I was a Junior in college. During Christmas break, a pretty Freshman I had my eyes on decided to send me a card or letter in the mail every day. While she claimed that she chose me at random and was just doing it for fun, it was pretty clear she was interested in me. It took about a week after we got back from break before we were officially dating.
Emily was cute and cutesy. There wasn't anything particularly remarkable about her looks. She had medium length sandy-brown hair, a slightly turned up nose and carried the Freshmen fifteen, though she had a good enough natural figure to carry it well. She liked telling jokes based on obscure cartoons or TV shows, and her smile was infectious. She was curved and soft and smooth and deliciously young.
She was also extremely naive and passive. She was the youngest of three, and was clearly used to having someone else be in charge all the time. When we started dating, she had only had one sexual partner, and he must have been terrible. She was frankly afraid of sex.
I was a young man, and I wanted sex. Naturally I started pressuring her straight away. To be fair to me, I really wanted for her to enjoy it. It made me genuinely sad to think of someone not liking sex. Still there was definitely a part of me that got off on convincing her to do what I wanted. Within a week, I she had given in.
Once she realized that sex with me was pleasurable, she was willing to do it whenever I wanted, which was a lot. I continued to enjoy pushing her limits. There was one thing that she wasn't interested in, and that was getting on the pill. She didn't like the idea of foreign hormones in her body. Maybe I could have pressured her into it, but this was one place I didn't want to push too far.
Both of us were afraid of pregnancy. Her elder sister, had gotten an abortion, and Emily was pretty vocal about looking down on that even though she worshiped her sister. My life plans didn't include fatherhood — certainly not while I was still in school.
As in all things, she was completely passive about birth control. She never brought it up or did anything to make sure she was protected. It made me wonder if she paid any attention to it at all.
On only the third or fourth time we had sex I get her hot and bothered and then went right in her without a condom. I fucked her for a few minutes and then pulled out, put on a condom, and we finished up normally. She didn't protest in the least, either when I did it or later. I don't know if she was too shy to speak up for herself, if she trusted me that much, or if deep down she didn't care.
What I did know was that I LIKED it. Look, I've heard a lot of opinions about how it feels to wear a condom. Sex with a condom is better than no sex, and when I'm rational I'm happy to tell you that it's better than an unwanted child. But, it does not feel as good as bare, raw unsafe sex. It's like you're always pushing against something that is just a bit restrictive.
So after she didn't say anything the first time, it became pretty common practice for me to start out without a condom and then put one on partway through. I probably started bare two thirds of the time. Now, I had read about the risk of precum, but I knew from marathon masturbation sessions that I didn't really make much. Sometimes if I was edging for a long time, I could get a drop out, but that was about it. So I wasn't really worried.