


Chicago - My Kind of Town

by walterio



Category: Anal
Published: 2010-10-29
Updated: 2010-10-29
Packaged: 2017-05-06 13:06:04
Chapters: 1
Publisher: literotica.com
Story URL: https://www.literotica.com/s/chicago-my-kind-of-town
Author URL:
https://www.literotica.com/stories/memberpage.php?uid=429765&page=submissions
Summary: A memorable affair in Chicago before heading to California.
Erotica Tags: Big Cock, Chicago, Foreplay, Great Asses, Massages, Office, Oral
Sex, Public Sex, Seduction, Vaginal Sex
Average Rating: 4.54






        Chicago - My Kind of Town


PRELUDE  
  
I rolled over in the morning and bumped into another naked body in the same
bed. I slowly recalled the marathon of sex the night before and then I
realized that I had a raging piss hard-on. A soft hand embraced my stiff
member and held it gently and I remembered that Catherine and I were in a
hotel room together.  
  
"Good morning sleepy head. Did I wear you out last night?" she whispered in my
ear as she fondled my rigid tool.  
  
I was still groggy as I had slept soundly and had some wild dreams. I yawned,
stretched and made an attempt to get out of bed. "I have to pee," I told her.  
  
"Not until I get to ride you. I'm going to take advantage of your condition
this morning," Catherine remarked as she positioned herself to straddle my
morning erection.  
  
It was not the first time that Catherine and I had sex in a hotel room but it
was the first time we ever stayed the night in a hotel. We had been having an
affair for over two years and most of our sexual activity was conducted in my
office although we did go to a romantic interlude motel at least once a week.
Even though we were both divorced and single we did not live together. You
see, Catherine was my secretary and administrative assistant. Our company had
a strict policy about nepotism and inter-office romances.  
  
I had sent Catherine to an Administrative Assistant / Secretarial seminar in
Amelia Island, Florida. Then I took vacation days and stayed in the same
hotel. We would be together for four days and three nights and I had just
survived the first night. Now I was trying to survive the morning as she rode
my piss hard-on. She was determined to orgasm as many times as she could that
morning until she could not cum anymore.  
  
"Don't pee in me," she teased as she rode my shaft like a woman possessed.  
  
"Don't worry, that is not a possibility," I answered remembering how difficult
it was to pee with an erection.  
  
A few times in the morning I had to pee so bad that I tried but it wasn't
until my penis softened to a semi-erect state that I could urinate. Even then
it was difficult to control and I ended up missing the toilet with the first
stream. I knew that my cock would stay hard as long as Catherine rode me and
that I would not accidentally pee in her pussy. She rode me hard and at times
I thought that my bladder would burst but it held out. Finally after a number
of mild orgasms she climaxed and collapsed on top of me. I wrapped my arms
around her body and held her tight as she bucked and screamed.  
  
Catherine was always vocal when she orgasmed and often she would cum so hard
that it was scary. I had gotten used to her orgasmic behavior and I loved to
make her cum as much as I could. After a few minutes she rolled off of me and
flopped over on her back.  
  
"That was marvelous. We have to have more morning sex from now on," she
sighed.  
  
I rolled out of bed and made my way to the bathroom with my erect cock
pointing the way. I stood over the toilet and tried to aim so that when I
finally urinated that I would not miss the toilet. It took several painful
minutes for my erection to soften enough so that I could pee and then finally
success. It seemed like I peed for at least two minutes and the pressure was
extreme. Then I washed my hands and my penis before returning to the bedroom.
Catherine was waiting for me as she knew that I wanted to cum before she left
the room for her seminar.  
  
If we had more time that morning I would have fucked in her beautiful ass
again. I loved anal sex and Catherine had one of the nicest asses that I ever
fucked. However she need to shower, dress and get going so I settled, if you
could call it that, for one of her signature blow jobs. Catherine was an
accomplished cock sucker and I had been the recipient of countless blow jobs
mostly in my office. However now were both naked in bed and I reclined on my
back as she masterfully sucked my cock.  
  
