Debbie Caned
- 3 years ago
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Her First Time Caned free porn video
Her first time Caned
I have been asked by my slave-j if she can have a sister? I have never
considered having a second slave in the house. I would think that having
two female slaves would only cause trouble. I am no longer a young buck
and the thought of two women in the house is just a little disturbing. I
told her that I would think about it. I could tell she was disappointed
with my response.
It was a few weeks later on a saturday I was relaxing on the deck and
slave-j came running up and was about to burst with some news or
something. I made her wait a few seconds until I was sure she could not
stand it any longer. "Ok what is it j"
She was so excited I had no idea what she was attempting to tell me. It
took a few minutes for her to calm down and then she got her message out
clear enough for me to understand her. She was pointing at the boy
cutting the grass and said he could be my new slave. I looked at her and
told her I was not interested in training a male slave. J giggled and
said that the best part of it he is not just a boy he is a she-male wanna
be and is looking for some where to live that will understand and not
give him a difficult time as he transitions.
slave-j has an interesting idea, I have always enjoyed being a voyeur of
she-males and t-girls. I told slave-j to have him come and talk to me
when he is done with the yard.
About an hour later slave-j lead him in to my study and introduced him to
me. His name was andy and he looked like he was about 19 or so years old,
5'3" or so and I bet he did not tip the scale over 125 lbs. Andy told me
he lived at home and his Dad caught his dressing a few times when he was
younger and made him feel like a bad child and it was traumatic for him.
He has always known he was really a girl and it was killing him to hide
the feminine self from the world. I explained what life was like as one
of my slaves and he said he was willing to do any thing if he could be
free to be, "annie" and grow as a woman. I outlined a deal for him and if
he agreed then I would expect him next saturday to come over and
interview for the job as my new slave fully dressed as a woman, he must
show no signs of his male self and he must arrive dressed, fully made up
and his hair done, nails done and pedicure. He also was to bring what
ever he wanted to be hers from her home, as if she was excepted in her
new role she would not be returning home after that day. she said yes Sir
and ran out like the place was on fire.
The next weekend came and slave-j was so excited and she wanted to get me
in a good mood so after she had fixed me lunch she had a nice dessert all
planned and I was sitting at the table when she ducked under it across
from me and soon had her hands working my zipper on my jeans. She made
fast work at getting my cock free form my pants and worked her fingers
around my shaft with her delicate grip and I was enjoying her efforts and
then she wrapped her tantalizing lips over my gland and I was in bliss
just as she had planned. I love the way slave-j takes on her role to keep
me happy. When she was done and had cleaned up me and the dishes from
lunch it was time to meet with annie. I waited in my study and it was not
long before a knock echoed from my door. I invited them in and I was
stunned at the vision of a classy yet hot and sexy woman that glided thru
the door way standing atop a pair of sky high heels and then stood by the
chair in front of my desk. I asked, "Annie?"
She responded, "Yes Sir."
I was shocked with the image she portrayed in front of me, I never would
have known it was the same boy that stood in the very spot a week before.
I invited her to sit and we chatted for close to an hour and I learned
many of the details of the woman that sat before me that day.
I explained what I would require for her and that she was to stay at
least 2 years and I would take care of all her needs and she would do
what ever was needed to keep the house up and me happy. The last thing I
told her was the most difficult of all. She would be placed in chastity
and remain locked up at my whim, she was to always present herself as a
female and that meant she would be up and ready dressed and full make up
and hair done before I got up and she was to always go out as a female,
from this point on Andy was gone not to be seen ever again. With that
said ,she agreed. When she was out of the house she was to never do any
thing to shame her self or the house and if that ever happened she would
no longer be allowed to leave the house and if she committed a second
disgraceful act she would be asked to leave. She eagerly agreed to the
terms and I told her that slave-j will start her training.
The next few weeks were full of training for annie and taking her to the
beauty parlor, buying her clothing and shoes.slave-j has shown her how to
do many of the things that she does around the house and today I had a
talk with slave-j about our new slave. Slave-j told me she is doing great
and has learned fast and loves being here. I agreed and that is when I
told her it is time for you slave-j to teach her the other duties now. I
could tell she was worried at the thought, she knew just what I meant. I
reminded her how I showed her how to give a blow job and please a man.
She just nodded, her eyes told me her true feelings. She could not hide
her fear at what annie's reaction to her teaching her how to suck cock. I
then told her that I would not be happy until annie could preform as well
as she did.
