Date: Sun, 15 Feb 2004 09:44:24 -0800
From: joan mitchell
Subject: Rob's sissy boy  IV

 The Friday after our latest affair, I asked my brother Rob to drive me to
the mall.  I needed to buy stockings to replace the pair we ruined last
weekend that belonged to our mother.  Rob brought along a friend, Mike.  It
was probably better that someone else came with us.  It could be awkward,
not knowing what to talk about to a brother who's been fucking me.  While
dress in lingerie, I'm willing to do just about anything.  When we're
fucking, we don't talk a lot.  Afterwards Rob usually leaves right away.  I
guess we're both not sure that what we're doing is right.

  I sat in the back seat while they talked upfront.  They discussed which
girls in school they would like to fuck.  Who had the nicest legs, ass and
tits.  I liked girls too, but I was busy planning on what I might buy for
myself today.

  When we arrived at the mall, they took-off together.  But before they
left, Rob told me to be at the car in an hour and a half.  I headed
straight for Penneys.  I knew from previous trips through there they had
prettier lingerie than Sears.  Also, mom shopped at Penneys, so I hoped to
find her replacement stockings there.

  As I walked into the ladies foundation department, my stomach started to
flutter.  I was finally going to buy my own sexy girly things.  There were
so many displays to look at.  I needed to keep focused on what I wanted to
buy.  Not to wonder around looking at all the other lovely things.

  I first wanted to get the stockings for mom, then I could spend the
remaining time on myself.  After looking at the different stocking
displays, I choose a pair that seemed to match the torn stocking I had
brought with me, in my pocket.  The size length would have to be a guess.
I wasn't sure, but since my mother was about six inches shorter than me, I
would get her mediums.  I also bought myself a pair of black, like mom's,
and a pair of white stocking.  I got mine in size tall.

  Now I could browse around for my other things.  Next, I wanted some
panties.  I had checked mom's panties to see what size she wore.  Hers were
size seven, I would buy size eight.  They would be less snug I figured,
that way my sissy cock could slid around in them.  It would feel much more
sexier.  My budget was limited, so I would have to find some bargains.  I
found a bin with a sign that read "4 for $6.00".  There were all styles and
colors.  I picked through the piles of panties and found some I though were
cute. A few women walked by slowly.  I could feel them staring at me as I
searched through the piles of satin, nylon and lace.  But I didn't look at
them,



I wasn't going to let my nervousness stop me from get my things.  I was
going to buy my lingerie, no matter who was looking.

  Next I walked over to the teddies.  They were cute, but I would have to
unsnap the crouch for access to my bum.  I decided to buy a teddy at a
later date, after I bought all my necessities.  I found the girdle and
garter section.  I liked garter belts. Garters are so sexy.  Plus with the
girdle, I would have to take it off to have my pussy pounded.  The whole
point of dressing for sex was that I could wear lingerie while being
fucked.  There were only a few styles and colors, but I managed to find a
belt that was a close match to a pair of panties I had picked.  They were
pink with white lace.

  I figured I still had enough money for some other things.  I wasn't
buying the best stuff, more like the bargain items.  I would get better
things as I saved up.  I headed to the bras.  As I searched through the
displays, a saleslady came over to me and asked if she could help.  I was
nervous and told her that I was fine then thanked her.  She started to walk
away when I decided I needed to get her opinion on sizes.  I asked her if
she could help me size a bra.  I had not checked mom's bras for the size
she wore before I left.  The saleslady asked for whom it was for so that
she might have an idea what the shape might be.  She had a pleasant smile
and a calming voice.  Her nametag read Debby.  I was going to tell her that
I was be hazed by teammates to dress in girls undies.  But I went with the
truth.  I told her that it was for me.  She smiled and without hesitation
said that a 38C would probably fit me.  I think she knew they were for me
before I said so.  Debby started to show me different bras.  I told her I
want to match the pink panties and garter.  She walked to another display
and pulled out an almost perfect match out.  I told her that was the one I
would take.

  Debby asked if there was anything else.  After I did a quick addition of
the things I had picked, I figured I had about fifteen dollars left over.
I asked her if she had any tap pant and camisole sets.  She led me to the
back wall where she showed me a nice selection.  I quickly found a set in
pink, a bit brighter then my other pinks, but that was ok.  Debby suggested
an extra large size.  I was set now.  I had everything I wanted.  I told
Debby I was done for now.

