A place to collect the thoughts and experiences of heterosexual male cross dressers and transvestites. I try not to be judgemental - hell I was forty-something before I liked myself. I WILL plug the page where I have books to sell - but there are 'freebies' there as well so money isn't a big deal.
I'm ancient - so have many years behind me. With any luck I've learned some sense about myself and the subject of transvestism. Have no problem in learning more. Want to, as a matter of fact.
Below is the final
part of the Rose and Jackie part of this story. It is much longer than the
previous episode and could have been twice as long if I had expanded on certain parts
of the story( there were so many possibilities) but as I said in a previous
post I don’t want this to turn into War and Peace as I think people would get
very bored, very quickly. Without giving away the ending I tried to manage it
in such a way that whoever picks up the story will hopefully be able to explore
their own plotline and hopefully what went on in these episodes will not adversely affect
their own storyline too much.
Thank you again to the Anon contributors and Rocket Dave for
their kind words and encouragement I would not have persisted with it without
the support. Also to those who found it interesting. Loved the idea of a movie,
would be great to see who would play the various parts. I’m also very jealous
of Anon who posted the comment regarding
“bossy mistresses like mine” Lucky girl.
Enough of the waffle – hope you enjoy it.
Rose and Jack Part 5 - The conclusion
Jack woke even before the alarm rang, he’d had a restless
night. The events of the night before were racing through his mind. The limited
intimacy he’d had with girls, kissing, light petting had not prepared him for
what he’d experienced the previous evening and even though he was unable to achieve
orgasm due to the confinement of his genitals within his cursed girdle, the experience
while exhaustive had also been wondrous. After she had spent what seemed like
hours teaching him how to pleasure her using only his tongue she had dismissed him
to spend the night alone and if he had thought his sojourn in feminine clothing
would be over at the end of the day he was very much mistaken. Before he was dispatched
to his room she ensured he was suitably secured in formidable foundation wear
consisting of a corselette secured by a slim chain through the shoulder straps
and locked to a collar at the neck. This was worn over a high waisted firm
control girdle with his member tucked firmly between his legs. It would be
impossible to remove. He could rub the mound between his legs but this would
only serve to persecute him even further knowing he could gain no relief. Over
these forbidding garments she placed an elaborate full length pale pink
nightgown with diaphanous sleeves, the body of the gown had two layers, a filmy
soft chiffon outer layer and a satin inner one. Fussing over him arranging his
ultra- feminine nightwear she stood so close to him, her breasts pressed against
his chest. As she fondled him gently between his legs she watched him squirm
and writhe as he emitted low moans of pleasure. When his legs could barely
support him anymore she kissed him on the forehead before consigning him to a
night of exquisite torment wrapped in his cocoon of the softest feminine night
Now that he was fully awake the soft folds of the nightgown
were still sending waves of unfulfilled pleasure throughout his body but he
knew he had to dress himself in his lady’s maid uniform and present himself to
Rose or Madam as she was now to be addressed as. Looking at the dreaded garment
on its hanger he knew that he would escape from the nightgown only to
incarcerate himself in the prison of his new uniform. He knew his appearance
had to be faultless, his apron arranged correctly, falling just above the hem
of the skirt a large bow tying it at the back, his cap perfectly placed on his
head, the seams of his pantyhose straight. Rose had left him in no doubt she
would not tolerate anything less than a perfect presentation. Divesting himself
of his nightgown he slowly pulled his pantyhose into place over the restrictive
foundation wear, stepped into his slip adjusting the straps as he did so. He
lifted the velvet uniform dress over his head and let it fall before zipping
himself into it, he then arranged the apron and cap in the correct manner to
complete the ensemble.He surprised
himself at the speed at which he completed dressing but knew it was as a result
of Rose having him perform it several times over the course of the previous
day. She had him practice walking in higher heels, putting on and removing
make-up particularly applying lipstick with a compact mirror. The words
“practice makes perfect” were still ringing in his ears but at least they were
alone, it took him hours to recover from the experience with Pamela and he
wouldn’t want to go through that again. He looked in the mirror making minor
adjustments to his uniform and thought to himself thank heavens it’s Sunday she
won’t have him working in the students rooms and his mother will be home later
so hopefully this charade won’t last too much longer. The tinkle of Rose’s bell
shook him from his daydream and he slipped on his increasing familiar heels and
minced his way to his mother’s room where Rose awaited.
