New Little Sissy free porn video

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"I'm done planting the flowers Mrs. Grant," I said.

"Justin honey, I swear I have no idea why you keep coming over to do
chores around here."

"I am rich you know just like your Mother, I do have a gardener."

"There's no need for you to do these things."

"Not that I mind paying you, but you certainly can't need the money
either."

"I just like coming over here Mrs. Grant."

She appraised him slowly now, was this a little slip, or was she just
imagining things? Was he actually saying he was attracted to her? No that
was silly, he was only 18 and she was 48, but his constant daily visits
she wrote off to lonesomeness. His Mother was a divorcee jet-setter and
in spite of his age she left him home alone often with a servant around.
So he came over after school doing small chores for her. Recently his
visits had extended to the weekends also. "Don't you have anything better
to do darling, friends or whatever."

He shyly hung his head and said, "They don't like me at school and I
really don't have any close friends."

"Why is that dear?" He hesitated and then decided she was nice and would
understand. "They call me a sissy and a fairy and they won't talk to me
other than to beat me up."

"Oh dear, I see."

"Well that's a sad explanation dear, but I understand, boys can sometimes
be very mean."

"Yea, I hate going there, I only do it because I have to."

"But why come here darling?" Again he hesitated but decided to press
forward any way certainly she wasn't going to beat him up and she was
reacting nicely.

"Well you're very nice to me and you're very beautiful too."

"Beautiful?"

"Darling how very sweet of you to say that but I'm just and old divorcee
not unlike your Mother."

"I'm surprised you think I'm beautiful."

"Yes, at least I think you are," I replied. "Now she thought she really
understood, he truly was a sissy he just didn't know it yet. But there
were many kinds of sissies, she'd have to feel him out to see where his
head was at.

"Come darling Justin, let's get something to drink and make ourselves
comfortable in the den in the nice air conditioning it's far too hot
outside. Once he was settled on the sofa with his Coke and ice she slowly
started to question him. "Darling if I ask you some questions will you
tell me the absolute truth?"

"Sure," he replied. "No I mean it darling it must be the absolute truth,
pulling no punches, good or bad."

"You must say what's truly in your mind alright?"

"All right, sure I trust you Mrs. Grant."

"Alright darling here we go, no cheating now."

"Why do you think I'm beautiful Justin?"

"Well you know, all the lady things, your makeup, perfume, clothes,
everything, your just very ladylike and pretty."

"I see, so you like my makeup, hairdos and clothes."

"Sure they're pretty."

"But surely there are girls at school that are pretty too."

"No they're just as nasty as the boys, sometimes even worse."

"And they look nothing like you."

"Well I am quite a bit older that's why sweetie."

"Well if that's the case then I think I prefer older."

"Darling I hate to tell you this, but we are good friends."

"Well, you really are a sissy."

"No," he quickly replied. "Yes, you are darling, now when I say it, it's
not like the boys at school."

"I'm just telling you that you like certain girlish feminine things."

"Which is perfectly all right with me." Well at least she wasn't yelling
or carrying on like most adults, we was very calm and still smiling
brightly so he decided to go alone with her. "Suppose what you said is
true, would you still like me and want me to come over?"

"Of course I would darling, in fact I'd probably like you even more."

"Really?"

"Yes, I believe I would."

"Can I ask you some specific questions darling, promise to tell the
truth?"

"Yes I promise."

"Well I do wear a lot of makeup, trying to hide my age."

"Do you like my makeup?"

"Yes I do Mrs. Grant, it makes you look, well very sexy and glamorous
like a movie star or actress."

"And you like my bouffant hairdos?"

"Yes I do they're very beautiful."
Well it was very clear now she had a full blown sissy on her hands, there
was no denying it any longer, he had every sign.

"Tell me darling, the truth now, have you ever wished you liked like me?"

"No," he said much to quickly trying to hide it. "Darling I thought we
agree to be honest with one another?"

