Date: Mon, 10 May 2004 08:16:35 -0700
From: Joan Mitchell
Subject: Rob's Sissy Boy VII

   On the all too few occasions that my wife is out of the house over
night, I pull out the dildos, mine and hers.  I'll dress in my sexy
lingerie and play with my ass.  She has on a couple occasions, fucked me
with her strap-on dildo or we each take an end of her double-headed dildo
and bump asses. These have been the only times my sissy ass has received
any attention other than from myself since we married over twenty-five
years ago.  I do love my wife and our sex is great, but I also miss the
feel of a hard cock spreading my ass hole wide open.  During the rare trips
out of town for business, I take a bag full of lingerie and latex cocks to
keep me company in the motel room.  Since none of my dildos has a suction
grip, I have to duct tape them to a table or chair leg when I back up onto
or sit down on them.

   The first time I fucked myself was at age sixteen with a miniature
baseball bat.  It was late in the summer.  Rob was getting ready to head
off to his first year of college.  He was leaving the next week, so I was
going to let him fuck me once more before he left as my going away present.
The weekend was our last opportunity.  Our parents and youngest brother
were going to be gone visiting family, Saturday into Sunday.  Phil was
already back at college.  We had Saturday night to have our affair.  I
would later find that it was to be our last time together.

  I went into Rob's room Saturday afternoon.  He was getting dress to go
out for awhile.  I walked up behind him as he was pulling up his jeans.  I
reached around and gently pressed his cock while it was inside his jockeys,
back so he could snap and zip-up.  He asked me if I was "up for anything
tonight."  I told him I was, and to be back early.  Rob said that he would
be in around ten.  I told him I would be waiting.  He asked what I planned
to be wearing.

   I said "you'll find out when you get home."

   I walked out into the kitchen, where mom was sitting, sipping a cup of
coffee.  I asked her when they were leaving.  She said in about an hour, at
five o'clock.  Mom asked what I was planning to do tonight.  I told her I
was going to be working from five to nine, then stay home the rest of the
night.  I worked at a local grocery store after school and on weekends.
That's where I made my money to buy my sissy undies.  She asked if I knew
what Rob had planned.  I smiled inside knowing that he would likely be
fucking my ass later, but told her that I thought Rob was going to be back
early.  Mom said for us not to get into any trouble.  I assured her that we
would be good.

   I said goodbye and went to my room to get ready for work.  I decided to
wear a pair of red panties on for a thrill.  This would be the first time
that I would wear panties under my clothes at work.  I figured that the
only way anyone would know I had them on was if I split my pants.  I would
find out later that someone at work did know I was wearing panties.  But
that's another story.

   After an uneventful evening at work, we closed and cleaned up.  We were
out of the store in record time.  I just about ran the three blocks home so
I would have as much time as possible to prepare for Rob.  It was about
nine-twenty when I got home.

   After a shower, no time for a bubble bath, I dried then dusted myself
with some of mom's body powder.  I knew I would smell nice with the powder.
As I dusted myself I thought how tough could it be to paint my nails.  I
wanted to be as girly as possible tonight.  Naked, I went into mom's room
and pick a bright pink nail polish from her vanity.  With a towel around my
neck and the bottle of nail polish in my hand, I headed to my room to do my
nails.  I had never tried to paint my nail before, so I knew it wouldn't be
easy.  I placed my left hand on my thigh as I sat on my bed.  I tried hard
to be neat, but I had a few mistakes.  After finishing, I dropped the
bottle on the floor, then blew on my fingertips to help dry them.

   I now had about fifteen minutes before Rob was to be back.  Gathering up
the things that I was going to wear, I walked naked to Rob's room.  As
usual his room was a mess.  I dropped my lingerie on a corner of the bed,
the only clear spot.  Next I turned on his radio for some rock music, and
his table lamp.  Placing a towel over the shade to soften the light.  I
began to pick up most of his clothes that were scattered throughout his
room, and piled them in a corner.  Smoothing out the bedcover and prepared
to dress.

