Date: Sat, 26 Feb 2011 10:17:02 -0500
From: RG
Subject: Training of Bobbie

This is an adult story half truth and half fiction. If it is illegal to read
where you are then leave now.  If you are under 18 then leave now.

    This happened a long time ago in a small New England town.  The year
was 1959 and I was 15 and skinny and wore glasses.  My family genes give
every male and female a bubble butt.

 My name is Robert but everyone called me Bobby. I weighed about 85 pounds
and stood 5 foot 5 inches.  My parents owned a farm and just barely got by
with the bills.  We bought our feed and supplies from a general store in
town run by Richard and his wife Pam.

  Richard was in his mid fourties, a big man around 6 foot and well over
200 pounds.  He had a little bit of beer belly but for the most part was in
great physical shape. His hair was short and he was quick with a smile and
always would tussle my hair and call me sport.  I liked him a lot.

   Pam was in her mid thirties and besides working in the general store
also had a little dress shop connected to the general store where she sold
fabric and made custon order dresses.  She was about my height and was
shapely with big tits and always smiling.

    The first part of the summer my Uncle came to live with us. He just got
out of the army.  That took a lot of the work that I was doing away.
Richard had mentioned to my dad that he was going to hire a teen to work in
the store since his business was doing so well.  Richard stopped by the
farm to deliver some fertilizer and spoke with dad for quite a while and I
was called in to the room. Dad asked how I would feel about working in the
store to help with the bills.  Since dads brother was helping on the farm
it would really help out.  I already knew that I didn't want to be a farmer
when I got older and thought this would be a great chance to learn
something new.  It was agreed upon, mom would drive me in to town each
morning and Richard would drive me home, The trip was about 12 miles.

  Monday came and I went to work and learned how to stock shelves.  I would
help Richard load the truck for deliveries and work the store with Pam
while he was gone.

   School was in town and the summer flew by I learned how to inventory and
stock shelves, run the register, and add supplies to peoples accounts. The
job was fun and I was going to hate leaving it after school started. My
wages were working of the debt that we owed to the store.  The week before
school started Richard and my dad were talking one day and a proposal was
made. I was to take a room over the store where Richard and Pam lived for
the school year and work the store after school.

  I moved in the first week of school and everything was fine. After we
closed the store we would sit and chat or watch a little tv, that is after
my homework was done and checked by Pam.  She would lean over my shoulder
and point to where I was wrong.

 After about a month Pam got a big order for several dresses for a formal
that was to be held in a country club.  She would work on them after work
and I would chat and watch.  The third dress was where it all started.  She
only had two forms to work dresses off of.  Well she told me I was going to
have to be her fitter for some of the work.  She helped me slip the dress
on over my shorts and tee shirt..

  This won't do at all said Pam You will have to take the shirt and shorts
off. I slipped in to a slip she handed me and she slid the dress over my
head.  As she was smoothing the dress out she ran her hand across my cock
and it started to come to life.  I was horroified.  Pam worked moving some
material here Pinning some material there.  What seemed like hours she said
we were finished for the night and helped me take the derss off.

   That night in my room I masterbated thinking about each time Pam had
brushed across my cock while working on the dress.  When I orgasmed it was
one of the most intense of my young life.

   As soon as the store was closed the next night Pam informed me I was
going to have to help again tonight.  She also told me she needed me to
wear panties because my briefs distracted her because of the lines thy made
in the dress. She handed me a pair of pink panties and insisted that I wear
only them under the dress.  I started to protest but she would have none of
it and insisted, now go change she said and meet me in the sewing room.

   After changing and putting on the panties I sheepishly entered the
fitting room where Pam was waiting. She slid the dress on and pinned up the
back.  Today we are going to work on adding th shiffon pleats to give the
dress fullness.  As Pam worked she would brush my cock with her hand or arm
and I would squirm and my teenage cock was growing.

   Pam soon noticed my problem and started teasing me about not being able
to control my body. A proper young lady has to be able to control her body
at all times she said.  Pam reached for the hem of the dress and removed it
and laid it back on her cutting table.

  Now there I am standing in a pink pair of panties and nothing else except
a 5 inch hard on.  Pam walked up in front of me and looking me straight in
the eye said and exactly how do you expect me to get a proper fit to that
dress with this in the way.  Still looking me in the eye she had reached
down and was squeezing my hard on thru the panties.  I about came on the
spot.  She released my cock and brought her hand up to the waisteband and
slid her hand inside.

