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

[thenewslave]

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)

List of clothes:
-black pantyhose (cotton)
-small red bra
-bigger green bra
-dark green dress
-small black purse
-short (dark) green jump suit
-white high heels
-black heel boots
-black curly wig (a cheap one)
-black and colored panties
-black ballet flats (sadly not fitting very well)
-whole lotta makeup (from my mum actually)

List of toys/things in my shelf:
-small buttplug
-huge buttplug
-anal beads
-big anal balls
-12inch double dildo
-inflatable and vibrating buttplug
-small metal plug
-breathable ball gag
-jennings gag
-chainless metal handcuffs
-wartenberg wheel
-7 ropes
-glass dildo
-nipple clamps with hooks
-a few cheap blindfolds
-wooden spoon
-black cane
-black leather collar with O-ring
-heavy metal collar with O-ring (connected to a pacifier chain and a pacifier)
-pacifiers
-feeding bottle
-self made tongue clamp gag (like this: http://tinyurl.com/o2wqkgm)
-cheap blue handcuffs
-metal chastity cage
-plastic chastity cage
-leash
-metal chain
-big black cock with strap on harness
-bondage tape
-candles
-buttplug-cockring combination
-condoms
-latex gloves (medicinal)
-small items like bullet vibrators and dice
-multiple bottles of lube
-toy cleaner

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.

[thenewslave]

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

[x5799]

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 ☠😜

[getdaring]

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.

[bubba51]

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

[thenewslave]

Originally Posted by getdaring

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.

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.

[thenewslave]

Originally Posted by bubba51

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

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.

[thenewslave]

Originally Posted by x5799

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 ☠😜

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
The piss dare sounds a little extreme to me

[Blue Griffin]

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.

[thenewslave]

Originally Posted by Blue Griffin

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

[thenewslave]

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

[Berserk]

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.

[Blue Griffin]

So any results/report on how this went?

[thenewslave]

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