  Debby took my things and we headed to the register.  After paying, I
thanked her for her help.  Debby said that she would be glad to help me if
I came back.  I told her that I would look for her next time.  After
leaving the store, I began to check out some of the ladies clothing stores
window displays as I walked through the mall.  I had about twenty minutes
before I was to be at the car.

  I needed to hit the men's room before I left, so I headed in.  As I
entered I noticed that it was empty.  I went to the stall against the wall
and locked the


door.  I dropped my pants and underwear and sat down.  During a long pee, I
reached into my bag and pulled out the pink panties.  I thought that if I
was quick and quiet I could put them on now and wear them during the ride
home.  Then I got crazy and pulled out the garter and black stockings.  I
would try to get into them all.  After pulling my jeans and underwear off
and hanging them on the door hook, I yanked off my socks.  Then someone
came in to pee.  I quietly slipped my shoes on and waited until he
finished.  He zipped, did a quick hand wash and left.  I took my shoes off
again and began to work the nylons on.  I got each up to my knees then put
my socks and shoes back on.  From out side the stall it would look like I
was wearing shorts.  Next I stood up to attach the garter belt, then each
of the stockings.  My hands were shaking from the thrill of dressing in
sissy things while in a men's room at the mall.  I wiggled my bum feeling
the straps tickle me as I pulled my stockings up.  With my tall size
stockings, the straps didn't seem to be pulling as hard as with mom's
shorter stockings, but they still felt very sexy.  I was about to pull on
my panties when I heard someone come in and close the door two stalls down.
He dropped his pants and let out a grunt, and splashed into the bowl.  He
started to rustle a newspaper, which allowed me to continue.  I quickly
pulled up my panties, tucked my stiff girly cock in then took off my shoes
again and slowly put on my pants, careful not to snag my new panties when I
zipped up.  I stepped into my shoes once more then put my jockeys into the
bag and flushed.

  I opened the door and went to the sink to wash.  In the mirror I checked
to see if everything I had on underneath looked ok.  Satisfied that nothing
was showing, I grabbed my bag and started for the car.

  As I walked I could feel the nylons and panties caress me under my jeans.
This was the first time that I wore undies under my male clothes.  The
garter straps brushing against my thighs felt great.  I took my time
walking out to the car.

  Rob and Mike were in the car waiting.  I got in the back seat.  After
closing the door, Rob looked in the rearview mirror and asked "did you get
what you were looking for?"  I smiled at the mirror and said I did and
more.  I could see his eyes brighten.

  It was dusk as we drove back home.  Mike asked Rob to drop him off at his
house.  When we got to Mike's, he and Rob discussed plans for later that
night before Mike got out.  I moved to the front seat after Mike left.  As
we drove away, Rob asked me to show him what I had bought.

  First I showed Rob mom's replacement nylons.  He nodded his approval.
Next I pulled the remaining three pairs of panties and dangled them near
his face.  He was trying to look at them while driving. He said "they look
cute".  I


put them back in the bag as he asked what else I had in there.  I told him
that he couldn't see them.  When I put my things on in the men's room, I
had no plans for Rob to see me tonight.  When I put them on, it was for my
thrills only.  But I started to think that I'll tease him by showing him
what I was wearing.  He'll be horny thinking of the things I was dressed in
until we "get together" again.  "Getting together" meant him fucking me
while I am dressed in lingerie.

  I told him that he'll just have to wait for another time.  Rob kept
asking, like a kid who couldn't wait for his birthday present.  I knew he
would.  After a couple more "show me" demands from Rob, I grabbed my belt
buckle and undid it.  Unsnapped my jeans and pulled the zipped down.  Rob
was having a hard time watching the road.  His head was on a swivel trying
to watch what I was doing.  He swerved a couple times so I told him to
watch the road and I'll tell him when to look over to see.  Rob turned
looking straight forward as I lifted my hips to slid my jeans down.  Once
my pants were at my ankles, I told Rob he could look.  In the low light of
the evening he could barely see my things, so he turned on the overhead
light.  He saw everything now.  His eyes lit up, as he said "verrry nice".
Rob reached for my stocking covered thigh.  I told him to keep his eyes on
the road, that I didn't want to be found in my sissy undies if he wrecked.
Rob drove with his left hand on the wheel and his right hand on me.  I
scooted over on the bench seat, to get nearer to him for both our
conveniences.  Rob caressed my thigh at the stocking top.  He stuck his
fingers between my legs and tickled me.

