The Fortunate Jeopardy Part 2
Tessa returned the greeting with, "Good evening Ma'am, I hope your day
was..." as he raised his head to see that there were two women in front of
him not one as he had expected and one of those was his former
secretary
Carolyn. "...ahhhh...
Tessa's face flushed then began to turn pink quickly going to red then
deep red. He looked and sounded like he was going to faint as he stood
their frozen in a half returned curtsey. For Tessa it seemed the end of
the world. His mind, heart and breathing was racing as if their speeds
would increase until his heart jumped from his brassiered chest and
danced across the floor and out the door!
Never in his wildest imagination had he ever contemplated even the
thought that he would be exposed to anyone other than his wife let alone
his former secretary! As his life flashed before his eyes his wife and
Carolyn stood their amused. Smiles covered both of their pretty faces as
neither could hide their glee at his total discomfort. Both women saw
this as some sort of retribution for his past deeds and were fully
enjoying the sissy's predicament to the max!
"What's the matter Tessa...cat got you tongue?" Laura asked laughingly.
"Ahhhhh, Ahhhhhh, Ahhhh," is all the little pansy could manage to say
still frozen with his mind short circuited.
"Aren't you going to say hello to Carolyn, you remember her, you used to
fuck her in your office. I think you will enjoy the fact that she now
has a little something on you panty boi. Give her a proper curtsy and
greet her like the sissy you are, you obviously are inferior to her now
aren't you Tessa?"
Tessa still unable to do anymore than grunt regained physical control
and turned slightly toward Carolyn and gave a perfect curtsy. As he
completed the curtsy he managed to say, "Good evening Ms. Cummings, I
hope your day was good." His predicament and training had overcome his
male emotions allowing himself to humiliate himself in front of a former
employee. His mind recognized it and this caused his heart and
breathing
rate to increase more while his color turned even redder.
"My, my Tessa, if you insist on keeping your cheeks such a deep shade of
red we can cut back on the blush you are using. So what do you think of
your former boss now Carolyn?"
Carolyn was standing their shaking her head holding her hand over her
mouth with a smile large enough to escape the coverage her hand was
trying to provide.
"I love it Laura, I just simply love it. What a pansy, I would have
never thought it of him as he used to pretend to be so macho. Your dress
is quite lovely Tessa and I love what you have done with your hair and
makeup."
"Stand up Tessa...lift your skirt and slip hems and show Ms. Carolyn your
panties...turn for her."
Tessa was totally beside himself and had no idea what to do or could see
any way out of his terrible predicament so he did as told. The two
women
giggled as he obeyed providing great entertainment to the ladies who
were enjoying Tessa's humiliation far more than he was. After a dozen
turns all of which were designed to further the little pansies
humiliation and nothing more Laura said, "Ms. Carolyn is going to stay
the weekend with us Tessa, her luggage is in the trunk of the car, fetch
it."
"Bu, bu, but, it, its daylight out there Ma'am."
"SO!"
Tessa raised his eyebrows and instantly reverted to a curtsy
acknowledging his orders and scurried past the two women and out the
front door like a cat being chased by a dog. The two women burst into
laughter as they watched him regain composure but only after reaching
the bottom of the front steps and moving toward the car. Laura said,
"watch this."
Carolyn not knowing what was up did as suggested. Tessa went to the rear
of the car and noticed the trunk was closed and locked so she went to
the driver's side opened the door and looked in bending over nearly
exposing her pretty pink panties as she looked for the key realizing the
keys were not in the car. Realizing Laura must have the keys she
returned to the house approached Ms. Laura curtsied and asked for the
keys. Ms. Laura handed them to the sissy and received a second curtsy
before she went back outside looking nervously to see if anyone else
could see her. The coast was clear so Tessa proceeded to the trunk
retrieving the suitcase and returning to the house.
Tessa was instructed to take suit case to the guest room and return.
Upon return Tessa executed a curtsy and stood before Ms. Laura awaiting
orders.
"Tessa, I don't suppose you brought the packages in that were in the
trunk did you?"
"No Ma'am."
"Well you need to get them; they are you new Maids uniforms and some
accessories. They were delivered to work today. They are your new formal
uniforms and you're going to need them this weekend since we will have
a
guest. You will need to dress appropriately for serving our guest; which
means wearing a more formal uniform."
Tessa now more relaxed and accepting his humiliation like the true panty
waist he was curtsied again and went back outside only to notice that
as
he did the next door neighbor Ms. Jenkins had just pulled in her
driveway. He felt exposed but was already in full view and could not
hide. He knew better than to run back into the house so continued on. As
Ms. Jenkins exited her car she yelled out, "Hello There," and waved.
Tessa turned slightly and nodded her head and instinctively tried to
give a feminine wave back. Tessa's heart was racing again and her
breathing was erratic. It seemed she might just faint as she was
becoming very light headed. Laura and Carolyn were inside watching and
giggling over the action.
There were six boxes in the trunk and Tessa tried hard to pile them all
up so as to carry them all in one trip but after much fussing could not
do it and resigned herself to one more trip exposed to everyone. This
seemed to be a turning point for Tessa. She finally resigned herself to
accepting her fate and not fighting it. She carried three of the
packages into the house and then returned or the other three.
Laura noted that Tessa's last trip to the car seemed relaxed and
pointed. "Tessa, your last trip to the car seemed more relaxed...was it?"
"Yes Ma'am, I realized that I should just do it like I should and not
fight it."
"VERY GOOD Tessa. I am proud of you that's a big step in your training.
Remember what you were told about your training and how I will know when
you are trained, well this is a huge step in that process, remember
it."
"Yes Ma'am, thank you Ma'am."
"Ok let's go into the living room and get these packages opened so you
can see the new things I have gotten you."
Laura and Carolyn took seats while Tessa sat on the floor with legs
tucked under her bottom and to the side, opening the boxes. And while
Tessa was a bit uncomfortable with Carolyn there, she was also excited
to see what was in the packages.
The first box held two large white petticoats; actually they were square
dancing petticoats but they would do nicely for a fancy French Maids
uniform holding the skirt out beautifully. It was soooo lacey. It was
not enough for Tessa to just open the boxes she was to fuss over each
item as a prissy girl would. Getting detailed instructions on how to act
from Ms. Laura and if not done correctly told to try again and again
until Ms. Laura was satisfied. Feeling the fabric and swishing it
around, looking at it closely and enjoying the gift. Tessa was made to
practice this over and over until Ms. Laura was satisfied he understood
how he was supposed to act.
The next box held two fancy French Maid's uniforms. Shinny Black and
white trim and short skirts. As Tessa looked them over she noticed that
there were locks at the waist and the collar. She wondered about and
looked over the locks for a few moments then innocently looked at Ms.
Laura and asked what they were for.
"Those are to help you feel more secure when wearing in the uniform so
you understand it controls you and you are its prisoner."
