Hi everyone, I'm in a difficult position. I'm a virgin in my mid-20's and I have a gay friend who has invited me to his place for dinner tonight. I'm really naive and I'm not sure if that's an invitation to do other things as well. We don't really know each other too well, although we've hung out with our mutual friends several times. In case this is more than dinner, though, I need advice. While I really DO want to experience sex for the first time, I'm really afraid of it and I'm not sure if this is the right person. I think he's cute, but we have very different personalities and I'm not even sure if he's looking for a relationship with me (or if I am with him, for that matter). He talks about sex in a very casual way, while to me it really does mean something. Also, sometimes I feel like he's not very sensitive to my feelings, and I'm a really sensitive guy. I don't feel that the trust I'm looking for is there yet. I'm also afraid of how I might feel about myself afterwards. I've always imagined having sex for the first time with someone I really care about and am committed to--but at the same time I really just want to do it. But if I do, then will I feel like I've lost something important in a careless, meaningless way? If he makes a move and I still feel as conflicted as this, what should I do?
I think you should give yourself time. I don't think you should do something unless you feel 100% comfortable with. It is ok to set boundaries and let him know what you're comfortable with. If he's not respectful of your needs and desires then there is a bigger problem there.
Just to get it out of the way, I hope age isn't a factor in all of this but I somehow feel that it is. You should never feel pressured or "obligated" by anyone or anything to have sex. It's a decision you make when you feel comfortable. I am in a similar position as you, so I know where you're coming from. But for me, I personally made the decision to only share that experience with someone whom I can deeply love and trust. With that said, there's nothing wrong with doing it for any other reason because each person is different. If he makes a move and you feel conflicted, you should openly express that to him. Set out boundaries for yourself where you feel safe and comfortable. Perhaps talking about it first? If any of these boundaries are crossed (i.e if he doesn't acknowledge that you feel uncomfortable and persists to make a move), he has disrespected you and I'd say it is time to leave.
If he deserves you and wants you more than for a one night stand he surely will not attempt having sex from the first date or will back off the first sign of discomfort you show. Otherwise he's a no-go.
I can say that I decided at 20 to have a one night stand with a girl that I only knew casually for a couple weeks, and I would not recommend it. I am demisexual, so that may play a factor... But I felt like I missed out on the opportunity to make my first time be something special. Without the deep emotional connection, it felt like I was going through a set of motions without purpose. It felt good physically, but it left a hollow feeling that really made me question why our society is so obsessed with sex. When I was with my long term ex-girlfriend, it was completely different to the point of being similar to the difference of masturbation versus sex for me. If I had the choice again, I would have told myself to wait for someone who I really cared about. I don't know what type of activities you would like to try, but I couldn't even imagine being able to relax enough to make bottoming be pleasurable with someone who I was not very close to. Just my 2 cents. If you decide to go for it, just remember to be safe!
I think if you read your post it answers the question of whether you should or not. No matter what your age, I believe that sex is something meaningful and should be done with the right person or someone you really love and care about. You say you really don't know him so I would suggest waiting and if he's the one it's supposed to happen with it will