For some strange reason he noticed his attitude appeared to
change from the time he left his room. He did not know whether it was the tight
foundation wear, the caressing of the satin slip against his thighs, the
servant’s uniform or the fear she would expose him but whatever it was as he
arrived at her door his demeanour had reverted to that of a servant girl.
“Good morning Madam” he said politely accompanied by the
obligatory curtsy “you rang?”
Rose was sitting upright in the bed and was wearing a
similar nightgown to the one he had also worn her prominent breasts filling its
“Turn around girl, let me see if you’re dressed properly”
After she was satisfied she issued him his orders, draw her
bath, tidy downstairs and his room, prepare breakfast of coffee and toast which
he was to eat alone in the kitchen while she had her bath she would ring for
him when she required him and he was to serve a similar breakfast to her. She
delivered these commands in quite a pleasant voice not at all arrogant or
condescending. It was as if it was a normal everyday occurrence, a mistress
speaking to her maid. He received her instructions with no resentment just an
acceptance of their new roles. It was as if his subservience was an extension
of his uniform. After he had drawn her bath he returned to the bedroom.
“Will that be all Madam?”
“Yes Elizabeth, I thought I may allow you out of your
uniform later, would you like that?”
He couldn’t believe his ears, finally he would be allowed
out of these infernal clothes and back to his own and some semblance of
“Oh yes Madam that would be wonderful” he gushed.
“Pity I rather liked having you as my maid but it is a
Sunday and even maids deserve some time off, well you’re not finished yet, get
on with your work, girl” she retorted.
“Yes Madam, thank you Madam” Jack beamed and gave an even
deeper curtsy to show his gratitude.
Rose dismissed him with a wave of her hand, one hour more
maybe, he thought and this nightmare would be over. He left her presence to
undertake his tasks with a much lighter attitude. He barely felt the time go by
such was his excitement and when he heard her bell put her breakfast on a tray
and climbed the stairs for the last time dressed as a servant girl.
Entering the room he placed the tray on the table by the
window where she was sitting dressed in her robe and speaking on the phone. He
immediately knew it was his mother.
“Yes Mrs Swanson…… he’s been a darling…….yes, yes, very
co-operative….. no trouble at all. Of course tomorrow will be fine, no rush”
Rose said updating Jack’s mother and after a few more words handed the phone to
Even though she couldn’t see him he felt extremely
embarrassed dressed as he was speaking to his mother.
“Oh! tomorrow, no I just thought it would be today, no that’s
fine everything’s ok. Yes of course I’ll be good” he answered her and just happened
to catch Rose’s eye as he replied to his mother’s last question.
“Yes I’ll do what she says” he mumbled and handed the
receiver back to Rose.
“I agree…… yes of course Madam……. see you tomorrow.” Rose
finished the conversation.
“It seems your mother
doesn’t want you watching TV for the day, left it up to me to organise
something for you” she announced.
Jack wasn’t entirely happy, would have preferred a day
relaxing in front of the TV after the trauma of the last 36 hours or so but at
least whatever she had planned it couldn’t be any worse than what he had
“I think before we decide what to do for the day you’d
better have a shower, take off your uniform and I will unlock your corselette
chain” she said
While the chain confining him to the corselette was
unobtrusive it was still a symbol of his servitude and he was grateful that she
was removing it. He quickly removed the uniform dress to allow her to open the
lock. Standing there in his slip he turned to go to his own room to shower.
“I think it’s best if you shower here” she said, and added
somewhat impatiently “well come along get undressed we haven’t got all day,
there’s a robe on the bed if you’re that shy.”