The prisoner term had a special effect on Tessa and her eyes flared
being reminded of her predicament. She went thought the examination
procedure as she had learned with the petticoats doing a perfect
feminine job at it.
The next box held two pairs of open toed strappy Black high heels one of
which was 4" and the other one 5". Both had locking straps on them
which
Tessa recognized and did not need to ask what they were for again.
The next box contained a corset and three body briefers. Tessa knew or
thought she knew what they were so did not ask. She did notice the body
briefers had extra padding in the hips and butt areas and it did not
take her long to understand why that was so. She also realized that
these things must have been made specifically for sissies like her and
that revelation added to the stories she had read made her realize this
was not an uncommon thing. The realization that other males must be in a
similar predicament both comforted and alarmed her.
When she opened the second last box she found it contained the
accessories. Aprons, caps, collars, gloves, garters, fish net nylons
even a leash which she found disconcerting. She noticed the one collar
said, "Sissy" on it and the other one said "Sissy Cuckold" on it. This
made her quiver as a chill ran her spine. The leash was something she
really wondered about but was afraid to ask.
When she opened the last box she found it contained toys. There were
butt plugs, a penis gag, two strap on dildos both Black in color and one
6" long and the other 8.5' long. She instantly thought Ms. Laura and
Carolyn were lovers and they were going to use these things, how wrong
he was! There was also a doubled ended strapon but one end was only
about 2" long and the other end was about 8" long, he didn't know what
that was about either but he would learn that the short end went in his
mouth and the long end would be used by his wife to pleasure herself.
There were four sets of padded cuffs and a ridding crop. He tried not to
look at the two women sitting there as he just did not know how to act
or what to think about the items in this box. His feeling was this was
not good for him but he hid that part well.
"Well Tessa, what do you think?"
"Ah it's all very Nice Ma'am, thank you Ma'am."
"It will all come to good use. All of these things will help you become
trained and I know how much you're looking forward to being completely
trained."
"He is? I am surprised, I didn't' think he would be so anxious to be
trained to be a sissy."
"Tell Ms. Carolyn why you are so anxious to be trained Tessa."
"Yes Ma'am, well Ma'am, once I am trained Ms. Laura is not going to put
makeup on me or nail polish on me anymore. And she won't pick out my
outfits and she is going to take me to a store and let me pick out
whatever clothes I want and buy them for me."
Laura looked at Carolyn and smiled a knowing smile which Carolyn picked
upon and said, "Oh now I understand well sure that makes sense so I can
see why you're so anxious to be trained now."
Tessa was very proud of himself now and beamed like a little girl. Later
Laura and Carolyn would discuss the training and Carolyn would
understand what exactly was going to happen and that Tessa was
misreading the situation entirely, Tessa was going to become a perfect
sissy maid cuckold and there was no way Laura was backing down on that
goal.
"Ok Tessa...let's get you changed into your new uniform and see how
pretty you are. Take your shoes and dress off."
Tessa's eyes looked back and forth between the two women hesitating.
"TESSA! What have I told you about hesitating, you just earned your
first punishment. You are NOT to be concerned if there are guests
present. You are a sissy maid you have no status, no rights, no station
at all in life, You are to think of any guest as your Mistress or your
Master...is that clear?"
"Yes Ma'am, sorry Ma'am." And Tessa quickly stripped of his working
maid's dress and his white slip along with his white ladies tennis
shoes, standing there now in a pair of pink lacey panties and a matching
pink bra."
Oh my Tessa, I love your pretty panties and bra, they seem so...so fitting
for a sissy like you," Carolyn replied, giggling as she did.
Tessa was quite embarrassed by this and tried to put his hands in front
of his panties and bra to no avail. Laura thought it was a nice feminine
gesture anyway.
First the body briefer was put on Tessa followed by the corset. The
ladies laced and tightened the corset until it was really squeezing
Tessa's waist line. Next came the fish net hose followed by the frilly
fluffy white petticoat. They all marveled at the transformation and then
they put on the maids dress on the hapless male. The dress was locked
into place and then the 4" heels were put on and locked. The "Sissy"
collar was put on and then the maids cap and apron.
Tessa looked marvelous and all of them even Tessa liked the look. Tessa
had already begun to relax and secretly enjoy the attentions and
presence of another woman even if he still found it quite humiliating.
Tessa, like all sissies, was quickly earning to love being humiliated as
well as feminized. After all there were no male items of clothing that
could hold a candle to even the plainest of feminine apparel but to
compare male attire to the finest, frilliest feminine attire, well it
just could not be done. Everything Tessa had on screamed submission,
captivity, subjugation and he could feel it through every bone in his
body and he was not finding it that unpleasant. However none of this was
occurring to him as his lacy prison was beginning to encapsulate him in
an inescapable cell.
"Very, pretty, very, very pretty Tessa I think we have found your
calling, don't you think so Carolyn?"
"Yes I do very much so, you do look pretty in your sissy maids uniform
Tessa and I have to admit I like you this way."
Tessa captivated in the moment was smiling and turned to the ladies and
curtsied to each of them thanking them as she did. This was truly a new
feeling for Tessa. As Tom he intimidated and caused people to fear him
and so they served and were around him due to those powers...no one or at
least very few of them, ever really liked him. But now he was being
liked and he liked that.
"Ok Tessa it's time to get your pretty little air head back in the game,
fix us some dinner and be quick about it...and don't stain that dress!"
Tessa sashayed off to the kitchen learning to navigate in the 4" heels
that were locked on his feet. Still enjoying the idea of wearing high
spike heels...well...he would learn the folly of that thought latter on but
for now it was fun and exciting.
The two girls talked...mostly about Tessa and what Laura had in store for
him. Dinner went well; Tessa did a good job of preparing the meal and
serving and took his proper place against the wall head bowed and hands
folded over his sissy apron. When it was time for Tessa to go to bed,
Laura sent him to change into his nightgown unlocking his dress but
leaving the heels locked on as they were. He was instructed to remove
only his dress, petticoat, and accessories and then return with his
nightgown on. When he returned Laura told him that since there was a
female guest in the house and one he had previously taken advantage of
and since he had a punishment coming she was going to do a few things to
him before he went to bed.
She told him to turn around and place his hands behind his back which he
did. She then cuffed his hands behind his back after which she ordered
him over her lap. Once there she spread his legs and unfastened the body
briefer claps between his legs and slid it up then pulling down his
panties. She had a butt plug all lubed up and pushed it in much to
Tessa's horror! It was not nearly as big as Tessa imagined it was but
since this was still virgin territory he did not yet know how to relax
those mussels and accept it. He would, he would learn this skill quite
well in due time.
Once the plug was in the panties were returned to position as was the
crotch clasps for the body briefer. Laura then put cloth bags over the
heels so they would not rip the sheets and then cuffed his ankles
together. Lastly came the Penis gag which caused Tessa?s eyes to flare
in fear as Ms. Laura moved it toward his mouth.
