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Being okay with lack of sexual history
(Alt used because my boyfriend knows about my regular account but wouldn't read a relationship thread unless he knew I created it)
This isn't about me but my boyfriend. I'm 26 and he's 23 and we've been together for a little over 2 years. Before we met, he had never had a girlfriend and is not the type to go around having random sexual experiences so I was his first pretty much everything. It bothers me how much this bothers him sometimes. I feel like I'm not enough, like he resents me for being a good fit and not giving him an excuse to break up with me and meet someone else, and for having been fairly sexually adventurous myself for a few years before I met him.
I place value on honesty over monogamy and would actually really like to have another woman join us some time, but single bi girls who are down for a three way are called unicorns for a reason, so the search is going somewhat slowly. I would even be okay with him meeting someone and being with them without me as long as everyone knew what was going on, but he's very shy so going out and meeting a girl AND explaining to her that he's in a relationship but it's cool because I know about and am okay with everything would be very difficult for him.
Part of his problem is that most of our friends have histories more similar to mine than his and aren't shy about talking about them. This leaves him feeling left out of a lot of conversations and like a kind of freak afterwards, like he's missing this essential experience the rest of us have. I've never hidden my past but I haven't thrown it in his face either. I like to think that we have a good, satisfying sex life and that we communicate well but this really hurts me sometimes and I feel like a jerk bringing it up to him because I know he's entitled to his feelings. The thing is, I think he's blowing it out of proportion - it's really no big deal, he's in a good relationship now and I'm not even demanding that he choose between being with me or exploring other sexual avenues as long as he's honest. When I try to get that across, he tells me that I don't understand what it's like to be a 21 year old virgin (true but I don't know how relevant. I did my part, I cured him of that condition...).
How do I help him to be okay with this? Everything else is great but I'm tired of feeling like an obstacle to his happiness, or the happiness he assumes he'd have if only he knew what another vagina felt like.