


Office Sex is the Best

by walterio



Category: Erotic Couplings
Published: 2009-03-13
Updated: 2009-03-13
Packaged: 2017-04-27 15:19:18
Chapters: 1
Publisher: literotica.com
Story URL: https://www.literotica.com/s/office-sex-is-the-best
Author URL:
https://www.literotica.com/stories/memberpage.php?uid=429765&page=submissions
Summary: Five year affair between an executive and his assistant.
Erotica Tags: Anal Sex, Cum Swallowing, Dildo Usage, Large Cocks, Lesbian Sex,
Oral Sex, Rimming, Seduction, Sticky Buns, Threesomes
Average Rating: 4.57






        Office Sex is the Best


_Author's note: This is a story about an office affair between a married man
and a married woman. If infidelity, cheating and unfaithfulness upset you,
please don't read this story. The story also contains anal sex and bisexual
encounters which may not be to your liking. In the past I have received
feedback that I should be upfront about the content of a story so that the
reader is not caught off guard, which is why, I have explained the content of
this story._  
  
INTRODUCTION  
  
In 1984 I had just completed a strategic information technology plan for a
major corporation in the Chicago suburbs. I was working for a prominent
consulting firm at the time where I was a senior manager. I had been working
with the consulting firm for ten years and I was very close to being made a
partner. Prior to the planning engagement I had traveled extensively for the
firm and sometimes I was gone for months at a time. The traveling was getting
old which is why I was receptive when the client CEO asked me to consider
joining his company. He wanted me to take over the information technology
division and implement the strategic plan that had just been approved by the
board.  
  
I knew why he made the offer. The IT division was a mess and there was serious
doubt that the existing management could turn things around much less
implement a new strategy. It was a lucrative offer as I would be a Senior VP
and an officer of the company. The compensation package was loaded with
incentives and it was very attractive. If I accepted I would be compensated
just as well as if I was named partner with the consulting firm and I would
not have to travel extensively.  
  
I had a concern however that it might be perceived that the consulting firm
would be viewed as sabotaging the existent IT management. The CEO agreed with
me and we worked out a plan. First he would make the call on the existing IT
management and then he would bring me in as an interim CIO to provide
oversight. In six months he would then make me the offer of employment
assuming that was what we both still wanted. So we proceeded with that
approach and two weeks later I was brought in as the interim CIO.  
  
The previous CIO had an administrative assistant named Cathleen who was
nervous about the transition. I put her mind at ease and explained that she
was not in danger of losing her job. Cathleen would function as my assistant
for the next six months and if I was to accept the job, I could decide then if
she was the right person to be my assistant.  
  
The first six months were hectic in turning around a very difficult situation.
I had to make many changes in management and staff. During this transition
Cathleen proved herself to be very loyal and capable of handling confidential
and sensitive information. I worked long hours and a 60-70 hour work week had
become the norm. Then the CEO approached me again and told me the offer still
stood. He said that I had impressed the rest of the executive team and that he
wanted to bring me on board. I accepted the position and joined the firm.  
  
In 1984 I was 43 years old, married with two children in college. I was 6'0"
tall, weighed 190 pounds and I was very fit. I was an avid tennis player,
golfer, skier, SCUBA diver and in a martial arts black belt program. Cathleen
was 35 years old and married to a 40 year old man. She had short blond hair
with a 34-25-35 figure. At 5'5" and 120 lbs. she was small breasted and her
best asset was her ass. She was solidly built and exercised regularly and in
excellent shape. Cathleen was not a beautiful girl but she was attractive and
dressed very tastefully. She never wore tight fitting clothes or mini skirts
so unless you saw Cathleen in her aerobic outfit you wouldn't see her figure.
She took aerobics two nights a week at a studio that was on a different floor
in our building. Aerobic class started at 5:00 PM so Cathleen would change at
4:30 PM and go to class. She would return to the office after aerobics and
work until about 7:00 PM each Tuesday and Thursday. She remained in her
leotards and it was then that I noticed her firm body and figure.  
  
An Executive retreat was scheduled in November and I was on the agenda to
provide an update on the IT turn around and objectives. Cathleen worked late
with me preparing for the retreat and it was during that time that we seem to
grow closer although nothing sexual had happened or was ever suggested between
us. The retreat was at a plush Chicago hotel and on the second evening a
cocktail party was scheduled. All the Executive's administrative assistants
were invited to the cocktail party in recognition of their hard work.  
  
The retreat was very successful and everyone liked my presentation and plans
for the following year. After the second day of meetings it was time for the
cocktail party. Everyone was in good spirits and enjoyed themselves at the
social. The company dinner was held on the first night and on this night it
was just cocktails and appetizers. Stations were set up for different types of
food along with two bars in the small ballroom. Cathleen looked good that
evening as she had worn a tasteful black one piece evening pantsuit.  
  
Later in the evening I noticed that it was obvious that Cathleen had too much
to drink. I followed her to the ladies room when I noticed that she staggered
slightly. I waited until she came out of the ladies room and noticed that she
still had trouble walking. She stumbled slightly and I caught her before she
fell. Then I took her up to my room to let her sleep it off as she was in no
condition to drive. I placed her on the bed and being worried about her
getting sick; I removed her one piece black pantsuit. As I looked at her in
her bra and panties I could not resist removing those as well. Her breasts
were small and cute and she had a little tuft of blond hair above her pussy.
She appeared to be passed out and I started to leave the room when she called
out.  
  
"Wait, don't leave me alone," she said softly in a somewhat slurred tone.  
  
"I'll come back in a few minutes," I assured her and then I returned to the
cocktail party.  
  
I wasn't sure what I was going to do with her when I returned to my hotel
room. I thought to call her husband but there was no answer at her home.
Cathleen had told me that her husband often went out with people from work and
he would often come home drunk. She also had shared with me that he was using
coke now and that he was getting stoned a lot. So when he wasn't home I
assumed that he would be useless to Cathleen that night. I put my thoughts
aside and continued to socialize with the other executives until we called it
a night.  
  
