Date: Sun, 18 Jan 2004 14:17:44 -0800
From: joan mitchell
Subject: Rob's Sissy Boy 2

  My love of lingerie during my early teen years was directly responsible
for my first sexual experiences.  But the sex was not with a girl, but with
my brother Rob.

  I loved the look of a girl's ass in a pair of skin tight jeans.  The
sight of long legs with the ass cheeks peeking out from the edge of a pair
of short cut-offs made my teen dick hard.  I did love girls, just that I
was too shy to approach them.  After my first sissy ass fucking, dressed in
mom's panties and bra, I wanted to do it again.  I was always thinking of
sex, so sex with Rob would be my release.

  About a month passed since our first dress-up sex.  I wasn't sure if
there would be a repeat.  The coming weekend, my parents were going away
with my younger brother.  My older brothers, Phil and Rob, went out Friday
night.  I stayed at home to see what might happen.

   Nervously I sat watching tv, waiting to see if Rob would want to fuck my
sissy ass again.  I loved it when I was dressed up in sexy underthings.
Being treated like a girl was what I wanted.

  At around eight-thirty I heard someone come in the front door.  Rob
walked in, looked around the living room, saw me alone, then went to his
room.  Minutes later he was back out, going room to room checking to see
who else might be home.  After he was satisfied that we were alone, he
entered the room and said to me "lets go".  As if I had no control, I
hurried up off the chair and followed him in to our parent's room.

  Rob pulled out my mom's lingerie drawer, and started to search through
her silky undies.  Rob picked up the same things I wore the first time.  I
moved beside him and said, "no, I wore that the last time.  I'll do what
ever you want, if I feel sexy.  So let me pick the things I want.  If I'm
happy, I'll make sure your happy".  I wanted something sexier this time.
Rob looked at me with a slight grin, and dropped the panties and slip.  As
I nudged over to the middle of the drawer, he stepped back and sat down on
the bed.

  I began to run my hands through the piles of nylon, satin and lace,
wishing they were mine.  As I pulled items out, I would hold them to my
waist to see if they might fit.  My mother was shorter then I, but had wide
hips and large breasts.  I did not have a girly body but I could wear most
of mom's things. It was the perfect age for me to be sissy dressing in an
otherwise all male house.  I had no sisters to raid their panty drawers.

   I then found a pink bra I liked, and a pair of matching satin panties.
As I searched for something more, from behind me Rob said "strip down".  I
told him I wasn't finished yet.  He said "you can look after you take your
clothes off.  I smiled and put the things down.  As I took off my shirt, I
could see Rob behind me getting undressed in the mirror on the dresser.  He
was out of his pants and underwear in a flash.  I dropped my pants and as I
was stepping out of the legs, Rob was grabbing my jockeys and pulling them
down.  He then reached and squeezed one of my ass cheeks, with his thumb in
my pussy crack.  My cock was standing straight out, in the mirror I could
see Rob stroking his sixteen year old rod.  He was horny and so was I.  Rob
stepped up behind me, pressing his warm naked body against my backside.
His cock was bobbing at my butt crack, smearing precum on my cheeks.  Rob's
hands on my waist pulling me in to him.  He then reached around me and
wrapped his hand on my girly cock.  I could have shot my gooey load all
over mom's open drawer.  His middle finger slid to my cock head and he
began to finger my cock hole.  Rubbing drops of ooz over its head, I was
weakening.  But I wanted to be dressed in mom's silky things before we
started. I pushed him away from me and told him to go sit down, so I could
finish my selection.  Rob sat back down, and with a demanding voice said
"hurry up, we don't have all night".  He was right, we could not lose track
of the time.  Phil would be out for a few more hours, but we could not have
him surprise us by coming in earlier.  After a few seconds more I grabbed a
garter belt and white nylons to complete the set.