He divested his slip, eased off the straps of the corselette
and pulled it down around his ankles he had to sit on the bed to remove his
pantyhose, leaving just the high waisted girdle. Embarrassed he turned around
and struggled out of it and quickly pulled on the satin quilted burgundy robe
which he immediately recognised as his mother’s. Rose watched all this with open
amusement, much to his discomfort. Smiling she waved him to the bathroom and he
returned from his shower he found her sitting at the dressing table.
“You may help me dress I have laid out my underwear on the
chaise longue” she told him, “fetch them”
He could feel his heart beat faster, last evening came
rushing back, the way she’d ordered him to his knees to perform an act that he
had only heard spoken about by his own adolescent peer group none of whom had
ever experienced it.He’d remembered she
said it was the way girls made love and she would only allow him to do it if he
thought he was girl enough. Lust had engulfed him and he shamefully admitted he
girl enough. Would she impose herself on him again, would he find himself on
his knees before her, kissing her in the most intimate place imaginable? Her
words still rang in his ears
“Higher, a little more, that’s it, now a little faster” followed
by low moans then she almost smothered him with her thighs as she writhed
uncontrollably on the bed before relaxing and allowing him at last to breath
air that did not contain the scent of a woman.
With all this still fresh in his memory his legs trembled
slightly as he gathered the delicate panties, the more formidable girdle and
bra and held them out for her. Taking the panties and holding them between
thumb and forefinger she said
“You may not be in uniform but you are still my maid”
He knew what was required of him and dropped to his knees
and held them out for her to step into and when she had he pulled them gently
up her thighs until his face was in line with her vulva.
“Not just yet Elizabeth” she said as if reading his mind “now
fetch my bra sweetie”.
She pulled the panties into place and almost reluctantly he
got to his feet and gave her the bra, into which she placed her arms and unbidden
he fastened it. Without her even asking for it he brought the girdle and once
again silently assumed his position on his knees and held it open for her to
step into. Like the panties he pulled the girdle up her thighs and struggled to
“You’re becoming quite an accomplished lady’s maid” Rose
purred “now zip me up like a good girl”
He said nothing but blushed furiously knowing she was right.
He handed her the stockings which she eased up first her right then left leg
and again without instruction he began fastening them to the girdle’s garters.
She sat on the bed, laid her satin slip over her lap and
patted the bed indicating him to sit.
“You like the feeling of ladies underwear, don’t you Jack?”
she said surprising him by using his masculine name for the first time and
placed his hand on the slip moving it up and down rhythmically , quickly adding
“Don’t lie to me, your little thingy down there will tell
He had no option as his growing erection would make a liar
“Yes I suppose so” he mumbled beetroot with shame.
“I thought so, that’s a good girl, nothing to be embarrassed
about” she quietly said.
She took a pair of white satin panties from underneath her
and held them to his nose waiting for him to inhale then she deftly removed
them and slid her hand under his robe and stroked his erection with the
“You liked making love to me like a girl Jack?”
“Yes” he stammered his excitement growing with each slow
“You like wearing girl’s clothes?” she continued now
squeezing him gently as she stroked him
“Yes, yes” he struggled, his mind in turmoil and barely able
to contain himself.
“Like to stay in them a little longer?” she whispered,
increasing the pressure slightly.
“Y…es, y….es” his voice cracking.
“Good girl, now what’s your name” she breathed in his ear as
she gently squeezed him bringing to the point of no return.
“Elizabeth” he moaned.
“N….ooh, Elizabeth, my name is Elizabeth” he panted
“That’s a good girl” she said triumphantly and gave him a
final squeeze and as his whole body convulsed he climaxed into the panties,
collapsing on the bed he panted and gasped for air. She relaxed her grip and
wiped his penis clean with the panties. He didn’t know how long he lay there
eyes closed, totally spent physically and emotionally but when he opened his
eyes he saw her busying herself laying out clothes on the bed beside him. He
suddenly got a horrible feeling in the pit of his stomach.
“I’d better go and get dressed” he said sheepishly.
“Oh there’s no need to go anywhere……………….” she said and
paused before adding the word that caused him to wince,
“But you said I could dress in my own clothes” he answered,
now more in hope than expectation.