?Carolyn, would you like to attach the leash to his Sissy collar and put
him to bed??
?Yes, I would love to, thank you Laura.?
Carolyn got up and attached the leash to the Sissy collar and enjoyed
seeing Tessa turn bright red. She also enjoyed jerking his collar to
make him move faster since the pansy could only take 5? steps and in
high heels at that. When in bed she fastened the leash around the head
board tight enough to let him have a just a few inches of room. She
covered him up and whispered in his ear, ?I am so happy you have turned
into a fucking sissy cunt you bastard. I may see if your wife will allow
me to castrate you and put your balls in a jar on my desk at work?what
do you think about that my helpless little slave girl?? Then she laughed
a wicked laugh, turned out the light and shut the door.
Tessa lay their scared and helpless wondering if Laura would allow this
crazy woman to do this to him. He was scared to death and had a hard
time falling asleep but eventually did.
Carolyn told Laura what she had said to Tessa.
?You Didn?t! Wow that was perfect, let the little bastard experience
fear like we have when he had all the power and used it for his own
purposes only. That was great I didn?t know you had it in you to do that
to him.?
?To tell you the truth Laura I didn?t know I had it in me either but
seeing him so helpless gave me the courage, I hope he doesn?t sleep a
wink tonight worrying that I may return with a knife and a jar?you know
it might be kind of fun at that!?
They both had a good laugh over that as each of them imagined cutting of
his balls and his dick and seeing him run around crying about the loss.
Tessa went to sleep rather quickly considering the threat and the
situation he was sleeping under. The girls talked about furthering his
fears a bit and came up with a great plan. In the morning, Carolyn took
the extra two pair of cuffs into Tessa?s room and carefully secured his
left ankle; to the right side of the bed then un-cuffing his ankles
spread the right leg out as far as she could get it to go and fastened
it to the left side of the bed. She then moved his nightgown out of the
way and opened his crotch clasps on his body briefer and was pulling his
panties down when Tessa awoke. Tessa felt something going on and raised
her head partially only because her leash kept her from going any
further and she saw Carolyn at the bottom of the bed. Carolyn smiled at
Tessa and said, ?I thought about it all night Tessa and I really do
think it would be best if we cut of your little dickette and balls,
don?t you, I mean now that you are a real sissy and all, you don?t
really have any need for them anymore ,now do you?? Then she held up the
big knife so Tessa could see it. She smiled and told her she would be
quick about it then reached down and took hold of the head of his
dickette and pulled it taught. She lowered the knife putting the back of
the blade instead of the sharp part against his dick. His dickette had
been quite warm from being trapped between his legs for such a long time
and the cold edge of the knife felt amazingly sharp. She and Laura had
agreed for a special word to alert Laura to come in to the room.
?So Tessa, if you want me to stop just ask me to and I will but no
mumbling. I want to be sure you don?t want me to cut it and your balls
off so your panties will fit better.? Tessa was in a real panic now.
Laura was nowhere to be seen and this crazy woman had him bound,
helpless, and was surely going to cut his dickette and balls of and
enjoy doing it. He was crying and trying to beg her but the Black penis
gag filled his mouth and made it impossible for him to speak plainly.
Laura had been waiting just outside the door and heard the special code
word and so entered the room on key.
?Carolyn! What are you doing? I told you I was not ready to have him
castrated and dickless yet. I know the things he did to you and if
things don?t work out with his training I promise you I will let you go
through with it but not yet.?
?Oh please Laura, ok if not both could I just cut his dick off? Please
I?ll let him keep his balls or if you prefer I could just castrate him
and let him keep his dick, come on Laura he has no need of those useless
things anymore now that he is a sissy.?
?Carolyn I am sure you?re right but he has hopes of being a man again
after his training and if you cut them off now he has no hope left.?
?But you get retribution for what he did to you, what do I get? Its not
fair Laura I want something out of this from him as well.?
?What is it you want, what would make you feel like you?re getting paid
back.?
?He made me fuck him for almost two years. I might be satisfied if he
cleaned my house for two years?no that?s not good either make it four
years, yes four years he has to be my maid twice a week and do exactly
what I want and oh Ya I want to be able to peg him anytime I want that?s
fair isn?t it??
?It seems fair to me let?s ask him??
Laura moved to Tessa?s head and unlocked the penis gag.
?Oh thank you Ms. Laura thank you she was going to cut it off if you
hadn?t come in just when you did she would have cut it off I can feel
the sharp edge of the knife against my cock right now please make her
stop before she accidently slips.?
?Oh shut up Tessa. It really is not that big of a deal, you never
pleased anyone besides yourself with that worthless excuse of a dick you
have, I really don?t care much what she does. But there is an agreement
for you t consider. Your dick and balls in exchange for four years of
maid service, what?s your decision??
?But what about after I was trained? I was looking forward to being a
man again??
Laura laughed. ?Well what kind of a man will you be without your little
prick and balls Tessa? I mean it?s up to you if the delay is worth it or
not but I?m not going to try and take that knife from her, I know how
sharp it is I watched her sharpen it last night and I guess I should
have figured she was up to something but oh well, no skin off my back.
It?s up to you Tessa. But I wouldn?t wait very long she may get to
thinking about how you treated her and just do it.?
With that Carolyn pulled his cock real tight putting the fear of God
into Tessa. She screamed out, ?ok, Ok, Ok, don?t cut me I?ll be your
sissy maid for four years, I will, I will don?t cut me please Carolyn
I?m sorry I am really I am please I will be your sissy maid, I will I
promise.?
It was all Laura and Carolyn could do t contain themselves from laughter
at the idea of Tessa surrendering for fear Carolyn would cut his dick
and his balls off. But to be fair most guys have seen the gleam in a
woman eyes as she hints at enjoying doing just such an event and its
certainly not unknown that women have done it so it is very believable
to most men but especially to one who is bound, helpless and who has
preyed on the woman holding the knife.
Carolyn gave his dickette a real hard jerk causing Tessa?s eyes to flare
wide in surprise and fear. ?Let me tell you one thing Tessa, if you
don?t serve me twice a week as my sissy maid or if you don?t do a
perfect job or if you complain or if you are late OR if I ever see this
worthless prick exposed again I will cut it off, do you understand me
Tessa, I WILL cut it off! You better keep it tucked and you better act
like a perfect lady at all times.?
Scared to death and practically sobbing, Tessa?s face contorted with
fear. ?Yes Ms. Carolyn, I will, I will, I promise Ms Carolyn honest.?
Carolyn moved to release Tessa and Laura told him to get into his
working maids uniform and get them breakfast that they needed to get to
work. Tessa worked in a frenzy still grateful for being allowed to keep
his male equipment but not forgetting for a second how close he came to
loosing it?all of it.
