Chelsea Starts to Work for Ms Jessica
- 2 years ago
- 25
- 0
Chelsea And Jessica Go Uniform Shopping free porn video
Chelsea and Jessica go Uniform Shopping
By Sissie Maid Cuckold
Knock, Knock, Knock... "Oh hi Jessica, won't you come in," said Carrie
Williams, "what do we owe this pleasure to?"
"Oh, I'm here to take Chelsea shopping...shopping for some maid's
uniforms, is she here?"
"Oh, yes, I see, well yes she is down the hall in the laundry room
ironing her new maid's uniform, she is obsessed with that thing if you
ask me. Go ahead down and see her."
Jessica smiled and proceeded down the hall to the William's laundry
room where she saw Chelsea meticulously ironing her sissy maid's
uniform. Chelsea was unaware that Jessica was standing behind her
watching her iron. Jessica was getting that nice feeling in her clit
again, very similar to the one she got when Chelsea curtsied to her.
She was fascinated by how much effort and attention Chelsea was giving
the uniform. She liked what she saw and finally she said, "Chelsea, I
am here to take you shopping."
Chelsea quickly turned around with a great big smile on her face and
said, "Oh Hi Ms. Jessica, you came, you are really going to take me
shopping," and she threw her arms around Jessica and hugged her
warmly. Jessica was struck by how excited Chelsea was to see her.
"I was watching you iron Chelsea, you do a very nice job. I would like
to watch you iron some of my things while you are in your maid's
uniform."
"I could change Ms. Jessica, it wouldn't take me long."
"No not now besides this is your uniform for when you are working for
Ms. Reynolds. We are going shopping right now so you will have maid's
uniforms to wear when you are working for me in my house."
Chelsea smiled brightly. "I can't believe my luck, two sets of
beautiful maid's uniforms and I will be a real maid for you to. Oh,
this is so wonderful!"
"Chelsea, why are you so excited about being a maid? What is it that
you like so much about it?"
Chelsea got a very serious look on her face. "No one ever said
anything nice to me before I was a maid. They always made fun of me or
put me down. I never looked proper and now I experience what all the
rest of you do, I get praise and a sense of accomplishment. People
like how I look in my uniform. I guess, well I guess I am somebody
now!"
Jessica's face dropped! She had never stopped to think about what it
must be like for a boy like Chester. Tiny weakling body, feminine
features, not good at sports or smart in class. Not only put down by
all the boys but all the girls too even herself at times. She felt
horrible and for a second wanted to tell Chelsea she was as much of a
man as anyone but came to her senses. No, she thought, he was a runt,
he could not be a real man, there was just no way. How could a 5' 115-
pound weakling ever stand up to real men? They would pummel him! Even
every girl she knew was bigger and stronger and faster and smarter
and...No Chelsea was right. They all saw him different now. They
appreciated him as a maid and she was going to capitalize on that and
that is what would make Chelsea have pride and self-worth.
She did promise herself to never put him down again. His comments made
her feel almost sick to her stomach with remorse for how she had
treated Chelsea and her treatment was far, far less bad than the
others. Suddenly Ms. Reynolds words flashed back into her mind and how
she talked about helping him but DO NOT treat him as or expect him to
be a man! NOW, she understood!
"Chelsea, you have amazed us all with your maid abilities and everyone
does think you look proper in your uniforms, it is pretty amazing and
I think it has opened all of our eyes as to your purpose. I know it
has mine. And Chelsea, I want to apologize for any thing I ever said
to make you feel bad. There is no excuse for that sort of behavior on
my part and I hope to make it up to you. I am going to do all I can to
help you succeed as a sissy maid and I hope you will one day become my
permanent sissy maid full time, that is if you can forgive me."
"Forgive you for what Ms. Jessica? There is nothing to forgive,
besides I really, really, really would love to be your maid full time
that would be like my biggest dream come true. I always thought you
were the prettiest girl in the whole school and I always wanted to go
out with you but I knew you were way to far out of my league to ever
ask. The boys you dated were all way above my class that's for sure.
So being your maid is like really the best!"
Jessica almost cried on hearing and thinking about all these things.
She looked ta Chelsea as her eyes started to swell up and hugged him
and said, "You know what, you silly sissy?"
"What Ms. Jessica?"
"You don't see any of those real men here now do you? And you don't
see my arms warped around them hugging them now do you? And you don't
see me taking them shopping or asking them to be my maid now do you?"
"No Ma'am!"
"Then... you goofy girl, don't you just think I might care more about
you than I ever did them?"
Chelsea started to cry, never ever had he felt loved before. Now with
Jessica holding him so tight he was feeling like someone did care
about him. He had gotten a taste of support and caring from Ms.
