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 second part of Amongst Women, it took a bit
longer than expected because as usual time was an issue. I suspect this may not
exactly be the continuation readers wanted/expected but please bear in mind
there will be a concluding episode and hopefully the last part of this episode
will give an idea of what is to come.
I don’t know if too people liked the visual pieces I’ve done
for Rose and Jack but an anonymous commenter to Rocket Dave’s last illustration
mentioned he liked them (thank you and I
agree about a pic painting a thousand words ) so I’ve done a piece for this
episode which I hope fits the bill.
Again many thanks to all those who commented either liked or found the
story interesting so far, I appreciate all the comments (apologies for the
typos in part 1 I just discovered them after rereading it for this one,
probably made a few in this episode as well) I just wish I could get the
episodes finished more quickly. One of the commenters also came up with the
idea of his mother hiring Jack out as a maid- what a great idea,would never
have thought of that and maybe that could happen in a future contribution. As usual any suggestions or comments however critical are
Amongst Women Part II
drifted away leaving only Jack and his mother he had to sit down as the full
implication of his participation in Pamela’s play sank in. There must be a male
role in the play surely they didn’t expect him to play a female part. He was
mulling over this when his mother interrupted his thoughts.
“What a nice
woman Pamela’s mother is” she said “she seems very taken with you, as
is Pamela. They were so grateful that you agreed to do the play, I’m so proud
he said “I’m not really sure it’s something that would be right for me. I don’t
even know what role it is” he replied trying to sound nonchalant but
desperately trying to find a way out.
clue is in the title” she said in an exasperated tone as if she was explaining
to a five year old.
are female roles” he said, the panic quite noticeable in his voice.
not unusual for actors to play roles of the opposite sex, it’s been going on
since Grecian times maybe earlier, all female leads in Shakespeare’s day were
performed by men and boys. Most juvenile male roles in opera are played by
girls and women. Performing as a member of the opposite sex really stretches an
actor, it requires talent to do so and I know you have talent” she informed
“But … I…
she…” he stammered but could not come up with an argument.
was a good drama teacher and had coached him since he could walk and he had won
awards in various productions, any argument he could make could be easilydismissed by her.
settled then” she said firmly adding “more importantly she is a very wealthy
and influential woman and has expressed an interest in making a generous
contribution to the drama department. Miss Strang will be very disappointed if anything
should jeopardise such an opportunity.”
He knew now
there was no way out of this predicament if he refused not only would his
mother be on his case but he would also have Miss Strang to deal with. Life
would not be worth living. His mother put her arms around his shoulders to
fine, you’re happy to embrace your feminine side, right?” she said
say no, Rose’s blackmail threat had already seen to that, he had no other
excuse for being discovered in her satin nightgown. He could only nod his
that’s settled and as we’re in lingerie store we may as well get you your own
nightgowns, after all you can’t go on wearing your Mummy’s now can you?”
The day had
turned into the shopping trip from hell he thought as his mother took his arm
and guided him towards the sleepwear section. As she browsed through the racks
discarding the pyjamas and the plain cotton nightgowns she chose the most
feminine of styles and materials .Much to his unease they were joined by
Michelle the store’s manager who seemed to have taken a keen interest in Jack.
“Can I be of
assistance Madam” she asked as Jack tried to hide among the racks still
smarting from his earlier encounter with her.
gorgeous” his mother gushed clearly enamoured with her choices.
are beautiful, so feminine I have these in your size just over here” she
replied pointing to a different rack close by.
they’re not for me, this size is perfect for who I have in mind” his mother
“Oh I see”
Michelle said glancing at Jack “ I don’t have a mannequin in the same size to
try it on but as your son is of a similar size perhaps he might help I know
it’s unusual but it would save you returning it if it doesn’t fit.
excellent idea” his mother said.
“No way. You
can’t be serious” Jack said finally drawing a line in the sand.
pleas Michelle continued
have this dressing room it’s out of sight no one will see you and it will save
your mother so much time and trouble. It should only take a few minutes.”
