


Discreet Anal Affair

by walterio



Category: Anal
Published: 2016-12-01
Updated: 2016-12-01
Packaged: 2017-04-29 06:36:36
Chapters: 1
Publisher: literotica.com
Story URL: https://www.literotica.com/s/discreet-anal-affair
Author URL:
https://www.literotica.com/stories/memberpage.php?uid=429765&page=submissions
Summary: Single guy and his boss have a special arrangement.
Erotica Tags: Anal Foreplay, Anal Sex, Discreet, Insatiable, Large Cock,
Lovely Body, Marvelous Ass, Mature, Oral Sex, Vaginal Sex
Average Rating: 4.52






        Discreet Anal Affair


PRELUDE  
  
Marcy was naked on all fours in the hotel bed. He head was on the mattress
turned to side and she was looking at herself in the mirror over the dresser.
At 37 years of age she was an attractive woman with a slender shapely 36-28-34
figure. Her breasts seemed large for her slender body but they were lovely. I
liked the way the nipples turned upwards. Her ass was to die for and she loved
anal sex. As I looked at her briefly before getting in bed, I took in the
lovely sight and her inviting ass. It was so gorgeous and seemed to call out
to be fucked.  
  
I get on the bed behind her and she passed the tube of gel back to me. She
loved me to get her ass ready for my cock and I loved the anal foreplay.
Kneeling behind her I positioned my 180 pound, 6'1" form so that I could have
access to her bottom. Marcy always douched her ass and pussy before we had sex
as she loved to be rimmed and have her pussy eaten.  
  
Placing my face between her curvy cheeks I dipped my tongue in her bottom and
licked her anus which caused her to squeal with delight. I licked her from her
clit to her tail bone, pausing at the rubbery ring to probe it with the tip of
my tongue. She had a mild orgasm as she always did with our foreplay. Then it
was time to prepare her ass for my rock-hard cock.  
  
I squeezed and ample amount of gel directly on her anus and pushed it in past
the twitching aperture. With one finger, I lubed her passage and then added a
second digit. Satisfied that she was well greased, I applied some gel to my
cock and then positioned it at the entrance. I pushed the spongy soft mushroom
head of my 7" pecker against her anus and it opened up to receive me. I paused
briefly allowing her to adjust to the penetration before continuing my
journey. Although we had anal sex countless times, Marcy always cautioned me.  
  
"Nice and slow, not too deep at first and then deeper."  
  
I had always been careful with her and took my time with the anal penetration.
The way her clenching sphincter gripped me was exciting but it was the view of
my dick sliding in and out of her gorgeous shapely ass, that was incredibly
erotic. My hips moved slowly as I gradually fed more and more of my cock to
her. Eventually I was all the way in and my pubes made contact with her
buttocks. As she loosened up, I picked up the pace and caressed her lovely
bottom as I drilled it. Her cheeks would jiggle when my hips hit them each
time.  
  
It didn't take long for me to cum as this was such a turn-on. My body tensed
up and I felt my release build in my toes and the sensation was incredible. I
exploded in her rectum which she always loved. Marcy had told me that she
loved the feeling of semen shooting into her rectum. Since it was first
ejaculation of the day, it was voluminous and I fired six or seven rounds into
her bottom. I leaned over her and held her lovey large breasts as she worked
her sphincter milking my cock dry.  
  
"I need you in my pussy now," she whispered with some urgency.  
  
I eased my still stiff dick out of her shapely bottom and she flipped over on
her back. At 28 years of age, I could maintain my erection through my first
two ejaculations and I could cum a third time after a recovery period. Marcy
spread her legs and I quickly filled her womb. She loved being fucked with her
ass full of cum. She told me that it felt like she had two cocks in her.  
  
My cock filled her pussy and she moved under me rubbing her clit against the
shaft. It didn't take long for her to orgasm and when she did it was as
intense as ever. She pulled my upper body down, wrapped her legs around my
lower torso and buried her face in my shoulder. Her entire body trembled and
shivered with her climax and she used my shoulder to stifle her cries of
ecstasy. I continued to move my cock in and out causing her to cum again
before I ejaculated in her pussy. We held to each other for several minutes
before separating and lay side by side on the bed.  
  
I got up and got some drinks for us out of the mini bar. We sat up in the bed
and sipped our drinks before we relaxed enough to talk. We chatted about the
client presentation tomorrow briefly. Marcy was a Managing Partner in our firm
and she would do the introductions before turning it over to me. I was a
Senior Analyst and close to becoming a Junior Partner in our firm. After about
an hour we were ready for more sex.  
  
As was our routine, I took care of her pussy one more time. After that we
cuddled in the spoon position and fucked her ass again. After I came a third
time, we both showered and cleaned up in the bathroom before I dressed and
went to my own hotel room. We would meet for breakfast and then proceed to the
client site.  
  
THE FIRST TIME  
  
The very first time Marcy and I had sex together was impromptu because neither
one of us had been with anyone in the office. It was considered taboo to be
having sex with co-workers and frowned on by management. So, when Marcy, a
managing partner, came onto me, I was stunned. We had had a successful client
call that day and had landed a significant engagement.  
  
When we checked into the hotel that evening, we learned that they had fouled
up our reservations. There was only one room booked. Speaking with the manger,
he did the best he could and gave us a suite. It was late, as we had stopped
for dinner first, so Marcy decided we would stay in the suite for that one
night. She had consumed a fair amount of wine over dinner and seemed a bit
tipsy and even flirtatious.  
  
