[jacksonhole]

I have a suggestion for you Tim. I have used Truth or Dare a lot in the past and it is incredibly effective, and I have seen people go way beyond what they expected to be willing to do both because they were caught up in the game and because as you point out, “the dare made them do it” so they have an excuse.

My first suggestion is to not have her be the entire focus. Have dares that are gender neutral like mooning. Have you and your friend also doing dares. Don’t make them all nudity based. Silly things like singing a song or putting on a goofy outfit or barking like a dog are all ice breakers.

The key with dares is to start very tame, and to always do the dare. Then another tame dare, and do it. Everyone is doing silly stuff for a while, but more important, everyone is “doing” what the dare says to do.

After a while, when a more sexy dare comes up, and I encourage it to be mooning, have you or your friend do it first. Maybe even a few dares for the boys before it gets to her. And don’t make her dare be too far removed from what the last dare was. Generally if one person moons the group, the next person getting that dare will just jump up and do it. They don’t want to seem like they aren’t playing along. You don’t want any big jumps that make it feel like the game just changed to something else. It should build organically.

Your wife has a thing about only showing one breast? Use that to your advantage, eventually have a dare that is to show one breast. Maybe later there is a dare to show the other breast. It wouldn’t surprise me at all that once she has shown each breast one at a time, she will feel different about showing both at the same time.

Then maybe a dare to draw a smiley face on one breast. That combines her “one breast” thing with doing something silly. Keep them feeling fun and silly for as long as possible. Draw on the guys asses before drawing on her breast. Don’t ask her to do something that the guys aren’t willing to do.

And whatever you do, don’t make her feel like the entire game is a setup to get her naked. She will have her guard up the entire time and even if you start slow, when you try to do something bigger she will be like “aha, I knew this was just an excuse to get me naked!”

I did this two months ago with my wife and a friend of hers. When truth or dare came up (my suggestion) she flatly said not a chance and said it might be time for her to go home. But we got her to stay by keeping it really tame and mostly doing truth for a while. The first nudity related dare was me mooning the two of them. Then my wife mooned, and the friend didn’t even have to be dared, she just stood up and mooned us.

30 minutes later the girls were both sitting around topless, but only after I had been bottomless for ten minutes.

The next round of dares involved touching boobs, butts and my dick, but only quick squeezes, and only because we were all half naked for quite a while so that barrier was down. Once the touching was “normal” and everyone had been involved it became kissing or sucking a nipple. My wife sucked my dick for a minute and the friend commented that was “so hot”. But it was just the next thing to do, it didn’t feel like a big jump.

Eventually the friend asked if we could do a couple truths again, and she immediately asked if we had ever had a 3-some, which we had. We asked her, and she had not. Then she asked if we could have one tonight.

That’s when the game broke up, and we did indeed end up having a 3-some with her. And it was awesome.

Not suggesting it will go all the way to a 3-some, or that you even want it to. Most of the time it doesn’t go that far, but if you follow this approach, and don’t make it feel like it’s all about seeing her naked or getting her to do stuff, you have a good chance of having a really fun game.