Chapter 2: Mysteries - A Sudden End?

I sent Denise an email saying that she could take a break from any tasks the next day, but that she still must refrain from touching herself until I instructed her to do so.

The next day was a Saturday, and I got a very long note from her. Basically, the thing she'd called a complication wasn't such a big deal - but I guess she'd found it embarrassing. She explained that she had been holding a birthday party for her daughter, where some of her daughter's friends came over. It being a Friday, things went late.

I knew that my sister's daughter Melissa had just turned 14, and this confirming detail from my online correspondent was exciting -- but this was the first I'd heard about a daughter from my correspondent. I knew I had to be very careful and not show any knowledge of details of her life that she hadn't yet "revealed" to me in her emails to me -- otherwise she might come to suspect that I wasn't the total stranger she thought I was.

So anyway, she explained that several of her daughter's friends had been over and that once they'd had dinner, one of her daughter's friends asked Denise why she hadn't changed from her "work clothes," (which apparently was her typical habit) and Denise had been at a loss to explain (her words: "to say something to the effect of: oh it's a dare from a stranger on the internet to stay pantiless all day, under a skirt -- seemed a bit too obvious").

That was all. I think she read too much into the girl's question -- like that the girls suspected something. That's what she'd called complications. But I was gratified that she was confiding more in me, and of course it was thrill knowing how awkward my beloved sister might have felt in that situation, even if it was mostly in her head.

So for her next task, I told her to take a long bath or shower (as she preferred) and toy with herself extensively, but again not to let herself cum. Then she was to run at least one errand on Sunday, to a public place, with only a light-colored blouse and skirt, no underwear, bra or panties.

Her note on Sunday night was very fun and erotic to read -- she described in detail how she bathed, "diddled herself," and then shaved all but a "nice little landing strip" on her pussy, leaving the lips "glossy smooth" as she put it. She explained how she'd been so horny that "the moisture glistened in the mirror" before she got dressed. How she put on a nice denim skirt and a lovely emerald-green blouse (exactly her color!), and had gone to run her errand, only to have her daughter (who she called Lissa in her email -- an eerie bit of realism, since that's what I always heard her call her, whenever I'd been around) say something like "hey mom, why're you all dressed up ... oh my god, mom, I can like see thru your blouse." She told how, in embarrassment, she'd had no immediate answer for Lissa, but anyway, she went out to the Target store and pushed a cart around acquiring household goods in a daze, while strange men leered at her, vaguely.

All that.

"Glad to hear you had a fun day," I wrote back, tongue-in-cheek. Then, I told her that her next task was to masturbate for at least 30 minutes the next morning before going to work, but still no cumming. Also, I asked if she owned a dildo or vibrator, and if so, to describe it.

Her reply Monday night was short and a bit desperate: "when do I get to cum? Please!?" I laughed at that. She also explained that her only dildo had disappeared a while back ("must've misplaced it during the long "dry spell" after my husband left," she said; using the word "left" not died, so that one white lie was something she was sticking to, I guess). So no, she didn't have a dildo.

For a task, then, I told her she had to buy a new one on Tuesday, whatever sort she liked, but that it shouldn't be too "modest," and that she needed to use it (only briefly) and describe it in her next note. I told her if she was "good" with this task I would let her cum on Wednesday.

I should note that, just as with instant message conversations, it had occurred to me that the other person might be "faking" some or all of what was going on. I'd known myself to exaggerate or pretend in response to others via IM, and so I had always given the benefit of the doubt to my interlocutors as well. But, I thought, even if she was just writing fiction, this was still so wildly real to me, because it was still so clearly my real sister with whom I was corresponding, and apparently, she had no clue who I was.

Anyway, her note on Tuesday explained how she'd gone to a sex-shop after work, picked out a "rather large, pinkish, life-like" dildo -- "you know, the kind with veins, and shaped right" -- she thought it would be what I had in mind. About 10 inches long, and fairly thick.

She'd taken it home, after enduring the lurid stares of the men in the sex shop, and raced to her room to ram it into her pussy, and now she'd sat down to write me a note. "and I've got it clamped in there right now, while I sit at my laptop typing this, but I'm not moving it around. Can I please USE it?" she added.

I sent back that yes, her next assignment was to use it to bring herself off. But the catch was, it couldn't be at home. She had to pick a place somewhere else (probably a restroom, I speculated) to do it. And she definitely had to finish -- at least 5 full minutes of "pumping" as I put it.

"Wow," she wrote back, the next day. "This is so much exactly what I was hoping for, when I decided to take a chance and write to you. I LOVE what you're making me do."

She went on to describe how she smuggled the dildo into work in her purse, and, getting there a half hour early, with the place largely deserted, she got into a stall in the restroom and "fucked myself silly." A wonderful image, I thought. She explained how she soaked the toilet seat, and had to put on fresh panties (which she'd had the forethought to bring with her -- always well-organized, that's my sister Denise!).