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Educating Heather

1/30/2009

I sat alone one evening with a glass of wine and my favorite
CDs playing , glad that the hectic week I had just put in was
over ! Having a job with a lot of responsibility can be exhausting
! Alone with my thoughts and feeling a little horny , my mind
drifted to where it all began. I am Heather , 28YO. , 5’3”
, 105 lbs , slim and a real blonde although I do lighten it
at times. I have my own office and that to is a source of some
great stories but for now I will relate my opener i.e. where
it all began.


I was 13 when I had my first boy and what a mess. My girlfriends
had all tried it and were pressuring me to give it a try. I
had been masturbating for over a year and certainly enjoyed
that so I figured it can only get better. I guess my mistake
was in not picking a boy with a little experience but my neighbor
Sean , a good friend and a cutie was all ready spending lots
of time (innocently) with me either in my room or his at his
house. His mother was always around and my sis was suppose
to be keeping an eye on me at our house although she never
once intruded on Sean and I and little brother Billy was
never around. I guess she just didn’t care or maybe hoped
something would happen as I considered later.


Anyway , one afternoon in my room with Sean I innocently
asked him if he ever thought about sex. ”All the time “ he replied ”Do you ever think about sex with me “ I asked. ”All the time “ he again replied although a little sheepishly.
”Do you find me pretty” ? ”Heather , I think you are the prettiest girl in our class”
he answered. ”Do you ever picture me with no clothes on “ ? I asked. He turned red , lowered his head and answered “yes”. I was getting pretty brazen now as I felt in control of the
situation. ”Would you like to see more of me “ ? ”Like what ?” he asked. ”How about my breasts “ ? ”Oh golly yes Heather , I sure would”. ”OK , but just look , no touching” I demanded.


I turned my back and removed both my sweater and my bra (which
I barely needed) and when I turned around and saw the look
in his eyes and him trembling it eased some of my embarrassment.
I could also see the bulge in his gym shorts which made me
a little proud !


He just stared and stared so to get the ball rolling again
I suggested he touch them. I was getting pretty bold! He
put one hand on each of my breasts very tentatively and I
told him to rub my nipples with his thumbs. Up until this
point I felt totally in control but I now felt a little slippage
as his rubbing sent tremors all the way to my pussy. I knew
what was happening for as I said I had been masturbating
for over a year but this was so deliciously different. I
sometimes wonder if I could have orgasmed just from his
touch but I was too impatient for that. I did have to tell
him to ease off when he started squeezing them too hard.
Getting even bolder I reached into his gym shorts and grasped
his cock which made him jump back but keeping his hold on
my breasts. He was small but hard as a rock.


”Please don’t stop” I hissed as I slowly began to stroke
him. I removed my hand and with both hands slid his shorts down
exposing his cock. It’s beautiful I thought and knew right
then that I wanted it in me. ”Sean , pull my skirt and panties down” I insisted. He was
so excited I had to remove his shirt and pull his shorts all
the way off but he finally did as I asked and slid both my skirt
and panties down and off. I led him to the bed , laid down with
him and suggested he should kiss me. He did so and returned
his hands to my breasts. It felt so wonderful to feel my nipples
get hard in his hands. I placed my hand on his cock again and
stroked it a little while we kissed. He was shaking all over
due to his nervousness making me feel like the one calling
the shots as I was. I was hot now so I took one of his hands and
placed it on my pussy and told him to rub lightly which he
was more than happy to do. His finger penetrated my labia
and unbeknownst to him stroked my clit. This really got
me going but he warned me to stop playing with his cock or
he was going to lose it.


”Don’t you dare Sean” I cried. “ I want you in me first” ! He replied , ”well we better hurry then”. I rolled over to my back and pulled him on top of me grasping
his cock with my fingers for the proper alignment. I rubbed
the head up and down my slit until I felt the tip at my opening
and told him to slip it in and push but slowly and gently.
This is where the trouble started. He went berserk trying
to ram his cock into me hurting me as I attempted to slow him
down. When my hymen broke the pain was excruciating ! He
lasted about 3 strokes then he cum all in me before my pain
had subsided at all. Attempting to ease my pain I pushed
him off me and could feel his cum and my blood running out
of my pussy.


