A couple of months ago I met the girl. She is perfect in every way, physically, emotionally, intellectually, and yes, sexually, except ... She dated a dude in a rock band before me, for about five years. And while I have no problems with that it turns out they had a very interesting sexual relationship. While we were out drinking one night, I asked her what were some of the "wilder" sex acts she'd performed. What followed caused me to sober up pretty quickly. Without going into too much detail, there was a lot of anal penetration, not to mention handcuffs, costumes, oil, honey, strange locations, you name it. And of course he had a big penis. None of these things individually bothered me, but all of it together! I realized I was like a rec leaguer suddenly thrown onto the court with the Miami Heat.
All of which adds up to an obvious point. I'm feeling pretty damn inadequate now. Our sex is new and wonderful, highly orgasmic, but relatively vanilla. In the back of my mind I'm always thinking, "Is she bored? Should I suggest something different? Should I tell her to get her dildo?"
Again, I just want to be clear that I am totally down and open-minded with exploration, and have nothing against just about any kind of sex (even the dildo, maybe especially the dildo). And the fact that I am with someone who has already proven to be sexually open, well, for many guys this would be like winning the lottery. But even so, I am constantly worrying that I come off as, well, amateurish, self-conscious, awkward. Right now things are great, but down the road when the new wears off ...
If You Don't Like the Answer, Don't Ask the Question
You can give yourself a long signature if you like. I'll just call you Lucky.
I don't see how you can go all that terribly wrong here, unless you get yourself all tied up in knots trying to live up to some standard you feel she's set for you. You don't have to live up to this other guy. You just have to be you. If she wanted to still be with that other guy, she'd be with him. She's with you because she wants to be with you. If you start trying to be that other guy, you're just going to louse it up. So cool off, Lucky.
If you want to experiment with something that excites you, do it. Obviously you are with someone who is open to new things. But if you don't want to experiment, don't experiment. I don't see why you have to. The big mistake you could make is assuming that your girlfriend is somehow programmed to expect the same thing from every man. That would be doing her a disservice. If she got the feeling that that's what you thought, she would probably figure you have no clue what she's about and she would dump you and then we wouldn't be able to call you Lucky anymore.
Again, I don't see how you can go wrong if you just concentrate on who she is and what she likes. Forget all the stuff about her other boyfriend. The worst thing you could do is compete with her ex-boyfriend's ghost in the bedroom. If that happens, you're dead. So forget about him.
Yes, I know, that may be a little like saying don't think about an elephant. So let's forget the negative form of that suggestion. Let's think about it in the positive way: Think about her. Think about her. Think about her.
Think about her some more. What do you want to do to her? What do you want her to do to you? Tell her what you want to do to her. Tell her what you want her to do to you. Take it as far as you want to take it, as long as it's real.
Don't fake it, though. Don't start cluttering up your act with synthesizers. You've seen what happens to rock bands when they start cluttering up their act? Keep it real and pure and lean. Stay true to your roots. Don't go all ersatz kinky on her or it's over. She'll sense it. She'll be thinking, where did this guy go? What did I do?
If that were to happen, she would have herself partly to blame. What woman in her right mind is going to tell a man she really likes all about the very wild and intimidating experiences she had with her most recent boyfriend, the rock musician? I'm not saying she's a terrible person for telling you, but it does appear that she lacks a certain capacity for calculating the effect of her remarks on others. It is fine to be completely open about one's experience, I suppose. I mean there's nothing morally wrong with it. But to pretend that what you tell someone about your sexual past isn't going to have a profound effect on him would seem to me to be naive.
No harm done, though. If you can keep the rocker out of your head (Think of her! Think of her! Think of her naked! Think of her in chains! Think of her on an album cover! Think of her upside down!), you'll be OK. Just concentrate on your girlfriend, and everything will work out just fine.
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What? You want more?