Date: Tue, 7 Feb 2012 02:50:57 -0800 (PST)
From: Smith Smithy <smithsmith2332@yahoo.com>
Subject: Meeting with Mistress (FF/teen CD/TG, BDSM)

This story is a work of fiction and completely made up.  It's also got some
stuff that the more prudish reader might not enjoy, including but not
limited to: crossdressing/transgendered girls, lesbians, BDSM.  If these
things bother you, please immediately direct your browser to videos of cute
kittens.

Additionally, this story is original work by me, so please don't steal it.
It's a sequel to another story of mine, Meeting with Master, so please
check that one out as well.

Finally, I love love love feedback-good, bad, indifferent, it doesn't matter.
smithsmith2332[at]yahoo[dot]com

I've met some awesome people who read these stories, and they're the only
reason I keep writing them.  Thanks, and enjoy.

Meeting with Mistress

Our diapers made a crinkling sound as we writhed together, pressing only
our bodies into each other as our lips battled furiously.  Our arms were
locked behind our backs in leather wrist cuffs.  Coupled with the diapers
we were wearing, there was no way we could do anything more than make out
and dry-hump each other-Mistress didn't want us fucking and spending all
our energy on each other while she was out of the house.  Not that either
of us minded, between the sexy thrill of playing with each other, the
wonderful helplessness of being dressed as babies, and the promise that
Mistress would have something planned for later tonight.

I suppose I should introduce myself-I'm Jessica, bisexual teenage sissy
sub, trans-girl, and lover of all things kinky.  I'm 16, almost seventeen,
and going to be entering my senior year of high school.  I'm out to my mom
and my sister, who are both very supportive and have always encouraged me
to be the girl that I am on the inside.  I'll finish off high school as a
boy with the plan of transitioning during the summer before heading off to
college.

Last time I told you about one of my favorite sessions with my former
master.  I say former because it's hard to keep up a sexual partnership
when one of the parties gets locked away in prison for ten years on tax
evasion.  I missed him for a while, certainly, but I wasn't ever in love
with him nor am I particularly torn up about it now that I'm with my
Mistress.  He dug his own hole and now he has to live with it-besides, he
gave me most of his kinky stuff before he was convicted.  All of the sexy
lingerie and fetish wear he bought for me to wear, all of his toys, most of
the chains and restraints.  He always was generous to me, even if he was
stupid with his money otherwise.

Enough about him though, you're probably more interested in the girl next
to me.  That's my sister, Amy.  She's 19 and back home this summer after
her freshman year at college.  We're not very similar physically: she's
slim with firm C cup breasts, while I'm a bit chubby and make due, for now,
with B cup falsies.  My hair is a dark red, curly and medium length, while
her hair is light red and cut short, pixie style with cute bangs over her
green eyes.  I was jealous of those eyes, my own being dull brown.
Physical differences aside, we did share a few things in common: we were
both bi, and we were both very kinky and submissive.  We also shared a
mistress in our very own loving mother.

Mom had known I was a girl before I did, and she's helped me every step
along the way.  The one secret I had regretfully hidden from her was my
relationship with my master.  She soon learned all about that one day when
she found a box of restraints that I had hidden in the garage.  Kind of a
stupid place for them in hindsight, but I just didn't have the space to
stash them in my bedroom.  We had a long heart-to-heart, and she revealed
her long-kept secret love of BDSM and told me about her time spent as a
sexual slave, first to a senior sorority sister while in college, then
later on to my very own father.  She had been the submissive in those
relationships, but she told me she had since become dominant.  The biggest
surprise of that conversation was when she told me that Becky, the girl
from the next block over and my babysitter from when I was ten until I was
twelve, had been my mom's slave slut from sixteen until she left for
college two years later.  The thought of my mom dominating Becky as a
sexual plaything nearly made me cream my panties right there.

To make a long story short, later that night she ended up dressing me in a
sexy leather teddy and fishnet stockings and proceeded to show me her skill
with some of the restraints and toys I had.  My silk bra felt like
sandpaper against my nipples the next day, and my ass was so sore that it
was hard to sit-though that may actually have been because I still had a
plug locked inside of me thanks to a special belt I had.

