Desperate for a number of dares

[John66557]

So I've been doing the odd cross dressing and bondage, I'm always looking to up the ante and take on multiple challenges over the coming weeks, this is your chance to put me to the test


Things I like

The idea of cross dressing in the woods having the nerve to be on main paths
The idea of a full shopping trip
The idea of toys
The idea of helplessness
The idea of sissyfying
The idea of going out driving
The idea of outdoor bondage



Things I have

6 pairs of knickers
Multiple matching bras
2x leather skirts
A bad pair of fitting heels (my partners which are 5 sizes too small, generally cable tie these on)

Things I don't have

Toys
Dresses
Wigs
Make up
The nerve unless encouraged
And lots of other things

If you'd like me to report back I sure will and if you'd like photos I would certainly consider it, just tell me what photos, always need the evidence. What times of the day and what days are best for the dares ?

So go ahead don't hold back and see what you can do

[Hannah_G]

Ok, so looking at what you like and what you have, it’s obvious you need to go on a shopping trip. The aim of this is to get everything you need to go out in public crossdressed. You don’t need to wear any woman’s clothing on this first trip as you’ll be going out dressed later.

The key thing is to be sure that you don’t disguise the fact you are shopping for yourself. If any of the shop assistants ask if you need a gift receipt you say “no thank you”, if they ask if it’s for a gift you say “no”. If you’re not sure about which products to buy, you’ll need to ask for help.

First you need make up. Primer, coverage foundation, concealer, setting powder to cover beard shadow. A small eye shadow palette, mascara and a subtle lipstick.

You’ll also need a wig. Amazon might be best for this unless there’s a store in your town.

You are sorted for knickers and bra’s, but I’d suggest a pair of support tights to help hold the bulge.

As for clothes, you need to blend in rather than stand out. I suggest you look for a pleated midi-skirt and contrasting top. Pleats are also good for disguising a bulge, especially if there’s a pattern. Finally you’ll need some shoes. I’d suggest some flats and if you’ve big feet, then online again might be your best bet.

Now you’re ready for part 2. You need to do your make-up, stuff your bra and get dressed. You’ll then go to the local hardware store and buy the following:

10m of rope
A length of chain
2 padlocks
A roll of parcel tape
A roll of black pallet wrap
Bin liners

I’m sure someone else will be along to now tell you what to do with the stuff from the hardware store

[kinbaku]

I’m sure someone else will be along to now tell you what to do with the stuff from the hardware store

Get ready with the things you bought.
Go to a wood with the rope, chain and two open padlocks at each end of the chain in a handbag. The keys to these padlocks remain in the car.

Once you have covered a sufficient distance (at least 2 km or 1.24 miles), seclude yourself and tie the rope around your legs just above the knees. you block that with the chain that you turn around the rope as a cinch between your legs. Then you can connect the 2 locks at the ends of the chain.

Now try to walk back to the car and stay on the path. Remember that you need time to move away from the road in narrow, noisy steps as you need it.

Once in the car you can release any padlock and that will release the chain and then you can remove the rope before driving back home.

PS: If you are not afraid of electricity, I advise you to purchase a DG-Lab Coyote. You can then make the above even more spicy without people hearing a strange sound from a possible hidden vibrator.

[John66557]

1 dare received and Its time for me to take a breath and comit, this will be taking place middle of next week

[John66557]

I also like the thought of heels rather than flats as well as a mini skirt instead of midi, would you like me to add suspenders ?

All this is up to you at the end of the day

[Hannah_G]

No. You should wear a midi-skirt and flats. You can add suspenders if you like, but if you want to be out in public crossdressed, blending in is the better option. You don’t see many women out shopping in mini-skirts and heels

(Trust me, I’ve done this before)

[Hannah_G]

So, we’re at the middle of the week! Any update?

[John66557]

Sorry for the delayed response it hasn't been letting me post .... but hopefully your ready for this one !