Date: Thu, 13 Aug 2009 00:28:07 -0700 (PDT)
From: Smith Smithy <smithsmith2332 (at) yahoo (dot) com>
Subject: The Family Next Door - Chapter 2

This story is completely fictitious and involves minors engaging in sexual
activity, transgendered characters, and bondage.  If any of these offend
you or you are not of legal age, please leave immediately.

If, however, you are of age and that all sounds exciting, please read and
enjoy.  I find that not enough people write what I like to read, so I've
devoted some time and put together a little fantasy/romance story for you
all.  I really love to hearing from people about my work, so please e-mail
me with any accolades or criticisms you've got.  Hearing from people who
enjoyed my story is what will keep me writing and constructive criticism
will only make them better quality.  You can reach me at: smithsmith2332
[at] yahoo.com.  Please place the series or chapter title in the subject
line.

This is the second chapter in a series that I plan to continue for some
time.  This time around we explore a bit more into Jessica's past and how
she came about.  Plenty of kinky sex too, of course.  Enjoy!


The Family Next Door

Chapter II - A Not So Lazy Day in Bed

I woke up and was immediately confused as to where I was.  I definitely
wasn't in my own house.  I tried to sit up, and that's when I noticed that
I wasn't alone in the bed and it hit me that what had happened hadn't been
a dream.  Jessica lay there in my arms, breathing lightly as she slept,
still dressed in her boner-inducing lingerie.  I really had been cuffed to
a bed by my next door neighbor and she-formally "he"-had fucked my brains
out.  I guess this is the point where some people would be horribly freaked
out at where their lust had lead them while in the heat of passion.  All I
could think about, however, is how beautiful Jessica was.  That, and how
much I wanted a repeat of the earlier events.  And thinking about that made
me painfully aware of my hard cock nestled between Jessica's thighs.

I carefully rolled to the side and slid my arm out from underneath Jessica.
I felt a bit awkward standing stark naked in the middle of Ms. Swanson's
bedroom.  Especially considering I had just fucked her transgendered
teenage daughter.  A daughter whom Ms. Swanson may not even know about, now
that I thought about it.  My rational mind kept telling me to get out of
there as quick as possible, but reason was immediately drown out of my
brain when I remembered that Jessica had pulled those wrist cuffs out of
the dresser in front of me.  I stepped over to it and quietly slipped open
the top left drawer, the one that Jessica had opened earlier.  Inside sat
more restraints: some more black leather cuffs like Jessica had used on me
as well as some metal pieces, including one that I recognized as a spreader
bar.  There was also a couple sets of full-body harnesses, one of which I
picked up and pressed against my body.  Ms. Swanson was into some serious
bondage, it seemed.

Putting the harness back, I closed the drawer and opened the one below it.
Inside were a bunch of whips and paddles.  Gods, this woman is kinky, I
thought.  Finally, I opened the last drawer on the left side and found
Ms. Swanson's dildo collection, neatly organized by size from shortest to
longest.  I reached in and pulled out a light pink one from the middle, one
that was probably about six inches long and maybe an inch around.  I just
stared at it blankly for a few seconds before I brought it up to my mouth
and began licking it.  Something in me just wanted to suck that fake cock.

"I see you've been exploring my mom's little toy chest," I heard from
behind me in a light voice-even while she wasn't genetically a girl, her
voice still had a feminine quality to it.  I turned around, the dildo's
head still in my mouth without even realizing it.  All I could think of is
how amazing Jessica looked.  She rubbed her hand on the bed, inviting me to
come sit with her.  The dildo still in my hand, I sat down next to her and
she pulled me in close, arms around me.

"Jessica, I've really got to know: how did this all start?  And where does
this go from here?"

She sat thinking for a few moments, deciding if she wanted to give me the
whole story.  "I guess it started about six months ago...  But no, it was
longer than that.  Since I was 11, I've been playing around with girl's
clothes.  I would swipe panties from my mom and my sister from the laundry
basket.  Bras and other clothing too.  Wearing them turned me on, but there
was more to it than that...  I'd wear panties all the time, under my boy
clothes, even to school or anywhere else.  Whenever I had a few hours
alone, I would dress up as a girl completely.  I even tried on some of my
mom's make up.  I enjoyed the sexual thrill I got from it all, but I also
just enjoyed looking and acting like a girl.  This went on for about for a
few years, until about six months ago.  That's when my mom walked in on me.
She obviously suspected something and must have planned to catch me in the
act.  Michelle was at a girlfriend's house and was going to stay overnight
and mom said she was going to go out shopping and she wouldn't be back for
at least three hours.  Three hours wasn't enough time to get dressed up and
become the real me, but three hours was what I had and I was going to take
it.

