Chelsea and Jessica go Uniform Shopping
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Chelsea Begins Training For Marriage free porn video
Chelsea begins training for marriage
By
Sissie Maid cuckold
"Sylvia...this is Jessica..."
"Yes dear, how are things going?"
"Well...that's what I am calling you about. Some things have happened
and I am not really sure how to handle them and I need your advice."
"Oh...tell me about what's going on, nothing bad I hope?"
"No nothing bad...well at least I don't think so. Well anyway Chelsea
has told me he loves me and I can tell he is truly in love with me."
"Does that scare you?"
"No but it concerns me. Sylvia I really love him too and I guess since
things are...well...not really normal in this relationship to say the
least, I mean what do I do? How do I handle it?"
"Oh, I see, that. Well first congratulations on your new mutual love. I
think it's wonderful and I was wondering how long it would takt the two
of you to figure it out..."
"You mean you knew all along?"
"Why yes dear it was so obvious only a blind/death person in a coma
would have missed it. Why do you think I asked for your help that first
night I sent Chelsea home in her uniform?"
"But how? I mean we had not even ever met at that point?"
"Chelsea of course. He loved to talk about you and always did so with
such respect and admiration."
"Ok I can see how you knew how he felt but how about me?"
"Listen sissies are usually quite intuitive and sensitive. I knew if he
felt like that about you that you must be sending him some signals as
well about feeling the same about him."
Jessica laughed. "Well I certainly came to the right person to ask for
help now, then didn't I?"
"Maybe you did. I am glad to help. So, what is it that truly concerns
you?"
"A lot I guess. First, I am out of my element, I mean I don't have to
many friends who have a sissy for a boyfriend. And I don't want to
screw it up like hurt him in any way. I really do love the pansy and I
would like to make this work. But as I am sure you know having been
married to a sissy husband yourself, there are some things that have to
be worked out. Its like a real Female Led Marriage not one like most
where the women drive from the back seat in the marriage letting the
man think he is in charge. This is in your face up front kind of stuff.
I mean how do I start and where do I go?"
"You are right Jessica this is new ground for you but it's also
exciting ground. You will get to create the relationship the way you
want it and he will go along and be happy. His submission will permit
you to do almost anything and have it be accepted by him. The important
thing is to understand he is expecting leadership from you. He does not
want to be part of the decision making and in fact to involve him in
such will put strain and stress on him. In some ways this makes it
easier but it also puts a great deal of responsibility on you. So, to
start with you need to look down the road and plan what you want your
marriage to look like."
"I'm not sure what you mean by what my marriage looks like. I mean yes
I understand and want to be in charge and make the decisions and I am
completely fine with that but what other things must I plan for?"
"Ok good. Well, are you going to keep him as a feminized sissy maid
forever?"
"Yes, why wouldn't I that is what he loves and what he is good for?"
"I agree Jessica, I am only asking you things that I think you need to
work out in your mind before you move forward. These are not challenge
questions just questions to determine your plan and if you have thought
it out."
"Ok."
"So, will he wear only feminine apparel from now on or will he be
allowed to dress partially as a man for certain things like doctors'
appointments? The wedding, around his family or friends?"
"I want him in dresses for ever. No male clothes at all not now not
ever. I see no reason for it."
"Ok, what about duties. Like housework, cooking, laundry and other
menial tasks?"
"I would certainly expect him to do all those things. After all, as a
sissy that is his duty and as a male in my presence that is his
recompence. Don't you agree?"
"Absolutely I agree. What about sex? How will you handle his and
yours?"
"Well I already explained to him that a girl needs a real man from time
to time to satisfy certain needs and he says he understands."
"But does he? Does he really understand what that means? Its easy for
him to say one thing but when the time comes he may act entirely
different. You will need to educate, train and prepare him for what
will come. Have you thought about how many lovers you want? How often?
What freedoms they will have? How he is to treat them? Serve them? What
you will permit your lovers to do or say to him?"
"No, none of that. I guess I had not thought that part though at all.
Can you help me figure that out?"
