Date: Mon, 13 May 2013 17:10:03 -0400
From: John Smith <disposablehero29@gmail.com>
Subject: Wicked Stepsister - Chapter Two TG

            Beyond asking me to pass one of the side dishes to her at meal
time, Renee pretty much ignored me until the weekend. She didn't even say
anything to me when we got off the bus Friday afternoon. It's strange, but
I was really happy to see that her mom's car wasn't parked at the house. I
was under the impression, despite all the evidence to the contrary, that
one of these days I could do everything right and make Renee so happy with
me that she'd finally let me fuck her... make a man out of me and all that. I
was never too bright about some things.

            It was my turn to wash the dishes, but it didn't take very
long. When I went into my bedroom, I saw that the pair of panties had been
laid out on my bed. I never left them out like that, so I knew that Renee
had taken them out of my hiding place and put them there as a message. I
quickly stripped out of my school clothes and pulled the pink underwear up
my legs. It was only me second time putting them on, but they already felt
just as natural as the rest of my clothes.

            I ran down the hallway, but made sure to slow down before I hit
Renee's door. I decided it would probably be a good idea to show respect,
so I knocked and, as politely as I could, asked if I could come in.

            "Enter, slut," Renee responded after a nice long pause.

            I did as I was told and opened the door. Renee was sitting at
her computer and didn't even look up to acknowledge me. She was wearing
what looked like a pair of basketball shorts and a slim fitted t-shirt.

            I stood patiently and waited for her attention. Being a little
nervous, I did find myself picking at the waistband of the panties a couple
of times. Just when I figured she intended to make me stand there the whole
night while she ignored me, she asked me a question.

            "Have you been a good girl, slut?"

            "Yes, Renee," I replied, meekly.

            "You haven't been touching your dick have you?" She asked.

            "No," I answered quickly, then had to correct myself, "Not
jacking off, I mean. I have to touch it when I wash in the shower."

            "That's okay," she explained, "Now come here."


I obediently padded over to Renee. She swiveled around in her chair to face
me. I could see she had been video chatting with someone, but must have
closed the connection.

            "Turn around, slut," she demanded, "I want to get a better look
at what I'm working with."

            I jumped a little when she squeezed my right butt cheek. Just
from the touch of her skin against mine, I could feel my dick started to
stir. There was nothing I could do about it, I just had to hope it wouldn't
upset her.

            "You have a really nice ass," she observed, openly palming and
groping my backside the way I'd seen some of the football players do with
the cheerleaders after pep rallies. "It is so cute and girly," she added,
right before the slap landed.

            I was probably more surprised by how loud it sounded than by
the sting. I was surprised again when I felt her hands playing over my
inner and outer thigh. I was certain she knew she was torturing me, the way
her hands kept creeping higher and higher only to fall away at the last
moment.

            "Did you shave your legs, slut?" she asked.

            "No, Renee," I said, after clearing my throat, "It's a family
thing or something, we don't get a lot of body hair."

            "You're like the perfect slut," she remarked before giving me
ass another slap, this time on the left cheek, "I'm going to buy you some
g-strings. It wont be long before you'll have something up your ass, twenty
four seven."

            When Renee used the words "up your ass", I felt a nervous
flutter in my stomach. It was kind of insane, letting her have so much
power over me. I could have jacked off at school or something and she would
have never known, but I actually liked doing what she told me during our
first session. It was something I'd been curious about, but would have
never attempted on my own. Maybe that is why I was so willing to go along
with her, she'd give me an excuse to find out what really worked for me...or
maybe I was just so desperate to cum that I would have agreed to anything.

            Growing up, I dreaded long family trips or any activity that
meant I couldn't slip away if I needed to. If something got me worked up
and I couldn't get off fast enough, my brain started coming up with all
these weird things to up the ante.

            "In the right clothes, I bet nobody would even guess you used
to be a boy." Renee observed.

            "I don't have any tits," I said, sheepishly over my shoulder.
Renee rewarded me with another bracing slap on the ass. I was tenting the
panties again.

            "Some guys like androgynous girls," she said, "Lets do an
experiment. I want to see what you look like when you're dressed for your
role. Follow me."



            I trailed behind Renee as she made her way to her closet. We
were amazingly close to the same size, as my experience with her panties
had proven. She pulled out tops and mini-skirts and made me hold them up to
my body. She finally settled on what appeared to be a schoolgirl outfit.
Plaid, pleated skirt and all.

            "Go put these on in my bathroom," Renee said, after adding a
pair of stockings and a bra to the jumble of clothes in my arms, "I have to
go get something for you."

            Even though it felt like I was getting further and further away
from being allowed to cum, I was actually excited to see what I would look
like in the new outfit.

            It took me a little effort, but soon enough everything was on
and in place. Looking down at my body, I felt like a completely different
person. I'd left the top buttons open so I could look down my own shirt.
Renee's bra was probably the tightest thing I was wearing. The strong
little black garment was doing the best it could to make my pecs look like
boobs. I found myself kind of obsessing over my chest, pushing what I could
together, or up, to see how it looked in the mirror.

            I wondered what was taking Renee so long. I was really anxious
to see what she thought of the outfit. I actually had my cock, which was
pretty much perpetually half hard or better through the whole fitting
experience, tucked under and my dress hiked up so I could see how it would
look when I saw her coming up behind me in the mirror.

            "You're such a slut," she smiled.

            It turned out she'd been looking through old boxes of her
mother's things to find a wig for me. It was black, so it looked like a
pretty natural fit for my complexion. Even before Renee finished putting
the makeup on me, I was amazed at how completely my boy self had vanished
into my slut self. I looked like a totally different person.

            "Not bad," Renee said, appraising her work, "Lets go see how
good of an actress you are."