I went back to my room and as I looked at Cathleen's nude form on the bed, I
decided to join her. I knew I was crossing the line and I thought about that
saying, "Don't dip your pen into the company ink," but I took off all of my
clothes and approached the bed anyway.  
  
THE ONE NIGHT STAND  
  
As I knelt on the bed with my cock in a semi-erect state, Cathleen rolled
toward me and said, "Oh, I am glad that you are back," and she surprised me by
taking my cock into her mouth.  
  
Within minutes she had me rock hard proving that she was an accomplished cock
sucker. I was anxious to get at her ass all the while wondering if she would
let me fuck her in the ass. I loved anal sex and fucking beautiful shapely
asses. I always tested the water with the women with whom I went to bed. 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.
Cathleen moaned and cooed as I fingered her pussy and her asshole
simultaneously. I tried to get her asshole wet enough with her juices and my
saliva so that I could fuck her ass.  
  
Cathleen had not objected to the ass play so I knelt behind her and tried to
insert my cock in her ass but it just wouldn't go in. Afraid of hurting her I
tried more pussy juice and saliva for lubrication but to no avail. My 8" long
and 5" around cock just would not go into her tight ass. There are times when
my cock feels bigger and this was one of those times. I was fingering
Cathleen's ass when she spoke.  
  
"Use some cream," she said urgently.  
  
Well if there is one thing plush hotel rooms have is plenty of shampoo,
conditioner and body lotion. I got off the bed to retrieve the lotion from the
bathroom. As I did I realized that Cathleen was going to let me fuck her in
the ass. 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 anus 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.
Cathleen moaned as my penis filled her hole.  
  
"Go slowly at first it has been awhile," she said sexily.  
  
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 cock
move in and out of her rectum worming around inside of her curvy ass. I
caressed her small tits and tweaked her nipples as I leaned over her body and
whispered in her ear, "Cathleen you have one hot ass, I love fucking you in
your hot ass."  
  
My hands freely roamed over her body and I pulled on 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 Cathleen's hand already buried
in her womb. She was frigging herself frantically working herself toward an
orgasm. Suddenly I felt my cock inside her ass swell up and I started pumping
faster. Within minutes I knew that Cathleen felt the warm fluid being squirted
inside her anus and she immediately started to cum herself. Her cunt walls
convulsed around her own hand fucking her cunt as her anal muscles squeezed
every drop from my spurting cock. I grunted as my whole body became stiff and
I slammed my cock harder into her. Cathleen writhed around and her body arched
off the bed as a climax of massive proportion tore through her loins.  
  
My cock slipped from her ass with an audible pop and I flopped down on the bed
next to her. She surprised me when she covered my cock with her mouth and
sucked any remaining cum from my tool. Cathleen then lay on her back, splayed
her legs and pulled back the folds of her vagina.  
  
"Here eat my pussy, please eat my pussy," she pleaded.  
  
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 Cathleen's mound. It felt so smooth and warm and I knew I had achieved the
desired effect from her moan I know that Cathleen enjoyed it. 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 juice. Soon having no reservation I was licking and
lapping up as much as I could as fast as I could.  
  
Cathleen was obviously enjoying what I was doing as she reached down with both
hands and spread herself wide making it so much easier for my tongue to
explore her pussy. Cathleen was breathing rapidly and she moaned softly
whenever I got near her hard clit. As I searched out her hard clit still just
barely hidden she tensed and began to quiver. After I felt like I had teased
her opening as much as I could with my tongue it was time to see her reaction
when my tongue finally touched that treasured pearl.  
  
I burrowed my tongue as deep into her as I could and then I just sort of
licked and sucked my way up. When I got to her clit I used the very tip of my
tongue to push back the little hood. I was truly amazed at its size. I flicked
my tongue over it once and then used the tip to explore the folds of flesh on
either side of it. Cathleen was now moaning and she used her fingers to pull
her hood back as she arched herself so that her clit 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.  
  
Cathleen went wild and started bucking and moaning loudly. She let go of her
own fleshy hood and 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 Cathleen humped my face for
all she was worth. I was excited that I was able to get her that excited and I
sucked harder and played with her wonderful clit with my lips, tongue and
teeth. I don't know exactly how many times Cathleen came but finally she
collapsed on the bed, her body in spasms.  
  
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.  
  
"Hold me, oh please hold me," she pleaded as her orgasm and spasms continued.  
  
I had never seen anyone cum that hard before and I was briefly worried that
she had injured herself. My fears were short lived when she finally calmed
down and spoke to me.  
  
"That was incredible I haven't cum like that in a long time. You really know
how to eat pussy," she said with a sigh.  
  
We lay there for awhile making small talk and then Cathleen started stroking
my cock. Now at the age of 44 it was very unusual for me to cum more than once
in a fuck session, particularly after having more than a few scotch on the
rocks. In fact I usually could stay hard for a long time before my first cum
which allowed me to pleasure my partner thoroughly before achieving my own
orgasm. Cathleen added some body lotion as she kept stroking me cock and soon
had me hard again.  
  
"I like playing with your cock. You have a big cock," she told me.  
  
"It's not that big," I replied although I was very comfortable with my
manhood.  
  
"It's bigger than Jerry's and the biggest I have ever had," she said with a
sultry tone. I knew that Jerry was her husband.  
  
"Well there are plenty bigger than mine," I assured her.  
  
We continued our conversation as Cathleen continued to stroke my cock. I
learned that she had first been ass fucked before she was married to Jerry.
Cathleen was working downtown Chicago at the time and she went out with two
guys from the office. They took her back to their place and one fucked her ass
as she blew the other guy. She took to ass fucking after that but she was very
selective about who allowed in her ass. Jerry did not like butt fucking and he
also had lost interest in eating pussy, so now it was either blowing Jerry or
occasional vaginal sex. She also told me that this was the first time she had
sex with some other than Jerry since they were married.  
  
I told her about my sex life too. My wife did not like oral or anal. She
didn't even like to sit on my cock so with her it had been straight missionary
sex for twenty plus years of marriage. I had had flings on the road when I
traveled for business but up to now I never did when I was home. I loved women
with great legs and shapely asses and anal sex was my favorite although I
always made sure that the woman was pleasured.  
  
