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My fetish is gonna come true. My girlfriend agreed to wear a maids dress during sex and role play a bit with me. She's very shy tho so it will probably be very awkward for her.

>What could I do to make her feel more confortable?

I don't really mind her getting flustered as i find it cute and her shyness just makes me more dominating. Tho... I find it hard to punish somebody who's already so scared.

>What kind of orders should I give her during the role play?
>What punishments should I give her if she disobeys?

Pic related but its not my gf or the dress she'll be wearing. i already bought it and i have it so i guess i could display it.

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Translation: I'm going crossdress as a maid tonight and get fucked in the ass by a sonic cosplayer.

These are really questions you should be asking yourself since it is your fetish.

Just be nicer to while having the foreplay then you have been ever befor, this could help a lot.
Even if so, Crossdressing maid are even hotter ;)

i was expecting you guys to give me crazy suggestions like sharpy in the pooper.

Show gf and show costume, has she seen the costume yet? Did she put some rules?

Shave her head bald and use the hair to give her a beard.

Ok one sec

I second this

this

Make her clean your house. If she refuses or fucks up, spank her ass till it is bright red. If she fucks up again, make her wear a butt plug. Bigger plug as an option on 3rd fuck up, or spank her tits. Fuck her or make her blow you between each task, but make sure she doesn't cum until she is done cleaning and has 5 or 6 loads of cum in her stomach.

Thats a good idea acutally

Here she is and the dress. this was her first time wearing it and she sent me this.

Show us the outfit!

Don't hold back if she starts crying, timid girls just need you to push them.

LMAO so it was a guy after all
Nice Maid outfit tho!

lol
yeah i'd love that~

I fucking called it.

Now where is sonic at?

A Hot crossdressing Maid the best thing what could happen ;)

Moar

...

Tell "her" to sort that fucking hair out. What a mess

Oh god thank you, tell your girlfriend that she really looks great in this dress.

Only if she has a bigger dick than mine tbh

>Glasses
Not sure if it was part of the outfit too but damn that makes it hotter

Thread theme
youtube.com/watch?v=hU7EHKFNMQg

I would give her/him/you or the sonic cosplayer the following orders
>do the dishes
>clean the house
>answer the door and phone
>vacuum (Hoovering up)
>clean the windows
Punishments if these things are not done
>lower bonus
>less time off
>firing
Also don't forget you have to pay SS and health insurance in California and Maine as well as the UK. Enjoy your stupid little game.
>

give her simple stuff to do so it's not overwhelming fr her first time

>call you daddy or sir the entire time
>only do the things you explicitly ask her to do
>do those things as exactly as you say them to her

Punishment:spanking her (5 times on each cheek) modify as you see her react. Tell her you know she's trying her best and you proud of her. You're only punishing her because you care about her.

Easymode for dom/sub introduction.
>

>She's very shy tho so it will probably be very awkward for her.
>>What could I do to make her feel more confortable?

why would you do this? the shy and unconfortable trope fits maids perfectly

Just have her be shy, you can go with the "master" name calling and shit but other than that shy fits the profile perfectly.