Female friend dressing me up for the first time, give me dares please
 

Hi there, I have a really hot female friend that I just outed myself to (as a Crossdresser). Tomorrow she will be dressing me up and giving me a beautiful makeup, and will take portrait photos of me afterwards.

For this I want some dares to make it extra exciting, can you help me with it?

Below I will describe the situation the best I can and give you the limits, I really hope you can come up with some great stuff.


So the girl knows I'm into kink, but doesn't know details. She will be visiting me first, because she wants me to give her a little fashion show to see what clothes I have (See list below).
I already have all my toys (also see list below) for display in my shelf so I expect her to see it, but SHE SEES ME AS A FRIEND AND HAS A BOYFRIEND so there is no way I will be able to do anything with her. She is only interested in helping me as a friend so keep that in mind.

After we are done we MIGHT go to the mall and shop some things that we need, and then we drive to her place where she will make me beautiful. She also has 2 dresses she doesnt need anymore so I will try them on at her place and can keep them, too. After that she will do photos of me and then drive me back home again because her boyfriend will be back after a while. (If we don't take that much time there might be some time to chill for us - the perfect time for some hidden dares :P)

I also have transparent Latex socks and long black latex stockings (and 1 long black glove, the other one ripped).
I really have a latex fetish and would love to include those items in my fashion show/maybe even wear them for the dressing up. But I don't want to impose my kinks onto my friend who just wants to help me and has nothing to with the kink world.

So this post got pretty long so I give you some ideas that I imagined:

-expose my kinks a bit more to her so that she will ask me about it (maybe she even wants me to show some things?)

-make me feel a bit embarrassed

-general fun / hidden dares that one can do with friends around

This is really simple insert the inflatable plug before you ever see your friend and every time you get into a new outfit inflate it keep it in the rest of the day. But we are not done you also have to have the chastity cage on at all times. Finally if you do go to the mall every half hour go to a restroom and in a stall piss but not a drop in the toilet. ENJOY ☠😜

So what exactly does your friend know when it comes to you being into kink. Have you told her anything yourself or has she just worked it out? Would you tell her about the dares or do you want to keep this completely a secret from her?

So as for something hidden you could do tomorrow, how about wearing your female underwear in a wedgie or giving yourself a wedgie in front of her.

Post the pictures she takes without face. Wear your green bra and colored panties. You must always be in a dress or skirt for this. If cold you can wear the pantyhose

I just told her I'm into SM and she now knows I like to dress as a woman but thats all. I don't think she knows what side I play or what kind of fetishes I have (she basically only knows I go to some sm munches and the rest is up to her imagination).
I want to keep the dares a secret because I do not want her to think I see more in her than just a friend.

I like your dare, since I didn't actually feel the need to wear female underwear because she would never actually see it - but now I have to.

Thanks for your dares. Posting the pictures really would be exciting but she already told me she basically only does face pictures so this might be difficult.
I think I can definitely manage to wear panties and the green bra, but the dress dare kinda reduces the outfits I can wear drastically.
We will see what we work out tomorrow.

But please keep the dares coming I am very excited, and I will post reports for you of course.

Thank you for your dares, but I fear they might not be possible for me :/
The inflatable plug is way to clunky to wear while getting dressed up and I actually like the idea of me getting hard while she is near, she might even realise it :o
The piss dare sounds a little extreme to me :(

Write some questions/answers on your body so she might see them and ask about them. (How you go started, favorite outfit, etc) or something like flip a coin heads answer a question, tails you get gagged/pacifiered for the next outfit.

Or just talk about/drop hints about your clothes.

A wedgie or bra connection wedgie would be fun.

Every time you go change, you must drink from your baby bottle and spank your butt with the spoon. Leave the door open so she might see you.

Kinda hard to think of mall dares if you don't do public.

Thank you I will definitely try some of these :)

You can give me some small harmless public dares, maybe I can do them. Remember that she shouldn't know what I'm doing.

Pls keep them coming there's still some hours left :)

Im gonna bump this because in not even 3 hours my friend will be here

See if she can incorporate a toy or two into the photo shoot, just for a shot or two each. Pacifiers, bottle, even rope would be easy... Others, she'll have to be more creative.

So any results/report on how this went?

I'm currently in the hospital so sorry that there aren't any reports yet