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I do this to my wife’s pussy with a plug type toy…
Since it and my cock at it’s widest part are quite the stretch, I put it in, and then slide my cock in because it’s easier on her than pushing the thick part of it through her opening with my cock already in there.
But, when she stretches out it fits closely enough for it to slide back out. I love how she feels after that. Her cute little jump when it pops out, and then her stretched out pussy wrapped around my cock afterwards is define…

Cans? Great.  They have that taper near their end so that they stay put, but not such a big taper that they don’t just pop out.  Usually when you’re not expecting it.Pens? Great for their own reasons… You stretch just a little at a time so you don’t really grasp the scale of what you’re doing.  You of course wait till you feel full, very full, but since it’s gradual you’re stretched wider than usual already.  Then, you push yourself, again just like usual, but in little steps… Nudging your limits in smaller steps.  Easier to take steps.  Of course though, you push till you reach a point that is just too challenging to surpass, and you let them all out.  It’s not until that moment that you realize just how much farther than usual you’ve gone, and what exquisite torture you really did just put your poor defeated hole through.
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Cans? Great.  They have that taper near their end so that they stay put, but not such a big taper that they don’t just pop out.  Usually when you’re not expecting it.Pens? Great for their own reasons… You stretch just a little at a time so you don’t really grasp the scale of what you’re doing.  You of course wait till you feel full, very full, but since it’s gradual you’re stretched wider than usual already.  Then, you push yourself, again just like usual, but in little steps… Nudging your limits in smaller steps.  Easier to take steps.  Of course though, you push till you reach a point that is just too challenging to surpass, and you let them all out.  It’s not until that moment that you realize just how much farther than usual you’ve gone, and what exquisite torture you really did just put your poor defeated hole through.
Zoom Info

Cans? Great. They have that taper near their end so that they stay put, but not such a big taper that they don’t just pop out. Usually when you’re not expecting it.
Pens? Great for their own reasons… You stretch just a little at a time so you don’t really grasp the scale of what you’re doing. You of course wait till you feel full, very full, but since it’s gradual you’re stretched wider than usual already. Then, you push yourself, again just like usual, but in little steps… Nudging your limits in smaller steps. Easier to take steps. Of course though, you push till you reach a point that is just too challenging to surpass, and you let them all out. It’s not until that moment that you realize just how much farther than usual you’ve gone, and what exquisite torture you really did just put your poor defeated hole through.

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