Yes...sissies should be tucked well.
You might want to start putting him in girdles Madame.
One size smaller than his natural waist size.
This will act as both a gaff...as well as a sort of chastity device to
keep him from playing with himself. Especially one that has a high waist and very firm.
Just make sure the material isn't too flimsy..it should be a thick weave.
The tight material will hold his tiny cock back in placeand will not move.
even better if the girdle has zippers and bones.
I recommend....
http://www.frish.com/index.php3?SCREEN=department&department=722
Also...it will remind himto watch his figure and he will feel what many women have had to
go through for years.
As far as image editing software ....i'msure there is freeware available with
a simple search in google.
i use photoshop to resize.
If you have to convert...you might also need a tiff/gif/jpg/etc. converter.
Hope this helps.
Sissy cuck maid.