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[anal sex] My girlfriend is way too tight for anal but she keeps making me try it with her.(r/sex)
Okay, if your GF really wants this, I suggest you looking into an anal dilator kit for her. The way you’re describing a “little buttplug” sounds like it’s not doing anymore her in terms of stretching her inner sphincter muscle. Try getting a set like this and use them with her or have her do them beforehand herself, tell her to go up to the one that’s actually a little thicker than you are in order for maximum comfort for when you finally do have anal sex.