"Well, I mean, OK, yes the thought has passed my mind a time or two." She
smiled just she thought. "Tell me sweetie, when you picture this in your
mind do you look exactly like me or just like a young girl?"

"Well, I sort of picture myself just like you."

Well there you have it then, I understand perfectly."

"I could of course make you look like me, if you wanted but you would
have to keep it to yourself completely, never tell anyone."
"Oh Mrs. Grant, be serious, I mean I fantasize about it but how could I
ever actually look like you?"

"You're a beautiful woman and I'm just a k**."

"Well darling the things that 'Make' me a beautiful woman are all
superficial."

"Makeup, dresses, nylons, bras, high heels, etc. are all just things you
wear."

"Anyone could wear them if they wanted."

"And you'd be surprised how much makeup can change the way you look."

"Are you saying you'd actually do this," I asked? "Yes, if you wanted me
to darling."

"Only two rules, you never tell anyone else, ever and there are no half
way measures you either want to look like me or you don't."

"This is not something you just play around with."

"I don't want you backing out if you think it's not going exactly the way
you planned."

"And you must obey me, at all times and learn from what I tell you."

"I'm an adult and I know about many more things about this than you can
possibly imagine."

"Do you agree."

"All right, I agree, and you won't tell anyone either?"

"No darling this will be our little secret."

"Your Mother is still away?"

"Yes she'll be gone another two weeks I think, the chauffeur takes me
anywhere I want to go if I need to go somewhere, and the maid cleans the
house."

"My Mother left me plenty of money, and I have a credit card to use too."

"Well give the chauffeur the weekend off and tell him you won't be going
anywhere this weekend."

"The maid can stay at your house as long as she knows your spending the
weekend with me."

"So no problem there."

"Saturday afternoon we'll do our thing darling."

"Couldn't we do something tonight?"

"No sweetie, I have to shop for some special things I'm going to need for
you."

"Tomorrow will be soon enough."

"Go home now, and dream lovely sissy thoughts and tomorrow at this time
you will look like me, I promise."

She purchased all the things she felt she might need to feminize this
young boy and turn him into a truer homosexual sissy faggot. He seemed to
want it very badly and she was going to accommodate him. Of course she
herself would have to look intensely wicked the next day when he showed
up because she had to set a good example for him.

The next day he arrived right on time and when she opened the door he
nearly passed out in awe. She was dressed in a black chiffon blouse that
showed her ample bosom encased in a black bullet brad underneath. Her
skirt was skin-tight and also back, a hobble skirt although Justin didn't
know that it was called that he just knew it looked fabulous on her and
sexy as hell. Her makeup was the heaviest he'd ever seen. She had big
long thick false eyelashes on and tons of dark eye makeup, crimson red
lipstick and long red scarlet nails. It was the most stunning display of
glamorous femininity he's ever seen or hoped to see.

"Up to the bedroom with you sissy boy it's time to be feminized." He
followed her to the bedroom and was ordered to remove all his clothes,
everything. Fortunately being so young he had no hair, but she shaved his
pubic area and plucked his thin brows anyway. The rest of his minimal
brows she'd cover with foundation later.

"Well darling let's begin, first off your clothes if your going to be a
lady and not a boy we need a new name for you."

"I've decided on Jessica." He made no reply just nodded his head still in
awe of how sexy she looked. "Next I think calling me Mrs. Grant is a
little formal for the intimate things we're doing here, so why don't you
just think of me as 'Mommy' and call me that for our little game,
alright?"

"Yes alright," he replied, then added hesitantly, "Mommy."

Do you know what this is Jessica," she held out a waist nipper type
corset? "A girdle for a woman?"

"Well actually it called a corset darling, this one is it black with red
trim."

"Do you know the purpose of this lady's garment?"

"I think to make your waist look smaller."

"Exactly dear, and while this might be a little uncomfortable for a young
inexperienced boy it's necessary to get you looking like me."

