It shouldn't hurt unless your asshole doesn't agree with your mind, and it tightens up. If it hurts, stop. Let the pain pass and try again more slowly... Whatever you do, don't force it. The trick is to really relax. Feel the muscle relax. You have to FEEL it. And then, if you are having trouble, try pushing down like you are doing a number two. Remember to lube the toy and your ass, okay? Oh, and make sure your bowels are empty, and watch for cross-contamination. And lastly, wash and pee after. “I need you to tell me Jill. Are you?”She let go of his cock and held her hands in front of her, looking up at Tom, almost sad. “Beck and I are such good friends, about a year ago, for some reason I began to have fantasies about her. Things we could do together ... as more than friends. I began seeing her in a new way. One time after that, mom had me cleaning out the attic when I came across a box of my dad’s. In the bottom was a magazine ... one about ... lesbians. I hide it in my room till. More

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