Came across this forum a few days ago (looking for something else) and noticed my software mentioned a few times so I thought I'd say hello and shamelessly promote it a bit.
It's an open source application i.e. it's free and the source code is available to anyone who wants to modify it or just have a peek. I'm a hobbyist programmer, I taught myself Visual C# to write this and it probably shows in the code
The application allows you to specify a number of categories i.e. cuffs, plugs, boots, etc and then populate those categories with items. A random set of categories will be selected then a random item from each selected category will be given.
The driving principle behind the development has been to make it as user customisable as possible i.e. you can define any category you like, any item you like, change the background image, move the checkboxes about, etc.
You can modify the probability settings in many different fashions i.e.
What percentage of your total categories will be selected for each session type
Make various categories more or less likely to be chosen (I like boots, that category is always at 95%
)Make various items in each category more or less likely to be chosen
The second part of the program is a random trigger. This runs on your PC as a system tray application (both components are Windows only, I've looked at porting to Mac & Linux but it's beyond my skill-set at the moment) and kicks off a random session on a random basis (there's a "random" theme here!). You can configure how often on average and the probability of different session types. My personal settings average out at once per month with 50% change of a full scenario, 10% for a light session (25% change of any given category being selected), 30% for a medium session (50% chance per category) and 10% for a heavy session (75% chance per category).
Sorry if that description is a bit number heavy, hopefully it makes more sense when you see it in action. You can define additional parameters for the random trigger i.e. only trigger between certain periods (after the kids have gone to bed in my case) and password protect the whole thing so a screen with a full list of your sex toys doesn't pop up when someone's borrowed your laptop.
The application isn't self-bondage specific, I actually wrote it for my partner to use. She's not particularly into fetish or bondage but willingly indulges me, occasionally. This app was written to introduce an element of surprise for me rather than having to dictate when and what every time.
As I'm not into self-bondage there are probably features missing that would make it more useful for people who are. The application is still in development so if there's anything you're after, let me know and I'll see what I can do. There are a number of posts over on the bound forum that discuss the development that's taken place so far and what suggestions have already been incorporated.
http://www.boundforum.com/forum/forum_p ... p?TID=9241 & http://www.boundforum.com/forum/forum_p ... ?TID=10914
I've included a screenshot of the default main screen below, if you're after any more information head on over to http://randomdresser.sourceforge.net
Thanks
Crowley
It caused me some pain (we do pain) as to if or if not to release 'Bluelist'. I was very concerned about a clash of interests. Back a year ago or so when I was playing with 'Randomdresser' I had a lot of stability with the befuddling patches on patches of MS upgrades breaking it. After defecting to Linux I never could get it run under wine. Thus 'Bluelist' was born, it took on a life of its own from there. 
, I'd gotten so used to looking at the images during development that the program just didn't look right without them.
what an image!