To make a long story short, about a year ago we had a conversation about masturbation; I explained it to him and said I did it and there is nothing wrong with it. He claimed he did not do it. But I walked in one night to turn off his TV, and he had fallen asleep with his boxers wide open and his penis in his hand. I covered him up, and the next day I talked to him about it. He insisted he does not masturbate. I let it go but told him to be careful, because he did not want his mom walking in on him like that. This has since happened twice more. I asked him again, joshing with him about his habit, and he got really defensive again, saying, "I don't like being accused of something." How do I handle this? Should I just drop it? I know at that age it's hard to admit to something like that, but I've tried to instill a healthy outlook on the subject and was hoping he'd be a bit more relaxed about it. What am I doing wrong?
Don't blame yourself so much. As much as you've tried to develop healthy attitudes about masturbation in your stepson – and for that I applaud you – his perception of masturbation has probably been shaped by his peer group. As you probably know, among certain groups in junior high school, it's popular to use masturbation as a put-down. People call each other masturbation-related names and imply that masturbation is only for losers, gay people, etc. This of course is their way of dealing with their own masturbation habits (denial). Some of this has probably affected him, so no matter what you say he still feels guilty about masturbating.
At this point you've probably done about all you can do, although it never hurts to continue subtly supporting the idea that it's all right. You could try to have a heavier conversation with him, where you try to find out the root of his guilty feelings – but that might not work too well, as he seems already to be sensitive about his privacy. It might be a good idea to tell him he's old enough that you or his mother won't come into his room anymore without knocking, because you respect his privacy, as he should respect yours. Also by way of gentle reassuring you could leave him lube or tissues or anything else you might feel is appropriate and needed, although use your judgment to determine if that might be going too far.
My guess is with time, as he matures emotionally, he'll relax a bit and start joking about masturbation. Until then, be proud you've handled the matter in a mature, progressive manner – you're helping a lot more than you know.
Do you find yourself masturbating more often during some seasons than others? Why?
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