”You hurt me Sean , You hurt me a lot” ! I cried. ”I’m so sorry Heather but I couldn’t stop myself “. I now chuckled to myself thinking how many more times I was
to hear that in my future ! ”I think you better go now Sean “ I said to him ”It will be better next time Heather I promise “ he tried
to convince me. ” There will not be another time Sean and I mean it “ ! And there
wouldn’t be at least not with him.


So for about a month I lost interest in sex , even the masturbation
had stopped. I did finally start again but it was not the
same anymore as I was left with this feeling of loss and a
great sadness and I had lost a good friend due to my own selfishness.
End of story ? No way! It was actually the beginning of a better and happier one.
One night some time after these events occurred I was laying
in bed watching TV when my sis , Carrie came into my room (we
had a door that connects our rooms without going into the
hall) wearing just panties as usual. Carrie was a senior
in high school and gorgeous. She has my dads height and my
moms terrific shape and blonde like me. We are pretty close.



”Heather , have you seen my blue satin panties that go with
my cheer leading outfit” ? ”No” I replied. She rolled her eyes and said , “Billy probably has them “.
I thought that was an odd thing to say as what would my 11yo
brother want with her panties. I was to find out a couple
of years later , but again that’s another story. She gave me a real serious look and asked , “Heather , are
you OK ?. You’ve been really down for a while. ”No , I’m OK” I lied. ”You can tell me you know as we have never had any secrets
“. ”Not this time , OK”? I said. ”How about if I guess what’s wrong. Will you tell me then
? she asked. ”I guess so uh , maybe “ ”Have you tried sex ? And there it was , the big secret out for her to know about
! I teared up and told her yes and it was awful. She sensed my pain and lifted the covers and slid into bed
with me , taking me into her arms. I started to cry lightly and related the whole story to her
and while I was doing this she caressed my hair and felt my
face even kissed me gently between sobs. ”It’s never as good as it should be the first time” she stated. “Especially with boys as they play too rough
not realizing what we need is tenderness. Only other girls know how to treat their partners with the
gentleness we need”. I wasn’t sure what she was getting at but it was then I realized
she had slid her hand up under my PJ top and had rested it on
my right breast ! She was running her fingertips across
my nipple and it felt so wonderful that I blocked out the
fact that not only was she a girl , but my sister ! I lay there
for a while enjoying this new found thrill but finally asked
, “Carrie , should you be doing this “? She replied , “I just want you to see that you don’t need a
rough groping boy to feel sexual pleasure and I won’t do
anything you don’t want me to do , OK” ? ”OK” , I reluctantly agreed.


She moved her hand to my other breast and strummed the nipple
as she had done to the right one. This went on for a long time
and it felt so good not to have to hurry and worry so I just
let her lead the way and I certainly did not want it to stop
! I could see her much larger breasts as well but didn’t even
think about touching them. ”This one is just for you Heather” she whispered. She lifted my PJ top up and off me and stared at my breasts
longingly and then caressed each with her left hand keeping
the back of her right hand on my cheek. For the first time
in my life I could feel the wetness forming between my legs
as the sensations continued to grow. ”Do you want me to stop Heather” she asked. ”Goodness no “ I replied. She then took my entire left breast in her hand gently squeezed
it causing my nipple to protrude , then kissed it. Then licked
it. Then sucked it into her mouth ! I was really liking it
by this time and both my nipples were rock hard. She did the
same to my other breast and with my nipple still in her mouth
slid her fingers down over my belly rubbing it. I knew where
she was headed but didn’t say a word because I was afraid
she would stop. Her fingers slid under my PJ bottoms into
my cotton panties , over my pubic bone onto my pussy. Oh
my god I thought. She’s going to touch me there ! Her fingers
separated my labia and one pressed on my clit rubbing up
and down a couple of times before placing her finger at my
opening. I started to shake knowing what was coming while
she continued to suck on each breast in turn.


