Hey all, I’ve recently begun my journey to twink/sissydom and had a few questions about insertion. I love the idea of being penetrated, but I’m having trouble putting fantasy into action. I purchased a small prostate massager, but I can’t get it very far in. I use lube, but it’s still tight going in, and I feel like I hit a “wall” that I can’t get past. Pushing up against it just makes my intestines sore. Afterward I just feel a dull pain in my lower back and mental satisfaction.
It hurts and I don’t know what I’m doing, but it feels so right I just can’t stop. Any tips from other, more experienced sissies?
You’ve taken the first step, which is great! Anal can be tricky, but it is very fun.
See if you can use your breath to control your ass muscles. Breathe deeply, from your stomach, not your upper chest; your shoulders shouldn’t move when you do this. While you’re breathing deeply, see if you can contract your ass muscles when you breathe in, and relax when you breathe out. Once you’ve got the hang of this try siding a finger or small toy up there while you do it. Let us know how it goes!
And remember, if it doesn’t have a base, it can go up without a trace…