"All this talk and playing with your cock has got me hot again. I need to sit
on your dick," she announced.  
  
Cathleen straddled my body and lowered herself onto me as she held my tool and
aimed it at her vagina. My hard cock slid easily into her womb and she emitted
a small gasp as it filled her hole. Cathleen rocked back and forth on top of
me as I held on to her curvy ass. I stroked her ass cheeks and molded her firm
buttocks in my hands as she picked up the pace fucking herself on my dick.
Cathleen started moaning as she fucked faster and faster. I sensed her pending
orgasm and then she yelled out.  
  
"I am going to explode. Oh, Oh hold me, please hold me tight," she screamed.  
  
Cathleen collapsed on top of me her body quivering from the intensity of her
orgasm. I could feel her juices coating my cock as it remained buried in her
womb. It took a few minutes for her to regain her composure and she just lay
on me and cooed. Eventually she rolled off of me and lay on her back next to
me. I let her stay in the room that night as I was still afraid to let her
drive home alone.  
  
The next morning I woke up first and looked at the Cathleen lying next to me
in bed. It was hard to believe that I had fucked my admin assistant last
night. She looked so angelic sleeping on her back with her cute firm tits
poking up in the hair and her hot pussy on display. I eased her legs apart and
lowered my mouth to her vulva. I teased her with my tongue until her pussy
heated up and glistened with moisture. She started to stir and reached down to
her pussy to find my head between her legs. She opened her legs wider giving
me easier access to her luscious pussy.  
  
I located her clit and brought a soft moan to her lips as I nibbled it gently.
I then inserted a thick finger into her pussy and continued to tease her hard
clit. Her pussy was getting wetter and wetter and she started to move her hips
with a desire to cum. That was the signal that I was waiting for and I moved
my body up and knelt between her legs. I lined up my erect cock with
Cathleen's sopping wet cunt 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 cock spread
her wider.  
  
I fucked her slowly at first and then I began to pick up the pace. Soon I was
pounding her pussy and fucking her into submission. Cathleen had orgasm after
orgasm as I relentlessly fucked her. I just kept at her with my piss hard-on
until she screamed and pleaded with me to stop. Cathleen's 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 went into the
bathroom to relieve myself and take a shower.  
  
As I was in the shower Cathleen came in and joined me. We soaped each other's
bodies and my cock was rock hard at attention. She knew that I hadn't cum yet
that morning so with a smile she dropped to her knees and took my cock in her
mouth. She only took about five inches in her mouth and stroked the rest of it
with her delicate hand.  
  
"Let me know when you are about to cum. I want you to cum in my mouth," she
told me.  
  
I just nodded and told her that I was close. Cathleen kept sucking me and
jerking me off until I put my hand on her head as a signal that I was close.
She took me deeper in her mouth and jerked me off with her hand. Cum flew out
of my cock and sprayed the back of her throat. She pulled my cock out and let
my remaining cum splash against her tits and neck. The shower water washed the
semen away as quickly as it hit her body. Several ropes of cum shot out of my
cock she squeezed the remaining seed out then took my cock back in her mouth
and sucked me dry.  
  
Cathleen stood up, kissed me and then said, "Wow that was a good load."  
  
We got out of the shower and dried off. Cathleen put on a robe supplied by the
hotel as I got dressed. I left the room and told Cathleen to wait until about
10:00 AM before she left the room. I told her that the other admin assistants
would most likely assume that she had slept off her hangover. I joined the
other executives for a continental breakfast and then we wrapped up the
retreat. The retreat went until 4:00 PM and after that I returned home.  
  
The next day everyone returned to work and Cathleen and I went about business
as if nothing ever happened between us. I wasn't sure if we would ever get
together again. I assumed that we wouldn't and that it had been a case of both
of us having too much to drink and letting our guard down. I was satisfied
with the one night stand as it had been great sex. For the next several weeks
Cathleen and I didn't even speak of the one-night stand.  

THE AFFAIR IS REKINDLED  
  
As I noted earlier, Cathleen participated in aerobics held in the building on
Tuesday and Thursday evenings. Often after aerobics she would come back to the
office and finish up some administrative tasks. She would still be dressed in
her leotards which showed off her firm legs and shapely ass. It took all my
restraint not to touch her hot looking bubble butt. One day Cathleen came to
me and asked if we could stay late one evening and go through a large number
of file cabinets. She told me we were running short of space but she did not
want to throw anything out without checking with me. The best night for her
would be either a Tuesday or Thursday after aerobics. I agreed and we set the
date for the house cleaning.  
  
The following Thursday after aerobics Cathleen and I tackled the project of
cleaning out the files. It was a huge task and took us several hours but we
emptied about twenty file drawers. Most of the stuff was old IT material that
could be tossed. As we worked that evening it was hard for me to keep my eyes
and hands off of Cathleen's butt. I was tempted to risk it and touch her but I
thought better of it. I was always concerned about sexual harassment in the
work place. Cathleen then surprised me.  
  
"Will we ever do anything like we did in Chicago again? And don't tell me that
you don't know what I am talking about," she challenged.  
  
She caught me totally off guard and I replied, "I thought that may have been a
case of both of us drinking too much and getting carried away. Since you
didn't say anything before now I left it alone. I would love to get together
again if you are sure that is what you want."  
  
"It is definitely what I want. We had great sex that night and it was the best
in years," she whispered.  
  
We wrapped up our work and went over to the local hotel bar to get something
to eat. The bar was known for the best burgers in the area. The parking lot
was in back and it could not be seen from the street. Cathleen and I had
burgers and a couple of beers before calling it a night. During our meal we
discussed how we could get together in the future and the importance of being
discreet.  
  
After our meal I walked Cathleen to her car and she asked me to get in for a
minute. Well we there longer than a minute as she proceeded to give me a
fantastic blow job. She unbuckled my belt, unbuttoned my trousers and pulled
them along with my boxers down to my ankles. As Cathleen pulled my boxers down
over my balls she licked and sucked them before kissing her way up my shaft.
Looking up into my eyes, she slid her lips over my bulging head with her hand
still wrapped around my shaft. Her tongue swirled under the ridge of my crown
as she sucked me deeper into her mouth. She tested her gag line and was soon
taking my entire cock down her throat.  
  
