Should I let girls crossdress me as a forfeit to a bet?

[Anonymous2207]

Hey Y’all, Last weekend I went out for drink with two of my female friends and as we got talking I accidentally revealed a secret about me how I had dressed up as a girl partially ( draped a saree over my boy clothes) as a forfeit to a bet. For some reason the girls got a little excited and got me into a bet where if I lose I let them completely crossdress me for the following weekend. Unfortunately I lost and now I have to show up at their place for my weekend as a girl. And they promised to make me look ultra feminine. And just now I received a photo of the lingerie they bought for me. I am confused whether I should go as according to them I will “the doll of the sleepover” with their other female friends coming over. I am worried that given I am not huge and muscular (waist size 28)I will actually look like a girl instead of a man in a dress. So should I go or should I ditch them? Probably will kill the friendship.

[Pariahterror]

I myself would totally do it. But that is me.

But since you will be with the girls, maybe tell them how you feel about it and keep it between you all. But make sure if you don't want to, not have the girls present who weren't part of the deal.

Maybe they will allow you to change the ante if you make it clear how troubled you are with it. Just try to talk over it first before doing anything rash.

[PrincessJessica]

I'd enjoy being the doll of the sleepover Although I normally say a bets a bet and you should follow through you shouldn't feel like you need to do extra additions that weren't discussed before (like extra people). If you talk to your friends maybe you'll find a way to make it easier for you to keep up your end of the deal (like maybe x-dress just for them first so you're a little comfortable before larger crowds). Going from small time cross dressing to taking it up to exhibitionist levels is quite a scary leap.

Hope you'll work something out with your friends and, assuming you go through with it, enjoy it at least as half as I would.

[Anonymous2207]

Dude it has gone way over that as of now. Apparently I had agreed to the people for my x-dressing. There will be a total of 5 girls. And now they made me agree to a cock cage and a butt plug in return of no pics on the internet.

[InnoTheFox]

This could go either way. As it stands it sounds worth a shot to me! Friendship gets messed up, and you have a life-changing experience. OR your friendship gets strengthened and you get to do kinky activities on the reg

[RiskyFlame]

Originally Posted by Anonymous2207

There will be a total of 5 girls. And now they made me agree to a cock cage and a butt plug in return of no pics on the internet.

Made you agree? This sounds like either someone's fantasy or a blackmail situation. These two motives apply to posting a thread such as this one as well, for the fantasy or getting honest advice. Assuming this is real, you posted this thread because you have doubts about whether you'd want to go through with the cross-dressing activities. But even when you're in doubt, you are content with those five girls coercing, or threatening*, or even blackmailing* you so they can chastise and anally plug you as well? Unless you want this exact situation to play out without knowing what will happen next, don't listen to those threats and go to the local authorities with evidence that they are forcing you to such sexual activities.

And by the way, in your first post, you wrote that you'll be visiting them cross-dressed the next weekend. So how can they already have obtained pictures of you and made you agree to wearing a chastity cage and anal plug?

* "Performing sexual activities and in return, they won't post the pictures of you online" sounds pretty much like a threat to me. Correct me if I'm wrong though.

[Anonymous2207]

Dude they are my friends. We go to grad school together. They don’t have pictures of me. They just said they aren’t going to click or post any photos when I get dressed. And more importantly I kind of know they are joking with regards to the cage and plug thing because I know them extremely well since 3 years and neither of them have such things. They are just trying to get me all nervous. But what I know is they want me to crossdress so that they can make fun of me.

[RiskyFlame]

Sorry, I'm just cautious and only know what I read. If you trust them then I think you should do it. But I suppose that your choice also depends on which clichéd rule you live your life by.

"Better safe than sorry" OR "no guts, no glory."