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Even though you think you know him, there is a point where you'll cross the line and he won't take kindly to it. He did say not in front of his friends. While you took it literally, I'd bet it's because he doesn't want to hear about it after the bet is over. If you involve your friends, he'll likely be embarrassed by them later and it might get back to his friends. You also have to decide how trustful your friends are. I can imagine one of them taking photos or a video and it later gets out. Do what you want, but know that there will be consequences should you go too far, no matter how well you think you know him.
Hel'll either take it well, or dump you. Only you can judge how far is too far for him to go. And if you humiliate him in public, you can count on similar treatment in the future as things will probably escalate.
I think you should tie him to the bed and have you and all your girlfriends give him oral sex all week long.
OP, if you think this is good advice, I'd be willing to bet you that I can do a standing long jump of 75 feet. (while I'm bound and blindfolded, just to make it fair and all....)
OP, if you think this is good advice, I'd be willing to bet you that I can do a standing long jump of 75 feet. (while I'm bound and blindfolded, just to make it fair and all....)
While it wouldn't be a good idea for me, I trust you know your BF well enough. Having read all your responses, it sounds like you guys are open and adventurous. My guess is all the people that just KNOW (better than you) are the same types of people who KNOW that a certain type of relationships isn't right, or that anybody who says one thing really means another.
Take the advice others gave, but take it with a grain of salt, have some fun, and push it as far as you think you need to. Not further. Do bear in mind that if you dress him up like a french maid, that others may unwillingly be involved. I'm pretty open, and all kinds of crazy sheet goes down in private with me, but at the same time, if I had my pre-teen daughter at the mall, I really would not look forward to explaining to her about the bearded x-dresser at Victoria's secret who is getting all the attention from the "popular girls". It would really undermine some important live values I'm trying to instill. (not that I would have her at Vic's Secret to instill them, but might be passing by....)
What about hosting a party (at home) and having him dress up and provide tea service (or whatever).
And I do think it's a damn good idea too give him some recognition at the end. If you play him hard, that's fine, but at least show some appreciation (like the pedi idea).
Good luck, and tell us what you do, and how it goes. (please)
TBH, I think he'll look kinda good wearing that stuff. With his body type, I'm pretty sure I can make him into a convincing (or at least passable) woman. Not to mention, it'll be fun to sorta make it into "girls' time."
OK, two points.
1. You seem dead set on dressing him as a woman, and all your poll options include that, so I guess it's a done deal.
2. If your boyfriend is a big ex-football player type, please don't do this. But if he's a small-frame, thin guy, then do the woman thing, but you have to go ALL IN. That means really make him look like a woman, not like a man dressed as a woman. That will at least reduce (or eliminate) the amount of embarrassment and finger-pointing you cause him out in public.
That means no facial hair, a wig, lipstick, shaved legs, the whole 9 yards.
You willing to go that far?
What if he enjoys it?
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