Female almost 30, and it’s just worked out in life that with my past boyfriends we never got far into the sex stage. I was also very career focused and it had gotten to the point for me where I was starting to feel embarrassingly old to be a virgin still. At the start of my new current relationship things moved quickly and on the first in-person date the topic of sex was brought up. I knew he (M31) was fairly experienced and when he started asking what I like during sex regarding foreplay positions etc, I couldn’t bring myself to admit I had never done it. A few dates later and we went for it. He struggled to get it in and I blamed it on needing to relax. It definitely hurt a lot but I got through it. The next few times hurt less and less, and now OMG do I love sex. He comments often that he loves having sex with me and that I’m the best sex of his life. I feel so experienced and get to experiment all the time now just from being with this one person.
But I do often have in the back of my mind should I tell him? Would you want to know now -months later- if you were in this situation? Or does it not really matter (especially when I personally don’t believe body counts matter if you’re having safe sex). I worry about the possibility he could feel weirded out by learning the truth because he has this belief that I have been with many others before, which I’ve never challenged or confirmed.

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