


Hershey Highway, Her Way

by walterio



Category: Anal
Published: 2016-12-11
Updated: 2016-12-11
Packaged: 2017-05-02 05:41:06
Chapters: 1
Publisher: literotica.com
Story URL: https://www.literotica.com/s/hershey-highway-her-way
Author URL:
https://www.literotica.com/stories/memberpage.php?uid=429765&page=submissions
Summary: She loved anal and had her favorite position.
Erotica Tags: Anal Foreplay, Anal Sex, Car Sex, Her Way, Hershey Highway,
Insatiable, Large Cock, Massive Orgasms, Natural Lubrication, Spooning,
Vaginal Sex, Voluminous Ejaculations
Average Rating: 4.2






        Hershey Highway, Her Way


PRELUDE  
  
It was a Monday evening following one of my league softball games. We had
stopped at the bar that sponsored us for a few beers before I headed to
Carrie's apartment. Then it was right to bed in her favorite position for anal
sex. She loved having my cock in her ass and savored the moment when I would
cum in her rectum. We were always on our left side with my left arm under her.
I would fondle her breasts with my left hand while my right was rubbing her
clit and finger fucking her pussy.  
  
My 7" cock would be balls deep in her ass as I fucked her slowly with three
fingers buried in her sopping wet pussy. She would be muttering unintelligible
sounds of ecstasy as I worked my cock in and out of her warm chamber. Carrie
would orgasm several times before I ejaculated into her bottom. My first cum
of the evening was always voluminous and I would flood her rectum. That would
usually trigger an intense climax that rocked her body.  
  
"Oh yes, I can feel it. Cum in me, shoot it deep," she would call out.  
  
I would feel her sphincter clench and release my shaft several times as her
love juices drenched my fingers. The feeling of her gripping and tightening
around my cock kept me hard and I was always able to cum a second time. We
would stay coupled together in the spoon position for over an hour and we were
never in a rush to separate.  
  
The year was 1971. I was 30 years old and Carrie was 36. We had been having
sex for over a year and at least twice a month. It was always anal with her
and in her favorite position but I never tired of it.  
  
IT BEGAN IN 1970  
  
Carrie was one of the corporate groupies at our company. This story takes
place in the 1970's, when everyone was sexually promiscuous and condoms were
rarely used. It was after a softball game that I first hooked up with her.
Carrie was a brunette with brown eyes, about 5'5" and 120 pounds. She was not
the prettiest of girls but she wasn't ugly either. She wore glasses, had brown
curly hair and kind of a homely look about her. She was no virgin and no
stranger to brief encounters or one night stands.  
  
That night after we had fucked in the missionary position, she rolled over on
her belly and put her ass on display. I caressed her ass, teased her between
the buttocks and searched for her nether hole. I finally reached the object of
my desire and I rubbed juice from her pussy into her asshole. She lifted her
hips slightly as I worked her firm ass cheeks. I pulled her buns apart
slightly and stared at the cute little aperture. I traced my finger over the
ridges of her now swollen sphincter and watched as it seemed to pulse and
throb under its own accord.  
  
I scooped more juice out of her pussy with my fingers and pushed it into her
ass. Carrie's hips bucked in response to my probing. I loved anal sex and I
loved to watch my cock slide in and out of a hot ass. I was hoping that she
was into anal sex. As my finger entered her channel she gripped it with her
sphincter muscle. I continued to finger fuck her ass adding more natural lube
from her pussy as needed and eventually I added a second finger. Her pussy was
sopping wet and offered plenty of natural lube. I had never seen any girl get
that wet.  
  
Satisfied that she was well lubed I straddled her hips and guided my slick
cock into her pussy to coat it with her juices and then I eased it into her
ass. My cock head slipped past the moistened sphincter and the spongy head
disappeared into her ass. Her anal ring snapped closed behind the cock head
and I marveled at the sight before me. I only had the head of my cock in her
and she lifted her hips and pushed back obviously wanting more but at the same
time cautioned me.  
  
"Not too deep at first and then go deeper," she whispered.  
  
My cock felt bigger than it ever had as I eased more of it into her anal
passage. I watched as it stretched her open and slid easily in her slippery
hole. I continued my slow penetration until the entire length of my shaft was
balls deep in her ass. Carrie gasped and grabbed the bed sheets as I hit
bottom and then moved her ass in time with my thrusts.  
  
"Let's fuck on our sides," she rasped.  
  