The two women laughed hysterically all the way to work a they kept
talking about how scared Tessa was and how easy it was to make him
commit more and more, deeper and deeper into being a full time
permanent sissy.
At work Laura called Bret into her office and told him to close the
door. He was nervous about the private meeting and showed it.
?Bret, you do know you are expected to present me with a new and
workable sales plan on Monday don?t you??
?Yes Laura I know that, you made it perfectly clear.?
?Do you have one??
?I?m working on it, I will, I will have it figured out by Monday.?
?I doubt it Bret, I don?t think you have it in you. Do you want to
resign now or wait until Monday to get fired??
?What the hell?you gave me until Monday I have until then; I will come
up with something.?
?You?re sure, you?re absolutely sure??
?Yes.?
?Would you be interested in some insurance or are you so sure you?re
willing to bet your job and maybe your career on it??
?What do you mean insurance??
Laura opened her lower right desk drawer and took out a pack of panties.
They were bikini cut and all different colors of pastels. They had some
lace on then and a ribbon on each side of the top of the leg was a bow.
?What the hell are those for??
?We can strike an agreement right now that you start wearing panties
every day until you have the sales up as I have said or on Monday if I
don?t like your plan you?re fired in front of everybody and escorted out
of the building. So how sure are you Bret? Do you start wearing panties
until sales are up or do you risk it all??
?What?s panties got to do with it, how?s that supposed to help in any
way? You?re just trying to humiliate me.?
?No I am not Bret but I can see where you would think that. I?m trying
to help you. I think you can be a great sales manager but I think you
have been part of the Old Boys club for so long you have forgotten how
to work, how to apply your brain to solve a problem and the panties will
help you by making you concentrate on the issues at hand. If you wear
the panties it will help you to focus on what?s important. It?s a proven
thing there is tons of research out there to support it. guys who wear
panties, and there are tons of them that do, are far better at getting
their jobs done and getting along with others, being more compassionate
and less of an ego manic. I can promise you that just a simple pair of
panties will eliminate your ego, temper ad machismo problems now do we
have a deal or not? Do you risk everything nor allow me to help you
become the best sales manager this company has ever seen??
?You?re serious??
?Yes Bret either you put on a pair of panties and wear them every day or
Monday you better be ready to totally impress me.?
?You really are serious and all you have to do on Monday is say you
don?t like my plan and I am screwed.?
?I will be honest Bret I promise you that. Look Bret, there are lots of
rewards coming to those that play along with me and you could earn some
of those rewards if you were to play along.?
Laura was a very beautiful woman, 5? 8? tall with naturally blond hair a
38, 26, 34 figure, stunning legs and sexy voice. Men tended to think
she
had the hot?s for them even though she never gave them any real reason
to think it. It was their own imaginations that hoped it was true there
for read anything they could they way they wanted it. Bret was no
exception and since Tom seemed to be out of the way he had the fantasy
of enjoying her. Like all men he was quite sure that he could tame her
and maybe even take over the company, after all he was the man and she
was well just a woman. He also did not have a clue as to what he was
going to do to get sales up but instead of putting the blame on himself
he told himself no matter what he did she would find fault and therefore
he would lose his job. He had just bought a new vet and new Harley and
if he lost his job he would lose his toys and his credit.
?Oh Ok I?ll do it, so what it doesn?t mean anything other than you can?t
just force me on a whim.?
?You made the right decision Bret. Now use my bathroom to change in.?
?You mean now??
?Yes Bret it starts right now or no deal.?
?You really are something, you know that Laura??
?Yes I am sure I am now go and do it.?
Bret picked up a pair of yellow panties and went to the rest room. He
was in there for quite a long time. Laura finally went to the door and
asked him if he was OK.
?Ya I?m ok things just don?t fit to well that?s all, I?m waiting, I?m
trying, and I?ll be out in a minute.?
Laura giggled to herself quickly figuring out that Bret?s dick liked the
panties more than he did and was reacting to them. She got a hanger and
poked it thought the door unlocking it and opening the door.
?What the hell Laura can?t I have some privacy, what the hell!?
?I?m sorry about your privacy but I understand your problem and I?m
going to help you with it that?s all.?
He stood there with his pants off wearing the yellow panties and his
cock making a huge tent in the front. She moved toward him and knelt
down and reached out taking hold of his hard cock through his panties
and holding it. The sensation was more than Bret could stand and it was
as if she had picked up a kitten by the scruff of the neck. He calmed
right down, his cock didn?t but he did. It felt so dammed good he could
not believe how good it felt.
She smiled up at him and said, ?Oh you have a nice cock Bret, I had no
idea, it?s so much bigger than Toms. And it?s so hard; it must really
like the feel of the panties to get that hard. Do you like how they feel
Bret??
?Yes it?s pretty nice,? he said slowly as she stroked his thing through
his panties.
?But Bret you?re not wearing it right, I need to fix this for you, is it
Ok if I fix your cock for you Bret??
?Y e s, g o a h e a d.?
?You see Bret we need to adjust it to fit in panties properly. So spread
your legs a bit.?
Laura then kept her left hand warped around his panty covered cock and
worked his testicles up inside his body, then she put pressure on his
cock to bend it back between his legs and give it a half twist so the
sensitive under head part was in contact with the panties silky feeling
material. Once it was in place she snuggled his panties up around his
hips holding his rigid dick in place against the panties keeping the
sensation alive. She reached around him and rubbed his pantied covered
bottom running her fingers between his legs and rubbing his cock head.
It felt marvelous to him and he never wanted it to stop.
?You see Bret; there can be many other rewards that go with your
cooperation and efforts. This is it for now but work hard and you can
receive a lot more of this kind of special attention from me, do you
understand what I am getting at Bret? You do realize I will need to
make a personal up and close examination of what you are warring
everyday and see how they feel on you don?t you??
?Every day? You mean you will be doing this every day??
?Well I don?t know about the ?this? part but I will be performing in-
depth inspections and they will probably get more in-depth as time goes
on if you know what I mean. They could eventually take considerable
time.?
?I?m starting to understand the benefits of this program Laura and maybe
I was a bit hasty on not wanting to be part of it.?
?I?m glad you?re starting to understand Bret. Now we both have work to
do.?
Laura dealt with all the things a typical CEO has to deal with the rest
of that Friday. She reminded all of the key people that Monday was to be
a big day and everyone better be ready for it. Bret seemed to have a
better attitude the rest of the day and as closing neared Laura felt
that after a week much progress had been made and the company was
working toward a successful turnaround. John?s firing had the desired
effect on the rest of the crew though there were still some guys from
the old boys club that bore watching. That was Carolyn?s job to be
Laura?s eyes and ears and let her know the pulse of the employees.
On their way home to Laura?s the two discussed various things. Laure
brought Carolyn up to speed on Bret which amused Carolyn to no end.
?What are you going to put all the male employees in skirts to Laura??
