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The Reawakening Of Sissy Jackson free porn video
The Reawakening of Sissy Jackson
By Cassandra Morgan
The memories came at night, when his consciousness was not on guard to
stop them.
A little boy, rushing across the playground to his mother. She laughs and
picked him up, kisses him on his lips. He is a small boy, frail, too weak
to play ball sports with the other kids. He plays on the swings...but not
too high. He plays hopscotch. He plays jump rope.
The mommy does not care. She likes having her little boy close to him,
and if he went to play with the other boys, he would be on a distant
field. She strokes his hair, which she really should get cut put it is
just so pretty. She traces his lips with her finger. He buries his face
in her neck and giggles. She lifts him to the sky.
Let the other parents make fun, she was thinking. Like the song said,
it's he and me against the world. He was her Sissy-boy.
* * *
Theo Jackson wakes, and he slides out of bed. He is hard again. The damn
dreams always make him hard.
He pads across the bedroom and enters. He pees. He takes a bit of toilet
paper and wipes the seat, just in case he sprayed. He retreats to bed,
where Heather is sleeping. He eases in beside of her. She reached out and
clenches his hand. He squeezes back.
Again, he closes his eyes and allows the memories to invade his thoughts.
He misses his mother, who lives in Indianapolis. There was something warm
about her home. Something comforting.
He purposefully thinks of his wife naked. If he is going to be erect,
there should be a present-day reason for it. Not these old memories he
thought he had forgotten.
He is Theo Jackson, an English teacher from Cincinnati. He would be 29 on
his next birthday, He and Heather were coming up on their fourth
anniversary. Life was pretty good.
But there were these dreams. That kept coming back to him.
* * *
He was three, maybe four. His mom was playing with him on the floor of
his room.
She took his G.I. Joe, and she put a Barbie dress on him. He laughed, and
he laughed. She hugged him again. Let others say they were too close. How
the hell could you be too close with your own kid? He had taken a
Popsicle and frozen his lips until they were cherry-colored. He cackled.
She wiped his mouth. Then she took a tube of her lipstick and had him sit
still. She ran it over his lips until they glistened. "So pretty, Theo,"
she said. "So pretty. Here. Let me put your hair in pigtails.
"Now, who's my sissy boy?"
* * *
He wasn't the most macho guy. He didn't work on cars or fix broken
electronics. He baked. He sewed.
These were the gifts he had brought from his upbringing. His mom always
insisted that he be able to maintain his own possessions, so she had
taught him how to use a needle and thread, an iron and an oven.
Heather didn't seem to mind. She was a grownup, and she knew that muscle
cars and weekend football games didn't measure a man. But she liked that
he was smart, that he could discuss Hemingway and Harper Lee. Oh, the
kids at school made gay jokes about him all the time, but they were just
joking. He was a good teacher. He was liked.
She knew he was not sleeping well. His stomach, maybe? He was kind of
frail, a little sickly. Some men just fight off sickness. Not Theo. He
would bundle up with tissues all day. But he used to sleep the sleep of
the innocent. These days, he was fitful. She wished she knew what was
bothering him.
It was nothing, Theo would tell her. Then he would drift asleep again,
and the dreams would return, and he would toss once again. And Heather
would worry.
* * *
He was 13, and he was helping his mother clean their apartment. There was
only the two of them - his father had left his mother when he was an
infant - so the work went quickly. They did the dishes after every meal,
and the vacuuming went pretty fast. It was the laundry that took the most
time.
On this day, he remembered in his dream, his mother stood in front of the
laundry basket and pulled out a blue shift. She held it up. "Is this
yours, Theo?" she asked. "I don't remember wearing this."
He looked at her, frozen in mid-motion. "Um, no, Mom. It isn't mine.
That's a dress."
She smiled at him. "Sweetheart, I know. I know you put on my stuff when
I'm not here. It's okay, sissy-boy. A lot of boys like to put on girls'
clothes. It doesn't make you bad."
"I'm sorry, mom," he said, hanging his head. "I was just playing."
"Sweetie. I tell you what. Why don't you get dressed up for dinner? As a
girl, I mean. It'll be all right. No one has to know but you and me."
"It's ok?"
