Wow. I closed my email program and looked down at my swollen, throbbing
cock. I very much wanted to masturbate, but was even more committed to my
imaginary solidarity with Denise and Lissa, as I put them through these
tasks (even though they appeared so wrapped up in their own excitement and
experiences it had been quite some time since either of them had shown any
interest in my own erotic situation – as Finn, not as Jason, obviously –
but I really suspected both they preferred it that way, as it kept things
just impersonal enough that it made the whole idea of sexual tasks over the
internet more, well, “do-able,” to use a word Denise was fond of).
Finally, I set my insistent cock aside (metaphorically, anyway) and
logged onto yahoo. I knew Denise had a laptop and a docking station in her
bedroom, and I suspected she might be online. Sure enough, there she was.
“Lissa told me you might show up,” she sent almost immediately.
“Waiting for me?”
“Yep. I was hoping I’d see you. How are you?”
“Very good. I hope you’re doing well, too. I got Lissa’s emails.”
A bit of a pause, then, “I’m almost worried she’s having too much fun.”
“How do you mean?” I asked.
“She’s giddy. I just worry it’s not right the way she’s teasing Jason.
Both of us, teasing him, really.”
“Your brother, you mean?”
“Yes.”
“You think he minds?”
“Haha probably not. He’s probably whacking off in his room right now,
poor man.”
“Well then everybody wins,” I sent back, trying to reassure her, and
loving the idea that she imagined I was here in my room masturbating, for
some reason. “I hope you put some tissues in there for him,” I joked.
“Oh dear… I didn’t think of that. Maybe I should go offer him some?”
“If you want,” I said, my heart leaping in my throat for some reason.
“Nah… he’s a grown boy. He’ll find something if needs it.”
“Good plan,” I commented, just to keep the conversation going. Thinking
back to the clearly sincere concern she’d expressed, earlier, I added, “I
wouldn’t worry too much about Lissa. She seems like a very confident girl
who knows her limits and desires. She’ll draw the line where and when she
needs to.” I actually believed this, though I also realized it stank of a
bit of rationalization even as I typed it and hit send.
“You’re probably right. Maybe my real problem is that it disturbs me a
bit that I find it so exciting.”
I was puzzled by this comment – wasn’t sure what she was referencing.
“What do you mean?”
“I mean… I almost find Lissa’s tasks and what she’s doing more
exciting than my own. Like… like I wish I’d been half as daring and
brave and naughty when I was that age.”
“Ah, I see.” I decided to make a guess, hoping it was true, and, even if
not, to suggest it just for its sheer perversity. “You’re re-living your
own adolescence, with your brother Jason, vicariously, through the way your
daughter’s teasing him, now.”
“Oh my god, exactly!” she replied after only a short delay. “I’m really
so glad you understand, Finn.”
“Well, just remember she’s a separate person, and don’t push her. But
as long as she’s having fun, I see nothing wrong with the fact that it
turns you on to see her do it.”
Long pause.
“Are you still there?” I finally asked.
“Yes…”
“Whatcha doing?”
“Wishing I could cum.”
“LOL not yet, dear. Patience.”
“Lissa told me about her bonus task, earlier,” she said.
“Yes?”
“Could you give me a bonus task, right now?”
“What sort of task?”
Pause. “Don’t make me say it.”
“I’m not going to let you cum, Denise,” I finally typed. “Not tonight.”
“I know I know. But I want to do something kinky.”
“I see.” I thought for a while. Finally, “Find an excuse to bother your
brother where he’s sleeping. Is he in a guest room?”
“Yes,” she answered.
“Tell him you can’t sleep, or something, and you’re doing some work and
there’s something in there you need.”
“That’ll work,” she agreed. “The room he’s in is my home office… I
can say there’s some papers in the desk I need, or something.”
“Good. Here’s the catch… you do it naked.”
“No way…”
I let her worry for a minute. “Well, but you can wear a robe.”
