I moved out from under her and allowed her to pull up her pantyhose. She smiled at me and I knew that this would happen on a regular basis from then on. Getting a blow job was easy with my cock sticking out of my fly but eating her pussy while wearing pantyhose was a bit awkward. I made up my mind that I would take her shopping for new hose and panties. Cathleen straightened her clothes and smiled again.
"I hope we can do this more often," she whispered.
"You can count on it," I told her.
That was the start of sex in my office and we had oral sex in the office every Monday, Wednesday and Friday. On Tuesdays and Thursdays we would have sex either in one of our cars or a hotel room. For the next several months it was strictly oral sex in the office as it was the safest and least risky. 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.
Another time when she came into my office and locked the door, I said, "We need to do something about the pantyhose."
"What do you have in mind?" she asked quizzically.
"Let's look through this," I said and I produced a Victoria's Secret catalog.
Cathleen stood by my side as we looked at the catalog on my desk. As she paged through the catalog, I stroked her legs and ass again through the pantyhose. Then I lowered her hose and panties and played with her naked ass and pussy. Cathleen came on my fingers and then she gave me one of her wonderful blow jobs. When we were done she selected a couple of items from 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.
Once we got a little carried away and decided to fuck in my office. Although we barricaded the office door with two chairs it was still too risky. I placed one chair against the door and then a second chair next to the first one. I sat in the second chair with my pants and underwear down to my knees while Cathleen rode my cock. She came twice before getting off of me and sucking my cock until I ejaculated. We loved the sex but I was nervous about someone coming to my office while we were at it. Security and facilities had keys to all the offices and while I never expected an interruption, it wasn't worth the risk.
Putting dead bolt lock on my door was too obvious and against company policy. I checked out alternatives at the hardware store and I was introduced to a door brace. It fit under the handle of the door and was jammed at an angle on the floor. I tested it and I couldn't budge the door with the brace in place. That gave me a renewed sense of security and with the brace in place we were more relaxed. Cathleen loved to fuck and feel my cock in her pussy so we did it anytime my schedule permitted. On busier days we resorted to oral sex. Tuesdays and Thursdays were still reserved for the hotel or car after aerobics.
ONE WEDNESDAY IT WAS ANAL
One Wednesday Cathleen had a surprise for me. She came to the office dressed in a wrap around skirt. The skirt flowed with her sensual movements. Under her skirt she wore stockings held up with a garter belt and silk panties under her garters. It was the first time I got to see her with stockings and garters and she looked very sexy. Cathleen told me that she was going to the ladies room to get ready for anal sex. It would be the first time we would do that in the office. She surprised me again when she handed me a butt plug. We had never used one before and I knew she was up to some mischief.
Cathleen returned from the ladies room and entered the office. I closed and locked my office door behind us and then I placed a door brace under the door handle to prevent any of the building personnel from entering. I turned her toward my desk and told her to place her hands on the desk top. Cathleen leaned over and put her hands on the desk looking over her shoulder as if she was wondering what I had in mind. That's what I loved about Cathleen; as many times as we had anal sex, she acted as if it was her first time. I lifted Cathleen's skirt up and draped it over her back baring her stocking encased shapely legs and her panty covered curvy ass. I ran my hands over the bare skin between the tops of her stockings and her panties and smiled as goose bumps appeared on her skin. I loved running my hands over the tiny mounds of flesh that arose when Cathleen got excited.
I took a hold of her panties in both hands and slowly lowered them down baring her flawless ass. I pulled the panties down as far as they would go inside the garters. Cathleen gasped as her ass was bared and she once again looked apprehensively at me as if she was unsure of my next move. I caressed her bare bottom gently in my hands relishing the feel of the smooth firm buttocks. Then I knelt down behind Cathleen and lovingly placed kisses on her luscious ass. I kissed and then gently nibbled on the enticing ass flesh drawing moans and groans from Cathleen. I kissed my way to the center of her bottom and let my tongue dip into the crack of her ass.
Cathleen trembled and gasped when my tongue moved up and down her crack. I put both hands on her buttocks and gently pried them apart exposing her anus. I loved looking at her cute rosebud just before I probed it with my tongue. Cathleen let out a soft scream when my tongue touched her tight aperture and she shivered slightly. I began to lick Cathleen from her anus to her vagina and within minutes her pussy was soaking wet. Cathleen was breathing rapidly and moaning as I kissed, licked and probed her two love holes.
