14 Memorable Anal Encounters 06

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 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 and 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 magnificent ass was framed by her thigh high hose and her short blouse ending at her waist line. She actually looked hotter by keeping the blouse on.

I ran my hands all over Cathleen's ass, thighs and pubes feeling her wet pussy. I slipped my finger into her vagina and then added a second one. I took some lotion from my desk and I pushed a finger between the cheeks of her ass and massaged it 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 whispered 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 sphincter muscles tightening them. I pulled my fingers from her holes and I stood up behind her. I dropped my pants and boxers to my ankles and brought my rock hard cock to her buttocks. I let it rest against the hot flesh of her ass and I leaned over and whispered in her ear.

"Where do you want it first today? Do you want it in your ass or do you want me to fuck your pussy first?" I teased her and then licked her ear.

"Fuck my pussy first and then my ass. I want you to cum in my ass," Cathleen murmured.

I then eased my cock into her pussy and fucked her from behind until Cathleen orgasmed once again. Then I moved my cock to her ass and fucked her for a short time before I unloaded my semen in her anal canal. Cathleen looked so hot leaning over the desk with my cock sliding in and out of her asshole that I just couldn't prolong my ejaculation any longer. I leaned over her as 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. 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

We desired to spend at least one night together and wake up in the morning naked in bed. Cathleen suggested that I let her attend a seminar and that I could stay in the same hotel. I sent Cathleen 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.

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 Cathleen 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," Cathleen remarked as she positioned herself to straddle my morning erection.

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 Cathleen 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.

Cathleen 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. Cathleen 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 her in her beautiful ass again. I loved anal sex and Cathleen 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. Cathleen 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 blonde hair as her head bobbed up and down on my dick. She would pause every so often and lower her mouth as far down as she could taking in most of my cock. Cathleen 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. Cathleen 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.

Cathleen 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 Cathleen and our five year affair. My mind drifted back to the start of our affair.

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 Cathleen. I only stayed at the pool until 3:00 PM and then I returned to my room to shower. Cathleen 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.

Cathleen 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. Cathleen 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. Cathleen then got dressed and returned to her to change clothes while I called in our order. Cathleen 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. Cathleen 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. Cathleen 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.

Cathleen 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. Cathleen 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. Cathleen never bothered to wipe the semen from her feet. She was anxious to be rimmed again and I was ready and willing. Cathleen 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 Cathleen 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 Cathleen 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 Cathleen milked my cock with her sphincter muscle.

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 Cathleen 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 Cathleen 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 New York and accepted the position. Cathleen elected to stay behind even though I offered her a position as my assistant with the firm. We had a going away party on a Friday evening. After the party Cathleen ended up back at my condo with me and for the first time in five years we had sex at my place. Cathleen stayed through Sunday evening and we never left my condo. We had sex for two straight days and it was as if Cathleen wanted me to never forget our final hours together.

I met some very pretty women in New York and had sex with some gorgeous ladies. As good as it was I still remembered the times with Cathleen. 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 Cathleen standing next to me with my fingers in her pussy and ass. I would never forget those days. The vision of her incredible ass has stayed with me to this day.