The White Sissy Slave Society A Walk into Sissyhood
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Releasing My Inner Sissy Part 1 free porn video
RELEASING MY INNER SISSY
By Deewet
2018
This story is fiction and contains mature matter. No real people or
people under age are deplicted in this fiction.
I met Mistress Cindy by accident at an outdoor festival. Sitting alone,
like usual, I was watching a band play, drinking a Coke since I wasn't 21,
and even if I was, I couldn't afford the beer prices. Of course, at that
time I had no idea she was a transformation specialist and dominatrix.
She sat down next to me and said nothing for a long time, listening to the
band.
"You would be a pretty girl," she said, without any prompting.
I stared at the band, trying not to react to what I suspected was an
insult. Since I'm only 5'2' and 114 pounds, I sure didn't make the grade
as a man to most women. I'm usually told I'm cute but not taking
seriously.
"No, really," she continued. "I'm not trying to insult you. It's just
saying you have a lovely face and body."
I dared to look over at her. She was stunning in a wild way. She wore a
tight leather skirt and blue top. A tattoo sleeve covered most of her
right arm.
"Holy shit," she said. "Your blue eyes are gorgeous." She reached over
and felt my long hair. "Come on; you have your hair long. You've thought
about how nice it would be to be a girl." Then she felt my smooth face.
"Do you even shave?"
I don't know why I didn't get up and leave. Maybe it was loneliness that
kept me sitting at that stone picnic table or just the fact that a woman
was talking to me.
"Have you ever tried dressing up?"
"As a girl?" I replied, my voice sounding weak, almost like a girl's.
She smiled. "Yes, as a girl. I can help."
I shook my head and glanced around to see if anyone was listening to us.
Everyone nearby was listening to the band.
She leaned closer to me. "Come over and see me. It will be fun, I
promise."
I was so shaken; I didn't say anything. Mistress Cindy handed me her card
and left.
For two weeks, I agonized over that encounter, looking her card, almost
making the phone call. She was right; I did think about how I'd look like
a girl, although I never dressed up. I had zero female clothes. My hair
was thick, and I had let it grow long because I couldn't afford to get it
cut and sort of liked it. I figured it made me look artsy, but after she
had mentioned it, I saw how it made me feminine.
Finally, on a Sunday afternoon after another disappointing week of meeting
no one, I made the call.
We sat in her living room, drinking coffee. Her three-story brownstone
had to be super expensive.
"My clients pay me well."
I got up. "I should leave. I'm so in debt after four years of college; I
could never pay anything."
"Sit down. The first one will be in the house. I so much want to see you
as a girl."
I moved toward the door, wanting to escape.
"SIT BACK DOWN!" she demanded, her voice firm, a voice I'm sure she used
with her subjects as a dominatrix. My subconscious reacted immediately,
and I returned to the couch. It happened so fast, and out of my control,
it scared the shit out of me.
She returned to her motherly tone. "You have no reason to be afraid.
Everything that happens here stays here. Think of it as your safe zone.
We're just going to explore your hidden self without any judgments. Now,
come on." She held out her hand. "Let's go meet Amanda."
"Amanda?"
"Yeah, that is your girl name."
I seemed to have lost any decision-making rights, so I took her hand, and
she led me upstairs. My mind raced, and I grew so nervous that I thought
I might be sick. Was I doing it? Letting a woman I knew nothing about,
who I met in a park, dress me as a girl. Then a more worrisome part came
to mind. What would she expect me to do as a girl?
She brought me to a room, entirely dedicated to transformation: dresses
hanging on clothes racks, fake heads with wigs, shoes, underwear of all
types, a table covered in makeup stuff. I felt faint and almost stumbled
"It's okay sweetheart. I know it's overwhelming the first time. You
don't need to do anything. Mommy will take care of you. Let's take off
those ugly man clothes and get you into a bath."
She left me for an attached bathroom. Soon came the sound of running
water. Then would have been the time to flee but I remained as if tied to
the floor. The feminity of the room was overwhelming, and the thought
that I would soon be wearing girl stuff was making me hard.
