Chelsea Starts School
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Chelsea Starts To Work For Ms. Jessica free porn video
Chelsea Starts to Work for Ms. Jessica
By Sissie Maid Cuckold
"No, you may not wear your formal Uniform Chelsea. You know it is only
for serving at formal get-togethers. Now get changed into one of your
morning uniforms and report to me immediately!"
"Yes Ma'am, right away Ma'am." Chelsea curtsied and hurried to her room
to change. A room that she had just been assigned by Jessica and had
only finished putting away her uniforms minutes ago. Chelsea loved
wearing the Formal Maids uniform. What sissy wouldn't? They are so fun
to wear and move and bounce and impart feelings from the petticoats
that other outfits do not. But Jessica could see she must set limits
and put her foot down before Chelsea became a problem.
Jessica secretly smiled at how girly Chelsea had become. How much she
actually wanted to be treated like a submissive underling and most of
all as a girl. She did not have the experience to understand that once
a pansy male accepts his new role he often dives into it immersing
himself so deeply that he becomes more feminine in mind and action than
the most feminine of real women.
In Jessica's world, women were becoming more masculine in so many ways.
In work, in hobbies, even in dress. Oh, they were not cross dressing to
be men but most preferred to wear pants instead of dresses, bear legs
in stead of nylons, sensible shoes instead of 6" spike heels. But not a
true sissy. A real sissy wants all of the most feminine of items.
Frills and lace and as far from masculinity as possible.
Ms. Reynolds understood these things. She had dominated a pantie waist
husband and turned him into her willing and capable sissy maid. She
learned first hand how valuable it is to totally feminize and remove
ALL vestiges of masculinity from the pansy. It was not only for his own
good but hers as well. She learned that the more domination and
sissification that was heaped on him the better he felt and the more
she enjoyed dominating him. Oh, it was a bit difficult in the beginning
when she worried that it might hurt him or be harmful to him. She loved
him and did not want to hurt him in any way. But like Chelsea he was
not a real man and the real hurt was him having to pretend to be a real
man. He simply did not have it in him and once it was forcibly taken he
was much happier and better off. When she forcibly took his
masculinity, it was truly not by force, he could have stopped it and
would have had he been a man but he knew what his wife was doing was
the right thing so while he may have put up a whimper or two the fact
is he truly wanted her to take control as all sissies do and hope for.
Even if they don't admit it or know it.
Chelsea was much like many other sissies who try to control their owner
from the bottom. Jessica was not going to have any of this. Chelsea was
going to become her very proficient sissy maid but she was also going
to become her very compliant, submissive, subjugated sissy maid and
there was no time like now to get her started down the right path!
When Chelsea reported back to Ms. Jessica she had a big smile on her
face and curtsied. Jessica loved to see her curtsey and it took her for
a moment but she quickly recovered.
"Chelsea, kneel before me!"
Chelsea did not understand but obeyed.
"Look up at me...the distance I stand above you is how much smarter I
am than you. It is how much more powerful I am than you. It reflects
our relationship perfectly by showing you how far above you I am. Do
you see and understand this Chelsea?"
"Yes Ma'am."
"Chelsea you seem to think you can develop a mind of your own. You know
the rules and you most certainly know as good as anyone what uniform
you are to wear at what time and for what job. You did not display that
knowledge a few minutes ago, now did you Chelsea?"
By now Chelsea was beginning to understand the gravity of the
situation. His smile had faded away into a very serious and somewhat
concerned look. "No Ma'am, I did not."
"This is your first day Chelsea so I want us to get off on the right
foot. I do NOT want to have to remind you of the proper uniform to wear
again or there will be serious consequences for you, is that clear?"
"Yes Ma'am, I am very sorry Ma'am it won't happen again Ma'am."
"It better not or you will be a pantie waist without a maid's job, are
we clear?"
This scared Chelsea, she had not really even started work for Jessica
yet and she was on the verge of being fired! "OH Ma'am, I won't let it
happen again I will mind my place Ma'am, I promise."