Carolyn asked with a giggle.
?No that?s not my intention but I certainly do like the results I have
had with Tom and I think t would be fun to petticoat other males as well
don?t you??
?Well I can tell you that I was never to fascinated by cross dressers or
female impersonators before I saw Tom all prettied up but I certainly
do
enjoy his feminization and subjugation so Ya, I think I would like to
explore it further. It?s nice to see how submissive and obedient they
can become. Do you ever see him being a man again Laura??
?What do you mean again? I?m of the belief that he NEVER was a man not a
real man anyway. But no his crazy idea that once he is trained he will
get to be a man again was his fantasy not my reality. I don?t ever
intend to let him wear pants again. He?s my sissy maid and soon to be
sissy maid cuckold and now with your little deal today he knows he
subjugated for four years that ought to work on his little pea brain
mind some.?
?You really plan to cuckold him??
?Yes, why not, he was seeing other women on me or a long time and I need
sex I mean I have my needs you know so why not, why shouldn?t I cuckold
him??
?Oh I?m not suggesting you shouldn?t just wondering that?s all, I would
love to be there when he finds out.?
?I don?t know if I can arrange that or not but I?ll consider it when the
time comes. You will get to be there when I discuss it though like I
will tell you about my dates in front of him.?
?Ohhh I can?t wait. Pay back is a bitch!?
?In this case Carolyn, payback is a Laura sissifying and cuckolding.?
They both laughed at that one and looked forward to the day Laura could
officially say she was a cuckoldress.
Upon arriving home they found a very obedient and humble sissy maid
Tessa waiting on them. She jumped to every command and was the perfect
sissy maid in every way. No hesitation no mistakes perfectly
concentrated on her tasks. After dinner the two ladies relaxed in the
living room and thought up ways to intimidate Tessa.
?Tessa?come in here.?
Tessa put up her dish towel and whipped her hands on her apron and
hurried in to curtsy to Ms. Laura and then to Ms. Carolyn.
?Tessa, I have been thinking about your eyebrows. I don?t like them,
they are way to manly so we need to do something about them as part of
your training. Carolyn, do you have time tomorrow to take Tessa to a
beauty parlor and get her eyebrows waxed??
Tessa started to squirm like she had to go pee. This idea was obviously
hitting a nerve and Laura loved it. Carolyn noticed the sissy?s reaction
as well and both women played on it.
?Yes I think I have time Laura, but what will she wear, I don?t think
it?s appropriate for her to wear a sissy maids uniform to a beauty
parlor do you??
Tessa sensed some hope here, of course it would be improper he should
get some pants and a shirt and men?s shoes at least.
?I suppose your right it?s not fair for me to send my sissy husband out
in a sissy maids outfit so everyone knows he?s a sissy maid. I saw some
yellow spring jumpers for sale at Target the other day. Maybe you could
run over there in the morning and get him one. A nice frilly blouse some
shores and a purse to match.?
Tessa?s heart sank as he heard his wife condemn him to public
feminization. He bit his lip fearing that if he argued or resisted he
would wake up in the morning with all of his manhood gone, cut off by a
sharp knife by a vindictive Carolyn.
?That sounds like fun; I?d love to do it. Does he have some pretty
yellow panties and a matching bra to wear with it??
?Oh I think he does, Tessa, go and get them and show them to Ms. Carolyn
and tell her how much you will enjoy getting a pretty yellow dress and
going with her to get your eyebrows done so she knows how much you
appreciate it.?
?Yes Ma?am,? Tessa said as he curtsied and left the room. His thoughts
were all about how utterly humiliating this wall was going to be. He
hated his situation and wanted out of it more than anything in the world
but he had no idea how to escape this silken prison he was being held
in! He quickly found the matching yellow panties and bra set and
returned to the ladies to show them.
The owed and awed over how cute he was going to look much to the sissy?s
embarrassment and dismay. Laura decided it was time for Tessa to go to
bed so told him to get changed and bring the toys. He reluctantly did
knowing what was in store for him. It was all pretty much a repeat of
the night before except the butt plug. Laura put the same one in which
did go in a bit easier than the night before and rubbed his bottom
afterward which he liked. After a few moments she worked the butt plug
in and out and then let it set again for a few moments. After this she
removed it and put in the next size bigger. He resisted as he felt it
start to hurt but she kept up steady pressure until it went in.
?Tessa you?re going to need to learn how to accept things in your ass.
When you go to Ms. Carolyn?s house she wants to peg you. Do you know
what pegging is my little sissy girl?
?No Ma?am I never heard of it.?
?Well sissy girl it?s when a woman wears the cock in the house and the
sissy, that?s you, bends over and takes it like a girl!?
?Yo, yo, you, mean she?s going to fuck me? Fuck me in the ass?? Tessa
blurted out in an amazed voice.
?Why yes dear, she thinks it?s only fair since you did it to her so many
times and I have to say I agree with her. So if we both think it?s a
good idea you should think it?s a good idea, so don?t you think it?s a
great idea Tessa??
It wasn?t bad enough he had to dress like, look like, act like a girl
now he had to get fucked like a girl too? He knew what he had to say
but he was having a very difficult time in saying it.
?Carolyn, just so I know, are you planning to use a little five incher
like Tessa has or a real man?s cock when you peg Tessa??
?Oh I wouldn?t do that to my worst enemy Laura. I know you know how
disgusting and frustrating and worthless a five incher is, no I will
certainly do it right, I will use at least an eight incher and more
probably an eight and a half incher on him so he knows there is a
something real in his bottom. I have a very nice, very realistic Black
one I can use on him.?
?Nice, I like it that you?re going to fuck him right as a little sissy I
think he really needs to be fucked right and regularly, so if you do it
when he is at your house and I do it here he will get all the sex he
needs and won?t have to be frustrated all the time like I was.?
Tessa could not believe how they were talking about him as if he were an
object. He never stopped to think that he had always treated women as
if
they were objects and how it made them feel. But now he was getting to
experience what it was like to be a woman and treated like an object or
being owned.
?Ok Tessa I want you to tell Ms. Carolyn how excited you are to get a
new dress tomorrow and then accompany her to get your eyebrows waxed and
I hope you make sure it sounds like you are truly looking forward to it
because if you don?t I may not happen into your room in the morning
next
time Carolyn gets the urge to use her razor sharp knife and who knows
what will happen if I don?t. Then I want you to ask her to lock your
penis gag in place, put your cuffs and leash on and put you in bed.?
?Yes Ma?am. Ms. Carolyn, I so excited about getting a new dress,
blouse, shoes and purse tomorrow. Thank you so much for getting those
things for me. I can?t wait to see how pretty I look in them. And then
for you to make a special trip to get my eyebrows waxed is so exciting I
just don?t know what to say other than thank you and how much I am
looking forward to it. And Ma?am if you don?t have any other use for me
would you please lock my penis gag in place, my cuffs on and put my
leash on my collar and put me in bed like you did last night Ma?am.?
