Some good ideas, let's see here...<br/><br/>Yeah, having pleasure checks at Con intervals makes sense; I was still kind of in the mindset that they do pleasure instead of damage, but if they're doing both I don't need to shoehorn in a way to include healing/max HP in the pleasure mechanic.  I think for resting, every round the victim's pleasure drops to their next threshold, or if it's already at a threshold, it drops to the next lowest one.  (So a character with Con of 12 and current Pleasure of 28 would drop down to 24 Pleasure after one round, then 12, then finally 0).  In addition to other penalties however, all d20 rolls are made at a cumulative -1 penalty for each threshold passed.  So, said character would be at a -2 penalty while her pleasure was at 24 or higher, then drop to a -1 penalty at 12 pleasure, and finally no penalty at 0.  This would replace the mechanic for having increasingly difficult saves to avoid orgasm/fatigue as well.  (Might be a -2 penalty per threshold, depending on how quickly girls gain pleasure.)<br/><br/>I am going to say that a monster can't make multiple grapple checks on the same target in a round.  The first check is just to grapple the target, the second pins and also lets the monster either strip armor or rape, depending on if she's naked yet or not.  I want armor's AC to be included in how difficult it is to strip her (while the bebilith's ability is nice, it doesn't care about what type of armor it is at all), so I think monsters just have an armor damage statistic.  This also lets me have other ways of stripping a character's armor (for instance, the succubi earlier had a "Remove Armor" spell that did armor damage).<br/><br/>On to characters getting free.  Since it takes two turns for a monster to start raping someone (one to grapple, then a second to pin), I think it's only fair if characters have to make two checks to escape as well.  Escaping from a grapple while pinned only reduces you to being grappled, not being free; similarly, a failed maintain check or a successful sunder tentacle attempt don't completely free someone that's pinned.  (This only applies to tentacle monsters, with the assumption that since they have so many tentacles, it takes more time to get free from all of them - other monsters that grapple and pin work normally).  This does still give a slight advantage to the heroes, since they can "focus" and have multiple characters working together to free one.  The actual escape attempt by the victim will be much easier, in this case, though if you're pinned getting free on your own will be much more difficult.  Also, a successful sunder automatically frees the victim if she's grappled/moves her to grappled if she's pinned, since there's already a check made to actually hit the thing.