Fooling Around 101 - Version Bravo
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Now, you may think that, once this unorthodox arrangement had been
worked out, I would have jumped in with both feet. After all, I
had just been given access to titillating teenaged titties, and lush
lips to lick, along with pretty, pouty pussy petting, and, for you English majors out there, all sorts
of other opportunities for alliteration.
But it's one thing to get involved with a woman in a natural way, on a
date, or after spending some time together. It's completely
another to say, "Okay, toots, let's get down to business and get my hand
in your pants while the getting is good!"
Neither female said anything to me, either, about when school would
start. So I just tried to act like I normally did.
So it wasn't odd that our first "class" in Fooling Around 101 came as a
surprise to me. It was on a Friday night. The boys played
basketball, but that week's game wasn't until the next night, so we
were all home. Jill had gotten a couple of DVDs and popcorn was
Very casually, she said "Bob, would you run down to the store
please? We're about out of ice cream."
"What kind should I get?" I asked.
"I'll go with him," said Cindy. "He'd never get it right by
So we get in my car and off to the store we go.
"Mom says I can fool around with you a little bit tonight," she said.
"Oh really," I said.
"She recommended we park on the way home. She said the first time
I do anything with a boy, it will probably be in a car."
"And what if the ice cream melts?"
"She said to put it in the trunk, and the weather will keep it
frozen." It was below freezing outside.
"Your mother thinks of everything, doesn't she?" I asked, a little
"She said not to let you touch me anywhere but on my boobs."
"You mean I can't touch you here?" I struck like a snake and
cupped her pussy with my four fingers. I pressed against her body
while she jumped and squealed.
"Uncle Bob!" she laughed,
clamping on to my wrist. She did not try to pull my hand away.
So much for scaring her.
She let me squeeze a couple of times, and then said, "Be good," and made
me move my hand. By the time we got to the store I had a hardon,
but I was able to adjust it so it didn't show. I swear she
grabbed the first two half gallons we came to and hurried me to the
checkout to pay for them.
Back in the car, it turned out she knew where all the local make-out
places were. She directed me to a spot that overlooked the river,
which was frozen over and glinted romantically in the moonlight.
"What if the cops show up and ask us what we're doing?" I asked.
"I tell them you're my uncle, and that I needed some advice on
something personal, and that I have two sneaky, spying brothers, so you
brought me here."
"To the local make-out place."
"Do you have a better idea?" She stuck her jaw out.
I drove her to the parking lot of one of the companies that had a night
shift, and parked among the cars of the employees. I explained
that, unless someone was prowling around, the police wouldn't pay any
attention to cars in this location, because they expected there to be
cars in this location.
Five minutes later we were making out, and my hand was up inside her
shirt again. She had taken off her bra just so I could play with
her breasts. She lasted maybe five more minutes with me tweaking
her nipples and kissing her before she agreed to open her jacket and
pull her shirt up so I could suck on her nipples.
Seeing as how I was supposed to be teaching her restraint, and seeing
as how it shouldn't take an hour to go get ice cream, I cut her off,
made her get presentable, and drove back to her house. I
thought I was clever. If I hadn't planned on staying the night that
night, it might have worked out for me.
But I did stay the night, and it wasn't an hour after everybody else
went to bed that she was back downstairs, sitting on my lap, in her
panties and T shirt, which she happily pulled up to her neck so I could
see, touch and make her happy with my mouth. I'm not sure, but I
think she might have had an orgasm just from me sucking her nipples.
But I learned something important that night. Actually, I
remembered something important. Girls, unlike guys, are quite
willing to stop, when given a chance. They like to be excited and
they love to be titillated. But they'll stop if you let them,
especially if you encourage them.
And most assuredly if they know they can pick up where they're leaving
off, the next time.
Teaching Fooling Around 101 was very interesting. I'll tell you
that. It was interesting on several different levels.
Jill's reaction to it was interesting. She never asked for any
details, or plied me with questions. Several times she asked,
"How's it going?" or, "How are you holding up?" But that was
pretty much it. Had I been Cindy's father, in that situation, I'd
have been hiding out and spying. Actually, had I been her father
I'd have locked her up.
And yes, I know how hypocritical that is.
