Sissy Sisters Schooling
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Sissy Sisters Sleepover free porn video
SISSY SISTER SLEEPOVER by Throne
Crocket was so nervous. The only people who had seen him in his sissy
persona of Cricket were a few friends of his mother, Marion. Now she had
invited a new female friend, who was bringing someone male along with
her. Crocket was a short, college-aged boy. His mom had detected his
girly tendencies early on. He had two older brothers, now grown and
moved out. When the second of them had left, two years before, she had
called Crocket to his brother's vacated bedroom to have a talk. Marion
was very open about her assumptions and gently asked him if what she
believed was true. Sitting on the edge of the bed with her standing over
him, he hung his head and admitted that he did, indeed, long to dress and
act like a girl.
Instead of being upset, she sat down beside him and put a reassuring arm
over his narrow shoulders. All she wanted, Marion explained, was for him
to be happy. She had always wished she had a daughter and wouldn't mind
helping him assume that role. His dad had left them several years
before, so he didn't have to be considered. And the older brothers,
Marion pointed out, had figured out that Crocket wasn't going to join the
football team or get some girl pregnant. He sighed and took his mother's
hand. She gently lifted his chin so that their eyes met.
"Now listen to me, Crocket," she said kindly. "All I need for you is to
trust me and to relax. All right? I know you peek at my catalogs,
especially the ones with lingerie in them, so I've ordered you a few
things to get started with. The package should arrive tomorrow or the
next day. So just take a deep breath and don't worry about anything."
She squeezed his soft hand. "All right?"
He nodded. "Thanks, mom."
She got up and stroked his smooth cheek. "You're welcome, baby. And I
figure I shouldn't be calling you Crocket anymore. Have you thought
about a girl's name that you would like?"
He bit his lips and hesitated. Then he said uncertainly, "Well, I
thought one that might be nice is... Cricket."
She smiled and said, "That's perfect. A pretty name for someone who will
soon be a very pretty girl... Cricket."
The package was brought the next day by a good looking delivery man.
Marion gave it to her son and told him that he could open it in his room,
if he preferred. He told her that he would like them to do it together.
So they went to the small, paneled den at the back of the house and sat
on opposite ends of the couch. He carefully opened the box and removed
some tissue paper. Then came a clear plastic bag in which he saw three
pairs of cotton full-cut panties. There were three colors: peach,
strawberry, banana. He reached in again and came out with another bag,
this one containing a pair of pajamas with short sleeves and legs,
decorated all over with cute kitty cats. Almost not daring to hope for
more, Crocket put his hand in again and found a final bag, this one
holding two pale pink, A-cup bras with padding. He looked at his mother
as if expecting her to suddenly change her mind and take it all back. He
hugged the panties to his almost hairless chest and gave her a hopeful
half-smile.
Marion smiled back and assured him, "It's all for you, darling. None of
it would fit me anyway. Now why don't you take everything to your room
and get it out of those bags. And if you'd like to try anything on, that
would be fine, too."
Barely able to believe this abrupt change in his life, he thanked her in
an emotion-choked whisper, scooped it all up, and walked away. In his
own bedroom he fought to hold back tears of happiness. For years he had
longed to own such items, to put them on and feel them against his skin.
With care he opened each bag and laid everything out, as if they were
precious treasures. In a sense, they were. Crocket ran his fingertips
lightly over the panties and gingerly picked up the peach ones. They
weighed so little that it was almost like they weren't there. He looked
down at the denim jeans he was wearing. They were designed for a guy and
felt wrong to him. He took them off, along with his plaid sports shirt.
Looking down at his body he was reminded of how small his penis was. Its
size had never bothered him as it might a regular young man. He enjoyed
a private smile at seeing how he had trimmed back his pubic hair. Not
that there was much of it to begin with. But he preferred it this way.
He felt pulled in two directions. The panties were so appealing but also
carried the stigma of being forbidden. He waited another half minute,
took a deep breath, and put one foot through them and then the other. As
he drew them up his slender legs it was as if his world were changing.
They neatly contained his small genitals but he still couldn't resist
tucking everything down and back, for an even less masculine appearance.
