I'm not a great fan of roleplaying via IM, especially with strangers. I find it a little pressured and limiting in the way I can describe the situation, the background and what I am doing. I find I don't have time to sit and think about what is happening and what I would like to do, I always end up on the old standby of thrust thrust, grope grope...
In fact I will not run straight into IM roleplay with someone I have just started talking to, I would rather spend sometime on the sites getting to know them first, their likes, dislikes, extreme turn-offs, its better to know before going in then finding out midflow that she hates having her nipples pinched or her breasts mauled
As for asking for pics, I have done that, mainly with a 'female' IM'er who has just popped up on screen, its a great way of getting rid of them if they won't take go away as an answer. The last time was with a pair of french women who supposedly got my IM from here. I was a little wary when the first one asked if I had really raped someone, then went on to describe a fantasy she had about being raped by 15 year old boys and how this had once happen. Then a little while later her older, married friend appeared, I got a little wary, warning bells started to blare in my head about this being some kind of setup, so I sent her message that I would only carry on playing if they posted a pic each where they where all they were holding was a card with 'PerviPete this is for you'. Didn't hear from them again. Not sure how sad I am about it, but shrug.
Oh, BTW, Hi how are you, any chance of a pic blah blah