My cock was alive and my hot flesh pulsed against her lips. She pulled me
deeper into her mouth, pressing her lips tightly against me and sucking hard.
The feel of my hard cock sliding between her lips and over her tongue had me
on the verge of a huge orgasm. Cathleen had slipped her hand into her leotards
and fingered her dripping pussy. The smell of sex was rampant in her car.  
  
I grabbed the back of her head and started fucking her face. She was slurping
and sucking as fast as she could. Cathleen drooled as she tried to keep up
with my thrusting motions. Her fingers dug into my thighs, moving her head as
I pumped my cock in and out of her mouth. I knew her pussy needed attention
but I wasn't about to stop anything she was doing. I could sense that I was
going to cum soon and I warned her but she just kept sucking me in
anticipation of receiving a creamy treat. I felt my cock swell and knew that
she was about to receive my load. Muffled moans escaped from her throat as she
eagerly sucked my dick awaiting her prize. She moved her lips up and down over
my shaft in rhythm with my thrusting motions. She was drooling like crazy and
I could feel it running down my pecker onto my balls.  
  
My breathing became more erratic and I was about to lose control. Cathleen
looked up at me with those big eyes and nodded her head, letting me know she
wanted to taste my seed and then covered my cock with her mouth just as I lost
it. I let out a soft grunt as I pumped stream after stream of hot cream into
her mouth. I shot the first jet against the roof of her mouth then several
more blasts of hot cum poured into her mouth. She moved her hand under my
scrotum to squeeze out the last few drops and then Cathleen had her orgasm.
Apparently the feel of my throbbing cock in her mouth, the taste of my seed
and her hand in her cunt was just too much. The pressure in her lower tummy
gushed out through her pussy and soaked her fingers.  
  
My cock fell from her lips and cum dripped from her lips and chin as her body
jerked and shuddered in orgasm. Cathleen looked up at me when she was done,
blotches of cum glistened on her lips. The smell of pussy in the car was
powerful. I took Cathleen's hand and licked her fingers clean. I pulled my
shorts and trousers back up and dressed the best I could in the confines of
her car. We said good night and I went to my car feeling totally drained as I
drove home.  
  
THE AFFAIR CONTINUES  
  
That night started our torrid affair and over the next several weeks we would
get together on Tuesday and Thursday evenings after aerobics at a hotel.
Typically the evening went like this; Cathleen would suck my cock and I would
eat her pussy, then I would fuck her pussy and finally her ass, cumming in her
ass. We also brought sex into the office on days when we would not be meeting
later at the hotel. Cathleen would give me marvelous blow jobs in my office.
She loved to suck my cock and swallow my load.  
  
One day Cathleen brought in some documents for me to sign. She walked around
to my side and placed the papers on the desk. As she leaned over to point out
the signature line I let my hand slide up her leg under her skirt. I stroked
her nylon encased leg all the way up to her ass. Cathleen smiled and then went
over to the office door and closed and locked it. Then she returned to my side
and assumed her previous position.  
  
I fondled her ass for awhile and then I lowered her pantyhose and panties to
her knees. I kept a tube of lotion in my desk and I lubed up her bottom and
fingered her ass. I played with her pussy as I fingered her ass and she
squirmed on my hands and fingers.  
  
"Yes, play with me. It feels so good. Make me cum, make me cum," she repeated
over and over.  
  
And cum she did soaking my hand with her female juices. She had to cover her
mouth to muffle her moans of ecstasy. Then after she composed herself she had
me stand up and she knelt in front of me. Cathleen unbuckled my belt and
lowered my pants to the floor. Then she slowly pulled my boxer shorts down my
legs. She loved it when my erection got caught in the waistband of my boxers
and my cock would spring forward as it cleared my shorts. Cathleen then sucked
my cock until I came in her mouth.  
  
Cathleen always wore long loose fitting skirts in the work place so I decided
she needed to shed the panty hose and wear something more appropriate for sex
in the office. I brought a Victoria's Secret catalog into the office one day.
Cathleen stood by my side as we looked at the catalog on my desk. As she paged
through the catalog, I stroke her legs and ass again through the pantyhose.
Then I lowered her hose and panties and played with her naked ass and pussy
again. Cathleen came on my fingers again and then she gave me one of her
wonderful blow jobs.  
  
Cathleen selected a couple of items form the catalog to replace her panty
hose. That day at lunch time we went over to the Victoria's Secret store in
the nearby mall and purchased nylons for her that had thigh high elastic tops.
We also picked out some crotch less pantyhose that were very erotic. The panty
hose had a waistband and two side panels attached to the stocking part. When
Cathleen wore the new pantyhose her ass and pussy were bare and her ass looked
great framed in the hose. Cathleen started wearing both the thigh high
stockings and the crotch less pantyhose to the office along with sexy panties.
It was very erotic when I slid my hands up her stocking covered legs to her
bare skin just above the elastic tops. I would caress her bare skin before
cupping and fondling her ass cheeks. Then I would remove her panties slowly
dragging them down her legs and by the time I touched her pussy she was
sopping wet. Cathleen would move to the chair in my office and place her legs
on my shoulders as I ate her pussy and fingered her asshole. She would have
intense orgasms and coat my face with her pussy juice. Then we would finish
with another one of her signature blow jobs.  
  
SEX IN THE CAR  
  
A couple of times Cathleen would need a ride home because one of their cars
was in for repairs and Jerry would take the available car. We would work late
into the evening and then drive to her house in the dark. As we drove I looked
at Cathleen as she shifted in her seat pulling her dress up showing more of
her upper thighs and the elastic tops of her stockings. She smiled as she
gradually opened her legs more giving me a glimpse of her inner thighs. Then
she reached under her dress and removed her panties.  
  