It was all I could do , just lay there and feel. I was getting
so hot knowing where all this was headed. It was like foreplay
x10 ! Sis was being so gentle whispering soft words like
how beautiful I was and how excited I was making her. I was
moaning softly to her caresses but when her finger started
to enter me I froze but just momentarily as I pictured Sean
forcing himself into me. She hesitated and asked me if I
was all right and I replied “yes , now I am but please go slowly
and don’t stop. Please Carrie , you can your finger in me
“. She very slowly and gently slid her finger all the way
into me and it was so super , different than anything I had
ever experienced. I felt my vaginal walls squeeze her finger
and when she started to slide it back out , my suction attempted
to hold her in. She very slowly finger fucked me for a while
then pressed her thumb against my little bean and rubbed
it as I lay there moaning. It was all ready starting deep
within me and I was shaking all over. She kissed me deeply and inserted her tongue into my mouth
to stifle my moans just at the right time or I think our folks
would have heard my screams ! Oh my god , my sis is making me
cum , my sis is making me cum was the only thought in my mind
! I don’t think I have ever loved anyone more than her at that
moment. She was giving me what I needed so badly. I wet her
hand with my juices as she hugged me really hard with her
other arm and her tongue still in my mouth until my spasms
ended. I lay there crying softly but with joy this time.



”Thank you so much Carrie , I really needed that” ! ”I know” she replied. “You will sleep so much better now.
You have found peace”. She was so right. My whole attitude took a turn for the better.
It was like I had my life back. And it didn’t end there ! A few
nights later sis entered my room again and slid right into
bed with me once more. Only wearing panties again she looked
not just beautiful but sexy now. This time I helped out by
getting out of my PJ s and panties completely and waited
for her hands and lips to make contact. We kissed for a while
this time with out tongues taking turns invading each others
mouths. The familiar hands started their roaming again
over my breasts and tummy while she formed an O with her lips
and sucked one of my nipples right into her mouth flicking
her tongue on the tip. Oh my I thought. It sure comes easy now. I lay there and experienced
her experience and found that when she worked both of my
nipples together I could feel the tingling in my pussy so
I asked her not to stop , please ! After a while of doing this
I was feeling brave and placed one of her hands on my mound
(as if she needed guidance). I was getting really wet now
and without hesitation she slid not one but two fingers
into my snug passage and as before her thumb rubbed my nub.
I could feel my pussy stretching to accommodate her two
fingers but being excited and wet they pretty much slid
right in. I could feel it start. Oh my , here we go again I thought
! Gently in and out in and out with the thumb on my clit driving
me insane.


” Oh my god Carrie , I am going to cum again” I cried. ”SSHHH , mom and dad will hear you”. She once again muffled
my cries with her mouth on mine while I dropped over the edge.
Spasm after spasm wracked my body until I was spent. Looking up at her after my heart slowed down she asked “Have
you ever smelled yourself “. I said no so she held her hand
under my nose. I must say it did smell strangely exciting
but when she then placed her fingers in her mouth I was shocked.



I then had to ask. “Carrie , do you get anything out of all
this “? She replied that it gives her great pleasure to give
me pleasure but it does leave her a little frustrated. So
gathering up my courage I asked her if she wanted me to do
something for her. ”I sure would but only if you want to” she answered. ”I don’t know how though”. I said. ” Heather , just do to me what I do to you , at least for now”
and smiled. Not knowing what she meant by “for now” I figured
the least I could do would be to masturbate her as she had
done for me. Here goes I thought.


”You’ll have to help me Carrie , I’ve never done this “. ”My pleasure I assure you and just do what feels good to you
also. It will come naturally “ she replied. It was kind of awkward for me at first when our lips met but
when she traced my lips with her tongue I started getting
into it. I slid my tongue into her mouth and heard her moan.
That got me going more as it felt so grown up to get her excited.
Instead of palming her breasts my mouth went right for her
nipples. I guess she loved this as she placed her hand on
the back of my head and pulled my mouth onto her flesh. I pulled
my head back and began licking her all over her neck , breasts
and nipples. She was delicious ! What was most amazing to
me was that I to was getting excited ! This was so great. I licked and lapped and sucked everywhere
my mouth would reach and was absolutely loving it. ”Heather , my pussy , now “ she cried. I first rubbed her through her panties and them slid my hand
under them and placed my hand on her cunt (at times like this
I just love that word). I loved the feel of her soft silken
blonde hair I found there and the wetness , oh my she was soaked
! ”Take my panties off Heather, I want to feel all of this “.
So removing my hand I then placed them on her hips and slid
her panties down and off (hers were silky nylon) and threw
them across the room , both of us laughing. It was so good
then ! Back to her breasts I went with my mouth and back to
her pussy I went with my hand. She was right , it did come naturally.
I rubbed her slit marveling at the wetness I found there.
I easily slid a finger then two and even three into her passage.



