I've never deflowered a girl who I wasn't pretty deeply involved with--in fact I've (yes) turned down a couple of opportunities with girls who I was just in very casual relationships with. But I have been the first with a few young ladies. With all of them, we'd done a lot of other sexual things, including multiple fingers being used to get them off. So, in every case nobody had a small, tight, hymen, by the point in time we had sex. And in each case, there was tons of caressing and foreplay and an application of lube which preceeded the actual act. All of that said, the sensation from my end varied from feeling almost like it wasn't going to be able to get inside, to feeling like I was going through a tight rubber ring. It was always a very careful act, being as gentle and slow as was possible.
With one partner, it was too much, both in terms of pain and emotion, and we stopped with me only managing to insert myself about 4-5 inches inside of her--I withdrew and we just held each other through the night.
The orther two girls who I was the first with didn't have the same difficulty, but there was a very high emotional aspect of the act which I remember being very concerned about. With one girl, my first as well, I still remember that slow luxurious journey working my way inside of her wet yet tightly gripping pussy. It probably took a good ten minutes before she had fully tented and our pubic bones were mashing against each other. We both came that first time, although I wanted to keep going afterwards but she was a bit too tender down there to go for seconds. Kisses and hugs more than sufficed that night.
The other virgin who I had sex with, was my last virgin, and the sister of a good friend of mine who I dated one summer during college. She and I hit it off big time sexually, although she had just graduated high school (yes, still jailbait) and I was 3 years her senior. That was the biggest age difference I had experienced in a relationship up until then. She was really aggressive and pretty much pushed for me to get rid of her virginity. With her, although very tight at first, she really got into it, especially when I'd hit the end of her vagina, and she came and came and came. Her parents were out of town that weekend and we fucked several times that night. Her bedsheets were like a blotchy pink mess from the blood mixed with all of our fluids and we thought we might have to throw them out (bleach in the morning wash worked wonders though). With her it was pretty much a fun time between two lovers, although she did complain a bit the next day about feeling beaten up inside of her. After that summer together we went off to different schools and off to different new partners, but we've stayed friends over the years--once in a while still with benefits.
So that's my experience with virgins.