Cindy was interesting too. Here was a girl I had known all her
life. We had already forged a unique relationship between
us. And that relationship was still there, except that something
had been added to it, rather abruptly, that changed the dynamics
completely. Yet this new thing was a secret, which had to
be kept from her brothers, and which her mother, more or less, didn't
want to know about either. It led to some odd situations.
It wasn't odd, for instance, if Cindy and I were in a part of the house
alone, for her to flow up against me and hungrily kiss me. Her
hands might slide down and grip my butt, or she might thrust her
breasts against my chest and squirm. Then, literally two minutes
later, we might sit down at the table with the others and eat.
She was almost always the initiator when this kind of thing
happened. I think that was because she had a better sense of
where everybody else was in the house. But I got in a few moves
too. If no one was watching, I might let my hand slide across her
ass, or I might slide my hand around her back to cup a breast. It
wasn't the kind of thing a boyfriend might try to get away with, but I
chalked it up to fooling around.
It was also interesting that Cindy was very good about keeping her
exploration to once a week. If she couldn't go somewhere with me,
in which case we fooled around in classic style in my car, she'd wait
until everyone was asleep and come see me for some one on one, personal
The exception was if the boys and her mother were gone at the same
time. Any time that happened, she called me and either had me
come over, or came to my house. Technically, she could have come
to my house after school any time she wanted to, but she never broke
the rules like that.
I took things very slowly. For the longest time, all we did was
kiss and I played with her sweet, soft breasts. I know that
sounds boring, but it was more complicated than that. That's
because we talked, while we did this. I talked about how boys
felt, and what they wanted. I told her the kinds of things they
might be afraid of, when it came to girls, and what they might try.
For example, one night, while I lay on the couch, and she lay on top of
me, dressed in her T shirt-and-panties jammies, I let a hand slide down
her back to her bottom.
"Guys will want to touch you here," I said.
"Should I let them?" she asked, breathing into my mouth.
"Do you like it?" I asked, cupping and squeezing her ass cheeks.
"I don't know. It's okay, I guess," she said.
"When I do it, does it make you want to kiss me more?" I asked.
"Not really. It just makes me think about how I sit on that, so
what makes it sexy."
"In that case, it's probably all right for you to let the boys touch
you there," I said.
She liked to lie on top of me with her shirt and mine pulled up, so
that her hot breasts were squashed against my chest while we
kissed. She liked it when I stroked her naked back that way
too. It wasn't unusual for her to rub her loins against me,
though I don't think she was really aware of it. It didn't seem
intentional and, at that point in things, I wasn't ready to deal with
things below the waist. But one time I rolled us sideways, with
her trapped between me and the couch, and we continued to kiss until I
was half on top of her. I humped her thigh with my boner, and
felt her tense up.
I stopped kissing her and asked her how she felt.
"Weird," she said softly.
"What you're doing right now is scary, except that I like it."
"Does the fact that I have an erection bother you?" I asked.
"You always have an erection," she said.
"Pretty much," she said. "The first time I sat on your lap and
felt that, it made me feel good."
"So you like my erections?"
"I love your erections," she
"So why is it scary when I press it into you?"
"Because it's so close to my ..." She trailed off.
"Go ahead," I urged. "Use whatever word you would with your
"Well, we'd say coochie, but that's a little girl word," she said, her
face getting red.
"Do you want to call it something else?"
"It feels nasty to call it ..." She tapered off again.
"Pussy?" I helped.
"It's so strange to hear you say that," she sighed.
"So you get nervous when I press my erection against you so close to
your pussy?" I suggested.
"It sounds stupid to say erection and pussy in the same sentence," she
said. "But yes, I guess it makes me nervous."
"Good," I said. "It should
make you nervous."
"Not with you," she countered.
So I crawled the rest of the way onto her and pressed the bottom of my
boner right between her legs. They were tightly closed, mind you,
but I sank between her thighs and the tip of my cock pressed right
against her sweet spot through our underwear.
"Baby girl," I said, as she went rigid under me. "Don't make the
mistake of thinking that just because I would never hurt you, means
that I don't want you just as much as any other man wants you.
