Date: Sat, 31 Jan 2004 13:42:00 -0800
From: joan mitchell
Subject: Rob's Sissy Boy 3

 It had been a few weeks since Rob and I had our second affair.  I was
almost sixteen, Rob was a year older.  Having sex with your brother is
sometimes not as convenient as it may sound.  Having to wait until everyone
else was safely out of the house was not easy.  I would have dressed in
girly undies and fuck every night if possible.  It was rough waiting weeks
or months for it to be safe.

  Finally our parents were going out with another couple for the evening.
That would keep them out of the house until one or two o'clock.  My younger
brother was having a sleepover at a friend's house.  Phil, our oldest
brother was at college.  This gave us a few hours if Rob got home early.

  Rob was out of the house before the parents left.  But before he left, he
caught me coming out my room and told me "be in mom's room after they
leave".  My heart jumped to my throat.

  I didn't love Rob as in boy/girl love, but I did love the way I felt
dressed in satin and lace getting cum pumped into my sissy ass.  It could
have been anyone banging me as long as I was wrapped in sexy underthings.

  Around seven thirty my parents went out.  I immediately rushed to my
mom's dresser.  Opened the top drawer and ran my hands among her things.
After a few moments lost in my fantasy, I realized when I was hamper
diving, I came across some of mom's things that weren't in this drawer.  I
closed the top drawer and reached down to open the lower drawer.

  There they were, mom's special lingerie.  Instead of fairly plain white
and pale pink, these undies were sexy.  Here were deep blues, bright pinks,
reds and lavenders.  I almost fainted. I had hit the jackpot.  I thought
that I could never be able to pick from all these sexy bras, panties and
garters.  I had to make a decision soon.  I wanted to be dressed when Rob
came home.  Which should not be long.

  After changing my mind a couple times, I decided on a lavender set.  Bra,
bikini panties, garter belt all of smooth, shiny satin.  I also found a
pair of sheer black stockings to finish the outfit.  While making my
selection, I thought how, I wanted my own slutty lingerie someday.

  Running back to my bedroom, I couldn't wait to put these on.  I threw
everything on my bed and closed the door.  Rob's room and mine were the
farthest rooms from our parent's.  This would give us a few extra seconds
of valuable time to arrange ourselves if they came home early.  Rob was
expecting me to be in mom's room, where he fucked me twice before, while I
was dressed in some of mom's undies.  I was going to surprise him by being
in his room dressed and waiting.

  I began to get undressed, my hands trembling as I took off my pants and
underwear.  I then realized I hadn't brought any tissues to form my boobs.
Naked, I ran back to mom's dresser and grabbed a hand full of kleenxes.  I
was now more even more excited after running nude through the house.  I sat
down on my bed to calm down.

  In a few moments I was better.  I stood up and held the bra up to my
face.  Pulling it to my nose and nuzzled the soft satin cups.  It had a
sweet sexy fragrance from mom's perfumes.  I was so jealous of the silky
things that girls could wear.

  I put the bra on and stuffed it to look as close to breasts as possible.
Next the garter belt, with its six straps.  The belt, I used before had two
straps per stocking, this had three.  This was getting complicated, but
would be more fun to hook the nylons, I though.  I hooked the belt behind
my back, being sure I had the straps even on either side.  As I started to
put on the nylons I began to get a little nervous.  The though of tearing
or putting a run in them was a little scary.  I pulled up the first
stocking, attached the three straps.  I loved the feel as the top of the
stocking reached my thigh.  That bare thigh between the nylon and the belt
is so sexy.  I hoped the second stocking went on as easy, and It did.
After the claps were on I stood up to the feel of the nylons tugging on the
belt, I loved that feeling.  My sissy bum was being teased by the garter
straps as they brushed against my cheeks.  I began to rub my stiff sissy
cock and balls.

