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.
This piece is a continuation of my last contribution and could fit into the storyline before Bea's last piece. If enough readers are interested there is scope for this part of the storyline to continue independently of how Bea or Bleinda wish to proceed.
A few days
had passed since his encounter with Rose and he was fearful that she may have
spoken to Miss Savage or some of the pupils about him helping her carry out her
duties while dressed in an apron and cap but there wasn’t a mention by anyone,
much to his relief. It wasn’t something he wished to dwell on but he did enjoy
being in Rose’s company as she was one of the few females in this place he felt
some way comfortable with despite her havinginsisted on him wearing the apron and cap while helping her. There was
no doubt he was embarrassed at first but apart making adjustments here and
there to the garments Rose made no remark apart for expressing her gratitude
for his help and her easy going manner soon made him almost forget his new attire.
This was the
first Saturday that he didn’t have to accompany his mother on one of her
interminable shopping expeditions. As luck would have it his mother and his
current tormentor in chief Miss Savage had left early for some course or other and
thankfully would not be back until late. He had the whole day to himself and
just had to make sure to avoid his other persecutors Pamela and her gang.
Lying in bed
he began thinking about Rose and remembered that for some reason she had left
some of her things in the guest bedroom. Driven by this he went to the guest
bedroom and found the cap she was wore on her previous visit and holding it to
his nose he inhaled her scent and getting aroused he lay on the bed closing his
eyes and holding the cap to his face started to pleasure himself with his other
He shot bolt
upright to find Rose in the doorway gazing down at him with a mixture of shock
horrible little boy, I thought you were different” she spat
Rose I didn’t know you were coming today” he said feebly, hurriedly covering
himself with a sheet and discarding the cap.
I’m not the only one coming today” she sneered “I’m sure your mother would like
to hear about this.”
Rose, not that. Please don’t tell her” he pleaded. “I’ll do anything, just
don’t tell her.”
“Well as the
school hasn’t employed another maid I could do with some help.” she said.
problem, I’ll just go to my room and get dressed” he replied.
be necessary, I have all you need right here” she announced as she patted the sizeable bag on her
shoulder, “As you will be doing the work of a maid it’s only right that you be
He had worn
the apron and cap on the previous occasion so he felt it was a small price to
pay for her silence.
Rose I’ll wear the apron” he said.
you will, and also that cap that you seem so fond of, but a maid can’t just
wear an apron and cap, now can she?”
“What do you
mean?” he answered unsure of where this was going.
well I collected these from the drycleaners, I was going to drop them off in
the maid’s quarters later but I guess we will need them here” she said as she walked
slowly to the bed and put down the bag. Opening it she took out a similar
uniform to the one she was wearing. He felt a queasiness in his stomach.
“I think this should fit you, it’s the one the
previous maid wore it might be a bit tight but we can fix that. ”
expect me to wear that” he gasped.
“Not only do
I expect you to wear it you will also wear suitable underwear. Stay here and
don’t move” she ordered.
She left the
room and he stood rooted to the spot, the sheet covering his naked body, still
in shock from Rose discovering him in such a comprising position, wondering did
he hear her correctly, she wanted him to wear a maid’s uniform and something
about underwear. He was still pondering this when she returned with some items
in her hands.
get started” she said brusquely, laying out what he now saw to be items of
female underwear. She couldn’t be serious he thought there was no way he would
wear female underwear nor a maid’s uniform. He began to come to his senses.
Rose I’m not wearing those” he said trying to sound confident.
here you horrible little excuse for a boy. If you don’t get into these and your
uniform pronto I will go straight to Miss Strang the principle and tell her you
masturbated onto an item of my uniform. I really don’t think she will allow a
pervert to remain in such a prestigious school. It’s quite probable that your
mother will lose her job. They are very strict here, ask the maid that just
lost her job for a minor infraction of the rules”
dumbfounded by her outburst and knew that while that’s not exactly what
happened Miss Strang would probably take Rose’s word over a newcomer like him.
He couldn’t risk his mother’s job, she’d be devastated. Rose looked at him
impassively arms folded.
what’s it to be” she said
Rose” he said “I’ll do what you want.”
so” she crowed and there will be a few rules. First one is you will address me
as Miss Rose as I will be your tutor and you will curtsy when you address me.
Is that clear?”
