Me and my current partner just got together intimately, for the first time, two nights ago.
She’s a virgin, the most she’s ever put in there was one finger (her hands are very small).
We did maybe an hour of foreplay before we got to actually having sex, along the foreplay I used just one finger (I was trying to be as gentle as possible, knowing she’s a virgin), but by the time we got to the penetration I couldn’t fit no matter what, so we just kept on grinding, and humping, and foreplay, then bumped it up to two fingers, fit in just fine and deep.
We brought lube and oils, gave each other massages, I tried fitting in three fingers, struggled a little but I could get maybe 3, 4 cm in with three fingers, no pain on her side either.
Then we tried at penetration again, still no luck, we tried doggy, prone bone, cowgirl, spooning, this one where she’s on her side and i’m upright as if missionary, and missionary (but struggled there cz of height differences).
More foreplay, until at some point she was fed up and wanted me to just “force it in there and we’ll worry later”, So we got into missionary and I kept my eyes on her to make sure she’s okay, we kept pushing and pushing till it started hurting for us both.
We settled for just foreplay till we both finished, and called it a day, I talked to her about that night after and she’s persistent that we try again until we make it work.
I don’t mean to sound pessimistic, but I’ve asked another subreddit about sexual incompatibility and all I’ve heard is that we probably just will not workout together due to differences we can’t control.
If you can help, it would mean a lot, the feeling of the thing that’s blocking us is this ring upon entry, everything inside is elastic except for this ring (felt with fingers).