Jackie be reasonable” his mother pleaded “it would really help me out. Rose was
has told me how kind and cooperative you’ve been lately. I’m sure she’d be
disappointed to hear you could not do this one little thing for your Mummy”
of Rose threw Jack and the less she was involved in his life the better. The
women like wolves around a wounded deer sensed his weakness and indecisiveness
and before he had time to gather his thoughts the women each grabbed an arm and
guided him towards the dressing roomled
him inside and leftseveral nightgowns
in different colours and materials on the chair.
“Let us know
when you’re ready” Michelle said casually.
with no choice Jack disrobed and leaving his underwear and socks on quickly
slid satin burgundy nightgown over his head and called out indicating he was
ready for inspection.
“Yes it does
look even more beautiful on” his mother said “it is a little long and those
socks ruin the look.”
Michelle said “well that’s boys for you, absolutely no idea whatsoever.”
her head out of the door and called to someone, Jack was barely listening as he
was concentrating on not getting an erection, the satin material was sending
waves of pleasure through his body. He didn’t notice two sales assistants
arrive with some items.
off your socks and put these kitten heeled slippers on” Michelle said in an
authoritative voice as one of assistants held the matching slippers and gave him
a look which was somewhere between contempt and pity and as he slipped his
socks off she bent to place them on his feet.
stood back to inspect the nightgown and how it fell around the reluctant model
remarking how well it looked on him and how luxurious the material was.
“It’s a pity
she’s sorry I mean he’s not wearing a bra as we could get a better idea of how
the bust section would look on a real girl” Michelle said.
of that Madam” one of the assistants said and produced a bra and some breast
forms “these are breast forms we use for mastectomy customers”
thinking Marie” Michelle said and with a nod from his mother and before Jack
could say anything they had slipped down the shoulder straps of the nightgown
and fitted a strapless bra around him and placed the breast forms inside.
better, more of a shape.” his mother said, the others voiced their approval as
one of the assistants adjusted the breast forms. Jack stunned into silence and
completely mortified by this stage caught sight of himself in the mirror and it
very much looked as if the assistant was feeling up “his breasts” much in the
way a boy would do to a girl. At the sight of this and much to his shame he
could feel his erection returning and only for Michelle calling the girl away
it could have been even more embarrassing.
falls much better, turn around dear and walk away from us so we can see what
it’s like from the rear”
Jack did what he was told walking to the back of the room. He found he had to
hold the skirt of the night gown with his hands so as not to catch his slippers
in it and did the same when he was told to walk back to the group. The kitten
heels made him sway his hips ever so slightly.
quite quickly” Michelle said noting the feminine way in which Jack dealt with
the long skirt. His mother nodded approvingly as the assistants smiled, Jack
remained silent. Michelle continued the conversation with his mother as she
took another garment from one of the assistants
“Now to complete
the ensemble we have a matching quilted satin dressing gown, very retro and all
the rage, I think you will love it.”
She held out
the arms of the dressing gown and Jack now completely subjugated obediently
placed his arms inside. Deep quilted in a diamond pattern it had a fitted
styling with wide lapels the skirt was bias cut as one continuous piece. As she
tied the sash it accentuated his waist and gave the effect of him having female
his mother said “so stylish and elegant, I’ll take seven of each in various
Jack Michelle said “You’re a lucky boy to have such a generous mother.”
for me” Jack fumed, with as much indignation as he could muster under the
“Oh I wasn’t
suggesting that, I just said you have a generous mother, of course they’re not
for you how could they be, after all you are a boy and this is a girl’s
nightgown and robe.” Michelle said in an even tone while fussing about him
fixing the lapels, straightening the skirt, tightening the sash and all the
while admiring the figure in front of her as she made these little adjustments.
there’s nothing a bit feminine about you, is there girls?” she asked her
assistants who much to Jack’s annoyance smiled sweetly at him whilst agreeing
with their manager. She then ushered them out saying it was time Jack got
so much for your assistance” his mother said to Michelle
she replied “but it’s your son you should be thanking I’m sure he’s saved you a
lot of trouble and the girl that gets to wear these will be so lucky they will
make her feel so feminine.”