She stood above him arms folded and gave him that
“Oh that was before you said you liked wearing girl’s
clothes, liked making love as a girl and told me your name was Elizabeth” she
shot back and continued in a clam confident voice
“Of course you’re perfectly free to dress in your own
clothes but remember not only do I have your written and signed apology for
your disgraceful behaviour I now have your mother’s panties soiled with
your semen. While you were recuperating from your little accident I hid them
both where you’ll never find them. So what’s it to be …………..Elizabeth?”
He bowed his head and his face gave the answer his voice
“I thought so” Rose said “now let’s get you gussied up, take
off your robe”
He slipped off the robe and was so defeated did not even attempt
to cover himself. She quickly set to work fastening a garter belt around his
waist, had him struggle into a new high waisted girdle, smoothed stockings up
his hairless adolescent legs and attached them to the garters, fixed
breast-forms to his chest with an adhesive and hooked him into his bra, had him
put on an ivory satin slip before putting him into a tight knee length black
pencil skirt with a cream silk blouse. A pair of three inch heels completed his
outfit. She applied discreet make-up and lipstick and fastened a tight necklace
around his neck with matching clip on earrings. After brushing his hair into an
appropriate feminine style she led him to the mirror. By now his reflection was
no major surprise except he looked even more feminine as a result of the breast
forms which accentuated his small waist. Slipping on a matching jacket and
handing him a purse she said
“Much better, now your mother insisted you leave the house
today so time to go sweetie and as not to attract too much attention to
yourself you may revert to addressing me as Rose.”
Still in shock from what had just happened and her
continuing hold over him, Jack meekly followed her downstairs. He had a
horrible feeling this would be just as nerve wracking as yesterday. Getting
into the car proved to be a struggle as the skirt wouldn’t allow him to spread
his legs as a male would usually do, he had to sit on the seat and swing his
legs into the car just as he’d seen his mother do numerous times. Rose said
nothing but gave him a knowing smile. She suggested they have brunch in a quite
café just to acclimatise Jack to his surroundings dressed as a girl. As she
expected and much to Jack’s relief the waitress detected nothing unusual about
the two girls she served.
“I’d thought we’d do something girly for the day, visit a
nail bar, perhaps get a makeover at a big department store, maybe get your hair
done? What would you like to do?” Rose said widening her eyes almost daring him
to refuse and when he hesitated she offered
“You might enjoy an hour or two in a hair salon I could do
some shopping while you got to know the girls and the delights of having your
hair done like a real girl.”
Jack began to panic that she might actually bring him to a
hair salon and knew he had to pick the lesser evil. He thought that if he
sounded somewhat enthusiastic he might avoid the nightmare scenario.
“The nail salon” he said and added quickly to please her
“I’d like to have my nails done”
“Pity” she said feigning disappointment “I’d really love to
see your hair in rollers and then spending time under a dryer with the other
girls. But it’s your day, you’re the boss, the nail bar it is. Maybe another
He felt horrified that he had heard himself say he’d like to
have his nails done, whatever that was, but relieved that he would not be
subjected to the horror of the hair salon. Rose seemed pleased he thought and
at least that was something. After leaving the café Rose guided him through the
mall stopping here and there window shopping remarking all the time that no one
had stared and if he remembered his lessons from yesterday he would be fine.
Despite her confidence in his ability to pass as a girl he still felt extremely
uneasy. Entering the Rouge Nail and Beauty Salon and seeing the hive of female
activity served only to heighten his anxiety, he stayed behind Rose as she spoke
to the receptionist. They were seated at tables side by side with a variety of
bottles, tubes, gels, brushes and other paraphernalia and were soon joined by
two young women who greeted them warmly, Rose gave them instructions which
sounded totally alien to Jack’s ears. The girl in front of Jack took his left
hand and began working on his nails.
“They’re long enough I should be able to get a decent shape” she
said concentrating on the hand and not looking at him. Rose sitting next to him
“Oh she’s a real tomboy, this is her first visit to a salon,
maybe a nice oval shape, probably too soon for a French manicure like yours.”
Jack was appalled by Rose referring to him as “she” and a
“tomboy” but just gave a weak smile to keep up the charade. He looked at the
talons on the assistant and could feel his hand shake in hers. The girl looked
at Jack and gave him a friendly reassuring smile.
