Date: Mon, 1 Nov 2004 15:34:15 -0800 (PST)
From: Sachsa Kyer <sachsa_kyer@yahoo.com>
Subject: Caught and Punished

	My best friend through highschool had gone off to the marines, and
instead of paying for a dorm my first year of college, we decided that I
should stay at his mother's house.  They lived much closer to the city than
my family, and this was not very awkward, since I'd been to their house
many times in the past few years.
	I'd always considered Debbie to be very attractive and enjoyed
watching her long legs meet the undersides of skirts most college girls
would consider too revealing.  Older and wiser, she enjoyed all things
feminine, and for this I'd gravitated to her immediately.
	As early as I can remember, there has never been anything quite
like spreading open the edges of a pair of silky panties with trembling
hands and slipping inside them.  Before I'd ever even begun to masturbate,
I knew the pleasures that came with a pair of stolen hose and garter-belt
and had carefully gathered a small collection over the years from clueless
girlfriends and unguarded drawers.  In highschool I'd let my hair grow long
past my shoulders, keeping it soft and curly for the imagined fingers of
men who paraded my fantasies at night, holding me down with the heat and
force no sextoy could ever deliver.
	So when Debbie was at work, what more natural thing than for me to
slip into her room and sidle over to her dresser?  A velvet black bra
dangling carelessly from a drawer made my cock twitch as though it had been
licked; what wondeful taste this woman had!  When I opened it I was
rewarded with exactly what I'd come for: hose piled onto the silky mounds
of thongs and panties with a few black and purple slips tossed to the side.
I ran them over my fingers, held them to my nose to breathe in the
heaviness of perfume and the natural scent of femininity.  My now-aching
cock was straining against my jeans for me to put some on, so I grabbed a
handful, went to her bathroom, and closed the door.
	First, I held up a pair of black french-cut panties with scalloped
edges and eagerly put my legs through them, relishing the light feel of
silk on skin as they slid up my legs to my cock.  I slipped on some
thigh-high hose next and then a garter belt.  My breath was coming in gasps
as I snapped the hooks into the fabric of the hose.  The transformation
from male to female is always smooth, as my body is very trim and slender,
and the change is dizzyingly pleasurable.  I couldn't wait to look myself
over in the mirror, and I hooked the last of the soft velvet bra's hooks
into place, its two cups clinging to my skin like mouths.  Debbie's breasts
were not large, but as the french say: "Anything more than a wineglass
. . ."
	The image in the mirror made me ooze drops of precum into the black
panties, and I lowered them with no choice but to begin caressing myself.
Nothing primes the nerves of a feminine boy's cock like the look and feel
of lingerie, and once they are on his body, orgasm is never far.  I moaned
as the slightest touch of my hand wracked even my spine with lust.  It was
not long before my cock was jetting pearl-white streams down the toilet as
I alternately massaged my ass and nipples with my left hand through the
windows of silk and velvet.  Stripping the undergarments reluctantly, I
cleaned up and replaced them all as accurately as I could.  Lying in bed
that night, I could tell that staying with Debbie was going to be quite
enjoyable, and I silently promised not to leave without some souvenirs.
	She did not seem to notice anything out of the ordinary for the
next few weeks, and I began making my visits to her bedroom drawers a
regular part of the day, as it was I who nearly always got home first.  It
was here that I made my mistake, allowing myself to become lax in the
rearrangment of her gorgeous underthings, but instead of confronting me,
she did something sly.
	Sharing a house means sharing the washer and dryer, and a pile of
her clothes was nearly always laying around, stockings and thongs begging
to be taken to a closet and massaged over a raging-hard member.  I have
never done this, however, because I consider it to be a classic mistake
amongst transvestites.  The laundry is a circuit wherein clothes move.
That means the owner is more conscious about the location of these things,
as opposed to the bedroom, where a woman considers her silky panties to be
safe, putting them out of mind.  I have always prided myself on resisting
my urges in the laundry-room, but she had gone out of her way . . .  There
lay, very conspicuously, a pair of exquisitely made panties.  The skimpy
edges were trimmed in frills and pink lace, as close to a G-string as they
could get with just partial covering for her tight ass.  I did not think or
care about their loss being noticed.  I went to my room and immediately put
them on, savoring every feel of their smoothness.  I did not want to simply
masturbate and replace them.  I didn't want to ever give them back.  So I
put my jeans back on and walked back out to finish my laundry, reasurring
myself that she had so many pairs she would never notice.  Right.
	She said nothing of my theft all afternoon but was quiet during
supper, and I began to think for the first time that someone had caught me.
She asked me how my classes went, whether I'd spoken with any girls.  I
told her that no, the girls in my class bored me.  She seemed to consider
this, barely touching her food.  I decided, rather cowarldly, to end this
awkward scene by taking my dishes to the sink and rinsing them off.  That's
when I felt her hands slip around my waist and the painted tips of her long
nails plunge below my waistline to find the edge of her missing underwear.
	"I thought you'd been doing this . . ." she whispered into my ear.
What could I say?  I only stammered meekly.