Mistress Cindy returned. "Did I tell you to take off your clothes! Do
you need to be spanked?"
Helpless to resist, I pulled off my shirt. When I stripped off my jeans,
my hard-on was there for your to see that I was turned on by this.
"Don't worry dear. That was bound to happen. Wait until you get into
lingerie."
I swallowed, thinking about wearing panties and a bra.
She had a wonderfully scented bath ready for me. "Did you shave already?"
Yes, I nodded, embarrassed. "I don't have much hair naturally."
"I think today you're going play being my niece. You look way too sweet
and young to be a woman."
The bath was wonderful and calmed me down. I could feel myself slipping
away into this fantasy of being a young girl.
Cindy left me a pair of shiny purple panties, with pink butterflies.
Oddly, they were lined with soft plastic. When I slid them on the
erection, I lost in the bath returned. Good thing I'm small down there.
"Come on, let's get Amanda dressed," she called from the other room.
Okay, I took a deep breath, you're going to walk out and have someone see
you wearing panties.
"Those look fantastic on you," she cried when I stepped out of the
bathroom. "But that is going to continue to be a problem," she said
pointing down at my little member tenting the panties.
"Why are these lined in plastic?" I asked.
"Because little sissies like you can't control themselves and we don't
want you ruining your dress."
A shiver ran down my spine just hearing her say, my dress.
"Pull down your panties for a second, and we can take care of your
problem."
She put on a rubber glove, and in only two strokes I came.
"The rule in this house is everyone cleans up their mess. "Looks like
someone is excited to be a sissy."
She lifts her glove to my mouth. It was full of my white semen.
"I can't."
"Of course you can, all us ladies have to swallow cum. If you don't this
is all over, and you can never return."
Now I've spent many nights watching porn, fantasizing about giving
blowjobs and having cum shot into my mouth, but now that I was on edge, I
didn't know. I didn't want to leave. Change that; I couldn't go without
seeing what it is like to be a girl. In the end, I lapped up my cum.
Surprisingly, I don't get sick about the whole thing, and the taste
doesn't make me gag.
"Now, that you've settled down some, let's get you all ready to go out
with me."
What is she talking about. I am no way ready to go out in public as a
girl. She reads my mind.
"Don't worry sweetie, when we are done no one will know you are not a
girl. Besides, you are so soft looking already; it is not a challenge.
First, let's do your chest. " Mistress Cindy has me sit down in front of
a huge mirror like you see on Hollywood sets. The chair is a leather
white kind you see in beauty shops.
"I think these small ones will do since you are only fourteen." She comes
around with two life-like breasts. I just watch in a trance as she smears
glue onto my real chest and sticks on the new boobs. When she finished,
they look real. I can hardly breathe.
"You are so fucking cute," she said. "I knew it the first time I saw you.
Inside you have a sissy wanting to come out, and today we are unleashing
her. Can you feel the transformation?
Something was stirring inside me, for the first time in forever I felt
good. A tinkling sensation on my skin and my mind seem to be floating,
happy to let her guide me.
Over my new perky breast, she showed me how to put on a lacy purple bra.
The bra felt so right; the straps on the shoulders, thickness under my
breast, which pulled down a little on the cups.
"Move a bit so you can feel what it is like to have boobs."
I did, and the glue held then firm to me, but they did have a realistic
weight.
Mistress Cindy smiled at me in the mirror. "We need to do a little makeup
but not so much. Your skin is almost flawless. Now relax and let me make
the last of maleness disappear, not that there is so much, honey."
She was an artist. When she finished, I no longer worried about passing
outside in the world. My blue eyes looked so big and fantastic, with
light purple eyelids and dark liner. "This is a little much for your age,
but we're going to the ballet after all."
"The ballet?"
"You'll love it. A special girls night. Dinner, ballet and all dressed
up. I made a call this morning to get great tickets." She winked at me.
"I have connections."
"Why are you doing this all for me?"
She took my chin in her hand and looked me in the eyes. "You do not know
it yet, but you're very special. We'll talk over dinner. I think we can
make a lot of money."