Instead of going out to the mall like she told me, she actually just
grabbed a cup of coffee before coming back a half-hour later.  I didn't
hear the garage open because she slipped in the back door.  She snuck up
the stairs and watched me in her room as I struggled to zip this little
blue dress she has.  Under it I was wearing my favorite set of her
lingerie, a little black bikini panty with a lacy black bra, garter belt,
and black stockings.  As I was reaching for the zipper, she calmly walked
in and said 'Looks like you could use a hand with that.'  I was nearly
frozen with shock and embarrassment.  Here I was, a perverted little boy
playing in his mother's lingerie pretending to be a girl.  I was sure she
was going to kick me out of the house and disown me or something.  Hehe,
how little I really knew about my mom at that point...  Instead or yelling,
she just zipped up the dress, walked over to the closet, and picked out a
pair of blue high heels.

'These are my favorite shoes to wear with that dress.  They've got a three
inch heel, so you should be able to manage them while you learn.'  I was
still shocked and embarrassed and my emotions were running a mile a minute
as she sat me down and put the shoes on my feet.  I was pretty lucky,
because not only did her clothes fit me great, but my mom and I had the
same shoe size as well.  Anyways, she put the shoes on me and sat down on
the bed next to me.  All she said was 'It's ok, baby, it's alright.  Mommy
loves you so much,' and she kissed me on the cheek.  I leaned in and began
bawling my eyes out right on her chest.  In between sobs, I told her 'I
want to be a girl, mommy.  I want to be your little girl.'

From there, my mom's supported me ever since.  She's bought me clothes of
my own, she redecorated my room, and she's even letting me start on
hormones in a few months, when my doctor okays it.  Eventually I'm going to
have to come out to the world, but hopefully not for a while.  Until then,
I live as I'm really meant to be when I'm in private.

And you want to know where this goes from here?  Well, that all depends on
what we both want.  But I've said enough for now.  We can talk more about
it later."

"None of that explains the cuffs or your mom's 'toy chest' though."

"Like I said, more later.  For now, let's have a little fun with your new
toy here," she said as she picked up the dildo I had grabbed earlier.  She
put up to her mouth and began licking it seductively.  At the same time,
she reached down and started to play with my quickly hardening cock.  A low
moan escaped my mouth.

"Open up," she said.  I did as told and she placed the dildo into my mouth,
still lightly stroking me.  Reaching across me, she grabbed the writ cuffs
again and placed them back on my arms.  "Now, just let me grab something
else from the toy dresser real quickly...  And don't think about letting
that cock fall from your mouth."

She slid over me and rolled off the bed, walking with a sway in her hips
over to the toy dresser.  She pulled two things out of it, from the upper
and middle drawers: a small flogger and the metal spreader bar.  I was her
slave, her little sex toy again, and I loved it.

"Spread your legs, my little slut," she said.  She then took the spreader
bar, attached the ends to my ankles, then raised my legs up and attached
the bar's ankle cuffs to the cuffs on my wrist, leaving me immobile on my
back with my ass exposed in the air.  I watched Jessica as she sucked on
the tip of her middle finger and then began swirling it gently around my
asshole.  I was still slurping on the pink dildo in my mouth and my boner
was pressed up against my abdomen.  Jessica's finger was driving me mad as
she danced around my puckered little hole.  Then she lowered her head to my
ass and her tongue darted against my hole, making me moan like the little
slut I now was.

"That's right slut, moan for me...  Moan for your mistress," she said
before plunging her tongue into my hole.  I remembered how much she had
loved it when my tongue was up her tight ass-pussy last time, and now I
knew why.  She continued to rim me as she reached up and began fucking my
mouth with the dildo.  The joint sensation of being rimmed and mouth fucked
with a toy was sent me over the edge and I came without even touching
myself.

She looked up at me with a wicked smile on her face and said "I didn't give
you permission to cum yet, slut.  Looks like you need a punishment to teach
you a lesson."  Leaving the dildo hanging out my mouth, she reached over
and grabbed the small flogger she had grabbed earlier.  "I'm going to whip
you now, and instead of a set number of hits, I'm just going to hit you
until you get hard again.  And if you let that cock out of your mouth,
you'll really regret it.  Do you understand?"

