14 Memorable Anal Encounters 05

I never knew anyone like Charlie 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 Charlie 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 Charlie 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. Charlie 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. Charlie 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. Charlie had her fingers buried in her twat and she brought herself off as I plowed her ass. When my hips stopped moving Charlie 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 Charlie's ass. I knelt there looking at her recently violated asshole and watched as my semen trickled out of her rectum. Charlie remained still for a few minutes with her red 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.

"You definitely have the largest cock that has ever been in my ass. Do you know how big it is?" Charlie asked.

"Well Karen measured it one time when she was blowing me and she said it was almost 8 inches long and just over 5 inches around," I replied.

"It certainly felt bigger than that tonight," Charlie sighed.

"At times I do feel thicker and longer but I have never thought about my size very much," I admitted and added, "I know that there are plenty of cocks bigger than mine."

"I think tonight was one of those nights that you peaked and your cock is plenty big for me," she said with a giggle.

Charlie did not bother putting on her pantyhose when I pulled up my pants. I opened the car door and we got out of the back seat. Charlie said that she was glad that she ran into me and that she would see me later, then she said goodnight and made her way over to her car. I watched as she got in her car and as she did her skirt flew up and flashed her bare pussy. After she left the parking lot, I drove home in a very sated state.

It was at least another week before Charlie and I met up again. It was a repeat performance with me stripping off her pantyhose in the back seat of my car, lubricating her ass with her own juices and fucking her tight ass. It was exciting for me to strip off her hose and fondle her legs, pussy and ass. Charlotte seemed to like being without her panties and hose in the back seat of the car. I took my time with her, fingering her pussy and ass driving her crazy, until she finally begged me to fuck her in the ass.

The final time it was another night at the Oasis and Charlie had had too much to drink. I put her in one of the booths toward the back to let her sleep it off and I told her girl friend Ginger that I would take her home later. Ginger and Al were anxious to get going that night and they didn't want to wait for Charlie to wake up. They thanked me and left and I joined Dan at the bar for a night cap. I didn't drink too much since I was driving and after a while I decided to take Charlie home. I picked her up and carried her out to my car all the while I hoped that she wouldn't get sick. I placed Charlie in the front seat and buckled her in. Charlie woke up and told me that she was staying at her sister's pad that night. She managed to stay awake and give me directions to her sister's place.

Once we arrived at her sister's, I helped Charlie into the house and the guest room. It was late and I assumed that her sister was asleep in the other room. Charlie flopped down on the bed and I then had the urge to fuck her before I left. I moved over to the bed and stripped Charlie naked. I removed her blouse and bra, her shorts and panties and her shoes. Then I stripped down naked and got in bed with her. It was the first time that we were totally naked again since the very first time we had sex.

I rolled Charlie to her side and she knew what was coming next. I scoop her female juice from her pussy and used it to lubricate her asshole. Charlie cooed as my fingers probed her pussy and lubed her ass. Then I placed my cock in her pussy just for few strokes to get it slick. I positioned my cock at her ass and gently pushed my cock into her.

"Not too deep at first and then deeper," Charlie whispered those familiar instructions.

I did what she asked and as I fucked her ass I went a little deeper each time. Soon I was balls deep in her ass and I picked up the pace. My cock felt longer and thicker than I could remember at that moment. I reached around Charlie with my left hand and played with her tits and rock hard nipples. Then I moved my right hand to her pussy and pushed three fingers into her cunt. Charlie was going wild and she was creaming all over my fingers as I plowed her ass. My cock was throbbing in her asshole and I felt my pending ejaculation building in my balls. One more deep thrust and I held my cock there as I exploded in her ass. My cock pulsated as streams of cum shot into her ass. Charlie instinctively clenched and unclenched my cock with her anal muscles. She milked every drop of cum from my cock.

For some reason I stayed hard that night and I kept right on fucking Charlie's ass. I knew it would be a while before I came again so I pulled out of her ass and rolled her on her back. Then I pushed my raging hard cock in her pussy and treated her to an exhilarating fuck. I kept my cock in constant contact with her clit and I had Charlie writhing and trembling as a continuous string of orgasms rocked her body. Then I pulled my cock out of her pussy and rolled her back to her side and re-entered her ass. I pummeled her ass as I sought out my second orgasm of the night. Charlie's ass was loose and slippery from our combined juices but she was still snug enough around my cock. Once again I stiffened and fired a barrage of cum into her rectum. I could feel my cock pulsate again as it released a torrent of cum deep into her anal recess.

We lay still for a few minutes recovering from the intense fuck session. I had forgotten about my cock in her ass until it had softened and slipped from her hole. I felt my wet cock drop on my thigh and I knew that cum was trickling out of Charlie's asshole.

"I wish you could stay with me tonight," Charlie whispered.

"Not tonight Charlie, I have to be up early in the morning. Plus I don't think you want your sister to find us in her guest bed in the morning either," I replied.

Charlie just nodded her agreement and then I got up to get dressed. I dressed and left the house quietly and then drove home. It was the last time that I had sex with Charlie. Our company was going through some downsizing and Charlie was one of the casualties. She ended up taking a job with another company and she stopped hanging around the Oasis and her former co-workers. I still think back to our five anal encounters, two in my car and three in other people's homes. It was wild.

NEXT CHAPTER

The next and final chapter is devoted to my number one anal partner Cathleen. We had a five year affair and we had anal sex wherever and whenever we desired.