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Heya Stealth Man,
I think that was the case for me as well. It was also when the Stealth I had was new, too, so I am pretty sure it hadn’t relaxed into fit yet, as well. I recently ordered a new one, so we’ll see what happens with that one. I’ve also taken to wearing a metal glans ring to help with turtling.
What I do is put on my longest skin sleeve, and then put a glans ring on over that, just behind the head of the penis (make sure you use the right size, guys, in case of erections.) After that I put on the Stealth, then a retainer band over the metal glans ring, it adds a little padding in case the stealth hits something. After that I’ll add one of the black jackets, and then also another skin layer. Once those are on, I’ll add another retainer ring over where the glans ring is, then fold them all down the shaft, and smooth it all out, then add a final retainer ring at the base of the penis over the end of the sleeves to keep it all in place, and to encourage a bit of penile engorgement. Overall it’s very comfortable, and it doesn’t slip off. It also adds some nice thickness, and holds its form really well, with the additional skin layers, and jacket.
I’m interested in trying out the Corkscrew, but at this point, I’m not sure I want to spend the $50 on it quite yet.
Anyhoo, hope this helps 🙂