All men want to be just like this with you, except naked. Even
me. I know it feels like we're just playing around, but this is
She nodded frantically under me. I let my manhood press against
her a little longer, and then got off of her. She put on a brave
face, but she looked pretty shaken up. I'm pretty sure it was the
first time she'd been pinned under a male, helpless, for all intents
Two months later she had her birthday and announced that she had
accepted a date with a boy named Charley, who she went to school
with. I was sad for multiple reasons. I'll be honest and
admit that, as far as I was concerned, those precious teen titties of
hers were mine. I had lovingly sucked her nipples until she
trembled and shook. I was pretty sure she'd had orgasms with me,
even though I'd never touched her pussy, with the exception of that one
time I told you about while I was lying on top of her. But her
orgasms were the quietest I'd ever witnessed.
So I wasn't all that happy that another guy was going to get access to
those breasts. I felt the same way about her lips, for that
matter. And I was pretty sure that this very odd relationship was
supposed to end when she started dating. I mean I was supposed to
get her ready to date ... and now she was dating.
But to be honest, I'd been more involved in having fun with her, than
"preparing" her for anything. Granted, we
did talk about relationships and
boys and sex in general. But I had steered away from serious
petting. I mean she was fifteen
... you know?
Well she had been
fifteen. Now she was sixteen.
Anyway, she went on her first date with Charley. Nobody suggested
it, but I stayed over that night. Jill and I waited up for her.
Now, as odd as this whole thing had been, I had never felt constrained
Until this night.
I mean, the whole thing between Cindy and me had been her idea,
right? But once she had gotten us together, she had stepped back,
not wanting to know what was going on. At least she never asked
me any questions about it. So I couldn't figure out why I felt so
tense. Other than the fact that 'my' titties and 'my' lips were out
there, exposed to some other guy, I mean.
Don't ask me how, but I dozed off. Then, suddenly Cindy was
home. She looked completely normal, which seemed wrong somehow.
"Well?" asked her mother.
Cindy shrugged. "It was okay, I guess. We went to
McDonalds, and then to the park. We swung on the swings for a
while and talked."
"Did you do anything else?" asked Jill.
"If you mean did we make out, I'd say no. He did kiss me a couple
of times." She looked at me. "You kiss lots better."
"Maybe he didn't have anybody to practice with," I suggested.
She grinned. "Like I said. It was okay. He wants to
take me out again. I told him maybe."
"Don't tease," said Jill. "If you're going to go out with him
again, tell him so. And if you're not, tell him that too.
Don't string boys along."
"I'm not," said Cindy. "I just told him to think up something for
us to do, and if I liked the idea, we'd go out again."
I woke up when Cindy whispered my name.
"What's wrong?" I asked, my mind fuzzy.
"Nothing," she said. "I just want to cuddle."
"You just came back from a date," I said.
"I didn't cuddle with Charley!" she said, like it should be obvious
why she didn't cuddle with Charley.
"You said he kissed you," I reminded her.
"That's not cuddling. Besides, you haven't taught me everything
"I'm not supposed to teach you everything," I said.
"You've never touched my pussy." There was the briefest
hesitation just before she said "pussy."
"I'd have gotten there," I said. "But you turned sixteen."
"So, you turned sixteen and started dating. I thought that ended
your ... um ... classes."
"Don't be stupid, Uncle Bob," she said. She sounded so disgusted
that I actually felt stupid.
We had pulled out the bed on this night. Cindy had been in that
bed with me before this, but that had been when she was fifteen and I
was (admittedly) playing at teaching her about sex. And I
realized that now, as she crawled into bed with me again. This
time she was sixteen, and had been on a date.
Now I know that doesn't sound like much difference, but I told you this
whole relationship was complicated. There were nuances that I
can't really explain.
I'll give you an example. Remember, on that first night, when
Jill caught her begging for a kiss? Well, then, you remember
that, when she hustled up off my lap, she put her hand right on top of
my boner. She didn't stop and squeeze it or anything, but it was
obvious to me that she felt it ... knew it was there.
Well, after our classes started, she liked to touch it. I don't
mean grab it, or squeeze it, or jack on it. All she ever did was
touch it, either with the flat of her palm, or the back of her
hand. Sometimes she'd rub against it, but only as long as she was
on top of me.