"Yes, dear I most certainly can. Let's start with your libido. What are
your sexual requirements?"
"Oh, wow that's pretty frank, I guess it's the only way you can get the
answers though."
"Don't be embarrassed we all have our needs. I have a pretty high
libido my self and so you know I always tried to keep 3 regular lovers
and have another two I was trying out at the time. I find that after a
while they lose their energy, appeal or enthusiasm and a new lover is
always a welcome adventure."
(Authors note: My late wife, Madam Rebecca said this exact same thing
to women she counseled on cuckolding and she practiced it religiously,
she always kept a minimum of three regular lovers while experimenting
with others).
"Really, that many?"
"Its not so many if you enjoy and want a lot of good sex. Trust me it
takes a lot of good men to really keep a woman sexually satisfied all
the time."
"Wow, I will have to work on that I have never had more than one
boyfriend at a time before. I take it you enjoyed them many times a
week?"
"Yes, I most certainly did and my husband had to deal with all those
visits. You see it's not done separately or behind his back you must
involve him in it."
"What do you mean involve him?"
"Well ok most of the time your lovers will come to your home. Either to
pick you up for a date and then drop you off or to stay with you.
Chelsea needs to act as your secretary, maid and confidant in these
cases. She will answer the phone from them and take messages perhaps
even make calls to them for you. She will greet them at the door, seat
them and serve refreshments if you are not yet available. She will help
you get ready, bathe you, pick out proper wear. She will turn down your
bed, serve the two of you refreshments in bed if asked. Clean up after
wards. Things like that."
"You make it sound heavenly."
"Well it is or can be if you do it right."
"You mentioned something about my lovers and their freedoms and how
they would treat Chelsea, what do you mean by that?"
"Men that cuckold husbands often like power and to be in charge. Now
having Chelsea feminized and subservient will go a long way in
satisfying this need but many will want to make sure you and she both
knows who is charge."
"Like how?"
"Like calling her names that put her down, ordering her to serve them,
spanking them, making them beg to have you sexed, things like that."
Jessica was getting really wet and excited listening to Sylvia talk
about this subject. As Ms. Reynolds said these things Jessica was
imagining a lover doing them to Chelsea and she found it quiet erotic.
"Really, other men will do those things to Chelsea, like right in front
of me or if I am not there?"
"Right in front of you dear. They want to impress you that they are not
pansies like Chelsea and of course in turn they send a message to
Chelsea not to cross them."
"When you say spank her what do you mean, how would they do that?"
"Well presumably you will choose manly men as your lovers. And if they
are anything like my lovers they would grab my pansy husband by the arm
jerk him over their laps twist his arm behind his back, brush up his
skirts and paddle his behind until he cried real tears. Then they would
either make him kneel in front of them and apologize for being a pansy
and then suck their cocks or send him to the corner!"
"ARE YOU SERIOUS?"
"Yes, most certainly, I have seen them do it many times."
"Sylvia that is so fucking hot. What did you do?"
"I found it hot as well and I must admit it really turned me on and as
a result we enjoyed fantastic hot sex when they were done punishing my
wimp husband!"
"Oh, wow Sylvia, I love it I am so turned on right now you can't
believe it!"
"I know Jessica, I know I am too just remembering them doing it."
"I'm sorry I didn't think, how rude of me to remind you of such things
now."
"Not at all dear I love remembering the good things, there is really
nothing better than having a total pantie waist sissy husband, there
really isn't."
"I may be out of line, if so tell me. But if you want after I have a
lover maybe you and your lover could come over and we could have them
punish Chelsea and when they are done we could retreat to separate
bedrooms and enjoy the results!"
"I love the idea Jessica, please yes lets do that. It would mean a lot
to me."
"Ok it's a deal. My imagination is working over time!"
"Jessica, your imagination cannot begin to compare to the reality of a
real man dominating a sissy and putting her in her place in front of
you. You are in for a real treat."
"So, what do I do now?"
"The best thing is for you to begin to train and prepare Chelsea to
accept that you will have real men around."