  Last was the pair of bikini panties.  As I stepped into the leg openings
I knew the tiny front would not hold my balls and sissy cock completely.  I
had a small cock, even for a teenager, but the bikini was not much more
then two small triangles with a string holding it together.  The panties
waistband pushed my clit against my tummy as I pulled them on to my hips,
my cock head peeking out over the top.  I wanted to see how I looked
dressed.  I stepped in front of the mirror and liked what I saw.  I admired
the color and shiny look, as I ran my hands over my hips.  I turned
sideways, pushed my butt back, and did a forty's type pinup pose.  I though
that one of these times I'll see if I can fit into some of mom's high
heels.  I turned with my back to the mirror, bent over a little more and
looked over my shoulder.  I was staring at a sexy girly ass, shimmering
with the satin lavender material form fitting my cheeks.  I wiggled my
sissy ass wishing it that was receiving some attention.

  I was ready for Rob now.  I grabbed my robe and headed for his room.  The
robe was in case our parents came home early and we had to get decent
quickly.  I felt like a slut, slowly strutting down the hall dressed in
mom's satin lingerie.  Instead of going directly to Rob's room, I walked
throughout the house, loving the stocking and garter straps caressing my
legs.  The soft satin panties sliding over my bum, the bra lightly hugging
my chest, it was very sexy.

  I finally got to Rob's room.  It was kind of a mess.  He had clothes
lying all around.  I had to clean off his bed to sit down.  My anticipation
was building.  I leaned back on his bed and stretched out.  With my feet on
the floor and hips on the edge I started to caress my cock. It was still
poking out from its satin wrap.  I didn't want it stiff all night.  I
reached in to Rob's drawer next to the bed and found the gel we used the
last time.  I put a small amount on my fingers, and with the other hand
pulled my cock through a leg hole.  Rubbing the gel all over my cock sure
felt good.  I worked my hands along its stubby length.  My fingers wrapped
lightly as they glided over my gel covered cock.  I closed my eyes, laid
back and rubbed as my jizzum began to boil up for its release.  I laid
there, exposed to anyone who might come in.  That though brought me to the
point when I couldn't hold back any longer. I hoping Rob would walk in
before my load shot, but it was to late.  My hot cream blasted out in a
long stream on to the bed.  The following shots were less forceful and
landed on my hips and fingers.  After milking the last drops out I stopped
to enjoy the afterglow as sticky goo ran off my hip, down the side of my
butt cheek.

  I needed to get cleaned up, Rob could be home any minute.  I found a
towel by the bed.  Rob probably beat-off in it, that was fine with me.  I
wiped the cum from the bedcover.  With my sticky fingers, I scooped the
jizzum off my hip and cheek, brought it to my mouth and lick it clean.  A
last wipe of my cock head with the towel, I didn't want my panties stained
yet.  I still hadn't figured out how I was going to wash them out and get
them back in mom's drawer.  I knew I probably would not have enough time
tonight. I laid the towel at the end of the bed for easy clean up later.
Tucked my sissy cock back into the panties, laid down and waited.

  I rolled onto my stomach so that the first thing Rob would see as he
walks through the door was my shinny satin covered ass.  About ten minutes
later I heard someone come through the front door.  After a couple doors
open and closed, I heard Rob's voice call out "where are you?".  I yelled
out "back here".  His footsteps got closer.  I could hear Rob open my
bedroom door then he said "where?".  I called out "in your room".  He
slammed the door closed and headed to his room.  As he came up the hall he
said "you're suppose to be in mom's room".  He continued with "we only have
an hour or so" as he walked through the door.  When he saw me dressed and
in my slutty pose he closed the door while saying "great, we'll have a
little more time now".  My dressing earlier helped add a few valuable
minutes to our evening.  He walked to the side of the bed and sat down.
Rob sat near my hips, looking down at my bum and legs.  He reached out and
touched my stocking covered leg.  His fingers were down between my thighs,
just below the tops of the nylon.  Rob's hand slowly slid down my leg to
the back of my knee.  Then slowly he ran his hand back up until it touched
my bare thigh at the garter strap.  He asked me where I got the outfit.  I
told him "in mom's lower drawer.  She has a whole drawer full of sexy stuff
like this".  I asked him if I surprised him being dressed.  He said "I knew
something was up you were back here.  But, that I didn't expect you to be
dressed and ready to go".  Rob slipped his hand up to the edge of my bum,
then up on my cheek.  He lightly patted the buttery soft satin wrapping my
bum.  His fingers slid under the elastic band and massaged my bum.  Rob's
thumb worked its way down my butt crack until it was brushed against my
puckered hole.  When its tip pressed at my opening, I wiggled.  He leaned
over and lowered his face to my butt, lightly planting kisses on each
cheek.

