Jesse’s Fantasies

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Age: 35
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Jesse’s Fantasies

You called me, again, out of the blue. It had been months since I heard from you but there you were on the other end of the line.

You told me that you think of fucking me a lot. You said you look at the pictures I sent you on a daily basis. Your cock gets so hard you think your pants are going to burst open.

I told you to send me a picture, one showing your bulging cock so I could see what I was in for. And boy did you please! I want that cock in my mouth, in my wet pussy, in my sweet ass, I want it everywhere, filling me up.

I want you to pound my pussy, ass and face with that big, hard, purple head. Even if I beg you to stop, keep going, fuck me until I cry with pain and pleasure all at once.

Make me do things I have never even imagined. Make me yours. Tie me up, whip me, pull my hair, fuck me so hard I feel like I am going to break. Don’t listen when I ask you to stop. Punish me for it.

Make me crave you. Make me feel like I am only alive when you are fucking me. Make me happy that you called.

I feel you…

watching me.

I feel your eyes on my back. I feel a twitch inside, a tingle of excitement.

I know what you like.

I know what you want.

I feel you undressing me with those eyes.

I smile with my secret knowledge.

You follow behind, a distance far enough, but I know you’re there. If I
stop, you wait. You think you’re sly but you’re not enough, for me. Albeit
I don’t actually try to lose you. I like it. You know I like it.

I see your car again. You are parked across the street.

You peep through my sheer drapes with your binoculars and I am aware.

I smile slyly, knowing the show is about to begin.

I turn on the music.

I dance for you. My hips sway back and forth, my soul is lost in the
music. My eyes are closed but I know you watch.

I know I turn you on, I undress for you while I dance.

My arms are above my head, my tits perky and aroused. I slip my panties
off. I am now nude, swaying with the sound just for you.

You get out of your car and come to the window. I see you. I dance awhile
more, knowing it kills you, you ache while you watch and I know it.

I leave the music on but turn off the lights.

I go to the door and unlock it before I head to my room.

And I wait for you.

I have had this fantasy for a long time now and I am still waiting for it
to come true…

I am standing down at the marina, in front of the Yacht Club, leaning up
against the gate leading down to the most expensive boats I have ever

The sun is shining brightly and the skies are blue with just a few billowy
clouds every now and then that could be anything when you used your
imagination! I was making things out of clouds and watching boats go in
and out, lost in my own world when suddenly I have the sense that someone
is behind me.

Just as I begin to, a voice says, “Don’t turn around. Do not say and word
and do not turn around.”

His voice was strong. Not mean or aggressive, just manly, sexy, firm and

Although it was a very warm day, and I was dressed in a flirty short skirt
with a tank and flip flops, I knew he was dressed oddly when he moved
right up behind me, his body so close I could feel his hardness on my ass.
He had an overcoat draped over his shoulders like a cape. He wrapped the
sides around me partially shielding me from the sides.

I began to say something and again he said, “Do not say a word.” As he
said this, he wrapped his left arm around my waist pulling me so close it
was now evident what he had in mind. His bulging cock was throbbing
against my ass as he takes his right hand and puts it down my skirt in the
front. He starts rubbing my pussy through my lacy thong panties.

His fingers trace my lips over the lace when suddenly he pulls my thong to
the side and darts his finger into my hole. I gasp quietly, aware that I
am becoming very wet. My body start to rock back and forth with his finger
and suddenly he puts two more inside me, deep inside. I let out a slow
moan. He takes his fingers out of me and sticks them, one at a time, in my
mouth. I am afraid to turn my head to see if anyone around us, aware of
our activity.

Then he takes his hand, three fingers now wet with my juice and by my
mouth and reaches behind me and sticks his middle finger into my puckered
asshole. The hand the was around my waist now reaches down my skirt and
finds my clit, hard with anticipation. He begins to rub in sequence with
probing. My body involuntarily starts rocking with the motion.

He builds me up to a frenzy, working my clit around and around, back and
forth, and my ass now has two of his fingers inside. Suddenly he pulls his
fingers out of my ass and pulls his cock out of his pants, without warning
he plunges into my cunt with such force he nearly lifts me off the ground.

Now he is pumping me hard, holding me close, his other hand still busy
working my clit. I cannot help myself, I am so turned on, my body is
moving against his so his cock plunges into me with every thrust.

I am just about to lose it when he says “Don’t.”

He slows the clit movements down a bit and then starts pumping my cunt
with a vengeance. Just as I am reaching the edge again, he says, “okay
now,” and he speeds up his finger on my hardness. With that we explode in
unison, an explosion like I have never had before.