She began lacing him into the corset. She didn't want to scare him off
the first time, but she managed to take him down 4" inches before he was
whining about it crushing him. Next she added a black bra with 44DD
breast forms that she's purchased yesterday at great expense. These were
not the cheap kind but very expensive and weighed to simulate breasts of
this size. They felt so heavy on his chest never having felt this feeling
before, but he loved the sensation of wearing a bra.

Next she produced sheer black nylons and slid them up his smooth young
hairless legs. He loved the sensational feel of the smooth sheer nylon
caressing his skin. He was beginning to like this process a lot even if
she did call him a sissy. "Now we have something completely special for a
girl like you darling, they're called sissy display panties." The sexiest
lace and bows in black and red just like your corset and bra because
women are always color coordinated darling." These are very special
panties made just for sissies like you."

She held them up and showed him the little hole in the front of the
panties for his penis to fit through. She slid them up his hips and up to
his waist pulling his hard erect penis through the little opening. It now
stuck out dramatically through the ruffled lacy hole on display. She was
as excited as he was at this sight. "Now you are beginning to look like a
proper sissy."

"Please Mrs. Grant, ah, Mommy do you have to call a sissy, it sounds so
homosexual." Yes darling we do have to call you a sissy because that's
what you are."

"And yes it is very homosexual, because that's what you are too."

"No Mommy, I swear I never did anything homosexual before." She smiled
that wicked evil smile and in her current makeup and clothes that look
was downright scary. "Not yet darling, but you will, oh yes you will,
many, many homosexual things." He trembled at the sight of her, but dared
not answer back. Basically she was in control now and he'd asked for this
hadn't he? Besides he certainly couldn't leave dressed like this and his
other clothes seemed to have magically disappeared.

"Come along little sissy boy, it's time for lots of feminine makeup." To
his surprise she grabbed him by his hard cock with her long red nails and
lead him over to the lighted makeup table. "Just the brief period of her
red nails wrapped around his penis made him even harder if that was
possible. The thrill was intense and he'd do anything to feel it again.
"Well darling first of all to look older your going to need lady's
foundation makeup, I'd say several layers to give you a very made up look
and hide your youth."

She started applying layer after layer of liquid foundation makeup to his
face. She paused in between each layer allowing it to dry before redoing
his face again. After several layers she powdered everything with a big
fluffy brush. He loved the feel of that brush so soft and the powder
smelled so good. She noticed him enjoying the smell of the powder. "Yes
darling, you love the smell of lady's powder don't you?" She placed a big
helping on the brush and then held it under his nose. "Yes my little
sissy faggot breath in that lovely feminine smell." She touched the tip
of the brush to his nostrils. He froze, trying not to breath it in. "I
said, breath it in you little sissy, or I will punish you right here and
now."

Let with no choice, he breathed in the lady's powder and it permeated his
senses. He was intoxicating, it seemed to capture his mind in its grasp.
"Yes lovely is it precious the smell of a lady wearing makeup darling."
With his small plucked eyebrows now covered by several layers of
foundation she was free to pencil in his new eyebrows. Black tapered and
much higher and severely arched like a very sexy and glamorous older
woman. She took her time making them perfect because the new eyebrows
would be the most expressive and erotically feminine portion of his new
older woman look.

He tried to see what she had done it felt so strange, but she lightly
slapped his face. "No looking darling until Mommy is all done and you see
the new you." Now she started on the eyeshadows. First a very dark gray
almost black, then lavender above then and finally white shadow
underneath his new ultra feminine eyebrows. She worked hard blending them
and shaping them to be perfectly made up. "Now one of the most feminine
things of all darling."

"I bought a dozen pair yesterday just for you."

She produced a pair of very long thick lady's false eyelashes. She placed
some white type glue on them and then carefully glued them into place on
his lids. When she was finally satisfied that the glue had dried so told
him to open his eyes. The weight of them felt so heavy, and even stranger
for the first time in his life he could see his own eyelashes because
they were so long and thick. He immediately liked the feel and weight of
them. They made him feel so feminine and girlish.

