Tasks for Crossdresser

[lotus]

Hi there all - I need some help -
I am helping "bring out" a shy crossdresser online who I met through IC.

So far they have dressed up in stockings, suspenders in a variety of naughty poses and had to mail me proof.

Now looking to move this on an desperate for some ideas - what would you find challenging / sexy ? Is it moving it into new areas (out of the house) or first new dressing ideas.

Any help appreciated,

lotusxxx

[restricted]

A photograph of him outdoors while dressed? A picture of a receipt for make up he bought for himself?

[stephen]

Here is an idea. You buy him a compination lock and mail it to him keeping the code to yourself. Have him either pack a bag with an outfit and makeup minus a piece of makeup say foundation. Or he can buy everything as he does this. ill give buyin first. If buying he takes a purse and goes to the mall to start. Go to a couple stores and buy clothes to make his outfit for the rest of this deal. for more fun have him buy a sexy top or skirt that is to small for him so he has to return it. I did this. After he has everything but the foundation have him to to the restroom and put on the panties, panty hose, and bra and depending on what he bought to small the bottoms...juniors stress cut jeans work great for this hint hint hint. now he has to go back and return the top for the right size one.

Have him leave and go to a store that he can get help with buying some foundation. take his purse with the top and make up he has inside to the restroom and get change into it all....now have him take a pic of himself and send it to you and a pic of the bag with the lock you mailed him locked on it....he now has no choice but to leave dressed up...tell him you want pics of him at the make up area going throough foundation if he does this and buys the foundation you will give him the code for the lock when he gets to the car....

Now if he is to new to this doing all of this will be hard. so skip to the second part one store dressed up all of his man clothes minus wallet locked in the bag. this way he can run on the though of things for a second before he gets the idea of backing out. once everything is locked in the bag you have no choice but to walk out...

[Jarjarv31]

Love this idea wish someone would do this to me

[bound cindy]

I would love it if he would meet me in a city centre, we can be dressed in our guy clothes, go shopping for various female clothes, wigs and makeup. that you order him to get. we can go to a female toilet, get changed and do each others makeup and then go for a walk thorough town. we could video the whole day and then you can have it to keep

[wayneheidlebaugh]

Here's an idea;
Send him a small package by mail with a pink combination lock, (opened only you have the code)
Also include insruction for him to get a pink skirt with belt loops that will fit him and a chain to
be used as a belt. The instuctions should also state that he must put the skirt on, thread the chain
through the belt loops, pull it tight around the waist and lock it with the combination lock. If he is to
be freed from the skirt, he must send a picture of himself wth the skirt locked on him, then you can
send him the lock's code so he can finally free himself from the skirt.