Date: Sun, 17 Nov 2013 22:37:39 -0500
From: John Smith <disposablehero29@gmail.com>
Subject: Wicked Stepsister - Chapter Three TG

            In typical fashion, Renee pretty much ignored me for the rest
of the weekend. As much as I would have liked to keep my entire new outfit
in my room, Renee didn't want to risk her mom finding it in the closet. I
was allowed to keep the little black bra and wig, but they had to be hidden
away under the mattress whenever I wasn't home. Mrs. Hamlin had made it
very clear that making my bed would be my responsibility and not hers.
Renee did give me a little black slip to add to my collection on Sunday,
but that was about the extent of our contact.

            Since she had been chilly to me between sessions, I was kind of
surprised when Renee came up to me at lunch on Monday. She was smiling,
practically bouncing. She pulled me off to the side, away from the kids I
ate lunch, with which were close to being my friends but not quite.

            I asked what was up and she shushed me, before leading me to
the bathroom by my wrist. Renee checked to see if the coast was clear,
going in by herself first. There was someone else inside, so we ended up
heading towards the next closet one, which turned out to be completely
empty. Renee pushed me through the door and locked it behind us.

            I wanted to ask what was going on, but was worried it was an
impromptu session, and a question like that would probably make my life
really tough for the rest of our lunch break. Thankfully, she didn't keep
me in suspense for too long.

            "I got something for you," she beamed, pulling something out of
her backpack.

            It was a pair of lacy red thong underwear. She twirled them
around her index finger for a moment.

            "Where did you buy those?" I asked.

            "I didn't buy them, slut," Renee corrected, "We're borrowing
these from Janet's older sister. Little J owed me big, so I had her swipe
these for you."

            "She knows they're for me?" I asked, knowing that Janet, aka
Little J, was probably the biggest gossip in the whole school.

            "No, dummy," Renee scolded me, "She thinks they're for me. I
told her I wanted to try some out before I bought any. Of course, they're
more your style than mine." She smiled, "Go ahead, try them on. Little J's
sister is just about my same exact size, so they should fit you perfectly."

            I slung my backpack off my shoulders, since I figured it would
make taking my pants off and keeping my balance a bit less complicated.
Renee set it on the counter by the sink. Next, I unzipped my jeans and made
sure not to drag them on the bathroom floor any more than I had to. When I
took my boxers off, Renee snatched them with her free hand and announced,
"Confiscated," before handing me the red thong.

            As always, Renee was right. They fit perfectly. I couldn't help
swishing my hips in front of the mirror a bit to check out how my ass
looked. I felt so sexy, and just couldn't wait to get home and put the rest
of my outfit on. Actually, I kind of hoped we would just have a session
right there, since I was already kind of dressed for it.

            Renee had other plans though. She just gave me a quick slap on
the ass and told me to be on my best behavior. Then she shoved my boxers
down into the bottom of her backpack, unlocked the door, and left. I rushed
to get my pants back on, and just finished with my shoes when the door
swung inward and a pair of very surprised girls walked in on me. Even
though disaster was averted by mere seconds, I was still standing in a
girl's bathroom and had to make a quick exit, apologizing with a feeble
excuse that the boys room was full and I had to go really bad.

            I liked the way I felt in the new underwear, but they were a
lot less substantial than even my pair of panties, so every sensation down
there felt magnified. All of a sudden, I was so turned on I really wished I
was brave enough to just sneak away and jack off. But Renee had been so
kind, giving me a new present, that I didn't want to break my word to her.

            I don't think it hit me, that my next class was physical
education, and that it was a dress out day, until I had already walked into
the gym. All of a sudden, I was standing in the locker room, with a lacy
red thong on under my jeans. As exciting as it was, I felt more than a
little scared. Teasing I could handle, I guess, but some of the guys in my
class were really vocal regarding how they felt about queers. I was pretty
sure wearing lacy girl's underwear would qualify me in their book.

            They were already giving me a hard time just for fumbling with
the combination to my locker. I made as big of a show out of it as I could,
even kicking and pounding on the locker in my fake efforts to get it open.
I knew I couldn't stall forever. If I wasn't dressed out and present by the
end of roll call, I'd have to take a zero in the class for the day.

