Okay. You know the drill. This happened a number of years ago, and the names have been changed to blah, blah, blah.
Still with me? Good.
Kim was a hot, early 30s MILF. She was short (only about 5 feet tall), long blonde hair, small A-cup tits, shapely hips, and a beautiful ass. She also had gorgeous eyes, a wicked smile, and a slight Southern accent (that became more pronounced when she drank or was turned on).
We worked together at the same high school, and we started flirting with each other almost immediately after meeting (I, too, was in my early 30s at the time, and I had recently lost a lot a weight, so I stood about 6’ tall, tipped the scales at about 180, and had light brown hair). Soon we started fucking pretty regularly. This had been going on for about a year, and she was — without a doubt — the best lover I ever had. Before we started hooking up regularly, she had gone through an extended dry spell (almost seven years — ever since her daughter was born), but once we started connecting, she was eager to make up for lost time. We totally connected in bed, and we communicated our wants and desires openly. This made for mind-blowing sex, including the night we tried anal for the first time.
One night I met Kim and her daughter at a local park. They were there for a night of “Movies in the Park,” and by the time I arrived, the movie was just about over, so they were ready to go home. I put Kim’s almost-sleeping daughter in her car seat, gave Kim a quick kiss, and drove us all back to Kim’s apartment. By the time we got home, Kim’s daughter was out cold, so I carried her gingerly up to the apartment and put her to bed in her own room. While I was doing this, Kim excused herself to her bedroom. After tucking Kim’s daughter in bed (and making sure she was sound asleep), I made my way down the hall and into the master bedroom. Kim was already naked and lying on her side by the time I came in. She looked at me with those beautiful blue eyes when I walked in, lightly traced a finger over her already alert nipples and said, “Do you want to fuck me?” I didn’t need to be asked twice.
I stripped down as quickly as I could and climbed into bed. Kim moved to the head of the bed and was flat on her back, legs spread apart. I took a moment to kiss her deeply, suck and lightly bite her nipples (she loved this, and her moans made my already hard cock jump a little), and then move down so I was directly facing her glistening cunt.
I loved eating Kim out. She had the sweetest tasting pussy I have ever encountered, and I routinely stayed down there until she orgasmed at least once. Tonight was no exception. I began by alternating between licking and flicking her clit with my tongue and then diving deep into her glory hole, trying to fit my entire tongue in there. She bucked her hips against my face while I did this, and I knew she was close to cumming. To put her over the edge, I continued to lick and to suck on her clit as I inserted two fingers into her. The sensations of my tongue on her clit and my fingers slowly sliding in and out of her pushed her to her first orgasm, and she moaned and grabbed my hair as she came.
I moved back up so we were face-to-face, and — for the first time ever in our relationship — she took my hand and sucked her juices off my fingers. I almost blew my load right there. We kissed deeply again, and she pushed me on my back. Kim was always willing to “return the favor” when it came to oral sex. She greedily took me in her mouth, almost swallowing it whole immediately. She then started sucking on the tip and jacking my shaft with her hand. Soon, her head was bobbing up and down on my cock, and I was moaning in ecstasy. Her oral skills were amazing, and she knew from experience I was close. Sometimes she would encourage me to blow my load in her mouth, but tonight we both wanted to fuck as well. So she released me from her mouth and climbed on top of me.
Her pussy was like a vice, and I loved it when she was on top. She leaned down so I could inhale her gorgeous tits while her hips rocked back and forth on my member. My hands found their way to her ass, and I squeezed and slapped those cheeks as I thrust my hips in rhythm with hers. During all this, one of my fingers found its way to her starfish, and I slowly inserted it. This was not new for us (we’d been experimenting with some anal play for a while), but I could tell she was into it tonight by the way she moaned and locked eyes with me when I did it.
Soon she pushed off me and turned around and got on all fours. We both loved doggy style, and I quickly got on my knees, grabbed her hips, and slowly slid my cock into her beautiful slit. However, after only a few thrusts, she looked back at me and said, “Do it.”
I knew exactly what she meant (during our anal play, we’d talked about anal sex), but this was the first time we were really going to do it, and my heart started pounding in my chest. I pulled out, and she reached around and grabbed my cock, lining it up correctly. She asked me to go slowly, and I obliged. I gently pushed into her, feeling her ass resist me at first, but once I got the head in, open up and accept all of me.
If Kim’s pussy was the tightest I’d ever felt, then her ass was on an entirely new level. I have always prided myself on how long I could last in bed, but this was so overwhelming (in the best way possible), I knew I wasn’t lasting long if I wasn’t careful. Still, I did my best to hang on, and I drove into her ass while Kim reached between her legs and alternated between rubbing her clit and playing with my balls.
Before long, Kim said she’d had enough (this was a new experience for her, too). I slid out of her, and she rolled on her back. In a flash, I was back inside her deliriously tight pussy, and I pounded her hard missionary style. After just a few thrust, she moan-whispered, “I’m coming. I’m coming,” and I felt her pussy clamp on my cock. That sent me over the edge. I exploded into her with one of the biggest orgasm I’ve ever had. I then collapsed beside her, and we finished off the session by kissing, lightly fondling, and smiling at each other.
It was one of the hottest sexual experiences I’ve ever had.