Date: Wed, 7 Apr 2004 12:04:39 -0700
From: Joan Mitchell
Subject: Rob's Sissy Boy VI

   I've had a thing for vans since my teens.  Even in my forties and now
into my early fifties, I've own a van.  I fucked my wife in a van the night
we met during a van club party.  This fondness for vans started back in the
late sixties.  Back then a teenager with a van was cool.  My brother Rob
bought a used van to drive while at college.  He figured that it would be
good to take his belongings to and from school and help get him laid.  It
did help him get laid even before he got to college.  We fucked in the van
while at a drive-in theater.

   Getting dressed in lingerie and having my brother fucked my ass was just
heavenly, I did wished the opportunities were more frequent.  During a late
night trip to Rob's room to chew on his a boy bone, the idea came to me to
use his van for an affair.  After I had swallowed his warm gooey load, Rob
said that he needed to fuck someone.  His girl would be away for a month
with her family on vacation.  I took the hint.

   I said "if you want to go parking, I up for it."

   Rob said the last time he girlfriend went to their parking spot, other
people had found the place.  A couple cars drove past them as they made out
along the dirt road.  He didn't feel comfortable going there any longer,
especially with me.

   I thought a few seconds and blurted out "how about a drive-in in the
van?"  I thought what a better place to make out at.  Besides, anyone who
saw us would think that I was a girl from a distant with my shoulder length
hair.

   Rob laid quiet for a moment then said "that's not a bad idea.  We could
go to one out of town.  Chances are no one we know will be there."

   Being it was mid-week we planned to wait until the weekend to go.  On
Thursday evening Rob found a Clint Eastwood movie "A fist full of dollars"
in the newspaper, that was showing at a drive-in about fifteen miles away.
We agreed that it would work

   Saturday finally came.  I was horny as hell.  Before I left for work in
the morning, Rob told me to be ready when he got back from his job at the
local department store, around seven.  After getting back from work at
six-thirty, I took a shower, than headed to my room to dress.  I dug out my
boxes of sissy things, and selected the items I would be wearing.  I was
going to wear my lavender outfit.  A bra, garter belt, black stockings and
panties.  I also picked a pair of white satin panties for Rob.  He didn't
know it yet, but I planned for him to be wearing panties tonight also.
Before I began to dress, I checked to see where my parents and younger
brother were.  I didn't need anyone walking in on me as I putting on my
girly undies.

   First came the bra.  I reached thru the arm straps and hooked the bra
behind.  I quickly put my male shirt on over it.  Next I stretched the
garter belt around my waist and attached the two hooks.  I was getting
pretty good at hooking stuff behind me now, then the panties.  I stepped
into the leg holes and slid them up over my sissy hard-on.  I pulled the
stocking claps thru the leg openings.  Sitting down on the bed, I carefully
worked the stockings on up to my knees.  I stood up and stepped into my
jeans.  If anyone came in, I could yank the jeans up and cover my undies.
Gently pulling the tops of the stocking up my thighs, I connected each to
the straps.  There was that tug of the stockings that made me feel so sexy
that I wanted to prance around wearing only them.  I love garter belts and
stockings the most.  The way they frame my cock, balls and ass it's so
sexy.  I

   I reached for a pair of socks to put on to cover the nylons that would
show above my shoes.  Suddenly my door opened.  I panicked, dropping the
socks and started to pull up my pants.  With the jeans half way up my legs,
Rob poked his head in the door.

   Rob said "Good, I was hoping I would catch you getting dressed."

   I said, "You bastard, I thought you were mom or dad.  You scared the
shit out of me."

   He laughed and said, "Sorry, I wanted to make sure you had on your
lingerie tonight.  I asked him if he approved.  Rob said, "It's perfect.
See you in the van in about a half hour."

   Rob had little to be concerned about.  Wearing women's lingerie was my
true motivation for letting him pound my bum.  If I were not wearing my
panties, garter belt and stochings, I don't think I would have been as
willing a partner.

   After Rob left, I finished dressing, filled my bra cups with white
nylons, then stuffed Rob's panties in my pocket.  I headed to his room to
catch him before he took a shower.  As I stepped into Rob's room, he was
gathering his clothes.  I closed the door.  He asked me what I needed.  I
pulled out the panties and tossed them to him.