  I told him that he should get out of his clothes.  He mumbled his
agreement as he stopped and got up.  I rolled on to my back, one leg bent
back up trying to look sexy.  I must have looked pretty good to him,
because his eyes never left my body.

  As soon as Rob was naked, he stepped over to the bed near my head.  His
six inch cock standing straight out.  I reached up and took hold of his
shaft to pull it closer.  I raised my head up to kiss the under side of his
shaft and sack.  I began to nibble his cock like an ear of corn.  His balls
caressing my cheek, I moaned as I worked my lips to the head and swallowed
it in my warm waiting mouth.  He jerked a bit then leaned forward, stuffing
his cock head down my throat.  When his cock was fucking my ass pussy it
felt like it was ten inches long, but in my mouth it was just the right
size.  I drove my nose into his pub hairs.  If Rob's cock had been another
inch, it would have gagged me.  As I moaned my pleasure, I thought that I
was getting pretty good at cocksucking.  My head was tilted at an angle, I
was raised up on my elbow.  Rob put one hand on my cheek and another on my
head, then pulled as his cock sank deeper.  Then pulled his hips back so
his shaft slid along my tongue.  I held on to the head, not letting it get
away.  My tongue swirled around its tip.  Rob was willing to face fuck me
as we were, but my position was not comfortable.  As I held his cock in my
mouth, I moved around so that I laid across his bed.  As I lowered my head,
Rob had to kneel down.  I hung my head over the beds edge, my nose against
his balls.  Rob held my face in his hands and started his probing of my
throat.  He had a straight shot in.  Rob's sack was slapping the bridge of
my nose.  He sped up his pace, until all I could do was lay there and take
it.  I reached out and grabbed his ass cheeks and held on.  If I hadn't
propped my feet on the wall beside his bed, I would have been pushed half
way across it.  Rob's cock almost popped out a couple times as he pulled
back.

  Rob was grunting like a bull in heat.  His pumping increased as he neared
his release.  By the way Rob was fucking my mouth, I thought if he shoots
now, I'm going to have to work fast to get him hard again to ream my ass
tonight, because that’s what I wanted.

  Suddenly Rob stop, buried deep in my mouth and held there.  He seemed to
be fighting the urge to release his full sack of cum into my stomach.  He
must have decided my ass was more inviting.  I laid quietly, fighting the
urge to my wiggle my tongue around his plump head.  Rob's breathing slowed
and his cock shrank slightly.  He said "do you want it like this or in you
ass, right now I don't care".

  I let go of his butt and pulled my mouth off of his cock, it bobbed in
front of my face.  I swung around, put my knees on the floor and laid on my
stomach, face down on the bed.  My ass was presented to him for his answer.
Rob reached on to my hips, carefully slipped the bikinis over the garter
straps and down to my knees.  I lifted a leg to remove it off.  Once it
cleared my foot and off, Rob moved in between my feet and spread my legs
apart.  My ass pussy, sissy cock and ball sack were exposed to his desires.
I felt completely open to him.  Rob complimented me by saying "from my
view, it as good as a girls, if it wasn't for what's hanging between your
legs.  The garter and stockings framing my ass must have been an appealing
sight to him.

 I could feel Rob's face near my ass cheeks.  His warm breath softly
ticking the fine hairs on my bum.  Rob stuck his tongue into my pussy crack
at the base of my cheeks.  My butt tightened up then relaxed, not knowing
what he had in mind.  He slid his hot tongue up along my crease to the
small of my back.  Then worked his way back down, planting soft sweet
kisses on my cheeks as he went.  My girly cock was trapped against the bed,
I was unable to reach it to rub.  As Rob leaned back from tonguing my bum,
He reached between my thighs and fingered my stiff clit and sack.  He seem
to be solving my problem.  His fingers run down and up along underside of
my clit cock.  Then he began to finger my sack.