"How do I do that?"
"By showing him why you need real men, what real men can do for you and
why he can't do it. Then you must show him that what he does for you
real men cant or wont do either so it gives him purpose and something
to take pride in."
"I see..."
"Why don't you bring him over tomorrow and we can begin this together
and once you get the idea then you can continue on your own."
"Oh, I would love that, thank you Sylvia. How about 9:00 AM?"
"Sure, that's perfect, see you tomorrow."
"Bye."
Jessica informed Chelsea that they had an important appointment the
next day at 9:00 AM with Ms. Reynolds. Chelsea was excited and anxious
to be there. After all these were his two most favorite women and now
he was going to be able to be with both of them at the same time!
Upon arrival Chelsea properly and daintily curtsied to Ms. Reynolds.
"Well that's just perfect Chelsea you are really becoming a very fine
pantie waist."
"Thank you, Ma'am," followed by another curtsey.
"Wont you both come in...Chelsea you can take your place on the floor
in front of us, this includes you as well."
Sylvia and Jessica sat in chairs and Chelsea sat on the floor in front
of them with her legs together and out to the side as a young lady
should sit very interested in what was going on.
Sylvia smiled and began, "Chelsea, Jessica tells me you told her you
loved her."
Chelsea quickly looked at Ms. Jessica and saw her smiling and nodding
her head.
"Yes Ma'am, I love her with all of my heart. She and you have been so
kind to me and gave me purpose. I hope its ok? I'm not in trouble for
telling her that, am I Ma'am?"
"No, no Chelsea, your not in any trouble at all. It's wonderful that
you shared those feeling with Ms. Jessica. And I am sure you know that
she loves you as well."
Chelsea smiled and turned red. "yes she does, she told me she loved me
too and it made me so happy I started to cry..."
"Then you realize how lucky you are to have Ms. Jessica, aren't you?"
"Oh yes Ma'am, very much so."
"Ms. Jessica can vouch what I am about to tell you but Chelsea I knew
the two of you loved each other the first time I met you so I am very
happy to hear that you both have shared these wonderful words. But now
we come to the practical side of things."
"The practical side of things Ms. Reynolds," asked Chelsea with a very
worried look on her face.
"Yes Chelsea, the practical side. Its no secret to any of us that you
are...well...less than manly. In fact, you are a pantie waist sissy and
while there are very good and practical uses for a wimpy male like you
there are roles that you cannot fill in a woman's life. That being what
a real man can do for a woman. So, while you and Ms. Jessica will be
getting married soon..."
"Married! Really! Is that true Ms. Jessica?"
Jessica smiled a huge smile and confirmed that what Sylvia was telling
the little pansy was true. Chelsea could not have been happier.
"If I may continue...there are certain things you must accept and train
for if your marriage is to be a happy and successful one."
"But couldn't I try to please her as a man just to see if I could?"
Sylvia frowned and looked at Jessica who also frowned.
"Chelsea there is no chance of you being able to do that, not one in a
trillion, stand up and come here."
Chelsea did as instructed and stood in front of the two ladies.
"Pull down your panties and lift up your skirt and let your little
willie come out."
Chelsea reached under her skirt and lowered her pink lacey panties to
her ankles. They were so cute and juvenile looking both ladies smiled
upon seeing them. Chelsea then lifted the hems of her flowered white
skirt and spread her legs. Out popped her little dickette. It suddenly
began to grow as the ladies watched. It got to sticking straight out
and was obviously rock hard.
Sylvia put her hand over her mouth to stifle a laugh, Jessica did the
same thing. It was soooo tiny and cute! Their eyes went back and forth
between his tiny dickette and his face. Chelsea could see their
amusement and it made his face turn bright red. Sylvia placed her
middle finger next to his willy while Chelsea lifted her skirt as far
back as she could and bent her head forward to look down at what Ms.
Reynolds was doing.
Sylvia laughed. "look Jessica, it's not even as long as my finger and
about the same diameter. If he could ever get that pathetic thing in me
I would have to ask him if it was in to know!" And she and Jessica both
laughed.