She smiled. "Who's my Sissy boy?" she said.
* * *
The memories were so vivid, so fresh. He wondered what had caused them to
resurface in his dreams. Was it life with all the news of gay and
transgender individuals? Was it work with its stress? Was it seeing the
pretty dresses of the girls in his class?
He had not dressed since high school. He gave up all of it when he went
to college rather than be made fun of. He met Heather in Spanish class.
She was far too pretty for him, but one day, she asked for some help with
her homework. They became friends.
One night, she had looked at him and asked, "Theo... why don't you ever
make a pass at me. Are you gay?"
"No," he had stammered. "I just thought you were out of my league."
"That's sweet. But you're sure you're straight? Because I think you're
kind of cute."
He had kissed her then, awkward in his youth and lack of experience, but
enthusiastic over her beauty and his desire.
There were some people who raised their eyebrows when they started
dating, but they became close. Who knows what makes people feel attracted
to each other? The late Marilyn Monroe used to marry homely men all the
time. John and Paul of the Beatles fell in love with women who weren't
classically beautiful. And that was great. It spoke to a person's
capacity for love.
And so when Theo and Heather got married, everyone was happy for them.
Oh, Darla - his mother - seemed cool that another woman was stealing her
baby. But a boy has to leave the nest sometime. Darla kept looking at
Heather as if she couldn't quite figure out her son's infatuation with
her. But she was gracious. She said the right things.
After all, she loved her baby.
* * *
He was 16, and he sat quietly at the table. She had taken out red
fingernail polish, and she was putting it on his fingernails.
He sat in front of her in a white dress His long curls hung down by his
sides. He was wearing a red bow.
"Mom, I'm growing up. I think I should stop dressing like a girl."
"Why would you stop, Sissy?" she said. "This is our quiet time together.
The time you get to be Sissy."
"But the other boys don't dress up," he whimpered.
"The other boys are neanderthals," she said. "You're my pretty boy. So,
did you see that Mike Jernigan won the Fulbright Scholarship? He's a
cutie."
"I guess."
"Oh, Sissy. You don't think so? I think he's handsome. Do you still have
a crush on him?"
"Mom! I never had a crush on him."
She smiled. "Of course not, dear. I must have imagined you looking at him
at the theatre the other night. Of course, you were dressed as a boy, but
I bet if he saw you in this dress, he'd be pretty interested. There
aren't any girls at Kennedy High any prettier than you."
"That's my point, Mom. I'm not a girl."
"Who said you were a girl? You're my Sissy boy."
He didn't say anything.
She smiled. "When you were a baby, you couldn't get enough of your mommy.
Oh, there were others who said I was smothering you. But you liked
spending time with Mommy. You liked cooking. You liked dance class and
glee club and poetry reading."
"Yes ma'am," I said."But boys can do that without dressing like a girl."
"Are you saying I shouldn't have bought you your new dress? Or your new
earrings?"
"No ma'am," I said. "I appreciate those things."
"Theo, there are degrees of boys. You all have different amounts of
testosterone. Randy Lambaugh? He's got high test. It's why he's so rough-
and-tumble. But you? You barely have any. I half expected your breasts to
grow when you were a younger girl. I mean, a younger sissy. It's like
cars. There are muscle cars and sports cars and SUVs. And then there are
little girlie cars. That's you. You're a girlie car."
"Now, let's do something with your hair. You need to be pretty, Sissy
Boy."
* * *
Theo woke up in the middle of the night, again. He slid out of the
covers. He stole into the office.
He fired up the computer.
There, he found it. A sissy site. There were men in sissy dresses, men
cleaning, men posing in maid's dresses. He became erect almost
immediately.
He turned to the stories. This guy whose wife pushed him to being a
sissy. That guy who who stepped into a machine and got breasts. That guy
whose wife forced him to perform sex on other men. That guy whose wife
screwed another man in front of him.
Was this him? He had been Sissy Boy growing up, but that was before
sissidom had taken on the spectre of sex. No one was dressing him now.
Why did he miss it so much? Why could he close his eyes and feel the
panties slide up his legs, or the bra go around his chest? Why could he
feel lipstick on his lips?
God, it was still there, wasn't it? After all of these years, it was
still inside him.