   He caught them then asked, "What are they for?"
 
   I told him "wear them tonight."

   He said " What? Hell no.  I'm not the one who's into girls underwear."

   I said, "If you don't, we may as well not go, because we're not fucking
unless you're wearing them."

   "What the hell is this about?"  Rob demanded.

   I said "Just please put them on this once."

   This was the first time that I had put any conditions to Rob of our
affairs.  Rob sensing I really wanted this and the fearing not getting laid
tonight, he thought for a few seconds then said, "Alright, you bitch.  I'll
wear them this once.  You've blackmailed me in to it.  But I'm not doing
this again.  And don't try any weird shit tonight, like trying to fuck me."

   I smiled saying, "Thanks, I hadn't thought of that.  That's a good idea.
We both would be virgins at that."  He gave me a stare of discuss as I
turned and left his room.  Little did Rob know, that's exactly what I was
planning to do.

   While Rob showered and dressed, I grabbed some pillows, blankets and a
towel then went out to put them in the van.  I figured some cushioning on
the floor of his van would be needed.  He had laid some carpeting on the
floor but it would still be hard on the knees and ass without more padding.
Rob also had two large beanbags in the back.  With only the two captains
chairs up front, he had them for whoever else needed a seat.  After I
stretched out the blankets and tossed the pillows around, I got in the
passenger seat and waited.

   About ten minutes later Rob came out of the house with a blanket and a
couple pillows in his arms.  I chuckled as he opened the side door and saw
what I had already done in the van.
   
   He tossed his things in saying, "Looks soft enough to fuck on."

   I said "If you're dressed for it."

   Rob snapped back "Don't worry, I'm wearing them."  Then he went around
and climbed in the driver seat.

   I looked straight ahead and said "Don't they feel great against your
cock?"

   He said, "I'm as hard as a lead pipe.  You'll pay for this.  I'll fuck
you raw tonight."  I snickered as he backed out the driveway.

   I tried not to sound like a fag as we tossed sexual insults and jabs
back and forth during our ride to the drive-in.  I was so excited I
couldn't wait to get stripped down to my panties.  As we got close, Rob
said that we would wait until the movie had played a couple minutes.  The
sun would still be setting when as the previews played and the movie began.
When Rob pulled up to the ticket booth to pay, I slouched down a bit.  I
avoided looking at the guy selling tickets.  After paying, Rob drove along
the back row and parked at the far end.  Before he placed the speaker in
the window, Rob asked if I would get something from the snack bar.

   I said, "If anyone sees me, they'll know that there's two guys in the
van."

   We were trying to avoid that, because when the windows fog up later,
people would figure out what was going on.  He agreed that I would stay in
the van and he would go.

   When Rob got back with the popcorn and drinks, he said he saw a couple
cute girls at the snack bar.  They were wearing halter tops and hot pants.
I asked him why he didn't ask them back to the van.

   He said, "I was, but if they didn't put out, we would both be going home
hornier than we already are.  Besides I know I'm going to get some, so why
take a chance and lose that opportunity."

   I smiled a shitty smile and said, "That's true."

  A few minutes later they began showing the previews and advertisements.
The sky behind the screen was pink as the sunlight disappeared.  I was so
horny from the anticipation that I reached over to Rob's crotch before it
was completely dark.  I made small circles over his hard cock pressing
against his zipper.  He then reached and fondled me through my shorts.  I
stopped teasing him and undid my jean button.  Then Rob helped pull the
zipper down.  I was relieved to finally have my cock freed of its confines.
My little sissy cock was poking up just past my opened pants.  Rob slipped
his hand in and stroked my lavender wrapped shaft.  I lift my hips up and
pushed the jeans down over my thighs to my knees.  I kicked off my shoes
and leaned forward to push the jeans off my feet.  Rob was forced to remove
his hand while I worked my pants off.  Now I was sitting in my garter belt,
stockings and panties feeling very naughty.

   As he reached again for my little dickie, I told him, "Take off your
cut-offs."  I wanted to see that he did put on the panties.

   He asked with a grin, " Don't believe me?"

   I said, "Drop 'em."
   

