I'll try keep this short as possible. In reference to a thread a while back there was a consensus that it would not work to say promote other sites due to the impulsive nature.
A while back I started
http://www.adultgroupdeals.com - and gave up on it as the more I thought about the project + I got busy with my mainstream shit, the more it wouldn't work. I also spoke to a few of the bigger guys who were scared of the concept and that it can 'devalue their brand' - which is a reasonable point enough - I guess after tubes ruining the industry, people are kinda sensitive.
Anyway the neagtives I noted were:
- Impulsive buys - people want pron now
- De-valuing
- The chargeback issue (who takes that on the chin)
- The social media viral know how won't be as affective as say groupon - eg. Not many people wanna share their fetish of 'midget bdsm' to everyone on facebook or twitter.
ANYWAY - the reason I have responsed to this thread is that the only avenue I could possibly see is perhaps for content being sold to webmasters.
So perhaps and this is only off the top of my head
- A discount of XX% to 10 people who buy these ex gf photo sets
- Perhaps to even book a girl for a photo shoot where people get X amount of photos of their choice
So I guess more of an 'activation' type concept.
Would like to hear anyone's opinion on this and even those who are interested in trying to get something like this started feel free to ICQ me

I've done the site and spent a bit of money on it & it is just sitting there in Limbo :p hahaha
Also - exoticdeals.com are doing this with places like strip joints, sex toys - which I can see that will work. Just building the marketing platform to get people always coming back will be interesting. It's a great designed site - will be interesting to see how it kicks off, however it seems to be stale within the last few months.