom on and we'll have some fun let our places touch etc... but other than a tiny bit it just can't get in??? I'd be plenty aroused and wet every time so that's not the problem. He's tried both gently and also with a bit of a push. Am I too small?? is he too big??? is there a secret i don't know about?? is there any sort of virginity-losing tip???

I have a few thoughts here.
Have you (or your partner) ever tried inserting a finger or two, to get used to that sensation with something smaller than a penis? It might help to try that a bit before you try to have intercourse again. I think doing this with a glove & plenty of lube is the way to go so you experience less friction and less risk of a sharp fingernail poking you. The sensation of insertion can be hard to get used to, and going from zero to penis can be a pretty big adjustment, especially at first. In addition to arousal, relaxation is also key; it's easy to tense up a bit when things feel painful or

Also, you've mentioned before that you've been on testosterone for a couple years - many people on T notice that they produce less of their own lubricant, and/or that it's thinner or less slippery in texture, and find that their vaginal tissue feels a bit more delicate. It may be that it takes a little extra time and gentleness for you to relax and feel comfortable enough for intercourse to happen, and I think a good lubricant is extra important here!
Here's an article on intercourse that you might find helpful as well: From OW! to WOW! Demystifying Painful Intercourse