Losing your virginity is a big deal. It's not uncommon to have all sorts of romantic and exciting fantasies of how your first time will play out. But for most people, the reality is that their first time having sex was less than perfect. It makes sense that with lack of experience, nerves, and some pretty skewed views of what sex actually looks like, that people's first times are usually not so great or not what they expected. Reddit users shared some of their awkward, funny, and downright embarrassing stories about losing their virginity. Of course, these examples of first times are just for fun, as we can't independently authenticate the stories. We spent almost the whole night trying to get it in. Every time he would insert himself a little more and he'd have to pull out because it hurt me so much. It took about seven attempts and 16 hours to get him fully inside me.

How to say Yes! to sex (and not just 'OK, only if you shut up about it') | Jacqueline Hellyer
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There are many varying definitions of virginity. And yet one can be a virgin who has had considerably more sexual activity than their contemporaries. One can thus be a virgin and yet give the most amazing head a person could ever receive. What hope is there for them? This is one of the aspects that trips up many virgins. There are no universal secrets to pleasing another person, man or woman. Not every guy loves blowjobs. Not every woman likes cunnilingus. Some may like a finger up the backdoor while others may react violently. Speaking of learning the right lessons….
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We finally lost the V-card 3 days after the wedding. I was too shy to help guide him in. Repeat for a few days until finally BOOM! It hurt for a second and it was over another second later. It helped that neither of us had high expectations that it was going to be magic the first few 50 times. We still tease each other about it now. The first time was great and funny to look back on. We went at it at least one other time that night and then were humping like rabbits as soon as we woke up the next day. Also lingerie looks really good on beautiful women in real-life, too. And it was enjoyable and fun despite not having mind blowing orgasms.
But how does it feel to be a virgin in your 30s and 40s? I only recently fell in love properly for the first time. He seems to accept me exactly as I am. I feel like we are soulmates.