He shut the computer down. He padded back to bed. Heather had not moved.
He slid into the bed. He bit his lip.
What was he going to do?
* * *
He read more and more. Maid stories. Mistress stories. Transvestite
stories. He read everything he could find about Caitlyn Jenner, about
Laverne Cox, about Christine Jorgenson. He watched You-Tube videos about
sissies. And his desires grew. This was no longer something from his
distant pass. His desires were present-tense. As real and as relentless
as ever.
He imagined himself in a pink princess dress. Or a blue bridesmaids
dress. Or a black maid's dress. God, he hated this part of himself. He
was a sissy in denial. What was to become of him?
He read more. Did he want to suck a cock, like a lot of sissies? Did he
want to wear a diaper? Did he want to be soaked by a golden shower?
He didn't know. He was just a sissy.
* * *
He was 17, a high school senior. His mother had bought him a yellow prom
dress.
This was nuts. He wasn't going to wear it. Hell, he wasn't going to the
Prom. No date. He wasn't going to be one of those geeks who hung out with
the other geeks so they can act cool.
He felt the material. Taffeta. There was a sheer shell covering it that
gave it a hint of heaven. It was beautiful.
"Put it on, Sissy," his mother implored. "It's okay."
He looked with doubt in his eyes. He was NOT going to the prom. He'd get
beaten bloody.
"You don't have to go," his mom whispered, as if she could read his mind.
"Just put it on and wear it around the house. We'll watch a movie. Just
you and I, Sissy-Boy. We'll watch musicals like the old days. Or fairy
princess cartoons,"
And so he did. He wore his breast inserts, and his mother set his hair
and sprayed it to death. She did his makeup. He was gorgeous. He was
perfect.
They sat on the couch and, instead of musicals, they watched Twilight. He
didn't like vampires, but he loved romance, and this was full of it. What
if a vampire wanted him? What if it was a guy vampire who wanted to bite
his neck. He smiled inside. What could he bite in return?
"I should have invited Mike over. Every girl should get kissed on her
prom."
"Mom." I said.
"Be careful of his thingie," Mom said.
"Mom!"
His mother laughed. She held his hand and smiled at him. "You are so
pretty, Sissy-Boy. Don't you ever leave me."
* * *
Heather was reading a magazine when Theo came in. He sat down and looked
at her.
"What?" she said.
"We need to talk," he said, swallowing hard.
"What's up, Theo? What's on your mind?"
"We need to talk ... about me."
"About you?" Heather put down her magazine to pay closer attention.
"Yeah," he said. "You know I've had trouble sleeping?"
"I know."
"I've...I've been thinking about growing up lately."
"What about it?" she said. "You grew up to be a fine man."
He smiled remorsefully. "I grew up...girly," he said. "I know that. My
mom raised me ... unconventionally."
"I don't know what you mean."
"Hell, Heather. I was raised as a sissy. My mom smothered me when I was
an infant. She bought me dolls and toy ovens and jewelry-making kits. She
bought me dresses. I wore them. It's a wonder I didn't marry your
brother."
"A sissy? Oh, I guess that makes sense."
"It ... makes sense?"
"Sure it does, Theo. Hell, I knew you weren't the most muscled guy in the
world. I fell in love with your mind, with your soul. Remember, I thought
you were gay when we first started hanging out. So, did you look pretty?
Did you like dresses?"
?I don't know," I said. ?It was... all-encompassing. It was the basis of
our closeness. The more girlish she kept me, the closer I felt to her.
Because I had no other friends."
?I see. Were you gay? Is there something I need to know?"
?No!" Theo said. ?I mean, no. I was never with a guy. But mom would talk
about guys she thought I would be interested in."
?So why is this coming up now, Theo? We've been together for so long."
?I'm ? having dreams," he said. ?Different moments are coming back to me.
Sissy moments."
She nodded.
?So what does this mean to us now."
?Heather," he said quietly. ?I want to be Sissy Boy again."
* * *
Heather had no idea what to do. She loved her husband, but she didn't
know anything about this life style. What was a mistress? What was
serving? She glanced at the story on her computer screen. They sure used
the word ?simpering" a lot.
