r/Sissyβ€’
casrax

Am I hurting myself?

NSFWQuestion

Hey fellow sissies! I just got right to the point. I am a closet sissy and I love anal play in every chance I get. I really enjoy dildoing my ass and I like my sessions to be as long as possible because my please never stops when I fuck my ass. Now I'm sorry for this is going to be disgusting but Whenever I don't have a time limit, I go on and on until I see blood on the towel I put under myself to control the mess. It's usually just a little bit and when I see it I stop immediately. And it won't be a problem until the next time I do the same thing. I was wondering if I'm doing something wrong or am I pushing myself too hard, or if I'm hurting myself. I don't wanna endangere my health and I want to be able to do anal as long as I live. Obviously I use a lot of lube and I don't feel any pain or anything. And when I say long sessions I'm talking about 2 hours plus. So any advice or solutions will be appreciated. 😘😘😘

Posted May 10, 2026, 10:12 PM UTC

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