	"I think I've got some other things in my bedroom that we could
have some fun with.  Do you think you can do that for me?  After all, those
panties you're wearing are mine", and with that, she snapped them back
lightly against my skin.  She began to strut back towards the bedroom in
one of her short skirts, not bothering to see if I'd follow.  She knew that
from here on I'd be pathetically easy to control, and that I'd have no
choice but to do anything she asked me for the sake of my own throbbing
cock.
	When I entered her bedroom she'd already laid out a slutty-looking
outfit with thong, garter-belt and hose with matching bra, and some
three-inch heels.  Her makeup dresser was opened to reveal its rows of
cosmetics.
	"Don't just stand there, Mark.  Put it on."
	I have been nude before in front of others (I model parttime for
art classes at my college), but never did I feel as naked as I did when I
stripped before this older, commanding woman.  Even in my embarassing
situation, however, the sight of such a slutty outfit made my cock begin to
tingle and my breathing slighly faster.  I began with the black thong and
removed it from the bed, Debbie walking behind me to watch.  The feel of
its skinny string was indescribably rich, at once invasive yet sexy.
	"Slide it up further into your little crack" she commanded.
	I did as she bid and felt my cock begin to stir.  She gripped one
of my asscheeks and whispered: "Now hurry up with the hose and belt."
	I needed no second bidding, and in the course of sliding the hose
up past my knees I could feel my member rising with pleasure.  After I'd
snapped the last hook of the belt and picked up the bra, it had achieved
full erection and was now standing out from beside my thong.  She helped
clasp the last of the bra's hooks and whispered:
 "Turn around so I can look have a look at my little whore."  I turned
slowly and let her eyes go down the length of my body.
	"My, my, it looks like Mark really loves being turned into a girl.
Well, then, you certainly won't mind stepping over here to this stool,
then, will you?"  I shook my head.  For the next fifteen minutes she
applied mascara and eyeliner, lipstick, and some slight blush to my soft
features, effectively feminizing them to their fullest.  Then, she motioned
toward the bathroom.
	She purred: "You look so pretty in that whore's outfit."  I moaned
softly as she squeezed the very tip of my penis in her soft hand, leaving a
sticky spot of precum. My craving for release was becoming unbearable in
the sexiness of her lingerie covering my body, perfumed fabrics awakening
wild desires in me.  I'd already shaved my legs earlier that day, a habit
I'd taken up since moving out.  The hose felt incredible against my smooth
skin,
	 Grabbing my hips, she thrust her tongue into my mouth.  Kissing
those full red lips while dressed like a horny slut had me aflame, my
member brushing against her leg, wild with sensitive nerve-endings begging
to be touched.  She removed her blouse to reveal a pair of petite breasts
with large nipples.  She guided my mouth to them and moaned softly as I
sucked as much of the soft white flesh as I could.  I teased her nipples
with my teeth and felt her grip the back of my head tightly in reponse.
The more of it I gathered into my mouth and sucked, the faster her hands
ran up and down my back as she guided us gently towards the bed.  She lay
down first and spread her legs, hiking up her skirt to reveal her hairless
pussy.
	"Eat me out, you little slut," she ordered.  I began kissing the
inside of her thighs and working my way up to her dripping cunt until I was
barely grazing her outer lips.  I ran my tongue lightly over her engorged
clitoris, savoring the taste of her juices as she grabbed handfuls of my
hair in delight.  She wanted to waste no more time and ground my head in
hard so that I was tonguing her pussy in and out, occasionally circling her
clit slowly.
	"Faster, whore!" she shouted, fucking my face harder with each
forward thrust of her hips.  I took her clit in my mouth and sucked on it,
meanwhile continuing in circles around it with my tongue.  This drove her
wild, and she began to moan and yell, her orgasm fast approaching.  I could
feel her juices all over my face and chin; I had never felt a pussy that
was as soaking wet as hers.  Suddenly her whole body tightened up, and she
let out a long scream as her orgasm wracked her in spasms:
	"Oh yeah, eat that pussy, you little bitch!  Eat my cunt!" she
moaned, pulling my hair and digging her fingers into the back of my head.
Her climax ebbed through her in visible waves; I could feel each one
through rapid tensing of her thigh muscles, gradually diminishing until she
lay back, panting and smiling with satisfaction.
	"That was good, you little slut.  Would you enjoy the same?"  My
cock twitched at this, and I nodded eagerly.
	She motioned for me to lie down, and began caressing the area
between my balls and my ass faintly.  I had never been touched that way
before and let out a long moan.
	"Do you like that, sweetie?" she asked, and with that she slowly
licked from behind my balls, taking each in her mouth, up to the base of my
shaft.  I'd been given sloppy blowjobs by inexperienced girls before, and
nothing had ever come close to this.  She licked higher and higher up my
shaft, never touching the head, sometimes sucking softly on my balls and
then down behind them.  I was in ecstasy.  I never knew such pleasure could
be gotten without even touching the head, which was now leaking sticky
drops of precum into her waiting mouth.  I thought I would die if she
didn't take the head in her mouth, but she made me beg before she would
give me such satisfaction.