When we got to the room, she wanted to have a night cap before unpacking and
settling in. I got two after-dinner cocktails from the minibar and went down
the hall to get some ice. When I returned to the room Marcy was seated in the
upholstered chair with her feet up on an ottoman. I poured her drink and
handed it to her and then sat on the pull-out sofa.  
  
Marcy sat back in the chair and stretched her back and shoulders. Her mini
skirt rode up and her long pretty legs were displayed. She was a very fit
woman who worked hard to stay in shape. She jogged all the time and did
hundreds of crunches to keep her tummy flat. She was a slender lady at 5'7"
and weighed about 130 pounds. Her tailored suit showed off her curves but she
always looked very professional. I guessed her measurements to be 36-28-34 and
I learned later that it was a very good guess.  
  
She had light brown hair that she kept cut short in a pixie style and dark
brown alluring eyes. I never looked at her sexually but for 37 years old she
was pleasant to the eye. She was well educated and very smart. Marcy had been
married and divorced twice because her husbands were fucking around. After the
second divorce, she dated but she never got in a serious relationship again.  
  
"Let's get undressed and then finish our drinks," she said catching me totally
by surprise.  
  
"You want us to get us undressed?" I questioned, not believing that I heard
her correctly.  
  
"Sure, why not? Our clothes are going to come off soon anyway," she replied
with a smile.  
  
"You can't do this. You're playing with fire," I thought to myself.  
  
In spite of the risk, I was all for it as I was anxious to get a look at her
naked and check out her curvy ass. We undressed and we checked each other out
at the same time. Marcy smiled when my underwear came off and she saw my cock
in its flaccid state hanging between my legs. I anxiously waited until she
turned her back to me so that I could see her fabulous ass. She turned to put
her clothes on the chair and I was treated to a view of her amazing bottom. It
was perfectly shaped seemed to reach out toward me. I secretly hoped that she
liked anal sex.  
  
"You know I don't do this. I mean that I don't sleep with company employees."  
  
"I don't either," I assured her.  
  
"So, we can make an exception this time but I need your promise to be
discreet."  
  
"You have my word."  
  
"Good I am glad that you agree," she said and then took another sip of her
drink, "Let's take this into the bedroom."  
  
She put her drink down on the nightstand, smiled at me and reached for my
cock. "You have a nice cock," she told me just before she took it in her
mouth.  
  
I leaned back as her very skilled mouth got me hard within minutes. I put my
drink down and put my hands in her pixie hair as her head bobbed up and down.
Satisfied that I was sufficiently hard, Marcy mounted me and lowered her
dripping wet pussy onto my cock. She looked me right in the eye as she started
to ride me and I knew that she was in desperate need of an orgasm. I reached
up and played with her big tits and tweaked her hard nipples as she rode me.
Marcy was breathing hard and rapid as she approached her release. I looked
into her eyes and I could see the lust in them. Then she exploded.  
  
"Oh my God, oh my God, oh, oh, hold me," she screamed as her climax rocked her
body.  
  
She rode me through her orgasm and I felt my cock swimming in her pussy. Marcy
then collapsed on my chest for several minutes until she composed herself.
When she lifted herself off my cock I heard a distinct sucking sound as my
cock was released from her pussy. We rested for several minutes, sipped our
drinks and chatted easily. Then we began playing with each other again and
when I found her G-spot she came again. She held my hand tight to her pussy as
she humped it vigorously. She stiffened and screamed as another orgasm rocked
her.  
  
"No one has ever found that spot as quickly as you did," she gasped and then
requested, "Fuck me from behind this time."  
  
She rolled over on all fours, put her head down on the bed and raised her
curvy ass in the air. I wanted to just drive my cock in her ass but I knew it
would be better for her to warm up to it. I still didn't know if she liked
anal sex. I knelt behind Marcy and slipped my cock into her pussy from behind.
I fucked her slowly and then I began to play with her ass. I caressed the
shapely globes and teased her anus with my finger. I scooped up some of her
pussy juice and rubbed it into her anus. She wiggled her ass in response so I
took it to the next step. I pulled my cock out of her pussy and ran it up and
down the crack of her ass. Then I paused at her nether hole and prodded it
gently with my rigid cock.  
  
"Oh, where's the cream?" she cooed sexily.  
  
I knew then she was going to let me have her ass. I hopped out of bed and
dashed to the bathroom and quickly located the body lotion supplied by the
hotel. Hurriedly I got back in bed behind her and thoroughly coated her anus
with the lotion. I put gobs of lotion on my cock making it as slippery as
possible. My cock was as slick as oil and I eased it into her ass. It slid in
like a hot knife through butter and eventually I buried it to the hilt in her
ass.  
  
She emitted a gasp as my cock slid in all the way. I plowed her ass and fucked
her rapidly in search of my much needed release. She eventually began to move
her hips in an attempt to match my thrusts and it was obvious that she was
turned on by the anal sex. She was gasping and grunting as I began to really
pummel her ass. I picked up the pace even more and held to her shapely
buttocks as our hips slapped noisily together. She was really into it now and
the two of us fucked like maniacs.  
  
"Oh yeah that's it, that's the way to fuck my ass. Give it to me, cum in me,
cum in my ass,"  
  
I couldn't believe that I was in the ass of a managing partner in our firm.
Not in a million years would I have thought that I would be fucking my boss
and never would have I expected to be in her lovely ass. Not only that but she
was begging for it. I didn't know what would happen after that night but I was
really into it and not concerned about the consequences. We were both sweating
from the physical intensity of our butt fucking. I slammed into her as my cock
now moved freely in her bottom. I felt my release approaching and as much as I
wanted to prolong the ass fucking session, I couldn't. My body stiffened and I
plunged my cock all the way into her gorgeous ass. Streams of semen shot into
her rectum as I seemed to cum continuously for several minutes.  
  