Then I stood up and retrieved the lubricant from my desk top and applied it to Cathleen's anal passage. Cathleen squirmed when she felt the cool lube enter her ass and the goose bumps returned on her bottom. Next I eased my finger into her ass and pushed it all the way in to the last knuckle. Cathleen's body went rigid momentarily as she adjusted to the anal penetration. I finger fucked her ass slowly and I felt the passage loosen up around my finger. I added my middle finger and ring finger to her pussy and then finger fucked both of her holes simultaneously.
"Oooh, agh," Cathleen moaned with pleasure.
I added more lube and then I took a butt plug that she handed me and inserted it in her ass. Cathleen again groaned as the plug spread her anus and then disappeared in her rectum. Her sphincter instinctively closed around the rubber plug. I stood up and had Cathleen turn around to face me. Cathleen knelt down on the carpeted floor and pressed her buttocks against the front of my desk. Then she reached up and unzipped the fly to my trousers to free my throbbing erect cock. She fished my cock and balls out of my boxer shorts and trousers holding it her hand. Cathleen stared at my impressive member for a few seconds before she began to lick up and down the shaft. Then she covered my cock with her sensuous mouth.
"That's it, get my cock hard and wet for your ass," I whispered excitedly.
Cathleen had a talented mouth and it didn't take long to bring me to the height of desire. I lifted Cathleen back to a standing position and had her turn toward my desk again. She removed the wrap around skirt as she leaned over my desk. Then I pulled the butt plug from her ass and we both heard the audible pop. Moving closer to Cathleen I let my cock brush against her buttocks and then positioned my cock head against her anus. With a gentle but firm steady push my cock spread her flower and the head disappeared in her asshole.
"Not too deep at first and then deeper," Cathleen reminded me placing her hand on my thigh.
Cathleen said that every time that we had anal sex even though I was always gentle with her. I slowly fucked her ass letting my cock go a little deeper each time. I was in no hurry to sink my cock all the way in her ass and I loved to watch it slide in and out between her beautiful hillocks. Cathleen groaned each time I went a little deeper but her groans were in pleasure not discomfort. My cock eventually slid all the way in and my pubic hair brushed against her buttocks. I held her lovely ass in my hands as I fucked it slowly never wanting it to end.
As much as I wanted to fuck her forever in this position I felt my release start to build. Cathleen was frantically rubbing her clit and fingering her pussy in search of her own orgasm. She would usually manage to have at least one orgasm before I ejaculated and that day was no different. Cathleen moaned out loud when she climaxed and her sphincter muscles tightened around my cock. Her body thrust up and down and she rolled her ass when she came. I held to her buttocks and picked up the pace fucking her. Then I felt my pending release.
I pulled my cock from Cathleen's ass and aimed it at her anus and buttocks. The first stream hit her right on her anus and then the subsequent streams landed on her back and buttocks. I then pushed my cock back in her ass and Cathleen milked the remaining cum from my cock. She handed me the towel and I wiped her back and buttocks clean as my cock softened in her rectum. My cock eventually slipped from her ass and I wiped it clean with the towel and then I wiped my seed from her anus.
Cathleen stood up and pulled her panties back up and put on her skirt. I pulled up my underwear and my pants. Cathleen smiled at me as I opened my office door and then she returned to her desk. I checked my watch and saw that it was almost noon and time for lunch. I still couldn't believe that we finally did anal in my office.
TUESDAYS AND THURSDAYS
I loved anal sex and I was thrilled that Cathleen did too. It was always erotic for me to have her on all fours and watch my cock slide in and out of her sweet ass. I had seen plenty of porn but I never got the idea of fucking a woman's ass in the missionary position or with her sitting on my cock. I guess it was good for porn but not for me. If I wasn't watching my cock in her ass, what was the point? Cathleen liked the spoon position too and that was usually reserved for sex in the car. She liked having my cock in her ass while I fingered her pussy and played with her tits.
We often did it in the car in the spoon position. One night after aerobics, we went to the tavern 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.
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 on her left side. I prepared her ass with the lotion and my saliva. I pushed my trousers and shorts down past my knees, lubed up my cock and got behind her on my side. It was tight quarters but I managed to get my cock into her ass and started banging her hard. Cathleen pushed back 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 soaking my fingers. I lay next to her until we recovered. We cleaned up the best we could and headed home in our own car.
Another time on a Tuesday aerobics was cancelled because the instructor called in sick. Cathleen and I went to the tavern instead of a hotel due to the short notice. Cathleen and I sat side by side at a bar table facing the bar. The bartender was engrossed in the TV watching a ball game and getting caught up on all the scores. As we ate our burgers and sipped our beers, I ran my hands over Cathleen's nylon covered thighs. She was wearing hose under her dress but no panties. I slid my hand between Cathleen's thighs and covered her pussy. I rubbed her cunt and her pussy got sopping wet. We finished our burgers and beers and then left the Oasis. When we got out to the parking lot I asked Cathleen if she wanted to sit in my car for awhile.