Crocket took a few steps and thrilled to how the material caressed him.
Did he dare to don the bra as well? With the encouragement his mother
had given him, he was able to summon the courage. His fingers quivered a
bit as he opened it and slipped his arms into the straps. When he
reached around he discovered that, because this was his first time, he
didn't quite know how to fasten it. After a few tries, however, he got
the job done.
Crocket went to his closet. On the inside of the door was mounted a full
length mirror. His mom had gotten one of his brothers to hang it there a
few years ago, perhaps in anticipation of his occasion. Should he use it
to see his reflection? Would he like what was there? Or would he just
be a guy in girl's underthings? Biting his lips, he turned the knob and
slowly swung open the door. Facing him was a rather sweet looking
figure, still obviously male but with plenty of potential to take this
transformation further. He held his arms out slightly and let his wrists
go limp, cocked his head to one side, and gave his hips a wiggle. A
current of excitement ran down his spine and triggered even stronger
sensations in his penis. He gasped and put his hands over the cups of
the bra, noticing as he did it how very feminine the gesture was.
Next he scampered over to his dresser, opened the drawer, and found the
tube of lip gloss he had recently purchased. It was supposed to be used
to keep your lips from getting too dry, but he had been pretending it was
lipstick. Now he applied it more generously than ever before. He picked
up his hairbrush and ran it through his collar-length locks, trying to
give them a bit of style. If only he had some product to use. When he
returned to the mirror his lips didn't look any different and his hair
was almost the same as it had been, but just the fact that he was now
able to try to make himself appear more girly was deeply liberating. He
fanned the air in front of his face with one hand while putting the other
on his hip.
Should he show his mother? Did she want to see? Would she be
disappointed?
He decided to be brave and go show her. But he was still a bit of a
coward about it, so he put on his robe. It was heavy and dark had narrow
lapels. Not at all what he would have picked in his current mood, yet he
didn't want to turn into a fussbudget, not when he was being treated with
so much love and concern. He tied the robe and padded out of the room,
his thoughts divided between confronting his mom and wishing he had some
appropriate footwear. Crocket found her still in the den, waiting
patiently. She wore a welcoming expression as he came into the room.
He stood across from where she sat and slowly untied his robe. She
nodded approvingly, so he opened it all the way and, feeling his cheeks
burning, showed her his new look. Marion clapped her hands in delight.
"Oh, sweetie," she said happily. "That's just how I pictured you
looking. I'm so pleased. Why don't you get all the way out of that
bulky old robe and move around some to give me a better look?"
Crocket slid the robe off and set it on a chair. He moved around the
room, using the hip-rolling walk he had practiced in his mind so often.
His mother let him do that for a while and he even struck a few modest
poses, ones that might have been used by a model for young girls'
clothing. Marion rose and came toward him with her arms opened to give
him a warm embrace. He knew that everything was going to be so much
better for him from then on. And it had been, with his mom taking him
shopping and discretely buying more goodies for him to wear at home,
gradually building a wardrobe of pretty dresses, knee socks, frivolous
plastic jewelry and other things that would look good on a girl in her
early teens. He appreciated that look and honestly didn't want anything
flashier. He had been happy with their conspiratorial efforts to make
him the sweet sissy he had long wanted to be. Soon there were razors and
depilatories so he could eliminate his unwanted body hair, scant though
it was, and even some gel so he could style his hair on the weekends.
When she invited one of her lady friends to the house to see him as
Cricket, he was scared. But Marion assured him that this was someone who
would understand and could be trusted. It turned out that Beryl was all
that and more. She suggested that Cricket was ready to be introduced to
cosmetics, though she advised that they be applied lightly. Marion
thought that would be fine and on their next shopping trip all three of
them picked out some starter supplies. Crocket learned how to use eye
shadow and lipstick and even blush. He was euphoric when he saw how much
nicer he now looked as Cricket. Soon there were girls' shoes, though no
high heels. He was happy with flats, seeing himself more as a young miss
and not at all as a grown-up woman. Together with his mom and Beryl, and
soon two more of Marion's close friends, he redecorated his bedroom,
turning it into a pink and white dream.