Reynolds but this was so much better. He could not stop the upwelling
of tears and started to cry. Jessica felt it and broke off her hug and
looked at him.
"What's wrong Chelsea?"
"Nothing is wrong Ms. Jessica, nothing."
"Then why such big tears?"
"Cause I am so happy, I never knew anyone cared about me before. I
just thought I was alone in the world. Its probably hard for you to
understand but you have parents that love you, friends and people who
care but well...I never did till yesterday when Ms. Reynolds helped me
and now you."
Jessica took the poor sissy back into her arms and hugged and patted
his back as she said, "that's all changed now Chelsea, Ms. Reynolds
and I talked and she really does care about you and so do I. Your
mother and sister do to Chelsea they just don't know how to show it
yet but they will, I promise you they will."
"Really, you think they will? That would be wonderful, you know
Jessica its pretty hard when your own mother and sister don't even
love you. I wish they would I wish they would see I am worth loving."
"Chelsea, you listen to me and you listen good. You are a wonderful
person, sure you're a... you're a..."
"A sissy I am a sissy!"
"Well yes you are but that is not what I was looking for. You're a
caring and loving and kind and gentle person and the world needs more
people like you. You just listen to Ms. Reynolds and me and you will
see that you are worth a lot more than anyone thinks!"
"Really? You think so?"
"Yes, I do and I also think you better get your little pantie covered
butt in the bathroom and fix your make up so we can go and find you
some proper uniforms!"
Chelsea smiled and wiped her sissy tears. Her mascara was already a
total mess and she ran to the bathroom feeling ever so wonderful.
Jessica followed and watched intently as Chelsea worked at repairing
her make up. Chelsea was pretty good at applying it. her mother and
sister had seen to that making her do it over and over until it was
perfect. This was another one of those times she hatted to admit it
but her Mother and sister had been a help in training her to do her
makeup properly.
"Wow Chelsea, you are really good at putting on makeup, I am
surprised."
"Well I got a lot of unwanted practice."
"Mother...sister?"
"Yup and I hated it but I guess it paid off right?"
"It sure did, you are really good at it."
"Thank you."
"Well you look great now, lets get going I am not sure where all we
will have to go to get what we need."
Jessica and Chelsea walked to her car. Jessica watched Chelsea get in
to see how she got in a car wearing a skirt. Chelsea opened the door,
backed to the seat, brushed her skirt under her bottom, sat down then
lifted her feet together keeping her knees together and turned in the
seat planting her feet on the car floor. Jessica smiled and said to
herself, "Good girl Chelsea you know how to sit in a car while wearing
a skirt." Chelsea turned to look at Jessica and Jessica simply smiled
an approving smile back at her.
Jessica drove to one of the several uniform shops in the city. The
clerk was nice and met them as they came through the door.
"Hi, my name is Sylvia, how may I be of assistance to you two ladies?"
"Hi Sylvia, my name is Jessica and this is Chelsea, Chelsea is going
to be my maid and I need to purchase her some proper maid's uniforms
and accessories."
"Oh, how nice. Have you been a maid long," asked Sylvia of Chelsea.
Jessica stepped in. "No actually she is quite new at it but she is an
amazingly good maid. Certainly not your run of the mill domestic
servant that's for sure."
"Well that is good. There are a lot of maids but honestly very few
take the true pride in being a maid that they should. It's difficult
to find a girl who will be a really great maid like Chelsea must be
for you to praise her like that."
"Yes, exactly but that's not the case with Chelsea."
"I know you told me what a great maid she is."
"Oh no not the great part, the girl part. You see Chelsea is a sissy."
Chelsea felt faint, his legs went weak and he thought he was going to
hyperventilate. Oh, why did Ms. Jessica have to expose him to this
woman?
"I don't understand what do you mean she is a sissy?"
"Simple, she is a he who dresses and acts like a girl because he was
not created to be a man therefore she is a sissy."
Sylvia's eyes got big. "no can't be, look how perfect she is. How
pretty and delicate she is, her makeup is exquisite. How could she be
a he?"
The clerk was incredulous! "I, I, I just don't believe you, this is
some kind of a joke, right? Who got you to pull this on me?"
"No Sylvia I am totally serios. Chelsea here is a sissy boy, a pansy,
a pantie waist if you must."
"I just can't hardly believe it. You're really serious?"
"Yes really."
"Well why would she, I mean he, I mean She, I mean, I mean I don't
know what I mean...want to be a maid?"