?Why certainly sissy boy, anything to help you learn your place as an
inferior to women. You are learning your place aren?t you panty waist??
?Oh yes Ma?am I am learning very fast Ma?am, thank you for helping me to
learn Ms, Carolyn.?
Carolyn smiled at the pansy and finished getting him ready for bed. She
led him down the hall and put him in bed fastening his leash to the head
board and then leaning over him and whispering, ?it may not be tomorrow
or the next day but one day I WILL cut your cock and balls of my little
sissy dear, you will never know when until it happens and then of
course
it will be too late. Now have sweet sissy dreams little girl.?
Tessa?s eyes burst open with a panicked look as she quickly surveyed the
room, it must have been a dream, the picture in her mind of Carolyn
laughing heinously holding her severed dick in her hand with a knife in
her other hand. Her heart palpating still as she came to realize it had
only been a nightmare. It was not long before Carolyn entered her room
and smiled at her.
?I hope you had sweet dreams Tessa, I know I did.? Without further ado
released Tessa from her bonds. Strangely as soon as Tessa awoke she
started to suckle on the penis gag as if it were a pacifier. Without
even realizing it Tessa was still sucking on the penis gag. Carolyn
removed the penis gag last and found she had to instruct Tessa to stop
sucking on it so she could remove it.
?Ms. Laura wants you get breakfast for us and then while I go to the
store to get you your new sissy outfit you are to take a bath and make
sure you are in perfect feminine condition.?
?Thank you Ms. Carolyn, I will do exactly that. I am so looking forward
to my new sissy outfit and then going with you to get my eyebrows
waxed.?
?Oh I just bet you are but it?s good to know your such a big panty waist
that you don?t have the balls to say how you really feel. We really
don?t care you know, how you feel I mean, we don?t care at all, all we
care is that you learn to serve us a perfect sissy maid.?
?Yes Ma?am, thank you Ma?am,? Tessa said trying to ignore the terrible
masculine put down he had just received. He could not believe some of
the things he said or did either, they were so humiliating he was
devastated to even think he said them, but what could he do, he was
trapped and there was no way out for him. He wished he had lived his
life better and somehow he was now trying to atone for those mistakes by
being obedient. He came to realize he had been wrong, very, very wrong.
He had also come to realize he loved his wife and wanted to be a good
person and strangely being a sissy maid allowed him to do just that. To
become a good person, to serve, please, obey and sacrifice for others.
This gave him comfort in some distorted way. He was convinced that his
route to salvation lie in making it all up to his wife by being her
sissy maid or whatever she wanted. Yes it was difficult to stop being a
man and become a submissive girl, yes it was humiliating to be told and
ordered and controlled by women, no he did not want to be a girl or
subservient but the reality was this was what was being asked of him in
return for the pain he had caused and it made sense to him to submit to
it and provide what was being asked. He had seen glimmers of hope of
pleasure and satisfaction on his wife?s face as he complied with her
wishes and he liked those signs and wanted to see more.
Breakfast was served and the dishes removed and cleaned up. A quick
tiding of the kitchen and the living room from events that took place
after he had been put to bed and then seeing Ms. Carolyn to the door and
off on her shopping trip. He quickly went to the bathroom applied hair
removal cream waiting the appropriate time and then showering. Next he
started the water, poured in some feminine scented bubble bath and got
undressed. He required assistance in removing his corset which had
become somewhat looser over time. Ms. Laura was happy to help him with
that task and even felt his waist upon the removal remarking that it
seemed to have shrunk some. After drying off he rubbed lotion all over
his body, refreshed his makeup and made sure his nails were perfect. He
partially dressed putting on the matching yellow bra and panty set and
then asked Ms. Laura to help him with his corset. He slid on a pair of
nylons and finished up with his wig brushing it out properly.
?You are coming along quite well Tessa, I am actually very proud of you.
You are learning at a more rapid rate than I thought you would. It?s
too
bad about your agreeing to serve Ms. Carolyn for four years, that
certainly will affect your manhood considerably since you must remain
fully feminized at least until that period is over.?
?Oh Ms. Laura isn?t their anyway out of that, can?t you talk to her
about it??
?First Tessa, YOU made the deal and you must now stick to it. As a sissy
you may NEVER go back on your word or there will be severe
consequences.
Second, if I were you I would be more worried about her going back on
HER word and cutting your dick and balls of, she really DOES want to do
that you know and I think it will be all I can do to keep her from
finding some excuse to go ahead and do it.?
?Yes Ma?am, sorry Ma?am I didn?t meant to challenge anyone Ma?am.?
?Tessa you better understand your position here. You have nothing and
are nothing. If anything happens to you nobody is going to care or miss
you. You have to earn your place back and that starts with being a real
sissy maid. You are nothing more than an object or property right now
and you have to be very careful of what you do and what you say. Stay in
your station and you will be Ok but try to rise above it and you will
be
cut off at the knees and maybe elsewhere if you know what I mean!?
?Yes Ma?am I understand Ma?am thank you Ma?am.?
?Ok sit in the chair by the front door and wait for Ms. Carolyn like a
perfect lady. Cross your feet at your ankles keeping them slightly to
the side and then fold your hands neatly in your lap and sit there with
a smile on your face until she comes home.?
Tessa did as told for slightly over an hour at which time Carolyn
entered the house with several shopping bags. Tessa stood and gave her a
curtsy even without a skirt on to hold the hems out.
?Oh I like how sissy you re Tessa?here try these on?lest see how you
look.?
Tessa was actually excited about the idea of wearing something besides a
maids dress and such a pretty sissy outfit, matching shoes and shoulder
bag. There was even a piece of yellow ribbon that was used to tie a
sissy bow in Tessa?s hair. When she was dressed Laura was called into
the room and Tessa was made to model her outfit for the two ladies. It
suddenly dawned on Tessa that the two women always wore pants and she
was the only one who was always kept in skirts! This revelation made her
instantly feel more submissive and defeated. A feeling she was actually
beginning to enjoy as it allowed her to push out all of her masculine
feelings and enjoy the present.
?Let?s put some things in your purse, things that every girl should
carry.? Carolyn then gave her a compact, makeup kit, nail polish and
remover, hair brush, tissues, tampons, finger nail file and some hair
clips. The purse was much heavier now but Tessa liked the idea of
having the things in it.
?Ok Tessa, are you ready for your first sissy outing??
?Not really Ms. Laura I am scared, very scared.?
?Not to worry my pretty, Ms. Carolyn will take good care of you. You may
be sacred but you will learn to love it soon enough.?
