Teaching Emily: A Sissies Story
By: Dianna Vesta
Training a sissy can be such tedious work yet highly rewarding in the end. Such
was the case with dearest Emily. Emily arrived at my Manhattan apartment on the
Upper East Side in male clothes carrying a large suitcase. Emily could barely
look at me when he entered through my threshold.
"What do we have here? You certainly don't look like a sissy to me." I
exclaimed.
"I'm sorry ma'am. I have my things in the suitcase." He replied holding up the
large suitcase.
"I don't understand why you didn't come already dressed, Emily. Do you think
anyone would have noticed?" I laughed teasingly.
Emily blushed turning several shades of red.
"Well then why don't you go into the bathroom and prepare for me the sissy I
expected to see. These male clothes just won't do!" I instructed and pointed
towards the bathroom.
With suitcase in hand the nervous male scurried off to the powder room.
It seemed like an hour past before Emily came out of the bathroom and into the
dining room where I was relaxing with a cup of tea. I looked up to see a sweet
little blushing sissy with a cute white dress, locks of curls dressed with a big
bow and Mary Jane buckled strapped shoes. Emily then curtsied for me, all the
while shaking like a leaf in a turbulent wind.
"That's much better! I like you this way!" I praised her.
I got up and moved my chair towards the center of the room. I sat down and
motioned Emily to kneel.
"Come closer and let me have a good look at you."
Emily still kneeling scooted her body closer to my chair. From this position our
eyes could meet. I looked directly into her eyes. Emily could barely look at me.
I lifted Emily's chin with my hand and forced her to look back into my gaze.
This caused Emily to tremble even more.
"Why are you so nervous Emily?" I asked her while still trying to gaze into her
eyes.
"I don't know Goddess. Your presence is overwhelming to me." Emily replied
barely getting the words out of her painted pink lips.
Humiliation excites me. Emily was obviously nervous and I thrived on this. It
was time to take dear Emily to the next level. While still looking deeply into
Emily's eyes I took my hand and lifted the skirt of her dress.
"So are you really a sweet little girl under there? I want to see what's under
those panties."
Emily dared not remove her eyes from my locked gaze. Her trembling intensified.
She couldn't utter a word. I reached between Emily's trembling legs and grabbed
her crotch.
"Well, well, what do we have here?" I exclaimed as I squeezed the bulge in her
frilly silky panties.
"MMMyyyyy little clit?" Emily replied.
"Your little clit? I hardly think it's little Emily. Have you been doing
something nasty to make it grow? It's huge! Far too big for a sweet little girl!
Tell me the truth... has Emily been a nasty girl?"
Emily looked down at my hand under her dress.
"Yes, ma'am. I'm sorry. I've been a very very bad girl." Emily pouted.
"Have you? Well I hardly think that is any behavior for a little lady, do you?"
"No ma'am. I'm sorry. It won't happen again."
I reached up and pinched Emily's nipples through her dress.
"And these? These are awfully large nipples for a sweet little girl. Have you
been touching these as well?" I asked while squeezing her nipples.
Emily looked down at her nipples. "Yes, ma'am. I'm sorry. I know I'm a bad nasty
little girl."
"Emily I won't stand for this slutty behavior, do you understand?"
"Yes, Goddess." Emily was almost in tears.
"I must be assured that you will never do this again. As much as I hate to I
must punish you and teach you a lesson. I am going to spank you and hard. You
will feel the heat of my anger for weeks every time you sit down or move a
muscle in those silky panties. Go fetch that hairbrush on the piano NOW!"
Emily stood up and walked towards the piano. I did not give Emily permission to
stand up and walk so I quickly stood up, followed her to the piano and threw her
up against it. Emily panted nervously as I shoved her up onto the grand piano
with her feet dangling and ass in the air. I lifted her skirt and revealed her
panties.
"I guess we'll have to start here! How dare you stand and walk without
permission! You are really asking for it young lady!"
I ran my hand across Emily's creamy white flesh and then without notice I
smacked her! Emily moaned and jumped.
"Be still girl! I have only just begun!"
I continued to teas Emily by lifting my hand and pretending to smack her ass but
instead I broke the swing with a pat.
"When I build up momentum you'll feel it girl. Your ass is going to sting like
fire!"
Emily whimpered.
"We will continue this in the chair. Get down on your knees and crawl there with
that brush in your mouth." I ordered.
I sat down in the chair. When Emily finally arrived on all fours with the brush
in her mouth I quickly positioned her over my knee. I grabbed the brush.
"This is going to hurt, however you will keep your ass up and available to me. I
don't want to see you flinch and inch. You will count and should you miss a
number we'll start all over. Do you understand?"
"Yes, Goddess." Emily lifted her ass into the air waiting for the first whack.
My hand lifted and came down onto Emily's bare ass.
"One, thank you Goddess, may I please have another?"
I lifted my hand and again came down on her flesh a little harder.
"Ouch! Thank you Goddess, number two! I'm sorry, may I please have another?"
Emily was only on the second smack and already the redness began to appear on
her flesh.
My hand raised again coming down even harder. SMACK!
"OUCHIE, OUCHIE, please...I mean three, Goddess may I have another? Thank you
Goddess!"
This time welts began to appear on Emily's ass.
"I will not tolerate my little girls being nasty and touching themselves. If you
are to be touched I will do the touching!"
SMACK!
"YES, Goddess, I'm so sorry...OUCHIE...I won't do it again!"
"I can't be certain of that Emily. I believe you knew better the first time and
yet you still defied the laws of ladyhood by acting like a cheap whore!"
SMACK!
"OH GAWDESS! Please, thank you...FOUR! May I...please...OUCHIE..please..."
"Please what?" I yelled.
"...may I please have another!" Emily shouted.
"Ask and you shall receive!"
SMACK!
The red welts began to turn a lovely shade of purple. We were far from done. I
wanted to see the red welts bead into a bleed. Only then would I be assured that
I had instilled my demands within Emily. My wrath would be imprinted within her
consciousness for a very long long time.
SMACK!
"OHHHHHH Goddess..I beg you for mercy!" Emily cried.
"Did you miss your count girl?"
"Nooooo..thank you Goddess, that's five, may I please have another?"
Emily now sniffled as she talked, pleading for another yet wishing for mercy.
Her body shivered with pain and her legs shook uncontrollably. With my hand
drawn back several feet from her ass flesh I came down across her backside like
a locomotive....
SMACK!!! SMACK!! Two hard blows to her red welted cheeks.
Emily let out a yell that was heard two NY City blocks. She sobbed
uncontrollably.
"THANK YOU...THANK YOU... Goddess that's number six and may I please...I beg you
for another."
These final blows brought satisfaction as I saw very small beads of blood rise
to the surface of her ass. I was content and now ready to stop Emily's
punishment. I bent down, kiss the sweet bloody ass and then pushed Emily onto
the floor.
"Ok Emily. Now go the piano and play me a song. It better be good or we'll have
to punish you again."
Emily crawled over to the piano. I took off my jacket, lied up on the piano and
relaxed to the music of "Chop Sticks".
The End