I gently caressed her long brown hair as her head bobbed up and down on my 8"
dick. She would pause every so often and lower her mouth as far down as she
could taking in most of my cock. Catherine loved to do the deep throat thing
always testing her gag line. It wasn't long before her expert cock sucking,
fondling my testicles and tickling my perineum that she had me spurting in her
mouth. Catherine loved to swallow cum and she drank down every drop as ropes
shot into her mouth. She kept me in her mouth until she had drained my shaft
dry.  
  
Catherine then became all business like and got ready for the seminar. She
showered and dressed and then headed down to breakfast. "I'll see you around
4:00 PM," she said as she headed out of the room.  
  
"I'll be by the pool," I told her.  
  
"Behave," she teased.  
  
"You enough woman for me," I called back to her as she shut the hotel room
door.  
  
I decided to go to the fitness center and work out before breakfast. After my
workout I would shower, dress and go to breakfast. Then I would head to the
pool and read the book that I had brought along. It was a book that I had been
meaning to read and this would be a good week to do that. I knew that evening
would be a repeat of the night before. First we would dine at a good
restaurant and then we would have incredible sex back in the room.  
  
That day as I sat by the pool I had a difficult time concentrating on the book
that I was reading. First of all there were a number of hot looking girls in
skimpy bikinis around the pool who got my attention. However the main reason
was that I was thinking about Catherine and our two year affair. My mind
drifted back to the start of our affair about two years ago.  
  
HOW IT ALL STARTED  
  
Two years earlier I, Cliff Watkins, was hired as a Senior VP to head up the IT
division for a national firm headquartered in Chicago. I inherited the entire
staff including the secretarial staff. Over the next six months I would make
my assessments of the talent and capabilities of the staff before making any
changes in personnel and restructuring the organization. During those six
months I learned that my secretary Catherine was very capable and very loyal.
She demonstrated that she could handle confidential and sensitive information.
She was definitely a keeper.  
  
During that time I didn't look at Catherine as a sex partner as she was not
that pretty. Although not unpleasing to the eye she just wasn't the type that
I usually went after. Still she was very fit and presented herself very well.
She always dressed tastefully and professionally and conducted herself
accordingly. Catherine participated in aerobics three days a week; Tuesday and
Thursday evenings and Saturday mornings. Since we were so busy the first six
months she would often return to the office after her aerobic class on Tuesday
and Thursday to assist me. She would remain in her aerobic outfit and that was
when I started paying attention to her very shapely ass.  
  
It had been difficult to assess Catherine's figure when she was wearing her
business clothes as she always wore long full dresses and skirts. However the
first time I saw her in her aerobic outfit and the way the spandex hugged her
curves, I appreciated her figure. Catherine was 5'6" tall with long brown
hair. She weighed about 125 pounds and she was very solid. Her legs were
muscular but shapely and her ass was to die for. Catherine was small breasted
but I was never turned on by big tits so it didn't matter. At 28 years of age
she looked good. I was 6'2" tall and weighed a fit 190 pounds. I was in
excellent shape from my years of sports activities and frequent visits to the
gym. At 32 years of age I was proud of my physique and fitness.  
  
The day had come when it was time for me to present the Information Technology
(IT) Strategic Plan to the senior management team along with my
recommendations for organization change. Only Catherine and I knew what the
organization changes were being recommended and how it would affect the staff.
The presentation went extremely well and I received approval for the five year
plan and budget. I also received permission to make the organization changes
necessary to implement the five year strategic plan. That afternoon I held a
town hall meeting with the IT staff and revealed the organization changes. I
informed the staff that Catherine would be setting up a one on one appointment
with me for many of them. That Wednesday evening I was still in the office
when Catherine stopped in and asked if I was up for a drink.  
  