I rolled both of us to our left side and settled into the spoon position with
my cock still buried in her ass. My left arm came around and fondled one of
her tits and tweaked her nipples as my right hand sought out her pussy. I
pushed two fingers into her pussy as I fucked her ass and played with her
tits. Carrie was going wild as her orgasmic, constricting muscles gripped me
firmly.  
  
We fucked slowly as she arched her back and we fitted together perfectly. Her
gasps were intermittent and interrupted with cries and sobs of pleasure. Her
ass was so snug that I wondered how the semen would ever get out of my cock. I
fought to hold back my ejaculation as long as possible but the undulating
walls of her chamber were just too much. I felt the familiar build up in my
balls and I thrust into her as the first blast of cum exploded into her
rectum. I barely heard her pleas for me to fill her ass with cum as her
contractions milked every drop from my cock. I continued to fuck her slowly
and I enjoyed the new feeling of syrupy semen surrounding my cock in her
sheath.  
  
"I love the feel of your warm cum in my ass," she sighed as my cock remained
nestled in her hole.  
  
Carrie told me that she loved anal sex and that sometimes she actually
preferred it to vaginal sex. She said that she still wanted to cum and she
preferred a cock shooting a load in her ass while her clit and g-spot were
being rubbed. We remained in the spoon position for quite a while. I think we
even dozed and we were awakened when my deflated cock slipped from her ass.
Carrie rolled toward me and smiled as she whispered.  
  
"That was some great sex tonight, you are a good lover," she said softly and
then, "Come on it's time to get up and get dressed. We have to go to work
tomorrow."  
  
She was right and I never wanted to wear the same clothes to the office two
consecutive days. I took a brief rinse off, dressed and kissed her on the
cheek before I left. She knew I would not talk about us having sex together. I
had slept with several girls from the office and never said a word. I drove
home and went right to sleep after setting the alarm.  
  
SALVAGING A RAINOUT  
  
After that first time, we started hooking up at least twice a month. I was
also having sex with three other girls but I relied on Carrie for my anal fix.
I played on three softball teams with many of the same players on each team.
Our city was known for softball tournaments and I found myself playing in two
a month. They were always double elimination tournaments that usually began on
Saturday morning and wrapped up Sunday evening. The corporate groupies didn't
come to the weekend tournaments but in a couple of cases Carrie came with her
girlfriend Betsy whose boyfriend played on the team.  
  
Carrie and I would hook up after the games on Saturday and Sunday. At one
tournament, we got the morning games in but then the afternoon session was
rained out. The skies opened up and everybody dashed for their cars where we
hoped to wait out the rain and resume play. That one particular afternoon it
rained so hard that we could not see out the car windows. We decided to have
some fun to pass the time  
  
Carrie and I got in the back seat of my two-door Grand Am and I immediately
pulled down her shorts and panties. I lowered my softball pants and underwear
to my knees and the two of us played with each other for several minutes. The
Grand Am had louvered rear windows so it was impossible for anyone outside the
car to see in the back seat and besides no one was wondering about in that
storm. There was something very erotic about being partially clothed but still
having access to each other. Carrie had her legs spread wide as I fingered her
pussy and pushed her cunt juice into her ass. She stroked my cock with her
hand as I prepared her for another ass fuck.  
  
As I said earlier, I never knew anyone like Carrie who could get so wet during
foreplay. My hand was sopping wet and within minutes I had her anus coated
with her own pussy juice. I positioned her so that she was kneeling down on
the back seat and I knelt behind her. I put my cock in her pussy and let it
soak in her juices before I lined it up with her ass.  
  
Once again she reminded me with that familiar phrase, "Not too deep at first
and then deeper."  
  
I eased my cock into her ass as she maneuvered her body to accommodate the
anal penetration. She had her head down on the car seat turned to one side and
I watched her face grimace slightly as my cock made its way into her ass. She
moaned and groaned as I slowly fucked her going a little deeper in her ass
with each thrust. Once I was all the way in I picked up the pace and fucked
her until I flooded her ass with my cum. Carrie had her fingers buried in her
twat and she brought herself off as I plowed her ass. When my hips stopped
moving Carrie milked my cock with her sphincter and then her hips gyrated as
her own orgasm overtook her. I had to hold her tightly to keep my cock in her
ass as her hips jerked out of control.  
  
Suddenly it started to hail and the stones pelted the vinyl roof of my car. I
was prepared to fuck her ass again but she asked to wait until we got to her
place. It was obvious that the tournament was a washout for Saturday. I eased
my cock out of her ass. I knelt there looking at her recently violated nether
hole and watched as my semen trickled out of her rectum. Carrie remained still
for a few minutes with her shorts and panties around her knees and her ass on
display. I had some paper napkins in the car and she used them to wipe the
semen from her ass before she sat down on the car seat.  
  