Rose” he meekly replied, resigned to his fate.
now let’s get you into your new underwear.I wasn’t expecting this so I borrowed some of your mother’s things
there’s not much of a size difference. This girdle will keep that thing between
your legs out of harm’s way. She has good taste just look at these satin panels
front and back.”
horrified. Not only had he to endure the shame of being forced into dressing as
a girl he was being humiliated even further by having to wear his mother’s
underwear. He had no time to dwell on this as Rose took the sheet from him and handed him the
girdle. He tried to hide his now very flaccid penis but to no avail, he quickly
stepped into the girdle as he began to draw it up his legs Rose went behind him
and told him to widen his legs. As he did so she drew his cock back between his
legs and told him to resume pulling up the girdle. When he was finished she
stood back and pulled the high waisted girdle further up his torso until she
was satisfied. She then rubbed her hand between his legs and smiled.
only will your girdle keep your little clitty firmly in check it will also give
you a more feminine lookdown there, not
that anyone will see it I suppose”
him a pair of black pantyhose and instructed him how to carefully put them on.
Then she held out a pink satin bra and told him to put his arms through it and
then she moved behind him to fasten it. She turned him around and adjusted the
straps and place rolled up panties into the cups.
a girl without boobs” she chuckled as he grew redder. “Now hold up your arms”
Doing as he was told she placed a matching pink satin slip over his head and
also adjusted the bra part around his now small jutting boobs. She quickly
brushed his hair into a ponytail like she had done on the previous occasion and
taking the grey uniform dress from the bed slipped it over his head and told
him to placed his arms in the sleeves. As he did so she zipped up the back of
the dress. As she held out the apron he knew what was required of him and
meekly held out his arms as she wrapped it around him tying it in place.
Pointing to a pair of black two inch heels she motioned for him to put them on.
Much to his surprise they fitted him.
just a little something else I think” she said standing back to admire her
handiwork. He was horror struck as she rubbed liquid foundation to his face and
then began applying a pale pink lipstick to his lips.
better, but there’s something missing I wonder what is it? Oh yes your cap” she
said as she held out the article that had got him into this mess in the first
“Now put it
on….. GIRL” she sneered.
took the cap from her and placed it on his head and fixed it into place with
the hair pins attached to it like she had shown him previously.
Now come have a look at yourself” she said as she motioned him to the full
trace of masculinity that he may have previously shown was all but obliterated
for all intents and purposes he now looked like a young servant girl.
your mother would approve, I believe the vast majority of single mothers prefer
to have a daughter rather than a son. I’m sure she would be happy to know you
are wearing her lingerie. Now time to put you to work my girl. Oh by the way I
don’t think Jackie is an appropriatename for a maid, I can’t think of a suitable one at the moment so I will
just call youGirl. Ok with you Girl?”
she asked rhetorically
had no choice regarding this further humiliation he nodded.
you say” she snapped.
Rose I forgot” he apologised making a crude attempt at a curtsy.
let it pass this time. And we’ll have to work on your curtsy.”
Rose” he said almost gratefully.
last time I was here I showed you the duties of a maid and you were quite a
good pupil so let me see what you have remembered. Start with your own room, I
will give you fifteen minutes and then check on your progress. I expect
everything to be spick and span when I make my inspection. Or else there will
be consequences” she ordered as she pointed to his room.
and left and for the first time felt the sensations of the feminine clothes he
was now forced to wear. He wobbled slightly at first in the heels but after a
few steps got the hang of it. He now felt the girdle constrain his stomach and
the odd feeling of his cock tucked between his legs unable to move because of the girdle holding
it firmly in place. The bra straps gently biting into his shoulders and across
his back, the satin slip rubbing against the material of the uniform dress
making a faint rustling sound. He heard the whisper of the pantyhose as his
thighs rubbed together as he walked in the unfamiliar shoes.
his room and again saw his reflection in the mirror. He had to look very hard
to see any semblance of the boy who left this room an hour ago. A somewhat
downcast younguniformed maid stared
back from the mirror. His thoughts were interrupted by a now familiar voice at
the door addressing him by his new name.
admiring yourself and get on with your work.
Rose” he said respectfully and gave a much improved curtsy.
her new charge to get on with her work and thought to herself this could be the
start of a wonderful arrangement.