"Hang on a minute I want to get something, I will be right back."
Sylvia left the room only to return with a picture frame and a screw
driver. She handed the screw driver to Chelsea and asked her to go the
door hinge and take out a screw. The screw driver was tiny and designed
for the size screws in eye glasses and it would not be of any help
removing a door hinge screw. It was simply to small, totally
inadequate. Chelsea was confused and told Ms. Reynolds the screw driver
was way to small for the job.
Then Sylvia showed the picture she had brought out to Jessica who's
mouth flew open. Next, Sylvia showed it to Chelsea. The picture was of
her with one of her lovers. A man with a 10" thick cock. Ms. Reynolds
had her arm bent and beside it so her elbow was near his balls and the
cock was as big around as her arm and went to her wrist. Her point was
obvious. Chelsea's mouth dropped open and she kept looking back and
forth between her little dicky and the one in the photo and understood
what Ms. Reynolds was trying to convey.
"You see Chelsea just like wit the screw driver you don't have the
right tool to get the job done. Do you understand this?"
"I guess," said Chelsea with her head hanging.
"Listen honey," said Jessica. "I have other things in mind for you. I
love you and I still love you even though you don't have a man's dick.
But you must understand that just because you don't have a real man's
dick it does not mean I can go without one. A woman has needs. So, if
we are to get married it must be with the understanding that I will
need to enjoy sex with other men and you will need to accept that."
"Chelsea, my husband was a small dicked sissy just like you and we had
a very happy marriage because he not only accepted that I needed lovers
but he embraced it."
"How did he embrace it Ms. Reynolds?"
"He did so by giving his full support to me. He encouraged me and even
helped me to have other lovers. When they came by he served them as our
maid and addressed them with the proper respect a man deserves."
"He did? He really did all of that?"
"Yes, he most certainly did. Wait here I will go and get a scrap book
and show you some of the things he did that made me so very proud of
him."
Jessica was anxious as she was not sure how Chelsea was taking this.
Chelsea was beside himself trying to understand and adjust to what he
was being told.
While Ms. Reynolds was out of the room Jessica said to Chelsea, "I am
proud of you sweetie and you look so good in that pretty dress and
heels. It's all going to work out because we want it to work out. Ms.
Reynolds will help us and she only has our best interest at heart."
"I know Ms. Jessica, it's just...well it's just that I don't want to
ever disappoint you."
"Oh silly, you are not going to disappoint me. If you do something
wrong I will punish you for it and then it will be forgotten!"
Chelsea's face went rom a frown to a smile. "Honest Ms. Jessica?"
"I said, so didn't I?"
"Yes, yes you did Ms. Jessica, thank you, I love you."
"I love you too."
"I found what I was looking for. Now here in this picture you see my
sissy maid husband serving us refreshments."
Jessica smiled. "Oh, that's so cute Sylvia, look how his frilly panties
show as he bends to serve you and your friend and you made him wear 6"
heels, that's wonderful."
Chelsea was looking on wide eyed as he had never seen another boy
dressed like a sissy maid serving.
"Are those little locks on her shoes?"
"Yes, yes, they are, good catch Chelsea. Danny, my lover in this photo,
insisted that I keep her locked in her uniform. Her shoes were locked
on and there was a lock at her collar and her waist. See if you look
really close you can see them."
"Yes, I see them..."
"And in this next photo, you can see my little pantie waist polishing
my lovers, this time it's a man named Jason, but see he's kneeling
beside the bed polishing his shoes. And over here see this, this is a
hand written note my husband gave to Greg another one of my lovers
thanking him for pleasing me sexually since he, my husband was so
inadequate that he could not."
Jessica interrupted, "So you had your husband interact with your lovers
in different ways. Maybe you can explain to us why you did that and if
it is important."
"Sure, be glad to. Yes, its very important for both your lover and your
pantie waist sissy to interact. It can be uncomfortable for a sissy to
have real men coming and going and being with his wife. If he is left
out he can become with drawn and not feel part of things and that can
lead to depression. The lover can feel awkward having the sissy husband
at home but with no control or input into him or what he does.