Carolyn followed by the pantywaist left the house and walked to the car
got in drove off. It was not far to D?s Beauty Solon. Even though there
was a parking space right in front of the shop Carolyn parked several
blocks away and the two walked to the shop. Tessa was in a hurry feeling
very vulnerable out on the street but Carolyn took her good old time
stopping at many stores along the way to window shop. Bringing Tessa
into the conversation asking her what she thought about this or that or
which one she liked best.
When they finally arrived at D?s and went in Tessa was horrified to find
there were at least a dozen women in the solon. Carolyn took Tessa to
the check in station and the lady asked if she could help.
?Yes you can, I have a new customer her for you her name is Tessa.?
?Hi Tessa and welcome to D?s. I need your full name please.?
Tessa was terrified as she stood there while Carolyn and the clerk
waited for her to answer. Tessa tried to disguise her masculine voice
but it didn?t work and it was quite obvious she was a he! The clerk
looked at Carolyn with a questioning look.
?You see Miss. Tessa here is a sissy in transition. In fact he has been
a sissy less than a week now and his wife wants him to get his eyebrows
waxed so they are not so masculine looking. Tessa is going to be living
full time as woman now by his wife?s decree and it?s important for him
to look the part, can you help him??
You could have heard a pin drop in the solon, every female in there was
staring at Tessa and listening intently to be sure what they thought
they heard was really what they did hear.
?Why certainly, we cater to a lot of cross dressers, transgendered and
sissies like you. It?s just?well?your prettier than most of them. Let?s
put you with Vicki, she sissifies her husband so knows how to handle
customers like you a little better than some of the other girls. But I
need your information first.?
Tessa was a asked several questions and provided the answers but not
without a few of the ladies giggling and whispering about the newly
discovered sissy male at the counter. The two waited about 15 minutes
before Vicki was free and then went to her booth.
?We would like to have his eyebrows shaped into a the most feminine
shape you make them. You see Tessa here is a sissy and needs to be as
feminine as possible. This is a full time thing for her so you need not
worry about trying to make them unisex, just feminine as possible
please.?
?Oh how nice to meet you Tessa, I love sissies, I turned my husband into
a sissy and I am raising my son as one as well. I find sissies are so
much more pleasant, don?t get into trouble, obey and are anxious to
please, it?s a very nice situation for a woman like me. Are you a
cuckold too??
?No, no not a cuckold I am just a sissy Ma?am.?
?Oh to bad. My husband is a cuckold as well as sissy and he has come to
really appreciate how nice it is to be a sissy cuckold. Well maybe you
wife will see fit to cuckold you down the road a bit. It?s really the
best thing she could do for both of you, you know.?
Vicki had Tessa sit in the chair and laid the chair back. She studied
Tessa?s face for a few minutes deciding on what shape would look best.
?Ma?am, may I ask you a question??
?Yes you may Tessa, what is it??
?Your husband, did he want to be a sissy or a cuckold??
?No Tessa he did not, well at least at first he did not, why do you
ask??
?Well I don?t or rather I didn?t want to at first but now I don?t know
what I want.?
Vicki gave a little laugh, ?I would say that was pretty normal for a
guy. But you know Tessa my husband loves being my sissy maid cuckold
now, he really does. I can tell he is really happy to and I assure you I
am so much happier now than before, it has really worked out for us and
those in our group. I am sure you will love it as much as he does in
time.?
?You have a group??
?Well sort of, sissification and cuckoldry are pretty common today but
when I first started it was far less open and many of us felt alone or
like the lone ranger. You know, back then men were supposed to be men
and do only manly things and women were supposed to be obedient and
submissive and only obey their husbands. So when a woman like me took
charge in her home and ran things it was not so well accepted. But still
there were plenty of families in female led relationships and as we
discovered each other we stayed in contact and then formed support
groups. Not so much for the women but more for the men and boys that
were undergoing sissification and submission training.
On one hand we talk so strongly about equal rights and other equalities
under our laws but in reality we still put men above women as leaders.
It?s NOT politically correct to do so but it is operationally correct.
Men want to be in control and will do most anything to stop women. But
in a female led relationship we see a different dynamic. The woman is in
charge and the husband well he basically accepts the role of the wife
in
the family while the woman takes her position as the husband.
This brings about a lot of hysteria. For example it?s perfectly Ok for a
woman to have long hair, pretty nails, wear makeup and dresses and
heels, that?s fine and most think it?s proper and good. But put a male
into these things and people cry foul. They say you?re going to damage
him or that it?s cruel or mean. That people will make fun of him. WHY?
Why is it ok for a girl to be put into these situations and not a boy?
Ever wonder about that Tessa? Why will it harm a boy but it?s good for a
girl? The reason is it teaches boys that Girls are equal or better in
many circumstances. It?s hard for anyone to be dominant or commanding
when teetering in 5? heels wearing a frilly dress and a fine hair do.
You are wearing a dress, do you feel as tough and commanding as you did
when you were wearing pants??
?No, not at all Ma?am, I feel rather submissive and weak to tell you the
truth.?
?Exactly, so the feminization of males truly puts them on an equal level
with females and that scares the hell out of people. They talk a good
talk but the reality is most males are better of being followers and
begin led than the other way around. You probably don?t know it but
males have to be taught to lead. They are educated and directed and
pushed to be leaders. On the other hand little girls start out as
leaders they are bossy and controlling and are taught to take a back
stage to boys, to let them lead and are put down for being dominant. So
the natural tendency is for females to lead and males to follow so our
society is really screwed up and yet they are the ones that cry foul.?
?Ma?am did your son want to be a girl??
?I raised my son as a girl, he has never worn male attire. His older
sister helped me to bring him up doing as girls do. The exception was he
was not allowed to wear pants and his sister was. She taught him to
play
dolls and do big girl dress up. When he was still in grade school we met
a coupe in our support group where the father and son were being
sissified as well. So Candy my son and Lissa my friend?s son grew up
together as sissy girls. They are best friends today. Neither boy ever
got in any trouble, misbehaved, was a problem in any way. They made
darling little sisters to their big sisters and great daughters. Their
sisters had the advantage of growing up in a female led relationship
home and understanding the proper place for a male and how to train and
treat them. They are very well adjusted and have become very good
wives.?
?Did you say wives Ma?am, are they wives to men??
?No silly, my son is married to his best sissy friends Sister now and
his sissy friend is married to another young woman who was part of the
support group. They dress, act, serve and think like a proper submissive
wife should. It truly makes for a very perfect marriage?
?Are they happy Ma?am, I mean do they really like being girls??
?Now you understand Tessa that a sissy is not really a girl, it?s true
that a sissy looks and acts like a very submissive girl would or maybe
even more so but sissies cannot really be real girls.?
?Yes Ma?am sorry Ma?am but I mean do they like being sissies??
?Yes they do but don?t take my word for it Tessa, why don?t you and your
Ms. Laura and Carolyn if you want as well come to one of our get-
togethers and see for yourself, I think it would be good for all of you
to see how this really works in a real world application. You can get
some alone time with everyone as well and have a heart to heart about
it. That?s what this is for is to share and understand and assure
everyone that they are not alone in their situation whatever it might
be.?