"You better young lady, you better! Now get to scrubbing my kitchen
floor I want to see what you have learned from Ms. Reynolds!"
Chelsea rose up, curtsied and almost ran to the kitchen. Jessica had to
remind herself to never let Chelsea know exactly how much her curtsies
affected her sexually or Jessica could possibly curtsy non-stop and
take over! No, she would never let it come to that but still it was
amazing how it made her clit tingle each time Chelsea performed a
curtsy.
Jessica gave Chelsea a few minutes to get her hot water, soap and wash
rag ready and then moved to the kitchen entrance to observe the pansy
at work. She was pleased to see the girl on her hands and knees
scrubbing like an experienced scrub maid. It pleased her to see the
wimps bottom wiggling and his skirt swishing. It sort of mesmerized her
and she fell into a sort of trance. In her mind she was standing behind
that pantied bottom holding on to his hips and pegging him with her new
strap on. She caught herself becoming excited about it and blinked her
eyes fast to bring herself back to reality. What was coming over her?
She wondered out loud saying, "What am I doing, this is consuming me?
Snap out of it she is your maid."
She started to turn away and then turned back and said, "Report to me
when this floor is perfectly clean!"
"Yes Ma'am." Was the response.
Chelsea scrubbed and scrubbed with all his skinny little weakling arms
could muster. He washed and rinsed and then did the entire floor a
second time just to make sure of his work. When he was done he put the
bucket and rag away and reported to Ms. Jessica.
Curtsy. "I am finished Ma'am."
Jessica looked him over. She noticed that the front of his maid's dress
had wet sports and he was some what flushed from the effort he had put
into the job. The pansy presented the perfect image of a hard-working
maid and this pleased her.
"Is my floor clean?"
"Yes Ma'am, I washed it twice to make absolutely sure it was clean."
"I see, why did you think it necessary to wash it twice?"
"Because of your words Ma'am, you said it must be perfectly clean
before I reported to you. I did not wish to displease you in any way
Ma'am so I washed it twice to make sure it was as you wished."
Jessica almost smiled at his remark. It was most certainly one of a
very subjugated sissies but she did not smile, she did not want to cut
him any slack yet. He needed to learn his lessons and place first.
"I want you to examine my shoes for cleanliness."
Chelsea looked down and said, "Yes Ma'am," at the same time. He dropped
to his knees and began to examine them.
"Check the bottoms of the soles as well."
Chelsea very carefully reached out and picked up Ms. Jessica's foot and
looked under it.
"Well?"
"They need to be cleaned Ma'am." Chelsea started to rise.
"Where are you going?"
"Oh, I was going to get a rage and water I thought..."
"No Chelsea, my shoes will not be touched by some scrub rag. A lady's
shoes deserve to be gently and properly cleaned. Have you ever heard of
a spit shine?"
"Yes Ma'am."
"Do you know how to do that?"
"I believe its when a person spits on a rag and rubs a polish shoe to
bring it to more of a gloss?"
"No, you do NOT spit on a rag. Did I just not tell you no rag was to
touch my shoe?"
"Yes Ma'am."
"As my ladies' maid Chelsea, you will use only your tongue to clean and
shine my shoes. By using your tongue, I know you will give my shoes the
proper care and attention they deserve. Now pick up my foot and start
cleaning my shoe. When you get done with one do the other and they
better be perfect young lady!"
Chelsea swallowed hard at this command. These were the shoes that Ms.
Jessica had worn all morning. Out shopping and walking and driving. But
he dared not resist know he was already on shaky ground and while
rather reluctantly and slowly he began to lick the sides of her shoes
while holding them with her feet in them. After doing one side of one
shoe a feeling started to overcome him. One of blind obedience combined
with an enthusiasm he did not expect. It was if the shoe was calling
him making him lick it. It was a rewarding feeling but none the less
his tongue began to feel stretched and dry and worn by the time he
cleaned both of her shoes. He was actually pretty sure his tongue was
stretched about two inches! It certainly felt that way. It was also
quite dry so when he tried to talk to tell Ms. Jessica he was done it
was as if his tongue was still completely outside his mouth! It was
most certainly a strange experience all around for Chelsea.
