Humiliating Shopping Dare

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jdoh
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Re: Humiliating Shopping Dare

Post by jdoh »

Ok, so if I compile what has been suggested so far, I should purchase a ruffled blouse, perhaps in a lighter blue or white, pencil skirt or trouser, and high heeled color matched boots. Thoughts on foundation garments?

For the other outfit I think flirty meant something date suitable from the context of the assignment. Thoughts there?

Finally, since someone suggested slutty, I'll take input there too, perhaps something that transitions to the bedroom?

Gulp, this is going to be some shopping trip. :gag:
TheWingmen
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Re: Humiliating Shopping Dare

Post by TheWingmen »

I think we can cover the "something that transitions into the bedroom" and "foundation garments" in one go?

Maybe a matching pair bra and thong (something a little fancier than everyday wear, real silky or lacy, and in sexy colors perhaps red and or black) Then a matching garter belt holding up some thigh highs. When dressed fully it will just look like you're wearing some hose under your skirt. But underneath you'll be dressed to kill in the bedroom 8)
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ponylady
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Re: Humiliating Shopping Dare

Post by ponylady »

as jenny mentioned a tiara you for sure shouldn't forget the accesoires.

stylish handbag, jewellery (extralarge kreoles would add something to the business secretary outfit that would emit a certain "vibe". that, and find a nice choker.

once finished, you may look & act the secretary, but some small changes can convert your outfit for the flirty date. opera gloves (depending on the armlength of your blouse), a bit more risquier skirt (short in front, longer in the back).
and don't forget to take a close look @ wristbands.
it's the little things that hint @ the slut behind the facade.

have fun shopping.
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jdoh
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Re: Humiliating Shopping Dare

Post by jdoh »

So after setting this idea aside for a while, my mistress is considering it again. Gulp...
TheWingmen
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Re: Humiliating Shopping Dare

Post by TheWingmen »

jdoh wrote:So after setting this idea aside for a while, my mistress is considering it again. Gulp...
Be sure to let us know how it goes!
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bound_jenny
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Re: Humiliating Shopping Dare

Post by bound_jenny »

jdoh wrote:So after setting this idea aside for a while, my mistress is considering it again. Gulp...
The "Gulp" is a nice indication of how evil Mistress is. Hopefully, very evil! :whip: :twisted:
TheWingmen wrote:Be sure to let us know how it goes!
I'm rooting for Mistress.

Jenny.
Helplessness is a doorway to the innermost reaches of the soul.
If my corset isn't tight, it just isn't right!
Kink is the spice of life!
Come to the Dark Side - we have cookies!
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ponylady
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Re: Humiliating Shopping Dare

Post by ponylady »

well, if mistress needs any more ideas make sure to give me a call.

:mrgreen: :mrgreen: :mrgreen:
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Re: Humiliating Shopping Dare

Post by restricted »

Go into the shops in the mall. Ask the assistant to pick out outfits and lingerie they think would suit you. When you try them on, ask the assistant what she thinks. Spend some time at the makeup counter.
We have ways of making you happily suffer. You WILL enjoy yourself. That's an order.
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bound_jenny
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Re: Humiliating Shopping Dare

Post by bound_jenny »

ponylady wrote:well, if mistress needs any more ideas make sure to give me a call.

:mrgreen: :mrgreen: :mrgreen:
Note to Mistress: call Ponylady for ideas. It's worth the money. :twisted: :twisted: :twisted:

Jenny.
Helplessness is a doorway to the innermost reaches of the soul.
If my corset isn't tight, it just isn't right!
Kink is the spice of life!
Come to the Dark Side - we have cookies!
jdoh
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Re: Humiliating Shopping Dare

Post by jdoh »

She keeps threatening this weekend, but hasn't pushed yet. I'm sure she'd take ideas though. She laughed at the ideas thus far and flashed a devilish grin.
jdoh
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Re: Humiliating Shopping Dare

Post by jdoh »

Well after taking it somewhat easy on me when we tried this originally, it has been brought back up again. My partner instructed me to see if there is any more ideas before she decides on the new instructions. :whip:
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ponylady
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Re: Humiliating Shopping Dare

Post by ponylady »

jdoh wrote:Well after taking it somewhat easy on me when we tried this originally, it has been brought back up again. My partner instructed me to see if there is any more ideas before she decides on the new instructions. :whip:
what ?
you got through all our original suggestions without reporting back and asking for more ?

sounds like 50 lashes with a snake-bullwhip are in order (but jenny is the expert on this topic & will have final say)
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jdoh
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Re: Humiliating Shopping Dare

Post by jdoh »

Yikes, that sounds painful! From the original suggestions She constructed a task that had me purchase a girly white dress with appropriate undergarments in the mall, which I subsequently wore out in public.. We purged those items and haven't explored cd in a while, but She is threatening again...
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bound_jenny
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Re: Humiliating Shopping Dare

Post by bound_jenny »

ponylady wrote:sounds like 50 lashes with a snake-bullwhip are in order (but jenny is the expert on this topic & will have final say)
Sounds good to me! And quite fun. :whip: :twisted:

Jenny.
Helplessness is a doorway to the innermost reaches of the soul.
If my corset isn't tight, it just isn't right!
Kink is the spice of life!
Come to the Dark Side - we have cookies!
jdoh
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Re: Humiliating Shopping Dare

Post by jdoh »

Just to provide a fuller account of the outing from a few months back...

My partner ordered me to go to a mall while on business travel and scope a store that might be appropriate for some guided shopping. I identified a Torrid store, and subsequently received my orders. I was to find a white "girly" dress with appropriate undergarments. I did not have to tell anyone who the purchase was for, unless they asked.

Before entering the store, I decided that cash might be wise for the purchase, so I hit up the ATM down the wing in the mall. With some trepidation, I then entered the store and looked around. A clerk asked if she could assist me, and I indicated that I was looking for a white dress and perhaps some undergarments. She smiled, seemingly knowing who they were for, and asked for a size. I replied and she quickly sized me up, grabbed my hand, and led me to a white lace dress with flared bottom. She insisted that it was perfect for whomever I was purchasing it and said that I simply had to buy it. She then showed me some lace trim panties and matching cami which were pink pastel and would pair well with the dress. She pushed them into my arms before I could hesitate and insisted that they were a "fab" purchase. I quickly paid for everything in cash and returned to my hotel.

Later that evening, I skyped my partner and was guided through dressing and a little self-inflicted punishment. I was then directed to an online chat site to further my humiliation and training.

Upon returning home, I was ordered to purge the items for the next time I was appropriately naughty. Based on a comment the other evening, I fear that time has come.
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