She only paused long enough to make sure they were in place and tightly
secured before moving on to the black liquid eyeliner. His eyes were
painted and thoroughly outlined in deep black. Such a sexy little sissy
whore he made now, a lovely painted lady. She was so hot she wanted to
play with her pussy but she dare not, not yet anyway. Bright red blusher
was added to his cheeks and finally the most feminine of all things was
coming.

"Time for Mommy to put some very ladylike lipstick on you darling."

"But first let's enlarge those luscious girlie lips with some lipliner
making them bigger." She outlined his lips with some kind of pencil that
looked like it was a dark purple almost black. He could tell from where
she was drawing that his lips would be bigger, much bigger than his own
true lips. "Now for your first lady's lipstick sweetie."

"Get used to it because you're going to be wearing it a lot of the time
in the future."

She applied several coating of the deep crimson red lipstick to his lips
until she was satisfied and then she surveyed her work. He was a true
painted slut now, and it excited her, and better yet she knew it excited
him too. She sprayed him all over with her Chanel No. 5 perfume until he
was enveloped in a cloud of sweet feminine smells. "This is too good to
pass up darling, let Mommy get some pictures of you." She added huge
massive dangling rhinestone earrings to his eyes but reminded him not to
look in the mirror yet.

She produced a Nikon digital camera and began to take pictures of his
made up face. He looked so bizarre with his short boyish hair and that
heavily made up face and those big earrings. God he looked so sexy and
wicked like that, but not half as wicked as she felt doing it to him. She
was really getting off on this. She took dozens of pictures on his face
from every angle to make sure she showed every detail and those
incredible lashes. Then she took some more pictures at a longer length
showing his corset, bra, nylons and of course those sexy sissy panties
with his penis sticking out.

Even like this it was hard to tell how young he was anymore. He looked
like a boy all made up all right, but you could no longer know he was
only a 18 years old boy. "Well enough of that you can't hang around in
your bra and corset all day."

"Let's get you dressed like a lady now." The sheer dark violet nylon
blouse she placed him in did nothing to hide his black bra underneath,
but God did it feel wonderful sliding over his smooth young body. He felt
glorious wearing it. A skin-tight black leather mid-calf skirt followed
very, very tight and it pressing his sissy cock against the slippery
satin lining of the skirt creating a little bulge in the front.

He of course was too young to understand the sexual significance of this,
but she certainly did and was excited anew. She added a very wide black
Patten leather belt around his waist pulling him in more tightly even
then the corset. He was so concerned with the tightness that he never
even noticed the big rhinestone buckle in the front that secured the belt
around his now tiny waist.

She led him back to the makeup table where she planned to add the final
feminizing things. Next up was long red nails glued to his fingers. These
nails were already painted a deep red so she simply glued the glamour
nails onto his fingers. Now he had 2" inch long red nails, and of course
he complained it was difficult to touch anything and they were hard to
get used to. She reminded him this was how and older woman looked and to
stop complaining this is what he wanted.

Now for his crowning glory, the wig she had purchased. It was a very
light blonde, but not quite platinum blonde. It was of course immense. It
was actually two wigs together. The fitted wig was a big teased bouffant,
and the wiglet that sat on top of it was lots of banana curls in the same
blonde color so it look like all one. It was a massive ultra feminine
updo that any drag queen would approve of. He looked sensational in it
and she felt rushed now to finish him off.

She added several big jangly bracelets to each wrist and a huge massive
rhinestone necklace around his waist. She even added a shiny rhinestone
ankle bracelet around his foot. She added 5" spike high heel pumps to his
feet and strapped them on. She wished she could use 6" inch spikes, but
she knew he's never be able to stand in them yet. So while she was
disappointed she did have to face reality. No doubt even these combined
with the tight leather hobble skirt would cause him enough problems. She
helped him up and led the wobbling boy over to the full-length mirror.

"Meet the new lady in town darling, Mrs. Jessica Grant."

