Progressive Panty Buying Challenge for Guys

[FemdomPantyLover]

Guys, this dare will make you publicly purchase and wear panties. Don't worry though, no one may have to know you are wearing them or buying them for yourself, that is if you are lucky!

The Concept

You will buy a new pair of panties each day with a little twist. Each day you will wear the panties out shopping that you bought the previous day.

Day 1: Sizing You Up

Today's task is simple, you are going to buy a pair of panties that will fit you. If you already know your size them congratulations you get to just buy one pair, if you don't know your size then you better buy a few different sizes so that you will know what best fits you. You wouldn't want to make another trip to the store after trying them on at home!

There are a few stipulations to this task, firstly, you must buy them from a large department store as you will use the self checkout to buy your panties. You are allowed to buy up to 5 more items to cover up your purchase. There is no criteria for the panties you buy today, they can be anything you like.

Day 2: Growing Some Balls

Remember you will wear the panties you bought yesterday on your shopping adventure today! You will go to the same store as you did yesterday and quickly pick out any pair of panties you would like. You can pick out any cashier to check out at and buy up to 5 items to disguise your purchase. If the cashier asks you can give them any excuse you would like.

Day 3: Becoming More Feminine

Today wear the panties from yesterday when you go shopping. Today you will spent at least 5 minutes looking through the panty isle. You are looking for a cotton and lace pair that is bright pink. You can use up to 5 items to disguise your purchase. The cut is up to you. You are going to walk back and forth with your items until you pick out the cutest cashier. This is who will check you out. If she asks about the panties you can either tell her it is for you as you love how they feel or that they are a special present for your mom. Either way hope she doesn't ask!

Day 4: Expanding the Search

Today wear the panties you bought yesterday all day long. You will go to a different store today. You need to find a women's store that does not have male clothes but does have panties as well as other normal items of clothing. You will buy yourself a brightly colored thong after spending 30 minutes in the store. This is all you will buy. Most likely there will be a young cute girl checking you out. Lucky you! If she asks about them you will tell her you enjoy wearing them because of how comfortable and freeing they are.

Day 5: This is Embarrassing

Wear your panties from yesterday all day today. You are going to go to a lingerie store and buy you a really nice pair of panties today. If someone asks let them help you pick one out. Be open that they are for you if they ask. If your feeling daring even be fitted for a matching bra. Now you are a true sissy shopper!

[Gaggler]

I think this is a great concept! I've been looking for something like this for ages, that gets progressively more feminine and with increasing interaction with the 'real' world. It's a shame I feel like I should be starting at day 5 though, I hope there are further days and challenges posted!

[FemdomPantyLover]

If you feel like you should start at day 5 then I think you have already advanced past the point of just getting used to buying panties and admitting they are for you. This is the first step to becoming a real sissy and that is what I wanted to portray. I tried to make this fairly realistic and I personally think day 4 and 5 is pushing that. I often buy panties from department stores but only on a day 2 level. I hope to soon be able to work through this list but it will take me longer than a week as it still makes me very nervous.

If you have any ideas for pushing more advanced sissies out of their comfort zone then I would be willing to come up with something similar but more advanced. Maybe the next week will be a bra, then nighties, then full clothing sets, then making it public to get the full transformation...

[rhl]

Want more ideas, lovely sissies?
On Day Six I suggest wearing the Bra and Panties from day Five, and buying a pair of lace pantyhose.
On Day 7 since your such a seasoned sissy wear the pantyhose exposed under shorts, you'll need to shave those legs. Since you now love shopping for girly things you'll buy another pair of Panties and matching padded Bra, you will also try on black leggings to purchase. Girlies love these leggings. I wear them a lot, the reactions are fun to watch.
Day Seven, you'll wear yesterdays outfit you purchased, with a top, the leggings as pants. You need to find a nice female top to go with the outfit you have on.

Day 8, You won't need to buy anything today, you'll wear the top purchased, and the rest of the outfit you had on yesterday. While browsing the girlie department you'll notice a cute skirt. Since your in leggings, there is no reason not to try the skirt on right there by the rack. If there is a mirror you might want to use it. Don't worry I see girls frequently do this.
Enjoy, I have done these myself and did enjoy.
Asca note I've never seen a cashier act unprofessional while buying my sissy outfits.

[FemdomPantyLover]

Thank you for your addition rhl! These definitely bring up the challenging level. I have bought a lot of feminine items of clothing for my mistress and I will agree I have never had a cashier question my purchase and I am sure they just assume that they are not for you. They may laugh at you if later if they notice you are feminized but not to your face. I wish I could trade in all my underwear for panties.

[Kinky Switch]

This would be really hard for me. I might try it though.