Guided Masturbation Stories


A precocious teenage girl introduces the neighborhood to the pleasures of the hand and CFNM.

Sheila the Great

by schulzie 1998

 

The neighborhood in which I grew up back in the Sixties was full of
"good" girls who had a strong interest in sex, but didn't do much about
it because virginity was somewhat more valued then than it is today.
Guys in my neighborhood might make out and get a quick feel of boobs
occasionally, but that was rare; that is,until Sheila moved to our
neighborhood.Sheila came from another town where the girls were a step
or two ahead of the young ladies in our neighborhood. Not that Sheila
was a slut or anything, but she was a bit more daring than the other
girls.

Shortly after she moved in, Sheila taught me a game called "Trust Me?"
Ever heard of it? I hadn't until Sheila showed me.

One summer night, we were sitting on my front steps talking,and she put
her hand on my knee and asked, "Trust me?" Not being sure what she
meant, I said,"Sure. Why?" Then she moved her hand an inch or two up my
leg and said, "Trust me?" Now I got it. She wanted to play games. The
"Trust me"
question and "Yes" answer game continued as she moved her
hand closer and closer to my crotch. I had a rapidly rising
hard-on, but it wasn't a fully developed woodie yet, so I stopped her
before she got to my dick.

Then it was my turn to ask: "Trust me?" She let me get past her knee
before she said: "No." Then it was her turn again. This time I let her
move up until she touched the head of my dick before I said "No." By now,
I was completely hard, and couldn't wait until the next time. When it was
her turn again, she led me get about halfway up her thigh before she
stopped me. I asked about this little 
teasing game and she told me it was something the kids back in her old
neighborhood used to do. I told her it was an interesting little game.
Then, we started over again. This time I let her get a feel of my whole
cock in its full glory. She gave it a little squeeze, and asked: "Trust
me?" I said "Yes", and then she gave it a much harder squeeze. This went
on for awhile until she was rubbing the length of my erection through my
pants. Being a virgin myself, I was getting real close to shooting a
load in my pants right there. Suddenly, she stopped and said it was
getting late and she had to get home. She started toward her house up
the street. As she did, I thought to myself,"That dirty little
prick-teaser." Then she turned around and said, "Wanna play some more
tomorrow night?" Did I? All I could do was look at her and say, "Yeah!"
Damn right, I did. I went inside to my bedroom and immediately jerked
off.


The next night, I waited on my front steps for Sheila. It and I was
afraid she wouldn't show. But in a few minutes, there she was. She said,
"Is there anyplace around here that we can go to have some privacy?" I
suggested we head for the field behind the woods down the street. Off we
went.

When we got there, we talked for awhile. Then she began the
game again. During the whole time we played, I never got a
chance to feel her pussy which was frustrating since I'd never felt one
before. But she seemed to enjoy feeling my dick. We got as far as we had
the night before with her rubbing my dick through my pants. Then she
took a detour. She asked: "Trust me?" Of course I said, "Yes." She then
started to work her hand up towards my waist and asked:"Trust me?"

"Yes." Her hand moved up more.

"Trust me?"

"Yes." Her hand moved up to my belt.

"Trust me?"


"Yes." She began to undo my belt. My heart was beating like
crazy, my dick was getting harder by the second, and with each
"Trust me?", she proceeded step-by-step to undo my snap, then
my zipper, and slowly made her way down my briefs until she
touched my cock. To make a long story short, she began to give me an
unbelievable handjob. Being young, it took me very little time to cum
which I did...all over her hand. She smiled at me and asked, "You like?"

"Wow!" was all I could say for the longest time. As she
wiped her cum-soaked hand on my jeans, I asked her if that was the
first time she had ever done that.(Duh)

She giggled and said, "No, I've made lots of guys come in
my old neighborhood." Wow! Lucky guys. I tried,
unsuccessfully, to get my hand on her pussy, but she wouldn't let me.
She seemed pleased just to get me off.