  I picked up the garter belt, placed it at my waist then hooked it behind
me.  Sitting on the edge of the bed, I rolled my white stocking in my
fingers, checking to see if the polish was leaving any marks.  They were
fine.  After slipping both nylons on, I stood up to attach them to the
claps.  This was always my favorite part of dressing.  The tug of the
stockings on the garter straps was always a big turn-on.  The straps
brushed teasingly against my thighs and bum.  What a great sensation it
was.  I picked up the pink satin camisole and slipped my arms through the
spaghetti string straps.  It was the first time that I had worn it since
buying a month ago.  I thought it felt a little snug, but it looked fine in
the mirror.  The last piece of my outfit was my tap pants.  I stepped into
them and pulled them up my stocking covered legs.  I loved the look of my
painted nails sliding my pants up to my hard sissy cock.  My boy boner
bobbed in anticipation.  I tucked my girly cock back so I could pull the
waistband up over it.  With a piece of pink ribbon, I pulled my hair
together and tied it back.  Looking into the mirror, I saw a feminized me
looking back.  I did a few sexy poses, bending and sticking my bum out
while I waited for Rob.  I was horny as hell.

  It was about five after ten when I heard the back door open, then closed
and locked.  I stepped to the bed, pulled back the cover and sheet and
jumped in.  Pulling the covers over me, I smoothed out the spread and
pulled my arm under, Rob popped his head in the door.  He saw me laying in
bed and smiled.

   He said "great, I'll take a shower and be back for my present."

    As Rob walked to the bathroom, he sang a verse of a Led Zeppelin song "
way-down-in-side--woman-you-need-me."  He sang it loud enough so that I
could hear him.  If I had known he was going to shower, I would have waited
and showered with him.  I would have soaped him up all over.  I was ready
to get undressed and join him, but decided not to.  I could entertain
myself while I waited.

    I couldn't wait to have something up my bum.  I reached my hand down to
caress my satin covered cheek.  While rubbing my bum, I noticed a miniature
wooded baseball bat on Rob's dresser.  A souvenir from a Pirate game we had
gone to.  It looked to be about the same diameter as Rob's hard cock.  I
had one just like it in my room, but his was black.  I hadn't thought of it
as a sex toy before, but I was now.  I figured, "wonder if it would fit in
my pussy hole."  I could loosen up before Rob got back.  I got out of bed,
grabbed Rob's jar of gel and picked up the bat.  I took off my tap pants,
greased up the fat end of the bat and my hole.  I leaned down, reached back
and tried to work it into my tight bum hole.  It was tough trying to get it
started in.  I needed something to rest the other end against.  I moved to
Rob's weight bench that was at the end of the bed.  Trying again, the bat
still moved around too much.  I picked up two twenty pound weights and
stacked them on the bench.  Putting the skinny end of the bat in the holes,
I could now begin to work the fat end in my pussy.  I knew I had to move
quickly if I wanted to be in bed when Rob got back.  I took a deep breath
and pushed down on the slick bat.  My bum hole gave way and the bat began
to slid inside.  I got it in an inch of two, then the burn hit.  I was bent
over while leaning back on the bat.  I had to stop for the pain to pass.
The bat felt bigger then Rob.  It did not have any give, like Rob's rubbery
cock does.  I thought, "this was the first time I had a real woody in my
ass."  I pushed down some more forcing a couple more inches in.  I wiggled
my bum around, the bat was gripped tightly by my muscles.  I reached back
around and grabbed it as it came out of the weights.  Pulling and pushing
it a couple times, I loved the fullness.  A few more pumps and I felt loose
enough.  I was running out of time.  Pulling the bat out, I tossed it onto
the piles of clothes.  I would clean it later.  After a quick wipe of my
bum with the towel, I pulled my tap pants on and jumped back in bed.
 
  I relaxed a bit, then heard the bathroom door close.  Rob was heading
back, singing his song again.  I checked the room to be sure that
everything was in place.  Rob opened the door and walked in naked.  His
six-inch cock was as hard as the bat that had just fucked me.  He had a
towel around his neck, which he laid on the bed.

   Rob said "I want my present now."

   I asked him to turn the radio down lower.  After he turned away, I
flipped the covers up over my body, exposing my pink satin outfit.  As he
turned back around, I said "here it is."  Rob stood looking down at me
smiling.