"Oh yes, I feel it. Fill me up, fill up my ass," she cried out and then anther
orgasm hit her, "Oh shit, here it is, I'm cumming!"  
  
Her body thrashed around as I held onto her curvy ass cheeks and kept my cock
buried in her ass. Her fingers flew over her pussy and clit as my warm seed
flooded her anal passage. She then collapsed face down on the bed and my cock
slipped from her bottom with an audible pop. I knelt over her as my cock
dripped the remaining semen onto her curvy buttocks. She wiggled her bottom
and squealed in delight. I moved back from her and I admired her shapely ass.
She looked so sexy that I rubbed her bottom lovingly and she clenched her
buttocks. She then rolled over on her back and spread her legs for me.  
  
"You made me so hot, come here and eat my pussy."  
  
I moved my head between her legs to eat her pussy but first I kissed and
licked around the area and her inner thighs. I breathed warm air right on her
snatch and she grabbed my head and pulled it to her cunt. I pulled my head
back off and let my fingers trail to her pussy. I lightly rubbed her outer
cunt lips and she twitched with each touch. She moaned as her clit responded
to the stimulation and slowly exited its hood looking for attention.  
  
I placed my fingers on her cunt lips and trapped her clit between them and it
became swollen and stood erect. She squirmed in pleasure while I moved her
pussy lips up and down on her clit and she shuddered from the extreme arousal.
Still moving her cunt lips up and down, I bent down and kissed her clit. She
jerked and bucked as my lips touched her upright nub. I drew my head back a
bit and again blew air directly onto her clit as she writhed and bucked again,
moaning with pleasure.  
  
I moved my arms behind her knees and raised her hips up. I put her legs over
my shoulders and I lowered my mouth to her pussy and kissed it as though it
were her mouth. She groaned with delight as she waited for my next advance. I
drew my tongue along her outer labia, up one side and down the other without
touching her clit.  
  
"Suck it please, please lick it, oh please! Don't stop."  
  
I flicked my tongue across the edges of her pussy as she quivered and seeped
her juices from between the lips. I licked the juices from the edges telling
her she tasted delicious. She was nearly mad with desire as she begged me to
pleasure her with my tongue. I parted her labia with my tongue and licked the
insides of her cunt lips, nibbling each one a little and then sucking on them
both. She whimpered and moaned when I suddenly plunged my tongue as deep as I
could into her pussy. She screamed with delight as my tongue explored the
insides of her pussy.  
  
Instinctively, she grasped my head and pulled it into her cunt, begging me to
lick and suck her. I did not disappoint her as I swirled my tongue around her
engorged clit and back into her sopping wet cunt. She was constantly moaning
as my lips closed about her clit and sucked her clit in and out of my mouth.
Writhing and gyrating she exploded in another powerful orgasm, drenching my
face and mouth with her copious juices. She seemed to cum with each spasm of
her body. I did not let up sucking her clit and she tried to push my face away
as she cried out.  
  
"Oh stop, please stop. I can't cum anymore let me rest."  
  
Her body shuddered through yet again another orgasm and she lay there gasping
and breathing heavy as her crescendo abated. Finally, her climax subsided and
she embraced me and kissed me. I knew that she could taste her own juices on
my lips and I plunged my tongue into her mouth taking her breath away. By now
my cock was rock hard again and I moved between her legs. I eased my cock into
her sopping wet pussy and she wrapped her legs around my torso.  
  
"My, we are fired up this evening, aren't we?"  
  
"That's your doing," I replied and I began to fuck her gently.  
  
Slowly, I moved into her. Marcy opened beneath me, enveloping my penis
tightly. Her cunt was like a fist as she clenched her vaginal muscles. She
squeezed me as I moved within her.  
  
"Your cock feels so good in me. I love it."  
  
I thrust into her deeply and I felt the head of my cock pressing against her
cervix. I felt her vagina contract around my cock. She trembled with a shudder
and a long moan as she urged me on. I grabbed her hips in my hands and began
to thrust in and out as I pounded her pussy. My heavy bloated testicles
slapped against her ass as my cock drove into her hot pussy.  
  
The bed was now rocking with the force of our fierce, animalistic fucking. Her
legs clamped around my waist. Her pussy grasped my cock, squeezing it and
milking it as I fucked her. I moved my hips against hers and buried my cock to
the hilt within her. Her quaking pussy was drenched with her juices as I
rocked my cock slowly, grinding the head against her cervix. I felt my orgasm
building in my balls and I knew that any second I would be spewing my seed
into her womb. I felt my semen travel from my scrotum through my cock as I
came deep inside her flooding her waiting warmth with my load.  
  
Neither one of us could speak as the pleasure was so intense. I collapsed on
her and she wrapped her arms and legs even tighter around my body. I kissed
her neck and she sighed aloud then I kissed her on the lips and our tongues
dueled briefly. Not wanting to crush her I rolled off her as my cock deflated
and slipped from her cum filled cunt. After a few minutes, I stirred and
thought to move to the pullout sofa in the other room.  
  
"Stay with in me in the bed tonight," she whispered.  
  
"Are you sure?"  
  
"Yes, I want your body next to me tonight."  
  