"Now just like me, Mrs. Veronica Grant." She wrapped a white ermine wrap
around his shoulder and stepped back to show him the lady he'd become. It
was incredible she'd actually done it, he looked like a 40 + woman, a
very glamorous and sexy woman at that. The makeup was stunningly
beautiful and he felt so glamorous and sexy wearing it. The jewelry was
dazzling and very ultra feminine. The earrings were beginning to hurt his
ears a little but he really didn't care about that anymore.

"Do you like darling?"

"Oh God, yes, it's incredible, I look just like a sexy woman, I never
believed I could, I thought I'd look silly."

"Nonsense darling, you're gorgeous and I know some homosexual men that
would go gaga over you sweetie." There was that homosexual reference
again he thought. But truly he was dressed like a woman now, and all made
up too, perhaps she was right because the thought of some man fawning all
over him made his cock bulge out even more. He wanted to look in the
mirror to check if the bulge was visible and that's when he actually
looked at his wide patton leather belt in the mirror. "Oh My God," he
said.

She laughed, "Yes darling I see you've finally noticed the belt."

"It says 'Slut' spelled out in diamonds," he said. "Yes Jessica, well
actually rhinestones darling, but yes it proclaims you to be a total
slut."

"Do you like it?"

"Yes Mommy, I do."

"You can't see your ankle bracelet because of your skirt and the high
heels but that also says 'Cunt' in rhinestones too darling."

"No, no, don't try to raise your foot honey, in those high heels you'll
fall over."

"Are you pleased with my work?"

"Oh yes Mommy, I look wonderful and I feel so sexy, it's divine." She
took hundreds of pictures of him posed and posing in various feminine
ways and he was having a ball, he loved being a lady and acting like a
super model, and she loved watching him. "Well now darling, I know being
so young you haven't given much thought to this, but now that you've
achieved your goal of looking like a lady have you given any thought to
what you like to do with the cloned Mrs. Grant."

Actually this surprised him, she was right, he'd never given it any
thought, other than he wished he looked like her and he'd certainly like
to kiss her and maybe feel her large breasts. He giggled mentally at the
thought because now she could feel his too. "Well do you trust me
darling, I mean will you obey me and trust me when I tell you, you will
learn to love this?"

"Yes, Mommy, I do trust you completely."

"Even if it hurts just a wee bit?"

"Yes, I guess so."

"No, darling, no guess, you must say you trust me completely and you will
obey me no matter what."

"All right, I will obey you."

"Good then let me make a phone call and I'll be right back." She helped
him wobble over to a chair to sit. "Just relax darling, I'll only be a
minute."

"Look at your pretty makeup, hairdo and jewelry in the mirror while I'm
gone and perhaps practice a little in those lady's high heels dear, but
be careful, being a lady isn't always easy." She went off to make her
call. Actually she'd planned this all alone, but she wasn't sure the boy
would go through with it so she'd held off the call until he was actually
fully dressed.

"Yes Ron, she's ready and waiting come on over, just remember our
agreement."

"You obey me completely, and you leave when I tell you to leave and I
guarantee you a real good time. Her friend Ron was homosexual and had a
thing for drag queens too. He was perfect for the job and he'd agreed to
do as he was told for a great blowjob from a fabulous queen in return. Of
course he had no idea that the blowjob he'd be getting was from a 18 year
old boy, he was told it was some regular queen that Mrs. Grant knew.

She returned to the bedroom to find the little minx actually practicing
walking in the high heels. Well he certainly was serious about wanting to
be a woman. As she silently watched she realized he was actually getting
better already. He really was trying hard in spite of the hobble skirt
and the heels he was developing a good wiggle and swish to his walk. OK,
he was a little shaky at times, but he was getting better already.
"Enjoying yourself Mrs. Grant," she laughed as she entered. "I was just
practicing as you asked Mommy, it's very hard isn't it?"

"Yes dear, it is, it takes a while to walk how to walk in high heels
properly."

"Anyway, since you're all dressed up and made up darling, I thought there
was no sense wasting it."

"I've got a hot guy on the way over who would love for you to be his girl
and suck his cock."

"A guy, suck his cock, oh no please Mommy."