   He said, "that's what I was hoping for."
   
   I told him, "there's more once you unwrap it."

    I reached out and grabbed his boner and pulled him to the bed. Rob got
in bed and laid down on his side facing me.  His hand reached out and slid
along my satin cover hip and bum.  Rob ran his hand down below the leg of
my tap pants onto my bear thigh and tops of my stocking.  The sexy feel of
my body when I dressed in my sissy lingerie, drove Rob crazy.  He caressed
me. His hand slid along my satin wrapped body.  I laid my head on the
pillow and closed my eyes for a minute.  I loved the attention Rob was
giving me, but this was his night.  I wanted to pleasure him tonight.

   I grabbed the covers and sheet and pulled them up over us.  Ducking my
head down under the covers, I slid down the bed until my face was at his
waist.  With a hand on his hip, I pushed him onto his back.  As I did I
sucked his cock into my mouth.  I adjusted my position as he rolled back.
With my mouth locked on his pole, I twisted around with my bum towards
Rob's head.  I straddled my arms over his hips.  My face hung over his
balls.  My nose poking his sack as I lowered my lips along his shaft.  I
would, after a few bobs, nuzzle his cock against my cheek and nose.  Tuck
my nose between his sack and thighs.  I loved to rub my face in his crotch,
especially after he had showered.  Rob smelled fresh and clean.  I lapped
along his shaft.  Teasing him by flicking my tongue at the underside of its
head.  Then licked the drops of pre-cum from its tip.  The tip of my tongue
wiggling into his cock hole.  I nibbled on his rubbery head.  Lightly
scrapping my teeth across its spongy flange.  Then I got carried away and
began to nip at his helmet head.

   Rob lightly slapped my head through the covers and said "Christ, take it
easy, you're gon'a draw blood."  I mumbled an "ok" as my mouth slid down on
to his cock.
       
   I went back to sucking Rob's tasty cock.  Dressed in my outfit, bobbing
under the covers, I felt like a real slut.  I did a slow, easy motion on
his shaft.  As I swallowed his boy bone, Rob placed a hand on my bum.  He
began to make small circles over my satiny cheek.  I wiggled my bum
slightly, showing my approval.  He continued his caressing, slipping his
hand down between my legs, along my stocking, to my knee.  When he brought
his hand back up along the inside of my bear thigh, they tugged on the
garter strap.  His fingers slid in the leg opening up to my balls.  He
diddled my sack.  Rubbing and tweaking my bag and balls.

   I stop my attention of Rob's cock and lowered my face into his crotch.
My focus was now on what Rob's fingers were doing.  After a few seconds of
nuzzling his sack, I resumed my mouth fucking.  I was as horny as I had
ever been.  I gobbled his boner like a starving man eating a hot dog.  He
would lift his hips off the bed at times, trying to force more of his cock
down my throat.  I sped up, then slowed down my sucking, building his
anticipation.  Rob's hand moved from my sack to my sissy cock.  His fingers
wrapped around it, sliding along its stubby length.  Rob wasn't into guys,
but he knew what felt good.  He tried to give me some pleasure.

   We each continued to service the other.  Rob, slowly jacking me off,
while I stuffed his cock into my hungry mouth.  Rob's hand then moved away
from my aching sissy cock.  His body was shifting around, twisting onto his
side.  I could hear him reaching for the jar of gel.  I figured he was
going to finger my bum hole.  Once he had a hand full he laid flat again.
Rob's hand slid back under the covers.  I waited for his fingers to start
poking at my hole.  Instead, his gooey finger wrapped back around my boy
clit.  It was cool but nice.  His fingers lightly slid over my cock.  It
wouldn't take much for me to blow my load.  I was working his cock faster
with my mouth.  His point of release was also approaching.  I wanted his
first shots of the night to be in my mouth.  I hadn't expected him to pump
me to climax.  But now I wanted us both to explode at the same time.  Rob's
jacking on my cock had me at the edge.  I sucked him faster and deeper, his
moaning began to grow lower and more often.  His stroking of my clit was
getting irregular.  I knew we would both be shooting soon.  My tongue
rubbed his cock head, coxing his warm sticky cum out of his sack and down
my throat.  My juice started to boil.  My sissy balls began to pump out my
sticky cream.  Goo shot onto his fingers and hand.  Meanwhile his cock
erupted inside my mouth.  Jets of thick, salty cum filled my cheeks full.
I let out a low "ummmm" while swallowing as much as I could.  Some oozed
out the ends of my mouth.  I would clean the drips up later.  My blasts of
boy juice coated his hand and the crotch of my taps.  That was ok, I
planned to take them off once Rob finished feeding me his seed soup.  As we
both emptied our balls, our tempo slowed a bit.  He kept stroking my clit,
draining the last of my juices out.  I tightened my lip grip on his shaft,
sucking out as much of his cum as I could.