We redressed and returned to the front seat. I noticed that all the cars were
gone except mine. The windows had steamed up so we waited until the defrosters
did their job. Then I drove to Carrie's place. Wasting no time, we went
straight to her bedroom. She flopped down on the bed and she was clearly in
the mood for more sex. I moved over to the bed and stripped her naked. I
removed her blouse and bra, her shorts and panties and her shoes. Then I
stripped down naked and got in bed with her.  
  
I rolled Carrie to her side and she knew what was coming next. I scoop her
female juice from her pussy and used it to lubricate her ass. She cooed as my
fingers probed her pussy and lubed her ass. Then I placed my cock in her pussy
just for few strokes to get it slick. I positioned my cock at her ass and
gently pushed my cock into her. This was our routine every time and each time
she would caution me with the same words as if I might forget.  
  
"Not too deep at first and then deeper."  
  
I always did what she asked and as I fucked her ass I went a little deeper
each time. Soon I was balls deep in her ass and I picked up the pace. For some
reason that afternoon, my cock felt longer and thicker than I could remember.
I reached around her with my left hand and played with her tits and rock hard
nipples. Next I moved my right hand to her pussy and pushed three fingers into
her. I quickly located her g-spot and soon she was going wild and creaming all
over my fingers. My cock was throbbing in her ass and I felt my pending
ejaculation building in my balls. One more deep thrust and I held my cock
there as I exploded in her rectum. My cock pulsated as streams of semen shot
into her ass. She instinctively clenched and unclenched my cock with her
sphincter. She milked every drop of cum from my cock.  
  
I stayed hard that evening and I kept right on fucking Carrie's ass. I knew it
would be a while before I could cum again, if at all, so I pulled out of her
ass and rolled her on her back. Then I pushed my raging hard cock in her pussy
and treated her to an exhilarating fuck. I kept my cock in constant contact
with her clit and I had her writhing and trembling as a continuous string of
orgasms rocked her body. Once has climax subsided, I pulled my cock out of her
pussy and rolled her back to her side and re-entered her ass. I pummeled her
ass as I sought out my third release orgasm of the day. Her ass was loose and
slippery from our combined juices but she was still snug enough around my
shaft. Once again, I stiffened and came in her rectum. I could feel my cock
pulsate again and even though the discharge was smaller the sensation was just
as rewarding.  
  
We lay still for a few minutes recovering from the intense fuck session. I had
forgotten about my cock in her ass until it had softened and slipped from her
hole. I felt my wet dick drop on my thigh and I knew that cum was trickling
out of Carrie's bottom.  
  
"Stay with me tonight," she whispered.  
  
"Sure, let's get cleaned up and call out for pizza, my treat."  
  
We showered separately and later ate pizza and watched TV. The rain had not
stopped so I called our team manager and he said the tournament might resume
Sunday afternoon or carry over to next weekend. I knew then that we could
sleep in the next morning and I was already thinking about morning sex.  
  
INSATIABLE SUNDAY  
  
In the morning I woke up with a raging piss hard-on and decided to treat
Carrie to a wakeup call. She looked so angelic sleeping on her back with her
firm tits poking up in the air and her hot pussy on display. I lined up my
huge erect cock with her receptive pussy and eased it in. Her face tensed with
the anticipation of my big cock filling her pussy. I loved to watch my cock
slide into a hot pussy and see the expression on my lover's face as the shaft
spread her wider.  
  
I fucked her slowly at first as I usually did and then I began to pick up the
pace. Soon I was pounding her pussy and fucking her into submission. Carrie
had mini orgasms as I relentlessly fucked her. I just kept at her with my piss
hard-on until she screamed and pleaded with me to stop. Her body convulsed in
a mind-blowing orgasm and then she went limp on the bed. I smiled to myself
and eased my cock out of her well fucked pussy. I got up and found the
bathroom to relieve myself and take a shower.  
  
As I was in the shower Carrie came in and joined me. We soaped each other and
my cock was rock hard at attention. She knew that I hadn't cum yet that
morning so smiling she told me to come back to bed. She was not into oral sex
either giving or receiving although she liked playing with my cock. She
grabbed a bottle of lotion from the bathroom and we returned to the bedroom.  
  
"Please massage me for a while," she said as she rolled over on her stomach.  
  