"I, I, fished, clning our oes Ms. Yessica."
Jessica almost burst out laughing at how corrupted his words came out.
She had wondered about how it might affect him doing all that licking
on her shoes and even cleaning the soles. It must be rough she thought
but he is not complaining so, Oh Well.
"Very good, now go to my room and chose an other pair of my shoes and
bring them here please."
Chelsea rose, curtsied and did as told soon returning with a pair of 5"
red strappy heels. He curtsied.
"Nice choice, these are one of my favorite pairs of shoes I love to
wear them on dates, they really turn the guys on!" As soon as she said
it she thought maybe this was not a proper conversation for her to have
with Chelsea, it may make him feel bad but then she recalled what Ms.
Reynolds had said about finding real men to fill those special needs so
she thought, no he will learn it all.
"Put them on my feet Chelsea."
Chelsea knelt and removed Jessica's shoes setting them carefully off to
the side. Chelsea noted and liked the respect he was showing to her
shoes. He then very carefully put the red heels on Jessica using the
same care and respect he had shown for the pair he had taken off.
"Good little sissy. You did a fine job removing and putting on my
shoes. Now, clean them!"
Chelsea's eyes got big at these words. Oh, it was not that he was
against the order it was that he was not sure if he would be able to
walk without stepping on his tongue when he finished. He swallowed hard
swallowing both his pain and any male pride he may have had left and
lowered his head and began to tongue wash Ms. Jessica's shoe.
Jessica had gotten turned on while Chelsea was cleaning her other shoes
but now it was even hotter as these were strappy heels and Chelsea's
tongue often caressed her foot as he cleaned the straps and inside
edges.
She was sitting such that she could observe the sissy doing his work
and the sight was a total turn on for her as well. When she saw the
prissy boy licking her heels it was too much for her. "Chelsea, you
don't lick heels you suck on them. Place the entire heel in your mouth
and suck on it, moving it in and out of your mouth!"
Chelsea did not hesitate and in fact found it a nice change from
stretching his tongue out. He had no clue how this appeared to Jessica.
She suddenly compared it in her mind to a cock going in and out of a
mouth. She was seeing her sissy maid sucking a cock and her sexual
excitement was at a record high. One little breeze or touch on her clit
and she would have climaxed for 20 minutes straight nonstop. She had to
keep control. She tried to think of other things, non-sexual things to
bring her excitement level down but it was difficult. Finally, she had
to just stop watching him. It helped a little but she could still sense
everything he was doing by feel.
When Chelsea had finished his job and non-too soon for Jessica's sake,
he reported.
"Ah M, I, a fised 'am"
Nothing he said was discernable. His tongue was in pain. It was dry,
rough, stretched and abraded. He simply could not speak properly.
Jessica loved it, though she said nothing of the sort to Chelsea.
"Go change your uniform to an afternoon uniform and report back I want
you to fix lunch."
Curtsy, "S 'am".
Chelsea was relieved to be done cleaning shoes. Oh, he would have
gladly done more had Madam asked him to but not having to continue was
certainly his preference. He kept twisting and turning his tongue
trying to re-hydrate it and shrink it from the size of a football (well
that's how it felt anyway) down to a normal tongue.
He soon returned and curtsied.
"Do it again."
"'am?"
"Curtsy. Curtsy again."
Chelsea complied and Jessica knew she was playing with fire with her
clit by having him do this. But it made her feel so superior and
powerful it was addictive to her.
"What is the first thing you do before preparing my meals?"
"Ah, ash mi ands?"
"Very good, yes. Go do that and I will follow."
Chelsea washed her hands thoroughly and then presented them palms up to
Jessica for inspection. A clear act of submission that Jessica noted.