We played this game a few more times in the following weeks. I got a
handjob, while she continued to keep my hands away from her pussy. When
we first started doing this, I thought maybe the reason why she wouldn't
let me touch her was because she was having her period. But a week or
two had passed, so it wasn't that. I guess she just was into getting
guys off. Or maybe she didn't want to go farther outside. At this point
I didn't care. I could now say for sure that she wasn't a "prick
teaser."

One day, when her parents were at work, she called me up and
invited me over to her house. Cool, I thought. Indoors. Maybe
I'll get lucky and get a chance to feel her pussy, maybe more.
I got over there, but she wasn't alone. Three other girls from the
neighborhood were there. Damn, I thought, looks like there wouldn't be
any games today. I was wrong. We were all in the living room talking
with Sheila sitting right next to me and the other girls sitting around
us. Suddenly, Sheila put her hand on my knee and said, "Trust me?"

This really caught me by total surprise. She couldn't be serious. In
front of the other girls? I didn't say anything. I froze up.

Again, she asked: "Trust me?" I looked around the room. The other girls
were watching. They seemed interested and apparently knew what Sheila was
up to. Sheila looked at me, then looked at them, and said to me: "I asked
you a question: TRUST ME?" She WAS serious.

All I could do was say: "Uh-huh."

And with that, the game began. I was a bit nervous about what
was going to happen. On the one hand, I was already a bit of an
exhibitionist at that age and this was an exciting opportunity. On the
other hand, I had never shown myself to a group of girls at one time.
These were girls that I had known and grown up with for several years,
fantisized about, had made out with, and now here was a chance they were
going to willingly look at my dick. My HARD dick (I hoped). It didn't
take long to get through all the preliminary "Trust Me" questions until
Sheila had my pants undone and was ready to reach into my underwear. At
this point, Sheila looked at the girls who leaned forward for a closer
look,then looked me right in the eyes and said, very slowly, "Trust
me?"

I nodded, my heart racing, my chest tight, and then...she reached
in and pulled out my cock, exposing me completely to the room of girls.
I never was so excited in my life. The girls had a whole series of
different reactions as soon as they saw my hard cock for the first time.
It must have been the first time they had seen a penis, or at least a
teenaged boy's penis, and certainly an erect penis. Their eyes widened,
their mouths dropped open a little bit. I heard at least one or two tiny
gasps, a "wow", eyes gawking at my dick, then turning to look at each
other, giggles, then more stares at my dick.

Jesus! I couldn't get over this. It was overwhelming. The blood was
rushing to my head as all these girls I knew were staring at my hard-on
all the time while Sheila was gripping it tightly, shaking it at them.
Sheila began to stroke my dick in front of the girls. Oh my God, I
thought. She's gonna make me cum
right in front of them. I was so fucking hard by that time I knew it
wouldn't take long. I wanted to cum in the worst way, yet I wanted this
moment to linger as long as possible.

The girls were continuing to react as they watched Sheila jerking me off.
They continued gawking at my dick, watching Sheila's hand rubbing the
length of my dick, watching my reactions to the handjob. It was more than
I could take. I shot all over my shirt and Sheila's hand and arm. The
girls were taken aback, I think.

I suspect they were not sure exactly what they expected to see. They
looked at my dick shooting cum, they looked at my face, they looked at
the cum. I was breathing as heavily as if I was running the mile,
moaning uncontrollably as Sheila finished me off. Afterwords, I sat back
on the sofa exhausted, a little embarassed to have them watch as the cum
began to dribble down my cock as it began to shrink. The girls were
murmuring and whispering among themselves, so I excused myself and went
to the bathroom to clean up.

While I was in the bathroom, I began to catch on to what the little
game was all about. I heard Sheila tell the girls, "See, that's all
you've got to do. If you make them cum, they're happy, you don't have to
go all the way with them, and they'll do just about anything you want
them to do."

It wasn't long before Sheila's little lesson seemed to have an effect
on the whole neighborhood. There were a lot of us guys geting jerked off
that summer.

Wherever you are, Sheila, thanks a lot.