"You look like you could use a drink," she observed.  
  
"You're right! Do you know of a good spot I don't want to go to any of the
local watering holes," I replied.  
  
"There is a great bar near where I live that no one from the office goes to.
They have great burgers too," she suggested.  
  
"Sounds perfect, I am hungry too," I agreed.  
  
"Why don't you follow me there but here's the address in case we get
separated," Catherine offered as she wrote down the address.  
  
We then left the office together and I followed her to the bar. She was right.
It was a cozy place with great burgers. We discussed the day over a few beers
and a burger and Catherine shared her feelings about the new organization
structure. She alerted me to a few staff members who would take exception to
the changes but I was already prepared for them. After we finished our beers
we left the bar and walked out into the parking lot. I walked Catherine over
to her car to be sure she was safe even thought it wasn't necessary.  
  
When we got to her car I thanked her for all her hard work. "Catherine, you
have been a gem these past six months and I thank you for all your hard work
and your loyalty."  
  
Catherine looked up at me and smiled. Her eyes twinkled in the street light
and I had the urge to kiss her. I took her in my arms and kissed her tenderly.
She kissed me back but it didn't last long.  
  
"Sit with me in my car for a few minutes," she whispered.  
  
I got into the passenger seat as Catherine got into the driver's seat. We did
not kiss again as I expected and Catherine shocked me with her aggressiveness.
She leaned across the seat and unbuckled my belt and unfastened my suit pants.
Then she pulled my pants and boxer shorts down to my knees. I instinctively
lifted my hips up to facilitate her. My cock was erect within seconds.  
  
"I have wanted to do this for a long time," she whispered right before she
engulfed my cock in her mouth.  
  
Her head bobbed up and down a few times on my 8" porker and then she lifted
her head to speak again. "You have a nice cock," she said and then returned to
sucking me.  
  
Catherine was very accomplished in oral sex and I was as hard as a rock. Then
she stopped sucking and I watched as she reached under her full length skirt
and removed her pantyhose and panties.  
  
"I am really hot. I need to sit on your cock. I want to fuck you," she
announced surprising me with her language.  
  
I had heard women use the words cock and fuck before it was just that I had
never heard it from Catherine. Then with catlike movements and agility, she
straddled my body and guided my cock into her pussy. She groaned as my shaft
filled her vaginal cavity and I felt the wet silkiness of her cunt. Catherine
rode me hard and fast and it was obvious that she was only thinking about her
own orgasm.  
  
"Oh. Oh, this is going to be a quick one," she gasped.  
  
I looked at the car windows to see if anyone was spying on us but the windows
were steam covered and it was impossible to see in or out. We did make quite a
sight though as we fucked in her car. I was still in my suit jacket, shirt and
tie with my suit pants and boxer shorts down below my knees. Catherine's dress
was gathered around her waist and I held on to her shapely ass while she did
all the work.  
  
"I'm going to cum. Hold me!" she called out excitedly as her hips flailed on
top of me.  
  
I held her by her curvy ass and then my arms moved up and wrapped around her
upper body as she screamed into my shoulder. Her screams were muffled in my
shoulder as her body shook and shivered with the intensity of her orgasm.
Catherine eventually stopped moving and relaxed in my arms briefly before
easing her body off of mine. She sensed that I had not cum and in her desire
to pleasure me she lowered her mouth back onto my cock. It was obvious that
she did not mind the taste of herself as she gave me an incredible blow job.  
  
Catherine fondled my testicles and ran her finger along my perineum as she
swirled her tongue around my shaft. I felt my discharge building within me and
I warned her that I was about to cum. Catherine never removed her mouth from
my cock and she received a mighty discharge. Ropes of semen shot into her
mouth splashing off the back of her throat but she never missed a beat.
Catherine stayed glued to my cock until she had sucked every last drop of
semen from my shaft. Tingles ran through my body and I felt my toes curl up
inside my shoes. It was the best blow job ever.  
  