Jack was so
emotionally drained he had to sit down still draped in the ultra-feminine
“Now that wasn’t so bad was it?” his mother
please go now” he pleaded.
unless you want to try on the other nightgowns?” she smiled.
started to disrobe.
thought not” she said
mother paid for her purchases he practically ran out of the store before he was
subjected to further torture, much to the amusement of the assistants. He spent
the rest of the day recovering from his ordeal but now knowing he would be
spending his nights for the foreseeable future within the confines of his new
in the lingerie store seemed to humour his mother’s fixation withJack’s feminine side and apart from the
detested nightly parade in his new sleepwear life in the Swanson household
settled down to something approaching normality. As he started a new week in
school he redoubled his efforts to keep contact with Pamela to a minimum and
was reasonably successful as she seemed to be fully occupied with various
projects. He also figured out Rose’s work pattern and managed to avoid her
visits for the most part. Walking home from school on Friday afternoon his mind
wandered to what he might do over the weekend now at last his mother was off
his back he may get into town and finally hang out at the mall. Letting himself
into thehouse and while still in the
hallwayhe heard voices in the kitchen,
never a good sign he thought and became more alarmed as he got closer andrecognised them. He heard his mother, Pamela
and her mother yacking away anddeep
inconversation, time to leave he said
to himself, head into town and come back when the coast is clear. Quietly
retracing his steps along the hallway he had almost reached the door when he
heard another familiar voice.
avoiding me Elizabeth?” Rose said using the female name she had given him as
she stepped from the adjoining living room arms folded, he almost jumped out of
his skin with the fright. At first he didn’t recognise her, her hair was down
and she wasn’t wearing her uniform.
“No Rose” he
said sheepishly “been busy in school”
hate to think you were, we’ve become such good friends lately” she said giving
him a smile and added “but we’ll have plenty of time to get together in the
future, let’s go inside your mother has a surprise for you.”
familiar sinking feeling returned and all sorts of thoughts began racing
through his brain. His planned escape foiled he was marched under guard into
the kitchen to await his “surprise”.
you are Jackie” his mother greeted him. He remained silent and lookedat the assembled women as if they were a
has kindly given me tickets for the Opera festival close to her home. It’s
about a four hour drive and as luck would have it Rose is visiting her sister
who lives close by and has offered to give me a lift”his mother trilled. Jack didn’t like the
sound of this at all but before he could open his mouth his mother continued.
“As you have
agreed to take part in Pamela’s play she thought it would be an ideal
opportunity to rehearse at her house over the weekend. Isn’t that wonderful?
You’ll have the whole weekend together. ”
He felt his
knees weaken and had to hold on to a chair for support, he tried to raise a
protest but his mouth couldn’t get the words out. Mrs Quinn gave him a
sympathetic look and said
“I know it
is short notice Jackie but it’s a wonderful opportunity for your mother some of
the best singers in the world will be performing and we can get in some
you’ll be in good hands” his mother said “and be sure to behave and obey Mrs
Quinn. Now I’d better be going Rose wants to get there before dark. I’ve packed
a bag for you it’s in the living room.”
“Yes it will
be great to have Jackie all to myself for the weekend, we’ll have so much fun”
Pamela gushed to his mother.
much now Pamela remember you have a lot of rehearsing to do I’ll be looking
forward to seeing a dress rehearsal when I get home” his mother laughed.
left his mother drew him to one side and quietly said
Jackie it’s very important to the school and indeed to me that Mrs Quinn is
pleased with your performance and behaviour over the weekend. It could make a
huge difference and Miss Strang is also counting on you there’s a strong
possibility we may get a large donation.”
still reeling from the shock of being left with Pamela and her mother for the
weekend as he watched his own mother leave with Rose and after their car
disappeared around the corner he was ushered into the back of Mrs Quinn’s black
Mercedes.She had already explained that
she was staying with her sister while visiting Pamela but her sister was also
away for the weekend so they would have the house to themselves. The house
located in an exclusive community was quite large and stood in its own
extensive and immaculately manicured grounds and the interior was obviously
expensively decorated, he had never been in a house like it and immediately
felt intimidated by his new surroundings.
directed him into the large living room and asked Pamela to make some coffee.
probably wondering why I don’t get one of the maids to get the coffee. I gave
them the weekend off I thought it would be more intimate with just ourselves,
it will give us more time to get to know one another.” Mrs Quinn said as if
reading his thoughts and patting the seat next to her on the sofa she beckoned
Jack to join her.
