Humiliating Shopping Dare

Post your dares or request a dare here.
jdoh
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Humiliating Shopping Dare

Post by jdoh »

In addition to the punishment dare request below, my partner is intrigued by the idea of humiliating shopping dares. She is toying with the idea of sending me out for women's clothes and bondage gear, but wanted me to see if the forum could provide details or suggest an alternate assignment. Any input would be appreciated.
RADER123
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Re: Humiliating Shopping Dare

Post by RADER123 »

Make him wear a full fem dress, with wig, pantie-hose, high heals, make-up,
the works.
Than have him wear his coat thrown over his shoulders with out putting his arms
in the sleeves; hand cuff him behind his back, drop him off at a mall,
then drive round to the opposite side of the mall, and he must walk all the way
through the mall to get picked up.
It should be fun. :idea: :lol:
Rader
jdoh
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Re: Humiliating Shopping Dare

Post by jdoh »

Thanks for the idea Rader. At this time I only have panties, my partner wants me to acquire the rest through shopping. Suggestions on how that should go. I'm sure I'll be asked to perform your idea afterwards.
BornThisWay
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Re: Humiliating Shopping Dare

Post by BornThisWay »

Assuming you do your shopping at the mall....
You can go into one of the stores.
You could request to try the clothes on in the dressing room.
If they deny you that because your a man, you can pay for them and then go to the dressing room to put them on.
After they are paid for and your wearing them, walk strait out of the store quickly as if you had just done something wrong and stop for 5 minutes right outside their store.

If security comes to see if you shoplifted them, you can show him the receipt.
If no one shows after 5 minutes standing outside the store, you can go to the next store in the mall and purchase the next item on your partners list.
jdoh
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Re: Humiliating Shopping Dare

Post by jdoh »

Very devious :oops:

Suggestions on purchases or other assignments to pass along to my wife?
jdoh
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Re: Humiliating Shopping Dare

Post by jdoh »

Any additional ideas? I have been ordered to purchase an entire outfit and accompanying lingerie with which I can pass as a woman.
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AssTechWarrior
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Re: Humiliating Shopping Dare

Post by AssTechWarrior »

For a man
Required:
Tightest pair of womens or girls pants you can fit into. 32" waist can probably get into a girls 4 or smaller stretch jeans.
A girls top, once again, as tight as you can pull over your body.
A buttplug, the largest semi-comfortable size you can manage.
Rope
Cockring
Pink socks and slippers or keds type of shoes ( or heels if you want to go all out )
a supermarket.
20 one dollar bills, folded in half lengthwise

Tie a karada or other style rope bondage onto your naked body. Add the cock ring. Lube and insert the butt plug then get dressed. Put the money ( folded singles ) in your sock
Go to the supermarket. Park at the far end of the row.
When you get inside, ask a female clerk where the cucumbers are.
Do not get a cart or basket, carry everything in your hands.
walk towards the middle of the store and find where the lard is or crisco. Pick a small size package.
Go to the pharmacy area and select a single fleet enema.
Go to produce and inspect the bananas, then every other dick shaped item in the section.
When someone is in the area near you pick up a pineapple and stare at it for a minute or 2.
Select a bunch of the largest bananas you can find.
Then go find the largest cucumber they have. No bags for the produce, carry them.
you should now have 4 items. Go to the dairy section and get a can of spray whipped cream.
Go to the checkout counter. Chose the one with the youngest female working.
When you have the total, bend at the waist to get the money out of your sock.
You don't need a bag, you can carry it out like this.

If you aren't bright red by now I don't know what will get you...

If you really want to be daring, before the buttplug insert a few glycerine suppositories.
jdoh
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Re: Humiliating Shopping Dare

Post by jdoh »

Gulp, thank you for the idea. I am indeed a male sub, so I will have to try this. Certainly a challenging assignment. Since I haven't yet acquired a full female outfit, a recommendation on acquiring those first?
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AssTechWarrior
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Re: Humiliating Shopping Dare

Post by AssTechWarrior »

Go to a thrift store where donated clothes are sold. Usually quite cheap, one around here has $1 days where every item is a buck.

For pants, as I said before, if you are a 31-32 waist you should fit in size 4r girls stretch jeans. They come on light colors and will be tight on you.

If you are bigger take your measurement around your waist and around the biggest part of your thighs. Divide both by 2 and remeber them. Bring something with you to measure when you shop. if the waist, when buttoned and stretched is 1/2 your waist it is probably close. Same with stretch wide the leg on the thigh and if it gets to 1/2 your leg size they can fit.

Buy several if you can spare the few dollars. Womens clothes tend to be stretchy, make sure what you buy is so you can get it pulled on. It takes some fighting for me to put on a pair of 4r pants but they are painted on tight.

Buy tights, yoga pants, etc. I like the light colors as they show off more.
Boundryan
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Re: Humiliating Shopping Dare

Post by Boundryan »

Here's something that I think I'm gonna try to do. I'm not to good with walking in heels yet so I'm gonna wear my girlfriends ugg boot. Luckily we are the same size. With a pair of super tight leggings and with either a bright color thong or string bikini. Haven't picked out a top yet and I was thinking of wearing a girls hat with make up. Then walk around the mall to buy random girly things. By me we have a store call Spencer's that sell vibrators, butt plugs and light bondage gear. So a vibrator would def be on the list. Maybe even get a Chinese massage in the middle of the mall. Hope my underwear won't be on display.
jdoh
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Re: Humiliating Shopping Dare

Post by jdoh »

Thanks for the ideas all. I'll start checking these off in the coming weeks. Any thoughts on diaper shopping dares as well?
jdoh
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Re: Humiliating Shopping Dare

Post by jdoh »

So I've been told I should purchase two outfits this weekend, something secretarial and something flirty, with matching undergarments. Thoughts on what I should buy and how I should do it?
boundsharu
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Re: Humiliating Shopping Dare

Post by boundsharu »

jdoh wrote:So I've been told I should purchase two outfits this weekend, something secretarial and something flirty, with matching undergarments. Thoughts on what I should buy and how I should do it?
Put on matching female outfit with a wig and makeup.....
Heels are must.......
And go to shopping.....
Buy formal shirt (blue and white. Or any you like)...... and female trousers...... with a tie.......
Slutty outfit..... I suggest you go for latex.....
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ponylady
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Re: Humiliating Shopping Dare

Post by ponylady »

for the secretary look a frilly blouse with a knee length pencilskirt is a must.
if you are daring, colormatch highheeled kneehigh boots with the blouse.

about the flirty outfit:
where are you going to flirt ?
@ the pooltable in a dark, seedy bikers bar or @ intermission in the opera lounge ?
[
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bound_jenny
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Re: Humiliating Shopping Dare

Post by bound_jenny »

ponylady wrote:for the secretary look a frilly blouse with a knee length pencilskirt is a must.
if you are daring, colormatch highheeled kneehigh boots with the blouse.
That is definitely what I have in mind.
ponylady wrote: @ intermission in the opera lounge ?
I can imagine the sound monocles dropping into the drinks... :rofl:

But seriously, here, a lovely ball gown with plenty of cleavage, opera gloves, and a tiara (you don't want to look too slutty, just rich slutty :mrgreen: ).

For the biker bar, take the tiara off. :P :P :P

Jenny.
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If my corset isn't tight, it just isn't right!
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