            After what seemed like forever, the locker room finally cleared
out. I wasted no time popping my locker open and laying out my gym clothes.
Trying to make up for the lost time, I snatched my shirt off over my head
and kicked out of my shoes. I'd just slithered free of my jeans when I
heard the locker room door slamming shut. Someone had opened it while I was
dressing.

            Fearing the absolute worst, I spun around to see who'd walked
in on me. Thankfully, it wasn't one of the overbearing jocks, but instead a
guy named Alex who was usually pretty nice to me. He was a year older, but
his old school district had some different classes, so he ended up a year
behind when he transferred. I was so relieved it was him and not one of the
aggressive slabs of beef I shared the class with that I actually smiled at
him.

            Which was when I remembered I was wearing a pair of lacy red
thong underwear. My hands flew to cover myself up, and I ended up back
pedaling into my locker, making a lot of noise, tripping over my shoes, and
knocking my gym shorts onto the ground. When I bent to pick them up, I
noticed Alex watching me. More specifically, he was staring at my barely
covered backside.

            "It's not what you think," I blurted out as I snatched up my
gym shorts and turned around, "You know I'm living with that girl's family?
We, uh, made a bet." I was trying to find something that made sense in a
hurry, "Yeah, I was trying to get out of doing the dishes for two weeks,
and I lost." I looked down, "Big time."

            "Damn," Alex said after a long pause. He added, "You should be
careful. We're doing the rope climb today, so..."

            I knew what he was getting at. Our gym shorts were notorious
for having loose leg holes. During our gymnastics course, loose gym short
leg holes had been responsible for me getting my first glimpse of what a
girl my age looked like down there. Of course, it had been Fawn the Fatty,
so I wasn't that impressed.

            "Oh man," I said, sitting down on the bench, which was
surprisingly cool on my mostly exposed ass, "I'm dead."

            "Maybe," Alex said, "maybe not. I don't have to do the climb."

            I was about to ask why not, like an idiot. Alex was still
recovering from a torn rotator cuff. Even our drill sergeant of a gym
teacher wouldn't force him up the rope.

            "So, how does that help me?" I asked.

            "Those panties must be cutting off your circulation or
something," Alex said, "I mean I can loan you my boxers."

            I wanted to say, "What am I, some sort of collector of other
people's underwear?" but I thought better of it. He was trying to help me,
after all.

            "Besides," he added, "it would probably be less embarrassing
for them to see me going commando under the gym shorts that to see what
you're wearing."

            "Alright, I'll take them." I said. For some reason, the thought
of just taking them off and going commando myself didn't occur to me until
the bus ride home.

            "Not so fast," Alex said, "I need something from you in return."

            I found myself thinking I was about to have my first experience
with an actual boy, first feeling uneasy and then strangely excited. Of
course, that wasn't what Alex had in mind, at all.

            "English class is terrible," he said, "I've had to do most of
this stuff before, and I can just use my old papers. You'd really help me
out if you did the paper on Othello for me, though. I've read enough
Shakespeare for a lifetime."

            I could hear the coach blow the first whistle. That was to get
everyone to assemble on the court for roll call. I was running out of time.

            "Sure, I'll do your paper. No problem." I said.

            "Then these are yours," Alex said, nonchalantly removing his
boxers.

            He had basically my opposite complexion, being kind of pale and
blonde, but he was really fit under his clothes and his dick was actually
bigger than I expected. He had his pubes trimmed to show it off, and it was
nice and thick looking. I found myself reminded of the guy Renee and I were
vid-chatting with, and wondering how big Alex's cock got when he was
excited and what type of face he made when he came. Of course, in the back
of my mind, I knew there was something I should have been concentrating on,
other than Alex's crotch.

            The pair of boxers hit me straight in the face. Alex was less
concerned than he was amused, tossing off a casual, "Nice catch," as he
busied himself with getting his gym clothes on.

            I quickly changed into first Alex's boxers and then my gym
shorts. I put the panties in the bottom of my bag and stuffed everything
into my locker. We ended up dressed at about the same time and jogging to
be in line before the final whistle.