After a few more weeks I told them both that I was going to test annie's
skills out and that I wanted them both showered do their make up and hair
and be naked in my playroom on their knees waiting for me. In 2 hours.
I left to run some errands and when I returned I found them just as I
expected. I went over and stood behind them and petted both of them on
the head and praised how well they looked and asked if they were ready. I
heard in unison, "yes Sir" it made me smile and I went over and sat down
in a comfy chair. I told them I was going to close my eyes and then they
were to pick which one went first. I enjoyed the both of them and even
the fact that annie had never had a cock in her mouth before she did a
very good job, I could tell who was who but I never let them know and
gave them both a big hug and said I was so pleased that she was just as
good as slave-j was, she smiled and I could tell this was going to be a
great new slave to have in the house. I told her that from this point on
she would be called slave-a while she was not in public.
I left them to clean the playroom and I decided that I would reward
slave-a for doing such a good job learning. I knew that a good friend was
coming to town soon and would have a great party for her friends, that
would be the prefect place to let slave-a make her debut. I was really
amazed at how far slave-a has progressed, her looks had never been an
issue and she is now walking more like a woman then most cis women do. I
love the way she crosses her legs and to watch her bend down and pick up
something off the floor is magic . I find myself dropping things around
the house just to watch her bend down to retrieve them. She has been
working hard on her female voice and it still needs some work but it is
coming along nice.
A few weeks later I was walking up to the house and picked up the mail on
the way. I saw a letter from an old friend just as I opened the door and
as always my slave-a was waiting on her knees on her mat by the front
door. Her chain from her collar locked to the ring on the floor next to
her mat. I lean down and kissed her on her for head and drop my key to
the lock, she knows what to do.
I head up the stairs and get changed in to sweat pants and tee shirt,
take a leak and clean up from the day. I hear her moving around down
stairs as I descend to the family room and sit down to enjoy some quite
time and music. On the table next to my chair on the left, slave- a has
placed a tall glass of ice-cold tea on a lace doily. She has a way to
always present her offering in such a delicate way. The tea hits the
spot. On my right kneeling beside my chair is slave-j locked in the same
manner as slave-a was at the door. I hand her my keys and she unlocks her
chain from the floor. I remove her gag and tell her I am very stressed
from work. Slave-j takes my stress away in her very own way and I feel so
much better as her head is busy between my legs I slave-a coming to me
from the kitchen holding a tray of snacks. I love the way my slaves keep
me happy.
I tell her that I have just gotten a letter from Lady Sage an old friend
I have not seen in years, I hand her the letter and she opens it and
hands me the contents. It is an invite to a party that Lady Sage is
having while she is in town, I look at slave-a and ask if she would like
to go? She tries to smile and nods her head yes. I can see a sparkle in
her eyes. It will be the first party I have taken her to and I am sure
she will be just a little nervous. The party is next weekend so she has
time to get ready and use to the idea of being in public as my slave.
Slave-a is my first she-male slave and we both are adjusting she only
moved in a few months ago and being owned is new to her. She has a lot of
duties at the house and she is getting use to not working outside the
house and I think that she is a little lonely since she quit her job.
She has dinner ready and I remove her gag so she may eat with me and
slave-j they can tell me all about their day. I love to hear all about
their daily adventures and today is even more exciting as slave-a went
shopping for the first time alone. She told me that it was a thrill when
she was walking around the store filling her list with all she needed for
the week. (I have rules how she will look when she leaves the house
alone, She may wear any of her vanilla clothes as long as they show her
off and be very feminine. She must wear heels and carry a handbag. If she
wears jeans she cannot have anything in her pockets.) Today she wore her
Laperla Paisley yellow body suit, a red dress that hit her mid thigh and
a black pair of pumps. I love that outfit and she looks stunning in it.
When she was checking out and had to use my credit card she said she was
worried that they would ask her for ID and if they did she would have to
show them her old ID that still had her gender as male.
I smiled and said, "Well I guess it is time that we fix that after all
you need to change your address also, we can go on Friday and get all
that stuff done." She nodded and then filled me in on the rest of her
day. After she put away the groceries she did the wash and cleaned the
house down stairs and finished just in time to change out of her clothing
and put her collar on and be in place waiting for me to get home. I
require her to be naked and put on what ever I have place in her top
drawer that morning. Today I left her a collar and chain, a red ball gag
and bright red pumps. Of course she is always wearing one of her chastity
devices and today she is locked in her Holly Trainer ball trap in pink.