All of that took a year and he was content the entire time. One of the
women owned a fabric shop and gave him a part-time job there. He had to
dress in boy clothes for work but always had panties and a bra on
underneath. But when his mom announced that she had a new friend who was
coming to visit on Friday evening, Crocket was upset, especially because
the newcomer was bringing someone male. Crocket had been noticing guys
more and more, singling out the cute ones for the majority of his secret
glances, but he didn't feel prepared to actually meet whoever this woman
was bringing.
But when Crocket got home from work Friday afternoon, Marion's plans
hadn't changed. She put her arms around him and asked if he trusted her.
He told her he did but mentioned that maybe it was too soon to bring
someone else into their circle. She squeezed his shoulders and told him
everything would be okay. Then she had him finish preparing the dinner
she was cooking. That always soothed him. He enjoyed cleaning, folding
the laundry, making the beds, and so on. She hired someone to mow the
lawn, a guy several years older than Crocket who was very fit and showed
off his well developed arms. After they had eaten and Crocket loaded the
dishes into the washer, his mom told him that she had laid out what he
was going to wear in the spare bedroom, and that he could change into it
after he had a bubble bath to help him unwind.
He lounged in the tub, telling himself that he needed to trust his mom
completely and that she had never let him down since all this had
started. After he showered off and applied some perfumed powder, he went
to the spare bedroom, where he got a surprise. He had been wondering if
he would find a party dress or maybe a pant suit. Instead, there was a
pair of cotton, baby doll pajamas with a floral print. They had lace
trim on their shoulder straps and a narrow ruffled hem, which was
duplicated around the leg holes of the bloomer-style bottoms. On the
floor were a pair of fluffy slippers. He got out of his robe, a
hyacinth-colored one with wide lapels and tassels on the ends of its tie,
that had replaced his boring old one. Crocket put on the pajamas and
inspected himself in the mirror. His mom certainly knew his taste.
From there he went to his room to give his hair some body and curl its
ends under on the sides. Then he lightly used an eyebrow pencil plus eye
shadow, and applied a touch of subtle red lipstick, all of which
conformed to his unwritten dress code. He checked himself one last time
in the mirror, liked what he saw, and draped his robe over his arm,
because Marion might want him to put it back on for when her guests
arrived. He found his mom watching TV, a shopping show that was
featuring clothes that would suit her but not him. He was interested in
all aspects of female fashions, however, so he sat and quietly viewed it
with her. When a commercial came on she used the remote to mute the
sound and turned to him.
"Well, Cricket, what do you think of what I selected for you?"
"It's... nice. But, well, I wasn't sure if it was right for when company
comes."
She gave him a sympathetic look. "It will be. You'll see."
The two of them went to the kitchen to finish preparing snacks. After
that, Marion went to her room to get dressed. She selected a pants suit
and tried a new shade of lipstick, something close to what Crocket was
wearing. They joked about their similar tastes and she gave him an air
kiss. Then they watched some more TV for about a half hour before the
doorbell rang. Crocket questioned his mother with his eyes. She told
him that he didn't have to answer the door, and went to do it herself.
When she returned she was accompanied by a woman about her age, neatly
dressed but not overdressed. Following her, looking as uneasy as Crocket
felt, was a young man in a long overcoat. He took it off and underneath
he wore -- oh my! -- pajamas like Crocket's but with a different floral
print. He stepped out of his slip-on loafers and the woman took a pair
of slippers with bows on them from her copious shoulder bag. He got into
those and could have passed for Crocket's... sister. Sissy sister.
He had on a hint of eye shadow and his eyebrows had been thinned and
shaped slightly. The woman took a tube of lip gloss from her bag and
applied it to his mouth.
She said, "Marion, I'd like you to meet my former son Joseph, now my
precious daughter Josie."
Crocket's mother greeted him and said, "Edna, this is my used-to-be son
Crocket, now my darling daughter Cricket."