“Don’t be nervous Miss” she said “your first time can be
daunting, I’ll take good care of you”
She proceeded to file his nails into a distinctly oval shape
and began rubbing gel into them, soaking them in warm water and then used
different implements on the cuticles then rubbing more gel and creams. All the
while telling him what she was doing her voice was soothing and he began to
relax despite what was happening to him. After she applied what she said was a
base coat she asked him what colour he would like. Rose again interjected.
“Nothing too racy or obvious” she said “we don’t want her
looking like a hooker, some understated perhaps but quite feminine.”
“This colour is just the thing it’s called Soft Rose” she
“I think that would be perfect” she beamed “what do you
Jack could only silently nod his acceptance and knowing that
he would now have to wear nail polish colour bearing his tormentor’s name
served only to further increase his humiliation. It was like he was being branded
with her name, as if she was claiming him as her own.
“Excellent choice Madam” the girl said and set to work applying
Rose’s stamp on his nails.
Finally after what seemed to be an age the girl finished his
nails which now were decidedly feminine and as he straightened his skirt after
rising from the chair he could see the contrast of his newly coloured nails
against the black of the skirt. Rose paid the receptionist and they left. Jack
wondered how long more before he would be allowed back to the safety of the
house but as he soon realised it would be for some time yet as Rose steered him
through the mall gazing at various women’s stores as they went. They all seemed
to blend into one until she stopped outside of That Dress Boutique. He got that
now familiar queasiness in the pit of his stomach when he just knew something
horrible was about to happen. She firmly guided him into the store where his
senses were almost overloaded by the sheer femininity he encountered, racks of
dresses,gowns, shoes, lingerie and much
more besides. After spending some time browsing through some racks of dresses
they were approached by a saleslady offering assistance.
“I have a very special occasion coming up shortly and I’m
looking for something suitable this young lady.” Rose said by way of
explanation gesturing at Jack. He felt the blood drain from his face and had to
hold on to a chair for support.
“Oh I’m sure we can find something special for her, right
this way” she said.
Rose had to prise Jack’s hands from the chair and he was
forcibly manoeuvred into following the assistant to a very large area at the
back of the store where the fitting rooms and mirrored viewing area were
situated. It was dotted with sofas, women and girls were trying on dresses.
Jack did his best to remain calm as Rose and the woman chatted amicably about
dress sizes and colours.
“If you take a seat I’ll bring some gowns that I think would
suit” the assistant said
“Rose, please don’t make me do this, please I beg you.” Jack
pleaded after she left.
“Elizabeth, we’re just two girls trying on dresses like
everyone else here, you’ve been a good girl up to now so please don’t make it any
worse for yourself ” Rose snapped leaving him in no doubt as to her intentions
should he cause her further annoyance. He looked around and was amazed to see
women in various states of undress none of them taking any notice of Rose or
He resigned himself to his fate which would soon become
apparent. The saleslady appeared shortly after rolling a dress rack with gowns
of various colours.
“Would you like some assistance” she asked, Rose thanked her
and said they would be fine. She took a dress from the rack and beckoned Jack
into the changing cubicle where she had him remove his dress and gave him a strapless
knee length red satin dress with overlaying tulle. She then led him outside and
had him parade up and down. As he was doing this the saleslady approached Rose
and they had a brief conversation and the Rose approached him slightly
“It seems some idiot has set my car alarm off, I need to
turn it off, I’ll be back shortly, stay calm remember all I’ve taught you and
you’ll be fine as you can see no one suspects so just sit tight until I
She left in a hurry and he sat on the sofa immobile with fright,
eyes fixed on the floor for fear of making eye contact with any of the women. A
pair of shapely legs perched on four inch heels appeared in his line of vision
and a shiver went up his spine when he heard a familiar voice.
“Well, well if it isn’t my favourite servant girl all
gussied up to look like a lady.”
He looked up to confirm his worst fears, Pamela was standing
over him arms folded with a smirk on her face.
