Claire Kent Alias Super Sister The Return of Superboy
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Lady Boy Parts I-IV free porn video
Lady Boy
Part I
Fantasy can become reality and sometimes not for the better!
Since the age of 12 Chris had been experimenting with cross dressing. It
was a very innocent obsession that had begun around puberty. He found
himself looking into his sister's drawers when she was gone, and trying
on various items of her lingerie. He was a small boy and was able to fit
into most of her clothes.
He lived for the weekends when his mother and sister went away, leaving
him to totally become the female version of himself. He never dared to
go outside the house. In fact he was terrified of anyone seeing him and
exposing his fetish.
Chris was very careful to put everything back the way it was and it was
because of this that he was able to avoid detection from his sister. His
sister was almost 16 and was really into the Brittany Spears trend, and
loved to imitate her whorish ways. Chris of course delighted in this
fact as he would get full advantage of the new clothes she was constantly
buying.
At the age of 13, Chris became increasingly more interested in scanning
she male sites on the internet and would masturbate at the pictures of
the men dressed as women. This was his fantasy of course, but he knew he
could never really do it in public. He would keep this, his secret for
life, or so he thought at the time. Chris began experimenting with
makeup now and was getting quite proficient with it. His hair was now
shoulder length, which really ticked his mother off, but he loved to tie
it back in a pony tail during his own private sessions with himself,
turning himself into his own fantasy.
By 14, Chris had progressed onto the transgender chat sites and was
having daily conversations with other people sharing the same fantasies.
He would always jerk off while in front of the monitor, and would see
others on the web cams. He too was now participating on the web cam,
unafraid of what anyone might see or discover, completely secure that his
identity would remain anonymous. In fact while he was made up and
dressed up he truly didn't recognize himself anyway and was confident his
secret would remain forever.
Going through school, Chris found he had fewer and fewer male friends.
His hair was now actually quite long, at least for a boy. He was
starting to get teased by both boys and girls and at home he endured
constant tormenting from his sister. Chris was very slight in build and
not very tall either, and in fact had a body resembling a young woman in
some aspects at least. He found himself being outcast by classmates both
male and female. He was lonely during the day, but he knew when he got
home, his true friends, those on the internet would speak with him.
Part II (First Meeting)
Before Chris reached the age of 15, he was on the internet for hours a
day, researching several transgender sites and had made new friends on
different related chat forums. One person who identified themselves as
Cameron was a constant chat partner with Chris. They would see each
other on the web cams and would occasionally even talk on the telephone.
Cameron was a beautiful young woman, who looked to be about 25 and was
very statuesque in her build. Chris found that Cameron always dominated
their conversations, and something about that intrigued him. He found
himself doing things for her on the web cam that he thought he would
never do. He had never exposed himself to what was still really a
stranger to this extent.
Chris began talking with Cameron on a daily basis. What he liked about
her was her acceptance of his cross dressing fetish and she seemed to
often encourage him to do more of it. She would suggest to Chris what to
wear and how to buy things on line. She was a great help in furthering
Chris's fantasy of being a woman.
Cameron made Chris that he would meet her on his sixteenth birthday. She
lived in the same city, so it wouldn't be hard to arrange. Chris didn't
think he would ever have the nerve. Slowly, Chris became more and more
at ease when speaking with Cameron. She was gaining his trust rapidly as
his birthday approached.
Cameron suggested a simple meeting at a coffee shop for the two of them
to get acquainted. She asked Chris not to get dressed up, at least not
on the outside, but suggested to him that he wear panties and perhaps
nylons with garters under his jeans. When the suggestion was made over
the phone, Chris became very excited and actually had to masturbate right
afterwards. He wasn't sure why, but Cameron was certainly a lady he
wanted to meet. He decided then and there that he would meet her and
finally take a chance.
It was a Saturday night when they met. 8.00 Sharp she told him and he
was on time sitting there waiting for her, thinking about the lingerie
under his jeans. He took a small chance and didn't wear socks over the
nylons, so when he sat, one could see the nylons over his exposed ankles
if they were really looking. In his mind of course, everyone was looking
at his ankles. He imagined that everyone knew what he was wearing. He
was sweating.
At 8.15 Cameron was still not there and Chris really began to worry that
she wasn't coming, then an SUV pulled up, it was a Mercedes and looked
brand new. Chris didn't know she had money, they had never spoken of
stuff like that. After all she was almost 10 years his senior. He
watched as Cameron looked into her rear view mirror and touched up her
hair and makeup. Then she got out of the car. The first thing he saw
was her long legs accented by black nylons and very high heels. She had
a mid length coat on so when she stood it fell below her waist, partially
covering her mini skirt and upper thigh. Still he had seen what he
wanted before she stood. His mouth went dry.