”Finger me , finger me Heather and you can go a little faster
with me” she suggested. Unsure of this I started to more
rapidly pushing my fingers in and pulling them out then
onto her clit causing her to moan louder than I ever did.
This continued for almost ten minutes. ”Faster , faster “ she pleaded. I felt her start to shake
all over as I went faster but gently nor wanting to hurt her.
With one hand she pulled my face into her breast and with
the other was pushing my fingers harder into her pussy.
When she orgasmed she soaked my hand with her juices which
got my motor running big time. When her spasms ended , knowing
I was again hot she once again slid two fingers into me and
got me off in record time ! Afterward I lay there marveling
at the wonderful experience Carrie had introduced me to.
This went on two or three nights a week for about six weeks
when she decided I was to take the next step as she put it.
I was unsure what she meant but anxious to find out.


”It will have to be after school to be sure mom’s not going
to be home” she stated. “Getting caught in bed together
is one thing as mom knows we are close but what’s going to
happen next would be bad news if we get caught” she exclaimed.
Now my anticipation was peaked ! I tried to imagine what
she had in store for me. Well, the day finally arrived. It was a Wednesday , when
mom worked a couple hours extra and dad never got home before
6:00 or so. I remember it well ! Carrie came into my room and asked if I was ready for lesson
2. I replied “Yes” as I to had been waiting for lesson 2 whatever
it was. She stripped down to her panties and then undressed
me to my panties like her. We got on top of the bed and began
kissing and as usual caressing each others breast which
lead to licking and sucking them. I felt the familiar hand
wander to my panties sliding into them and rubbing my pussy.
This would be all I really needed but she wanted to show me
more.


She rose up over me and with both hands slid my panties down
and off as I lifted my buns to assist her. With each of my breasts
in her hands she placed her face on my tummy licking my navel
causing me to giggle but then she started moving her face
lower toward my pussy. Oh no , oh no I thought ! Not there !
When her mouth met my pubic hair I screamed , “Carrie not
there , not there , that’s where I pee” ! Her reply , “trust
me on this “. With the fingers of each hand she spread my pussy
open and placed the flat of her tongue right on my openness
! “Oh my god , Carrie , oh my god Carrie”. I cried , “no don’t
, no don’t”. But there was no stopping her. She slid her tongue
right into my tunnel then with a slight pressure slid it
up to my clit. I think I became a bi at that very moment ! It
was like striking a tuning fork as waves of the ultimate
joy passed through me. She moved her tongue back to my tunnel
and slid it in and out for a while. All I could do was lay there the pleasure was so great ! Back
to my clit went her tongue for a few swirls then sucking my
inner lips into her mouth then back to my hole. I felt it start
deep within me like never before and when she once again
sucked my clit into her mouth and started to run her tongue
back and forth over it my orgasm began. I placed my hands
on the back of her head and pulled her face into me and cum
all over her. She began lapping like crazy to catch all my
juices as spasm after spasm ran through me. She had placed
her hands under my buns holding her face into me so when I
tried to push her away because I was going crazy , the sensation
being so great but she held on. I have never experienced
anything so powerful before or even since!


Since that first time we would get together every Wednesday
afternoon for more of the same and of course our nightly
trysts with us masturbating each other. We always agreed
that this would hold us over until the next Wednesday with
a chuckle. And of course it was not long before she had me
licking her pussy to orgasm also. She taught me to 69 and
we were soon able to time our orgasms to happen together.
We formed such a bond that even my parents noticed it but
their only comment was , “that is so nice”. Lesson 3 probably saved me from becoming pure lesbian.
On one of our Wednesday afternoons she introduced me the
dildo. She showed it to me telling me it was hers.