   Rob undid his belt and snap.  I pulled on the zipper as he spread his
shorts open.  With his zipper open, my fingers slithered in.  I let out an
"aaaaah" when I touched his satin wrapped shaft.  I slip my fingertips up
to its head and teased it until Rob rose up and took his shorts off.  Rob
nervously looked around the van to see if anyone was near by.

   I said, "Relax, no one cares what we're doing."

  We sat back in our panties and watched the movie begin.  Our arms crossed
as we caressed each other's boy bone thru the satin material.  Rob said
that he was still not comfortable.  He felt exposed.
  
   I said, "Well, go to the back and sit."

   Rob nodded a yes, turned the captains chair around, slide out and onto
his knees.  My hand didn't leave his crotch until he crawled away.

   The windows at the side and rear doors were covered with curtains.  Rob
had put them up after getting the van.  There was soft light that shown
through the curtains.  It was just enough to see as we moved around.  Rob
moved the bag so he could see the screen then sat in it.  I turned my chair
to face him.  Stretching out my legs, I placed a foot on either side of
Rob's hard boner.  I could rub his shaft with my stocking covered feet.  I
teased him with my toes for a few minutes until I couldn't stand it any
longer.  I slid out of my chair and crawled towards him.

   Rob said, "I don't like the front window not being covered.  I feel
exposed."

   I grabbed a blanket and looked for a place to hang it from.  I didn't
find any place to attached it so I threw it over the chair backs.  It
covered the lower part of the windows from view.  I looked back to Rob and
asked him if that was ok.

   He said, "That's better."

  I crawled to the back and sat between Rob's legs facing him.  As I lifted
up his legs to my shoulders, he asked me what was I trying to do.  I told
him to relax and enjoy himself.  I crawled on my knees until my sissy cock
was laying down against his stiff shaft.  Two layers of satin separated our
cocks.  I leaned against his legs and began to dry hump his dick.  Our
cocks twitched and squirmed as mine glided smoothly along his.  I worked my
head into his sack and the sensitive spot behind, just in front of his bum
hole.  Rob moaned as I poked and rubbed until I was ready to shoot my load.

   Rob pushed me away with his legs saying, "That's enough, or I'll blow
any second.  Then neither of us will get what we came for."

  I reluctantly agree then backed up and crawled to the other bag.  I
pulled the other beanbag over beside Rob.  Took off my shirt, exposing my
bra.  I was now ready for our night at the movies.  I helped Rob take off
his shirt and he settled back.  The bag cradled Rob's backside, his legs
bent up slightly.  I reached between them and rubbed his cock and balls
thru the satin.  Rob let out a low "ummm" as he rolled his head back.  I
leaned over, my mouth above his tummy. Then I began licking the top edge of
his panties.  As I blew my warm breath down over his cock head, Rob reached
behind his bag and brought out a bottle.  He twisted off the cap and told
me to hold out my hands.  It was perfume.

   Rob said, "This will make you smell like a girl."

   I wasn't insulted.  I thought it was a great idea.  What a better way to
feel more feminine?  I cupped my hands as Rob poured a generous amount out.
Most of it I caught, but some leaked onto my thigh.  After he stopped, with
my hands held together, I drizzled some onto my tummy.  It ran down to my
garter belt and pooled in my belly button.  I cupped the remaining perfume
in one hand and dabbed my other hand in.  With my damp fingers, I reached
behind to my bum and rubbed across my cheeks under the panties.  The last
small amount remaining was rubbed between my palms.  I patted my hands onto
the front of Rob's panties.  The stale van air was now filled with the
sweet smell of a woman.  I felt so sexy that I buried my face into his
crotch.  I kissed and nibbled on Rob's shaft like a nympho.  After a few
minutes rubbing my face along Rob's length, I reached in to his panties and
pulled his cock out.  I devoured him in one quick motion.  I was moaning
from the pleasure I felt with Rob's lovely hard cock in my mouth.  Rob
tapped my waist to indicate for me to swing my hips around towards him.  I
did a pivot while still holding his boy bone between my lips.  Now I was at
a slight angle with my head down, buried between his arched legs.  My ass
was near his shoulders.  Rob reached between my legs and up to my sissy
cock.  As his fingertips tickling my balls, my girly cock twitched inside
their satin wrap.