"I want a chef's salad for lunch. You will find all you need in the
fridge. There is a chicken breast you can cut up for the meat, croutons
are in the cupboard to the upper left of the stove. I will have Italian
dressing today. Now make it."
Chelsea went to work, first he put two strips of bacon on to fry and an
egg into hard boil. Then he began cutting up tomato, cucumber and
lettuce. He followed these by cutting the chicken breast into small
pieces followed by green onions and three types of cheeses. When it was
done he put them all into a large bowl and tossed it to mix it up. When
it was properly mixed he placed it into a salad bowl and poured some
dressing over it. He chose a fork from the silverware drawer and took
it to the table where Ms. Jessica was seated.
He curtsied and said, "I hope you find your lunch enjoyable Ma'am."
She looked at the bowl, picked up her fork and tested it.
"You have done will little sissy girl. After I am done eating I will
give you the surprise I promised you. Now assume your station."
Chelsea knew what this meant and quickly chose a wall to stand against.
Folded her hands on her apron and lowered her eyes to the floor in
submission. Jessica smiled to herself.
She enjoyed the mix of the salad that Chelsea had prepared, especial
the three cheeses he used. An American, a cheddar and a swiss. She did
not normally have croutons in her chief's salad but that was a nice
addition as well.
Chelsea stood against the wall as if she had been put away. A very
humbling experience for any sissy. When standing in this position they
understand they have been put away but were still available for
service.
"I will have a cup of coffee now, two sugars and a little cream."
Chelsea curtsied and hurried to perform her task then returned to the
wall while Ms. Jessica finished her meal.
When she was done eating Ms. Jessica said. "I am finished now Chelsea,
that was a very good salad. I want you to clean up then come to my
room."
"Yes Ma'am."
Jessica proceeded to her room and put the strap on. It was a bit
cumbersome at first but she figured it out. It felt soooo good to place
the portion of the dildo meant to be inserted into the woman wearing it
up in her, though in retrospect, she wished she had warmed it first.
She laid out the arm binder and the gag and sat on the bed waiting for
Chelsea.
She did not have long to wait and there was a knock on her door.
"Enter."
Chelsea came in with eyes cast down and curtsied. It was as she
finished her curtsy that she noticed that Ms. Jessica was naked and
wearing a cock between her legs. Her eyes got big as she looked up and
into Jessica's eyes.
"Come here and turn around...put your arms behind you."
Jessica proceeded to fasten Chelsea's arms behind her. Again, it was
somewhat awkward not have ever used an arm binder before but she soon
managed to have Chelsea's arms secured firmly behind her back.
"Turn around my little pantie waist... open your mouth."
Chelsea blindly obeyed not know what was going on and certainly not
having enough backbone to offer any resistance or even question what
her employer was going to do.
As Jessica placed the penis gag into Chelsea's open mouth she had
flashbacks to Chelsea sucking on the heel of her red shoes. It made her
hot and aggressive.
"A good little sissy must learn how to suck on things, don't you think
pussy boy? Like heels and cocks. I mean what if a boyfriend comes by
and he needs his cock cleaned? A good little sissy maid should know how
to clean it, don't you think?" Jessica stared into Chelsea's eyes as
she teased him with this question. To her enjoyment the pansies eyes
got huge as he nodded his head in agreement. Jessica knew that he
probably did not agree with her statement but that was of no matter, he
answered the way she wanted him to answer and that most certainly was
what did matter. As a sissy he needed to learn to answer all her
questions in the manner she wanted them to be answered. His personal
thoughts were really of no consequence and the sooner he learned this
the better off he would be!
"Now, I want you to pretend this is a real cock in your mouth and suck
it like your job depended upon it!"
Chelsea could not talk in intelligible words because of his sore tongue
prior to having this dick stuffed in his mouth and now there was not a
chance of it.
"Do you like my cock?"