	"You want me to take it all the way in my mouth, whore?  You think
what you want matters?  You'll do whatever I say, and you won't ask
questions."  I could only nod agreement.  I would've done whatever she
asked; my aching cock seemed about to erupt at any moment.  I watched her
red lips open into an 'O' as she lowered them down onto the very tip and
slid them down further, so that half of my 7" were in her mouth.  I moaned
and writhed as her tongue flicked across the underside of the head, her
hand still caressing behind my balls and going up and down the shaft.  This
continued for some time before she suddenly plunged the entire length into
her mouth, making me yell in ecstasy.  Suddenly she stopped.  I immediately
began to plead with her to let me finish, but she silenced me with a slap
across the face.
	"Don't try to tell me how to give pleasure to my whore!"  she
commanded, and I lay still.  She then ordered me to get on my hands and
knees.
	"Now slide that thong down." I slid them down to my pantyhose-clad
knees and knelt there with my ass in the air.  Debbie licked her finger and
cupped my now-delicate balls.  She squeezed my cock and then traced a path
down, past my balls, to my asshole, and I gasped in surprise and pleasure.
She began to rub slowly around my tight hole, lubricating it thoroughly
before she pressed gently on the outside.  When she felt it give slightly
she pressed inward until her finger had gone inside.  I felt my sphincter
spasming around its slight width, adjusting quickly until she felt me
completely relax.  Then she squirted some astroglide from the bedside table
onto her two fingers and slid them both inside.  I couldn't have ever
imagined that getting fingered would have felt so good.  To have someone
else teasing your hole is an experiece that, gay or straight, every boy
should have.  She worked them in and out as I moaned, and then curved them
downwards towards my prostate.  I whimpered very loudly at this, and begged
her to do it harder.
	"Is that what my dirty little girl wants?"  she crooned.  I begged
her to finger me harder, that I was her bitch and wanted her to fuck me.
Suddenly she withdrew her fingers and went to the closet.  I could only
gasp and wait painstakingly for the sensations on my extremely sensitive
ass to resume.  I didn't care anymore about dignity or masculinity or my
initial embarassment.  Someone had discovered my feminine side and enslaved
it, and all I wanted right now was to get fucked hard, to be owned.
	"Alright, you little bitch," she said, "I'm gonna fuck you, and I'm
not going to stop until I've cum."  I turned my head to see that she had
donned a big, realistic strap-on with a raised nub for massaging her clit.
She spread my cheeks roughly and put the head of the dildo to my hole.
Pressing inwards and then backing off, she gradually loosened me further
until the head of the slippery strap-on was inside me.
	"Ohhhh, yeah" she moaned, as the pressure on her clit increased,
"Seeing your tight little cunt all stretched open is getting me all wet."
With that she slid it all the way in, giving me goosebumps of pleasure
mixed with pain.  I gasped and moaned as she waited for me to grow
accustomed to the huge cock in my ass.  I'd never had anything that big
before, and the feeling of fullness I got was indescribably good.  I begged
her again to fuck me.  This time she held nothing back and proceeded to
ream my slutty cunt until her hips were slapping against mine.  I screamed
louder and louder, the rapture of getting fucked like a whore making me
ride that dildo hard; I backed up to her until we had fallen into a
frenzied rhythm.  She withdrew partially and re-angled her cock so that it
was pointing towards my prostate and continued pumping into me.  The
pleasure I received from this made me see stars, and I felt a pressure
building in my balls.  I knew it wouldn't be long before I'd cum from such
a hard fucking.
	"Fuck my cunt!  Fuck my cunt with that big dick!" I screamed, drunk
on the waves of pleasure rocking my body.  I felt my cock twitch with the
first wave of my orgasm, and I began bucking backwards against Debbie's
pounding hips, causing her to moan.  Spurts of my cum began streaming out
as I gasped and screamed for more.  It seemed that I kept cumming and
cumming until finally the hot jets subsided and Debbie ground her strap-on
into my ass for a few more minutes until she began screaming also.  Her
climax brought her hips to mine as she clasped my hips and ass, pulling me
onto her cunt as her back spasmed and wracked: "Ride that cock, you fucking
slut!" she shouted as I moaned and let her take me.  When she had finished,
she slowly drew out and went into the bathroom.  I lay on the bed on my own
cum-drenched thong, a warmth and satisfaction coursing through me that no
sexual act had ever yielded to me.
	When Debbie returned, she was smiling through the sheen of
freshly-applied lipstick and had put on the black velvet bra I'd first seen
in her bedroom.
	"How did you like getting fucked like a girl?" she asked.  I told
her that it was incredible, and that I'd never experienced anything like
it.  She looked very pleased, and kissed me.
	"I'm glad you like it as much as I do.  It's gotten lonely in this
bedroom since my husband died, and I've had no lovers since with such an
open mind."  I let her run her fingers through my hair for a while before
she sat up and traced a finger down my cheek.
	"Sit up and put this on while I brush your hair." she said, holding
out a pink slip.  That night we slept soundly together and awakened the
next Saturday morning with the entire day ahead of us to screw and buy new
lingerie.


Email me if you liked my story. Tell me which parts you liked, and I want
to hear your ideas or stories about transgenderism.  Sachsa_Kyer@yahoo.com