It was very obvious she was a confident woman. You could tell the way
she strutted into the store, oblivious to the stares of some of the
customers. She knew who Chris was, they had seen each other many times
on the web cam. She smiled at him and approached. He stood up and
introduced himself, offering his hand. Instead she offered him her
cheek, which he kissed very lightly. She was much taller than him, but
those heels had to be 5 inches anyway and she was able to dwarf him in
her stature.
She sat. They both just stared at each other for a moment. Her makeup
was impeccable, her hair exquisite. You could tell she was a
perfectionist, everything he dreamed of being. Then she spoke saying
only 'hello' and then he felt her hand under the table rub up his thigh
until encountering the small 'bumps' created by the garter he wore. She
smiled and seemed pleased. His face went red, He was very embarrassed at
her discovery but didn't know why he would be when he knew that she knew
all along.
She asked him to stand up and turn around for her. He did so without
objection, and she seemed to be surveying him in a strange and wonderful
way. She smiled as she did this. She commented on his hair, how long it
was and how so many things could be done with it if he let her help him
with it. He didn't know what to respond, just sat silent as she spoke.
She reached over with her hand and drew one of her long finger nails
across his eyebrow, commenting how bushy they were and how easy it would
be for her to fix them for him. She suggested that he let her pluck them
and shaped them in a more feminine style and explained that nobody would
notice anyway. He wasn't sure about that but was still interested. She
seemed to captivate him, his imagination was going wild looking at her.
Imagining himself looking like her, a beautiful woman.
Cameron then reached over and held his hand. "Would you like to get to
know me a little better?" she almost whispered to him. He nodded without
hesitation. He couldn't believe this beautiful woman was even interested
in him, especially knowing his hidden fetish.
After finishing their coffee, she suggested he come for a small drive
with her. She said she wanted to buy him something 'special'. It wasn't
far away. They pulled in front of a lingerie store called "Naughty but
Nice." They sat for a moment in front of the store. Then Cameron got
out of the car and before Chris new it, she was opening HIS door for him.
It felt weird. Out he came, she grabbed his hand and they both entered
the store. There was nothing but lingerie here, a multitude of items in
every texture and colour.
"Isn't this fun?" she asked him as they walked through the store. He
nodded but was now really sweating, feeling every eye in the store was on
him. She held up several pairs of panties in front of him asking him if
he liked them. He said yes to everything. He wanted to get out of there
now, he was embarrassed.
Cameron bought several pairs of panties and nylons. She asked him to pay
for them at the counter while she tried on some other things. That he
didn't want to do, go to the counter by himself but he did. He felt so
funny in front of the cashier while he handed her the dainty items. "You
have good taste," the cashier commented. Chris just nodded and smiled.
After what seemed forever, Cameron finally appeared at the front of the
store and they both left and got back into the suv. What an experience
that had been, one he would never forget. "You see, Chris it wasn't that
hard to buy something on your own now was it?" He again nodded in
agreement. "Good, next time you can go in on your own. They're very
understanding in this store you know," she commented. Chris was silent,
he just didn't know what to say.
Cameron then drove him back to the coffee shop telling him how good a
time she had and what a great guy Chris was. This time she didn't kiss
him on the cheek but rather on the lips and at the same time her hand
went over his dick ever so lightly. She smiled. "Next time, we will
have to look after that bulge in your pants," she laughed.
Part III (Coming Out)
Shortly after Chris's 16th birthday, he had a big fight with his sister
and mother. He was doing terribly at school and because of this, his
mother had given him an ultimatum. Either improve at school or get a
job. He really didn't want to do either, but decided that school just
wasn't worth it to him, especially with everyone picking on him all the
time. He just didn't feel he belonged. He decided to apply for a job at
an HMV music store. The people who worked at this chain store, were all
a little off the wall anyway, so he hoped that he might be accepted a
little more.
Cameron and him were conversing almost daily now, and when he told her of
his new job, she was excited for him and said she wanted to celebrate
with him. She asked him out on their 'first official date' and of course
he accepted.
This time Cameron gave Chris a couple of instructions. He was to go to
the lingerie store they were at the previous week and do a little
personal shopping. He was to ask for a clerk called "Kory" specifically
for help and she would give him the hand he would need. Kory would also
know what Cameron wanted him to buy.
Chris had never gone into a lingerie store on his own, never mind to buy
things for himself. He assumed she would want him to buy maybe a pair of
panties. It was Kory he was worried about. This was another stranger,
and he was really worried.
Cameron had told him to go to the store at 4.00 on a Thursday and that
she would pick him up at the store around 6.00 and then they would go
out. He was told to take the bus to the store.
After days of anticipation, Thursday finally came. Chris had gone over
and over the scenario that was about to come true. He imagined all kinds
of things that might happen in the store. He was really nervous.