  My sissy cock was stirring under my fresh new panties.  It started to
form a tent as I reached to turn the light off.  Rob moved his hand up to
my sissy cock and stroked it.  I tilted my head back and enjoyed his touch.

  Rob teased me for a while, until I decided to return the favor.  This was
going farther then I could have planned.  I reached toward his zipper and
pulled it down so I could get a hand in.  Rob told me to undo his belt and
jean button.  After getting the belt and pants open, Rob lifted his hips
off the seat.  I tried to get his jeans and underwear down but we came to
an intersection.  Rob had to sit to use the brake pedal. After we got
through, I slid his pants down to his thighs.  I stroked his warm hard cock
as he drove on.  Our arms were crossed as each of our hands groped the
others cock and balls.  Mine covered with my pink panties, his naked to the
world.

    I wasn't paying attention to where we were going, but it seemed to be
taking longer then usual to get back home.  I looked out the window and saw
fields.  We were not going home I though.  We were going out of town.  I
asked Rob where we were going.  He said that he knew a place where he takes
girls parking.  I got excited knowing what Rob had in mind.

  I kept playing with his cock as we pulled into a dirt road.  We drove a
short

distance before Rob turned off the headlights.  We slowly drove up next to
a group of trees just off the road.  Rob told me to get out.  I had to get
my pants and underwear off before I could step out.  I put my shoes back on
and got out.  We quietly closed the doors and Rob walked to the front of
the car.  He was holding his jeans up with one hand.  I was standing
outside in my panties and stockings with the feel of a cool breeze passing
through my legs.  I was getting a chill from the evening air and my
excitement.  Walking towards Rob, he let go of his pants.  They dropped to
his ankles leaving his hard cock bobbing in the early evening moonlight.  I
leaned down and gave its head a kiss and a lick.  Rob put a hand on the
back of my head, forcing me to take more of his length.  I didn't need to
be forced I was willing to suck him.  He then grabbed my shoulders and
tried to push me down on to my knees.  I resisted that, I wasn't going to
ruin these nylons too.  I pulled off his cock and told him that I wouldn't
kneel in the dirt in my stockings.  Rob kicked off his jeans, hopped on the
fender of his car and spread his legs open.

  I walked up to Rob, put a hand on each thigh and pushed my nylon covered
cock up against his balls.  I stood on my toes as my sissy cock slid under
his balls and up along his shaft.  We kept our faces back away from each
other.  We've never kissed on the mouth and we had no urge to do so.  Ours
was strictly a sexual thing, not emotional.

  A few more up and down rubs with my slick panty covered cock head and I
was ready for more.  I pulled back with my hands still on his legs, bent
down, and kissed Rob's sack.  I flicked my tongue over his cock head,
licking the precum off its hole.  My warm saliva in the cool air formed
wisps of fine steam rising from its head.  I began to finger his ball sack
but noticed that it wasn't soft and bouncy as in the past.  It had
tightened from the evening air.  I then completely swallowed Rob's stiff
pole to his pubs.  I worked my mouth down his shaft like I was hungry for
cock, and I was.  Here I was, standing outside in my stockings and panties,
leaning on to a car, sucking a hard cock.  I was horny as hell.  In the
dark of the night, I felt like a girl on her first date.  I knew now what
it was like for a girl to be parking with a guy and have her face buried in
his crotch. I was more willing to go all the way than most girls would.
Unlike girls, I had no fears of getting pregnant.  I was expecting to go
all the way now.  I would have been crushed if we didn't fuck tonight.  As
I bobbed on Rob's shaft I thought how quickly my plans for tonight had
changed.  I was planning to go back home, wearing my panties and watch tv.
But now I was going to get my bum filled with gooey cum.

