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He could feel his finger glide easily into the small entrance. Stepping back slightly he reached for the gel and poured a generous glob just at the top of her ass crack. Ross gently massaged the slime between her crack, paying a lot of attention to her bum hole, teasing it with slippery fingers, gently trying to probe past the closed puckered ring without exerting any real force, before travelling further under towards the virgin cunt. Cathy was trying to relax, the soapy hands of her brother felt good as they treated her to the sensuous massage, but the thought of what was to come prevented her from fully loosening up. She had hoped that he would continue to massage her sensitive breasts longer than he did, and when he teased her anal ring she almost wanted to shove back onto the finger and feel it enter that most dirty of places. She was disappointed when she felt his fingers leave her rear passage. She closed her eyes once more, enjoying the feel of the soapy finger that was now. Well, if you'd like to 'test' me, I'll be happy to submit to it."I watched her and she realized that she had, in effect, offered herself to me -- at least in some way. It was her turn to be flustered. "Why don't you go out with any girls, then?" I have been out a few times. But, well... it's just that..." I was choking up the way I always did when a cute girl had me on a spot - or even talked to me at all. I looked out my side window trying to work up the courage to admit I'm so damned shy. It was stupid, I know, but I just was too shy to admit I was too shy. I wanted to be thought of as 'cool', or at least normal. I couldn't help it when the tears began to well up in my eyes.Terry put her hand on my arm. I turned back to her and she saw my eyes shining in the dim light. "Oh, Denny, I'm sorry! I didn't mean to pry. If it's some problem you can't talk about... oh, never mind. It's none of my business anyway." I sat there trembling with shame as she gently wiped my tears. I've never.
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