  I picked up all my pink things and put them on the bed between us.  I
pulled the satin bra out from the pile, held it up to my nose and inhaled
the smells.  Then reached out my arms and to put it on.  I sled my arms
through the straps loops, grabbed the clasps and pulled them to hook them.
As I did Rob reached over and tickled my balls as I struggled with the
bra. I wiggled away telling him to wait.  We both couldn't wait but I
wanted to be dressed up.

  After hooking the bra, next came the garter belt.  Rob looked at it and
said, "Why do you need that?"  I told him to relax, that he would like the
finished look when I was done.  I hurried and hooked it to my waist.  I was
really starting to feel sexy with the clasps dangling down my thighs and
ass.  Next I sat down and took a nylon in my hands with the thumbs inside.
I'd seen women in the movies do it this way.  I gathered it up until the
heels were at my thumbs.  Bent over and slowly stretched it up my leg,
careful not to rip it.  After it was attached at the clasps, I then worked
the other on and fastened it.  I could feel my cock throbbing from the
building excitement.  My first garter and nylons what a slut I was.  As I
stood up to put on my panties, I felt the sexy tug of the nylons on the
garter straps.  The feeling was heavenly, I felt like a slut now.  Rob told
me to turn around.  He wasn't completely in to the dressing up part, but he
knew I would cooperate easier if I got to dress up.  He just wanted to get
to the sex.

  Last came the pink satin panties with lace trim.  I bent down and held
them out to step into them when Rob asked, "why didn't you put them on
before the nylons are hooked up?"  I said that with them on the outside I
could take them off without the nylons getting in the way.  He nodded his
approve.  I pulled the panties up over my stiff sissy cock.  They didn't
fit well with my cock poking out from inside.  I wanted a more girly look,
so pulled my cock out of a leg hole and began to rub along the shaft.  Rob
asked what was I doing, I told him I didn't want my cock to show.  Still
standing, I continued to pump away.  Rob slid closer and cupped his hand
and reached out just beyond my cock.  I started to pump harder and faster,
totally loving the feel of my sexy things.  I roamed my free hand over my
satin covered ass and fingered the garter straps.  My point of release was
approaching.  I moaned softly, closed my eyes and tilted my head back.  I
shot load after load from my sissy cock, until my balls were empty.  I was
spent and sat down on the bed.  Still shaking with tiny spasms all over my
body.  With my head back, my eyes still closed, I felt something wet hit my
lips.  I opened my eyes quickly to see Rob's hand above my mouth dripping
my own cum on to my lips.  I kept my mouth closed until the gooey warm cum
ran down to the corners of my mouth.  Rob said, "open up".  I opened my
mouth and let the sticky juice hit my tongue.  It was bland and salty, but
not offensive.  Rob dripped most of the jizzum in to my waiting mouth.
When no more drops fell, Rob told me to lick his hand clean.  I slurped and
licked until it was all gone.  I used my finger to wipe the goo off my
lips.  Stuck the finger in my mouth and licked it all.  I did enjoy that.
Men have no idea how sexy cum makes you feel.  It's warm, sticky and your
willing to do anything after you've ate cum.

  I wanted to do what ever Rob told me to do now.  I stood up and pushed my
shriveled girly cock back into my panties, tucking it down between my legs.
Now I looked like a girl, and I felt like one.  To finish the illusion, I
stuffed Kleenex tissues into the bra cups.  Mom probably wandered what
happened to all her tissues.

  While I filled my cups, Rob slid on the bed, laid on his back.  His cock
standing up waiting for some attention.  I did not need Rob to tell me what
he wanted me to do.  I got on the bed on my hands and knees and straddled
over his legs, with my lips above his bobbing cock head.  Rob's hands back
behind his head, he watched me as I opened my mouth and stuck out my tongue
just above his cock.  I stayed like that for a few moments as saliva mixed
with my cum started to run down my tongue and drop on to the tip of his
cock head.  His cock twitched when the first drops hit.  More of the warm,
sticky goo dripped down, running off the head and down the shaft.  The
fluids reached his balls and puddled between his thighs.  Rob's cock was
sparkling from the light shining off the saliva cum mix.  I lowered my
mouth until my tongue was just touching the hole on its head.  I flicked it
a couple times and licked up some of the salty concoction.  Rob moaned,
"suck it", but I wasn't going to hurry this.