My sister became involved with our play only a few weeks later.  She had
gotten a ride home from school with her roommate and had wanted to surprise
us.  As you might guess, the surprise was all hers when she found me,
dressed in nothing but PVC stockings and crotchless panties, tied over a
padded bench in the living room getting fucked by Mistress with one of her
strap-on dildos.  Instead of freaking out, Amy immediately slid her skirt
down, revealing a lacy yellow bikini panty that, shockingly, I realized
belonged to me.  Instead of me wearing my sister's clothes, like most young
crossdressers, my sister had stolen some of mine-and that fact couldn't be
hotter to me!  She didn't stop there, though.  She slid off the panties she
was wearing, walked over to my face, and shoved the underwear into my open
mouth, gagging me with my own stolen panties.  Panties that tasted heavily
like her pussy, I might add.  She then turned to my Mommy Mistress and
asked that it be her turn on the horse next.  Mom just smiled and told her
to run upstairs and put on something fitting for a horny lesbian sub-slut.

That first kinky day with my family was months ago, and things have only
gotten better since.  We converted our formerly unfinished basement into a
full-blown BDSM playroom.  That's where Amy and I were now, on the bed in
the playroom, trying desperately to relieve our horniness, knowing that
Mistress had set things up so we couldn't.

"Oh fuck Jess, the vib in my pussy just kicked up to the next level!" Amy
said.  I answered with only a long moan, as my vibrating butt plug had also
kicked up, about thirty seconds earlier.  The plug was huge, and my
sissy-pussy felt so full.  Couple that with the wireless vibrating control
and I was rock hard in my diaper.  Mom must be almost home, I thought.  And
she's getting us ready for whatever she has planned.  Mistress had stripped
me out of my diaper, removed my plug, and placed me on my back on our
padded bench with my legs in the air, spread eagle and locked.  Amy, on the
other hand, was still diapered with her hands cuffed behind her back, with
the addition of chained nipple clamps that were now swinging back-and-forth
as she fucked my ass with a ten-inch strap-on.  Mistress was getting
herself warmed up by sitting on my face, making me alternate between eating
her pussy and her ass all while calling me filthy names.

"Oh yes, my dirty little girly-boy...  Sissy slut son!  Eat your mommy's
dirty holes, please your mistress like the fuck toy you are!"

Needless to say, I was hard, to the point that it hurt.  Well, that and she
was working my girly-cock with a short riding crop as she brought herself
to her first loud orgasm.

Mistress decided to change things up after that.  I was unlocked, put into
a tight black corset with lacy trim (which I loved, thanks to the figure it
gave a chubby girl like me) and thong panties, gagged, then chained by my
hands to the X-rack on the wall.  Amy had her diaper and vibrator removed
and mistress helped her into a pair of tall, locking ballet-style heels
that would keep her feet painfully flexed.  Mistress then put a pair of
metal cuffs with a soft black-fuzzy lining around Amy's wrists and attached
them to a set of chains hanging from the ceiling, which were then hoisted
up so Amy's already flexed toes were just touching the floor.

Mistress walked around my sister's helpless form, caressing her softly,
whispering how beautiful her slave's sexy body was before finally stopping
at Amy's cute ass.  Kneeling down, mistress spread Amy's cheeks and started
to tongue Amy's hole, softly at first, then more and more insistently.  Amy
was moaning like the slut she was as our mom played with her sensitive ass.
Finally, mistress stood up, and grabbed a good-sized butt plug from the toy
shelf, quickly lubed it, and started to roughly force it into Amy's
asshole.  Amy's moans turned to whimpers until the plug finally slid in to
rest tightly inside her.  The plug was followed by a set of weights hung on
the chain of the nipple clamps.  Between the shoes, the chains on her arms,
the plug, and the weighted clamps, I could only imagine the pain that Amy
was in.  I was more than a little jealous.

Mistress grabbed a leather-bound paddle from the toy shelf and proceeded to
work over Amy's immobile body, starting with her ankles, working up the
thighs, lightly on her breasts, and finally hard on her ass.

"Oh yeah slave, do you like that? Do you like my paddle driving that plug
harder into your ass?"

"Yes mistress, I fucking love it!  Oh fuck, I'm so wet, fuck I need to cum
soon, mistress!" Amy shouted.