My head spun. What am I getting into with her? No, all this free
attention has been a seductive web. I should say enough, but I have no
willpower. She was in complete control and knew it. I remained silent,
as she went for my dress.
"This cocktail dress will be perfect. You'll look divine, and it will
show off those legs."
Any hope of resistance disappeared with seeing the dress. Sleeveless, it
was made of chiffon, although my knowledge at that time was so limited I
had no idea of the material. To me, it was a fantastic material, and I
loved the ruffles on the end trim of the skirt.
"Are you ready, to be Amanda."
I said yes in my best girl's voice. My soft voice had always been an
embarrassment to me, but then and now, it is a gift. I sound like a girl
without trying.
The dress zipped up the side, and the hem was above mid thigh. When she
pulled up the zipper, it was like a red line was passed, and there was no
going back in my mind. I want nothing more than to go out in public as a
girl in the purple dress.
"Pantyhose are not in right now, but your dress is too short for thigh
highs. I just love the way nude hose look and feel."
Mistress Cindy showed me how to roll the legs of the hose and slide them
up my smooth legs. She was right. It felt divine.
The rest of the getting ready was a blur, but I recall when I stepped in
from the full-length mirror after she finished, I was no longer Tony. I
was Amanda. Mesmerized, I saw no hint that I was a man dressed as a young
girl. My legs looked so smooth and perfectly shaped under the pantyhose.
I barely noticed the pantyhose, they just felt like a whisper on my skin.
She had done such a fantastic job on my hair; I never wanted to go back to
wearing it as a boy.
"We need to pierce your ears to make it complete," Mistress Cindy said.
I'm stunned. Is she serious? Piercing my ears is a permanent step I'm
not sure I want to take.
"Don't be dramatic. Lots of men your age have pierced ears. It's not
that big deal. I am good at it."
She didn't wait for me to decide and for dressed as a girl, I had lost any
will to decide on my own. It was like Mistress Cindy was my mother or old
sister. She decided my ears needed to pierced, and they got pierced.
It did hurt, and I almost cried like a little girl. Something was
happening in my subconscious. My old self-faded and the piercing of my
ears pushed it to where I almost forgot to be a male.
She gave me a cute little sweater to wear over the dress. It was short
and fuzzy, only going do a little under my arms, way above my waist.
"Before we go you should practice peeing in a dress. I also want you to
put this up your back pussy." She held out a tampon. "It will make you
feel more like a girl and also make sure no accidents happen."
My hand shook as I took the plastic wrapped tampon from her.
"You are such a baby," she said. "Mommy will help you."
She led me into the bathroom and explained how to pull up my dress and be
careful with my pantyhose. "Maybe I should just put you in a diaper for
today," she said, smiling. "For the tampon, we just pull of rip off the
plastic wrapper. The tampon is inside this plastic applicator." She
dipped the head of it into a jar of gasoline. "Now, bend over. All you
do is slide the applicator into you bun hole and then push in the back of
the applicator, and the tampon will slide out."
I felt totally violated when she pushed in the tampon.
"Now you have a string hanging out to pull and remove it later."
The tampon didn't hurt, but I knew it was there and she was correct, it
did make me feel more like a girl. It would be so odd, walking around
people, none of them know I am a boy with a tampon in my rear.
I carefully pulled up my panties and hose, brushed down my dress. Women
would not understand this, but after wearing heavy men's clothes for a
lifetime, it felt odd and free to be wearing a light, flowing dress.
Having your legs bare and knowing people could see your panties if you
don't sit correctly feels liberating and scary. The anticipation of going
out as a girl made me almost pass out.
Hopefully, I can capture in print all the emotions and feelings from that
first night as a girl. For the first time, I felt lucky to have my little
girl body. Little things, like sitting in the car with my legs together,
my almost bare legs coming out from my short dress, were breathtaking.