  I moved off of Rob and turned my satin ass around on the bed until my
cock was above his face.  I told him that I would take care of him if he
gave my ass and cock some attention.  Rob reached up and began to rub my
smooth pantied covered cheeks.  I held up my end, so to speak, and lowered
my mouth down over his shiny purple head.  As Rob's cock slid over my
tongue, all the way in, my nose bumped into his smooth wet sack.  (We were
both past puberty, but pretty much hairless around our balls.)  I could
have drowned in the puddle of drool juice around his balls. My lips gripped
his shaft as I lifted my head up and off.  I leaned forward and down to
lick the mess between his legs.

  Meanwhile, Rob was rubbing small circles, with his fingers over my
pantied sissy ass and occasionally would slip his hand between the garter
straps and my bare thighs.  Rob would trace along the elastic leg band with
his fingertips, slip one inside, pull and lightly snap it against my
cheeks.  It was very sexy.

  I cleaned up the puddle around his sack, and went back to sliding my face
down and up his tasty rod.  I would bob a few times, release it.  Then rub
my lips, nose and cheeks along its length.  I could not get enough, I loved
the slippery, silky feel of it as I nuzzled and kissed it all over.  I
rubbed my lips over its rubbery head, planting soft kisses at the base and
balls.  I was in love with his pink and purple cock.  It was the only thing
that mattered to me.  I loved it and had to worship it.  I moaned with
satisfaction as I buried my face in his pubs.  I was lost in the lust.

  I was concentrating on Rob's cock so deeply, that I did not feel him
pulling the leg band over to release my growing sissy cock.  Before I had
realized it, Rob was darting his tongue up around its head.  I now began to
moan from the sensations of both cocks being loved.  I needed my cock
sucked and I had to have Rob's in my mouth.  I kept going up and down and
around Rob's twitching cock.  My tongue started to ache, but I didn't want
to stop.  Rob was teasing me, by licking and nibbling at my cock head.  He
scraped his teeth over its spongy helmet head, he was driving me crazy.  I
would push my hips down forcing my sissy cock passed his lips, then raise
back up.  We would do that over and over again.  This went on for a while,
who knows how long.  It was good that I had jerked off earlier, I could now
last longer before my next release.  I want it to last as long as possible.

  As we wiggled and moaned, I felt Rob finger the skin behind my ball sack
and trace a line to my pussy hole.  He fingered the puckered edges, causing
me to moan softy into his sack.  He then removed his hand.  I could feel
him moving under me.  Moments later his finger retuned to my pussy, this
time covered with a cool gel.  Rob must have put a jar on the night table
earlier for easy reach.  He diddled at the tight opening, then press his
finger slowly through.  It threw off my bobbing rhythm on his cock. I
stopped and held Rob's shaft in my mouth, rubbing it with my tongue as he
worked his finger deeper in me.  I wiggled my acceptance of his invasion of
my pussy.  It was tight but I wanted more.  He pushed in as I pushed back.
The pressure was uncomfortable but worth it.  When he was all the way in he
held it there a few seconds.  Then pulled out to the entrance.  As he
pulled back I leaned forward.  I reached back and pulled my panties to the
side to allow him easier access.  He put a second greasy finger to my butt
hole. I pushed back against them.  He knew I was ready for more.  As the
two fingers slid past my "o" muscle, I leaned farther forward trying to
adjust to the pressure.  But the pain passed quickly, I was starting to
relax now.  I again leaned back as Rob buried them deep, and then ticked my
innerds.  He knew I was loving it.  He pulled out again and added a third
then a fourth finger.  When the last finger started in I slumped forward,
my face between his legs.  My ass was still up in the air as Rob worked my
poor pussy hole, stretching and lubing it.  He started to finger fuck me.
When he pushed in, I pushed my hips back.  He would pull out, I would moved
forward, careful not to have his fingers leave my pussy completely.