But we never talked about it. By that I mean we never
talked about my boner, other than her comment that I always had one. We talked about boners in general, and
when they happened, and how it all worked, from a physiological point
of view. We spent hours talking about erections, but never about
my personal erection.
And while we talked, she'd touch my erections.
You see what I mean? It was just very complicated.
And somehow, having turned a year older, and having a date under her
belt, it was just all different when she crawled into bed with me this
time. Oh, she settled in next to me just like always, and her
hand draped over me, just like always, but I sensed something different
in her this time.
Tonight ... she was turned on.
She'd been turned on before. Like I said, she'd shuddered through
what I was pretty sure were little ladylike orgasms with me, and her
kisses could be very passionate. Her moans, as I sucked her
nipples were full of passion too.
But there was a subtle difference tonight. Given time to
think about since then, I have decided that, whether Charley was make
out material or not, what really mattered to Cindy that night was that
she was out, flying free, and could do anything she wanted to for the
first time in her life. And she could do it with what amounted to
a stranger. And that freedom
was what got her going. And, since Charley wasn't make out
material ... I got the benefit of all those hormones.
But all that got figured out later. What I was faced with that
night was a girl who wanted something amazing to happen to her, and she
came to me to get it. And since I had never touched her pussy,
she expected that amazing thing to involve that.
In one sense, by not touching her there ... I set things up so she
demanded to be touched there.
Of course I didn't know that either.
But there is one other component that needs to be identified before we
go on ... another one that I was unaware of when she crawled into bed
And that was that in her mind, the touching of her genitals, just
necessarily involved the touching of mine as well.
I found this out when, after a few warm-up kisses, I told her how a boy
would try to engineer getting his hand where he could "accidentally"
touch her. I moved my hand to her panty-covered hip, and then let
it slip between her thighs, where her flesh was soft and hot. I
let my fingers drift upwards, and felt her hand touch my boner - I
always had a boner when we played - just like it always had, just
registering its existence.
My fingertips grazed across the gusset of her panties, and she lifted
her upper leg, bending her knee, giving me room.
"You might not want to do that," I whispered.
"Why?" she asked, her lips brushing mine.
"Because he might be tempted to do this," I said.
I don't know what came over me. I honestly don't. Maybe it
was all that passion that I had restrained. But what I did was
move my hand up, dip my fingers under the waistband of her panties, and
then slide my hand into a hot, slippery, positively soaked pussy.
She jerked, gasped and arched into a rigid bow as my middle finger slid
easily across her erect teenaged clitty. That thrusting of her
pelvis sent my fingers lower than I had planned, and my middle finger
dipped between her labia and into her furnace-hot pussy. The
groan of passion that ripped from her throat was like a dagger of fire
that swept through my balls, and penis, and belly, and brain, and the
next thing I knew, I had my middle finger buried in her, the fingertip
circling and teasing the lips of her cervix, as she squirmed and panted.
"Oh fucking shit!" is what I
believe she gasped, but I wouldn't testify to it in court.
And the next thing I felt was
her hand, sliding into
my shorts, and grasping my erection
in a tight fist. And bless her heart if she didn't start stroking
me just like she'd been doing it for years.
I do not know what those little shudders she had done in the past
were. Really, I have no idea. I had thought they were orgasms, but maybe not. That's because, with my finger buried in her hot
pussy, Cindy had a bonafide, honest-to-Pete, genuine, full blown, real
McCoy orgasm. Her hand left my penis (much to my dismay)
and darted for the pillow that was under my head. With surprising
strength, she pulled it toward her face and then buried said face in it
while she had that orgasm.
Even with her face buried in the pillow it was loud. It was
so loud that I was pretty sure somebody would come to
investigate. And while Jill might have been able to deal with it,
I was also pretty sure that if two almost-eighteen-year-old boys showed up
and found their sister with a long, fat finger thrust up her pussy,
there was going to be an asswhippin'.
That didn't happen, thank goodness.
Instead, she flopped back onto her back, and her hand came to grip mine
through her panties, and she gasped, "Wait!" while she dragged in huge
lungfuls of air. I did, and about fifteen minutes passed,
before her hand started moving mine again and she rolled towards me to
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