She is adorable dressed this way and I know she craves being locked up in
chastity.
We went to the MVA and she applied for a drivers permit and when the
young lady behind the counter saw her old permit said wow they made a
mistake on you permit they miss marked it they put you down as male. She
made short work of it all and next thing we were walking out and slave-a
had her brand new permit declaring to the world she was female. She was
giddy over her new ID.
The night of the party was here and I left for work in the morning and
left what I wanted for her to wear to the party in her drawer with a
note. I knew she would read it as soon as she got up in the morning, I
let her sleep in today not like other days when I get her up when I wake
and send her to get my breakfast ready. Today I would pick up something
on the way to work.
When slave-a woke up and checked her drawer and saw the note that read,
"after you shower put on the following, A black leather cat suit, a
leather under bust corset, her black knee high heels boots and her black
leather gloves with locking cuffs. Next she put on her leather mask with
built in gag and open eyes with a small collar on top for hair to hang in
a top ponytail. Last she was to put on her locking collar that would keep
her from removing any thing once she placed the small and lock in place
and snapped it closed. I knew once she heard that final click of the lock
under her chin she would be floating in sub space.
I had a note in slave-j's drawer also that read something completely
different. It told her to get completely naked and lock her steel collar
and cuffs set on her. Then she was to have slave-a lock her inside her
bird cage and tether the chains from the cuffs and collar to keep her
from being able to touch herself in any way.
By the time I get home slave-a is kneeling in her spot and the chain to
her collar is locked to the floor, I walk past her taking no notice of
her at all. I go to my room and change into Jeans and black tee shirt. I
check on slave-j locked in her bird cage just as I expected. I gave her a
kiss thru the bars and told her to have a good night we will be back
late. I then put the black cage cover over her bird cage so she could get
some sleep. Then head down and get my black duster and put it on and then
unlock her chain fro the floor and give a short tug and slave-a follows
me out the door to the car. Once in the car I help her with the seat belt
she has a hard time with the heavy gloves. Then I snap her blindfold over
her eyes and I can tell she wants to see but I have other plans.
We pull up to the address and they have valet parking they open the door
for her and to her feet and guide her to the side walk. The female valet
looks so cute holding my slaves chain as I make my way around the car and
grab the lead to her collar from her as I hand her a tip. Again a quick
tug and she follows my lead. Inside we need to take the lift to the top
floor. I feel her pull back as we enter the lift I think she is a little
scared of the sound of the small space. Soon we feel the movement and she
leans against me I wrap my arm around her waist to steady her.
We are greeted by the hostess and then head in to the party. I see lots
of friends and then I see Lady Sage. We talk and catch up and soon her
attention is drawn to my leather-clad slave.
Sage says, "What a wonderful vision she is, I would love to cane her very
round behind."
I tell her that she is welcome to take her and enjoy her just make sure
she returns her in one piece, she agrees and hand Sage the leash and her
keys. I watch them as they make there way to the dungeon. I mingle with
some friends and after a bit I find my way to where slave-a is and for
the first time I get to watch her be played with by my friend. She is
standing by a set of stocks and Sage has begun to remove the leather cat
suit and soon find her surprise and turns to me and has a giant smile on
her face. "I had no idea she is delightful and do I have the keys to her
belt."
I shake my head no and smile back. I see her guide her head into the
stocks and then her hands before she slides the stocks closed and locks
it in place. My slave is now locked in the stocks bending at the waist
and only has on her pink chastity device and a leather hood and
blindfold. Her skin is so beautiful and I feel slightly unsettled knowing
what is about to happen.
Sage picks up a cane and with her free hand she begins to stroke my
slave's ass softly and I can tell she is enjoying the attention and the
feel of the soft-gloved hand on her ass. She has no idea what is about to
happen. I see Sage raise her cane and hear the whistle of the cane as it
lands on her virgin skin with a snap and the jolt of her body and with
out any delay comes the second strike and it lands just below the red
strip already showing on her ass. The sounds from the cane and moans from
slave-a have not gone unnoticed by others at the party and soon a crowd
has gathered to see the new slave take Sage's cane. It is not long before
her ass is covered with welts and strips yearning to be welts when the
cane slows and now is lightly stroking her ass, almost like Sage was
gauging her readiness to endure more or was she at her limit. I see Sage
lean down close to my slave's head and linger at her head for some time;
I guess she is talking to slave-a. The she moves behind her and Sage
raises her leather dress exposing the very beautiful alabaster skin of
her derri?re and slowly she moves closer to slaves-a's burning red welted
behind and presses her to cool flesh to the fire that her caning has
stoke in slave-a ass. I could swear I saw slave-a relax her body as her
skin was soothed by the touch of that magnificent lady's derriere. The
crowd let out a moan as they witnessed Sage's munificent gesture to sooth
her heat.