Chelsea looked down at the cock jutting out from between her legs. It
was at least twice as big as his. He looked back up at her with very
scared eyes and again nodded his head favorably to her question.
"From what your mother and sister have told me this is way bigger than
your little dicky. But then your little dicky is part of what got you
into dressing and acting like a sissy isn't it?"
Again, a nod in response.
"Well in this house as in all other houses there must be a dominant
partner. Since you are not man enough to play the role of a real man
with a real cock, then I must take that role and treat you as the house
bitch. Yes, you little twerp, I am going to make you the house bitch by
fucking your sissy brains out. I mean really, there probably are not
that many in there to fuck out anyway but none the less that is what is
about to happen to you. Now turn around and get up on the bed put your
head down so your bottom is fully accessible to me for my pleasure.
Oh, and the way this works is, I will fuck you till I cum. If you can
cum prior to that then good for you if not then you will endure what so
many women must endure from premature ejaculation and just simply have
to wait till the next time and see if you can get it then. Are you
ready?" Jessica asked a rhetorical question. She cared little if he
were or not. All she knew was she needed to get her fake dick in this
sissy boy's bottom so SHE could get off. She was way over excited and
needed relief real fast.
She lubed up his bottom and the dildo and with one hand on his hip and
the other guiding the dildo began to press it in. Chelsea tried to move
forward to resist the penetration but he could only go so far and soon
the dick was entering his anus. It hurt because he had no idea how to
relax and Jessica was in no mood to stop or slow down. Once she got it
all the way in she relaxed and allowed him the same. He partially
relaxed but not completely and when she began to move in and out of
him, his hole was still trying to fight the intrusion. Jessica was
feeling the effects of the inserted dildo on her clit and this was
controlling everything now. She pumped faster and faster and it felt
wonderful to her and was beginning to feel good to Chelsea too.
Jessica really got into it, the power, the control, the domination, the
visual stimulations for that morning all had tremendous effect and soon
she was pounding the pantie waist ass like a man on a mission! It was
only a short time later that she began to cum and cum she did. Over and
over and over. It felt so wonderful. But while Chelsea was quite well
stimulated she was unable to cum. Oh she wanted to, she wanted to so
very much.
Jessica finally stopped and came over and over pressed against Chelsea.
Then all stopped and Jessica rested thinking about this new experience.
Then Jessica began to move again and this time more slowly and
methodically. The hurry was out of it and it felt much better to
Chelsea. Jessica talked to her this time saying things like. "I hope
you are enjoying that cock in your mouth one day soon I am going to be
fucking you like this while you suck on a real Man's cock, wont that be
fun?" and "I think I will fuck you every day you work for me as soon as
you arrive and then before you leave again but of course unlike your
little toy dick mine will grow over time. Its only 6" now but I can see
it growing to at least 8" sissy girl. I bet you can't wait to beg for
my 8" cock, can you?"
Chelsea was right on the verge. Oh, she wanted to cum, no it was more
like she needed to cum. The actions and the words were turning her on
so much she could hardly sand it. Unable to move or talk she felt
completely helpless. The things Jessica were saying seemed to be real
and certain. She was living what Jessica was saying. She did not care
to think it out. She simply saw it as inevitable. Her mother and sister
had shown her point blank there was no sense in resisting so in effect
they had broken the sissy bitch to be totally submissive.
Jessica was getting close her self again and was pumping faster and
saying even more daring things like, "I may just have to find a boy
friend who will want you to suck his cock. Then you can clean it nicely
by licking it and licking his sweaty balls while I watch and take
pictures. What will I do with the pictures? Oh, I guess I could show
them to others like your mother, Darla, Ms. Reynolds and maybe even
give some copies of them to Cindy. What do you suppose Cindy would do
with them? I don't know but I bet she would sure have fun with them.