  After what seemed to me to be a short period of time, Rob said to stop.
He grabbed my head to keep me from going down on his pole.  I tried to
continue but Rob slid off the car.  I kept my mouth locked on his cock, but
had to let it go.  As I stood up straight I saw Rob, naked from the waist
down,


walk to the back of the car and opened the trunk.  I couldn't see what he
was doing until he closed the lid and headed toward me.  He had a blanket
in his hand.  No doubt he had fucked girls on it when he brought them out
here.  I waited to see where he would spread it out.  I figured he would
lay it under a tree.

  Instead of laying it on the ground, Rob laid it on the car fender and
hood.  After smoothing it out he told me to lean over on to the blanket.
The fender was flat, perfect for being bent over on.  I stepped to the car
with a smile knowing I was going to enjoy this.  I was still wearing my
male shirt, but everything from the waist down was female.  As I leaned
down on to the hood, it was still warm from the engine inside.  I teasingly
grabbed Rob's cock as he stood beside my hips.  I released it as I laid
flat on my tummy waiting for his next move.

  My nylon covered bum was sticking out waiting for Rob's attention.  He
stepped behind me and placed his hands on my hips.  He leaned into me
poking his cock into the crack of my pantied ass.  He told me to spread my
legs wider apart.  I adjusted my feet, allowing him easier access to my
butt.  He stepped closer, his cock head up against my ball sack.  His hands
began to rub and caress my cheeks, sending shivers up my spine.  Goose
bumps rise up on my thighs and bum.  Rob ran his hands down and around the
front of my hips, between my bare thighs, down to the tops of my stockings.
Rob kept his cock tucked up under my ass, against my balls.  I was in
heaven.  He leaned back to allow his cock to spring up and press between my
cheeks.  He worked his shaft over my nylon covered hole. Teasing my pussy
by poking its head into my entrance.  When I couldn't take anymore, Rob
patted my cheek, stepped back and walked to the driver's door.  He leaned
in through the window, fumbled for something, than came back over to my
wanting ass.  I turned my head, watching what he was doing.  I saw a tube
of some kind of gel in his hand.

  Rob hooked a finger on to a leg band of my panties and pulled to one side
exposing my rose bud to him.  I could feel the cool of the evening air rush
over my pussy hole.  I felt tighter then ever now.  Rob reached under to
free my balls and cock.  My girly cock was forced up against the blanketed
fender.  My whole four and a half inches was trapped against the car.  I
had little chance of impressing the girls with my sissy cock.  Maybe my
future was with the boys I thought.  I reached one hand back to my bum and
took the silky material from Rob's hand.  I pulled as far as the panties
would stretch.  I knew he would need both hands for what was coming.

  Letting go of my panties, Rob opened the tube of gel.  Squeezed some into
his hand, then place the tube beside my hips.  He rubbed his hands together
spreading and warning the gel.  Instead of smearing my ass hole with the


gel, he reached between my legs.  Rob wrapped my cock with his slick
fingers, rubbing up and down its stubby length.  I had to catch my breath.
I had not expected him to do that.  I loved what he was doing but I wanted
my ass packed.  I wiggled my hips and told him that I was fine.  It was
nice of him to give my cock attention, but what I really wanted was for him
to fill my asshole now.

  The juice in my balls were boiling up but I could take care of that later
myself.  I wanted to get to the fucking.  The building anticipation was
driving me crazy.  Rob stopped his fingering of my cock and balls then
squeezed more gel in his hand.  Warming the gel in his hand again, he
placed his gooey covered palm against my hole, wiping most of the gel into
my pussy entrance.  His left hand moved to the small of my back.  He
grabbed the garter belt and waistband of my panties together.  Rob pulled
on them like the reins of a horse, using them to control me, to keep me
from moving away.  He should have had no concerns for that, I was anxious
for him to start fucking me.

