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Chapter 72
by
Yelawolf
you
allow her to do her things
Within moments you are stood before Claire in nothing but a pair of simple cotton panties.
"Wow, very nice. You must really love being a sissy, you're changing quickly".
"I suppose so..."
"Oh sweetheart please don't take that the wrong way. I'm happy for you, everybody deserves to find their place in life. It doesn't matter if you're straight or gay or whatever as long as your happy".
"I am happy".
"I can tell, these puppies are coming along nicely!"
She cheekily reaches out and grabs one of your boobs, tweaking the nipple lightly before letting it go.
"Hey!"
"Sorry Alex, just playing".
With the tension broken, Claire pulls a tape measure from her bag and starts to take all your measurements. She works concisely and fast, you can tell that she has done this before.
Once she has all your measurements, she asks to see your current wardrobe. After a while of looking through your clothes, she puts everything away and turns to face you once more.
"I'm impressed Alex, you've made a nice selection and everything should fit pretty well. I see you bought some bigger bras for the future as well. That's good".
"Thanks".
"Right then, let's have a look at your make-up".
You show Claire into your bathroom and she starts to rummage through the cabinet. Again, once she seems satisfied she turns back to talk to you.
"You've made good choices here as well. A nice selection of colours and nothing too whorish. This should do nicely for tonight".
"Still won't tell me anything?"
"Nope, let's take everything into the living room and we can start your makeover".
For the next few hours, you and Claire go through every item that you purchased yesterday. She explains proper use, when and when not to wear them, what they would match with and a whole host of other tips and tricks to getting the perfect look from your make-up. So much so that you are almost overwhelmed.
"Don't worry Alex, I know it's a lot. Tonight we can keep it simple and elegant and you should be able to adapt your own style from then on".
"Ok, we don't have too long before you're getting picked up so let's get properly started".
Claire spends the next half an hour diligently applying your make-up, she doesn't talk much during this time and you are content to simply sit there and let her concentrate.
Eventually, she holds up a mirror.
"What do you think?"
Oh my god, I'm looking at a different person.
I look beautiful, like a real girl.
Mr. Brown is going to love it.
"It's amazing Claire".
"No problem, now let's worry about what you're going to wear".
"Right, did Mr. Brown say anything about that?"
"He did, and he would like you to wear a dress. I have 3 here that I brought with me".
"You can pick which you want to wear tonight then I'll match it to a pair of heels and any other accessories I think would work as well as fix your hair in a way that complements the style".
"I'll also make some tweaks to your make-up to suit the colour".
"You can keep whichever you don't pick for another time".
"Great".
"Oh, I almost totally forgot. Mr. Brown told me to that you are not to wear any underwear".
"You're kidding, but I'm wearing a dress?"
"Yep, I get the impression he just wants to be able to bend you over whenever he likes".
"Fuck".
"So, the first is this cute red number. This would be perfect if you want to emphasize your lovely tits, really push them up and get them on display".
"The second is this small blue one. It's quite short and the way it hugs you is really going to show off your ass".
"Third and final is this one, a classic little black dress with a lacy twist. It's going to keep yours boobs and bum covered but with the right pair of heels your legs are going to look absolutely killer".
"What do you think?"
Do you want to wear the Red, Blue or Black dress?
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Sissies love big black cock
Sissy vs bbc
Story from edithis
Updated on May 27, 2026
by Yelawolf
Created on Nov 16, 2017
by Yelawolf
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