As our rythm slows down he continues with light pressure on my clit and I
ride the wave for what seemed like hours. When our bodies finally stop
rocking, he pulls his hands away, reaches up, pulls the overcoat back, and
says, “Thank you. Do not turn around until I am gone.” And with that, I
continue to watch the boats and clouds, never turning until I was certain
he was long gone.
Believe it out not, most time I have no interest in shopping. On a rare
occasion, it can provide a decent break from work, or an enjoyable
afternoon with a friend. But to me its a nuances, there are other
activities that are infinity more pleasurable (!).

Having said that, here I was at the mall looking for sexiest, most
provocative strappy, high-heels I could find. I needed the shoes that
would complement my new ultra-clingy, black satin cocktail dress. Plus, a
mistress can never have enough stilettos. Joy, a friend I’ve known since
our days in acting class, had scheduled her annual Holiday party. The
event is always a huge smash, great food, ample alcohol, and all-night
dancing and flirting among the beautiful people.

Targeting the most expensive department store first, I hoped to make the
shopping expedition as quick as possible. The young salesman looked a bit
out of place in the women’s shoes department but at least was cute. 6 feet
tall with a slim, athletic build. He was nicely groomed with a neat
haircut and sparkling white teeth, looking professional in a shirt and
tie. He couldn’t help but stare as I walked over to the display, his eyes
practically popping out of their sockets. “Ah Jesse, yet another
fan”, I thought to myself. After my usual teasing routine of reaching for
items while arching my back, bending at the waist to pick-up shoes,
absentmindedly playing with my hair, and shifting my weight from one foot
to the other – accompanying by an ass sway, I knew he’d be hooked.

I turned quickly from the display rack to see him approaching, his eyes
locked on my perfectly shaped ass and legs with a look of utter adoration.
His deep blush and the twitch of his cock almost made me giggle.

Handing “Alan”, from his name tag, the display 5″ peep toe sling-back
pump, I sent him on his way to find my size in the storeroom. When he
returned I was already sitting in one of the customer chairs with my flats
off. The eager young lad immediately knelt in front of me, opened the
box, and gently helped my feet into the heels.

I made sure to move my feet in his hands more than necessary, twisting
them from side to side, and back and forth to ensure there was plenty of
physical contact. If that wasn’t enough, I exaggerated the sway of my
hips as I walked around the department checking the fit. Sitting back
down, I pretended I was unsure if I liked the pair. Turning my foot so I
could see the shoes from different angles, I continue to “accidentally”
brush the inside of his thigh, each time making the contact more

Sensing his breath was becoming noticeable more shallow, I teased his
balls with the toe of the shoe through his dress pants. Then rubbed his
growing cock several times with the bottom of the pump. A quick look at
his face told me he was enjoying the torment, his eyes rolling up into his
head, his mouth slightly open gasping for air.

Although we were alone in the shoe department, I had no way of knowing how
long that would be the case. An experienced mistress knows when to go in
for the kill.

I move my foot further back, using my big toe to rub and probe his
puckered ass, his rock hard cock tenting his pants, and bouncing against
my ankle. Leaning forward to bring my face closer to his, some firm
pressure with my toe directly on his asshole was too much for the lad.
His cock twitched and pulsed as he shot his tribute over and over, the cum
making a very noticeable wet stain on his tan slacks. Adding insult to
injury, I kicked off the heels at the same time stating “I’ll take them!”.
Grabbing my flats, I quickly walked to the cash register leaving my new
pet to figure out how to get there with a humiliating wet spot.

Maybe shopping is more fun than I initially thought.
Modeling had turned out better then I expected. Although I was in my early
thirties, an agent I met through a friend-of-a-friend, assured me he could
get me work. And he did, certainly nothing with global or wide spread
distribution but several mainstream magazine spreads and two print
advertising layouts. It was fun while it lasted, the jobs were becoming
more infrequent.

The decent cash flow allowed a sizable down payment on a two bedroom condo
just outside the city, two lavish vacations in the tropical islands, and
enough savings to attend graduate school for my MBA. I figured my winning
smile, an advance degree, and my perfectly shape derriere would allow me
to jump in a bit higher on the corporate ladder than mail room attendant.
Plus, the first lesson of business school is to exploit your most valuable
asset. So there you have it!