We never did unpack our luggage that evening. The next morning I was lying on
my side next to Marcy who was also on her side. She was cuddled up in a spoon
position with her bottom pushed into my crotch and my morning piss hard-on was
tucked between the cheeks of her ass. I reached around and cupped her big tits
with my hands. With one hand, I trailed it down her body and found her pussy.
I inserted a finger into her quim and diddled her clit until she rolled to her
back. Her pussy was soaking wet again as I mounted her and slid my cock into
her. She just moaned with her eyes closed as I began the ritual of fucking her
with my morning hard-on. I fucked her through multiple orgasms until she
begged me to stop and let her rest. I pulled out of her and went into the
bathroom with my erect cock pointing the way.  
  
"Come back to bed after you go to the bathroom."  
  
I relieved myself and then returned to bed as she had asked. She had me lie on
my back as she positioned her head near my cock. She then proceeded to give me
one fantastic blow job. I was very turned on and I knew that I would blow my
load quickly particularly with her skill at oral sex.  
  
"Let me know when you are going to cum."  
  
I felt my release building from my toes to my cock and I let her know that I
was really close. She took my cock from her mouth and stroked it with her
hand. Her pace quickened as my cock seemed to get harder and thicker. With her
other hand, she cupped my bloated balls and fingered my perineum. That did it
and my body stiffened as cum shot out of my cock. She kept jerking me off as
she watched rope after rope of semen shoot out of my cock and land on my chest
and stomach. She kept working my cock until the remaining seed was just oozing
from my cock head and trickling into my pubic hair.  
  
"I wanted to watch you cum that time."  
  
It was time to get up and get going. Marcy showered while I unpacked my
luggage. I set up the ironing board and iron in the suite. When she finished
her shower, I took mine and she unpacked her things. We pressed our clothes,
packed, dressed and then ate breakfast in the hotel coffee shop. That morning
we had a late morning sales call and then it was off to the airport for our
flight back home. We never discussed our sexual encounter that day or at the
office the following week. I assumed it was a one-night stand and that it
would not happen again. I could have never been more wrong.  

ROUND TWO AND MARCY'S STORY  
  
On a Thursday, she called me into her office and asked me if I wanted to join
her for a weekend in wine country. I was surprised but since I had no plans
for the weekend, I accepted. She had been wanting to visit Napa again and she
knew that I liked wine as well. I knew it would be more than wine that I would
be tasting that weekend. She asked me if I would be willing to drive and I
did. We left L.A. late Friday afternoon and arrived at a Napa Valley Inn that
evening.  
  
After checking in and getting settled we had some wine and cheese in the wine
bar. It was plenty for us as we were not that hungry that evening. The cheese
served was delicious and the red wine was excellent. We had serval glasses of
wine and I could tell that Marcy was feeling it.  
  
"I shouldn't drink so much wine. It always makes me feel in the mood for sex,"
she whispered across the table.  
  
"Exactly what I hoped would happen."  
  
We returned to our room and promptly peeled the clothes off each another.
Marcy got in the bed and lay back as I took in her beauty. She was in great
shape and always looked desirable. I sat on the side of the bed and stroked
her shapely legs and luscious thighs. My hand drifted up to her mound and I
felt that she was wet with desire. She smiled at me as I fingered her pussy
and licked my fingers clean of her juices. She opened her arms and welcomed me
into her body. I slipped between her thighs and slid my hard cock into her
moist pussy. Marcy uttered an audible gasp as I filled her womb. I began to
move slowly and eased my cock almost all the way out of her pussy before
plunging it back in. She was lost in the lust of the moment.  
  
"Oh yes, that's it love me," she whispered.  
  
Just hearing her asking me to make love to her was a turn-on for me and I
picked up my pace. Marcy threw her hips up at me as if to try and get me
deeper in her womb. I felt my orgasm approaching but I didn't want to cum
before she did so I tried to slow down.  
  
"No, no don't stop, go faster, I'm so close," she begged.  
  
I picked up the pace again as we both raced toward our climax. It was
difficult to determine who came first because but Marcy wrapped her long legs
around me and humped me for all she was worth as I spurted my seed deep in her
womb. We continued to grind into each other until we couldn't move. I propped
up on my elbows to keep my weight off of her and moved my hips slowly. My cock
was swimming in our comingled juices.  
  
"I love being with you. Thanks for coming with me this weekend."  
  
"I'm the one who is thankful. You are one amorous lady."  
  
I rolled off of Marcy and lay next to her on the bed. She smiled at me and
then snuggled in closer. We talked for the next several. As I lay next to her
I caressed her breasts, neck and arms, teasing her skin with my fingernails
and tongue. She made a low, drawn out sound. Deciding that I'd teased her
enough I started on her naked breasts. As I sucked her warm flesh into my
mouth and rolled a nipple between my teeth, she let out a moan of pleasure.  
  
Marcy then moved down the bed, gently took hold of my cock and took me into
her mouth, rolling my cock around and getting it wet with her saliva, while
her hand worked my shaft up and down at the same time. Seconds later, she
straddled me. Her hand wrapped around my now slippery cock and I felt the
tickle of her pubic hair just before her soft flesh nudged my helmet and then
it was suddenly engulfed by the heat and tightness of her pussy. She loved to
ride my cock and I loved being in her.  
  