            Renee made me bring in a chair from the dining room and set it
next to hers in front of the computer. She had a random video chat program
open, and was ready to hit the connect button.

            "Put your hands in your lap," she directed, "and try to look
cute."

            The first person she connected to was a an olive skinned dude
with really hairy arms who was already masturbating for the camera. Renee
frowned and clicked the "next" button before the guy could peel his hands
away long enough to type a greeting.

            It took about twenty clicks before a guy popped up that Renee
approved of enough to communicate with. He was fairly normal looking,
claimed to be eighteen, and had a nice smile. I waited for instruction as
Renee started typing.

            She told him that I was her cousin and that I was a little
insecure after a breakup. The guy typed back that I didn't have anything to
be insecure about. He typed that I was hot and my ex boyfriend was an idiot.

            I smiled and blew a kiss to the camera. I guess I should have
been offended that he couldn't tell I was a boy, but I didn't really care.
That was more validation than I'd had in my normal life in years. He
started typing flirty things and asking me about music and what kind of
stuff I liked doing. Renee shoved the keyboard over so I could type.

            I told as much truth as I could and made up the rest. I felt a
little weird about manipulating him and lying, but I was really loving the
positive attention. Growing up as a boy, you never really want to hear that
you're pretty, but you I guess you can get used to it in a hurry.

            Eventually he asked me where I lived, if it was anywhere near
him. He was three states away, and kind of bummed that I wasn't planning on
taking a trip anytime soon. He said he had to go, probably looking for
someone close enough to actually hook up with. I waved to the camera and
Renee hit next.

            Over the next half hour, Renee taught me how to be a tease and
how to flirt. Guys liked my pouty face, but they really seemed to enjoy it
when I squeezed my pec tits and licked my lips. It was just benign fun, and
we didn't see another cock until the last guy we connected to.

            He was a handsome blonde with really nice abs. It seemed like
he was just waiting for an excuse, or for permission, to whip it out. The
flirting escalated pretty quick, and he evidently didn't care that we were
on opposite ends of the country. He claimed he was lonely cause he just
broke up with his girl. I typed back asking why, and he responded that she
didn't giving him blowjobs. I typed back that she's crazy, blowjobs are so
much fun. It went pretty quick from there, and for a while he seemed
perfectly content just to stroke his rod for me as we narrated sex acts
back and forth in the chat window. Then he typed out an almost sheepish
sounding: Can I see your ass, baby?

            I looked over at Renee, and she nodded. We stood up and she
adjusted the camera placement a little so it tracked my ass. She guided me
into leaning forward and supporting myself against the chair's back. I kept
my legs together, doing kind of a reverse tuck to try and make sure nothing
gave away the fact I had boy parts. Renee assisted me by flipping the back
of my skirt up. She pulled the seat of the panties in from the sides,
creating like a makeshift g-string and putting my ass completely on display.

            Straining to look back at the screen over my shoulder, I could
see the words our friend had typed: beautiful ass! Tits please?

            Renee had something else in mind. She delivered her strongest
slap yet, actually rocking me forward. I was sure she'd left a handprint
that time. Our friend was really enjoying the show, stroking his big dick
furiously.

            That was when Renee decided to turn up the heat. She leaned in
and covered my lips with hers, thrusting her tongue into my mouth. We
alternated between tongue kissing and spanking. It wasn't long before our
friend managed to type out a feeble "Im gonna cum".

            By the time he finished blowing his lovely load, my ass felt
raw, and I was so hard from making out with Renee that the swat team could
have used my dick as a battering ram. I'd seen guys get off in porn before,
but it was different knowing that it was for me. It made me feel so sexy
and horny. I was all set to blow another kiss to the screen and say goodbye
when Renee grabbed my shoulders and spun me around to face the camera.

            She made sure to lift the front of the skirt up, putting the
way my cock stuck out above the panties on display for our friend. Judging
by the look on his face, and the mad scramble for the disconnect button, he
wasn't a fan.

            I wasn't sure what was going to happen, if she was going to
punish me for getting in to it so much, or if the reveal was the
punishment, but I knew better than to ask. She closed out the program and
kissed me again as she grabbed my shoulders.

            I tried not to smile as she forced me back onto the bed, but to
my surprise, she commanded me to roll over. Once I was face down, she
spanked me again for taking too long. Renee was panting like an animal, and
I wasn't sure what she had planned for me, but I got an idea when I felt
her weight press down on me.

            The girl was urgently grinding against my ass, pretending I was
taking an imaginary cock in or something. The strong rocking motion felt
wonderful, with my own cock trapped between my abdomen and the bed as Renee
humped me as hard as she could.

            It was starting to smell like girl in the room again, even
stronger this time than when she'd been thumbing her clit during the
hairbrush blowjob. I found myself picturing her with a cock of her own,
maybe like the nice one our friend from the chat had. I wondered what it
would feel like to have Renee's dick inside of me.

Finally, between the fantasy and the friction, I started to come. I felt
the warmth spurt out along my abdomen, instantly getting smeared around as
Renee's assault continued. With the sensory overload, and everything that
lead up to it, I came harder than I ever had before. It felt like I was
about to pass out.

A couple minutes later, after thoroughly grinding my softening cock, and a
good bit of my new outfit, into the sticky mess I'd made, Renee must have
come as well. She shrieked and thrashed around before rolling off of me.

"Not bad, Slut." She said, patting me gently on the butt.

It was all I could do to roll over without losing consciousness. I looked
up in time to see Renee get up from the bed and strip. She tossed her top
and sodden shorts onto me and headed toward the shower.

"I want everything clean and the sheets back on my bed before dinner," she
commanded over her shoulder, "But don't start the washing machine until I'm
out of the shower unless you want to wear your uniform to school on
Monday."
           "Yes, Renee," I said, dreamily.