Studying at a local library had proved worthwhile, both in terms of few
distractions and a chance to get out of the house. I was finishing up the
weekly paper for “Advance Leadership In a Global Economy” when I spotted
what I was fairly certain was my next toy. He looked so proud wearing his
high school letterman’s jacket; “Varsity Track” how impressive! It
appeared he was equally impressed with his attendance at a community
college as both his water bottle and notebook wore their distinctive
emblem. At least his shagging brown hair and blue eyes were cute. The
“Freshman English” and “Accounting 1” books confirmed my initial

I wasn’t even trying that hard and I caught him twice, within ten minutes,
looking my way. My full, curly, honey brown hair and the low cut v-neck
cashmere sweater likely helped some. The third time our eyes met I
remained looking at him until he blushed and pretended to go back to work.

As my paper was pretty much done, I decided I had earned a little
playtime. I stood up to stretch, turned sideways, and arch my back
slightly – allowing him a nice profile of the small of my back and the
symmetrical curve of my ass. Then, to ensure my booty was getting the
attention it deserved, with my back to him, I arranged my jacket on the
back of the chair and shifted my weight from one leg to the other. Having
chosen my tightest jeans that morning was a very fortunate occurrence.

A quick glance after sitting down told me all I needed to know. His mouth
hung open and I swear I could see a tiny drop of drool on his lip, the pen
in his hand hanged limp while his dilated pupils told me other things were
firming-up for sure.

My cruel streak compelled me to further torment the boy. I went to the
restroom and removed my black thong. On the way back to my chair I
stopped in front on him and held out my hand with the intimate garment
balled-up and fully concealed. His eyes seemed to open as wide as
possible as he slowly move his hand towards mine. I placed the still warm
piece of lingerie in his hand and with my other, wrapped his fingers
around the item to ensure others would not see. I
half-smiled/half-smirked at him and continued to my work space. I knew I
should ignore him but my curiosity made me peek. His behavior reminded me
of someone watching a tennis match, his eyes darted from looking at the
treasure in his hand to me and then back again, over and
over. The poor lad, he seemed unsure that what had just happened was in
fact, reality.

A few minutes latter I found my new little friend standing in front of me,
having summoned the courage to walk the ten feet that separated our
chairs. What a big boy!

He started to speak but before he finished the first word I cut him off
without looking up. “I’m in the middle of something right now, maybe we
can talk in a bit”.

I had to smile to myself as there is nothing so fun as sending exaggerated
mixed signals. I killed an hour proof-reading my paper, checking email,
my back account, and a few boot sales. All the time he waited and hoped.

All good boys deserve a reward. I gathered my things and headed towards
the door of the study room without glancing his way. Halfway though the
door I turned to his steering eyes and both motioned with my head to come
and mouthed the word “Now”.

The second floor of the library has individual study rooms along the back
wall. The rooms are the size of a ATM vestibule, half glass doors, shelf
desk, a light and a chair. They have some sound proofing construction,
and I choose the last one to further provide privacy.

I opened the door and waited for him to enter first. The small dimension
ensured we were immediately sharing personal space. Pointing to the floor
increased his general bewilderment. Placing my hand on his shoulder and
applying a little guidance had him kneeling between my legs under the
desk. I unbuttoned my jeans and pushed them down until they were around
my ankles allowing an up-close view of my pretty pussy. My index finger
tapped my abdomen twice, he was transfixed and motionless. I tapped
again, and as his head leaned towards my sex, I encouraged him moving
closer by pulling him towards me with my hand on the back of his head. I
reviled in his submission as his nose touched my slit but he waited for
approval to continue. A firm nudge on the back of his head had him
kissing and licking my lips. I squeezed the back of his neck prompting
more urgent licking and sucking. His tongue probed and explored inside
me. The small room became electric with sexual energy, the intoxicating
smell of my perfume, and two strangers experiencing a passionate exchange.
My teasing and torment paid huge dividends as my boy toy’s pent-up desire
was channeled to my most sensitive spot. His eagerness soon had my body
buzzing and I knew a climax was coming, and soon. I placed my hands on my
thighs and clasped his head between my legs and held it there tightly as
each wave of pleasure washed over me.

Finally catching my breath I relaxed my thighs slightly, but not too much.
He was mine to do with as I wished as long as he was in my presences.
Without looking, I grab a tissue from my purse to dab myself quickly
before pulling up my jeans. The used tissue was passed to junior on the
floor although I was sure it was of little use. Scribbling my name and
phone number on a piece of paper, I unceremoniously shoved it into his
shirt pocket. Sure enough, he called two days latter. I told him I was
busy that week and to try me again next Monday. He did.