Chris entered the store and was immediately greeted by Kory. Her name
was on her badge and it was obvious she had been expecting him. Kory was
about 30 and very well built and very sexy. There was no one else in the
store at this time.
Kory explained to him that Cameron had given her a shopping list but
before they began she would have to take a few measurements. He stood
there while Kory pulled the tape measure around several parts of his
body. She commented how slim he was and watched as he blushed when she
said it.
Kory then took him over to the panty shelf where there were hundreds of
different pairs. She held out a pair for him to feel and knew by his
reaction that he liked that. "I think these pink panties will do for a
start" she said to him giggling as she held them in front of him. "Now
lets get you a new pair of nylons and garters", she strutted towards the
hosiery section. Kory said that black nylons would be best until he
learned to shave his legs and handed him a pair in one hand and a garter
belt in another.
Before he knew it, Kory had directed him to the fitting room and told him
to go inside and try the items on. Chris was really getting excited. He
wanted to cum so badly just thinking of wearing these things. He heard a
knock on the door! Before he could answer, a black mini skirt was tossed
over the top of the door onto the floor at his feet. "Put this on too,
while I look for a top for you." Chris didn't know what to do now. He
never expected this. He looked at the skirt. There he was in front of
the mirror with his panties, nylons and garter belt on. He was really
getting horny, but putting on a skirt might be taking too much of a
chance. He didn't want to be seen like this.
Another knock on the door, and like before another item came over the
top. This time it was a silk blouse, accompanied by a padded bra! Oh
my God! "Is everything okay in there Chris?" a voice spoke. It was
Kory. "Can I help you with anything?" and then the door opened. Shit,
there was no lock. Kory smiled at him standing there. She reached down
and grabbed all his clothes, tucked them under her arm and said "I'll put
these in a bag for you and give them to Cameron when she gets here." She
then looked at his feet. "Look like a size 8 to me maybe a 9," then she
left.
Chris was really scared now. All he had to wear in the stall was what
Kory had given him and he was having second thoughts now. He looked at
his watch. It was 5.30. "Cameron doesn't like to be kept waiting Chris,
I've found a nice pair of heels for you to wear."
"You'd better get going, not much time left and we still have to do a
little makeup for you to look presentable," Kory spoke again.
Chris was now shaking as he pulled the mini skirt over his nylon clad
legs. The blouse was very feminine and beautiful. It felt like silk.
He put the bra on followed by the blouse, did it up and stared at himself
again. Now from neck to bottom he was female. He couldn't believe it
was him. He just stood and stared at himself, turned around and looked
at his rear. Then a pair of black high heels were pushed under the base
of the door. "Try these on honey, hope the heels aren't too high for
you, but that's all we have in your size right now. You'll get used to
them, they're only 5 inch heels. You'll get used to them in no time and
Cameron will just love them believe me." Kory spoke so calmly, like
nothing was going on, like she had done this type of thing many times
before.
"Are you ready now?" Kory knocked again. She opened the door and there
Chris stood. "Wow do you ever look sexy Chris! Everything looks like a
good fit. You're a natural. Now we don't have a lot of time." She
pulled out an elastic from her pocket, reached behind Chris's head and
drew his hair into a tight ponytail. "Now sit down while I put a little
makeup on you." She wasn't asking anymore, she was telling. Chris sat.
Chris could hear voices outside the fitting room now. Obviously there
were other people in the store now. He began shaking as Kory began
putting eye liner on him, a little blush and then some lipstick to top it
off. "We are just going to have to do something about that hair Chris,
it's really a mess," she said to him standing over top of him. He heard
a horn honking from a distance, it was Cameron. He began to tremble, as
Kory started to giggle. "Don't worry Chris, we'll have you out to her in
a jiffy, just be careful not to trip on your heels." She giggled once
more. He was trapped and he knew it. He never expected to go to this
extent and now he had no options but to walk into a public place all
dressed up in front of other customers. He could hardly speak, his
throat was so dry now. Kory grabbed him by the hand and led him out of
the fitting room.
Shock! Immediately outside the room, sat three woman obviously waiting
for the big show. Kory spoke first, "Doesn't HE look wonderful", leaving
no doubt that Chris was a boy dressed as a girl. Chris almost fainted,
he wanted to run out of the store, by Kory had him by the hand and
wouldn't let go. "Wow, Chris you really look pretty!" one of the women
spoke as they all seemed to be getting a real kick out of this. Kory
then started for the door, not quick enough for Chris as he tried to
manage the heels and could hear their clicking on the hardwood floors
bringing even more attention towards himself. Finally, she opened the
front door of the store. "Goodbye Chris, have a good time and happy
birthday," Kory spoke as he walked towards Cameron's car.