  Is this the first time anyone else has ever touched your cock she asked.
With a voice that was about to crack I squeeked an answer... Yes I said and
please if you don't let go I'm afraid that I am going to make a mess.  Pam
just laughed and said that she had to have me available to fit the dress as
she had a deadline.  Reaching over to the cutting table she grabbed a few
tissues and with her other hand proceeded to continue to stroke my cock.  I
was quickly approaching orgasm and told her so.  She pulled the panties
down and tucked the waistband behind my ballsack and started to stroke me
in long meaningfull strokes. Her eyes never left my face watching every
contortion and twitch I made.  I could feel the orgasm approaching and had
to put my hands on her shoulders for support or I was going to fall over.
The eruption was the best that I had ever had and was sure that nothing in
the world could beat it.  As I was cummiing she had placed the tissues over
the end of my cock and caught all of the semen.  She continued to milk my
cock till nothing else came out.

   Pam threw the tissues in the trash and grabbed another handfull and put
them in the front of the panties and tucked my cock down and back between
my legs, now back to work she said ,matter of factly. Up went my hands and
she lowered the dress back down and went to work pinning and folding,
folding and pinning .  this went on for the next 2 hours.

  That night as I lay in bed thinking about the events of the day I could
hear a lot of noise coming from Richards and Pams bedroom.  They were
making wild passionate love and were none to quiet about it.  I masterbated
to the sounds coming from their room and imagined it was me making love to
Pam.

  The next couple of days were very buisy in the store.  I would load the
truck with whatever the next days first load was supposed to be.  Some of
the bags were very heavy and Richard would come out and help me load them
on the truck.  A few times I felt like Richard was watching me in a
different kinda weird way, I don't know.  I really couldn't put a finger on
it.

   Richard, My dad and uncle were going away for the weekend so I would
have to be the man in the store.  When I got to the store from school on
Friday they had already left and I got straight to work.  At closing Pam
came in to help me lock up and said we needed an hour to finish the dress.
Go put the panties on and come to the fitting room.

   As the girl the dress was for was close to my size, as far as waist and
butt were concerned the dress would fit perfectly.  Pam came over with a
bra and said I would have to wear it so she could finish up the top of the
dress.  After she had put the bra on she stuffed the front with a couple of
pairs of pantihose and some batting .. Stepping back a few feet Pam
surveyed her handi work and said I would make a nice young lady, what with
my fair complexion slim waist and bubble butt. Pam worked for the next hour
pinning and cutting till she had everything just right.  Done she exclaimed
about ten thirty.  Pam pulled the dress over my head and I reached behind
my back to undo the bra.  Wait she said I want t try something.

   Pam came over to me with a thing with a lot of string on it .Whats that
I said, a corsett was her response.  She helped me slip it over my head and
she got behind me and started to pull and tug and laced it up.  I could
barely breathe.  I was instructed to sit on a stool and not move.  Pam
started to apply makeup to my face, she did my lashes, lipstick for the
lips, eye liner.  She went over and got a wig out of a box and put it on me
then went and got a white short gown and pulled it over my head.

   Amazing she said as she led me over to the double mirrors..  What I saw
in the mirror was a beautiful young lady with a very slim waist.  Wow was
all I could say.  Pam and I looked in the mirrors for a few minutes.  We
laughed and giggled like two school girls. Pam led me from the room and we
made our way up to the living section of the store.

   I have a confession to make Pam said.  When I was in high school I used
to fool aroud with a couple of my girlfriends.  I wasn't quite sure what
she ment and told her so.  Pam turned to me and took me in her arms and
gave me a very passionate kiss. As we kisssed she forsed her tongue in to
my mouth and I accepted it willingly, my young horemones were on overload.

   When we got to the master bedroom Pam led me in and gently push me back
till I was sitting on the bed. She backed up a few feet and started to
disrobe.  I was in a trance, granted this was no young slender girl, but
this was the first woman I was going to see naked.  She slowly removed her
blouse and bra and came over to me sitting on the bed and fed me her left
tit.  Suck on it babygirl she said.  I went at it with earnest.. Easy, use
you lips and just a little teeth she said.

   I reached up with my hands and hefted her breast and was neading it and
just feeling around.  Pam took my left hand and placed it on the right
breast and told me how to play with the nipple.  I was feeding like a
newborn getting his first feeding.  I continued to suckle her left tit till
it was pulled from my lips and replaced with the right one.  Pam then took
my hand and guided it up under her skirt to her sopping crotch area, man
was she ever wet.  I worked my fingers around the legband of her panties
and inserted a finger in her pussy. This was a funny feeling.