"You better believe it, as worked up as you got me in there you better take care of me," she replied excitedly.
Cathleen and I got in the back seat of my car and I immediately lifted up her dress. I lowered my pants and underwear to my knees and the two of us played with each other for several minutes. The car had louvered rear windows so it was impossible for anyone outside the car to see in the back seat. There was something very erotic about being partially clothed but still having access to each other. Cathleen had her legs spread wide as I fingered her pussy and pushed her cunt juice into her ass. Cathleen stroked my cock with her hand as I prepared her for another ass fuck.
I never knew anyone like Cathleen who could get so wet during foreplay. My hand was sopping wet and within minutes I had her asshole coated with her own pussy juice. I positioned Cathleen so that she was kneeling down on the back seat and I knelt behind her. I put my cock in her pussy and let it soak in her juices before I lined it up with her ass.
Once again Cathleen reminded me, "Not too deep at first and then deeper."
I eased my cock into her asshole as she maneuvered her body to accommodate the anal penetration. Cathleen had her head down on the car seat turned to one side and I watched her face grimace slightly as my cock made its way into her ass. Cathleen moaned and groaned as I slowly fucked her going a little deeper in her ass with each thrust. Once I was all the way in I picked up the pace and fucked her until I flooded her ass with my cum. Cathleen had her fingers buried in her twat and she brought herself off as I plowed her ass. When my hips stopped moving Cathleen milked my cock with her anal muscle and then her hips gyrated as her own orgasm overtook her. I had to hold her tightly to keep my cock in her ass as her hips jerked out of control.
My cock softened and I eased it out of Cathleen's ass. I knelt there looking at her recently violated asshole and watched as my semen trickled out of her rectum. Cathleen remained still for a few minutes with her dress thrown up over her back and her ass on display. I had some paper napkins in the car and she used them to wipe the semen from her ass before she sat down on the car seat. We waited until my car windows defogged and then she went to her own car and we drove to our homes.
I started to get a little nervous with us using local hotels for our encounters. So far so good that no one had recognized us but I started to worry a little. Many of the vendors that called on our company used local hotels and I did not want to be spotted by any of them or anyone else that would know us. I mentioned this to Cathleen and she suggested a place called The Chateau. I had heard the name but I knew very little about it.
The Chateau was a romantic interlude that had a variety of rooms to suit one's taste. The room that Cathleen and I liked the best contained a Jacuzzi, water bed and mirrored walls. All of the rooms contained TVs with adult entertainment as well. The Chateau added enjoyment to our sexual encounters.
The first time we went to The Chateau was memorable. We entered the room and wasted no time taking off our clothes as the Jacuzzi filled with hot water and bath gel. Cathleen and I showered together before entering the Jacuzzi. We soaped each other up and played with each other's bodies being careful we didn't cum in the shower. Cathleen 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 Cathleen leaned back into me and I reached around and stroked her cute titties tweaking and rolling her nipples in my fingers. I slid one of my hands down across her firm abs over her little blond tuft of hair and found her vagina. I played with the folds of her labia and then inserted my fingers in her pussy. I found her hard clit and rolled it between my fingers as I continued to tease her nipples with my other hand.
As Cathleen got turned on I moved her to the other side of the Jacuzzi and had her lean over the edge presenting her shapely ass to me. Her ass always looked good but this time it glistened with water and bath gel and looked so sensual. I leaned over and licked Cathleen's pussy from behind driving her wild. Then I had the urge to tongue her beautiful ass so I swiped my tongue from her pussy up and over her bung hole and back to her pussy. She gasped out loud when my tongue touched her asshole. I really got into it and grasped both of her curvy ass cheeks and pulled them slightly apart so that I could get my tongue in deeper. I probed her pink aperture with my tongue as I inserted three fingers in her pussy. She started whimpering, gasping and directing the action.
"Oh my God, do it again. Lick my asshole; stick your tongue in there. Eat my pussy, tongue my ass, rim me, oh yessssss," she cried out.
I grabbed the bottle of wine and poured some in the crack of her ass letting it trickle down over her anus and pussy. I placed my mouth on her and drank up the wine swabbing her pussy and ass in the process. I repeated this several more times until Cathleen seemed to go into convulsions with her first orgasm of the evening. She collapsed back into my arms and I stroked her smallish tits as she recovered from the intensity of her orgasm.