  Rob's attention was great but we needed to get to the most important
action.  That was reaming my ass pussy.  I told Rob that we better get at
it if we wanted to finish with time to spare.  He agreed and reached for
the jar of gel.  I heard him grease himself and then he started to smear
the lube around my tight pussy.  I told him to put a lot of gel at my bum
hole and not to spend a lot of time working it in.  I buried my face in a
pillow, knowing when he pushed in, it would hurt, but time did not allow
for anymore playing around.

  Rob poked his finger through a couple times, then smeared more gel at my
entrance.  On his knees, he crawled until his cock head was against my
opening, his thighs against my stockings.  I felt him pushed in, I prepared
for the pain.  He grabbed my hips and leaned forward.  The head of his cock
slipped off to the side, unable to keep aligned because of the slick gel,
and my tight hole.  Rob place a hand between us, held his shaft to keep
himself straight.  He pushed in again, this time forcing my pussy open.  My
hole started to give, as the head pushed through.  I moaned into a pillow
from the sharp pain.  As the head passed inside, my rose bud clamped around
his shaft.  Feeling inch after inch slid in, I was ready to cry. Rob did
his best, taking it slow, to minimize my discomfort.  I needed to get my
hole loosened to accept him.  With a deep breath I impaled myself back on
his cock.  His head was now buried deep inside.  I arched my back from the
stabbing pain that run through my pussy.  With my cheeks against his
thighs, we held motionless for a few moments as I adjusted to his expanding
shaft.  I thought to myself that the next time I'll loosen myself up if
necessary.  I needed to fined something that would fit my pussy, but that I
could keep in my room without anyone suspecting anything.

  Rob brought me back to reality when he asked "are you ok?".  I nodded my
head yes.  He pulled back until he was almost out.  Rob let go of my hips
and grabbed hold of the garter straps, using them to pull himself against
my ass pussy, and forcing his cock deep inside my bum.  I was beginning to
enjoy myself now.  He started his in and out rhythm, picking up the pace a
little more each time.  As Rob slammed harder, my butt cheeks quivered, as
his thighs slapped against me.  He was using my ass like a spring.  He
pulled hard forward sliding into me, his hips smacking against my bum then
bounced back pulling his shaft outward.  My insides were jarred each time
he pull in.  Rob's speed quickened as his force increased.  My ass pussy
was being hit so hard that I thought I was going to split open.  His ball
sack was slamming into mine.  My balls were tender from being slapped, it
felt like someone was using them as a punching bag.  I was afraid Rob would
tear the straps off the garter belt.  But at that point I didn't plan on
stopping him.  I needed Rob to finish fucking me.  I wanted and needed his
hot cum coating my walls.

  Rob was on the verge of granting my wish.  As he plowed into me, I told
him to fuck harder, if that was possible.  He tried.  Rob pulled out to the
edge of my hole, pulled me back.  Pushed in to me as we both slammed into
the bed.  It felt like he was now trying to punish me for asking for more.
I wanted him to keep fucking, but my body was taking a beating.  He pounded
into me as the first jets of cum blasted inside.  Rob's cock pulsed with
his warm juice as it splashed my insides, I could feel each shot hit.  This
is what made it all worthwhile, getting filled with warm gooey cum.  Rob
slammed in again and stopped moving, his cock twitched uncontrollably
inside my pussy as he continued to shoot loads of jizzum into my bum.  It
seemed like he would cum all night.  I thought how long it had been between
each fuck, and wanted them to last longer then they did.

  As Rob's shots of cum began to hit with less force, he began to work his
cock out and in, squeezing each drops out.  Rob milked the last drops of
goo from his shrinking dick. He kept moving out and in but his member was
loosing it stiffness.  I was ready to stop finally.  I had enough for
tonight.  I was sure that we would do this again.  By Rob's grunts and moan
and the force of his fucking my ass, he seemed to be satisfied with me.
 