looking forward to getting to know you better Jackie” she smiled at him gently
patting his knee “you have a very sensitive quality that is rare in boys these
days. I was most impressed with the way you conducted yourself at the lingerie
store most boys would have baulked at the idea of helping a woman with choosing
her lingerie but you embraced it.”
hell did this woman get this idea? I was practically forced into it Jack
thought but dared not express it, she continued
Pamela is very important to me and while I think it’s fair to say she may not
be the most feminine girl in the world I really do think an association, a
friendship if you will, with someone of your delicate sensibilities not to
mention your excellent taste in matters feminine would have a beneficial effect
on her. You will be her friend and help her, won’t you….. please?”
She looked at Jack with her expressive eyes
almost pleading with him. Jack didn’t like where this seemed to be going but
considering his circumstances particularly what his mother and Miss Strang’s
expectations were he had little choice. He just smiled and nodded.
Mrs Quinn squealed with delight “now this little play that we spoke about, your
mother says you are a good actor and Pamela has ambitions in that direction
also so I’m hoping we can improve her performance.”
no problem Mrs Quinn” Jack said suddenly getting a great idea of how to get out
of any potentially embarrassing situation “we can read the parts several times
over the weekendand Pamela should
easily be able to get a girl to play the other role at a later stage”
confident that Mrs Quinn would see this as the obvious way to proceed.
Jackie that won’t do at all, we need to immerse ourselves in the play, to
understand the characters. I’m a big admirer of the Method School of
Acting.You have the whole weekend to
get to grips with the character and the best way to do this is to inhabit the
“Do you mean
….” Jack trailed of afraid of saying what he thought.
said excitedly “you will become your character, live the part 24/7, it’s the
only way you can get to understand the persona. I think you will make a great
“And in full
uniform, you can showcase your acting skills, won’t it be exciting?” she
continued, her enthusiasm hitting him like a brick.
“But…I.. I’ve … never….. I mean…. Dress as…” he
“Dress as a
girl? Yes of course but how else could you play the part, whoever heard of a
male maid.” she giggled “Oh I know you haven’t done anything like this before
but this is very important to me and I can give you all the help you need and
I’m sure we can iron out any little problems you might think you have. It will
be fine, I really do hope you’re not going to disappoint me and perhaps Miss
Strang also….. now are you my dear?
expression changed and she fixed Jack with a steely look that left him in very
little doubt as to what was expected of him. He swallowed hard and admitted
Quinn” he quietly said, head bowed.
she crowed “ah, here’s Pamela with our coffee. Good news Pamela Jackie has
agreed to be your maid.”
down the tray and smiled at Jack.
doubted it Mother.” Pamela said.
As they sat
drinking coffee, the two women chatting excitedly between themselves Jack paid
little attention desperately trying to think of a way out of his latest
predicament. He drew a blank all avenues of escape had been cut off, just then
Mrs Quinn interrupted his thoughts.
don’t think you’ve been listening to us” she chided him as he looked at her
“You did say
you’ve never dressed as a girl before?” Mrs Quinn asked.
silly Mother. Of course he hasn’t” Pamela interjected with a nervous laugh. It
appeared Rose’s hold over Pamela was as firm as the one she held over him. This
was a secret they shared and it was in both their interests that it was kept
that way. Now that Mrs Quinn had his attention she continued.
you will wear will help you to capture the full feminine experience as well as
that of a servant girl. You may feel that some of them are more restrictive
than male clothing but I’m confident that you will soon become used to them.
Even though you appear to have much more of an affinity with the female psyche
than most boys you will still need to be instructed in feminine ways,
mannerisms, deportment etc. I know you haven’t read the script but the
backstory of your character in a nutshell is that she was quite wealthy but has
now fallen on hard times and has been forced to take a position as a maid to
one of her friends but at this stage that’s not as important as getting you
into character, now time we got started.”
Pamela followed Mrs Quinn out of the room and across the large entrance hall
and up the wide ornate staircase. As he walked behind her up the stairs he
couldn’t help noticing the sway of her ample hips tightly enveloped by her
steel grey pencil skirt, her shapely legs encased in grey stockings were
perched on four inch heels of a similar colour. His heart began to race as he
followed her into a luxurious bedroom decorated in a distinctly feminine
fashion. He noticed his case was sitting on the large satin quilted bed.