"Now dear I thought we agreed you are homosexual and you are a sissy."

"That's what sexy little sissy faggots do darling."

"You said you would obey me and trust me." He felt trapped completely but
he felt if he didn't do as she told him then she'd never dress him up
again like this and that was a thought he couldn't stand.

"I'm sorry Mommy, yes I did agree, and I'll so what you tell me."

"Good, now she need to make one addition before your hot stud gets here
for his blowjob." She helped him out of the belt and skirt and produced a
shiny pink butt plug. "Bend over little princess, time for you to take
some cock like a woman too."

"We must begin your training as a glamorous slut just like you belt
says." He made no further complaint, he trusted her and relaxed as she
told him and with a little effort the plug slide into his virgin ass.
"Just like a woman now darling with a cock inside you." She helped him
back on with the skirt and belt because with his new long red nails he
was all thumbs.

When Ron arrived he was stunned by the physical beauty on this new queen.
"And your name is darling?" Veronica interrupted, "Let's just call her
Mrs. Jessica Grant darling, and say we're sort of sisters."

"Ah, another Mrs. Grant, well Mrs. Grant, your as beautiful as sexy as
the original." He kissed the back of her jeweled hand when she held out a
nice limp wrist displaying her long red nails. "Thank you Ron," he
replied. Sensing no resistance he pulled her into his embrace and held
her a second and then kissed her. Oh, the feeling of kissing while
wearing lipstick was wonderful and no longer was he teased or laughed at
by silly little boys. Now he was desired by real men who lusted after
him. He liked this role much better.

"Caress his crotch right through his pants Jessica, see if he's excited
to see you." Jessica did as instructed and caressed the front of Ron's
pants with her long red nails and jeweled fingers and quickly discovered
that Ron did indeed have a rock hard cock under there. "I think he likes
you darling," Veronica giggled. "Ron she's ready for you, take off your
clothes and show her what you have for her," she said. Ron needed no
second invitation he quickly removed all his clothes. "Her too," Ron
said, "I want to see her in all her glory, because it's hard to believe
that a woman so beautiful is actually a man."

"Are you sure that's what you want Ron?"

"Oh yes Veronica I do," he replied.

She helped Jessica out of her skirt once again and when Ron saw the cute
sissy cock sticking out of the ruffled lacy hole in her fancy panties his
cock started to throb. "Kneel and kiss his cock Jessica," Veronica
instructed. Jessica now free of the confining skirt dropped to her knees
the hard male cock only and inch or two from her mouth. "Hold it with
your hand darling and kiss it." Jessica was a little hesitant but obeyed
and grasped Ron's hard male cock and kissed it leaving a lipstick mark on
his cockhead. "Go ahead girl you know what you have to do."

With a whimper and a small sigh Jessica slide the lovely male cock into
her waiting lipsticked mouth. It wasn't bad she though, very smooth and
warm, and the lipstick made it feel so good so she started to suck in
earnest now. It didn't take more than 5 minutes. The sight of beautiful
Jessica's made up face with those long lowered false eyelashes and those
red lips and long red nails soon had Jessica swallowing her first load of
male sperm. She moved her head to pull back but Veronica was there to
hold her head in place. Well her neck any way with her immense hairdo
there was no place to really grab her head.

"Well, well what a great job Jessica."

"Did I not promise you a great blowjob from a beautiful queen?"

"Oh indeed it was fabulous," Ron replied. "What club does she work at,
I'd like to see her show sometime," Ron asked? "Perhaps we'll talk of
that later Ron, but per our agreement, you've had you fun and now it's
time for a little girl talk."

"By the way Ron just between us," she asked, "How old do you think
Jessica is?"

"Oh I hate to guess women's ages," he said, "They get very mad if you
guess wrong. "No darling it's all right go ahead and guess."

"Well maybe 35 or 40," he said. She smiled, "Yes close darling, all right
run along now." She showed Ron to the door and then returned to the
bedroom. As soon as she shut it they both broke into laughter. Jessica
was the first to speak, "35 or 40, close, oh my God I really had him
convinced I was an older woman."