   Pam reached down and pulled my hand from under her skirt and guided it
up to my face and told me to lick my fingers.  I placed my fingers under my
nose and smelled a pundgent odor and sucked her juices from my fingers.

   Again She backed away and removed her skirt and panties.  For a fifteen
year old this was the most beautiful woman in the world. I reached out and
started to play with her pussy, first with one finger then with 2.  She
reached down and guided my fingers to her swollen clit and told me about
this being the love button to a womans satisfaction.  I started rubbing it
in ernest.  Pams breathing was becomming ragged and she was telling me that
right oh yes finger my pussy.

   Pam laid on the bed and said I want you inside of me.  I got up to
disrobe and she said, no now, just take the panties off.  They were off in
a split second and I was back on the bed with the gown around my waist.
She guided my cock too her waiting pussy and In one push I was in to the
hilt.  I wish I could say we made love for an hour but it was more like 6
or 7 strokes and I was shooting my boy juice in to the first pussy I had
ever seen., It was great.

  We lay back on the bed for a few minutes and caught our breath, all the
time she was telling me how exciting it was for her and the things she was
going to teach me.  Pam reached up under the gown and started to masterbate
me and telling me it was time for a new lesson as she moved down on my body
and had me lay on my back.  Lower she went till my cock was at face level.
looking up at me she lowered her mouth and engulfed my cock to the hilt.

   Oh what was this all about. I thought being in a pussy was great.  This
was fantastic.  As she was giving me the blowjob she came up off my cock
and told me she was going to make it even more exciting I just had to trust
her.  I nodded yes and she went back down on my cock and started to let
spit run down the crack of my ass.
  The next thing I felt was a slight pressure on my asshole as she slowly
worked a finger in to that virgin hole.  It was uncomfortable and I had no
idea how this could give me pleasure. Slowly she was sawing her finger in
and out of my ass as she continued the blowjob at the same pace.  I was
getting use to the finger in my ass and Pam said that in order to reach the
place she was after she would have to put in a second finger.

    Ever so slowly she worked a second finger in my tight rear enterance.
As she had most of the fingers in I felt like an electric shock and my cock
got even harder than it had ever been.  Pam was no longer sucking my cock
but was instead milking my prostrate.  As she was working two fingers in
and out of my ass she started to masterbate me again with her free hand.
let me know when you are close she said.  Unable to speak I just nodded my
head.  I could feel the orgasm building and told her so and she again went
down on my cock with that incredable mouth of hers.  As soon as my cock was
in her mouth I exploded.  She pulled her fingers from my ass and wiped them
on a towel I hadn't noticed before that was on the edge of the bed.  Pam
slid up my body and gave me a kiss forcing my mouth open with her tongue.
I didn't realize that she hadn't swallowed my cum and shared it with me.  I
tried pulling away but she grabbed the back of my head and held tight as
she fed me my first taste of warm man milk she called it.  Man what a night
this had been.

   After about 5 minutes of rest Pam asked if I was ready to learn more.
What else is a teen boy going to say.  First since you are dressed as a
girl we are going to pretend you are a girl ok.  I said yes and since my
name was Bobbie that would work as a girls name she said.  Now I am going
to have you make love to me as I you were a girl and am going to teach you
what my girlfriends and I used to do together.  First come up here and give
me a kiss.  While we were kissing I was instructed to finger her pussy and
apply a little pressure on her clit while I did.

   Ok sweetie move dowm my body kissing as you go.  My thats nice oh yes
suck on mamas nipples as i engulfed the peanuts sized bud in my mouth.
After spending a few minutes working between the left and the right nipple
a few times Pam put her hands on my shoulders and started pushing me lower.
Remove your fingers and use your tongue she instructed.

    Pams breathing was becoming ragged and she inhaled a large breath when
I hit her clit with my tongue. The taste and odor was a little pundgent and
took a little getting use to, but since she had given me a blowjob and was
teaching I was willing to do anything for this woman who was old enough to
be my mother. I was going t town on her clit and reinserted first one then
two finges in her pussy which easilly accomidated them.  Pams breathing was
now coming in short gulps as she approached her orgasm and I was sucking up
her juices as fast as I could.  The juice was flowing down the crack of her
ass so I maturally slid a finger in to her asshole and she exploded holding
my head in place.  I thought I was going to suffocate she was holding me
down so tight.

    Mmmm that was what my girlfriends and I used to do to each other she
said and you were evry bit as good as one of them.  I was beaming with
pride.  Now cuddle up with me we need to get some sleep Pam said.


End of chapter 1