“Why don’t I
help you get unpacked” Mrs Quinn said and almost breaking his heart added “not
that you’ll need too much as I have most of what you’ll be wearing already in
could object Mrs Quinn opened the case and a broad smile crossed her face as
she took out one of the satin nightgowns his mother had bought him the previous
week and held it up to her body. He was speechless.
pretty nightgown” she said giving Jack a knowing look “somehow I don’t think
you’ll have much of a problem in adjusting to your new role.”
very fetching” Pamela agreed “I’m sure he looks adorable in it.”
He made no
reply and knew any protest he considered making about being dressed as a girl
would be rendered useless, he now had no choice but to surrender to whatever
Mrs Quinn and Pamela had in store for him.
other things she unpacked were his toiletries and the matching satin quilted
dressing gown, she stowed away the case in the large walk in closet.
“Now a nice
hot shower and then I can get you ready” she said pointing the way to the
bathroom.” Pamela and I need to sort out your clothes”
He spent as
long as he could in the shower and was reluctant to leave knowing what awaited
but after fifteen minutes he heard Pamela call out impatiently requesting his
sheepishly into the bedroom clad in his new feminine dressing gown to a chorus
of approval from the two women. Mrs Quinn examined his legs and nodded her approval
saying something about how envious girls would be of his hairless legs. He
noticed various items of female underwear on the bed, a formidable girdle, a
bra, a slip and a pair of stockings.
don’t want to embarrass you Jackie by asking you to remove your dressing gown
so you can slip on these panties before you put on your girdle.” she said as
she handed him a pair of white silk panties. Shamefaced he stooped down and
pulled the soft panties up his legs. He was then given a satin panelled open
bottomed girdle and struggled to pull it over his hips. It stretched from just
below his ribcage to the middle of his thighs he instinctively knew the garment
would have a restricting effect when he walked.
could not have done it better myself” Mrs Quinn congratulated him as she slid
the robe from his shoulders.
“Let me help
you with the zipper, back zips can be a little awkward” Pamela offered and
began zipping him into the constricting underwear.
to take pleasure in her task jerking his body as she pulled the back zipper up
and he had to hold on to the bed post to steady himself as she completed her
girl” she whispered in his ear her groin pressing on his rear end as she
gropedhis satin clad backside while her
mother busied herself elsewhere in the room “you won’t get out of that in a
He was told to sit on the bed and as Pamela
rolled a stocking up his right leg, her mother repeated the process on the left
one and clipped them to the dangling suspenders. Added to the constricting
girdle he now had the sensation of the stockings encasing his legs and the
garters pressing into his thighs. They slipped a pair of three inch heels on
his feet and fastened the straps snugly at the ankles.
the room as Mrs Quinn sat on the bed reassuring him and telling him how
grateful she was for his cooperation. He noticed her take some bottles of
liquid from a small case on the bed.
take a minute” she said calmly as she rubbed a liquid in a wide circular motion
above and below each nipple area.
Pamela returned with a wide smile on her face
holding something in either hand. As she got closer he recognised what they
were and pancaking tried to get up but Mrs Quinn’s strong grip firmly held his
arm preventing him from rising.
and unable to move or speak he could not takehis eyes off the objects Pamela held and gasped as Mrs Quinn took one
large breast form and positioned it firmly over what laughingly passed as his
left pectoral while Pamela performed the same exercise on his right side. They
held the breast forms firmly to his chest for a short while until they were
satisfied his newly acquired bosom was secure and then stood back to admire
the latest in breast form technology Pamela and while obviously not the real
thing they are a great improvement on previous models. The skin tone is almost
perfect and see how seamlessly they attach to his chest” Mrs Quinn said
pointing to the area where the breast forms and his skin met.
very realistic indeed” Pamela enthused as she took him by the hand “come along
Elizabeth have a look at your new boobies.”
Mrs Quinn asked.
character is called Elizabeth”
have chosen something more servile but you’re his mistress I suppose” her
each took one of his arms and led him to the full length mirror. He felt his
chest muscles, puny as they were, being pulled down as the weight of his new
and unfamiliar but very realistic breasts tugged at them with each step he
back Elizabeth” Mrs Quinn instructed as they guided him across the room.
mirror he didn’t want to see his reflection and looked away but Mrs Quinn
after all our work please don’t tell me you are not willing to view the result”
to look she stood behind him and firmly guided his head to face the mirror.