We relaxed for a few minutes and then got dressed the best we could. At least
I did. Catherine opted to stuff her hose and panties in her purse. Then we
opened the car windows and let the air in. I waited until the windows were
clear and it was safe for Catherine to drive home. We said goodnight but
didn't kiss. I walked back to my car and then watched as Catherine drove off.
I then drove home all the while wondering where this would go. I had clearly
crossed the line by having sex with a company employee and my secretary at
that.  
  
SEX IN THE OFFICE  
  
On Thursday, Catherine arrived at the office on time and she went about her
duties as normal. There was no mention of the car sex that we had the night
before. She did not bring it up so I decided not to mention it either. We both
went about the day in a business like manner. That evening after her aerobic
class Catherine returned to the office wearing her snug spandex outfit. I
observed her move around tidying up her desk and doing some filing before she
left for home.  
  
As I watched her I focused on her round curvy ass and I got a boner just from
looking at her. It was all I could do to keep my hands off of her. I wanted to
pull her into my office and pull her pants down and bare her ass. However I
knew better and I restrained myself although it took all of my will power. If
we hadn't had sex the night before I would have never thought of doing that.  
  
"Good night, see you tomorrow," Catherine said as she poked her head in my
office.  
  
"Oh, good night, don't forget that we are doing your performance review
tomorrow," I reminded her.  
  
"I won't. I'm looking forward to it," she replied and then waved goodbye.  
  
I returned to my work of finishing up Catherine's performance review. I gave
her an outstanding review as she had been invaluable during my first six
months on the job. I recommended that her position be raised one level and
that she be given the title of Administrative Assistant. That would be
consistent with the other Executive's former secretaries who all now held the
title of Administrative Assistant. I was sure that Catherine would be pleased
with her review and promotion.  
  
The next day I conducted Catherine's review at 10:00 AM thinking that we could
go to lunch afterward and celebrate her good news. Promptly at 10:00 AM
Catherine was seated adjacent to me at the small conference table in my
office. I had locked the office door so that we would not be disturbed.  
  
I opened the booklet containing Catherine's performance review and my
evaluation of her work. As I read through each category and began to explain
my rationale for the rating, Catherine just stared at me the entire time. She
seemed disinterested in what I had to say. About half way through the review
she reached over and took my hand in hers. I stopped talking and looked into
her dreamy eyes and sensed that she wanted something to happen.  
  
"I know that you gave me an outstanding review and I appreciate that and the
promotion. I want to show you how much I appreciate it," she whispered and
added, "Stand up in front of me."  
  
I stood up and remained still as Catherine unbuckled my belt and unfastened my
suit pants. She took her time and then lowered my pants down past my knees. I
could feel my cock rising to the occasion and my boxer shorts tented in
evidence of my excitement. Catherine smiled as she reached for my cock and
then she fondled it through the fabric of my boxers. I groaned as she gently
squeezed my shaft. Then she slowly pulled my boxers down my legs allowing my
stiff cock to get caught in the waist band. She continued pulling my shorts
down until my cock cleared the waistband and bobbed in front of her face.  
  
Catherine lowered my pants and shorts all the way to my ankles and then she
pushed my dress shirt and tie up out of the way. I rolled up my shirt and
through my tie over my shoulder and watched as she lowered her mouth to my
cock. Catherine looked up at me as she moved her head up and down on my cock
and the expression on her face was one of pure ecstasy. She gently held my
balls in one hand as she worked her magic on my cock and I did not last long
at all.  
  
"Catherine, I'm going to cum," I whispered.  
  
Catherine, however, as she had done Wednesday night in her car stayed glued to
my cock. I exploded in her mouth with one of my most massive ejaculations
ever. It seemed like I kept cumming for minutes although I knew it was over in
a matter of seconds. Catherine sucked me dry again as she had done the first
time. She kept my cock in her mouth for a seemingly long time after I came and
she nibbled on it teasing me and driving me wild. I had tingles running
through my body and I had to push her head away as I began to feel weak in my
legs.  
  
