This happened really back in "olden times" but it still seems so clear and so important to me! I went to a boys-only high school and had no sister, and so knew little about girls except for the stories other boys told. Mostly lies!
In the summer I was 17 I went to a music camp for two weeks and there I met girls, which I confess was more of an attraction than the music. As well as playing in orchestras and eating together there were dances and bus trips and I kissed my first girl, Sylvia. I was in love! She was perhaps a little plump, chewed her fingernails, and wore glasses but hey, nobody's perfect? She lived 100 miles away from my home but we wrote letters twice a week for a year. Then I left school and joined the army, which sent me to a place only ten miles away from Sylvia's home. Thank you, thank you!!
When we met again Sylvia seemed different. She let me kiss her but was very quiet and moody. After a couple more dates she confessed that in the year we had been apart she had let another boy, a man really, have sex with her. She said she had bled a lot and her parents had to take her to the hospital. She also said there was a big fight after which she hadn't seen the other guy again. After telling me this she seemed happier and let me put my hand on her breasts, in fact only on the outside of her sweater, but more important she invited me to visit her home the next weekend.
Her parents seemed friendly and made me feel welcome in their home. When they went out shopping I found Sylvia in her bedroom and we sat on the bed and started kissing. After a bit of a struggle, because that is what girls did back then, I got a hand under her sweater and into her bra. It was magic to feel her nipples harden; my friends said this meant a girl wanted sex. Could I go further? Wrestling a bit more, a few "no, don't" complaints and my hand went under her skirt and onto the crotch of her panties. Carefully I slipped a finger inside the leg and felt for her vagina. It was a surprise to find the small bush of pussy hair. The difficulty was that I knew nothing about how a woman gets excited; my information was that penetration was most important so I tried to push a finger up into her. "That's not what I want" she said, and I stopped in surprise. We lay together and she put a hand behind my neck and started to move a finger in small circles at the back of my head. I felt really stupid because I didn't understand! I stroked her head and neck and all the time my erection felt as if it would burst out of my pants. Then her parents came back!