?Thank you Ma?am, I will ask Ms. Laura if we can.?
Vicki worked on Tessa for a bit and soon turned her around to allow her
to see her reflection in the mirror. She showed her the new eyebrows and
Tessa instantly saw how much more feminine her face looked. It had been
a fairly attractive face before but now it was approaching a beautiful
face and Tessa liked it. She smiled giving away her feelings and Vicky
played on them by saying, ?Wow doesn?t that make a big difference,
you?re a very, very pretty sissy girl you know? You should ask your wife
to pierce your ears that would really help to finish off your
appearance
in a way that would be quite sexy.?
?She?s right Tessa, when we get back why don?t you ask Ms. Laura what
you can do to earn some piercings and some pretty earrings to wear.?
?Do you think she would? I mean allow me to get them Ms. Carolyn??
?I think she would if you asked nicely and volunteered to do something
nice for her.?
?Oh I hope she will I hope she will.?
Vicky looked at Carolyn and laughed, ?Their all the same so macho but
once they get started they love it and want to be just like real girls
or maybe I should say more girly than real girls. It?s amazing isn?t
it??
?Yes it is but it?s also a lot of fun.?
?You can say that again, my life is so much nicer since I turned my
husband and my son into sissies I only wish I had done it 15 years
sooner and my daughter loves it too, it truly is the best kept secret
there is.?
Carolyn paid the lady and the two left and headed back home. Laura was
surprised and pleased first to see the results and then the talk and
ideas about ear piercing.
?Oh please Ms. Laura you said you wanted me to be perfectly feminine and
Ms. Vicki thinks this would really help to do that could I please get
my
ears pierced? And she invited all of us to a support group can we go Ms.
Laura, please??
?Well what?s gotten into you Tessa you seem so anxious now to become a
girl what happened??
?Oh I just guess I realize that your right and I want to make you
happy.?
?Well Ok very well, there is some yard work that needs to be done in the
front yard and if you will do that this week you can get your ears
pierced next weekend. But we will have to get you an appropriate outfit
to wear, maybe a blue jean dress, a short one of course so when you bend
if you bend to far your panties will show this way you will have to
stay
conscious of your posture and maybe some powder blue tennis shoes and to
make absolutely sure you a conscious of Ass Awareness, a vibrating butt
plug. Yes why don?t you two go back out shopping and get those things?
There is an adult toy store over on 29th and I think Olive Street you
should be able to get the vibrating butt plug there. Is that ok with you
Carolyn??
?Sure sounds like fun to me lets go Tessa.?
Tessa hurried out the door behind Carolyn as anxious to get the things
as anyone though not to sure about the vibrating butt plug part.
Carolyn took Tessa to a woman?s wear store and they searched for a blue
jean dress finally finding one with the help of a female clerk. Carolyn
feeling she needed to make full disclosure to the clerk before allowing
Tessa to enter the dressing rooms said, ?Miss, I must tell you that
Tessa here is a sissy and not a real girl but I would like for her to
try on this dress to make sure it fits her properly?where can she do
that??
The clerk eyed Tessa and then looked back at Carolyn, ?thank you for
saying something some of our clients would not be too happy if we
allowed a ma?well a guy into the dressing rooms but we do get sissies in
here occasionally and we usually allow them to use the back room to try
on things in, if you will follow me please.?
As they walked to the back the clerk asked, ?How long have you been a
sissy??
?Not quite a week Ma?am.?
The clerk stopped and her mouth dropped open, ?Did you say not quite a
week??
?Yes Ma?am.?
The clerk looked Tessa up an down back and forth and looked to Carolyn
several times, ?You must not have been much of a man to begin with, you
seem like you have been a sissy for a long time to me. It?s pretty hard
to believe that you have been doing this for only a week.?
Carolyn butted in, ?It?s true?what he says, but there are some
extenuating circumstances that have greatly encouraged him to embrace
his sissification.?
?I guess?well here you are, there shouldn?t be anybody coming back here
to bother you.?
?Do you mind staying and helping in case we need to do something
different??
?Really? I mean yes I can were not that busy at the moment, I can stay
and help if that?s what you want,? the clerk said with a smile. Like
most women the idea of seeing a guy dressing up as a girl was always
something interesting and like most women again she was as curious as
any cat. Tessa looked at Carolyn with surprise when she invited the
clerk and her face begin to turn shades of red.
?Well Tessa?get your dress off and try this one on.?
Tessa looked back and forth between the two women but did as told
removing her jumper and blouse. She stood there for a few moments in her
feminine under things fully exposed to the two women as Carolyn seemed
to be holding back the new dress just to see Tessa exposed as she was.
In reading the stories and letters that Ms. Laura had given her on
sissification, maid things and cuckolding Tessa had read an account
about Sissie Maid Cuckold being taken to a storage room by his wife
Madam Rebecca while on their honeymoon and made to try on multiple
outfits in front of a store clerk and several other clerks that seemed
to need something from the store room. He had been exposed in much the
same way and Tessa?s predicament reminded him of that particular event
he had read about. He wondered if at any moment the door would fly pen
and a bunch of curious women would enter to gawk at him.
After the two figured they had admired the sissy?s pretty things and
feminine form long enough, Carolyn handed him the dress and had him try
it on. It fit perfectly and needed only some shoes to match. Since this
store did not have shoes they would need to go elsewhere.
?May he wear the dress out, we need to choose some shoes and it would be
easier if he were wearing the proper dress??
?Yes of course you may, those yellow heels surely don?t go with that
outfit.?
?Neither does that yellow purse!? replied Carolyn.
They paid for the dress and left only to walk about a block to a shoe
store. The clerk was a sort of geeky male in his early 20?s and upon
seeing two pretty girls come in he rushed to greet them.
?Hello ladies may I help you find something??
?Yes we need some flats to match this dress Tessa has on, something
suitable for outside work.?
?I?m sure we can find something suitable, why don?t you sit here and
let?s start by getting a shoe size.?
Tessa sat and the clerk dropped to his knees and undid her heel ankle
strap and removed it. It was obvious he was enjoying his job and
probably had a foot fetish from the way he seemed to really take his
time dealing with Tessa?s feet. He measured her feet and it turned out
to be a woman?s size 10. He smiled up at her and asked her, her name.
Carolyn hearing and seeing what was going on was not sure she wanted
this guy to know exactly what the score was so she butted in. ?Her Name
is Tessa and she is VERY shy.?
This only seemed to embolden the clerk and he replied, ?That?s ok I like
shy girls. Especially shy girls with pretty feet.?
He got up and left and returned with several pairs of blue ladies shoes
mostly in tennis style but also had some that were open toed heels. The
open toed heels did not match at all what had been requested but he
insisted on