"Because Chelsea is the best darn maid there is. She loves to please,
is obedient and respectful. She is perfect. She would never steel or
destroy, never take. She loves to clean and do all domestic work as
long as there is some praise in doing it. She likes to feel wanted and
needed."
"Wow she does sound perfect!"
Chelsea was now getting where this was going.
"She is a perfect sissy maid and I am prouder of her than you can ever
imagine so let's get her the best uniforms you have."
The woman looked at Chelsea with a surprised but approving look and
nodded her head in agreement. Chelsea realized that Jessica was
exposing her to the clerk because of her pride and that she was not
embarrassed by the fact that Chelsea was a sissy. It suddenly made her
fell proud and good as well.
"Lets get to it!"
The clerk seemed to have some extra bounce in her step as she led the
two to the maid's uniforms department.
"We have many styles and colors for you to choose from. Most of our
customers are motels and hotels and we provide their housekeeping
uniforms to their maids."
"Ahh," said Jessica, you have some high-quality goods here."
"We stock a variety of price points, but for a very pretty and special
talented maid like Miss Chelsea here I would recommend only our best
uniforms."
"I agree," replied Jessica making Chelsea feel special.
They looked through the uniforms and Jessica asked Chelsea what she
would like.
"Oh, Ms. Jessica, no one has ever asked me to choose like this
before."
"That's all in the past now Chelsea, now that you are my maid I will
expect you to participate in your choosing of clothing as well as your
continued feminization. Now, which ones do you think are suitable for
your maid duties?"
"Well, Ms. Reynolds taught me about the duties and titles of various
maids but she said that in her home there was really only a need for
one maid and thus it was more important to have uniform changes to
better reflect my position at any particular time."
The two women listed intently and some what amazed at the sissy girl's
discussion of maids, duties, titles and uniforms learning a few things
for themselves.
Sylvia looked at Jessica wide eyed and said, "She truly is amazing!"
Jessica nodded her head in agreement as they both looked back to
Chelsea who had not missed a beat seemingly ignoring what the two
ladies were saying.
"I should think these uniforms with the pin stripes, this grey one and
this green one should do for early in the day dirty work such as
scrubbing floors and dusting and vacuuming. And these unstriped
uniforms in pink and yellow for afternoon work such as laundry and
cooking. And yes, these two styles of aprons, the plain trimmed white
one in the larger size to go with the morning uniform and the smaller
lace trimmed apron to accent the afternoon uniforms. And I...don't se
any. Ms. do you have any formal French Maid's uniforms that would do
for serving at a luncheon or dinner party?"
"Ah...no, no we don't carry that style of uniform, won't one of these
others do," she asked almost cautiously.
"Oh no, never. Ms. Jessica must be properly represented at all times
it's my duty and purpose in life to impress her guests. Now I ask you,
would you be impressed by a maid serving in one of these" and Chelsea
held up the uniforms?
Sylvia looked toward Jessica who had a look of, "well answer the
question it's directed at you and not me thankfully."
"Well no I guess not."
"Most certainly not but what if the maid serving you was wearing 6"
spike heels and a full formal French Maid's uniform with a very full
petticoat underneath and a silly little lace apron that served only as
a decoration and would do nothing to protect the pretty black dress?
Would you then take notice?"
"Yes, most certainly, I see your point. We just don't stock anything
like that and I am not sure where we would even order it."
Sylvia excused her self to see if anyone else in the store had any
ideas. She returned after about five minutes. "Karen suggested you try
a costume shop for a Fancy French Maid's uniform or even an adult toy
store. There is a big one out on Highway 87 at the junction or I can
give you the names of two costume shops here in town."
Jessica accepted the offer and Sylvia wrote the addresses and names
down. The checking out went quickly and the two were now in the car
deciding where to go next.
"The Custom Costume Collection is not far from here lets go there
first," suggested Jessica.
They drove the short distance and entered. An older blond lady greeted
them.
"We are looking for a high-quality Fancy French Maid's uniform, would
you possibly have such thing?"
"Is this for play or for serving in," The lady asked?
"Serving in, at formal get togethers, I am looking for something of
high quality."
"Which one of you is it for?"
Chelsea held up her hand and at the same time Jessica pointed to her
and said, "Her."
The lady looked Chelsea up and down and turned her around. "Ok come
with me I think I have what you want."
They worked their way through isle after isle of costumes. Very tight
rows and it looked like there must be at least a million costumes in
this shop!
Finally, they got to where the lady wanted them and she perused the
rack and took out a uniform and held it up to Chelsea. "Yes, I think
this will do, if not, we are close. Are you shy?"
"Shy, Ma'am?" replied Chelsea.
"Do you mind changing here or must you have a dressing room, they are
on the other side of the store if you want one?"