I steadied myself by holding onto the table and then I began to redress.
Catherine smiled at me again and licked her lips in a very sexy way. I had
pulled my shorts and pants back up and then I tucked my shirt back in and
buckled my belt. I sat back down and smiled at Catherine.  
  
"There isn't any provision for me to evaluate that skill on your appraisal
form," I said jokingly and then added, "But if there was you would receive the
highest grade possible."  
  
"Forgive me but that made me very hot. I need to cum," she whispered as she
lifted her skirt and pulled her pantyhose and panties down just below her
pussy.  
  
I looked at her neatly trimmed pussy for the first time and liked what I saw.
Catherine had a beautiful pussy with a little tuft of brown hair just above
it. I surprised her when I moved to my knees in front of her. Then I pulled
her hose and panties down to her ankles. I did not remove them as I wanted her
to be able to pull them back up if we were interrupted. I lifted her legs up
and ducked my head under the hose and panties gathered around her ankles. Then
I leaned in and placed my mouth on her pussy.  
  
Catherine groaned when my mouth covered her cunt and then she emitted a squeal
when I located her clit. Within minutes Catherine was cumming and juicing my
mouth. She covered her mouth with her arm and moaned into the elbow joint
stifling her outcry. I continued to lick her pussy as she thrashed around on
the chair until she went limp. Then I kissed the inside of her thighs and
eventually removed my mouth. I lifted her legs back over my head and then sat
back in my chair. Catherine was in a euphoric state and she glowed in her
pleasure.  
  
Catherine then pulled her panties and hose back on and smoothed her dress as
she stood up. She kissed me on the cheek and said softly, "That was an
incredible performance review."  
  
"It certainly was," I replied.  
  
Catherine then left my office. It was the first of many office encounters. In
the weeks to come, we had sex in my office and at times in the car. Catherine
would give me marvelous blow jobs in my office. She loved to suck my cock and
swallow my load. Sometimes we would play little games of seduction as if we
were getting it on for the first time. Catherine would come into my office,
close and lock the door and come around to my desk as if to show me something
important. As she showed me some document I would let my hand move up her legs
over her pantyhose up to her ass. I would fondle her ass for awhile and then
lower her hose and panties to her knees. I played with her pussy as I fondled
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 would
repeat 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
would have me stand up and she knelt in front of me. Catherine 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. Catherine
would then suck my cock until I came in her mouth.  
  
We also revisited the bar near her place and after a burger and a few beers it
was sex in her car again. Sometimes we fucked and sometimes she just sucked my
cock while she fingered her pussy. She would unbuckle my belt, unbutton my
trousers and pulled them along with my boxers down to my ankles. As Catherine
pulled my boxers down over my balls she would lick and suck them before
kissing her way up my shaft. Looking up into my eyes, she would slide her lips
over my bulging head with her hand still wrapped around my shaft. Her tongue
would swirl under the ridge of my crown as she sucked me deeper into her
mouth. She would test her gag line and take my cock down her throat.  
  
She would pull 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 would have me on the verge of a huge orgasm. Catherine would often
slip her hand into her spandex and finger her dripping pussy. The smell of sex
would be rampant in her car.  
  
When I felt my cock swell and I told her that she was about to receive my
load. Muffled moans would escape from her throat as she eagerly sucked my dick
awaiting my release. She would move her lips up and down over my shaft in
rhythm with my thrusting motions. She would be drooling like crazy and I could
feel the wetness running down my pecker onto my balls.  
  