   During most of our affairs, Rob was willing the lick me while I sucked
on his pole.  Not quite a sixty-nine, but close.  So I hoped he would do
some oral teasing tonight.  I raised my leg up over his head and straddled
his face.  Rob slid my panty crotch to one side, releasing my four and a
half cockett and sack.

   I wanted to suck the salty cum from his balls.  I was so horny I didn't
want anything to stop me.  But Rob did.

   He told me "slow down, we've got plenty of time."
  
   I mumbled "Not long enough."

   I would've loved to swallow a load now, then take a load in my ass
pussy.  But the movie wasn't going to last that long.  I figured I better
ease up before he shot his one load of the night.  I wanted my bum filled
more then my stomach.  I began to lick his head and balls as I caught my
breath.  Rob flicked his tongue around my cock teasingly.

   Rob shifted in the bag reaching beside it.  Pulling out his jar of gel
and opened it.  Once his fingers were coated he smeared my rose bud and
began to poke inside.  I rested my face against his rod as I waited for the
burning to pass.  His first finger entered easily so he added the second.
I loved him diddling at my pussy hole.  I was going to do it to him.  I
knew he said, not to try anything weird, but I wanted to see what he would
do or say.  I dipped my hand in the gel, then over to his bum.  I carefully
exposed his entrance while he was distracted with stretching me open.  I
gently placed a gooey finger at his hole.  With light pressure, pushed the
tip in.

   He buck and asked, "What the fuck are you doing."

   I said, "Lay there, shout up and relax.  Just keep doing what you were
doing."

   I wanted to do this whether he liked it or not.  I think he was curious
about how it felt but didn't want to sound like a fag asking for it.  So I
eased my finger in an inch at a time.  When I felt resistance, I would stop
then wait a few seconds.  His hips moved about and he grunted a bit but
didn't protest again.  I asked him how he was doing.

   Thru his panting, he said, "It takes getting use to."

   Rob had laid back with his two fingers still in my pussy, concentrating
on my finger at his virgin hole.

   When I got the first one in completely, I said, "If you don't keep
stretching me, I'll have you ready first."

   He snapped out of his trance and pushed the third finger in with little
finesse.  I was pushed forward from his force.  I slipped my finger out and
added another.  He was taking it better then I had expected.  A couple
grunts, but he didn't resist.  Rob had all four fingers inside me before I
had started on my third.  I needed to get him to take at least three
fingers to accommodate my girly cockett.  So as my third finger disappeared
in his bum, I now had to somehow get him to allow me to fuck him.  I wasn't
sure if he was going to go along with that.  Holding my hand in his bum, I
gave his cock some attention.  Kissing and licking along its length, trying
to get him in the mood to accept my next move.

   Without warning, I rolled off to one side.  As I twisted away, Rob kept
his fingers in me.  I Crawled away from his hand, still with mine in his
ass hole.

   He asked, "Are you ready?"
   
   I said, "Yes, roll over."

   Rob said, "What do you mean, me roll over?"
   
   I said, "I want to fuck your ass."
   
   He protested, but I told him, "Come on, I'll be gentle, besides you'll
probably like it once you've try it."  Like I said, I think he was willing,
but he didn't want to give in too easily.  After some more half-hearted
complaining, Rob got up.

   As he started to turn over in the bag, he said, "Just this one time and
don't breath a word to anyone."

  I said, "Oh yea, like I'm going to go around telling people that I
screwed my brother.  We're in this together, so to speak."

   I told him to shape the bag so he could drape himself over it.  As he
leaned over the edge, I wiped some gel all over my cock.  I couldn't wait
to fuck him.  I crawled up behind his bum and stretched his panties to one
side.  He wanted to take them off but I talked him into keeping them on.  I
caressed his satiny cheeks as my nob touched his puckered hole.  I had a
glob of gel at the tip to help grease the way in as I pushed.  I asked him
if he was ready.  Rob let out a mumbled, yes.  Placing one hand on his
satin covered hip, I took a deep breath.  I put the other hand on my shaft
to keep it straight, then leaned into him.