“I.. I .. I’m just waiting for Rose” he stammered unable to
think of anything else.
“Yes I know you are, I’ve been watching you. You two seem
inseparable, such a pity her car alarm went off, I wonder who could have done
such a thing” she said with a sly grin and sitting herself next to him on the
sofa. She continued
“Anyway I’m glad we’ve got this chance to get to know one
another….alone” she purred placing her hand on his thigh and caressing it through
the rich material of the dress.
“You’re quite a pretty little thing, but I don’t think that
dress suits you why not try the pink one, much more girly” she said pointing to
a dress on the rack.
“Maybe we should wait for Rose” he said
“I do hope you’re not going to argue with me, girl”
“I just think … “he began but she cut him short.
“You’re a maid, you don’t think, now get in there and take
off that dress, I’ll be there in a moment” she spat.
“But what about Rose?” he said
“Never mind Rose, now
do as I say” she said in a tone that scared him
He knew what she was capable of, meekly he picked up the
dress and entered the changing room and began to undress and was down to his
slip when she entered with a mass of fabric in her arms.
“I’m not used to being spoken back to” she began “I think
it’s time you learnt what happens to those who defy me, now come here this
She sat down and motioned him towards her patting her knee.
“Get yourself over my knee if you don’t I can make life very
difficult for you and Rose” she threatened.
Not having Rose to rely on and knowing what she was capable
of he capitulated and submissively draped himself over her knee.
“This won’t be painful but it will teach you your place and
not to question me in future” she said and began to spank him intending more to
humiliate than hurt him.
It has the desired effect, she quickly had him step into a six
layered black petticoat and as he stood there totally under her thumb she
lifted the pink taffeta dress over his head at quickly zipped him in.
“Perfect” she said let’s see you walk in it.
She led him outside and had him walk up and down, the
rustling of the petticoats against the taffeta ringing in his ears as he
walked. As he walked back to her she took his arm and looked at it intently.
“Now that’s a coincidence” she said “I’ve seen a birthmark
like that in on someone else recently”
He could hardly believe his ears and said
“Lots of people have birthmarks”
“Yes they have” she said and examining the back of his neck
“but what are the chances of two people having a similar one here as well”
Jack remained silent, eyes downcast.
“I knew there was something familiar about you, I just
couldn’t put my finger on it, Rose certainly did quite a job on you. Only for
this I would never have guessed, you really do make a good looking girl, I am
going to have so much fun with you Jackie, after I get rid of Rose of course.
Just wait until I tell the girls.”
“Elizabeth, his name is Elizabeth and you won’t be telling
anyone” Rose’s calm voice came from behind them “I’m not going anywhere anytime
“Elizabeth get changed back into your own clothes and then
come back here” Rose said authoritatively “myself and Pamela here need to have
Jack almost ran for the changing room thinking his heart
would explode. Everything was running through his brain, how could he live with
the shame, his mother would surely be fired. He quickly struggled to get out of
the dress and petticoat, after wearing that confection the skirt and blouse he
came in seemed quite normal.
He left the safety of the changing room and returned to Rose
“Pamela has something to say to you Elizabeth” Rose said
“I’m sorry for offending you Elizabeth, it won’t happen
again. No one else will hear of this.” she said in a low voice.
“You may go now Pamela” Rose said dismissing her as if she
was a servant.
Jack was astonished and after she left bombarded Rose with
“All in good time dear, didn’t I tell you not to be afraid, you’re
Rose’s girl now and no one else’s. Now let’s get a coffee before we go home”
He didn’t like the phrase “Rose’s girl” but was powerless to
question it for it was abundantly clear that is exactly what he now was. He was
in no doubt that he would prefer to be under Rose’s thumb than Pamela’s
Jack was still in shock at the events of the day
particularly the change in Pamela’s attitude and was relieved when they reached
home and Rose let him into the sanctuary of the house. Once inside Rose sat
down on the sofa and motioned Jack to sit beside her.
“Should I get into my uniform Miss Rose” he said remembering
that once inside he was to revert to his servant girl status.
“That won’t be necessary tonight Elizabeth” she said and
picked up the bell and rang it.