Marcy grabbed hold of the top of the head board on either side of my head as I
held onto her hips. She rocked her hips back and forth, pressing downwards and
working the walls of her pussy as I slid into her further. The next motion of
her hips caused her to gasp in pleasure as my full length penetrated her. She
began to work up and down, back and forth as she moaned in pleasure. She
wanted to last as long as possible and the unhurried pace felt sensuous and
wonderful. She continued to ride me at a slow, even pace as I relaxed and let
her take charge. As she fucked herself on me I could hear the smacking and
sucking sound of her pussy as my cock moved around inside her.  
  
Her big breasts jiggled when she picked up the pace. She pushed her hips down
until our groins met and then lifted up until just the swollen tip of my cock
remained inside her. She knew just how far to move so that my cock never
slipped out of her pussy. Her thigh muscles felt firm and tight under my hands
as she worked her body on me. The speed of our groins slapping together
increased as we fucked faster and harder. We really had our rhythm going now
and I thrust up into her as she lowered herself on me. Her pussy contracted
around my cock as her eyes fluttered and she emitted a high pitch scream.
Marcy grabbed onto my shoulders as she rode out her orgasm.  
  
"Oh, I love to cum like that. Did you cum too?"  
  
"No, not this time but I'm fine for now."  
  
As I lay by her side I noticed that her tits were standing straight up and her
aroused nipples were pointing at the ceiling. I tweaked the hard nubs between
my fingers causing her to gasp and quiver.  
  
"My breasts are very sensitive; you know that I love that."  
  
I leaned over and kissed her breasts and sucked on her sensitive nipples. I
rubbed her firm flat tummy as I sucked on her tits and her rock-hard nubs. I
was still hard and ready to fuck some more.  
  
"Oh I love that it makes me feel so feminine and sexy."  
  
As I sucked her tits and continued to rub her belly, I let my hand drift down
to her wet pussy. I ran my fingers through her soaked pubic hair. She asked me
to let her rest as she was sure that she could not possibly cum again. I
rolled her onto her stomach and played with her shapely ass. I let my fingers
dance lightly over her buttocks and I tickled her tailbone. She was going
crazy with the light touches and squealed when I kissed her ass cheeks. My
cock was rock hard and ready so I lifted her hips to a level with my cock as I
knelt behind her. I eased my cock into her pussy and began to fuck her doggy
style. Marcy was content in this position since I was not in contact with her
clit. I slammed into her from behind causing her curvy ass cheeks to jiggle.
As I fucked her from behind I looked at her tight anus and I just had to have
it again.  
  
I scooped up gobs of her pussy juice and smeared it in the crack of her ass
spreading around her nether hole. I added saliva to my finger and probed her
tight aperture with the tip of my finger. She cooed softly when she felt my
finger probe her asshole. I gathered up more juices and added more saliva as I
continued to probe her hole and open her up. I gently pushed a very well
lubricated finger into her ass and the tiny aperture opened up to accept the
digit. More saliva and more juices greased her asshole sufficiently to allow
me to slide my finger all the way into her rectum.  
  
Marcy knew that I was preparing her ass for my cock and she reminded me, "You
know to be gentle when you fuck my ass."  
  
"Don't worry, I will."  
  
I eased my cock into her ass and I heard her gasp as I penetrated her. She
quickly adjusted to my cock and I soon had a smooth rhythm going. I loved
watching my cock slide in and out of her shapely ass as I caressed her lovely
buttocks. Now with my cock in her ass I was approaching a second ejaculation.
I could feel it build in my balls, travel through my scrotum and splash the
insides of her rectum with my warm semen. I flooded her beautiful ass and then
pressed forward leaving my cock in her. I stayed in position behind her as she
milked my cock with her sphincter. I waited until my pecker softened and
slipped from her ass before I moved away.  
  
She smiled at me as she cuddled up close and I wrapped my arms around her. We
were good lovers together even though she was nine years older than me. I
never looked at her as an older woman but a competent business woman who was
an outstanding lover. We talked in a low voice just above a whisper.  
  
"When did you get into anal sex?"  
  
"It was I worked in D.C. I was a year out of college and I went drinking with
some co-workers after work on a Friday evening. I had too much to drink and
these two guys took me to their apartment. One had me suck his cock and the
other fucked me in the ass. I lost my anal virginity that night."  
  
"Wow, did you like it or was it painful for you?"  
  
"It was somewhat painful but I was so drunk I didn't feel too much pain. They
switched places after the first guy came in my ass. The other guy also came in
my ass and I kind of liked the sensation of it. Both guys had normal size
cocks that weren't too thick. I don't think I could have handled a cock your
size the first time."  
  
"So, after that night, you took to anal sex?"  
  
"After that weekend, I did. It was wild. They both fucked my ass twice on
Friday night. Then on Saturday they fucked me all day and each of them came in
my ass three times. Sunday was more anal sex and by time I headed home my ass
was well broken in. After that I like anal but I was always selective about
with who I did it."  
  
"That is wild. Did they ever take care of your needs?"  
  
"Oh sure, they fucked my pussy and made me cum all the time. They just never
came in my pussy, always my ass."  
  
We cuddled and fell asleep in the spoon position, my favorite. I was trying to
visualize Marcy with two guys getting butt fucked continuously. We both slept
soundly.  
  
A WEEKEND IN NAPA VALLEY  
  
I woke up Saturday morning before Marcy and I used the bathroom to relieve
myself. I would have fucked her with my piss hard-on and drive her wild but
the pressure in my bladder was extreme. It had to be all the wine and water I
drank the night before. I came out of the bathroom and she was awake. She
smiled at me in her naked glory and patted the bed indicating that I should
lie next to her. She then moved between my legs and my cock started to stiffen
in anticipation. Marcy wrapped one hand around its girth and looked up at me
with those daring eyes. She then tilted her head back down and brought her
mouth towards my cock. She ran her tongue up its smooth underbelly and I
groaned aloud.  
  