  This went on for some time until I moaned out that I could not take any
more.  I crawled forward until Rob's fingers could not stay in.  Rob sat
up, I move to the side so he could get out from under me.  I rolled on to
my back to catch my breath, my head at the foot of the bed.  Rob got off
the bed and told me to spin around with my head on the pillows.  I was weak
but I wanted to go on.  I got turned around, laying on my back, eyes
closed, and my breathing starting to slow.  I could hear Rob at the night
table.  He picked up the jar of gel and got back on the bed.  As I opened
my eyes I saw Rob coating his throbbing cock with gel.  I scooped some gel
and reached for his cock.  My fingers rubbed a thick coating of goo over
its fat head.  I teased his cock rubbing and pulling it.  I was at a point
that nothing could stop me from getting my sissy ass filled by that cock.

  As he rubbed the gel around, I stopped and began to turn over on to my
hands and knees.  Rob stopped me by saying "Don't, I'm going to take you
like a girl, on your back".  That sounded nice, I would just lay there
while he did all the pushing and pulling.  I reached to take my panties
off, working them over the garter straps, down my nylon covered legs.  I
got one leg out, but Rob didn't wait for the second.  As my legs were off
the bed, he grabbed them and pushed them straight up.  The panties hanging
on my ankle, like a slut flag.  Rob moved forward between my silky legs,
Placing a calf at each shoulder, leaned forward so that his weight would
keep them in place.  Rob then slowly slid his hands from my ankles to the
nylons tops just above my balls, fingered the garter straps then slid up
again.  He planted small kisses along my thighs.  I loved the attention but
I wanted a hard cock inside.

  He said " I'm glad you thought of the panties over the garters, they
don't slow things down".  I nodded and smiled.  As he caressed my legs, his
hard cock was bouncing up and down on my ball sack.  Gel was smearing all
over us, his thighs, my thighs, sack and ass cheeks.  I reached for his
balls and rolled them between my fingers.  They were heavy and full.  I
wanted their juice inside of me.  I guess Rob did also.  He stopped kissing
and teasing my legs, inched forward.  Bending my legs up over my chest, my
ass rolled up in the air.  The stuffed satin bra was tickling my chin.  His
cock head was resting at my pussy opening.  I wanted Rob to push it in, but
I was having trouble breathing.  I told Rob that I needed air.  He stop
moving and let my legs drop to his sides.  He told me to, "give me a couple
pillows and lift you ass up".  I tossed them to him, he tucked them under
my hips.  Rob scooped some gel, rubbed it into my pussy hole, then raised
my legs and leaned forward.  His cock was aligned with my waiting hole and
I was ready.

  Rob took hold of his shaft and began to push in.  None of my complaining
was going to stop him now.  I felt the head force its way past my tight
grip.  It had been a few minutes since his fingers were in so I was a
little tense.  I wanted that fat cock in now.  Rob leaned in to me, sliding
his cock head all the way in.  I let out a soft "ooooooh".  Rob moaned in
satisfaction.  My pussy was clamped on to his pole.  I could feel his cock
bobbing inside as he held still.  As it twitched around, I was afraid he
was going to shot his load, so I did not s move, waiting for his spasms to
pass.  Rob fought back his urges to release, and began to pull back out.
He pulled until the head caught at my "o" muscle. I wouldn't let it get
out.  He then pushed in.  It felt like it was getting fatter and longer.
Rob's eyes were closed as he tilted his head back.  I would open and close
my eyes depending on Rob's grunts and growls.  He moved only his hips
slowly back and forth bumping my innerds with his cock head.  Rob would
push in, stop then slightly rotate his hips to make the head wiggle around
in me.  I could not have been happier, I was a sissy girl getting fucked
and loving it.