Chelsea looked to Jessica for help.
"Oh, I think Chelsea will be just fine changing right here. Get your
blouse and skirt off Chelsea and let this lady try the uniform on
you."
Chelsea was a bit nervous but since Jessica had commanded it she was
good to go and did as told. In all it was sort of exciting for Chelsea
because she was looking at the huge square-dancing petticoat that went
with the dress and somewhat hypnotized by it thinking how it would
feel and look. When the blouse came off it was pretty obvious to the
lady that Chelsea's bra cups were filled with falsies and she was not
dealing with a real girl. The lady looked at Jessica and smiled.
Jessica smiled back helping her worried look to evaporate.
"No worries dear, I put more French Maids uniforms on crossdressers
than I do real women. It seems to be a favorite of theirs."
Chelsea heard what the lady said but pretty well ignored it. The
uniform was the right size and soon Chelsea was decked out in a fancy
formal French Maid's uniform and loving every second of it. Oh, how
she loved the feel of the soft petticoat against her nylon covered
thighs and they way it swished and swayed when she walked. The other
uniforms acted nothing like this one. It was so, so, so wonderful!
"Oh Ms. Jessica, I love it, I love it. Can I have it? Pretty please,
pretty please?" Chelsea was ecstatic over the uniform. It was quite
apparent to both ladies that she would rather have this than a ton of
gold! Chelsea's enjoyment and emotional display was fun to watch and
the two ladies allowed her to walk and dance and twist and turn to
heart's desire.
"I don't know if you are interested Ms. But I have a few special
accessories that can go with it if you want them."
"Special accessories? Like what?"
It was hard for Jessica to imagine what the lady meant. After all the
uniform consisted of a dress, petticoat, apron, gloves, cap and
collar.
"Come with me we can let the little princess enjoy looking at
herself."
Jessica told Chelsea she would be back in a few minutes. She followed
the lady to another section and into a back room.
"Here!"
The lady showed Jessica the collection of items. It was quite the
Bondage collection. Locking collars, locking heels, arm binders, gags,
face dildos, spreaders, very restrictive corsets, butt plugs, even
strap on dildos.
"Some of the clientele that buys or rents certain uniforms want
accessories to go with the uniforms. Now these are only for sale not
for rent as I am sure you can understand why."
"Oh yes I can imagine. My friend who is much more experienced than I
am suggested I use a strap on, on her, what do you recommend?"
"Well, to be quite frank I have this one here. My husband has been
turned into my own personal sissy maid so I can speak with experience.
I like this one because it fits up in me and gives me a lot more
personal pleasure than the others do. Its quite realistic and
therefore permits you to feel like a man taking her which will give
you a feeling of power. Now everyone wants the 8" or even the 10" but
trust me, it's much better to start out with the 6" and work your way
up until he gets used to it.."
"Really? Your husband is a sissy maid?"
"Yes, among other things. It's a long story perhaps some other time. I
would also recommend an arm binder to secure his arms behind him so he
can not interfere and a gag preferably a penis gag if she were mine to
keep her quiet and make her feel even more helpless."
"Is their feeling helpless important?"
"Oh, my yes dear, very important indeed. They need to surrender and
that can be hard for a male to do but if they have no choice then
their ego has no say and yes its much, much better to make them feel
and be totally helpless."
"I see, that makes sense. Well Ok I am on a budget here so for now I
will take the uniform and the 6" strap on and the penis gag and the
arm binder. We can add more to it later."
"Sounds good I'll ring you up."
"Oh, and can you put the extra items in a bag so Chelsea does not see
them? I want to surprise her later."
""Sure, no problem."
Jessica went to find Chelsea seeing her way across the store standing
in front of a three-way mirror just ogling herself, flipping her skirt
and petticoat up, bending, prancing and even practicing a few
curtsies.
"Are you ready to go Chelsea, it's time to change."
"Oh Ms. Jessica could I please wear it home? Please, I just love it.
It's so wonderful Please could I please?"
"Chelsea, you know everyone will stare at you if you wear that out on
the street!"
"So...I don't care they will just see how pretty it is. Please, could
I please?"
"Oh, you are a piece of work Chelsea! I don't know why I should but ok
this one time."
Chelsea was jumping up and down just like an excited little girl
would. Jessica laughed to herself at how silly Chelsea was acting over
a dress! "Ok gather up your skirt and blouse and lets go."
Jessica told the lady that Chelsea wanted to wear it home, she smiled
and handed Jessica the bag of extras that either Chelsea did not
notice or did not care about as she did not acknowledge it at all.
On the way home Jessica could see Chelsea wiggling around and asked
her what was going on with all the wiggling?