Eating at the sheek restaurant, my legs crossed under the table, taking
small delegate bites was heavenly. Then, I experienced being looked at by
teenage and older men, and I can still recall the thrill I felt down
below. Not in my penis as I expected, but in my backdoor as it hugged the
tampon. While I watched the ballet, my hole pulsated, mainly because I
couldn't help staring at the men ballet dancers with their packages on
display in tights. I kept fantasizing about wearing tights and being bent
over a table, to be fucked by a man as I moaned and squealed. My dreaming
moved to being fucked from behind while another dancer filled my mouth.
Never had I had fantasies about being with a man, it undoubtedly was the
clothes releasing my trapped feelings. Mistress Cindy kept glancing over
at me and smiling, surely knowing what I was going through that night.
I never wanted that night to end. Being dressed and completed accepted as
a girl in public rewired my brain permanently. The thought of going back
to her place and changing back to being a boy depressed me on the return
drive.
"You really should be a sissy," she said to me.
"I never knew who much I would enjoy being a girl."
"Oh," she corrected me, "I said sissy, not a girl. You don't have a real
pussy so you can never be a girl, but a sissy is so much more fun. You
can't stop thinking about men dominating you, can you?"
I lowered my head, a bit ashamed of my uncontrollable urge to be a sissy.
"I don't want to go back to being a boy."
"Boy clothes do suck, don't they? I'm sorry, but I do run a business."
She pulled into her driveway. This can be your only free session."
We held hands on the way back into the house. "I'll tell you what. You
can stay as Amanda. Keep the dress and clothes. I'll even give you a
pretty nightie to take home for bed."
My mind raced. Driving home dressed as a girl, could I do that? Since
it's late, getting into my apartment without being noticed should be easy.
"That would be wonderful."
She led me into the same room as before. "I'll need for you to bring back
the breast forms. Don't let forget to give you the adhesive removal."
The thought of going home dressed as a girl revived my excitement
downstairs. I felt myself growing hard under the panty and hose.
"Do you work tomorrow?"
"I don't have a job."
"Listen, I'll give you a few old clothes so you can extend your girl time.
The adhesive on the breast is good for a few days. " She started putting
clothes in a huge Victoria Secret shopping bag. "I'll even put in some
makeup so you can practice."
My heart was beating fast. "But, I can't pay for this."
"On the house sweetheart. You're just too pretty for boy clothes. Save
your money. Maybe we can go on another girl's night in the future." She
hands me the bag. "You want to be a girl, don't you?
I looked down at my feet in the black Mary Jane shoes. My smooth legs are
looking so good. "I don't know. This is coming so fast."
"Listen to Mistress Cindy. You're meant to be a sissy. Men would love to
take care of you."
One would think, a man being called a sissy would be devastating, but it
made me feel good. Also, men finding me attractive was nice.
Mistress Cindy seemed to be in a hurry for me to leave, I got the car
keys from my packed jeans, I didn't pull out my wallet, something I would
regret a few minutes later.
It felt weird, getting in my car wearing a dress. Something you don't
think about as a man, but in a dress, a girl always needs to be aware of
how they are sitting and having her knees together. Wearing heels and
pressing the gas and the breaks was also a wild sensation.
I should have gone straight home, but going through a drive-thru for junk
food sounded really exciting being a girl. What I wasn't thinking about
is Mistress Cindy had made me look under sixteen, not old enough to be
driving.
My heart races as I pulled up to the window and catch the guy glancing
down at my legs. He starts flirting.
"Late for someone as young and hot as you to be out."
"Coming back from a party," I said, sounding pretty good in my girl's
voice. Finally, my soft fem voice is an advantage. Then, I recall my
wallet and money is in my jeans in the Victoria Secret bag on the back
seat. Frantically I search in the door storage area and find the spare
money I keep for emergencies. Thank god, I barely have enough to money
for the food.
On the way out of the parking lot, I passed a cop. No way am I going to
speed or break any laws. I have no idea what would happen if I was pulled
over looking like this.
I didn't get far down the road before I see the police car behind me. He
flicked on his lights, and I almost passed out. Why the hell didn't I go
straight home?