Holding it with her hand she sank her open mouth down onto my cock. Her lips
closed around it and I felt her hot, wet tongue go to work. She sucked me hard
and her cheeks hollowed as she worked her head back and forth. I gasped and
put my fingers into her soft brown hair to guide her head back and forth.
Marcy knew what she was doing to me as her pace slowly quickened and her right
hand worked my shaft. Her left hand cradled my bloated balls and softly
stroked them. She then ran her finger along my perineum. She loved to get a
reaction out of me. My large cock bulged in her firm grip and felt even larger
than normal. She worked her hand back and forth letting it glide smoothly
around my cock then she looked up at me and smiled.  
  
I moaned again as her tongue snaked forward and tickled the tip of my cock.
Her tongue found the pee hole and she licked the pre-cum as it oozed out of my
slit. She worked her tongue in circles around the tip of my cock and took my
length deeply into her mouth again. I watched as almost the full length of my
cock vanished into her mouth. Marcy then swirled her tongue around the shaft
buried in her mouth. I closed my eyes and groaned in pleasure as her head
worked back and forth more quickly clasping my shaft with both hands as her
head vigorously bobbed up and down.  
  
Her pace was relentless and I held her head gently as I felt my orgasm
building in my testicles. Marcy allowed my cock to plop out of her mouth again
and a thin trail of saliva stretched from my cock to her lips. She smiled
again and caught the saliva in her hand as her eyes fixed on my cock. Her hand
wrapped tightly around it again and she proceeded to jerk me off me at a
steady pace occasionally licking the head of my cock and nibbling it with her
teeth. I threw my head back. Closed my eyes and groaned out loud. She jerked
me off slowly. There was a distinct look of lust in her eyes as she stared at
my cock and her hand moved up and down the shaft.  
  
"I love playing with your cock," she sighed and then asked, "Are you going to
cum for me? Are you close?" she asked in a sexy voice.  
  
I just nodded yes since I was indeed very close. She then took me back in her
mouth and ran her tongue around my shaft again. Then her head bobbed up and
down again as she pursed her lips and hallowed her cheeks. That did it for me.  
  
"Marcy I'm cumming," I warned and then I grunted as I came in her mouth.  
  
She heeded my warning and removed my dick from her mouth. She stroked it with
a look of lust in her eyes. I shot waves of semen into the air and it landed
on my chest and pubes. She squeezed my cock with her hand so that every drop
oozed out. As the intense sensations passed from my body I relaxed a little
and looked down to watch her suck my cock. She was now kissing it, licking up
and down the shaft as if she were making love to it. My cock softened in her
mouth and she took it in her hand as she licked the final remnants of my
ejaculation from the slit.  
  
"I'm in the mood for anal, you can take my ass this morning," Marcy said in a
sexy tone.  
  
I was anxious to get at her ass again. I moved her to all fours with her ass
elevated and she placed her head on the mattress turned to one side so she
could see me. I started playing with her pussy and her curvy ass lubricating
her asshole with her own cunt juice. Marcy moaned and cooed as I fingered her
pussy and her asshole simultaneously. I got off the bed to retrieve the lotion
from the hotel bathroom. As I did I was thrilled that Marcy was indeed going
to let me fuck her in the ass the first thing that morning. I returned to the
bed and put an ample of amount of lotion in her asshole coating the tiny
puckered opening of her anus and lubricating the rim.  
  
I added my saliva to my lotion covered cock and nestled my dick against the
entrance of her rectum momentarily before easing it inside her ass. I could
feel my cock struggle to stretch the resistant muscles. My dick head burrowed
in and her rigid passageway soon yielded to the determined action of my cock.
Marcy moaned as my penis filled her hole. I was glad that she blew me first so
that I would last longer in her bottom.  
  
"Go slowly, let me adjust again," she said sexily as she placed her hand on my
thigh.  
  
I fucked her with long and deliberate strokes until my cock was sliding easily
in and out of her ass. I caressed her shapely buttocks as I watched my penis
move in and out of her rectum worming around inside of her curvy ass. I
caressed her tits and tweaked her nipples as I leaned over her body and
whispered in her ear.  
  
"Marcy you have a hot ass, I always love fucking you in your hot ass."  
  
My hands freely roamed her body and I pulled her hips drawing her backwards
impaling her on my inflated member. I reached for her pussy to finger fuck her
and diddle her clit but I found Marcy's hand already there. Suddenly I felt my
cock inside her ass swell up and I started pumping faster. Within minutes I
knew that she felt the warm fluid being squirted inside her anus and she
immediately started to cum herself. Her cunt walls convulsed around her own
hand as her sphincter squeezed every drop from my spurting cock. I grunted as
my whole body became stiff and I slammed my cock harder into her. Marcy
writhed around and her body arched off the bed as a climax of massive
proportion tore through her loins. She then lay on her back, splayed her legs
and pulled back the folds of her vagina.  
  
"Here eat my pussy, please eat my pussy."  
  
I rolled over and got between her legs. I put her thighs on my shoulders and
lowered my mouth to her pussy. I took one slow lick as I flattened my tongue
on Marcy's mound. It felt so smooth and warm and I knew I had achieved the
desired effect from her moan I know that she enjoyed it, she always did. I
enjoyed the taste of her and I kept licking and eating her. I pointed my
tongue and burrowed into her pussy as it parted her labia my tongue was
rewarded with the exquisite taste of her love juice.  
  