My breathing would become more erratic as I was about to lose control.
Catherine would look up at me with those big eyes and nodded her head, letting
me know she wanted to taste me and then she would cover my cock with her mouth
just as I lost it. I always let out a soft grunt as I pumped stream after
stream of hot cream into her mouth. She would move her hand under my scrotum
to squeeze out the last few drops and then Catherine would have her orgasm.
The feel of my throbbing cock in her mouth, the taste of my seed and her hand
in her cunt was just enough to set her off. The pressure in her lower tummy
would gush out through her pussy and soak her fingers.  
  
My cock would fall from her lips and cum would drip from her lips and chin as
her body would jerk and shudder in orgasm. Catherine always 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 would take Catherine's hand and licked her fingers
clean. I would then pull my shorts and trousers back up and dress the best I
could in the confines of her car.  
  
One night when we were having a burger we discussed getting together in bed
and being completely naked when we had sex. Catherine didn't know it but I was
very hot for her ass and I wanted a shot at it. She had a roommate so we
couldn't go to her place. I lived in an area where other corporate executives
lived and I couldn't risk Catherine being seen at my place. We discussed
hotels and motels but I was leery of them as many of our vendors stayed at the
ones near the office. That's when Catherine suggested a romantic interlude
motel called La Chateau.  
  
THE ROMANTIC INTERLUDE  
  
On our first trip to La Chateau Catherine arrived before me and parked her car
in the private spot adjacent to the room. I had given her my credit card to
pay for the room. I parked in the lot which was secluded from the road and
walked to the room. Catherine was already naked when I arrived. She told me
that this was the only room available as the ones with the Jacuzzi tubs were
all taken.  
  
I looked around as I undressed and spotted the water bed, mirrors on the
ceiling and walls. There was a TV with a porn station and a small mini bar in
the room. Catherine was naked in bed watching me as I undressed and I could
tell that she liked what she saw. I liked what I saw too as it was the first
time that we were completely naked together. I moved to the bed and 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 had 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. Catherine 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.  
  
Catherine 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
Catherine's ass when she spoke.  
  
"Use some cream," she said urgently, "There is some in my purse."  
  
I got off the bed and retrieved the body lotion from her purse. As I did I
realized that Catherine 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. Catherine 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, "Catherine 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 Catherine'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 Catherine 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. Catherine 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. Catherine then lay on her back, splayed
her legs and pulled back the folds of her vagina.  
  
"I need to cum again. 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 Catherine's mound. It felt so smooth and warm and I knew I had achieved the
desired effect from her moan I know that Catherine enjoyed it. I always
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.  
  
Catherine 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. Catherine 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 flicked my tongue over it once and then
used the tip to explore the folds of flesh on either side of it. Catherine 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.  
  
Catherine 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 Catherine 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 Catherine 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.  
  
Once she calmed down, we lay there for awhile making small talk and then
Catherine started stroking my cock. Catherine 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 the biggest I have ever had," she said with a sultry tone.  
  
"Well there are plenty bigger than mine," I assured her.  
  
"If I had a cock I would be playing with it all the time," she giggled.  
  
We continued our conversation as Catherine continued to stroke my cock. I
learned that she had first been ass fucked before she was married and
divorced. Catherine had been 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. I shared with her my
love for anal sex and some of my encounters.  
  
"All this talk and playing with your cock has got me hot again. I need to sit
on your dick," she announced.  
  
Catherine 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. Catherine 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. Catherine 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.  
  
Catherine 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 was still hard so I took her ass again and fucked her until I released
my second load into her rectum. After that we showered dressed and left the
motel.  
  
A week later we revisited La Chateau again and this time Catherine had gotten
a room with the Jacuzzi tub. We entered the room and wasted no time taking off
our clothes as the Jacuzzi filled with hot water and bath gel. Catherine 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.
Catherine then douched 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 Catherine 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 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 Catherine 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 Catherine'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, 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 Catherine 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. It's a great 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. Catherine 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. 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," Catherine
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. Catherine 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.
Catherine 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. Catherine 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. Catherine 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. Catherine 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 Catherine'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 Catherine collapsed on the bed
utterly spent. I slumped down next to her quivering body. I looked over at
Catherine 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.  
  