Nothing to do but pull over and try not to die of embarrassment. It
seemed like forever before he came to the window. The cop was huge and a
lot older than me. I was almost shaking with fear.
"You look a little young to be driving, and this car doesn't belong to
you. Let's see your license."
"What did I do wrong?"
"Nothing yet."
"My license is my wallet in the back seat."
"In the bag?"
I wished to be anywhere but in my car that night. When do I tell him I am
not a girl? Is there a law against dressing as a girl? Maybe I can tell
him I was at a costume party.
"Come on out and get it."
I climb out of the car, trying to keep my hem from rising my thighs. He
was not trying to look, probably because he thought at the time I was a
teenager. That would change very soon. When I showed him my license, he
looked at it for a long time. My heart was almost jumping from my chest.
"Is this you?"
I nodded my head. "I can explain."
"And you are twenty-two?"
I nodded.
"This is your lucky night. I'm going to give you a chance not to be taken
to the station. The boys in the cells would have a great time with you."
I started to cry.
"You're going to get your car and follow me. Don't try to drive off."
"What are you going to do?"
"Do you want to be arrested?"
"No."
"Then all you have to do is make me happy. Let's go."
I couldn't believe this was happening to me. I wasn't ready for this at
all, I was just getting used to dressing as a girl. Fear overwhelmed me
as I followed his car down the road and into a large dark parking lot. He
stopped alongside a steel building that looks like a vacant warehouse.
He knocked on the window. "Come on out."
I feel so little and helpless in my dress, standing in front of the fully
dressed, police officer.
"Turn around."
I turned and he pulled my arms behind my back and cuffed me. "This is for
both of our safety. Can't have you pulling out my gun while you are
servicing the gun in my pants."
"Don't make me do this," I whimpered, not caring now how pathetic of a man
he must think of me.
"No one is making you do anything. Your choice. This or jail?"
I look down at my feet, feeling so helpless with my wrist cuffed behind my
back.
"You're dressed so pretty, what did you expect? I was completely fooled.
You're better looking than most real women. Your legs are super hot." He
lifted my face up by the chin, so I was look up into his eyes. "Now ask
to suck my dick?"
I gulped. "May I suck your dick?"
Saying those words out loud in my girl's voice is like watching someone
else, not me. The male me retreats, and I become a woman, which makes
this easier than thinking I'm a man about to swallow his dick.
He got something out of the trunk of his car. It was a thick blanket he
puts down on the ground.
"Come on. I know you have done this before."
I shake my head.
"Wow." He pushed me down on my knees. "Now it is my lucky night. I get
to train you."
On my knees, I stared at the crotch of his blue uniform pants, thinking
about his penis hidden inside. I've never seen one except my own and on
porn sites. As he unzips his pants, my stomach swarms in butterflies. I
was so scared that I felt like I'm going to pee myself.
Thankfully it isn't a huge dick like on the porn clips I've watched, but
it's still bigger than mine. He holds it out to me, stroking it a few
times to get completely hard.
"Take it slowly into that mouth making sure you use all lips, no teeth.
Go as far as you can without gagging."
He stepped closerto me. I had to kneel up straight to get my mouth at the
right level. Waves of hopelessness washed over me as my hands shook in
the handcuffs. I felt tears run down my cheeks.
"Look up at me as you suck."
I looked up at the cop and puff out my lips to hide teeth. Our eyes meet
as I take in the head of his penis. It's way softer that I expected. And
hot, the thing is on fire from the blood making it stiff. He moans as I
move my tongue around the tip, feeling the slit.
It's more than unnerving not having your hands for balance. I felt as if I
might tumble forward.. He sensed this and started slowly pushing in his
cock and filling my mouth. I don't know if I can explain all the feelings
going through my body as I knelt there, hands cuffed behind my back,
employed to his cock. Weird electricity flowed in my pantied little
prick, flowing around into my asshole. My head felt numb. Everything to
be focused on my mouth.
He kept pushing and unbelievably, I took the entire length without
gagging, my nose up against his pants.
"Holy shit, this is great. Don't move. I need to settle down, or I'm
going to come already."