She reached down with both hands and spread herself wide making it easier for
my tongue to explore her pussy. She was breathing rapidly and she cried out
whenever I got near her hard pearl. As I searched out her stiff clit still
just barely hidden she tensed and began to quiver. I felt like I had teased
her enough and it was time to see her reaction when I nibbled her clit.  
  
I burrowed my tongue as deep into her as I could and then I just sort of
licked and sucked my way up. I used the very tip of my tongue to push back the
little hood. I flicked my tongue over it once and then explored the folds of
flesh on either side of it. Marcy was now moaning and she used her fingers to
pull her hood back as she arched herself so that her pearl stuck out even
further like a little cock. I nuzzled it with my nose taking in her scent and
I licked it once more before I took it between my teeth and gently nibbled it.  
  
She went wild and started bucking and moaning loudly. She pulled my head to
her pussy as she cried out in ecstasy. I sucked her clit as deep in my mouth
as I could and she humped my face for all she was worth. I sucked harder and
played with her wonderful clit with my lips, tongue and teeth until finally
she pushed me away and collapsed on the bed, her body shaking. I lay next to
her and stroked her body my hands moved freely over her tits and pussy mound.
She rolled toward me and embraced me and yelled for me to hold her tight.  
  
"God I love waking up with you in the morning and starting the day off with
fantastic sex," she told me and then said, "Let's get cleaned up and grab some
breakfast and visit some wineries."  
  
We ate a light breakfast in the hotel and then headed for the wineries. We did
two wine tours and then stopped in Calistoga for lunch. After a leisurely
lunch we stopped at two more wineries before heading back to the Inn. We
purchased wine to bring home and also enjoy in our room. We had eaten a late
lunch so we opted for more wine and cheese that evening in the lounge. It was
nearly 8:00 PM when we returned to the room.  
  
We took off our clothes and wore the Inn's supplied bathrobes. It was sexy
being naked under the robes. I opened a bottle of wine and we relaxed in the
sitting area. I sat on the sofa at one end and Marcy sat at the other end with
her feet stretched out toward me. She mentioned that her feet were a little
achy from all the walking so I offered to massage them. She placed one foot in
my lap and I massaged it for her. She offered me the other foot and I massaged
that one as well.  
  
I then worked her calves and she cooed in delight as her muscles relaxed under
my touch. She slid down closer to me so that I could have access up to her
knees. I rubbed the calf of one leg while the foot of the other leg remained
in my crotch. She took a sip of wine and tilted her head back and closed her
eyes. I worked all the tension out of one calf and then started to work on the
other one. She kept her eyes closed and her head tilted back as I massaged her
shapely legs. Occasionally she would pick up her head, sip some wine and smile
at me before closing her eyes again.  
  
I let my hands move up to her thighs and massaged her quads. Marcy flinched at
the first touch of her thighs but she quickly relaxed and let me work out the
kinks. As I massaged her thighs I pushed her robe up higher and I could see
her bare pussy. I let my hands wonder all over her thighs and I massaged her
inner thighs as well. She kept her eyes closed as I massaged her thighs and
caressed the naked skin. She shivered and opened her eyes to stare at me. She
knew exactly where this was going. I ran my hand over her bare pussy and her
hips jerked in response.  

Marcy was breathing hard and her voice cracked when she spoke again, "Don't
start something that you don't plan to finish."  
  
"Oh I plan to finish this alright."  
  
I pushed her robe up to her hips and leaned over to kiss her creamy thighs.
She gasped aloud at the touch of my lips to her naked skin. I could smell the
sweet aroma of sex that was given off by her pussy as my face moved closer to
her crotch. I lifted her legs to my shoulders and kissed her inner thighs just
below her pussy. She groaned with pleasure as she reached down with her hands
to control my head. I tickled her outer lips with my fingers and then let them
slip inside her vagina.  
  
She was so wet that two of my fingers slid in easily and she unconsciously
relaxed her grip on my head. I moved my mouth toward her and closed over her
pussy shoving my tongue into her wetness. She cried out and grabbed my head
again but this time she held it tight to her quim. I lapped at her pussy as I
fingered her with two fingers. I spread her pussy lips apart and located her
throbbing clit. Marcy was really excited as her erect clit looked like a teeny
dick sticking out. I sucked on her hard clit and she bucked her hips up into
my face. I reached under her and cupped her shapely ass cheeks in my hands as
I drove into her pussy with my tongue and nibbled on her clit.  
  
"Ooh, ooh, I'm cumming. Oh hold me, hold tight," she screamed as she lost it.  
  
The climax rocked her body and I held on for dear life as she thrashed,
twisted and bucked all over the sofa. I kept right on eating her pussy and I
held onto her shapely ass as she thrashed about. She slowly calmed after her
intense orgasm and I continued to lick her until her pussy was dry. As we lay
on her sofa I continued to lick and kiss her bare thighs as she ran her hands
through my hair.  
  
"That was a great cum. Now it's my turn."  
  
I opened my robe and she moved between my legs as my cock started to stiffen
in anticipation. Marcy wrapped one hand around its girth and looked up at me
with those daring eyes. She then tilted her head back down and brought her
mouth towards my cock. She ran her tongue up its smooth underbelly and I
groaned aloud. Holding it with her hand she sank her open mouth down onto my
cock. Her lips closed around it and I felt her hot, wet tongue go to work. She
sucked me hard and her cheeks hollowed as she worked her head back and forth.
I gasped and put my fingers into her soft hair to guide her head back and
forth.  
  