  The first finger of his right hand began to probe around my butt crack,
trying to find my rose bud in the dark.  When he located my hole, he
wiggled the tip in an inch or so.  I waited for the pain to hit.  With so
much lube, it wasn't too bad.  Being the fourth time that Rob had invaded
my tender pussy with his fingers, I was relaxing easier.  I knew what to
expect.  His opening of my pussy was becoming familiar.  I did need to be
stretched to accept his six inches of boy bone.  With more pressure, his
finger slipped through with little resistance.  He held it in a few seconds
then pulled out.  With his left hand holding me steady, he added a second
finger to my opening.  Both gooey digits slid in with no pain.  I was
feeling pretty good at this point.  I thought his last two fingers should
present me with little trouble.  Rob added the third finger at my opening.
Instead of him pushing them forward, I pushed back sinking them deep
inside.  This time a twinge of pain ran through my hole.  It quickly passed
and I ground my pussy into his hand.  I slid forward on the hood as Rob
worked his fingers in and out until I was quite loose.  Rob placed all four
fingers in my pussy, I swallowed them with ease.  Rob asked if I was ok.  I
let out a low moan of "ummm hummm" into my free hand that my face was
resting on.  I wiggled my bum letting Rob know that I was fine.  Rob
twisted his hand around in my pussy.  I could feel him tickling my innards.
I squirmed my ass in satisfaction.  I wanted his male meat in me.  I told
him that I was ready.  He pulled his fingers out and patted my bum
tenderly. I felt a brush of cool air at my entrance when his hand was
removed, sending a shiver up my back.

   I could hear Rob greasing his cock in preparation for reaming my ass.
He smeared more gel at my hole.  Rob's left hand was still holding onto my
sissy undies.  His grip was firm but not forceful.  I was still holding my



panties off to the side, at least until his cock entered my pussy.

  Rob wiped his gooey right hand on my panties, then placed his cock head
against my slick pussy hole.  Holding his boy bone steady until his head
would pass through.  His hips snug up against my bum cheeks.  His thighs
wedged inside mine.  Rob was ready and so was I.  He rotated his hips
forward pressing the tip into my hole.  It slipped off to one side because
of the slick gel and my pussy tightening a bit.  I groaned my
disappointment.  His free hand aligned his head and held it straight while
he pushed again.  He met little resistance as his head popped into my
opening.  I had no pain so I slid back while the head tunneled inward.  Rob
pulled me farther back with his left hand.  He was deep inside, his balls
touching mine.  I let go of my panties, bringing that hand also up under my
mouth.  I let out a soft throaty moan as I ground my cheeks against Rob's
hips.  I wanted to get every inch deep inside.  The fullness I felt from
Rob's cock almost caused me to pass out.

  Rob slid me forward on the hood, as his head popped out.  It bobbed
around at my entrance.  Teasing me, taunting me.  I was ready to cry.  I
decided I wasn't going to let him torture me, so I pushed back impaling
myself on his cock.  I caught him by surprise, he didn't expect it and
didn't have time to stop me.  I told him "quit screwing around and start
fucking me or I'll get in the car".  He knew I didn't plan to stop now.
Right then, Rob could do what ever he wanted, but I would be ticked if he
didn't start poking me.

  Rob leaned into me, I slid across the fender again.  He placed his free
hand on my bare hip and held me tight.  It felt like he was deeper then
ever before.  It was probably the perfect ass fucking position, allowing
the deepest penetration.  Either that or his cock grew a little longer.
For whatever the reason, I was enjoying our best fuck yet.

  Now Rob was going to take control.  Holding me at my hip and by my
undies, he pulled three quarters of his length out then back in.  He
started a smooth slow steady sawing motion in and out of my pussy ass.  I
lad there submissively like a girl, just loving the sensations.  His warm
smooth shaft gliding on the gel, bumping his mushroom head against my
walls.  I slid a little from the blanket sliding over Rob's freshly waxed
car hood, but he didn't let me move much.  He was controlling us both.  Rob
pumped me like I was a sex toy.  He didn't care if I wanted it fast or
slow, he was doing what felt good to him.  After a few minutes of his
steady motion, he began a slight increase in his speed.  My pussy hole was
growing warm from the friction of Rob's cock.  His force was also
increasing with his speed.  He held me while he bucked in and out.  Not
moving except at his waist.  His hips barely left


my thighs.  He seemed like he could go all night, but I couldn't.  I want
him to start ramming me hard and fast.  I wanted him to shoot his load now.

    His hips rotated around, the head of his cock tapping my innards.  I
stood on my toes, trying to make the feelings even greater.  Rob slid in
and held still, he moved his feet backward slightly.  This gave him better
leverage into my ass.  He pulled partway out then in a little harder.  Rob
picked up his fucking speed times two.  I knew we were getting close now.
He began to pound me for his own pleasure.  He didn't care what I wanted.
I was just along for the ride now.  My pussy was loosely holding on to his
shaft.  He was opening me up wider as his force increased.  He began to
push and pull me to meet his motions.  I was being yanked around like a
doll.