            Thanks to the alphabet, I was one of the first five to go up
the rope. I was light and took a couple of years of gymnastics before my
family moved to the new house, so it wasn't really difficult for me at all.
Of course, once I slapped the flag at the top, I had to make my trip back
down. There is probably some method that involves less rope friction on the
dick, but I didn't know about it.

            After receiving my check mark on the coach's clipboard, I had
to walk very carefully over to the bleachers. All I wanted to do was get
sat down and find some pose that would cover up my arousal. I sat down next
to Alex.

            "You were the fastest one so far," he said, clearly impressed,
"I don't think anybody is going to beat that time."

            "Thanks," I said, not really used to getting praised in gym
class, by anyone.

            "Of course, it would have been a better show if you still had
your panties on," Alex joked.

            "They're not mine," I protested, taking a quick look around to
see if anyone was listening in on us.

            "I know, I know," Alex said, waving my concern off, "They
should be though. I was so surprised when I went into the locker room. You
totally look like a girl from behind. Well, mainly your ass I mean. I mean
you look good, I mean, for a guy. I mean,"

            "Please stop saying `I mean'," I whispered, "This is
embarrassing enough without having to talk about it. Just promise me you
wont tell anyone, okay?"

            "I promise," Alex said, sincerely, "As long as you don't tell
anyone I said you looked good in them."

            "Deal," I replied.

            "I feel kind of bad about making you have to write both our
essays," Alex said, "Maybe I could bring you a pizza and hang out," he
quickly added, "If it wouldn't distract you too much, and if it would be
cool with the people you're staying with."

            It probably wouldn't be cool with Renee, but I had already
answered before my brain could properly kick in, "Sure, sounds good to me.
I'll ask tonight and give you a call."

            "Cool," Alex said.



            Mrs. Hamlin was fine with Alex coming over. Renee said she
didn't mind either, but I wasn't so sure. Alex showed up with the pizza
about an hour after I called to tell him it was fine. I introduced him to
both Mrs. Hamlin and Renee. Alex politely shook hands with both of them.

            The papers were coming along great, even with the pizza. I
wrote one entire paper first. I had knack for understanding things I'd
read. Sometimes I understood them so well that the teachers got upset with
me. I'd do my presentation about the story we read, nail the meaning, and
then the teacher would twiddle his thumbs for the rest of the class since
I'd wrapped the unit up. Once I had the template, the second one was easy
to make. I just had to come up with different words to say the same things.
I even decided to shake it up in a couple of places to throw the teacher
off.

            Alex read both papers, maybe out of a sense of duty or
obligation. I let him pick which one we'd put his name on and then we sent
the job to the wireless printer. Our teacher always insisted on hand
written rough drafts, so I told Alex he'd just have to copy the second
paper over in his own handwriting after I had them typed up.

            With the academic portion of the evening coming to a close, we
were just about to settle into the general hanging out phase when the phone
in the kitchen rang. Apparently, there was an emergency at the store and
Mrs. Hamlin had to leave. Naturally, Renee was left in charge.

            Almost too predictably, Renee called me out of my room just a
couple minutes after her mom's car pulled out of the drive way.

            "I want you in my room in five minutes, slut. Dressed in your
pink panties and ready to do whatever I say," Renee ordered.

            "But they're between the mattresses. I can't get them with him
in there,"

            "You better figure out a way," Renee advised, "And you won't be
changing in my room. You come to my door dressed. You have less than five
minutes now, slut. If you don't make it in time, your little friend gets to
be the first one to see the photo."

            She turned and walked down the hall, leaving me with a big
problem.

            I could probably have just asked Alex to leave. I could have
lied and made some logical sounding reason up, but I didn't want to offend
him. I liked hanging out with him. That meant I needed a way to get him out
of the room.

            I made several nervous attempts, constantly flicking my eyes
back to the wall clock as my tiny window of opportunity inched shut second
by second. Finally, when I was just about to confess what was going on,
Alex asked if he could use the restroom.

            Not believing my luck, I pointed him in the right direction. As
he was heading out of my room, I added that I had to help Renee with some
chores. As soon as I was alone, I stripped in record time and fished around
between the mattresses for my panties.