   We were both drained and satisfied.  But I wanted Rob to stay hard for a
second round.  I kept my mouth on his semi-hard cock.  Using a soft grip, I
slowly slid along his length, moaning as I bobbed up and down.  Rob had
released his hand from my sticky cock.  He wiped his hand clean, while I
reached back with one hand to work my pants off.  I got the pants partly
off my hips.  Rob brought his hand back under the sheets to my ass.
Sensing my intention and difficulty doing it, he took hold of the waistband
and helped pull them down to my knees.  While still wet from cum, Rob
carefully slid the pants along each leg as I lifted up to get them off.
Once they cleared my legs, Rob tossed them onto the floor.  I felt naked
even under the covers.  Rob used the towel to tenderly wipe my cock and
sack clean.
  
   With Rob's cock still in my mouth, we laid still for a few minutes,
enjoying the afterglow.  But now I wanted to get fucked.  I started to work
on getting his cock stiff again.  I slowly bobbed my head on his shaft.
Rob thought we were done.

   He asked me "aren't we finished yet?"

   I mumbled "no" into his cock head.  "That's only half of you gift", I
said with half of his cock still in my mouth.  I continued to pump his
shaft with my lips.  My one hand lightly rolled his sack in my fingers.

   Rob said "I'm up for what ever you have in mind."  I told him to "grease
up my pussy."  He reached for more gel, than began to smear it over my rose
bud.

   Rob poked a finger in, expecting some resistance.  But it slid through
with no trouble.  It felt like my pussy sucked it in.  He added a second
finger, then a third. As each was added and slid in with ease, Rob worked
them deeper.  After the fourth went in, he started to hand fuck me.
Pounding in my pussy, he forced my body forward, but my lips stayed tight
around his cock.  I was pushed from behind as his fingers drove in.  Then
leaned back as he pulled out.  I was being sodomized by his whole hand.
   
   Rob asked "you're pretty loose.  Do you think I can get my fist in?"

   I lifted off his cock and told him "Go ahead and try.  If it starts to
hurt, you'll have to stop.  Besides it might be too loose for you after."

   Rob said "that's true.  I think you're ready."

   I was ready.  I kissed his cock head as I moved away.  I threw the
covers up off of us.  The cooler air was refreshing.  Under the covers it
was quite warm, but I hadn't noticed how warm until now.  Reaching up
across Rob, placing a hand on his chest to steady myself.  My soft sissy
cock, rubbed against his cheek.  He turned his face and stuck his tongue
out, teasingly licked my head.  I intentionally took my time scooping some
gel up, giving Rob time to lap me more.  After a few seconds of Rob's
tonguing, I moved towards his cock.  With my hand full of gel, I stroked
his boy bone.  I coated his shaft and head, making it slick and shiny.
Then pumped him a few times, until he was nice and stiff.  The sounds he
was making told me he was ready.  Shifting myself down beside his hip, I
let go of his cock as I wiped excess gel on my bum hole.  With my back to
him, raised a leg up and over.  I straddled his hips, my pussy just above
his slick head.  I reached between my thighs and held his pole steady.
Slowly lowering my bum down until its greasy entrance touched his tip.  Not
wanting to wait any longer, I sank down on his cock.  My pussy swallowed
him like my mouth had done earlier.  My cheeks were pressing down hard into
his hips.  It felt like it belonged inside.  I placed both hands on his
knees, leaning forward.  In this position I could rock back and forth on
his shaft.  Doing a slow steady ride.  Rob placed his hands on my hips, his
fingers tucked into my garter belt.  I rose up an inch or two then back
down.  I stopped moving, holding his cock prisoner.  His cock head twitched
inside, as I threw my head back, letting out a groan.

