Fisting

B_Think_Kink

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It shouldn't hurt at all if done right TK, a little discomfort as you get into it (or should that be "as they get into it"?) and maybe a little after, but hurting shouldn't be part of the equation.

Well kept, short nails are the most important thing to remember (unless using gloves) and not to push things, a little at a time, wait until its comfortable, then stick with moving around without going further until you're completely at ease with it, and go a little further.

If you reach a point where you physically feel you can't have any more in, but want to stretch for that little bit extra, wait until orgasm, and as you start, then go for it.

Thats how it worked for me anyway
Thanks, he can get 4 fingers in laying side by side, so he wants to try and put it all in. I was kind of like.. omg I'm loose... but he said it doesn't feel loose when I fuck him, so that was good to hear.
 

Deno

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I often wished I had someone to do this with. Good luck. Take your time. Before he puts his entire fist in there he should work at a few other fingers from his other hand. If you can take all 4 fingers from both hands then I let him start with the fist.
 

B_Think_Kink

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I often wished I had someone to do this with. Good luck. Take your time. Before he puts his entire fist in there he should work at a few other fingers from his other hand. If you can take all 4 fingers from both hands then I let him start with the fist.

Don't worry he's not that stupid to just try and stick it all in there.