These two are in heavily in debt and are not able to pay them of.
 
As a consequence they are sold as slaves and have to serve their new mistresses until their debts are worked off.
 
 
Trixie is sold to Rarity who still has a serious grudge against her for ruining her mane.
 
Rarity takes great joy in bossing her new slave around all day while teasing and taunting her.
 
She also further humiliates her by forcing her to wear revealing outfits and work as her model.
 
 
Gildas new mistress is her former friend Rainbow who forces her to apologize to Pinkie, Fluttershy and everypony else she hurt.
 
She is also forced to do Rainbows household as a maid and to help Pinkie in the bakery while enduring her endless talking.
 
To add insult to injury Gilda has has to serve as willing test object for Rainbows countless pranks.
 
 
Trixie and Gilda are suffering greatly under their miserable predicament for many months and cannot wait until their debts are finally paid off and they are free to go.

I would definitely tickle torture them.

@Lucky424  
Trixie: well all in all not the worst day of my life you
 
Gilda: not even In my top ten

@Background Pony #D4D5 ‘Returns an hour and half later, accompanied by two guards.’
 
Apologies, my dears, it took longer than I expected, but I managed to get something you might both enjoy.
 
‘The guards remove the shackles, but slap a single cuff on Trixie and Gilda’s wrist, a small golden glow coming from each.’
 
You are free of the shackles, but these cuffs will keep track of your location at all times. Come, I will show you to my estate. It’s a nice little place overlooking Canterlot Waterfall.
 
(I may just keep this in mind for when I have time.)

@Lucky424  
Gilda: I guess I can work like that

I could so see Gilda and Trixie being hate friends who get into trouble

@Background Pony #D4D5 I plan on having you free within the hour. Well, from the walls at least. The shackles will remain for now, but that is not my decision, that has come from the judge if you took my offer.

@Lucky424  
Trixie: ok how long will we be like this
 
(Cool if you can’t do it now you could just hold the idea for later)

@Background Pony #D4D5 You say that, Miss Lulamoon, but I know that look in your eye. I’ve seen it before. And I can understand that, Miss Gilda. I give you my word that, other than the uniform, nothing untoward will happen.
 
I’m afraid you’ll have to wait here whilst I let the judge know your decision, and will collect you when I am done.
 
(Dammit, now I really want to write a fic about this, but I’ve got 10ish going already!)

@Lucky424  
Trixie: ok but trixie will not enjoy it
 
Gilda: I’ll do it if only to stay out of jail

@Background Pony #D4D5 Well, you are dressed as maids. Maybe some dusting here and there. And don’t worry about any of my other staff. In anything happens, come to me and I’ll see that the correct action is taken against them.
 
Obviously, if you refuse my offer, I will be forced to pursue legal action, which will most certainly see you serving jail time. I’m pretty sure all the both of you do not wish it come to that, the same as I do.
 
So, what do you say?

@Lucky424  
fine i’ll take that one and what do you mean ‘within reason’

@Background Pony #D4D5 For the most certain, it is option 3. Six months, doing various tasks around my estates. There won’t be any jobs that you may find degrading (within reason), as I have other staff for that.
 
But the uniform is non negotiable. After all, you both look rather fetching in those outfits.

@Lucky424  
gilda: no tell me straight what do we have to do to work for you the least amount of time and not be prosecuted or pay out of our pockets

@Background Pony #D4D5 It depends on the arrangement we come to. It could be less time, it could be more.
 
Why don’t you and your friend come negotiate with me over a nice glass of wine?

@Lucky424  
trixie: well i do need the job but will option four be any quicker

@Background Pony #D4D5 Oh… at least six months. It took me years to get my collection up to its current standard, and millions of bits.
 
And depending on how you do, after option 3’s time period ends, there may be a job in it, for the both of you.
 
What do you say? Oh, and to ensure you stay and don’t try to run, the shackles will remain.

@Lucky424  
gilda: so how long will options three and four take

@Lucky424 I would choose no 1. I need some more prosecution praxis. Also choose civil process, not a criminal one - more money.

Now now, my dear mares… mare and hen. You broke some of my most valued art purchases, so we have three solutions.
 
1)You opt to be prosecuted for destruction of private property;  
2) You pay for the damages, which I’m fairly;certain you won’t be able to.  
3) You work to pay off the debt, to my terms. Which means we add some suspenders and stockings to your outfits;  
4) We find ‘another’ solution to the issue. It also means we’ll add stockings and suspenders as well, but this time you lose your panties.
 
I know which one I’d prefer.

Well my pretties, now that I have you in my clutches it is time unveil my horrible plan…
 
BEHOLD! PICTURES FROM MY VACATION IN MAUI! MWAHAHAHAHAHAHAHAHAHAHAHA!