   I was content to sit like this all night, but Rob tried to buck up into
me.  Lifting his hips off the bed, along with me.  I got the message.  I
began to bounce on his pole.  My cheeks left his hips, as I raised up, then
dropped back down.  It felt lovely.  I rode him for a few minutes, keeping
up a steady motion.  Rob pulled down on my belt as if to impale me on him
deeper.

   My legs were cramping up from being tucked under my ass during all this.
I suddenly raised up off Rob's shaft.  He was pissed.

   He said "what the hell are you doing."

   I told him about my legs.  I said "I need to straighten my leg out.  I
thought, if I can extend them I would be fine."

   I told Rob to swing his legs around drape them over the side of the bed,
placing his feet on the floor.  I moved off to his side, he muttered and
moved as I suggested.  Once he was in place I stepped onto the floor,
spread my legs then backup past his knees, on over his thighs.  Lowering my
bum a bit, until I felt his twitching cock at my crack.  I slid up until
the head aligned with my pussy.  I sank down onto him with no effort.  I
was so loose I think I could take his fist now.

   I was sitting on Rob with my stocking covered legs rubbing against his
thighs.  I quickly started to ride his shaft up and down.  Rob was laying
flat and again reached for my belt.  He tucked his finger in so that his
hands could keep up with me.  Bouncing off his thighs, it felt like I had
springs in my ass.  A squeal slipped out of my throat, surprising me.  It
sounded like a girl.  That was the first time for that.

  As I pounded down on Rob's cock, I noticed his hips and ass were sliding
off the edge of the bed.  This wasn't working as well as I had hoped.  I
stopped fucking him.

   "What's wrong now?" he demanded.  By the tone in his voice, he was
getting frustrated.

  I said "your sliding off the bed.  We need something under your ass."

   I saw his weight bench.  Leaning over, I grabbed for the leg, wanting to
keep him inside if I could.  Stretching until he was about to pop out, I
got a finger around the leg and pulled.  It didn't move much, but enough to
get a couple more fingers on it.  The two twenty pound weights were still
on it, which made moving it harder.  Once my hand was on the leg, I tilted
the bench until the weights slid off.

   Rob raise his head up and asked "can you make anymore noise?"

   I said "just get ready to be fucked to death ."

   Still with Rob part-way in, I slid the bench over to us.  I told him to
spread his legs and lift his hips up.  With both hands, I worked it under
him until it was against the bed.  As much as I tried, Rob's cock popped
out.  We both let out a groan.  But we would be back to fucking in
seconds. The height of the bench to the bed was pretty close.  I asked him
how it felt.  He said "fine, lets go."

   Knowing this would be our last affair for a while, I wanted this one to
be special.  I again backup to his swollen cock, as it pointed straight up.
The head wedged between my bum cheeks, I raised up, sliding it along my
crack.  When the tip touched my pussy hole, I stopped and held still.  I
wanted to tease him.  Pay back for the times he teased me.  But Rob would
have none of it.  Sensing my wanting to draw the action out, he lifted his
hips, ramming his cock half way inside.  He held himself up until I drop my
pussy down, swallowing it completely.  When he laid back onto the bed, I
rode him down.  We both groaned our satisfaction.  I leaned forward, with
my hands on his knees again.  Rocking on his hips, this time I knew nothing
would stop us.  I rolled forward and back, my cheeks never leaving his
thighs.  Rob laid quietly except for a moan every so often as I rolled
back, driving his boy bone deep up inside.  At times, with him buried to
the root, I would stop and set motionless, my head back, eyes closed,
enjoying the sexy feel of his twitching shaft.  My pussy encircled it
lightly at the base like my lips did while milking his sack dry.

