Babysitter’s Clogs

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Now that clogs were back in style this past sum-
mer, I’m reminded of an early sexual experience. It was
near the end of summer. I was in seventh or eighth
grade and had just biked home from swimming practice.
My dad worked in the city and my mom was away for the
day, so Stacia, our baby-sitter, was there to take care
of my baby brother.

Stacia lived behind us, one house over. I had a
mad crush on her, but she had just finished high school
and I could only worship her from afar. Here ash blond
hair and her throaty voice made her seem wild and un-
tamed to me. I was always flustered around her, with
conflicted feeling of lust, embarrassment, and awe. We
were about the same height. However, she always wore a
pair of brown, wooden clogs with three inch platforms,
so it felt like she towered over me. Clogs were pretty
popular back then and quite a few girls wore them to
school. Stacia’s clogs had the highest heels, though.
Anyway, I’ll always associate brown, high heel clogs
with Stacia and a wonderful, early sexual experience.

Stacia was in the living room watching a soap
opera on TV. I came in all excited and nervous and
stammered out a hi. She smiled up at me.

“My, don’t you look cute in that skimpy, blue
swim suit,” she teased.

I turned red and stared down at her clogs. In
my rush to get home to see Stacia, I had simply put on
my T-shirt and biked home, instead of changing. I only
wore my speedo suit during practice because I was self-
conscious about the way its tightness and lack of mater-
ial accentuated my crotch. My penis, which was semi-
hard with the anticipation of seeing Stacia in her high
heel clogs, withered to nothing.

Noticing my embarrassment, she assured me that
she was just kidding and then complimented me my on my
tan to change the subject. I knew I had a savage tan
and beamed proudly. She leaned forward, resting her
elbows on her knees.

“Take your shirt off. Let me see your tan all
over,” she said in a hushed, wicked tone.

I shook my head shyly and continued to stare at
her clogs.

“Come on. What’s the big deal?” she asked as
she stood up. I’ve seen you in your speedos at the pool.
Pretend we’re at the pool. I dare you to take off you
sneakers and T-shirt.”

I continued to stare dumbly at her clogs, but
was slowly getting excited at the prospect of being
almost nude in front of Stacia. I had been swimming
hard all summer and was quite proud of my body. A
surge of hormones and I kicked off my sneakers and
pulled my T-shirt over my head. Standing in my near
nakedness, I felt a flood of warmth enter my loins.
My body quivered with the anticipation of a stallion
about to mount a mare. I was aroused.

“Mmm,” nodded Stacia appreciatively. “You have
a nice, firm swimmer’s body. If only you were bit tal-
ler,” she added, wistfully.

I protested immediately that we were about the
same height and it was only because she was wearing high
heel clogs that she seemed taller. She laughed.

“So you noticed my high heel clogs. You’ve only
been staring at them since you came in. Anyway, the
heels aren’t that high.”

She sounded a little defensive and was pensive
for a moment.

“Here, see for yourself.”

She kicked off her clogs and motioned for me to
try them on. I became very excited at the thought of
wearing her clogs. Because she seemed out of reached,
I must have subconsciously fixated on her clogs and now
was my chance to experience a part of her: to wear her
high heel clogs. I eagerly slipped into her clogs.

The clogs felt wonderful. The insoles were pad-
ded making the clogs luxurious. The height of the heels
created a padded arch that pressed deliciously against
the soles of my feet. Best of all, I now towered over
her and felt bold and daring. I knew my erection was a
prominent tent pole, pushing against the tight fabric of
my speedos. I proudly faced her with my feet slightly
apart, my hands on my hips, and my cock straining for
release.

“All it takes is a pair of high heel clogs, and
you turn into a little tiger.” she smiled.

She looked up at me slyly. She placed her hand
on my chest and my breathing became audible.

“Speaking of little tigers…”

She suddenly reached down and grabbed my balls
aggressively. I gave a yelp of surprise, which pleased
her greatly. Here was this beautiful dream object
touching my intimate parts. I couldn’t believe it. Then
as I stood there trembling in my lust, confused as what
to do, she undid the string of my speedos and worked the
bathing suit down to my knees. I felt my raging erec-
tion pop free, the feeling of that was absolutely
liberating. To be exposed to her view, and by her own
actions almost stopped my heart.

What happened next, almost killed me. She
encircled the base of my cock with her fingers and
knelt in front of me. I watched as if in slow-motion
as the beautiful creature took my swollen boy-hood and
moved her lips to it. I didn’t know what she was going
to do to me until I the warm, moist sensation of her
wet mouth and flickering tongue on my cock-head. This
quickly overwhelmed me with pleasure and I came in body
shaking spurts.

She got up and ran to the bathroom. I heard the
toilet flush. When she returned, I was still standing
there in her high heel clogs. My speedos were now down
at my ankles, but my dick was still waving in the air.
She was amused to see it still hard, I think.

“What am I going to do with you?” she teased.
“You come like a flood and you’re still hard. Well,
we’ll just have to stuff tiger back into your speedos.”

She pulled my speedos up and awkwardly covered
my hard cock with them.

“Can I have my clogs back?”

Everything had happened so quickly and I was
reluctant to let the experience slip away.

“Can I wear them a little, I mean. Can I try
walking around in them.”

I felt like a little kid asking that, but she
nodded understandingly. She took me by the hand and
led me to the dining room, which had a wooden floor.
It was then that I knew I’d always love the wooden
clomping sound of clogs. I was wobbly at first, but
then I got the hang of it. We didn’t say anything.
Eventually, I sadly returned the clogs to her. We both
tacitly understood that we would not breathe a word of
our experience to anybody.

Stacia turned on the TV and sat down on the
couch. I awkwardly sat down on the opposite end.
Stacia casually propped her legs up on my thigh and
gently rubbed my cock through my speedos with her clogs.
I began to caress the clogs and her feet and then
started to rub the clogs vigorously against my cock.
She encouraged me to come again and soon my speedos
filled with my seed. It was then that she kissed me
tenderly on the lips. She told me to clean up and to
stay in my room because my mom would be home soon.

I only saw here one time after that before she
left for college. She called me over from her backyard
and we went into the den of her house. I was pleased
to see that she was wearing her high heel clogs and was
hoping for a similar sexual experience. We both sat
down on the couch and I awaited with giddy anticipation
for her.

She noticed my excitement and said that she just
wanted to talk about the other day and why it happened.
I was disappointed, but also curious. She explained to
me that she thought I was a sweet, shy kid and she
wanted to be my first sexual experience, especially when
she saw me in my tight speedos. She had only planned to
caress me with her hands until I climaxed, but feeling
my excitement and wanting to give me as much pleasure as
possible, she impulsively decided to suck me. She also
admitted to being pleased at how much I enjoyed her
clogs and couldn’t resist rubbing them against me, even
though she had only planned to make me come once.

Aware of my sensitive ego, she admitted she was
tempted to “fuck my brains out,” but she thought it
would be best to not have any further sexual relations.
I was crestfallen and it showed. To cheer me up, she
took off her high heel clogs and handed them to me. I
brightened immediately.

As before, she kissed my tenderly on the lips.

“Whenever you slip my high heel clogs on,” she
whispered in my ear, “I want you to think of me and how
I couldn’t resist just stroking you, but had to have you
in my mouth.”

I wonder where she is now. I will never forget what she
did for me, and I often think of her. I wonder if she
ever thinks about what happened between us…

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