"Mmm, my little slut, I can see that," mistress said as she ran her latex
gloved hands over Amy's hairless pussy.  I could see the glistening wetness
on the shiny black surface as mistress brought her hand up to her slave's
mouth and made Amy lick it clean.  Mistress knelt down in front of my sexy
sister, and proceeded to ravager her with her gloved hand.  Two fingers,
then three, four, and finally-with panting and loud moans from Amy-her
whole fist.  I watched in awe as my mom fist fucked my sister to body
wrenching orgasm.

Mistress kept her hand inside of Amy until she stopped shaking and her
breathing began to clam.  With a wet *pop!*, mistress slid her hand out and
began lowering the chains that held Amy's arms, massaging the poor slave's
sore and abused body while helping Amy over to the bed.  Amy was completely
exhausted, covered in a sheen of sweat, but had a look of contentment on
her face.

"You turn now, baby sis," she said as she smiled at me as she settled in to
watch.

Mistress released my hands from the wall and ordered me to remove my ball
gag.

"Wow, that was fucking hot!" I said once my mouth was free.

"Hush, my little sissy slave, and put that tongue to good use," mistress
said as she held out her gloved hand, still covered in my sister's warm
juices.  I licked it clean as her other hand played with my girly-cock as
it jutted out obscenely in my panties.

Grabbing me by my boi-clit, mistress led me over to the hanging chains and
placed cuffs on me just as she had to Amy.  Instead of cute boots, however,
mistress placed my legs in a spreader bar.  Then she pulled my arms behind
me and attached the cuffs to the chains and began to hoist the chains up.

"Oh shit, that hurts mommy, please give me more!" I cried out.  She stopped
pulling on them, leaving me oddly balanced leaning forward with my arms
above my lower back, legs spread wide and with everything on display.

"Mmm, my obscene little daughter has a big, hard clit here between her
legs, doesn't she?  Does she need mommy to make her girly-cock feel good?"

"Uh huh, yes mommy, please make me feel good!"

Mistress squirted some lube into her left hand and began slowly stroking me
up and down while reaching around to play with my nipples through the
corset with her other hand.  She gradually built up speed, making my breath
come quicker and bringing me to the edge before stopping.  She repeated her
edging torture four times, leaving me moaning for release, begging to come
all over her sexy glove.

"No honey, you don't get to cum just yet.  In fact, I'm going to make you
cum without even touching yourself."

Spread more lube on her hand, she began to finger me just like she did Amy:
starting with tow fingers, stretching me out gently before sliding in
another.  I was so excited-and nervous!  I'd never been fisted before, and
while I'd had some big toys in my ass-pussy before, a fist was in a whole
league of its own.  Three fingers, stretching and prodding, making me moan.
Four fingers, teasing me for what was coming next.  Finally, she brought
her thumb down and began to press hard against my ass.  I tried to relax,
but it still hurt as she strained to get her hand inside me.  Finally, with
one last push, her entire hand slipped up inside of me to the wrist.  The
feeling was incredible-gone was the pain, replaced entirely by pleasure as
she fist fucked me.  Slowly at first, building up speed and making my
girly-cock drip uncontrollably.  With her other hand spanking my ass hard,
I was now rocking back hard, trying to get as much of her arm as my teenage
sissy ass could hold as I felt my orgasm building.  Slowly at first, riding
the waves of pleasure coming from my ass, then *bam!*, out of nowhere I was
cumming harder than I had ever cum before.  Four hard jets of cum spurted
right into her waiting gloved hand.  She slowly and gently removed her hand
from my boi-pussy, and Amy came over, still somehow walking in those
amazing shoes, to help me down from the chains and remove the spreader bar.
Finally, mistress grabbed two butt plugs from the toy shelf and smeared my
still warm cum all over them both.

Knowing full well what she intended, we both bent over the bed and
presented our asses.  Both well stretched by this point, the plugs popped
right both of us and where quickly secured by two special belts that held
the plugs in but still left our other equipment open for fun.  We both
kissed mistress deeply, thanking her for everything.

"Now girls, if you really want to thank me, you'll let me watch you fuck.
I want to get off seeing my daughters going at it like the horny sluts you
are."

We happily obliged.