   Once I had my fill of silent, soft fucking, I was ready for the loud,
hard fucking.  Without warning, I rose up until his head was nearly out,
than dropped hard down.  If he didn't know then, Rob knew soon that I was
ready to finish him off.  I quickly rose up and down, repeating my motion
again and again.  I was letting gravity do some of the work, shoving his
head as far up as possible.  I got into a rhythm, raising up and dropping
down.  Rob didn't move a muscle, except his lovely cock.  I took my hands
off his knee and placed them to my thighs.  I caressed my stockings wrapped
legs Lost in my sissy lust.  The sex was great, but without the lingerie, I
probably would not have been as interested in sex.  The first time when Rob
stuffed his cock in my mouth, while I was asleep, was a complete surprise.
But when I got to dress in satin and lace, I would do just about anything.
I may have resisted Rob's second advance if he hadn't dressed me in mom's
panties and slip.  But as I fucked myself on Rob's six-inch college cock, I
was loving it all.

   I bounced on Rob for what seemed like an hour.  My cheeks making a
slapping sound, like my ass was being paddled.  I was ready to drain his
sack of every drop of his warm juice.  I could hear squishy sounds coming
from my bum.  My speed increased until the bed and bench were creaking
wildly.  I was afraid the bench might not hold up.  It twisted and racked
with each of my down motions.  Rob was grunting like an animal on the edge.
He was getting close to releasing into me, and that's just what I wanted.

   Rob grabbed my garter belt, pulling me down and held me there.  He
tensed up, lifted his hips and exploded into my pussy.  He cum geyser shot
a warm stream up inside.  He bucked up a couple times trying to force his
goo even deeper.  The feel was heavenly.  I did a slow rock back and forth,
milking Rob's pole with my pussy.  He kept pumping but his jets were
lessening and becoming weaker.  His second time of the night didn't have
the intensity as the first.  But I was completely satisfied now.  I let out
a soft low groan as I accepted his last pulses of cum pudding.  My skin was
damp, from the workout we had just gone through.  My cheeks were stuck to
Rob's tummy by the sweat and our juices.

    Rob released the waist of my garter belt, his arms dropping to his
sides.  His cock went semi-soft inside.  I leaned forward letting him slip
out from my well fucked pussy ass.  My stretched open pussy hole began to
leak thick ooze onto Rob's sack.  Lifting a leg up over Rob, I slowly stood
up.  My legs were weak, sore and shaky, but I was happy.  Cum ran in a slow
stream down the back of my thigh, into the top of my stocking.  As I
reached for a towel, I turned to face Rob for the first time.  His cock and
balls were a gooey mess.  He had a puddle of cum in his pubs.  As he
shrank, I lifted and wiped his parts, being sure to do a good job cleaning.
I also was hoping my attention of him would maybe get him hard again.  I
would have been willing to go at it again after a short rest.

   After he was cleaned, he said that he was wasted and ready for bed.  I
moved his legs so that I could slid the bench way.  Once it was moved, Rob
raised his legs and swung them on the bed.  He rolled onto his side, his
bum sticking out at me.  I stepped to the side of the bed, patted his bear
butt then pulled the covers up over him.

  He was asleep before I finished picking up.  I found my gooey taps,
stepped into them and pulled them on.  I felt like a well-fucked slut now.
I was tired but I needed to take a long, warm bath. I turned off Rob's
light and walked out.  Rob got his gift and so did I.

   When Rob came home during his first semester break, he told me, he had
decided that he wasn't going to chance getting caught screwing me.
Besides, his attention was completely on girls.

   Even my late night blow-jobs were over.  I use to sneak into his room
while he slept.  Wearing a pair of panties under my robe, as carefully as
possible, slide the covers until I could nuzzle my nose into his crotch or
bum crack, which ever was accessible to me.  He would just laid softly
moaning and raising his hip as I swallowed him until he fed me his milky
juice.

   He said what we did was experimenting.  He was now over that kind of sex
and we were not doing any of that again.  I was a little hurt and
disappointed but was ok with his decision.  Besides I was getting better at
fucking myself with things I found around the house.

  I did get fucked again, but by someone else.  I'll write about that soon.