The two sissies were sent to the kitchen to get the snacks. They kept
peeping at each other, not sure what to do next. After they returned and
their mothers had eaten a few tidbits, Marion went to get drinks. She
brought back two glasses of ginger ale, and two bottles of cherry cola
with straws in them. The moms got the glasses and the guys were given
the bottles. The latter pair stood there shifting their slipper-shod
feet. Marion invited them to sit on the couch together. They put
themselves as far from each other as the piece of furniture allowed.
Their parents looked at each other knowingly.
After the women had chatted briefly, they turned their attention back to
their offspring. Marion said, "The reason Josie is here, and the you're
both in those scrumptious pajamas, is that we decided you two should have
a sleepover. You may take your beverages and go to Cricket's room, if
you promise not to spill. I've picked a movie for you to watch. You'll
be allowed to stay up until eleven and then it's lights out, young
ladies. Understood?"
The two of them nodded. Edna added, "We expect you both to be on your
best behavior. If we hear any loud talking or other noise, we'll be
right in to see what's going on. Right?"
More nods. The two boys in girls' pajamas and slippers got up. Crocket
led Joseph toward his room. When they got there, Joseph look around
wide-eyed.
He broke the silence by saying, in a wispy voice, "This is beautiful."
Then he put his hand delicately over his mouth, shy about having spoken.
"My mom picked most of what's here," Crocket explained. "But she let me
help."
There were another few moments of uneasy silence and then Joseph asked
about the lamp on the dresser, the base of which was a Cupid figure.
That started a conversation and it was as if a dam had broken and
released a flood of words. Neither of them had had anyone like
themselves to talk with and this was a great relief for both of them.
They gabbed about clothes and make-up and -- blushingly -- managing their
pubic hair. Crocket had removed all of his but Joseph still retained a
'landing strip'. Soon they were sitting on the bed, giggling and
touching each other on the shoulders and upper arms to emphasize what
they were saying. Noticing the time on his fairy princess clock, Crocket
decided they should put the movie in.
"We can always talk more after it's over," he pointed out. "Would that
be okay, Josie?"
"That would be super, Cricket. What did you mom choose for us to see?"
"Ooh," Crocket said, his mouth forming an 'O'. "It's one of those about
a bunch of kids in a creepy old house."
"Those things scare me," Joseph admitted.
"Me too, so I can't protect you," Crocket told him.
"I guess we'll have to protect each other."
That started them laughing. In the den the mothers heard the sound and
agreed they were glad they had come up with the sleepover idea. It would
be good for both their 'daughters'.
Back in the frilly bedroom, the movie was starting. The boys sat against
the scrollwork headboard, leaning back on fat pillows with pretty
pillowcases. They watched as the film progressed predictably. Crocket
said that he thought one of the guys was dreamy but Joseph liked the
other one. That provoked snickers and Crocket paused the video so they
could talk some more. The two of them compared secret boy crushes they
had had on guys they'd seen locally and in movies, as well as members of
boy bands. They finished their sodas and Crocket placed the empties
neatly on the end of his dresser, not wanting to do anything to earn his
mother's disapproval and possibly spoil their chances of future get-
togethers.
The two of them watched the movie and yelped every time there was another
staged scary surprise. During a chase thorough the old house they clung
to each other but, when it was over, moved apart bashfully. At last the
movie ended and it was getting close to their curfew. They took the
bottles to the recycle bin and then went to check in with their moms.
Edna had her son's toothbrush. Each of the guys gave his mother a
goodnight kiss on the cheek and then they went to rinse their faces and
brush their teeth. They slipped into bed and pulled the covers up under
their smooth chins. For a few minutes they talked about the ending of
the movie, then got back to those handsome male stars. That led to
another discussion of clothes and cosmetics, which started to run down as
both of them got overly sleepy.
Crocket asked, "May I give you a goodnight hug, Josie?"
"I'd like that, Cricket." He tittered nervously. "And I'll hug you
back."
They clung together and drifted off to sleep in each other's arms,
pleased to have each found someone special in who they could confide.
And they still had Saturday morning to share and -- they both eagerly
hoped -- many more sleepovers to come.
*********
(What would YOUR ideal sleepover be like? Details, please.)
Rowan
- 29.06.2021
- 29
- 0