Catherine 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 Catherine 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.  
  
RISKS AND REWARDS  
  
Catherine 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.
Catherine 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. Catherine came on my fingers again and then she gave me one of her
wonderful blow jobs.  

Afterward Catherine 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 crotchless pantyhose that were very erotic. The
panty hose had a waistband and two side panels attached to the stocking part.
When Catherine wore the new pantyhose her ass and pussy were bare and her ass
looked great framed in the hose. Catherine 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. Catherine 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.  
  
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 Catherine
would come into my office and I would pull her spandex 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. Catherine, 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
spandex down to her knees and played with her buns and pubes. Catherine 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, Catherine 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.  
  
Catherine 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 Catherine until she came several times. Sometimes I would cum
in her pussy and other times I would fuck her ass. Catherine 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 paper towels in
the office and we would both clean ourselves up and then get dressed.  
  
Catherine 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. Catherine 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. Catherine 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. Catherine jumped
involuntarily when she felt my hand on her pussy.  
  
"Your panties are very wet Catherine. Would you like me to take your panties
off you?" I teased her.  
  
Catherine 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. Catherine 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. Catherine 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.
Catherine squirmed under the touch an emitted a soft groan. I started to push
Catherine'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 Catherine'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 Catherine'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,"
Catherine pleaded in a deep whisper.  
  
I continued to work her ass and pussy and within minutes she had her first
orgasm. Catherine 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," Catherine
murmured.  
  
I then eased my cock into her pussy and fucked her from behind until Catherine
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. Catherine 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 Catherine's ass but only after she had cum herself two or three
times. Catherine 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. There seemed to be no end to her creativity and
willingness to try new things. However she never showed interest in adding
another person to our encounters.  
  
THE SEMINAR  
  
The seminar at Amelia Island was the first time that we stayed together for
any longer than one evening and it was great having morning sex with her. It
was Tuesday afternoon and I had three more nights and three more mornings of
hot sex to look forward to with Catherine. I only stayed at the pool until
3:00 PM and then I returned to my room to shower. Catherine called from her
room at 4:30 PM and I told her to come to my room. I was dressed only in my
gym shorts when she arrived.  
  
Catherine smiled and grabbed my cock through my shorts, "Miss me?" she teased.  
  
"You know I did," I replied as I grabbed her ass through her slacks.  
  
"Let's fuck before we go to dinner," she said as she began to disrobe.  
  
In a matter of minutes after she arrived we were both naked in my bed and I
was drilling her pussy. My cock was buried in her and I made sure that in
stayed in contact with her clit. Catherine orgasmed quickly but we kept right
on fucking as I knew that she would cum at least once more. She wrapped her
legs and arms around me and held me tight as she humped my cock. Then she
exploded with another orgasm and it was intense. She cried out and bit softly
into my shoulder to stifle her screams.  
  
"God that was great! Did you cum?" she gasped.  
  
"No, I can wait though. Let's get some dinner and then we can play some more
after we eat," I answered.  
  
"Let's have room service," she suggested.  
  
"Fine with me," I agreed.  
  
We looked over the room service menu and made our selections. Catherine then
got dressed and returned to her to change clothes while I called in our order.
Catherine returned before the food arrived and we sat out on the balcony
overlooking the ocean. Twenty minutes later the food was delivered and we
dined on the balcony. I had ordered two bottles of wine as well knowing that
it would be a long evening.  
  
After we ate we relaxed on the balcony finishing the first bottle of wine.
Catherine started getting frisky and she put her bare foot in my lap. Then she
ran her foot over my stiffening cock as we drank our wine. I felt my cock
harden under her foot but I made no moves to take the action further.  
  
"Take your cock out," she told me.  
  