Was she supposed to be in control? Was she supposed to spank him? To put
him in a cock cage and force him to have sex with guys? She didn't want
her husband having sex with anyone else, let alone guys.
Was he going to wear dresses now? Makeup? Women's jewelry? God, there was
so much to learn.
She never thought of leaving him. This was just an affectation. Like
walking with a cane. She could learn to live with it, she thought.
So he cooked and cleaned? That was good for her, right? If you thought of
this as just a mind on sidetrack, then it wasn't so bad. Who was he
hurting? So he wanted to wear fake tits. Wait. Did he want real tits? Did
he want a vagina? Did he want a sailor?
She kept reading. Most sissies are straight, she read. A lot of them were
crossdressers. Technically, I guess you can call Theo a crossdresser. He
seemed to want to be, anyway. Some of them are cuckolds. She didn't want
to have sex with anyone else either. At least not now.
Should she ask if he wanted to wear a cock cage? It seemed harsh to her,
but a lot of sissies seemed to like them. How about his hair? Should he
wear a wig? Or was there enough there to style? How about lipstick? How
about high heels? God, she could imagine him trying to walk in heels.
Would he be pretty? She wondered. Would he be effeminate? Probably. Would
he want to wear a maid's dress most days? Maybe. Would people think she
was a lesbian?
Her husband. A sissy. She giggled. It was surprising how it wasn't that
surprising. I mean, Theo was on the verge of a major transition, but
she'd known he was kind of girly all along. She didn't know the term for
it, but she knew he was kind of a sissy.
So what did that make her? Had she somehow known when they started
dating? Was she, by process of elimination, a Mistress? And if so, would
his nature bring that out of her?
Mistress Heather, she thought, putting her hands on her hips.
Grrr.
* * *
That night, Theo took her into the bathroom. He had creams and lotions
under his arm.
Hair-removal. Body lotion. Bath oils.
He looked at her. ?Are we really going to do this?"
She nodded. ?We are if you ever want to sleep again," she said.
First, Theo bathed. Then she rubbed the hair-removal on him. Then the
body lotions. He was smooth and smelled nice. Not manly, but nice.
Heather ran her hands over his chest. Smooth. Sweet.
?Would you like go wear one of my bras?" she said hesitantly.
?I ? I bought some today on the trip home from work."
So he put on the bra like an old pro, fastening it and spinning a beige
one. He slid the panties up. He had done it enough times as a teenager.
He bit his lip. Then he pulled a pink maid's dress it of the closet and
stepped into it. He pulled it up. Heather zipped it up.
He had to put on hose, and he had to put on lipstick. But there he was,
the outline of a sissy. She smiled. ?You're lovely," she said. ?What do I
call you."
?My mother just called me Sissy. Or Sissy Boy."
?Hello, Sissy Boy. Nice to meet you."
Sissy curtsied. Then grinned.
?Are we...okay?"
?I hope so," Heather said. ?I love you. And this is just...accessories.
But I'll be honest. I don't know how to be a Mistress. You'll have to
bear with me if you want me to be one. It's going to take communication
and compromise, Sissy. There is so much I don't know."
?I don't know, either. I was a girl... I mean boy when I played at being
a sissy before."
?I know," Heather said. ?Why don't we call your mother? She knows Sissy.
She can help."
Sissy nodded. ?That's a good idea. I'll bet she'll be surprised that
Sissy is back."
Heather grinned. ?I bet she won't be."
* * *
Darla Jackson beamed the first time she saw her sissy as an adult. She'd
thought he was gone forever, swallowed up by the straight life. But there
she was, in a soft blue dress, her hair curled, her lips red. Sissy boy.
She was making dinner, allowing the women to talk.
For Darla, it felt as if she had her daughter back. Oh, she had always
taken care to call him a boy, or a sissy. But inside, she had always
thought of him as a girl. As her baby. She wanted him to be happy.
?Heather," she said. ?It's so nice to see you again. I think it's
marvelous that you have accepted this side of my son. I was afraid you
would want him to be ? a man."
Heather smiled. ?I love her," she said. ?That's all that matters.
Everything else is ? adjustments."
?Are you prepared to be her Mistress? It isn't easy."
?That's kind of what we asked you here for, Mrs Jackson..."