   I was shaking from the anticipation, my first fuck.  I almost
hyperventilated.  As I pressed into his warm slick bum, I tried to calm
down.  I felt him resist as the head pushed thru.  I held still allowing
him to adjust.  I wasn't big at all.  It wouldn't hurt too much as I
slipped thru.  Rob slid forward across the beanbag as I pushed in again.
His "O" muscle at the entrance was tight around my shaft.  I was about to
ask him if I should continue.

   Before I could, he whispered, "Keep going, I'm ok."

   I pushed my hips forward, burying my sissy cock to its base.  My
stockings were rubbing against his cheeks.  I couldn't believe it, my dick
was completely inside.  My cock twitched as I held tight onto his hips.
Rob let out a gasp.  He was taking it better than I could have hoped.

   Rob whispered, "Get started before I change my mind."

   I figured I was now in control and wanted to drive him crazy like he did
to me.  But I just couldn't wait any longer.  I pulled out, than slid back
in.  I could tell that I wasn't going to last very long.  I was so excited
about finally fucking, that my senses were over loading.  I rotated my hips
in and out a couple times then felt my boy juice boiling up in my sack.  I
wanted this to last a few more strokes, so I stopped and fought the urge to
release my load.  I was able to hold it off, but not for long.  I told Rob
to get ready, I was going to shoot soon.

  He mumbled, "Fuck me!  Just fucking shoot.  I can't take anymore."

   I took that as he was ready too.  I had to be careful not to pull back
too far or I would pop out, that would have driven us both nuts.  I started
to slide in and out quicker.  My pace was at three quarter speed.  It was a
wonderful feeling.  My cock was on fire.  My leg and stomach muscles burned
from this new type of workout.  I wanted to fuck all night.  But sooner
then I had hoped, I lost control.  My hot cum shot up from my balls, thru
my cock, splashing into Rob's bum.  It was a very sexy feeling, to blow my
load inside of someone.  To shoot deep into a warm wet place.  Rob would
suck me but never kept me in his mouth to cum.  It was always out in the
open when I released.  This was like nothing I had felt before.  I
continued to bounce my thighs off his cheeks a few more times.  Milking out
as much of my juice as I could.  Rob laid groaning and sweating.

   I slumped over on to his back.  Spent from the new experience.  I hadn't
ever done that much work while being fucked.  At that point, I wasn't sure
which I liked better.  Fucking someone and doing all the work, or being
fucked and let someone else wear themselves out.

   He laid still as I planted soft kisses on his neck and shoulders.
Sensing a gay moment, he said for me to get off.  My dickie had slipped out
before I moved.  I rose up and pulled back.  My cockett shrank like a
turtle into its shell.  I rose up and moved back away from Rob's leaking
bum.  Grabbing a towel, I wiped off the goo that ran down the crack of his
ass.  I mopped Rob's tender hole until he rolled over and took the towel
from me.

  As he cleaned himself, he said, "Grease up, cause you're going to pay for
that."

   I asked him, "How'd it feel."

   He snapped back, "Ok, but I feel like I have to crap."

   I chuckled a bit then scooped some gel in my hand.  First I smeared gel
on Rob's still hard cock.  It seemed strange to me that he was hard.  I
usually lost my stiffness when I was being fucked.  He must have been
really horny I thought to stay hard thru that.  Either that or he enjoyed
being screwed in the ass.  When he was good and slick I stuck the remaining
gel in my bum hole.  I was a little tight but it would be ok.

   I wiped off my hand and crawled onto the bag.  When I was about to lean
on it like Rob had done, he said to lay on my back.  I sat down, squirming
my bum around to get into a good fucking position.  Rob, on his knees,
moved in between my legs and raised them up.  With one hand, he reached for
my panties to pull them off.

   I asked him, "What are you doing?"

   He said, "Take them off.  I don't want them to get in the way."

