I just want to warn you, losing your virginity for loneliness will worsen things. When you have no connection, it doesn't feel as special and you might feel used afterwards. But if you're losing it because at least you know what it feels like... just the act in itself, it should be okay. Good luck out there.
If what you want is connection, sex isn't some unknown locked achievement. People find it all the time once they actually start looking in the right places instead of assuming they're disqualified. The pain you're describing isn't proof you're failing, it's proof you want closeness and I'm positive if you find the right person they'll gladly accept you.
Trust me sex isn't all that. A random hookup can be fun at times but it's much better with someone you care about. It makes every aspect of it better. But it sounds to me like you are linking your sense of self-worth to your ability to have sex. I did it for years. I just wanted to prove to myself and others I was desirable and now I have a weird relationship with sex and sometimes I struggle to perform. I wish I could go back and wait to have sex with someone meaningful. Please try and reframe your thoughts about sex.
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