            Carrying my shorts and shirt in my teeth, I actually stepped
through the door naked and worked to pull the panties up as I was going
down the hall. I was properly panty clad before I knocked on Renee's door,
with about thirty seconds to spare if my internal count was right.

            No answer. Seconds kept ticking. I knocked again, a little
louder. Still nothing. I was worried that Alex would be out of the bathroom
before Renee opened the door. Maybe that was what she wanted, to have him
find me waiting at her door like a sad puppy, with pink panties on. I was
so relieved when Renee pulled the door open that I almost hugged her. It
was such a close call that I actually heard the bathroom door starting to
open right as Renee pushed her door shut.

            "You made it, slut," Renee said, "Too bad, I wanted to ask your
friend what he thought of my photography skills."

            I waited, silently, for my instructions.

            "We're going to start with some sucking tonight," Renee stated.

            After a beat, she decided to clarify, "That means on your
fucking knees, slut! Mouth open, eyes closed."

            I did as I was told. I had this strange fantasy pop into my
head that maybe Renee and Alex knew each other, and she was going to use
this opportunity to steer his dick into my mouth.

            "You're such a slut," Renee said, observing my growing arousal
as the head of my cock stood proudly out above the panty's waistband, "It's
good that you get turned on being on your knees. Now, start sucking."

            My lips closed around whatever Renee put in my mouth. It wasn't
her hairbrush. There was no plastic taste, and the shape was wrong. It was
almost a perfect cylinder, just a little wider than my thumb at the
knuckle, but tapering at the far end. As I slid further up, I felt the
object get smaller and then flare back out a little bit.

            "Get it soaking wet, slut," Renee commanded, "Lots of spit.
It'll make this easier on you."

            I gave the phantom object the sloppiest sounding mouth fuck I
could. After what felt like forever, Renee told me I could stop and
carefully pulled the thing back out of my mouth.

            "Open your eyes," she ordered.

            I saw what the object was. It was one of the handles from a
jump rope. It was wood, sanded and coated with something that made it about
as smooth as glass. The narrow part was where the thumb would go, I guess,
with the end flaring back out and the ring on the end for the rope to
connect to.

            "Get on your hands and knees and turn around, slut" Renee said,
"Its time to pop that cute little cherry of yours."

            My heart was racing as I assumed the position. Renee got behind
me and I felt her hands on my ass. She was spreading my cheeks apart,
pinning the seat of the panties to one side with a thumb. After she spat on
my asshole a couple of times, my cock was rock hard. She began to rub the
end of the handle against my tight little butt hole, smoothing her saliva
around. I couldn't help tensing up when she tried the first push.

            "Just relax," she said, "don't try to squeeze or anything until
its all the way inside."

            "Yes, Renee," I said.

            I was biting my bottom lip as she made her second push. With a
little twist, she manage to slip the tip of the handle in. It felt strange
at first, almost like I had to go to the bathroom. A brief episode of panic
happened when I wondered what terrible tortures Renee would rain down on me
if I did go to the bathroom while she was stuffing me, if that was even
possible.

            She eased some more of the handle inside of me and started
bouncing it a little, just feathering it with her fingers. It felt like she
was sending ripples of pure pleasure through my whole body, but at the same
time I was stretched more than I was used to and it did hurt a little.

            Renee took her time, slowly burying the handle in me. When she
pushed it far enough for the narrow spot to line up with my butt hole, the
pain went away and I really relaxed. The feeling of fullness was wonderful,
but something strange had happened.

            I looked down and saw my hard on was gone. My dick was just
hanging down, longer and thicker than usual for it being that soft. I had
another brief moment of panic, worrying that somehow Renee had broken my
dick, but that went away when she started to slowly work the handle in and
out of my ass. It felt so good I couldn't believe I'd never tried doing it
to myself before. It felt like my whole body was involved, not just my
dick. Don't get me wrong, my dick was happy too, judging by the thick flow
of pre-cum that was constantly drooling from the tip.