As I reached across the car seat Cathleen arched her back a little then spread
her legs further apart, giving me access to her genitals. My fingers began
slowly teasing her clitoris and then caressing the folds of her labia. My
index finger pushed its way between the textured folds to pause over her
sensitive bud and it caused an involuntary gasp to escape her lips as she felt
the gentle touch. Her legs jerked slightly to allow my hand easier admittance
to her vagina as I pressed my hand between her trembling thighs and gently
kneaded the soft flesh of her slippery vulva. I continued to wiggle my finger
about inside her juicy passageway before her groin started to clench and spasm
sporadically. I could feel the warm fluid seeping from her aroused sex and I
forced my hand harder against her cunt. Cathleen gave a muffled cry, clamping
my hand between her legs against her pussy, as the orgasm slammed into her.  
  
My arousal was clearly evident as the bulge at my pelvis was enormous with my
dick straining at my trousers. As her orgasm subsided Cathleen couldn't resist
reaching into my lap and squeezing the hardness beneath the fabric of my
pants. She fondled my stiffened cock and then slowly traced the outline of her
lips with her tongue. Cathleen reached for the zipper of my pants and tugged
it downward, putting one hand inside the gap to retrieve my engorged organ.
Then she slowly lowered her head to flick the top of my penis with her tongue.
I released an involuntary sigh as the she took in as much of my cock as she
could and then returned to lick the head, lapping away at a trickle of pre
cum.  
  
Cathleen continued sucking vigorously on the length of my shaft as my orgasm
erupted. My hips jerked uncontrollably as I struggled to keep control of the
car but she never released her grip. She swallowed all of my creamy discharge
and when I eventually stopped cumming she pulled her head away. Some of my
fluids dribbled down the side of her mouth but she quickly swiped it away with
the back of her palm and licked it clean.  
  
I pulled up in front of her house minutes after cumming in her mouth. "I am
really enjoying these rides home," she teased.  
  
"As if I don't," I retorted.  
  
Cathleen got out of the car and I drove back to my home. What a ride that had
been!  
  
Another night after aerobics, we went to the bar for a couple of drinks. After
a few drinks we adjourned to my car so that Cathleen could suck me off. As she
was blowing me she pushed her leotards down to her knees baring her ass and
pussy. I played with her ass and fingered her pussy as she sucked on my cock.  
  
She lifted her head up and said, "I wish you could fuck me in the ass
tonight."  
  
I asked her if she had any lotion and she dug it out of her purse. I reclined
the passenger seat all the way until it was almost flat and had her lay face
down. I prepared her ass with the lotion and my saliva. I pushed my trousers
and undershorts down past my knees, lubed up my cock and got on top of her. It
was tight quarters but I managed to get my cock into her ass and started
banging her hard. Cathleen pushed up at me as hard as I pounded her. Soon we
were both sweating and breathing hard. We made quite a sight if someone should
happen to look in the car window but we were past caring about that as we
raced toward our mutual orgasms. As soon as my spunk filled Cathleen's ass her
body went into spasm with her own orgasm. I lay on top of her keeping most of
my weight off of her until we recovered. We cleaned up the best we could and
headed home.  
  
THE ROMANTIC INTERLUDE HOTEL  
  
I started to get a little nervous with us using local hotels for some of our
encounters. So far so good that no one had recognized us but I started to
worry a little. Many of the vendors that called on our company used local
hotels and I did not want to be spotted by any of them or anyone else that
would know us. I mentioned this to Cathleen and she suggested a place called
La Chateau. It was not as well known as a more popular romantic interlude in
the area and La Chateau was in a secluded area. I had heard the name but I
knew very little about it. La Chateau was a romantic interlude that had a
variety of rooms to suit one's taste. The room that Cathleen and I liked the
best contained a Jacuzzi, water bed and mirrored walls. All of the rooms
contained TVs with adult entertainment as well. The Chateau added to enjoyment
to our sexual encounters.  
  
The first time we went to The Chateau was memorable. We entered the room and
wasted no time taking off our clothes as the Jacuzzi filled with hot water and
bath gel. Cathleen and I showered together before entering the Jacuzzi. We
soaped each other up and played with each other's bodies being careful we
didn't cum in the shower. Cathleen then would douche both her pussy and her
asshole. It was the first time I had ever seen a woman do that and it was kind
of erotic.  
  
After showering we entered the Jacuzzi armed with a bottle of wine. I turned
on the jets and we kicked back enjoying the bubbles and our first glass of
wine. After awhile Cathleen leaned back into me and I reached around and
stroked her cute titties tweaking and rolling her nipples in my fingers. I
slid one of my hands down across her firm abs over her little blond tuft of
hair and found her vagina. I played with the folds of her labia and then
inserted my fingers in her pussy. I found her hard clit and rolled it between
my fingers as I continued to tease her nipples with my other hand.  
  
As Cathleen got turned on I moved her to the other side of the Jacuzzi and I
had her lean over the edge presenting her shapely ass to me. Her ass always
looked good but this time it glistened with water and bath gel and looked so
sensual. I leaned over and licked Cathleen's pussy from behind driving her
wild. Then I had the urge to tongue her beautiful ass so I swiped my tongue
from her pussy up and over her bung hole and back to her pussy. She gasped out
loud when my tongue touched her asshole. I really got into it and grasped both
of her curvy ass cheeks and pulled them slightly apart so that I could get my
tongue in deeper. I probed her pink aperture with my tongue as I inserted
three fingers in her pussy. She started whimpering, gasping and directing the
action.  
  
"Oh my God, do it again. Lick my asshole; stick your tongue in there. Eat my
pussy, tongue my ass, rim me, oh yessssss," she cried out.  
  
I grabbed the bottle of wine and poured some in the crack of her ass letting
it trickle down over her anus and pussy. I placed my mouth on her and drank up
the wine swabbing her pussy and ass in the process. I repeated this several
more times until Cathleen seemed to go into convulsions with her first orgasm
of the evening. She collapsed back into my arms and I stroked her smallish
tits as she recovered from the intensity of her orgasm.  
  
"Not in my wildest dreams did I ever think that you would ever tongue my ass
or did I know it would feel so wonderful," she uttered in an exhaustive voice.  
  
"I surprised myself by going after your ass. I have never done that before but
it just looked sexy as it glistened with water. Of course I remembered that
you had douched and it looked so clean. I think I have found a new way to
drink wine," I told her.  
  