So, the solution is for the boyfriend to know he has control not only
of the wife but the cuckold husband as well. Since Chelsea is already
feminized the lover cant be intimidated by him because as all men know.
No real man would dress like Chelsea does.
Your lovers will want to win you, impress you that they can do the job
and, in that process, they need to have some control over Chelsea. So,
like this photo my lover decided that my sissy maid should be locked in
her uniform. She liked it also, she said it made her feel even weaker
and more defeated and controlled. Chelsea will learn to like what your
lovers do to her as well."
"Ms. Jessica, do you like the idea of your, your boyfriends controlling
me?"
Jessica looked at him and said, "yes, yes I do Chelsea, I think it will
add a needed dynamic to our relationship. It wont be just me ordering
you around my lovers will be ordering you around too. I like the idea
that you will be subservient to my lovers as well as me. I think that
shows respect on your part and power on mine.
In fact, Ms. Reynolds told me about how her boyfriends would spank her
husband to put him in his place and I find that extremely erotic and
exciting."
"Would you have them just spank me even if I was not bad or had done
anything wrong?"
"Yes, Chelsea I would because its not about right or wrong its about
power, sex and stimulation and seeing you put over a real man's lap and
paddled is a huge turn on for me."
Chelsea's hands involuntarily went to his bum and felt it as if he had
been spanked and his eye brows raised way up as he considered what she
said.
"But what about me, don't I get any say at all?"
Ms. Sylvia got stern. "Young lady, you have NO say in anything! You are
a pansy, a wimp. You are not qualified to be a man so you have been
allowed to become a pantie waist sissy wimp. Your job, no your purpose
in life... your only purpose in life, is to please and serve your wife.
If Ms. Jessica is kind enough to provide that opportunity for you I
think you had better understand that your life is about her, not about
you!"
"I am sorry, so sorry Ms. Reynolds I was just wondering but I
understand."
"Jessica, I think you should borrow my scrap book and you and Chelsea
look though it. And wait...here are a collection of articles on
cuckolding that both of you should read. In fact, it may be good for
Chelsea to read them out loud to both of you."
"Thank you, Sylvia, we will do just that and I am sure we will learn a
lot and it will help us immensely. Chelsea pull up your panties now my
dear and don't forget to tuck that nasty little dickette back where it
goes, I don't like seeing it, its disgusting and will only serve to
frustrate me."
"Yes Ma'am, right away Ma'am."
Chelsea did as told though it hurt like heck to bend his little stiffy
back. He managed to get it tucked and ladies watched as he wiggled into
his panties that had been around his ankles. Chelsea provided the
proper curtsy and the two left for Jessica's.
When they got back to Jessica's she said, "I am going to call your
mother and let her know you are staying with me tonight."
"I am?"
"Yes, we have to study the material Ms. Reynolds shared with us and I
am horny and need sex."
Chelsea was not sure what she had in mind so he asked, "are you going
to invite another man over tonight to have sex with?"
"No, not tonight. You are not quite ready for that yet."
"Oh."
Jessica got out her strap on and laid the materials Sylvia had given
them out on the bed and told Chelsea to get on her knees and start to
read the material out loud. Jessica took of his panties and lubed him
up and inserted her strap on into Chelsea's bottom amidst moans and
groans and a gasp or two.
Chelsea began, "Things I do to my cuckold."
"Oh, this should be very interesting," said Jessica. "Continue."
1. I make my sissy cuckold get me ready for my dates. He must choose
the right lingerie that my lover will like and he can only do this by
asking him. He will bath me, do my nails, help me get dressed knowing
that I am dressing to please my lover and see me off.
"Oh, I like this Chelsea, think how much fun that will be and then you
must wait till I get home to hear what all went on. Yes, I want to try
this one for sure. Don't you think that will be fun, especially the
part where you have to ask my love what kind and color of panties and
bra he prefers?"