“That’s not bad, then,” she replied, relieved, I suspect.
“So, nothing but a robe.”
“That’s all? Easy…” I sensed she was almost disappointed.
“There’s another catch.”
“Oh ok,” expectant.
“You have to have that new dildo of yours clamped inside of you. The
whole time.”
“Oh … wow.” A bit of a silence.
“And you have to chat with him. Sit down on his bed… at least 10
minutes.”
Finally, she sent back, “Crap. Ok. I’ll do it. I asked for it LOL”
“Good girl,” I sent. “Have fun.” But she’d already signed out. Eager,
indeed.
I quickly hibernated my laptop and slipped it under my bed. Then I
debated whether I should pretend she was waking me up, but decided I didn’t
fake being woken up very well, and then, with some inspiration, thinking
about the earlier exchange, I realized the perfect thing – she was going to
be interrupting me as I masturbated. How obvious. I wasn’t going to let
her catch me… but I was going to have the right flush to my cheeks, so
to speak. Easily enough done.
With that, still naked under my covers, I began to vigorously stroke
myself. I was so far gone, that long before her knock came on my door, I’d
had to stop and take a break for danger of filling her guest bed with my
cum. When the knock finally came, I was genuinely startled, despite my
anticipation of it. I counted to five and rumpled the covers over me,
raising one knee to conceal the turgid, throbbing lump I was wearing, and
said, “yes?”
Denise poked her head in the door, and said, of all things, “are you
decent?”
I couldn’t resist, and, in my best innuendo, said, “never decent, but at
least I’m under the covers.”
She actually giggled, and crept in. “Sorry to bother you, Jase… I
couldn’t sleep, and was doing some work. I left some account folders in
here, and I saw your light was on under the door.”
“Go ahead, sis,” I said, grinning up at her.
She walked over to the desk, and leaning, pulled down one of the binders
on the shelves that made up the upper part of the unit. She opened it up
and studied it intently for a few seconds, flipping through some pages.
She was convincing, if she was pretending. Of course, she probably did
have account folders in here, and she probably had one in mind, so she was
genuinely looking for it, as she put the one binder down and pulled down
the next and flipped through it. “Here it is,” she finally sighed.
Meanwhile, she was in profile at the foot of my bed. I studied it…
looking for the telltale lump at her groin that would reveal she was
complying with the task I’d given her. Though at this point harbored zero
doubts that both she and Lissa were playing “for real.” Again I felt a
twinge of guilt as I acknowledged to myself that I was the only one being
deceptive, here. What to do?
Denise snapped shut the binder she’d found, scooped it and the other
she’d looked at into her arms, and moved to leave the room. I realized
that the best evidence that she was complying with task lay in her gait, as
she walked. A bit of a waddle – I laughed inwardly – almost like a
pregnant woman’s walk. Cute.
As she reached to door of the room, she turned back to me, allowing her
facial expression to evolve to a reflective seriousness. “Hey, Jase…
can I ask you a question?”
“Uh sure, Denise. Shoot.”
She moved back to the bed and sat down on the edge of it, near the foot,
and turned so she was looking toward me, now looking much more serious. I
almost thought, given how serious she was looking, that she was going to
bust me and this whole amazing game. My heart leaped with nervousness.
“I’m worried about Lissa,” she finally said. Whew. But this did seem
kind of serious.
“What is it?” I asked, all seriousness myself, now. Enough seriousness
that my throbbing tool had calmed and wilted somewhat, under the covers.
She was quiet a moment, biting her lower lip. “Well, she’s doing really
great. And… especially the last couple months, she and I have gotten
really close. Much closer than me and mom were. And… I’m grateful for
that.”
I let her sit silently for a moment, knowing she wasn’t done.
“But I know she misses David. Her dad. A lot. She’s a trooper, and
doesn’t talk about it. But I know she does. Well, and I’ve noticed just
in the short time you’ve been here, she really seems to look up to you a
lot. You’re obviously a bit of a father figure for her.”