?Darla."
Heather nodded. ?I'm kind of a rube about being a Mistress. I only know
what I read, and the role of Mistress takes on many forms in fiction. The
dominatrix, the bitch, the cheat, the bully."
Darla nodded. ?Sometimes, it depends on your sissy," she said. ?Never
forget. It's about her needs. I'm not just saying that because she's
mine. But if she needs control, you have to provide it. If she needs
discipline, you have to provide it."
?I see."
?I'm not sure you do. Let's talk about guys, okay? If she needs
submission, and you decide she needs a cock, then you have to be strong
enough to put her needs over yours. Can you do that? If she needs a
spanking, well, spare the rod and spoil the sissy."
?Like the dresses?"
?Well, Sissy connects this lifestyle with crossdressing. My fault, I'm
afraid. I encouraged it. But even as a kid, she was hanging around with
girls, playing tag, playing with dolls. Maybe it was inevitable."
?It doesn't matter, Darla. If Sissy wants dresses, we'll keep her in
dresses."
?You know she likes that maid stuff."
?I know."
?It's a sweet deal for you. Your place will always be clean, and your
clothes will always be ironed. She's loyal. She's loving."
?Here's a personal question. What about sex?"
Mother shrugged. ?That's between you two. I know I teased her about a boy
in high school, and she wasn't that interested. So I think she's fine for
sex. I do think you need to make her satisfy you...orally. You may need
to penetrate her. Make her suck your dildo."
?Oh, God. I'm talking about sex with my mother-in-law."
Darla smiled. ?Honey, it's just sex. We all have tabs and we all have
slots. Just keep each other happy, and you'll do fine. My daughter-in-law
is a Mistress! Isn't that great?"
Heather looked toward the kitchen. Sissy was moving around the kitchen
like a stereotype, his wrists flopping, his hips swaying. His makeup was
flawless. He was humming.
God, what a sissy, she thought.
Her sissy.
* * *
Sissy lay in bed, her hair curled, her lipstick fresh. She was wearing an
off-white nightgown. She had been fluffing her breasts, as if to make
them grow. She was taking pills, but they were so slow.
Then Heather walked out of the bathroom.
And Sissy's eyes bulged.
It wasn't that Heather was beautiful, although she was. It wasn't that
she was almost naked, which she was. It was that, sticking out of her
panties, was a large, thick penis.
It was a dildo, of course, jutting out of her crotch like she was a porn
star. It was flesh-colored, with testicles attached. It even had veins
popping out of it. If not for Heather's ample breasts, Sissy would have
sworn it was real.
Heather walked up to her side of the bed. ?You like?" she purred.
Sissy nodded and reached out and touched it.
?You can kiss it," she said.
Sissy leaned forward. She licked it. She parted her lips, and it slid
inside of her skull. Her eyes never left Heather's.
Then Heather was grinding her, screwing her mouth, taking her for hers.
Heather humped for a while, then got tired and pulled out. She touched
his shoulder, indicating that he should turn over. Sissy did. Heather
applied lube, then prodded Sissy's anus with the tip. She guided it in
with her hand, then inched it forward, slowly, determined.
This had been for Sissy, but the truth was, Heather liked it. She loved
the look on Sissy's face, the way her body reacted. She reached out, and
Sissy's small penis was straining for release.She rubbed it, stroked it.
It was different sex, but it was good sex.
Just for fun, Heather reached back and slapped Sissy's ass.
Sissy grinned. ?I'll give you an hour and a half to stop that," she said.
Heather slapped it again. She pulled Heather's face to hers and kissed
her. She cuddled against her. They were lesbians. They were Mistress and
sissy. They were husband and wife. They were domme and sub. They were all
things to each other, and it was perfect.
The certainty, Heather said, was Sissy. She was, indeed, a sissy. But the
uncertainty was Heather, who was learning as she went.
Tomorrow is behind a veil. Heather didn't know what would happen. Would
Sissy crave a man? Would Heather need a partner who was not a sissy?
Would Sissy find other sissies to play with? Would they work out?
For now, Heather had love. That felt like enough.
Enough for her and her Sissy Boy.
(c) 2015 by Cassandra Morgan
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