We decided to get out of the Jacuzzi before we turned into prunes. We dried
off and flopped down on the water bed. Cathleen began to stroke my cock into
an erect state and then proceeded to suck on it. She loved to stick her tongue
in the little hole and nibble on my cock head. This always made her hot and
then she needed my cock in her pussy. She straddled me and aimed my cock in
her hole and rode me until she achieved another orgasm.  
  
It was time for me to fuck her in the ass so I had her kneel on all fours with
her gorgeous ass in the air. She always put her head on the mattress and
turned to the side so that she could watch. This time she had the added
benefit of mirrors on the wall and ceiling and so could clearly see the
penetration. I broke out the lube and put an ample amount in her asshole. I
fingered her ass and pussy at the same time.  
  
"I love the feel of your fingers in my ass and pussy together," Cathleen
exclaimed!  
  
If there was one thing I liked besides fucking a beautiful ass it is preparing
an asshole for a good reaming. After several minutes of finger fucking her
pussy and asshole I couldn't wait any longer and I had to get my cock in her
beautiful ass. I removed my fingers and lined up the head of my cock at her
moist puckered ring and pressed forward slowly. My cock head strained to pop
through and she let out a little groan as the pressure from my iron hard dick
forced her little ring to open like a flower and suddenly my large mushroom
head slipped past the ring and into her ass. Cathleen let out a groan as her
rear passage was stretched to accommodate my ample girth.  
  
"Oh you are going to make me like this more than the regular way," she gasped
and shivered as I filled her fully and withdrew my penis slightly.  
  
I felt her ass tighten around me and I continued to slowly stroke in and out
of her tight ass until all eight inches were tightly packed up her ass.
Cathleen really began to moan and her whole body shook in anticipation of what
she knew was coming. I began to slowly fuck her but soon picked up the pace as
I penetrated her with long hard strokes that used the entire length of my
thick cock. Cathleen was going wild as she loved the feel of my cock as it
pulled out and then came crashing back in as my big heavy balls bounced off
her clit. Cathleen was thrashing around uncontrollably, gasping and moaning
with pleasure. When I reached underneath her to stroke her clit she exploded
with her third orgasm of the night.  
  
I continued to hammer her ass with long strokes then suddenly I felt that
familiar tension in my balls and I knew I was close. I began to piston my
raging cock harder into her searing ass in search for my release, which also
increased the intensity of her orgasm. She was yelling and moaning, clawing
and scratching at the cover of the waterbed begging me to cum.  
  
"Give it to me, give it to me, give me your cum, cum in my ass," she begged.  
  
I felt powerful and dominant with my impressive dick stuffed up the beautiful
ass of a woman who could not get enough of me. Cathleen lay submissively
before me on all fours as I towered above her like some untamed animal with a
strong sexual hold on her. I took firm hold of her hips and slammed once more
full force into Cathleen's ass. I did that three or four more times and then I
let out a loud groan as I emptied my seed deep into her bowels. I couldn't
believe how much cum I produced as my dick continued to hammer into her ass.  

When I was finished I pulled out of her ass as Cathleen collapsed on the bed
utterly spent. I slumped down next to her quivering body. I looked over at
Cathleen and I noticed my seed oozing from her asshole. It resembled a natural
spring as the semen just seemed to bubble up as she tried to relax her anal
muscles.  
  
Cathleen and I got up, showered and returned to the Jacuzzi where we soaked
our aching muscles. After the Jacuzzi I offered her a massage which she gladly
accepted. I had her lay face down and worked her back, legs and buttocks. Not
so surprisingly I got an erection as I massaged and fingered her ass again.
Very surprisingly I came a second time that night when I fucked her ass again.
After the ass fuck I rolled Cathleen over on her back and continued the
massage this time working her tits, abs, legs and pubes. I finished her off
with another thorough pussy eating which had her screaming my name and humping
my face with her volcanic orgasm. After that we were really spent and had just
enough energy to shower, dress and drive home.  
  
ANOTHER WOMAN JOINS IN  
  
Cathleen approached me one day and asked if I would like to add another woman
to one of our sessions. I laughed and told her it sounded like fun but that
she was plenty for me by herself. I asked her what she had in mind. Cathleen
told me that the aerobic instructor Janey seemed more than just casually
interested in her.  
  
"I have never been with another woman and I thought it may be fun to try it,"
Cathleen said with her sexy demur.  
  
"Well I am all for it if you want to," I replied.  
  
"I was thinking about asking her to join us for a drink after aerobics
Thursday night and then we could talk her into joining us at the Chateau,"
Cathleen suggested.  
  
"Sure why not, let's see what happens," I agreed.  
  
Janey was in her late twenties, cute and solidly built. She and Cathleen had
hit it off in aerobics. Cathleen knew that Janey dated so we guessed that she
was bi-sexual. When I met Janey I was impressed with her physical presence.
Janey was not fat but she was solid and although she didn't have Cathleen's
curves she was somewhat appealing. So on Thursday night after aerobics
Cathleen and I met Janey for drinks at our local watering hole.  
  
Our conversation at the bar started out with small talk but it was clear that
Janey was flirting with both of us. Cathleen eventually steered the
conversation toward sex and we learned that Janey was not as experienced as
one may have thought from looking at her. She had had plenty of dates and one
longer term relationship but her sexual experience seemed to be only vaginal
sex in the missionary position. Janey was surprised to hear that Cathleen and
I were so sexually active and it seemed to turn her on. Cathleen convinced her
to join us at the Chateau as she told Janey that she could always leave if she
was uncomfortable. Janey nervously accepted and agreed to meet us at the
Chateau.  
  
Once in our room at the Chateau I poured wine for each of us and Cathleen took
Janey by the hand and said, "Let's you and I get better acquainted."  
  
Cathleen led Janey to the center of the room where she embraced her and kissed
her and Janey kissed her back. Cathleen began to undress Janey. She unbuttoned
Janey's suit jacket and removed it, then she unbuttoned Janey's blouse and
removed it as well. Cathleen was pleased to see that Janey did not wear a bra
and she gently massaged the girl's tits. Cathleen rolled Janey's nipples in
between her fingers and then dipped her head down to take them one at a time
in her mouth and roll them in her teeth and Janey sighed with pleasure. One
would never know that this was Cathleen's first time with another woman.  
  