“She’s a great kid,” I said, a bit innocuously. Encouraging her to go
on, with my face – she hadn’t really gotten to the serious part, yet.
“I’m a little worried, though… um,”
“What’s the matter?” I asked. I honestly wasn’t sure where she intended
to go with this.
“Well… it’s kind of weird to explain. There’s like, something
oedipal going on.”
I almost laughed out loud, but choked it back in time, and spluttered
out something like “I’m not sure what you mean,” instead.
Denise was clearly a bit embarrassed to go on, but I was actually
marveling at the way she’d taken the topic what had been preoccupying her
in her conversation with “Finn” and managed to broach it with “Jason” with
such discursive grace. Almost as if she knew he and I were the same, but
was “playing along.” No way… no way, I thought to myself.
She continued, “I’m sure you noticed how she spent an hour this morning,
after her shower, hanging out in her towel.”
“Um…” I began…
“Don’t even think about denying you were looking – I saw you.”
“Er… shit, Denise,” I began, feeling busted again.
“Oh crap, Jase… I’m not trying to make you feel bad. Guys look at
girls… especially nubile young things high on hormones, like Lissa
clearly is. That’s not my point.”
“Oh…. It’s not?” I was more confused than ever.
She smiled, as if trying to reassure me. “No, what I’m worried about is
that she was doing it on purpose.”
“She was?” I asked, a bit idiotically at this point. I had no idea what
the script was, anymore.
“Of course. Women can tell these things, about other women. And
mothers about daughters, especially. Lissa was totally trying to tease
you.”
“You think so?” another lame question.
“I KNOW so, Jase. And the whole business during the scrabble game, too.
She’s flirting with you, bro. And my question is, what should I do about
it?”
“Um… ” I said, eloquently trying to buy some time. This was not the
conversation I’d imagined when I, as “Finn,” had suggested she have a chat
with her brother.
Then again, the secret subtext was that both women were, in fact,
intentionally teasing me and themselves mercilessly, as part of a
complicated game with a stranger from the internet, and clearly Denise
wasn’t planning to reveal that tidbit.
Suddenly I realized that, whatever this conversation was, it WASN’T some
weird effort at entrapment, and I laughed at myself for being worried. It
was part of a game, and Denise had something in mind… I just didn’t know
what.
Fortunately, she began to enlighten me. “The thing is, she’s fragile
right now. ‘Cause of her brother, then David, and all that. Hell, I’m
fragile too,” she chuckled, somberly. And continued, “but… so my gut
feeling is that it would be a bad idea for you to call her on it.”
“What do you mean, ‘call her on it’?”
“Well… let’s put it this way. She’s clearly in a phase where she’s
just becoming conscious of her body as, like, a sexual thing. Like…
she’s experimenting. She sees the attention she’s getting from you, and
it’s exciting and interesting. Basically… ” she paused, trying to
formulate her point. Then she let it tumble out: “I’m worried she’ll do
something, and you’ll get upset and reprimand her, and, well, hurt her.”
“Reprimand her?” I asked. Interesting word.
“Look… Jase. You’re my brother but you’re also a man. I know how
men are. You’ll go along, letting her tease you but there will come a
moment when it seems like… she’s asking you to do something. And if you
were an asshole, you’d just go ahead and do it, and damage her that way,
and if you’re a nice guy, like I’m pretty sure you are, you’ll say
something like ‘stop, girl, you gone to far.’ But with where she’s at,
right now, that might damage her more.”
Uh oh… hope I didn’t turn out to be an asshole, after all – I
suspected I might. But I was getting her point, even if it seemed very
shaky from a rationality standpoint.
“Denise, are you trying to tell me to ‘play along’ with her? Or
what…”
She was biting her lip again. And… I suddenly realized, she was
rocking, very very gently, where she sat on the bed. And I remembered what
“Finn” had tasked her with. Whoa… she’s getting really excited from
this. Extremely. My sis was a serious perv. I couldn’t help grinning
stupidly.