”How do you hide it from mom” I asked. She replied “Mom knows I have it in fact she has one also “.
”Oh , wow - Mom ?” ! I exclaimed. ”Yup , remember , dad travels a lot” she said smiling. She set it aside while we began our love making and when she
had my pussy soaked with her oral play she sat up spread my
pussy open and put it at my opening. ”You know you can trust me not to hurt you right ?” she asked.
”OK but please go slow and be gentle”. ”Of course , haven’t I always been ?” she replied.


She applied a little pressure and it began to enter my almost
virgin pussy. I felt my cunt opening to accept it and being
so wet there was no friction and very little pain , more of
a discomfort. She twisted it and continued to push it in
until it hit the end of my tunnel and stopped. I lay there
feeling the fullness thinking this is not so bad. Allowing
time for me to adjust to the fullness she went back to my breasts
and my mouth kissing both.


”When you are ready to get fucked , tell me “ she laughed.
”I’m waiting” I joked in return. She went back down and licked my clit with her tongue tip
as she slowly slid the toy back out of me. I think the clit
action was in case I wasn’t really ready but I was indeed
ready! When she first began pulling it out once again the
suction of my pussy tried to hold it in but she persisted.
She slid it out of me slowly all the way then gently back in.
This went on for a while until she suggested that I try it.
Being in charge now I was able to adjust the speed of the in
and out action doing whatever brought the greatest sensations.
“Place it against your clit” she insisted , and when I did
she reached over and turned the vibes on ! Oh my goodness”
I cried being unaware of this ! I began to really get into
it and started twisting my hips and rotating my butt on the
bed as my orgasm started building. I placed two fingers
of my other hand on my clit as I slid the toy in and out of me.
Fast learner I thought to myself. It wasn’t long before
I cried “Oh my god Carrie , I am going to cum”!


”That’s the idea Heather “ she said with a chuckle. And cum I did ! It was sooo wonderful I even began to think
about sex with a real cock again. After a brief rest Carrie
informed me it was her turn for some action. I slipped off
her panties and went right for her bush which was all ready
wet. I now enjoyed the scent and taste of her pussy and I was
getting real good at this as she had informed me ! After she
climaxed we lay still for a while then asked me to do her with
the dildo which I did and then we 69ed for a finale. Quite
an afternoon I thought to myself with a satisfied smile.
She allowed me to borrow her dildo whenever I wanted which
turned out to be quite often as she wasn’t always home being
into cheer leading and a host of other interests. I got to
become quite a horny little girl thanks to sis.


Carrie said she had one more thing to show me and thinking
I now knew it all by now I could not imagine what it could be.
She said she had to borrow “something” from a friend and
would do so the next Wednesday. I couldn’t begin to imagine
what that “something” could be and she would not give me
any hints during our nightly masturbation sessions. Finally , Wednesday afternoon arrived and she had me get
naked and into my bed while she went back to her room. ”No peeking Heather” she said as she reentered my room ,
so I shut my eyes. ”OK , open them babe” she requested. When I did , she was standing there as naked as I was with a
dildo attached to some kind of belt around her waist. ”It’s called a strap on Heather” she told me. Well , there was no question what it was intended for even
to naive little me ! My eyes must have been popping out of
my head. ”Oh my god Carrie , you’re going to do me with that thing aren’t
you ?” I stated. ”Yes indeed!” she exclaimed. In my innocence I asked “where did you get that?” ”It belongs to Mrs. Jackson , the woman I babysit for” she
answered. Mrs. Jackson is our neighbor , a single mom , very beautiful
, shapely and black. ”You mean she let you borrow that ?” I exclaimed. ”Yes of course , god knows she’s used it enough times on me
!” What an education I was receiving ! Carrie and Mrs Jackson
going at it after the baby sitting sessions ! Oh my , oh my.
”It has different size dildos you can place in the harness.
This is the smallest one as you are still quite snug although
it’s still bigger than my two fingers” she told me. ”Does she know you are using it with me ?” I asked. ”Yes” she said with a smile “and she is quite jealous. Who
knows , maybe after I leave for college next fall you can
take over my “babysitting” duties” she joked.