"Yes you did darling, I told you with the proper makeup and hairstyle and
clothes you'd look just like me."

"However it would not be wise to ever let Ron know your true age dear."

"He thinks you're a new local drag queen at one of the female
impersonator club, let him keep thinking that."

"Oh yes Mommy, I understand."

"Well now darling, Ron has gotten his jollies for the day and it's just
us girls now."

"I'll just bet somewhere in there you've dreamed of me doing the same
thing to you that you just did to Ron sweetie, haven't you?"

"I never dreamed I could be that lucky Mommy, but now that you mention it
yes, I'd certainly like that very much."

"Well sweetie, I will give you your fantasy, but Mommy first dear."

"In order for you to be a fully sissy you have to be fucked like a girl,
and that's Mommy's job tonight."

"If you submit to me darling then I promise you the prize will be yours."

"Yes Mommy, I trust you in everything, you made me feel wonderful so far,
I even enjoyed sucking Ron's cock."

"So I guess I am a homosexual now and I might as will finish it off."

"Yes darling, exactly, I'll be right back darling." She disappearing into
the bathroom for about 5 minutes and Jessica was left with instructions
to repair his makeup and redo his lipstick as best he could. Like all
these other feminine things he adored he took these instructions
seriously and tried very hard to do a good job on powdering his face
again and redoing his lipstick.

When Veronica returned from the bathroom she looked more wicked and evil
then ever because now protruding from her crotch was a life like looking
cock, which she called as woman's strap-on cock. "It's time for Mommy to
have her pleasure darling." Jessica was bent over a chair and her butt
plug removed. "And let's spice it up a little darling, Mommy loves a
simpering, whimpering little sissy." Veronica gave her a pink nylon scarf
to hold in her right hand and showed her how to hold it daintily between
her long red nails.

"Now darling, Mommy wants you to wave your scarf daintily up and down
from a nice limp wrist displaying your long red nails and your lovely
jeweled fingers."

"I want you to whimper and squeal like a little sissy girl for Mommy and
show me what a homosexual faggot you are."

"You may sob and squeal all you like, but no crying sweetie we don't want
to spoil your makeup."

"Are you ready to become a real woman and get fucked?"

"Yes Mommy, I love you." Veronica lubricated the strap-on and slowly
eased it into Jessica ass. The butt plug had served to stretch her out a
little bit so it actually went in quite easily.

Veronica started to fuck her little sissy virgin in the ass now. Just
like a girl now Jessica played her part very well for one so young and
inexperienced. She whimpered and squealed in a high pitch girlish voice
and daintily waved her pink nylon scarf up and down careful to keep her
wrist limp and her nails extended. "Oh Mommy, Oh Mommy. I'm a woman now,
please fuck me Mommy." Veronica was careful not to go too far with her,
after all it was her first time. After they both recovered from all the
physical activity Veronica said, "Well you've been a lovely sissy lover
for me darling so I guess it's time for you to finally received your
pleasure."

Veronica redid her lipstick and then it was her turn to drop to her knees
and suck Jessica's cute sissy cock. Unfortunately for poor Jessica it was
all over in less than 30 seconds. The makeup, clothes, sex and all the
other activities had taken their toll and poor Jessica was spurting as
quickly as possible. It was so intense she almost fainted, but when she'd
recovered she seemed disappointed that it was over so soon.

"Don't worry darling, it was your first time, next time we'll do things
to make you hold out longer."

"I presume you enjoyed yourself and you'd like there to be a next time
dear?"

"Oh Lord yes Mommy," I quickly replied. "Well then you keep all of this
to yourself, just you and me sweetheart and no one else and Mommy will
teach you everything."

"Shall we say next Saturday at the same time darling?"

The End

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I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

3 years ago
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From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved to have an ongoing affair with Her. I know that I am not near man enough for Her and I have always know that from the first time I saw Her. Eventually after being friends for many years, I...

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