Cameron was smiling as Chris got into the car. "Chris you look
absolutely beautiful and believe me I'm going to make this a night for
you to remember." She reached over and rubbed her hand over his dick.
She then ran her hand up his nylon clad legs. He got an immediate
erection, Cameron was just so gorgeous, he couldn't stop thinking of her.
He just couldn't understand why she would like to see him all dressed
like this, but obviously it was her thing. He wasn't going to complain,
at least not at this point.
"Tell me Chris, have you ever gone down on a woman?", Cameron asked,
knowing that Chris was most likely a virgin in all aspects of sex. He
shook his head. She then started the car and drove to the back part of
the parking lot, where there was more privacy. Her suv was a very
expensive Lincoln top of the line and with a push of a button her seat
went far back and started reclining. She opened her legs wide, she had
no panties on. "Okay, honey bring your tongue over here, and start
licking." She was right, he was a virgin and he had never even thought
of doing this. It was a little awkward but he was able to get between
the steering wheel and her and get down on his knees to service her. A
beautiful aroma came from between her thighs, she was shaved bald. He
had never seen a vagina before, and he could feel his dick getting hard.
She grabbed him by the back of his neck and pulled him towards her
beaver. He began licking and before long he could feel her thrusting
towards him as she grabbed his hair and pulled. Finally she came like a
volcano erupting and almost bucked his head into the steering wheel. He
was a quick learner.
"Let me fix your makeup honey, it's a mess now," Cameron spoke. "Let me
take you back to my place now for dinner."
They drove for about a half hour. Chris sat there thinking of how
strange it was to be in this car dressed as a girl and how he couldn't
believe he had taken all these risks, completely trusting Cameron. There
was just something about her that made you believe in every word she
spoke. As they drove, Chris put his hands on his legs, and felt the
smooth surface now offered by the nylons. He still had an erection. He
was finally going to lose his virginity, or so he hoped.
Part IV (the chat)
They entered an up scale subdivision. Chris was really glad it was dark
as Cameron continued to her home. She pulled into the driveway in front
of a large two story brick home, which looked very expensive. Cameron
hit the garage door opener, opening one of the doors to the 4 car garage.
Chris was impressed and also happy that they would be going into the
garage and finally out of sight.
Cameron got out of the car first, came around and opened Chris's door.
She held her hand to him and helped him out, helping him to balance on
his new heels. "You really do have nice legs Chris, you just look
wonderful," she said again reinforcing to Chris that he did indeed look
good.
They entered the home through the garage side entrance. Of course
Cameron also had heels on too, and the floors were all marble and the
click of their heels in unison excited Chris. Cameron took him to the
living room and told him to relax while she changed. She also pointed to
the 'powder room' where she suggested he might want to freshen his
makeup.
He went to the powder room and looked at himself in the mirror, admiring
the new person that had been created by Kory at the shop. He did look
like a girl now, but he still wasn't sure if he wanted to live like one.
He wanted it to be just a fantasy and now his mind was racing. Cameron
had his street clothes and he knew that he would need them before
returning home.
Cameron suggested to him that he call his mother and tell her he might
not be home tonight so she wouldn't worry about him. He called her right
away, why hadn't he thought of that? His mother took the news in stride
and Chris could tell she didn't care if he was at home or not.
Cameron told Chris she wanted to have a small chat with him when he was
finished in the powder room. This made him nervous. Had he done
something wrong?
He sat on the couch with his legs crossed while she sat opposite him.
She began the conversation by asking Chris what he thought he would want
in his future. She summarized his life to date as basically be that of a
loser. He had no friends, boys or girls, no proper job, had quit school
and really was on the road to nowhere. Chris began to cry as she went
on.
She went on "Chris I think you know by now, that I have no problem with
your dressing, in fact I prefer you dress that way. However, for our
relationship to continue I will have to set a few ground rules for you.
The first rule is that you ALWAYS dress up while in my house. I don't
ever want to see you wearing a single stitch of male clothing. You have
only begun, I am financially well off and believe me I have all the
resources I need to turn you into the person that I know deep down you
want to be.
I want you to seriously consider quitting your job and leaving home and
staying here with me. There is no need for you to work while you are
with me." That said, Cameron stood up in front of Chris and spread her
legs open wide. "Now get down on your knees and and service me." She
spoke in a very domineering tone and Chris knew this was a demand , not a
request. He decided to comply and before long, she was once again
grabbing his hair and pulling him into her sex. There was no doubt who
was in control and Chris wondered if this was how it should be. He felt
funny being a girl and doing this to a woman. He would rather have been
himself having 'normal sex' as he used to think of it. Once again
Cameron climaxed, pulling him into her so hard he could hardly breathe.
For the first time she called him 'Christine'.
Geraldine
- 17.09.2022
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