Carrie just sighed as I oiled up my hands, straddled her body and went to work
on her shoulders. She cooed as I rubbed the tension out of her upper body. I
worked my way down from her shoulders to her trap muscles and lower back. I
massaged her back just above her buttocks and she continued to coo and moan
with pleasure. I bypassed her ass for the moment and went to her calves. I
massaged each calf and worked my way up to the back of her thighs. As I
massaged the back of her legs my eyes were fixed on her well-fucked ass.  
  
I finally reached the object of my desire and I rubbed plenty of lotion onto
her buttocks. She lifted her hips slightly as I worked her curvy ass cheeks. I
pulled her buns apart slightly and stared at the cute little aperture. It was
hard to believe that my thick cock had been in that tiny hole so many times. I
traced my finger over the ridges of her now swollen anus and watched as it
seemed to pulse and throb under its own accord.  
  
I took the bottle of lotion and placed it right on her nether hole and let a
few drops fall on it. I pushed the lube in her ass and her hips bucked in
response. As my finger entered her channel she gripped it with her sphincter.
I continued to finger fuck her adding more lotion as needed and eventually
adding a second finger. Satisfied that she was ready, I straddled her hips and
guided my slick cock into her ass. My cock head slipped past the slippery
sphincter and the soft mushroom head disappeared into her ass. Her anal ring
swallowed my cock head and I marveled at the sight before me. I only had the
head in her and she lifted her hips and as always, she pushed back wanting
more.  
  
"Let's fuck on our sides," she rasped.  
  
I rolled both of us to our left side and settled into the spoon position with
my cock buried in her ass. She guided my left hand to her tits and I tweaked
her nipples as she guided my right hand to her pussy. I pushed three fingers
into her pussy as I fucked her ass and played with her tits. It was like a re-
play as we had done this so many times. She just loved to be butt fucked in
this position. Carrie was going wild again as her orgasmic, constricting
sphincter gripped me firmly. I felt the familiar sensation that began in my
toes and run up through my testicles. I thrust into her as the first of
multiple streams rocketed into her rectum. The gripping and clenching was
unbelievable as her sphincter strangled my cock. She pleaded with me to fill
her ass with cum as her contractions squeezed out every drop from my rigid
shaft. We remained still for a seemingly extended time. Once again, I enjoyed
the feeling of warm semen surrounding my cock in her bottom.  
  
As we lay in bed, I had the gentle pitter-patter of the rain outside. I knew
that the tournament would be rescheduled so I kept my cock in her ass as we
cuddled in the spoon position. We were in no hurry to get up and I knew that I
would fuck her ass again that morning before we finally did get out of bed.
After our second round of anal sex, we got up, showered dressed and went out
for breakfast. Following a leisurely breakfast, we returned to her pad and at
her request, I fucked her insatiable ass one more time.  
  
THE FINALE  
  
We continued our anal affair for several years before I had accepted a job
that required relocation. Carrie asked to hook up once more before I left. I
agreed and on a Friday night we went to her place. She wanted me to fuck her
ass in the spoon position and cum as many times as I could without removing my
cock. I knew that I could manage two ejaculations but probably not more in one
night.  
  
Sure enough we fucked for hours in the spoon position and I came in her ass
twice. I managed to stay hard but did not cum a third time. We fell asleep in
the spoon position with her ass pressed up against me. Sometime in the early
morning hours I got another erection and I slipped it back in her ass. I
fingered her pussy and played with her tits as I fucked her. She had another
massive orgasm but I did not cum again. We went back to sleep.  
  
Later that morning I woke up with my piss hard-on and this time Carrie
insisted that I fuck her ass in the spoon position again. I used her natural
juices to lube her rectum and then slipped my dick in her ass. My left hand
was playing with her tits and my right her pussy. This was the position that
she loved and I was determined to get her off as many times as possible. She
had multiple orgasms and the last one was somewhat violent as she screamed in
ecstasy and bucked so much that I could not keep my cock in her. My bladder
was ready to burst so I quickly headed for the bathroom. I must have urinated
for nearly three minutes, I had to go that bad.  
  
I returned to the bedroom and got back in bed with Carrie. It was my turn to
cum this time and I did filling her rectum for the last time. She cooed and
pulled my arms tightly around her as I shot several streams into her anal
passage. We stayed cuddled together letting my cock soften and slip from her
rectum. Minutes later I showered and dressed. Carrie said that she was going
to take a bath.  
  
During the years I was with the company I had slept with a number women. Many
of them were one night stands but a few were more than a couple of times.
Carrie had been one of my favorites mainly because of anal sex but also the
way she got off on it, particularly in the spoon position.




End file.