So I remained with his dick almost down my throat, not moving, looking up
at him. I could tell he was fighting to keep control will I tried to get
used to the idea that I was now a cocksucker.
"Okay, start moving up and down my shaft."
I obeyed, looking up at him, totally submissive, moving back and forth on
his shaft, my soft lips were driving him wild. He was breathing hard, and
his cock began to throb.
"When I come, you have to swallow it all. I can't get any on my uniform."
He said this is spurts because he was breathing so hard.
After only four trips up and down his shaft, he pushed himself down my
throat and began to cum, filling my mouth with his warm stuff. I wanted
to pull back, but his hands kept me impaled. Cum coated my tongue and
flowed down my throat. At that same moment, I had an orgasm in my
panties, which luckily were lined in plastic.
For a few moments, neither of us moved, trying to catch our breaths, me
only able to draw air through my nose since my mouth was full of cock and
cum. Overwhelming humiliation flooded my mind. I felt as if I had
crossed a line that can never be backtracked.
He pulled out and held out his dick for me to clean. Like a little slut,
I worked my tongue making sure all his cum was inside me. To finish off
the humiliation, he made me blow dry it before he slid it into hiss pants.
"Stand up and turn," he commanded.
I did, and he removed the handcuffs.
"Do you live alone?" he asked
I nodded, too embarrassed to speak.
"I have your address and phone number. You were fantastic I'll call you
sometime and drop in, maybe a repeat performance. You'll dress pretty for
me."
Oh shit, this wasn't good at all. I had done it all that night without
thinking to be a girl long term.
"Payback, having a friend who's a cop. Your place will always be safe.
In fact, it's late; I'll follow you home to make sure you get to it
safely."
I went to my car, his taste strong in my mouth. What a switch after I
blew him, now he's talking to me nicely. He followed me home and flashed
his lights as I go in the apartment building. I had hurried to my place
before anyone saw me.
Inside I flopped on my couch, face down, crying, which was so weird. I
never cried before today. Since I first put on a dress, the waterworks
turn on easily. I don't know how long I cried, but finally, I drifted off
to sleep.
Sometime in the night I woke up and had to pee. Since I was still in my
dress and pantyhose, I sat on the toilet. Afterward, I looked in the
Victoria Secrets bag to see what Mistress Cindy packed. Besides several
skirts, there was a makeup kit and night clothes.
The nightie was very juvenile with a light pink top with pink ballerinas.
It had three buttons on the back, and the sleeves were puffy. They came
with a matching pair of full panties, lines in soft plastic. The butt had
three rows of ruffles.
I sat the nightie on the end of my bed, willing myself to change into my
boy clothes and forget this day ever happened. Nothing was stopping me
from going back to my life without dresses. Only my pierced ears were any
physical sign of my experience. No one but the cop knew about me sucking
a dick. Since I'm graduated and unemployed, I can move out of this city
and go back to my old life, be it, lonely.
I went into my bedroom and took off my dress and stuff, but couldn't find
the adhesive remover in the bag. Not good, Mistress Cindy forgot. I
tried to pull them off, but they were on tight, and I became afraid of
pulling off my skin. I was stuck with these boobs for at least tonight.
I'd have to call her in the morning.
That pushed my decision I might as well wear the little girl nightie to
bed since I had boobs. I slid the nightgown over my head and reached back
to button up the back. The material was shiny and soft satin. It felt
wonderful against my skin. The panties were tight around the legs and
waist, but bubbled out large, as if it was made to cover thick diapers.
Since I was a little kid, I have had a fascination with the possibility of
wearing diapers. Putting these on sent me backward in time. As weird as
it sounded to me at the time, I wished she had packed a diaper.
I crawled into bed and fell sound asleep, one of my best sleep in forever.
I did wake up once in the night but went right back to sleep after I
played with myself through the panties, cumming safely in the plastic
lining. I will admit, I fantasized about blowing the police officer.
All night my dreams were being caught dressed as a girl. I was back home
with my parents, dressed as a little girl wearing a super thick diaper.
They didn't seem to notice or care.
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