Unable to avoid it any longer he gazed at his reflection and he too had to
focus hard to try and discern the almost seamless join where the breast forms
attached to his chest. She was right the skin tone was nearly a perfect match
and they could reasonably be considered passable. Adding another humiliation
Pamela took the breasts in her hands and after what could only be described as
fondling them said
they’re perfect, just the right weight and shape I’m so jealous”
should be they’re state of the art and cost a fortune, now Elizabeth time to
get you into your bra” Mrs Quinn said handing him a black lace bra.
In a sudden
attack of modesty he desperately felt the need to cover his new breasts and
having taken the bra turned away from them and slipped his arms through the
that sweet, but no need to be shy, after all we’re all girls here ” Mrs Quinn
chirped, “I’ll hook you up this time but as you will have to do this several
times over the weekend you really will need to learn how to do this for
yourself, you can practice with Pamela later.”
She draped a
satin and lace slip over his head and allowed it to fall around his knees and
taking a black dress from the bed repeated the process, Pamela zipped it right
up to the nape of his neck and fixed the white Peter Pan collar and stiff cuffs
to her satisfaction. The skirt of the uniform dress clung tightly to his body
and he knew that together with the long tight girdle his gait would be
restricted to smaller steps. This was confirmed as he minced his wayto the dressing table his heels clicking on
the wooden floor. He was seated on the chair while they got to work on his
make- up, Pamela finished off the process by having him pout while she applied
a subtle shade of lipstick. Ordered to stand they again inspected his
appearanceto satisfy themselves that he
was as feminine as they could possibly fashion him and after they were
convinced he would pass muster he was once again marched to the mirror.
stage the image reflected in the mirror came as little surprise to him but the
triumphant look on the faces of his tormentors served only to increase his
mother he looks adorable” Pamela said unable to contain her pleasure.
“Yes he does
darling, barely any trace of masculinity. Now Elizabeth as you can see you look
like a normal girl in a black dress but you’re not meant to be just a normal
girl in a black dress now are you?” Mrs Quinn asked him.
now look at yourself in the mirror and tell me what your new position is?” she
utterly mortified by the question and while he desperately wanted to point out
that he was merely helping Pamela with her play he was so demoralised by his
new attire not to mention browbeaten and intimidated by this formidable woman.
As he gazed upon his image he lowered his eyes and meekly said
Quinn scolded him “a maid addresses her mistress as Madam”
new maid Madam” Jack repeated in a docile voice, his eyes remaining firmly
lowered in keeping with his new and now self-confirmed status.
“And what does
a maid wear to distinguish herself from her betters.” Mrs Quinn continued the
at Pamela and his heart sank as he saw what she held in her hands.
and cap Madam” he replied not forgetting to use the correct form of address.
clever girl” Mrs Quinn cooed noting his new attitude “you will make an
excellent servant girl now extend your arms”
mortification he did as was instructed and allowed Pamela envelope him in the
symbols of the female domestic servant, a white frilled pinafore apron which
she drew over his arms and tied the strings in a large bow at the back, the
matching cap which she secured to his hair with Bobbi pins.
better” Mrs Quinn announced “isn’t it extraordinary how the addition of two
small items of clothing can transform a girl in a simple black dress into a
suitably attired domestic servant?”
His cheeks burned with shame at the mention of
his new position and trying to hold back the tears he asked meekly
rehearsals are over can I revert to my own clothes Madam?”
Oh I’d almost forgotten about those. What do you think Pamela?”
certainly looks the part but there’s no doubt he will require extensive
training in a maid’s duties and responsibilities before we can even think about
“My thoughts exactly” Mrs Quinn answered “I
have to run some errands so you may as well begin his training immediately.
I’ll get rid of these as you won’t be requiring them for a while.”
sank at her words and watched dejectedly as Mrs Quinn picked up his male
clothing and left the room. Pamela walked slowly over to him and staring him in
the eyes purred
been looking forward to this for a long time.”