  Rob began to work his cock, slow and steady, enjoying the feel.  As he
sawed in and out, my muscle massaged his shaft.  Rob reached down and
pulled on my sissy cock.  I lifted my head and looked down.  I could see
his hand wrapped around my cock, framed by the garter straps and nylons.  I
smiled inside thinking that this was so great.

  After stroking my cock a few more times, he let go and began to
concentrate on his cock in my pussy.  I did not mind, I needed my ass
pounded more then my cock played with.  Rob began to pickup the pace,
slamming my ass hole harder and faster.  He's forceful banging pushed my
head into the headboard.  I didn't care at this point.  I wanted him to
pounding away.  Rob was oblivious to everything.  He only cared about
finishing fucking me.  I was his sissy fucking toy, that was fine with me.
Rob now was slamming my soar pussy with all he had.  His hips were slapping
hard into the cheeks of my ass, I could hear the smacking sounds.  I was
pushed farther in the headboard as he fucked me like a man possessed.  Rob
was moving in and out like a machine.

  I was near the end, unable to take much more of the emotions and
sensations I was receiving.  I felt a pulse at my pussy hole as his cock
sank deep into my pussy.  His cum was starting to boil out of his balls.
He pulled out once more then hard in and stopped.  Rob groaned loud and
deep, rotated his hips, grinding into my cheeks, forcing his twitching cock
as far inside as it could possibly reach.  My ass pussy locked on to his
shaft, I felt more pulsating passed through my clinched opening.  Rob's cum
blasted into my innerds, shot after shot passed my pussy hole.  I could
feel each shot of hot jizzum hit inside.  I grabbed the bedspread and
stuffed it into my mouth to muffle my moans of pleasure.  I stiffened my
back and my toes went straight up in the air.  It was like a fire hose was
opened up inside of me.  I was alert to all of my senses.  Rob moved little
except I knew he was tossing his head back and forth, moaning between each
shot he released out.  My eyes were closed tight as I wished it would last
a little longer.

  But of course it didn't.  Rob's few remaining jets of cum were spent long
before I would have liked them to stop.  I wiggled my ass to see if he had
anything left.  He slid out part way then drove back in, milking the last
drops in his vein.  Rob slumped pushing my knees almost to my fake boobs.
My panties daggling above me face.  He took a few deep breaths and
whispered, "damn, that was good".  That was a compliment to me.  He lifted
his hips to slowly pull out then back in a few times as his cock shrank
some.  I was hoping he was going to try and get hard again.  I grabbed his
hips to hold him in.  But he then pulled out completely.  My pussy made a
sound like gas.  Rob made a face at me then said, "thanks a lot, I'm still
back here".  I told him it wasn't gas.  He fucked me so hard that air must
have built up inside.  I giggled a bit at his accusing look.

  Rob rolled to one side as I lowered my legs.  I was kinda stiff from
being that position for so long.  My cock had shrank also.  I had no need
to shoot my load right now.  I could do that later myself.  My soar,
puckered pussy hole began to ooze Rob's gooey cream down the crack of my
butt.  I tried to get up before some hit the spread.  I was to slow, I was
leaving a messy puddle.  Rob tossed me a towel that he had just wiped with.
I shoved it between my legs to catch the rest.  I hopped out of bed,
heading for the bathroom. My joints were tight as I shuffled along.

  I returned from the bathroom, Rob was gathering his clothes and jar of
gel.  I stood in the doorway as he headed out.  He looked at me and said, "
I'm not gay, I just need to get laid once in a while.  Since you seem to
enjoy it when your dressed in mom's under things, I see no harm in, OK".  I
smiled and nodded.

  As he did the first time we had sex, he said "clean up the mess and don't
miss anything if you want to do this again".  Rob walked past me, heading
to the bathroom.  As he went by he slapped my bare ass hard.  I yelled out
from the sting and surprise.  I dragged myself to the bed and sat down to
gather my strength.  I noticed it was almost eleven o'clock.  We had been
at it for over two hours.  How time flies when your getting you ass royally
fucked.

  More stories to come.