“You rang Madam”
Jack looked around and saw Pamela standing there dressed in his
housemaid’s uniform complete with cap and apron.
“As yes there you are girl, I think I’ll have some tea and
cucumber sandwiches” Rose said matter of factly.
“Yes Madam and you Miss Elizabeth” she said meekly as she
Jack was dumbfounded and noticed her blushing with shame and
embarrassment, he could only mumble
After she curtsied again he turned to Rose with a look of
utter amazement and before he could ask she said
“You recall when we were cleaning her room yesterday, I
found some, well shall we say various substances and some documents that the
police would find very interesting. The authorities take a serious view on such
matters, not only would she be expelled but it would probably also result in a
custodial sentence. I seriously doubt she would risk divulging our little
arrangement which now by the way includes her also.”
Jack suddenly felt conflicted, he felt a sigh of relief that
his secret would not be exposed but also a feeling of dread with the reference
to “our little arrangement.”
Pamela returned with the refreshments and after laying the
try on the table curtsied and clasped her hands together on her apron eyes
downcast awaiting further instructions.
“I think you have the makings of a good housemaid my girl”
For the first time despite his imprisonment in feminine
clothing Jack was becoming somewhat relaxed as he noticed that Pamela was
visibly humiliated by her situation but Rose was in no mood for compassion.
“Your shoes seem to be slightly scuffed from today’s outing
Elizabeth I think they require a touch up.”
He looked at her unsure of where this was going until she
nodded in Pamela’s direction, then it suddenly dawned on him what she wanted of
him and reaching on his experience of Rose’s role as a mistress in charge of a
maid he said
“On your knees girl you may clean my shoes” growing into his
role as Pamela’s superior.
Just as he had done on several occasions recently she
dropped to her knees and began to clean his shoes.
The next few hours progressed with Pamela experiencing
further humiliations at her tormentor’s hands. Eventually Rose told Pamela to
put on her own clothes and report back to her. She told both of them to stand
in front of her.
“Now my darlings, this is how it will be for the near
future” she said revealing her plans for both of them.
“I want you both to become, well not quite friends but
perhaps associates, colleagues if you will. Pamela needs to learn humility so
Elizabeth here will instruct her in the duties of a housemaid, naturally
dressed as a girl. Whereas Elizabeth needs to improve and refine his feminine
traits so Pamela will supervise him with these. These sessions will alternate
so if one of you is harsh on the other, the following session the aggrieved one
can return the favour. Agreed?”
Not that they had any choice both nodded.
“Excellent you may now kiss to seal the arrangement” Rose
Reluctantly both came together and kissed and to both their
surprise found it pleasurable and only stopped when Rose called a halt.
“That’s quite enough of that” she snapped
Pamela left shortly afterwards cursing herself for her
stupidity and wondering where all this would lead but at least she would now
have access to Jack. Rose put Jack to bed but only after he spent some time on
his knees furthering his education in the extra-curricular duties of a lady’s
Jack stretched his body, only half awake, what a horrible
dream he thought gradually the sensations of the familiar fabric of his soft
nightgown filtered into to his consciousness. He slowly opened his eyes horrified
to find his mother and Rose standing over his bed.
“Good morning dear” his mother said gently.
Jack now very much awake and aware of his feminine nightwear
began to stammer
“I … I can explain Mum”
“No need darling Rose has explained everything” she said.
“Everything?” he said
“Yes, you missed me so much you felt you could be closer to
me by wearing my nightgown. I never thought you were so sensitive such an
unusual trait in a boy. I should have been more attentive to your feelings. You
obviously want to get in touch with your feminine side. Rose suggested we go
shopping later and get you some beautiful nightgowns of your very own. Wouldn’t
you like that?”
Jack looked at Rose standing behind his mother and knew what
“Yes mum” he said
“Rose also suggested it would be a good idea if you
addressed me as Mummy from now on. What do you think?
“Yes Mummy” Jack said now firmly under another woman’s
“Thank you so much Rose, you obviously have a way with boys”
his mother said.
“Oh it was nothing Madam” Rose replied with a sweet smile.