Cathleen's mouth left Janey's tits and then kissed her once again plunging her
tongue deep into Janey's throat taking her breath away. As she kissed Janey,
Cathleen continued to caress Janey's tits with her hands. Cathleen trailed her
kisses down Janey's face and throat back to her breasts. Cathleen lingered at
Janey's breasts momentarily and then descended across her abs to her waist.
Cathleen unhooked Janey's skirt and slowly lowered it to the floor. Cathleen
lifted Janey's legs one at a time clear of her skirt and then ran her hands up
her legs to the waistband of Janey's thong panty.  
  
She caressed Janey's shapely buttocks before she pulled her thong down her
legs. Cathleen teasingly slowly lowered Janey's thong down her legs and then
removed it as she had her skirt. Janey was trembling with desire but Cathleen
made Janey wait as Cathleen took her time with her. Janey looked at me with
uncertainty as she was unsure of her situation and when I may enter the
seduction. Cathleen then rolled Janey's thigh nylons down and off her legs.
Janey was dripping with desire and her pussy was oozing her excitement.
Cathleen took one swipe of Janey's pussy with her tongue and then stood up.  
  
"Now you may undress me," Cathleen said as if giving Janey permission.  
  
With her hands shaking due to her uncontrollable lust, Janey began to undress
Cathleen. Cathleen was wearing a black dress and it fell to the floor as Janey
unhooked and unzipped it. Cathleen stood there in her bra, panty and nylons
and she was a specimen of beauty. Janey unfastened Cathleen's bra and her pert
breasts stood out. Janey took Cathleen's tits in her hands and massaged them
emitting a pleasurable moan from Cathleen. Janey salivated over Cathleen's
firm luscious tits with their dark engorged nipples. She sucked on Cathleen's
nipples as she molded the pert firm globes in her hands. Janey fell in love
with Cathleen's small firm tits.  
  
Cathleen reminded Janey that there was more and Janey next removed the nylons.
They were thigh highs with elastic tops just as Janey had worn. Janey remained
on her knees after removing Cathleen's nylons and stared directly at her panty
covered pussy. Janey then grabbed the panty at the waistband and slowly
unveiled Cathleen's treasure. Janey grasped Cathleen's firm fleshy ass and
pulled Cathleen toward her face. Janey then buried her face in Cathleen's bush
and licked frantically at her pussy. Cathleen moaned with pleasure but then
she reached down and pulled Janey to her feet.  
  
"Let's pleasure each other," Cathleen said as she led Janey to the large bed.  
  
Both beautiful women lay down on their sides in a 69 position and began to eat
each other's delicious pussy. They tongued each other and sought out each
other's clit. Janey was pleased that Cathleen had a large clit and it was like
sucking a tiny dick. Cathleen went wild when Janey sucked and nibbled on her
clit and she strove to return the favor to Janey. The two women brought
themselves off rather quickly but continued to eat each other as the juices
flowed into their mouths. Janey and Cathleen felt the presence of my body on
the bed as and I got behind Cathleen.  
  
"Don't worry, she loves it in the ass," I told Janey.  
  
I eased my lubricated cock into Cathleen's asshole and I knew that Janey could
witness the anal penetration. Janey and Cathleen continued to eat each other's
pussy with a fury as my dick fucked Cathleen's ass and I raced toward my
orgasm. I fired a huge amount of cum in Cathleen's asshole just as she
orgasmed and bathed Janey's face with female love juice. Janey was not far
behind and then she squirted her nectar all over Cathleen's face.  
  
Cathleen got up and retrieved her surprise for the evening a double headed
dildo that was easily 16" long and 5" around. The dildo had two realistic
looking cocks at either end with a large set of fake balls in the middle.
Cathleen turned Janey toward her and inserted one end of the cock in her pussy
and the other end in her own pussy. The two women began to slowly fuck each
other with the large fake phallus as they rubbed each other's tits. The fake
cock filled both women's pussies snugly and stayed in constant contact with
their clits. They fucked each other this way until they both orgasmed again,
shaking and holding tight to each other as tremors moved their bodies.  
  
I got to fuck Janey's pussy but she didn't want me to cum in her so Cathleen
pulled my cock from her just as I was ready to cum and popped my dick in her
mouth. Cathleen drank down all my seed as she had done so many times, then she
caught Janey off guard by kissing her on the mouth and allowing Janey to taste
my sperm on her lips. Later I fucked Cathleen doggy style as she ate Janey's
pussy and then Janey ate Cathleen as I fucked Janey doggy style.  
  
In the coming months the three of us had sex together often. Cathleen taught
Janey how to suck cock but Janey would never let me cum in her mouth. Janey
and Cathleen would pass my cock back and forth and when it was time to cum
Cathleen took me in her mouth to receive my seed. Janey had no interest in
anal sex apparently some guy forced himself on her in the past and caused her
severe pain. I never pushed the issue with her as much as I would have liked
to pop her ass and besides Cathleen was a great ass fuck. Janey later found a
steady boyfriend and our affair were her stopped.  
  
SEX ANYWHERE AND ANYTIME  
  
Over the next several years up to the end of 1989 Cathleen and I continued our
affair. We continued to have sex in the office, car and the romantic interlude
hotel. We played games with each other taking turns being a slave and having
to do what the other person demanded. There were times after aerobics that
Cathleen would come into my office and I would pull her leotards down just
enough to bare her ass. I would fondle her ass and finger-fuck her pussy.  
  
There was no shortage to our imagination and willingness to have sex in public
as well as private places. Cathleen, I was to learn, was somewhat of an
exhibitionist. She loved to be totally naked in private places and was really
turned on by the chances we took in public places. She loved it when I ran my
hands under her skirt and inside her panties. She loved it when I pulled her
leotards down to her knees and played with her buns and pubes. Cathleen could
never seem to get enough of my cock. She loved to fuck me, suck me and have me
fuck her ass.  
  
