An Anal Evening with Kristen
As I waited for Kristen’s flight from Philly to deplane, I thought about our very unusual relationship. Kristen was 33, divorced from my former best friend Jim. This was the first time Kristen and I would be together since the divorce. I was 50, living with my long-time girlfriend Victoria and our daughter at her home in Chicago, but I was taking advantage of their absence for the week-end to sneak time with Kristen.
Kristen and Jim were dating the first time she and I fucked. She had flirted with me so insistently that, against my better judgment, I took her to dinner. We ended up at her place later. Not sure where to take things, I excused myself to use her bathroom. When I returned, the lights were low and Kristen stood in the middle of her living room wearing only her panties, bra, stockings and heels. What was I to do? Of course I fucked her. I fucked her on her sofa, I fucked her on her dining room table, and I fucked her in her bed.
We had a couple of sleepovers together after that before Jim found out. To this day, I think Kristen confessed to get Jim to hurry up and marry her. Kristen was a coldblooded, calculating cunt, but aside from the damage to my friendship with Jim, I came out ahead. He and I patched things up to the extent that I saw Kristen and Jim socially. She kept up her flirting, discretely, doing things like feeling my crotch whenever Jim would leave the room and stealing kisses. Eventually, Jim left her for an older woman with a lot of money from a divorce. Kristen and I stayed in touch by phone and email after I moved to Chicago and she readily accepted my invitation to visit for a week-end.
Kristen’s flight was on time and we made our way through typical Chicago traffic downtown to the hotel where I had reservations. Staying at a hotel allowed me to avoid getting Kristen past the doorman at my building and also to avoid the risk of running into neighbors on the elevator. We checked in, went out to a nearby restaurant and went dancing after dinner. By the time we got back to the room, we were both ready for sex. I got undressed and climbed into bed naked to wait while Kristen finished in the bathroom. She was naked when she returned. My eyes devoured her sexy long legs, broad womanly hips and her eraser nipples poking out from her small firm tits. The most striking thing about Kristen though was her large, wide mouth with the most sensual big lips I had ever seen. It was thrilling kissing those lips and even better when she used them on my cock.
After I enjoyed her lips for many minutes, both on my mouth and then my cock, I stretched her out on the bed, spread her legs and started kissing her thighs and belly before moving down to her clit and labia. I loved eating a woman out and I keep at it for a long time. It’s the best way I know to guarantee a great fuck and even a mutual orgasm, which I love. Kristen was very responsive as usual and her groans and outcries assured me I still knew how to get to her. I eventually moved down to her little anus and devoted my attention and tongue to it before I started using my fingers. Kristen’s big sexual secret, which she was shy about sharing with men, was that she preferred anal intercourse to vaginal. Ironically, I had learned this from her husband, who was proud to share it with me.
This night I decided to get to the butt fucking quickly and once I had her dilated and lubricated with my tongue and fingers, I penetrated her vagina only long enough to get lubrication on my raging hard-on. Her eyes widened with pleasure when I withdrew and placed the head of my penis on her anus. It was so well prepped it yielded easily and I enjoyed watching my penis slide smoothly into her hungry sphincter. She gasped few times before I penetrated fully. I looked down and smiled to see that my cock was completely buried in her ass. I withdrew slowly and deliberately and paused with only the head of my penis still inside her. I liked the way her anus clung to me. I started penetrating again, faster this time and repeated this again and again each thrust getting harder and quicker until I was really pile-driving my cock into her and I was making smacking sounds as my abdomen slammed into her ass.
Kristen got more and more vocal: “Yes, yes, YES, fuck my ass, fuck my slut ass, fuck my slut ass HARD!”
She started playing with her clit now and was really getting frenzied. I knew her hard jutting nipples were also one of her strong erogenous spots so I leaned back a bit, still thrusting but a little more gently and freed my hands to reach for her nipples. I took them between my thumbs and forefingers and started pulling and twisting.
“OH FUCK YES!!!” she screamed “OH FUCK YES JUST LIKE THAT!!!”
I could feel her sphincter start to spasm around my penis. I felt warm juices from her cunt bathing the base of my cock and Kristen started bucking against me, pounding her ass into me in a frenzy as she moaned and screamed. Suddenly she lost control completely, and I felt her warm piss added to her pussy juices pouring onto me. I leaned back on my knees, my hands on the bed behind me, and enjoyed the spectacle of her bouncing and flailing on my cock as she came again and again.
Finally she started quieting down. She took her hands, both fingers if which had been deep in her pussy and crossed them on her chest, holding her little tits. Her eyes were closed and little by little her breathing slowed. I stayed still, enjoying the warmth of her rectum on my cock.
Finally I broke the silence: “Alright Kristen, you slut. Now I’m going to turn you over and I’m going to fuck your ass doggie style, then I’m going to fuck your face with my cock straight out of your rectum and come down your throat!” And that’s exactly what I did.
An Anal Evening with Kristen