She interpreted that grin exactly right, despite the missing
information. “You perv,” and she slapped my foot under the blanket. “But
yes, I guess that’s what I’m saying…”
“What exactly is it you’re worried she’ll do?” I finally asked.
“Well… I don’t know. She might try flashing you, or sit on your lap,
or … I don’t know. The kinds of things girls do, at that age. Stuff I
did, for that matter.” I could tell she was embarrassed by that confession.
“Stuff YOU did?” I asked. “I don’t recall… ”
“Hah, poor Jason. You didn’t really know what was going on. You’re 5
years younger, remember – when I was fourteen, you were nine.”
“What DID you do, when you were fourteen, and I was nine?”
“I’ll tell you another time,” she finally saidl, and sighed slightly.
“Let’s focus on Lissa.”
“Ok.” I swallowed, overwhelmed by the strange mix of tensions. “So…
what is it you want me to do?”
“I’m not asking you to DO anything. I’m asking you to just, um, do
nothing, actually.”
“PLEASE explain,” I said, feigning an annoyedness I had stopped feeling.
This was all very interesting. And exciting, of course.
“Ok. I don’t know what she’s going to do. She might not do anything
more than what she did today – prance around in a towel and giggle some
dirty words at you. But if she does do something more… just be nice
about it. Ok? Don’t ‘catch’ her at it, don’t get her in trouble for it.
Just… relax and enjoy it and whatever you do, be gentle.”
I had a startling epiphany. This wasn’t AT ALL about her playing a
complex game around the fact that she might actually know that Jason was
“Finn” and “Finn” was Jason. It was the opposite. She was completely
certain that I had no idea what might be going on, and she was trying to
make sure that I “behaved” as this weekend progressed.
I put myself in her shoes for a second – here’s her brother, visiting
for a few days. Here’s her daughter, working hard to act as sexy as
possible around him, with her mom’s permission and encouragement: furtive
masturbations, “accidental flashings,” the works. Denise doesn’t know how
her brother was going to react to this. She couldn’t afford having him
think the whole situation needed some kind of intervention (a logical,
ethical response, after all). She didn’t want to have him lecturing her
daughter (who was, genuinely, probably a bit fragile in the wake of losing
first her brother, then her dad’s suicide) sternly about “appropriate
behavior” or some such. Of course. I nearly slapped my head “d’oh!”
And, as a convenient side effect, Denise was getting off on the whole
business of chatting intimately with her brother about her daughter’s
budding sexuality while she sat on his bed with a dildo rammed up her cunt.
And KNOWING he had absolutely no idea. Wow.
All this raced through my mind in a matter of seconds, and I said, “So,
what you’re saying, is if Lissa jumps in my bed naked at some point and
wants to play doctor with her uncle, I should just go with the flow?”
I had meant this sarcastically (and, of course, ironically vis-ŕ-vis my
alternate identity), but I was almost shocked, despite everything, when she
practically clapped her hands and said, “Exactly!”
At this, she stood, stepped a few paces forward, leaned over and kissed
my forehead triumphantly. “You’re really the best, Jason. I’m so glad
you’re my brother.”
I was flattered and stunned. As Denise left my room, saying goodnight,
it began to dawn on me that she’d essentially given me permission to take
things to the next level, in my role as “Finn,” without knowing that’s what
she’d done. She’d sent “Finn” a message I’m sure she never meant to send –
go ahead and see just how far you can get both of them both to go, with
Jason – especially Lissa.
I wasn’t sure I’d act on the content of the message, as I had my own
ambivalences. And, given how I’d come by the “message” illegitimately, too
– but it was certainly fodder for fantasy, I reflected, as I gently,
teasingly edged my engorged, happy-unhappy, tortured cock.