She knew what she was doing as her pace slowly quickened and her right hand
worked my shaft. Her left hand cradled my balls and softly stroked them. She
then ran her finger along my perineum. Marcy took my cock from her mouth and
blew on the head of it. I felt her breath cool the saliva on my cock and I
clenched my butt in pleasure. My large cock bulged in her firm grip and felt
even larger than normal. She worked her hand back and forth letting it glide
smoothly around my cock then she looked up at me and smiled. She knew the
effect she was having on me and she seemed to enjoy every moment of my
torment.  
  
I moaned again as her tongue snaked forward and tickled the tip of my cock.
Her tongue found the pee hole and she licked the pre-cum as it oozed out of my
slit. She worked her tongue in circles around the tip of my cock and took my
length deeply into her mouth again. I watched as almost the full length of my
cock vanished into her mouth. She then swirled her tongue around the shaft of
my cock that was buried in her mouth. I closed my eyes and groaned in pleasure
as her head worked back and forth more quickly clasping my shaft with both
hands as her head vigorously bobbed up and down.  
  
Her pace was relentless and I held her head gently as I felt my orgasm
building in my testicles. This was definitely the best blow job I'd ever had
in my life, bar none. Marcy allowed my cock to plop out of her mouth again and
a thin trail of saliva stretched from my cock to her lips. She smiled again
and caught the saliva in her hand as her eyes fixed on my cock. Her hand
wrapped tightly around it again and she proceeded to jerk me off me at a
steady pace occasionally licking the head of my cock and nibbling it with her
teeth. I threw my head back. Closed my eyes and groaned out loud. Marcy jerked
me off as fast as she could as her hand almost became a blur as it moved up
and down my shaft. There was a distinct look of lust in her eyes as she stared
at my cock  
  
"Marcy here it cums," I warned and then I grunted as I came in her mouth.  
  
My eyes closed tight as I ejaculated in her mouth. I felt my cock pulsate as
rope after rope of semen shot into her mouth. As the intense sensations passed
from my body I relaxed a little and looked down to watch Marcy suck every drop
from my cock. She was now kissing it, licking up and down the shaft as if she
were making love to it. My cock softened in her mouth and she took it in her
hand as she licked the final remnants of my ejaculation from the slit. Once
she was satisfied that she had emptied my cock she ran her tongue around her
kips and swallowed one final time. Marcy let out a big sigh and stood up and
kissed me deeply.  
  
I leaned over to nuzzle her and I whispered in her ear, "That was incredible
it felt so good."  
  
Marcy looked into my eyes and smiled as she said, "I love sucking your cock."  
  
"You drained me," I sighed deeply.  
  
"I'm sure that with your youthful recuperative powers that you'll be ready to
go again tonight. Let's go to the bedroom."  
  
I walked behind her and watched her buttocks undulate under her robe. It was
then I decided that I had to have her ass that night. First I would take care
of her pussy again. Marcy dropped her robe and climbed in bed and with seconds
I was in her pussy fucking her senseless. The bed started rocking with the
force of our fierce animalistic fucking. Her legs clamped around my waist as
she screamed her release. Her pussy grasped my cock, squeezing it and milking
it as I fucked her carefully. Her quaking pussy erupted into orgasm again as I
rocked my cock slowly, rubbing the head against her cervix. I felt my orgasm
building in my balls but I wanted to save it for her ass. With all my will
power and control I held off cumming in her womb.  
  
I rolled her over on her stomach. I caressed her ass and teased her between
her ass cheeks. I searched for her nether hole as I massaged her bottom. I
finally reached the object of my desire and I rubbed juice from her pussy into
her anus. 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 rubbery ring 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. Marcy's hips bucked in response to my probing. I loved anal sex and I
loved to watch my cock slide in and out of her hot ass. As my finger entered
her channel she gripped it with her rubbery sphincter. I continued to finger
fuck her ass and then added the lotion that was still on the night table.
Satisfied that she was well lubed I straddled her hips and dipped my slick
cock into her pussy to coat it with juices and then I eased it into her ass.
My cock head slipped past the moistened anus 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.  
  
"Not too deep at first and then go deeper," she reminded me as she always did.  
  
My cock felt thicker than it had the whole weekend as I eased more of it into
her anal passage. I watched as it stretched her open and slide easily in her
slippery snug hole. I continued my slow penetration until the entire length of
my shaft was balls deep in her ass. Marcy 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 urgently.  
  
I rolled both of us to our left side and settled into the spoon position with
my cock 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 and located her G-spot as I fucked her ass and played
with her tits. She 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 it seemed to keep me from cumming. I fought to hold off my
ejaculation for as long as possible but the gripping action of her rectum was
just too much. I felt the familiar tension 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 warm
semen surrounding my cock in her sheath.  
  
"I love the feel of your hot cum in my ass."  
  
We remained in the spoon position for several minutes. I think we even dozed
off and we were awakened when my deflated cock slipped from her ass. Marcy
rolled toward me and smiled. We cuddled for a long time before we separated
and fell into a deep sleep.  
  
On Sunday morning, we had sex again and then we cleaned up, dressed, packed
and left the Inn early. We stopped in a few wineries did a little tasting and
purchased a few cases to take back to our homes. Marcy thanked me for a great
weekend. I in-turn thanked her and after dropping her off and helping her with
the wine, I drove to my place. It had been a wonderful enjoyable weekend with
great sex. It was the start of our affair that would carry on until I was
recruited by another firm and left the L.A, area.




End file.