Jessica's hard cock was deep in Chelsea's ass feeling very good. He
most certainly had mixed emotions especially about having to ask his
wife's boyfriend what color panties and bra he wanted her to wear just
the thought of it was quite humiliating but at the same time the dick
in his pussy ass was causing his brain to warp!
"Yes, yes it sounds like a good idea."
"Just a good idea?" and she slowed her rhythm.
"Ah a great idea a really really great idea."
"Good girl. Next."
2. When my lover comes over I make her curtsy and address him as Sir.
After she leads him to chair she must kneel and take off his shoes and
ask him if she may polish them for him.
"Oh, how humiliating that must be to be a sissy and have to polish your
wife's lover's shoes. I think that is character building and would be
good for you, don't you?"
Chelsea was really getting worked by from the pegging that his
girlfriend Jessica was giving him. He didn't care what he said as long
as it got Jessica to finish him off.
"Yes, I think it would build my character as well to polish your
lovers' shoes Ms. Jessica."
"Good girl go to three."
Jessica was getting close herself it was all too much for both of them.
All the stimulation at Ms. Reynolds and now this.
3. I like to make him beg my lover to make love to me and explain to my
lover why he is begging him to do so.
"I think this makes perfect sense otherwise the poor lover would not
know why he is there. Tell me how you will beg my lover Chelsea."
Chelsea did not really like this list but for what ever reason it made
her excited and even more so to hear Jessica telling her to like it or
what to do.
"Ah, Mr. lover, Sir. Would you please make love to my gorgeous wife? I
can not do it Sir. I am a limp dicked pantie waist and wear only
dresses and makeup all the time. I am not man enough to make her
satisfied Sir so would you please use your magnificent cock and please
her? Please Sir, I beg you."
"Oh, Chelsea that's perfect I love it that's what you will say to my
first lover. Go to four and hurry I am getting close."
4. I make my cucky fluff my lover. Working his cock head slowly at
first and then licking up and down his shaft to bring it to full
hardness. I love to see his sissy head bobbing up and down on my real
man's cock knowing it's making it rock hard for my pussy.
"Now I know I would love seeing your head going up and down on a real
man's cock, it would be amazing. Oh, wow I can't wait. Wont that be so
sexy to see your lipstick covered lips ridding up and down his hard
shaft knowing that in mere seconds it will be in my wet pussy bringing
me the kind of pleasure you will never be able to give me?"
Chelsea did not know what to think about this. He had no interest in
men or especially in sucking a cock. He liked girls. And Jessica was
rubbing it in by talking about the kind of pleasure her lover could
bring her and that he could never do it. It hurt but he also knew it
was true. He was not sur what to do so he said nothing.
"Chelsea if you want to cum you better start telling me how much you
want to be my fluffer and what you will do and why."
Chelsea was on the edged and as Jessica began to slow her pumping he
tried to wiggle his ass to get what he needed but she was wise to him
and moved directly with him so there was no stimulation.
"Tell me Chelsea, Tell me or else!"
"Ok, Ok I want to be your fluffer and get your lovers cock ready for
you. I, I, I (he was getting very close to cumming) I will lick and
suck his cock to make it hard and rigid for you Ms. Jessica. I. I
really...want...to...suck...his cock so you can...enjoy it." He was so
close but each time he slowed or hesitated Jessica slowed. Talking
about it was working him up even more so he dumped any and all of his
pride and said, "Oh Ms. Jessica I want so much to suck your lovers'
cock to let you see my pink lipstick covered lips going up and down his
shaft as he holds my head and fucks my mouth. I will do everything I
can to tease him to be rock hard so when he enters you, you have the
most amazing feeling possible from his rock-hard cock.
I...ahhh...I...ohhhhhh, ahhhhhhh!" and Chelsea started to cum from
having Jessica's strap on inside him. She came as well in a mind
shattering climax. She knew it was going to take a lng time to review
all of the material that Ms. Reynolds sent home with her but it would
be worth the time! She knew she was really going to enjoy training
Chelsea to be her cucky as well as other in other roles.
Clover
- 23.01.2022
- 23
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