I was really scared, but I also really wanted to please my mistress, and I
nodded slowly.  She must have seen that fear in my eyes, because she told
me "I love you, hon, but this is for your own good."  She bent over and
planted a little peck on my ass cheek, and with that I relaxed a bit.
Suddenly, the first hit cracked over my cheek.  It stung, but it also made
my cock jump.  More followed, alternating between my ass cheeks, a barrage
of loud cracks as my little transgendered mistress worked my ass over with
a flogger.  And each hit made me moan through the dildo and made my cock a
little bit harder.  I counted twenty swats before she stopped and grabbed
my cock, checking for an erection; I was rock hard by that time.

"Good, you've done exactly as I wanted this time.  Now you get a reward,"
as she slid the dildo from my mouth.  "Nice and lubed, excellent."  She
caressed my bright-red ass cheeks softly with her left and leaned in,
giving my asshole one last tonguing before pressing the head of the dildo
up against me.  I'd only explored playing with my ass a little bit before
this, occasionally putting a finger or two inside me while in the shower.
I'd never had anything as big as that dildo inside of me before.

The dildo hurt as she began to press it forward, but like the flogging, it
was pain mixed with pleasure.  She slid it in slowly, teasing me as I
moaned uncontrollably.

"Good, my little slut likes it in her ass.  We're going to have lots of fun
with this.  So much fun."  She was jacking her cock with her left hand as
she worked the dildo into me with her right.  Finally, the dildo reached
its hilt and I felt stuffed.  She let it sit in me for a few seconds before
she slowly started to withdraw it.  She worked it in and out, slowly
picking up the pace, as my moaning got more and more frantic.  It wasn't
long before she was panting as well, her left hand now playing with her
nipples, pinching and twisting them.

Suddenly she pulled the dildo completely out of my ass, leaving me feeling
empty.  It was short lived, however.

"Oh gods, I need to fuck you!  Right now, you dirty little slut!"

She lined her girl-cock up against my hole, and with one smooth motion,
drove it into me.  It was about the same length as the dildo, but a bit
wider.  I moaned in ecstasy as she mounted me and began to fuck my ass.
She played with my cock as she thrust in and out, the heat from her hard
cock radiating into me.  She only lasted about a minute for before she
began to slow down and tense up.  Finally, she began to cum inside my ass,
moaning loudly as she filled me with her girly juices.  My dick was
throbbing at this point, and she sped up her jacking pace until I blew
another load onto my abdomen.  We both lie there panting as her member
shrunk and slowly slid out of my ass.  She leaned forward, and with one big
lick across my torso, took all of my cum into her mouth.  Rolling to my
side, she kissed me passionately and we snowballed once again.

She pulled away from my face and unlocked my wrists from my ankles.  As I
stretched my now sore arms out above my head, she unlocked the spreader
bar.  I stood off the bed and stretched out my legs as she gathered the
toys we'd used and set them to the side.  Finally, I lay down next to her
and we wrapped each other in our arms, both spent and well fucked.

I glanced over at the clock, which read 3:00 pm.  No worries about my mom,
as she was going out with a few girlfriends after work for a few drinks,
her Friday night tradition.  She wouldn't be back until later that evening.
But Jessica's family...

"Jess, when are your mom and sister going to be back?"  "Oh, don't worry
about that.  Michelle and my mom left this morning to tour a few colleges
out of state.  They won't be back until Sunday afternoon."

"Well, that's good to know, I'd be afraid if they walked in on us...  Hey,
Jessica...  Did you really mean what you said earlier...?  You know, when
you said you loved me?" I asked.

What can I say?  I'm a sappy romantic.

She gave me an amused little smile.  "You know, I just might have.  Would
you agree if I asked to be your secret girlfriend?"

"Absolutely.  So long as 'Mistress Jessica'stays around too," I said,
grinning.

"Oh, you can count on that.  Someone's got to keep you and that beautiful
cock of yours in line."

Jessica got changed into a yellow tank top and a cute little pair of blue
shorts, and we spent the rest of the afternoon cuddled up on the living
room sofa watching a movie.  We blew each other once more before I had to
get home.

That was the start of our relationship and many other good things to come.