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Spying son/brother gets a surprise or two.

Facing me. That's good. Now pull out my cock." Even the touch of Jane's hands on my zipper was nearly enough to send me over the edge - it had been a long few hours. And it was the most exquisite release as she sprung me free just inches from her nervous face. "Okay Jane, for our first time you're going to bring me off over your face. Later on I'm going to fuck you in each of your holes, but for now we're taking it simple."

Jane reached up, without even being asked, and began stroking her fingers around the shaft of my cock. Her grip was a little hesitant at first, but that almost increased the delicacy. "Tell me what we're going to do later Jane."

"You're going to fuck each of my holes."

"Tell me about what I'm going to do to your virgin ass Jane."

"You're going to fuck it."

"Say everything properly, Jane."

"You're going to fuck my virgin ass."

"Am I going to come inside your tight virgin asshole Jane?"

"If you want to."

"Then say it."

"You can come inside my tight virgin asshole if you want to, Mike." The look on Jane's face was positively coquettish as she said this, and it was all too much as I boiled over, shooting thick white gobbets of sperm onto her face, Jane still stroking carefully and slowly, obediently keeping her face in position as I shot my come all over her.

I flopped back, briefly totally spent. But the sight of Jane - my friend Jane - still kneeling dutifully between my legs, her face spattered with my come and her nipples poking out even more stiffly, started an almost immediate reaction in my cock. I looked at my watch. "Six days, twenty three hours and thirty minutes to go." Would you believe it, she almost smiled?


In fact I didn't take Jane's anal cherry that evening. It seemed far more piquant to allow her to anticipate it for a while, and so I told her that she would be ass-fucked the following evening.

All through that next day I sent her e-mails, reminding her what was going to happen, forcing her to describe in ever more detail and using ever filthier words to tell me what would be done that evening. It was tempting to get her to start doing things to herself while at work, but reminded myself that drawing things out would be more fun.

Once again I beat Jane to her apartment, and although once again she was walking quickly as she walked around the corner, I thought this time maybe the motivation was excitement, not fear.

For just a few minutes upstairs the same "being face-to-face" awkwardness surfaced, but then Jane fetched us some Chablis and we seemed to fit back into the previous night's roles.

I told her to strip, kneel on all fours on the bed, and pull her ass cheeks apart for me. I spent a little time pointedly and carefully inspecting her ass, knowing that such an intimate exposure would be embarrassing and maybe exciting for her.

Maybe for some people in my position and with my control over Jane the obvious thing would have been to simple fuck her ass straight away, driving hard into her tender hole regardless. But I was far more interested in cold hard Jane discovering that she loved to be ass-fucked, just like she'd found - so I believed - that she got turned on being subjugated to my will. Far more exciting for me to see coming and coming from the sordid pleasures of ass-fucking than the simple buzz of her face contorted with pain. And the pain would happen anyway, I knew that.

I told Jane to ask me to lick her asshole. Starting cold, so as to speak, she struggled to begin with but soon managed the request. She actually gasped as she felt my tongue press against her hole, and quickly she was pushing herself back against me, loving the firm wet sensation as I probed her sphincter.

"Feels good, huh?" I asked, momentarily pulling away, and her nodded response persuaded me to try a little diversion from the main task at hand. "Lick my asshole then Jane." She rolled over onto her side, looking at me warily. She hadn't expected that.

I lay back on the bed, lifting my knees up to my chest, exposing my asshole to her.

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