"Oh nothing Ms. Jessica I was just rubbing the petticoat against my
bare upper thighs above my nylons. It feels so cool, you should try
it."
"No Chelsea I am not the sissy maid you are and you will remember your
place. I have been a little too lenient with you, young lady but you
better watch your step or you will get a severe over the knee
paddling! And I mean it, don't test me or you shall be one sorry
little girl!"
Chelsea had this horrified look on her face. "Oh Ms. Jessica I am
sorry I don't mean to be bad or disobedient, I am so, so sorry."
Jessica could see the remorse on Chelsea's face so she lightened up.
"It's ok's this time but don't forget who the boss is!"
"No Ma'am, I won't."
Jessica smiled at Chelsea as she proceeded to the shoe store. "We need
to get you matching shoes for your uniforms."
"Really? I get more nice things?"
"Yes, but know that I expect you to take good care of your things. I
want you looking sharp at all times when in my service Chelsea. I
won't tolerate sloppiness at all. I have high expectations for you and
you must remember that you are a reflection of me just as you are of
Ms. Reynolds. Chelsea, I hope you understand what an important and
privileged position you have with both of us. A lady does not lightly
trust her privacy or innermost secrets to just anyone. You are a very
special girl in many ways but I hope you fully appreciate the gravity
of your new position."
"Wow! I never knew, I mean I didn't realize how lucky I am to be a
sissy maid for you and MS. Reynolds. Oh, I will perform my duties to
the utmost of my abilities. Thank you for explaining this to me. It's
a lot more important than I realized."
"How do you feel now that you know?"
"I feel very special Ms. Jessica, it makes me very proud to be your
sissy maid and that of Ms. Reynolds. I feel very lucky and privileged
and I want to thank you for the opportunity."
"Your very welcome Chelsea."
They had arrived at the shoe store. Jessica suggested that they look
at lady's tennis shoes for the early morning uniforms and then at 4"
heels for the afternoon uniforms and of course 5" or 6" heels for the
formal uniform.
As they perused the shoes Jessica watched Chelsea to see if her
appreciation of shoes was as equally as high as her own. Chelsea
seemed to really get into the shoes so this put a smile on Jessica's
face. Fortunately for Chelsea her feet were as small as the rest of
her and finding her size in a lady's shoe was quite easy. Soon they
had 6 pairs picked out. One for each of the working uniforms and a
pair of 5" strappy heels and a second pair in 6" for the formal
uniform. Jessica was not to sure that Chelsea would be able to
navigate or last a long time in the 6" heels so she felt a second
slightly lower pair was a wise decision.
Chelsea, on the other hand, most likely would have settled for a pair
of 10" heels if she could have found such a thing! She was not at all
tuned into the practical at this point.
Each pair was tried on and Chelsea walked in them, turned in them even
curtsied in them! She was enjoying the shopping and freedom to help
choose what she was to wear. This was in sharp contrast to the way her
mother and sister did it. They picked out not caring what she wanted
at all. Of course, at that time. Chelsea was wearing feminine items
only because she was forced to wear them under the constant petticoat
punishment that had been laid on her. Things were different now. She
WANTED to dress like a girl, she WANTED these items and looked forward
to how they felt and looked on her.
Jessica enjoyed seeing Chelsea so enthusiastic toward her new things
and her new position as a lady's maid. It made her feel good to see
Chelsea so excited but it also turned her on. There was something that
stirred Jessica about having a sissy maid. It was like owning her in
some ways. She had the power and control to make Chelsea do what ever
she wanted but it was not the raw power that turned her on so much. It
was that Chelsea wanted to please her and would do most anything to
please her. No forcing, no pressure, no anything other than to say
she wanted it and Chelsea would simply curtsey and obey. It was
intoxicating.
They checked out and the shoes further depleted Jessica's meager bank
account but she had no remorse. She saw this as an investment into
Chelsea and for herself. She was already looking down the road to a
time when Chelsea might live with her full time.
As they walked to the car, Jessica looked over at Chelsea and saw a
person who was truly happy and enjoying life. It made her happy and
proud to be part of that. Being a sissy maid and giving up on ever
being a real man was definitely the way for Chelsea to go. And at
least for now it seemed that she understood and embraced that.
"Let's go home Chelsea and get you into a pretty new maid's uniform.
Then we are going to fix up a room just for you to keep your things
and then my prissy little sissy maid, you will be fixing me lunch!
Then after lunch I have a surprise for you."
"You do Ms. Jessica? What is it?"
"Now it would not be a surprise if I told you...would it?"
Bree
- 04.06.2022
- 32
- 0