I fished my cock out of my shorts and it stood up in an erect position.
Catherine had slipped off her other shoe and then she placed her feet around
my cock. She rubbed both feet together up and down my shaft. It was a very
erotic act and I decided to let her have her fun. I felt my balls tighten as
they normally did right before I ejaculated. At that very moment I decided to
cum on her feet.  
  
Catherine had a very wanton look on her face as she jerked me off with her
feet. She was really getting into it and I decided to surprise her with my
ejaculation. Then without warning cum spurted out of my cock shot straight up
and landed on her feet and shins. Catherine giggled when I came but she went
right on stroking my cock with her feet. She continued to rub my shaft with
her feet squeezing cum from it.  
  
Then she spoke softly, "I douched my pussy and my ass for you when I was in my
room."  
  
I knew exactly what she wanted without her asking, "So are you telling me that
your bottom is squeaky clean and that you would like my tongue in there."  
  
"Oh yes," she said excitedly.  
  
We then left the balcony and headed to the bed stripping off our clothes.
Catherine never bothered to wipe the semen from her feet. She was anxious to
be rimmed again and I was ready and willing. Catherine got on the bed on all
fours and wiggled her ass at me in anticipation. I got behind her and ran my
hands all over her lovely buttocks and then pried them apart to expose her
anus. I dipped my tongue between her cheeks and tickled her pink rosebud. I
pushed my tongue into her taut anus and wondered how she could take my cock in
there so easily. I licked Catherine from her anus to her pussy and she went
wild. I kept that up until so orgasmed and collapsed face down on the bed.  
  
Then I began to massage her body as she recovered. I used the body lotion
supplied by the hotel and covered her back and shoulders with it. Then I
worked my way down to her legs and massaged her calves and the back of her
thighs. Next my hands covered her curvy buttocks and I massaged those glorious
globes. I lifted Catherine by her hips and she kept her head on the mattress
and turned her face to the side. She had a dreamy look on her face as I
fondled her buttocks and began to finger her anus.  
  
Satisfied that she was well lubed, I eased my cock into her ass and began to
fuck her slowly. I was determined to take my time and last as long as I could.
I loved watching my cock slide in and out of her shapely ass and I felt as if
I could last for hours. I don't know how long I fucked her in her ass but by
the time I ejaculated my thighs were burning. I fired several streams into her
rectum and as she always did Catherine milked my cock with her sphincter
muscles.  
  
We were both exhausted so we moved into the spoon position and cuddled
together. We fell asleep in that position and didn't move until morning. Then
the insatiable rejuvenated Catherin was ready for morning sex. Once again I
fucked her with my morning piss hard-on until she begged me to stop. Then
after I relieved myself we fucked in the shower and I took her ass again.
After the shower Catherine dressed and returned to her own room to get ready
for the seminar.  
  
It was a marathon as we had sex that evening, Thursday morning and evening and
Friday morning before I left the hotel. I took an earlier flight on Friday
then Catherine as she finished up with the seminar and returned later. That
weekend I chilled out at my condo as I had had more sex in four days than I
would have ever imagined. It had been an unbelievable week.  
  
MOVING ON  
  
Over a five year period the affair continued. We had sex frequently at least
once and sometimes twice a week. I was recruited by a firm in California and
accepted the position. Catherine elected to stay behind even though I offered
her a position as my assistant with the California firm. We had a going away
party on a Friday evening. After the party Catherine ended up back at my condo
with me and for the first time in five years we had sex at my place. Catherine
stayed through Sunday evening and we never left my condo. We had sex for two
straight days and it was as if Catherine wanted me to never forget our final
hours together.  
  
I met some very pretty women in California and had sex with some gorgeous
ladies. As good as it was in California I still remembered the times with
Catherine. The sex with her was great but it was the risk and reward things
that we did that made it exciting. I never had the opportunity for office sex
again but I always recalled how erotic it was. I could still close my eyes and
visualize Catherine standing next to me with my fingers in her pussy and ass.
I would never forget those days.




End file.

