You have a roommate, so I assume he sees her on a frequent basis. Do you feel "strange" when your roommate and boyfriend are in the same room together now? Ditto for the friends. Have your relationships with your friends changed because of this?
Have you told your roommate and friends about this? If so, how did they react? How do you act around these people now, knowing that your boyfriend not only has pictures of them, but uses their pictures to fuel his masturbation fantasies? If it's making you feel uncomfortable around your friends (and him), then that needs to be explained to him (again). It's a relationship, should be built on trust, comfort, understanding, compromise, etc. I think it's time he compromises, respects your feelings about this, gets rid of the photos, and finds some new (preferably unknown to both of you) subjects to store on his computer.
I think he transgressed the bounds of a relationship. It's one thing to have private (or even shared) fantasies about friends or other people close to us, but it sounds like he's being an opportunist when he decides to make these fantasies into stored images. He wouldn't have met these people, except through you, so taking photos of them (you didn't say how he got the photos) to add to his permanent collection for his secret masturbation purposes doesn't sound that good - at all. This isn't fantasy at all - fantasy would connote impermanence; the fact that he can constantly return to stored images does not spell impermanence to me. I bet you're going to be extra sensitive next time you see him shooting pics of your friends at a party.
He wasn't being too open and honest about this activity in the first place; otherwise, he would have told you up front. His reaction when you asked about the pictures says quite a bit -- he acted guilty. If these are your standards, then you live by them and do not adjust them to accommodate someone else who, quite frankly, may not be around for a significant period of your life. Sounds like he's got some maturing to do in regards to relationships and friendships, how they should work, and how to maintain them.
Just my 2 cents.
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it's gritty
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