Sex in Public and Risky Places Ch. 06
Author's Note: Over the years I have had sex in interesting places, some public and others risky. As I reflect on those days past I realize just how risky some of those encounters were and how fortunate I was not to be discovered. Others were not risky but wild and exciting as they took place in a third party's residence with the person in the other room. I decided to revisit those encounters and share them with the readers. As I wrote the story it was getting very long so I decided to break it up into chapters as the characters changed from one chapter to the next.
INTRODUCTION
The public places in which I had sex include cars, vans, on the lawn, by a lake, on the beach, in a gondola, in a Jacuzzi and in my office. The places I consider risky include my rented room at college, someone else's apartment, my neighbor's swimming pool, a bar store room and in the bathroom at a party. By risky I mean the chances of being discovered and witnessed by others.
I thought at first that I would write about each experience by location. However sometimes the sex started in one location and moved to another. Therefore I decided to write the stories as they occurred in chronological order beginning in 1960. I skipped over the high school years which included the drive-in movie pussy fingering and hand jobs. The story begins when I was in the Marine Corps and stationed in Naples, Italy. Keep in mind that I had many memorable sexual encounters but I have selected the best that occurred in public and risky places.
In chapter one I wrote about my encounters in Naples, Italy where I had sex with three different women Vittoria, Carla and Emma in the same apartment. Each time there were other people in the next room. I also wrote about my first anal sex on the Isle of Capri. We were on the beach at night when Gianna offered up her ass and it was witnessed by a voyeur. Chapter two was about my public encounters in cars and other people's homes with Erica, Linda and Charlotte. In chapter three my sexual encounters this time were outdoors with Michelle and Peggy
In chapter four encounters were on an indoor tennis court with Shirley, in a storeroom before moving to a hotel with Joanne and at a reservoir with Donna. In chapter five Sue and I will had sex in a hotel Jacuzzi before taking it to her room. On a ski trip I hooked up with a buxom blonde named Sherry and had a mile high experience. The trip also provided one more surprise in the name of Toni.
This chapter is the final chapter of this series. It will be about one person, my administrative assistant of five years. Our public sex took place in cars and the office. We kept getting bolder and bolder with sex in my office.
CATHLEEN 1985 - 1989
DIPPING MY PEN IN THE COMPANY INK
Cathleen was without a doubt the best sex partner that I ever had. She was adventurous and willing to try almost everything. Of all my encounters I remember my time with her more vividly then any other woman. Also our affair lasted for nearly five years and we never tired of each other.
Cathleen was 35 years old. 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, exercised regularly and she was 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 didn't see her figure. She took aerobics two nights a week at a studio that was 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 spandex and it was then that I noticed her firm body and figure.
We first had sex by accident at a company executive retreat. 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. Everyone was in good spirits and enjoyed themselves at the social. 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 cocaine 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.
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 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 wonderful. 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.
"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
SEX IN THE CAR
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 spandex 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 the hotel 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. Cathleen took my balls and 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 slipped her hand into her spandex 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.
We had sex in my car as well. Sometimes 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 but she never released her grip. She swallowed all of my creamy discharge and when I eventually stopped cumming she pulled her head away. She stayed on my cock until she had sucked it dry.
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 replied with a slight laugh.
Cathleen got out of the car and I drove back to my home. Every time I gave her a ride home I could count on a great blow job.
One 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 spandex down to her knees baring her ass and pussy. I played with her ass and fingered her pussy as she sucked on my cock.
As I caressed her lovely ass she said, "You like my ass don't you?"
"I love your ass," I told her.
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.
On several other evenings after her aerobic class we had anal sex in the car. We actually became very proficient in spite of the tight quarters. It was risky to be fucking in the hotel parking lot but we both loved the excitement and I loved being in her ass.
SEX MOVES INTO THE OFFICE
We moved our car sex into a romantic interlude motel. Normally would get together on Tuesday and Thursday evenings after aerobics at the motel. 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. For months the office sex was restricted to oral sex but then we started playing games.
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 ANYWHERE AND ANYTIME
Over the next five 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 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. 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 spandex 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 paper 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 up 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 upper 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 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 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 group sex.
Over the five years we had sex frequently, some weeks it was every day and other weeks it was several times during the business week. We went to the romantic interlude at least once a week and had sex in the car frequently. The car sex in the hotel parking lot was risky and exciting but not as risky as what we did in the office. The thought of my staff being right outside my office, while I was fucking Cathleen in the ass, was absolutely mind blowing. We both got a thrill out of having sex with the possibility of being discovered.