STEFF ANSWERS: Keeping in mind that conservative attitudes about sex are usually resulting from ignorance or fear, I think you gotta proceed slowly.
If this were me, I’d probably proceed in any one of a few different ways. In fact, I’d recommend trying them all. Education shouldn’t happen in one fell swoop, neither should sexual expansion. Slow, graduated learning will make it more meaningful for both of you, if that’s what you’re after.
1) I might write him a very naughty, explicit letter detailing a few things I’d like to do to him. When he’s leaving one morning/night, put it in his wallet or something like that, so he finds it at an unexpected time and place. When it’s out of the blue and he’s alone with time to process things, and not in front of you, it may leave him more open to suggestion. Plus, if you’re arousing enough on the page, he might just find himself in a situation where he wishes you were around to aid with relief. (This could possibly backfire, too, so you need to be careful how far you go on the page. Subtly alluding to things could be as big a turn-on as being explicit, depending on your man.)
2) I suggest just taking him by surprise in bed. If he’s never done bondage, for example, maybe don’t talk to him about it in advance if you believe he’ll cringe. While you’re on top, simply playfully pin his arms over his head and loosely put a pair of nylons or something else that you’ve got conspicuously handy around his wrists, so he can get out if he likes, and proceed as you like. So, make it the illusion of bondage instead of the real thing, to take the fear out of the experience. (I wouldn’t recommend blindfolding with bondage at the same time if he’s nervous. It can be pretty overwhelming when you’re knew to it, speaking from experience here. ‘course, I fell in love with the feeling, but still, a lot to process.)
3) Another way to proceed is to just introduce one small new thing per session. Bring in food one time. Start off with a massage and oral another time. Try nailing him publically in a forest or something sometime. Vary the experience one teensy way each time until you’ve acquired a kaleidoscope of shared experiences. Then you’ll get to pick and choose.
4) Something else to try might be something like 101 Romantic Nights (a sex game where you roll the dice and refer to a book to see what your tasks for the evening are) or something similar, where you’re told what to do next through a book or something. There are other books, like 101 Grreat Nights of Romance, that come with sealed pages and just a tease as to what might lie ahead. You break the seal on the page to get the instructions for the evening, and you do what you’re told. They’re pretty tame, by and large, but they’re definitely an introduction to thinking outside the box when you’re a conservative lover, plus the creativity included might be pleasantly surprising for him, but the instructions and tips might take some pressure of of him when it comes to performing. But there are also a lot of inventive little role-playing antics and such, with a list of what you might require for the evening — and some of these may be new to experienced lovers, too.
5) It may well be that he’s intimidated by your experience. Bring the issue up casually, in a non-threatening way, when you’re having a quiet night on the sofa, watching a movie. Discuss the intimidation and tell him you can understand it if he feels that way, but you don’t want him feeling it anymore, and ask what you can do to help make it go away. You can ask him to design a night that will be comfortable for him, but he may feel pressured as a result, so I don’t really recommend that.
I think a lot of chicks tend to forget that, when it comes to sex, a lot of pressure, most of it (if not all), is on the guy. Their plumbing needs to be working, their size needs to be adequate, their skills are the ones that dominate the experience… an inexperienced guy with an experienced chick probably has a whole lot of issues to deal with, and being relatively gentle yet provocative is the only way to proceed if he’s timid.
6) Finally, maybe you can just watch a movie with a great sex scene in it, like the infamous refrigerator scene in 9 1/2 Weeks, and teasingly suggest you should do that, or any other sex scene you’ve enjoyed cinematically. I’m talking films, not porn. I don’t think porn’s the way to go when you’re easing someone in, since the expectations could seem unrealistic. But after you’ve said, “hey, that looks like fun, could we try that?” take him by surprise and go down on him.
Personally, all of my sexual experimentation came as a result of conversations that got the ball rolling. But I’m an imaginative and visual gal, so maybe it impacted me more that way.
In short? Again, be provocative but gentle. If he seems to be getting intimidated, then address it in a non-judgmental way. Let him know you want to teach him, that it’s important to you to show him just how good you can make him feel in every single way. You can bring dominance into the equation after you’re both on level ground. Have fun getting there. ;)
Do my male readers have any suggestions for Miss Anonymous, or feedback on mine?