When a sissy hears things like this it makes him sexually excited. The
more devastating the idea is the more it turns them on. Its not that
they want it or even would like it but the thought of it makes them so
completely submissive that they succumb to the suggestion. Done over
and over they actually begin to crave these things even though they may
be embarrassing and humiliating and Chelsea was simply a sissy who was
subject to all of these effects and somehow Jessica could sense this.
She was excited by these prospects herself but she could feel Chelsea's
excitement in how he was now meeting her thrusts and moaning and
wiggling.
"Chelsea sweetie, I think you want all of these things to happen. The
real cock, the photos, Cindy and I want to please you like you are
pleasing me so unless you say right now in clear plain English that you
don't want me to do these things to you I am going to plan on doing
them and real soon. So, go ahead baby if you don't want me to say so or
forever hold your piece and I will do them. No need to ok them just say
something if you don't want me to."
It was so surreal, Chelsea tried to say no, she tried to scream no but
between her sore tongue and a mouth full of cock there was no way. This
both terrified and excited her. She believed that Jessica would do
these things and do them soon. Suddenly her helplessness and submission
was all to much and she began to cum. Cum like a girl. Jessica felt it
and it excited her even more and she too began to climax. Jessica had
no felt the power of dominating a sexual partner. The sort of feeling a
real man gets when he makes a woman climax and beg. A power that a
woman never gest to experience until she pegs a male. They came
together over and over It was the most amazing experience either of
them had ever enjoyed. Chelsea had climaxed a wonderful deep wave of
feminine climax while Jessica had experienced the power of fucking
someone into submission.
After some time in coming down and relaxing from all the straining and
emotions involved. Chelsea felt overwhelmed. She began to tear up.
Jessica thought she was in pain so she carefully pulled out of the
sissies' bottom. But Chelsea began to sob making Jessica feel bad. She
started to feel guilty and softly began to stroke Chelsea and asked her
what was wrong. Even though Jessica asked Chelsea the question she felt
she already knew the answer. She knew Chelsea was going to say she had
been hurt badly.
"Nothing...nothing is wrong."
"Now Chelsea a sissy does not just simply cry, there must be a reason.
Tell me?"
"No...you will get mad at me if I tell you."
"No, I won't. I want to know. Now tell me or I will get mad!"
"I am afraid, afraid if I tell you it will end our relationship."
"I promise you if you tell me the truth it will not end our
relationship but if you hold back from me it most certainly will."
"Sob, sob, ...I love you. There... now you know."
"You love me? That's what you were afraid to tell me? Why are you
crying about that?"
"I, I am just a sissy and I was afraid if I told you that you would get
mad at me because I am not a real man and you deserve a real man but I
can't help it, you treat me so, so perfect that I just can't help but
love you Ms. Jessica...please don't hate me for it."
"You silly nut. I would never hate you for loving me. You see sissy
girl, I love you too."
"You do?"
"Yes, I most certainly do."
"But...not a like a woman loves a man?"
Jessica thought a second. "Well maybe not I think it's better than
that, more important for sure. I don't think I could love a real man as
much as I love you."
Chelsea started to cry again.
"Now what's the matter?"
"I am just so happy Ms. Jessica, you have made me so happy. I never
thought anybody would ever love me."
"Why? Because you are a sissy?"
"Yes!"
"That's just silly. You just needed to find the right woman who
understands and appreciates all the wonderful things a sissy has to
offer."
"But I always thought women wanted real men?"
"Well that's what women have been led to believe they wanted. But once
you get to know what a sissy is good for...well, they actually have a
lot more to offer than any ol real man. But now Chelsea just because I
love you it does not mean I don't want to enjoy a real man now and then
to satisfy certain needs a woman has that only a real man can satisfy."
"I know, I know you need that but is there really a place in your life
for me?"
"Yes, Chelsea there is and that is what we are doing here now. Teaching
you that place."
Hortense
- 31.07.2022
- 12
- 0
Chelsea and Jessica go Uniform Shopping
- 2 years ago
- 17
- 0
Chelsea begins training for marriage
- 2 years ago
- 8
- 0