  Rob's pace quickened to the point that I couldn't keep up with him.  He
held me firm and slammed my pussy like a dog on a bitch.  He was banging me
harder than at any time before.  As he fucked me with little mercy, I hoped
for this to end.  I wanted his cum now.  But Rob didn't care what I wanted.
He fucked me harder and faster.  His cock swelled as he grunted and
groaned.  I held my breath and waited for his shots to start.  He felt like
he was going to explode, and he did.  Rob let lose some powerful jets of
cum into my love canal.  He kept slamming me as his cock shot blasts of his
warm juice in my hungry ass.  My pussy sucked out his goo as fast as he
could shoot it.  We were both now moving back and forth, milking as much
cum as we could get out of his balls.

  As Rob's squirts of cum weaken in force.  He kept fucking as if he wanted
more.  I had enough, but it seemed like Rob want a second go at me.  His
cock wasn't shrinking much, staying hard, he got back into a steady rhythm
as if he hadn't shot a load yet.  I began to get into it again.  I guess I
got my second wind.  We were trying to adjust our motions to get in sinc
with each other.  After a couple tries, we got going again.  This time Rob
was letting me do more of the action.  I was sliding across the hood,
pushing my ass to meet Rob's boner.  His shaft slid with ease through the
mix of gel and his thick cum.  We just couldn't get enough of this tonight.
His cock felt like it belonged inside of me.

  As we pounded into each other, we heard a rustling noise behind us.  We
stopped and held quiet for a second or two, waiting to hear more noises.
That ruined the moment.  Rob said he was pulling out and I was ok with
that.  We may have had a second shot at him cumming if it hadn't been for
the noise.  I guess we were both a little more nervous about being out
there now that Rob got his first load off.  The noises may have been around
us earlier, but we heard nothing as we fucked like animals.  Since Rob got
off once we would call it a night.


  Rob pulled his semi hard cock out letting my panties slid back across my
leaking pussy.  He grabbed the elastic band and pulled it across snug,
covering both cheeks. Rob's warm goo ran down to my sack and dripped into
my panty crotch.  As he wiped his cock off with the end of the blanket he
told me "get in the car, we're leaving".  I told him I would leak in my
jeans and on the seat.  He tossed me the blanket and said I could set on
it, but we were leaving now. He said he had to meet Mike in a little while
and wanted to get cleaned up.  He pulled on his underwear and pants as I
walked around the car.  The idea of sitting in cum all the way home was not
appealing to me.  I loved cum, but not in my jeans.  Rob got in and helped
me lay out the blanket on the seat.  I sat down and reached for my pants.
Rob started up the car and began to back out.  My door was still open.  I
told him to stop so I could get dressed.  He told me to put them on while
we headed home.  I closed the door and started to remove my shoes.  Now I
knew how some girls felt after they put out on a date.  "Wam bam, thank you
mam"

  As I sat in my cum soaked panties and jeans riding home, I said nothing
to Rob.  He said nothing.  He reached over and turned on the radio.  It's
always awkward when we finished our affairs.  Not knowing what to say.  I
didn't want to sound like a fag, trying to find out what Rob was feeling.
I guess I was fine with us fucking then going our separate ways.  I didn't
want a relationship with Rob, but I couldn't even start a simple
conversation with him.  So I sat quietly figuring out how I was going to
get to my room with the stain in my jeans.

  As we pulled into the driveway I thought I would jack-off later, maybe
before I put my sissy things away in my closet.  I would wash out the pair
of panties I was fucked in tonight after the parents went to bed.

  When Rob stopped the car he told me "wash the blanket and put it in my
bed room".  I sat gathering up my things as he got out.  He stopped, turned
around before closing the door, leaned his head in and said "it was nice
tonight.  Don't get weird about it.  If you're ok with it, we'll keep doing
it until we're ready to move on.  Its not like we'll be doing this our
whole lives.  Its just for the sex".  I smiled weakly and nodded.

  We did it a few more times.  I'll write about the next time soon.