   I did as he said and slipped them down off my hips.  Rob had left his
panties on though.  As I worked mine up one leg and over my foot, he rolled
me back into the bag, pushing against my extended stocking legs.  My legs
were up on his shoulders.  Rob couldn't wait for me to take the panties off
completely.  Here I was again with my panties, hooked on one foot swaying
in the air.  Rob's cock head bobbed around my hole.  It smeared gel all
over my balls and ass cheeks.  My bum was at the perfect height off the
floor.  He didn't have to lean over to slip in. He pushed forward, his cock
head poked past my sphincter muscle and sank deep inside.  I grunted and
sighed as his shaft filled me.  Rob stated to saw in and out at a steady
rhythm.  My eyes were closed. I laid back enjoying the cock that was
pounding my pussy.  While semiconscious, and being thoroughly fucked, I
thought how I would sleep well afterwards.  He picked up his speed,
slamming into my ass pussy.  I moaned and whimpered like a girl.  I loved
to be pounded in my ass.  The taboo of two guys having sex was a rush.  I
would love to fuck a girl, but I knew I also would want to be fucked too.

   Rob's strokes were starting to become irregular.  He was getting close
to releasing his load of goo.  I suddenly rolled sideways off the bag.  Rob
was completely surprised by my move.  His hands still held my caves, but
his cock was out of my pussy.

   He mumbled, "What the fuck are you doing now?"

   As I twisted on to my knees, I crawled back on the bag.  I said, "I want
to finish doggie style.

   Rob said nothing as he re-entered my ass.  His head would reach farther
inside in this position.  I hugged the bag as Rob rammed me hard and fast.
It would only be a short time before he released his milky cum.  I was
biting the bag to keep from squealing like a sissy.  I was ready for him to
fill me.

   I pushed back as Rob tensed up.  I felt the first blasts of his juice
splash inside.  I held my ass up to accept all of his hot cream.  He was
trying to keep fucking but the shots of cum threw off his rhythm.  I pushed
into him a couple times until I had had enough.  After what seemed like
minutes, Rob's pulses of cum became weaker and less often.  Then they
stopped.  Rob let out a groan then I felt him shivered while still buried
inside me.  I smiled to myself thinking of how good it was for me too.

   Rob, realizing that the credits were playing on the screen, pulled out
and leaned back on his heels.  We could hear cars begin to leave the
drive-in.  I lowered my sore bum and reached for a towel.  Rob started to
clean himself off.  He quickly wiped than began to pull on his cut-offs.
After he put on his shirt, He yanked down the blanket and got in the
drivers chair.  He started the engine and put the speaker back.

   Rob turned back to me and said, "You can dress while I drive to the
restroom.  I gott'a go."

   I finished cleaning and pulled my panties back on as he pulled up to the
building.  Rob hopped out and slammed the door shut.  I laid in the beanbag
with my eyes closed, trying to regain my strength.  A few moments later I
heard voices.  A couple guys sounded near by.

   One guy said in not quite a whisper, "Man, look in the van.  There's I
chick half naked."

   The second guy said, "No way."

   The first guy said, "Come see for yourself."

   I knew they were at the front window.  I laid still but slowly opened my
eyes to slits to see who they were.  I was nervous and excited at the same
time.  Silhouettes of two heads were at the front of the van.

   The first guy said, "Looks like she's been royally fucked.  She's lying
in her underwear."

   I slowly rolled onto my stomach to give them a view of my ass. I spread
my legs open striking a sexy pose.

   I heard, "Holy shit, look at that ass.  I might just climb in and fuck
it myself."

   The other guy said, "Not before me."

   Seconds later I heard Rob say, "Hey, Jim, Mike how'ya doing."

   Jim said, "Rob is this your van?"

   He said, "Yea, why?"

   Mike said, "Looks like you got lucky tonight."

   Rob laughed and said, "More then once."

   Both guys let out groans and laughed.  I was giggling as I listed to
their reaction.

   After a little BS and more bragging, Rob said, "Sorry guys, I gott'a get
her home.  See you guys later."

   They said their goodbyes and Rob got in.  I asked him, "Were you nervous
when you saw the guys outside looking in?"

   He said, "Yes, but I also thought you might be giving them a show."

   I smiled then sat up and put on my shirt.  As he drove out of the
drive-in lot and we headed home, I got in front seat and finished dressing.
We said little most of the way home.  Rob turned the radio on to break the
quiet.  I was spent and he had to be also.  We left the van as it was, a
mess, and went in the house.  Without saying a word headed for our rooms.

   That was our only trip to the drive-in.  We had one more affair before
Rob left for college.  I'll write about it soon.