I was sure they were done when Sage began to pay attention to her breasts
and as the cane slowly wondered over her nipples slave-a became very
still and I am sure that she had the same thought I did. Was Sage about
to cane her nipples? To my surprise that was not where this was heading.
But the effect it had on her was astonishing she began to quiver and then
for the first time since I locked her in her belt she exploded in delight
as her juices flowed down her legs. Then her knees buckled and Sage had
to hold her up to keep her from choking and called to me for help. I held
her and Sage unlock the stocks and we lowered her to the floor and I back
away letting Sage hold her and calm her down as they cuddled below the
stocks.
After many minutes Sage had her up on her feet and soon had her dressed
and back locked in her leather encasement and lead her by the leash back
over to me.
"She is a delight Sir and thank you for loaning her to me I enjoyed her
very much. You are a lucking man to own such a delightful and special
young lady take good care of her."
We had some pleasantries while slave-a was standing very still next to me
and at one point I reach over to pet her ass and the heat coming thru her
leather suit was unbelievable. I could only imagine what was happening
inside her. I could hardly wait to get her home and release her to get a
closer look and hear her thoughts on the night.
I walked around for a while longer with her close behind me getting all
great comments and compliments on my slave and her scene with Sage. I
could tell she wanted to tell me something but I was enjoying her
frustration and plight of this evening's events.
When we got home I removed her blindfold and could see the evidence of
her tears and her eyes pleaded with me to let her talk. I removed the
gloves and the boots then helped her out of the cat suit. Leaving her
standing in front of me naked with her pink prison on and her hood and
gag.
"Slave it is late and I need sleep I want you to get ready for bed and
meet me at the foot of my bed when you are done."
When I came out of the bathroom she was on her knees at the foot of my
bed. I take her wrist and cuff them to her collar and replace her
blindfold. Then I help her to her down on her back. I open the cage door
under my bed and slide her inside the cage and before I lock the door I
pad lock her ankle cuffs together and push her in a bit more and lock the
cage door.
I do not want to sleep alone tonight so I head over to slave-j's cage and
I wake her and set her free from the cage. I lock her steel cuffs behind
her back and walk her to my bed. And tel her to lay down.
I climb into bed and find that slave-j is very frustrated after being
left home tonight and is soaking wet with passion. I remove her gag.
slave-j asks if I will unlock her chastity belt so she can have sex with
me and I tell her why is your mouth not working and she goes down on me
and gives me a wonderful oral kiss goodnight while slave-a can only
listen to the passion of our sexual encounter just inches from her prison
below my bed. I fall into a blissful slumber.
It has been almost a year since slave-a joined our household and I have
learned so much about her. She has slept under my bed now many nights, I
have heard her cry from time to time, always wondering why she had some
sad nights. I asked slave-j one day and she looked like I had just stolen
her virginity as she made a feeble attempt to dance around my request. I
told her to spill it or she will spend the next 30 days in the box,(the
box is a coffin with a trap door and head stock that is very intense and
she has spent a few days in it before) the mere thought of a stay that
long was more then was needed to make her a chatter box. Slave-j told me
that annie wished she had been born a girl and at times felt like she was
less then a person because of her birth gender. I could only imagine how
hard it must be for her having to deal with those feelings.
A few days later I called annie into my study and ask her to sit down and
relax, she was very rattled just by me calling her in and I did my best
to calm her down.I told her I knew why she cried at night and I asked her
if I could help. Her eyes filled with tears and she did her best to say
that she wished I could help her but it was natures mistake and it would
take a miracle from gods hand to fix her. I told her I may not be god but
I sure could fix his mistake. I handed her a card and explained that she
had an appointment for the next day with a psychiatrist who was a trans
gender specialist and once she approved annie for SRS I would send her to
a clinic in canada that would complete her transformation and I would pay
for the whole thing.
This chapter closes
I crave your reviews please good or bad I love to hear from the readers
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