  Rob reached for the towel as he pulled himself out.  I wiggled my ass in
satisfaction to him as he leaned back on his heels.  Rob began to clean
himself, then he said "that was the best yet".  I smiled and moaned into
the bedcovers my agreement.  Rob's gooey cum began to leak out of my pussy
hole and dribbled down my leg.  I felt Rob press the towel against my bum
hole and dapped up some of the mess.  I reached around and grabbed it from
him to clean myself.  Rob tenderly patted my ass cheek and moved away.  I
was afraid to move my legs.  I knew my joints were going to be sore from
having my ass bent over the edge of the bed for so long.

  Rob said "better clean up.  You only have an hour or so, I'm going back
out for awhile".  I knew I had to get moving, but I could stay in that
position all night.  My bare ass was poised to be fucked again.  As I wipe
my bum, I wondered what it would be like getting gang banged.  I thought
that some day I may find out.

   I stopped day dreaming and got back to the present.  I finally began to
lift myself off Rob's bed.  My hips and knees were sore as I gingerly began
to stand up.  I had been bent over for a half hour.  As I straightened up I
looked down to my semi-hard sissy cock.  But to my horror I noticed that
the stockings were torn at the knees.  They were ruined on the carpet as
Rob fucked me.  Rob was still in the room and saw the nylons.  I began to
panic, but Rob told me "just go get a new pair before she notices them
gone".  He reached into his pants pocket and handed me two dollars to help
replace the stockings.  He then gave me five more dollars and said "buy
some panties for yourself".  Rob left to clean up and went out.

  I sat down on the bed with the towel under my tender bum to catch the
remaining dribbles.  I tried to figure out how I was going to buy a new
pair of stockings and some panties for me.  Rob would have to drive me to a
department store out of town so I wouldn't run into anyone I knew.  I was
kind of young to be buying women's things.  I needed an excuse.  If asked,
I'll say that I'm being hazed to get on a team.  That my teammates were
forcing me to buy women's lingerie.  That should work, If not I'll just
tell the saleslady that they're for me.  Why should I care what some woman
I don't know thinks.  Maybe I'll buy myself some things too, while I'm at
the store.  I'll have my own lingerie to wear.

  As I sat on Rob's bed in mom's bra, garter and torn stockings, and her
bikini panties looped around my ankle, I came back to reality.  What a
sight I was.  I reached down, lifted my foot and removed the panties.  I
needed to get moving and clean myself up.  I knew I didn't have enough time
to clean mom's things and get them back in her drawer.  So I would put the
bra and garter back, clean the panties by hand and replace them when I had
a chance.  I could hang them in my closet until they dried.

    I slowly walked back to my room and closed the door.  Laid the bikinis
on the bed.  I began to take the bra off, forgetting the kleenxes were
still in the cups.  They spilled out on to the floor.  I inspected it for
stains then tossed it on to the bed.  Next I unhooked the stockings and
left them on the floor, they were ruined.  Last was the garter belt, the
dangling straps were tickling my thighs as I had a little trouble getting
the hooks undone.  After looking it over, I laid it next to the bra.
Feeling slutty, I slipped the panties back on and headed back to my mom's
dresser to replace the belt and bra.  The feel of the satin caressing me,
as I pranced around, was making me hard again.  When I got back to my room
I figured I better take them off or I'll be beating off again.  I sat down.
I wanted to get a shower, or maybe a nice warm bath to soak my sore bum.  I
also needed to wash out the panties.  I figured I would do both at the same
time.  I'll take a bath and hand wash the panties.

  I needed to get going it was getting late and I wanted to be done before
my parents got home.  Rob had the easy part, walk in get his cock sucked,
pound my bum, then leave.  No cleanup, no fuss.  But for everything I had
to go through to have our affairs it was worth it for me.  Being dressed in
sexy lingerie was the main reason I accepted having my bum hole stretched
wide open by a hard cock.  But I was beginning to enjoy the ass fucking
part almost as much.  If Rob was willing, I planned to continue with our
affairs.

  And we did continue, more stories to come.