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It is so easy to use sex as an anti-depressant, without thinking of the consequences. This is one case that backs up my plea to girls to keep their body count down. I get quite a bit of criticism for that. People say it should not matter. Sorry, but it very often does.
What can you do? Probably not a lot. He has limits set in his mind, and you have gone past those limits. What makes it worse is that these two were friends of this guy.
Best bet, if you can, is just to keep in touch with him. See how it goes. Give him a bit of time.