Obviously, lipstick was next. And eye make-up. A week later he was jerking off
into some really filthy panties, brown-stained cum from someone's asshole, not
mine, when his Mistress stroked some light cosmetics on him. Not much, just a
touch of mascara and a little eye-liner, some shadow on his lids, and a mauve
lipstick. I told him his face needed more drama, a more lively expression.
Of course he'd forgotten it was there by the time he returned to the bank. He
was still wearing it, I saw, when he arrived home that evening and opened his
Wall Street Journal to wait for dinner. That created a problem. Should I tell
him? If so, how? Should I ignore it? If so, what would he think when he was
getting ready for bed and stared into the bathroom mirror, and saw those stark
eyes and that fashionably dark brown mouth? What had people thought at the bank,
those who had seen him? Add in his perfume and they'd be sure that he was a
transsexual or faggot coming out of the closet. Not untrue.
I decided as usual to say nothing, in order to build his confidence that his
increasingly feminine appearance was neither feminine nor noticeable. I
commented only that he looked especially bright-eyed and alert, and asked if he
been working out, or had gotten a raise at the bank, or what? He was bewildered
but pleased. He knew what had really impressed me, and now he felt encouraged to
keep it up on his own.
As he did. The following day was especially busy for me if boring, just straight
fucks one after another. I arrived home tired -- after all, Loretta, how many
times a day can a woman ride how many cocks to orgasm? Or douche and then get
filled up yet again with more cum? But there was Jim, wearing fresh make-up!
Wonderful! He'd actually bought it on his own, actually found the courage! And
put it on, presentably enough. And worn it all day at the bank, so far as I knew
in a sort of reversal of "The Emperor's New Clothes," thinking that it made him
look better and yet remained invisible! I commented again on how alert he looked
these days, and again he looked pleased. And this time he re-applied it before
coming to bed. Does he do that at work, I wondered? Take out a compact and
mascara and a tube of lipstick and freshen his face at his desk?
The next weeks were routine. Jim knelt naked except for his undies three times
each week, smelling wonderfully feminine and looking prettily made up, trembling,
sucking on my fingers and then receiving from my hand another pair of panties
streaked with who-knows-what, the sacrament of his devotion. He'd kiss them and
slip them on, then stroke cum into them if he could, attach a new brassiere
around nipples he said had become quite sensitive, and after re-applying his
make-up he'd leave with his old undies in a "Victoria's Secret" or "Frederick's
of Hollywood" bag, once in a "Lady Madonna" bag my receptionist provided for the
secretaries at his bank to marvel at.
A few months more and he was mine. If he hesitated to do my most trivial
bidding I spoke to him harshly, and he was crushed. When I praised him, it was
always for some utterly feminine trait or gesture. He blossomed and beamed
whenever this happened, and tried even harder to please me. His breasts were
budding, and I gave him strict orders to play with his nipples for at least
fifteen minutes every day. This gave him so much pleasure, I saw at home, that
sometimes he caressed himself unthinkingly -- if we were at a restaurant or
otherwise in public I had to caution him not to. Gradually I weaned him away from
soiled to fresh panties -- though I still had him cum each session into a
sanitary napkin and then wear it for the rest of the day. He produced very
little fluid, unless I said something to excite him, like praise for the way he'd
plucked his eyebrows, or comment on his two-toned lipstick and lipliner. At home
even the thought of sex ceased.
His accumulating bras and panties finally overwhelmed his bedroom bureau. I
remarked one day that since he seemed to prefer them and they looked so nice, he
should pack away his men's things to make more room for them. He did. The next
day his Mistress scornfully informed him that since he was a woman, not a man, he
should wear full lingerie all the time, not just bras and panties. A woman could
not feel altogether neat and sweet and pretty and respectable unless she was
wearing hosiery, pantyhose, teddies, slips, and now and then even a panty girdle.
That he should begin thinking about shoes and outer garments too. He was old
enough to be wearing heels, and to appear at least now and then in a dress! At
home Jim asked me what I thought, and as always I answered without looking up, as
if the issue were trivial, "Of course wear slips -- your dresses will hang better
when you get around to wearing them. I don't know why you don't. And there are
tailored suits for women as nice as those made for men. Skirts are much more
lady-like. Of course if you wear a skirt to work you'll have to style your hair
differently." So it was two against one. Jim began wearing full regalia under
his business suits, and began to think about wearing a business suit with a
skirt. He played with his hair, trying to make it curve coyly over his ears. My
perfumed fairy princess was developing nicely.