I was always concerned about the possibility of someone walking in on us even
though the office door was locked. Staff from facilities and security had
master keys and they could easily enter my office. It was one of the reasons
we were never totally naked in the office. If someone did try to enter the
office we could be dressed before the door opened. However, Cathleen wanted to
expand our office sex beyond oral sex and fingering. So I picked up a door
brace at the hardware store and we used that to keep any intruders out.  
  
Cathleen would enter my office close and lock the door and then put the door
brace in place. Then she would stand next to me and hold her skirt up while I
pulled her panties down and off her body. She then moved to one of the chairs
in my office and sat in it with her legs splayed and her pussy on display. I
moved over to her, dropped my pants and undershorts and put my cock in her
pussy. I fucked Cathleen until she came several times. Sometimes I would cum
in her pussy and other times I would fuck her ass. Cathleen would kneel on the
chair with her skirt thrown up over her back and her beautiful ass pointed at
me. I took the lotion from my desk and lubed her asshole and my cock and then
fucked her until I filled her ass with my seed. I kept towels in the office
and we would both clean ourselves up and then get dressed.  
  
Cathleen loved our games and she loved to act as if it were the first time
each time. She would stand by my desk acting innocent and awaiting my move. I
slid my hand up her leg and I felt her tremble slightly as we had played this
game before and she knew where it was going. I let my hand ride about and down
her stocking covered leg for a few minutes. Then I let my hand wander above
her knee and past the top of her elastic top hose. Cathleen shivered as my
hand touched the bare skin of her thigh. I caressed both of her thighs and I
could tell that she was getting hot. The back of my hand brushed against her
panty covered pussy and I could feel that the panties were soaked with her
excitement. Cathleen moved her legs wider apart causing the skirt to tighten
around her shapely ass. I rubbed her inner thighs between her legs and flicked
my fingers over the material covering her vulva. Cathleen jumped involuntarily
when she felt my hand on her pussy.  
  
"Your panties are very wet Cathleen. Would you like me to take your panties
off you?" I teased her.  
  
Cathleen nodded and gasped, "Yes, please take my panties off."  
  
I eased her panties down over her buttocks, past her thighs and then let them
slide to her ankles. Cathleen stepped out of them and I put them on my desk. I
returned to fondling her ass and thighs and I soon had her squirming with
desire. Cathleen moved her body as if she were trying to get my hand near her
pussy so I slid it between her legs and stroked the outer lips of her labia.
Cathleen squirmed under the touch an emitted a soft groan. I started to push
Cathleen's skirt up but she stopped me and then she took it off. It was a wrap
around skirt and she had it off in an instant. She looked so sexy standing
there leaning forward slightly on my desk. Her cute ass was framed by her
thigh high hose and her short blouse ending at her waist line. She actually
looked hotter by keeping the blouse on.  
  
I ran my hands all over Cathleen's ass, thighs and pubes feeling her wet
pussy. I slipped my finger into her vagina and then added a second one. I took
some lotion from my desk and I pushed a finger between the cheeks of her ass
and massaged into her nether hole. Then I fingered Cathleen's ass and pussy at
the same time. She was going wild with the double penetration and cried out to
me.  
  
"That's it finger me, play with me. Make me cum, please make me cum," Cathleen
pleaded in a deep whisper.  
  
I continued to work her ass and pussy and within minutes she had her first
orgasm. Cathleen held onto the desk with both hands as her body jerked and
spasmed with her climax. I worked my fingers in and out of her holes as she
clenched and relaxed her vaginal and anal muscles tightening herself on them.
I pulled my fingers from her holes and I stood up behind her. I dropped my
pants and boxers to my ankles and brought my rock hard cock to her buttocks. I
let it rest against the hot flesh of her ass and I leaned over and whispered
in her ear.  
  
"Where do you want it first today? Do you want it in your ass or do you want
me to fuck your pussy first?" I teased her and then licked her ear.  
  
"Fuck my pussy first and then my ass. I want you to cum in my ass," Cathleen
murmured.  
  
I then eased my cock into her pussy and fucked her from behind until Cathleen
orgasmed once again. Then I moved my cock to her ass and fucked her for a
short time before I unloaded my semen in her anal canal. Cathleen looked so
hot leaning over the desk with my cock sliding in and out of her asshole that
I just couldn't prolong my ejaculation any longer. I leaned over her and she
milked my cock dry until it softened and popped out of her ass.  
  
Our sexual encounters in the office usually ended up the same way, with me
cumming in Cathleen's ass but only after she had cum herself two or three
times. Cathleen would surprise me from time to time. One day she leaned over
the desk and as I ran my hands up her legs I discovered that she had already
removed her panties. Another time she just walked in and immediately took off
her skirt and panties. Without her skirt and panties she looked very hot in
just her hose and blouse. Once she brought a dildo with her and put it in her
pussy so that when I took off her panties I would find it. Cathleen liked
being fucked in the ass and having her pussy filled with the fake cock.  
  
Some days when she needed a ride to work I would pick Cathleen up at her
house. On the way to the office Cathleen would remove her panties and I would
play with her pussy. Once we reached the office we were both very hot and we
went inside and fucked like rabbits. Cathleen had really adapted to anal sex
and I came in her ass at least once every time we were together. She loved the
anal toys as well especially the anal beads.  
  
One time at the La Chateau, Cathleen brought a unique dildo with her that had
two cock heads on a handle. It looked like a big letter Y. Cathleen would put
one cock in her pussy and the other in her ass for double penetration.
Sometimes we would be in a 69 position and she would suck my cock as I double
fucked her with the dildo. Cathleen went wild and juiced all over the fake
cock as I filled her mouth with cum. There seemed to be no end to her
creativity and willingness to try new things. However she never showed
interest in adding another man to our encounters.  
  
Over the five years we had sex frequently at least once and sometimes twice a
week. I was recruited by a firm in California and accepted the position.
Cathleen elected to stay in Chicago although I offered her a position as my
assistant with the California firm. I missed Cathleen but at the same time I
cleaned up my act and eliminated any extra-marital activities. I still think
back to those years with Cathleen who made sex in the office the best.




End file.