She slipped into bed with me and we commenced our caresses.
I could feel the thing bumping me in my thigh area as we kissed
and fondled each others breasts. Our kisses became pretty
hot taking turns sucking on each others tongues. Then we
took turns getting each others nipples hard. Carrie remarked , “you sure are getting good at this little
sister !”. I answered , “you make me pretty hot big sister “. I could now feel my dampness so figured it was time to get
this thing in me. She had me roll on top of her and I began to
raise my butt to to get the dildo to enter my pussy but wasn’t
having much luck. I couldn’t seem to get the tip lined up
with my opening even with Carrie holding it and was getting
a little frustrated. After a few minutes of this I said ”Sis , I’m not doing well here “ ”Okay” she says , “bring your knees up along my sides” which
, after I did , “yes like that , now I will hold it in place while
you rock back , easy now. And I put plenty of lubricant on
it so it should enter smoothly “. ”Much better Carrie , I can feel the end now “. And then I moved
around just enough to place the tip at my opening. I slid
down and back and into my pussy it went ! I felt it slip into
my cunt covering it with my juices but there was a little
friction so I lifted my ass and again descended a little
further this time. It took three attempts until it was buried
all the way in me and just layed there enjoying the fullness
once again. Meanwhile , Carrie was stroking both my nipples
and my breasts which was getting to me. I couldn’t lay there
long as I was really hot by now so I began a very slow rocking
motion. My flow increased allowing me to speed up to where
I was fucking this thing in earnest slamming my ass up and
down on Carrie who was beginning to squirm beneath me. As
I was about to cum I grasped each of her breasts and squeezed.
This time a scream escaped my lips as I cum and cum all over
the dildo and my sisters thighs. It seemed that the more
I experienced sex and fucking the more flow I emitted from
my cunt. I shuddered to a halt and collapsed on her. As we
lay there she caressed my hair and kissed me gently telling
me how much she loved me. I looked into her eyes and knew from
her look it was her turn.


”Can I fuck you with it now Carrie?” I asked. ”Yes , I would love that but I will need a larger cock , wait
right here “ she said with a smile. She returned with a bigger
dildo put it in place , lubed it and wrapped the strap around
my waist. ”That’s pretty big sis , are you sure” I asked. ”Oh yes , it fit just fine last night when Mrs. Jackson was
plugging my hole “ she laughed. I suspected that as she got
home late from babysitting the previous night. I actually
felt a little jealous. I laid down and without any foreplay
she swung her leg over my waist and lowered her pussy right
onto the toy. She had been so wet she impaled herself in one
motion with a loud groan. I reached up and grasped her breasts
and tweaked her nipples which she loved. She rocked back
and forth for a while then said “now it’s time for you to fuck
me” ! She extended her legs , grasped my butt and rolled us
both over never losing the dildos placement.


”Okay , pump me now sis”. It didn’t take a genius to figure
that out so I lifted my ass which caused the dildo to slide
out of her almost all the way. She grabbed my butt and pulled
me back into her just before it did. So I fucked her letting
her set the pace by the pressure of her hands on my ass. I thought
, so this is how guys feel. I could sense her orgasm approaching
but first she rolled us back over , slid her knees back up
to my sides and took over the pumping. When she came she screamed
“I cum so much harder this way !”. All this of course left me hot again so after a break she again
put the toy around her waist , changed the dildo and fucked
me as a guy would , that is with her on top. And of course I once
again orgasmed. So on and on this went all through the rest of the school year.
That summer was the best in my life with sis taking me everywhere
with her especially the beach. My breasts and butt filled
out that summer giving me a pretty nice shape which Carrie
enjoyed immensely !


Sadly , she left for college in the fall and although we had
our “get togethers” whenever she came home it was never
quite the same , I guess nothing ever is. She did leave me
with a healthy appetite for bi sex which I now thoroughly
enjoy. Perhaps that is enough , perhaps not and I still miss
her so much as she moved to California after college.



Mr. Savannah

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Members can vote on this response!

Very well done and very hot. Looking forward to moreal experiences.
education

1/30/2009

Members can vote on this response!

that was a very nice and well wrote story of an earlier experience.

1/31/2009