Does penetration get easier with time? Advice appreciated /u/CarolinesThoughts Sex

I (27F) was a virgin until very recently. As I haven’t had penetrative (PIV) sex yet, you might say I still am (though I have done some anal penetration with dildos on this guy (29M) I’m seeing 😅). Although infrequently, I have been masturbating since I was a teenager but only ever did clitoral stimulation. As I’ve never sought a relationship, partly for fear of PIV sex, I never had any reason try vaginal penetration. I never really tried to put anything in because whenever I was horny enough to even entertain the thought, pushing my finger against the entrance still hurt so fucking much. But now I’m seeing this guy and we have such a great emotional connection that for the first time I can see the appeal of having someone inside me. I really want that to happen. He’s not my official boyfriend but we’ve agreed to exclusivity while we explore what’s between us. We definitely share a lot more than sex, we talk, we go out, we cook together, we cuddle, we generally support each other, but I also found out that he’s into femdom and we did a few scenes together that I thoroughly enjoyed. It’s simply amazing! He really likes having a woman ride him and it’s something I want for both him and me.

I didn’t have much spare time to practice but within maybe 6 or 7 practice session both alone and with him, I have finally been able to relax the muscles around my vagina enough to get in 1 finger, 2 the next time, 3 after that. Always with generous amounts of lube, patience and a vibrator on my clit to help me relax. I then got greedy and immediately wanted to try taking him but it just would not go in! I suppose that was just hubris on my part. Afterwards I decided to take more time to practice with toys. I purchased a vibrator (4cm in diameter) but even after thouroughly warming up my vagina with 3 fingers I could not get it in. The pain was unbearable. One of the problems is that I can “feel my way inside” with my own fingers whereas I don’t feel much when it comes to foreign objects except the excruciating pain at the extrance if it’s too big. Yesterday I finally managed to get the vibrator inside. It really hurt but it must’ve been less because otherwise it wouldn’t have happened at all.

I suppose this is all still within the range of normal (Correct me if I’m wrong). Can I expect more progress, slow as it may be? I guess it will always take time to warm me up for any sort of penetration but is there a chance that with more practice I will eventually be able to take this vibrator and his penis (he is not extremely wide, but probably a bit over 4cm) with ease?

Any and all insight and advice are greatly appreciated! (Btw English is not my first language)

TLDR: I’m a virgin when it comes to PIV sex. In preparation for PIV I am practicing with fingers and dildos/vibrators to stretch my vagina. In time, will I be able to painlessly take in bigger dildos and will it become just a little bit easier and with every time I penetrate myself?

I (27F) was a virgin until very recently. As I haven’t had penetrative (PIV) sex yet, you might say I still am (though I have done some anal penetration with dildos on this guy (29M) I’m seeing 😅). Although infrequently, I have been masturbating since I was a teenager but only ever did clitoral stimulation. As I’ve never sought a relationship, partly for fear of PIV sex, I never had any reason try vaginal penetration. I never really tried to put anything in because whenever I was horny enough to even entertain the thought, pushing my finger against the entrance still hurt so fucking much. But now I’m seeing this guy and we have such a great emotional connection that for the first time I can see the appeal of having someone inside me. I really want that to happen. He’s not my official boyfriend but we’ve agreed to exclusivity while we explore what’s between us. We definitely share a lot more than sex, we talk, we go out, we cook together, we cuddle, we generally support each other, but I also found out that he’s into femdom and we did a few scenes together that I thoroughly enjoyed. It’s simply amazing! He really likes having a woman ride him and it’s something I want for both him and me.

I didn’t have much spare time to practice but within maybe 6 or 7 practice session both alone and with him, I have finally been able to relax the muscles around my vagina enough to get in 1 finger, 2 the next time, 3 after that. Always with generous amounts of lube, patience and a vibrator on my clit to help me relax. I then got greedy and immediately wanted to try taking him but it just would not go in! I suppose that was just hubris on my part. Afterwards I decided to take more time to practice with toys. I purchased a vibrator (4cm in diameter) but even after thouroughly warming up my vagina with 3 fingers I could not get it in. The pain was unbearable. One of the problems is that I can “feel my way inside” with my own fingers whereas I don’t feel much when it comes to foreign objects except the excruciating pain at the extrance if it’s too big. Yesterday I finally managed to get the vibrator inside. It really hurt but it must’ve been less because otherwise it wouldn’t have happened at all.

I suppose this is all still within the range of normal (Correct me if I’m wrong). Can I expect more progress, slow as it may be? I guess it will always take time to warm me up for any sort of penetration but is there a chance that with more practice I will eventually be able to take this vibrator and his penis (he is not extremely wide, but probably a bit over 4cm) with ease?

Any and all insight and advice are greatly appreciated! (Btw English is not my first language)

TLDR: I’m a virgin when it comes to PIV sex. In preparation for PIV I am practicing with fingers and dildos/vibrators to stretch my vagina. In time, will I be able to painlessly take in bigger dildos and will it become just a little bit easier and with every time I penetrate myself?