            When I started to get off, it happened with absolutely no
warning. Even though my cock wasn't even standing up straight, my cum just
started pouring out. It wasn't like normal, either, it felt like my whole
body was going to drain out of my dick. There was nothing I could do but
collapse into the pool of my own goo, ass sticking up in the air with the
handle still hilted inside of me. Apparently, Renee's last thrust had done
the job.

            As soon as I was able to talk, I started apologizing to Renee
for cumming without her permission. She gave my right cheek a squeeze and
told me, "It was your first time, so its okay. Your punishment won't be too
severe."

            She put my panties back in place, covering up the little bit of
the handle that was protruding from my ass. She handed me a towel and told
me to clean up my mess. I did exactly as I was told, scrubbing the carpet
as I stayed on my hands and knees, wondering when, if ever, Renee would let
me take the handle out of my butt.

            She kept toying with me while I was cleaning up, giving little
tugs on the handle through the panties only to push it all the way back in.
By the time I had as much of the floor and myself cleaned up as possible,
it almost felt like she had me ready to cum again.

            "Get dressed," Renee said, pointing to the shorts and shirt I'd
brought with me, "Oh, don't worry about the handle. You don't have to wear
it all night, just until your friend leaves," Renee smiled, "but I don't
want him to leave for at least half an hour."

            I had a lot of questions, like was it safe to leave it in that
long, and how was I supposed to sit down, but I knew asking any of them was
going to make things worse for me, so I just put my clothes back on. I made
the mistake of turning back to ask Renee about the sitting thing, because I
was worried about that the most.

            "You've been dismissed, slut," Renee said, a little too loudly
for my comfort.

            With nothing else I could do about it, I let myself out of
Renee's room. My first stop was the bathroom. I checked in the mirror to
see how obvious it was that I had something stuck up my ass. As it turned
out, the loose fitting shorts did a pretty good job of hiding it. It would
show a little if I bent over far enough, but that was kind of a no-brainer.

            Alex was waiting in my room when I got back. It felt so
strange, walking around with something in my ass. It seemed like I was
constantly in this weird aroused state where my dick and my balls felt
bigger or heavier than normal. When Alex was momentarily distracted, I
managed to rummage around in my shorts enough to flip my dick up so that
the waist bands for the panties and shorts held it in place. With just the
hem of the shirt to hide the head of my cock where it protruded above my
shorts, I had to lean forward a little to make things less obvious.
Luckily, it was a dark shirt so I hoped it would help hide things if my
cock started drooling too heavily.

            Sitting down took a little work, but after one false start, I
managed to get into a position on the chair where the bit of the handle
that stuck out wasn't a problem. Unfortunately, I was so focused on getting
myself comfortable without looking too strange, I wasn't paying much
attention to my guest.

            "I think I'm going to go," Alex announced.

            "No, please stay," I heard myself say, "Its just that I don't
get to hang out with other guys a lot. Just Renee and her mom, so it is
nice to have someone over."

            "I guess I could stay a little longer," Alex admitted, "but not
too much. If I'm not home by my curfew I'm going to be in trouble for a
long time."

            We watched funny internet videos and talked about video games
for a while. Basically, we talked about everything except what I wanted to
talk about. The tricks Renee showed me with the handle had felt so good, I
kind of wanted to share them. Of course, I was worried that maybe they only
felt good because I was Renee's little panty boy slut, and a real guy like
Alex would be grossed out by it.

            When Alex did finally leave, he made me an offer that I really
hoped Renee and Mrs. Hamlin would let me take him up on: He invited me to a
sleepover at his place on Friday, promising video games, his dad's porno
collection, and access to the liquor cabinet. Alex referred to it as my
jailbreak from the estrogen prison. Even though I knew Renee was going to
make me pay for even asking if I could go, I knew that I really wanted to.

            As soon as Alex's car pulled out of the driveway, Renee arrived
to pull the jump rope handle out of my ass. She held it out by the ring for
me to take, meaning I had no other way to grab it than by the parts that
had been inside of me.


            "Keep this with your other things, and bring it to my room
whenever I call you," she said, "By the way, slut: Make sure you clean it
really well. It always goes in your mouth before it goes anywhere else. If
it is ever dirty when I call on you, it will stay in your mouth until it is
clean again."