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WARNING: This story may depict sexual activity of fictional beings, solo, or between men and women, or women and women, or men and men, of various ages, which may be above, or below, the age of consent, in one or another real-world polity. Or something like that. If that freaks you out, or violates some law that applies to you or your computer, please don't read it.
Wow Thanks (MFf, exhib, voy, inc, cons)
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 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 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!).
I told her I was very impressed. I was. "So," I asked, "are you ready to flash someone? If so, who would you flash?" I wanted to give her a chance to provide some input, hopefully thus keep her from feeling she was too far out of control, I guess. Meanwhile, I told her that her task the next day was to wear a skirt, pantiless, again, and think about flashing a guy (or woman, if she wanted) up her skirt, and who it would be.
She wrote back that she felt it would be better to flash a stranger than someone, say, at work. Maybe someone at a place where she often went to have lunch, a sort of downtown mall food-court, near her work. She said she nearly went ahead and did it, that day at lunch, at a good looking busboy who was there. "I aimed, but didn't fire," as she humorously put it.
So, I sent back: "Go for it - I think someone at your lunch spot is a perfect idea. Your task is to flash him a good view of your crotch, with white lacy panties, for at least 10 seconds."
She completed this task, and a few escalations of this same one, over the next several days and through the weekend. On Sunday, I had her go shopping for shoes, with instructions to do the classic expose-yourself-to-the-shoestore-clerk. Though, in keeping with my commitment to gradualism, I let her do this with panties. Then on Monday, the dare was to masturbate that morning, no cumming, and to flash a guy at lunch, but now pantiless, for the first time.
Meanwhile, Denise (that "other" Denise, as I sometimes compartmentalized her) had called me on Sunday evening, and had gotten me to commit to flying out over thanksgiving. All innocence, but very chipper in her conversation, a few hints at how "great" her life had been lately, but nothing clear. I didn't pry - of course, I knew. If I hadn't known, I'd have been led to speculate, because of her tone, that maybe she finally had found a boyfriend or something.
In a weird sense she had, I thought… and my imagination went into overdrive, at the thought of being there at her house over thanksgiving, after what we'd been "sharing." Meaning: I was developing some fantasies around the sorts of dares I could give her "around the house" while she had "guests" - namely, me.
That Monday I got a short note, thanking me for the great task, and promising me more news the next day. I sent her a task to repeat the dildo-in-the-restroom one, but this time, she was to do it while there were more people in the office (i.e. it had to be during regular office hours).
And no reply. We'd be corresponding for over 2 weeks, and this was the first day she'd missed completely. I sent a note, saying I hoped everything was alright, but found myself imagining the worst - that she'd figured out who I was, say, or something had gone wrong with her task, that she'd been caught. The former would've been much scarier than the latter.
It occurred to me that I was putting my relationship with my sister at risk through this deception, and I had my first twinges of guilt and conscience. I might have given it up entirely, except that the subsequent days events took the whole thing in a very bizarre, perhaps disturbing, but, without a doubt, definitely more intense direction.
It wouldn't have been difficult for her to figure out who I was. The email address I was using was anonymous, and I was using the same pseudonym I'd used to post the stories, but I was using email forwarding from a domain that I owned - if she'd been just a little more technically sophisticated with computers and the internet, all she'd have had to do is view the WHOIS of the domain, to see my name staring back at her, awkwardly. I knew I wasn't immune to detection if she decided to investigate, and she was no dummy with computers, though she generally didn't seem terribly interested in them except as tools for get things done.
Naturally, when I didn't hear anything the next night, either, I got really worried. I nearly called Denise, to make sure she was OK, but thought that would be out of character, given I wasn't supposed to have been in daily contact with her, these past few weeks. If I didn't hear from her by the weekend, I'd call Denise under the pretense of arranging the arrival/departure time of my visit on thanksgiving, though it was a bit early for such a call, relative to when I normally arranged such things (i.e. day-before-departure is my normal modus operandi).
So, instead, I sent another worried-sounding note, asking if I'd done or said something to offend (not likely, though, given the cheerful, relaxed tone of everything up to that point), and saying that if she wanted to stop, no problem, but I'd still like to stay in touch with her, as she'd begun to "feel like a friend" as I put it.
I had a restless night, wondering if I was becoming infatuated with this internet alter-ego of my sister with whom I was having this complex, erotic, yet in some way rather impersonal exchange. It was easy to see happening, given how much I'd always been secretly infatuated by her, in my own distant adolescence.
Finally, on Friday, I got a note from her. Not explaing much, simply saying that because of "some things" that happened she did, in fact, wish to stop the "game" - "at least for now," she added, mysteriously. "But," she continued, "thanks for your concern and kindness." A bit impersonal. I couldn't figure out what had happened, and I really did imagine the worst - that she'd figured out it was me, her brother Jason.