Smile4U, My Mistress Allison

I've posted several stories on this site and this one is again a true story.  It's about a woman I met in a chat room around the Y2K time period.  So, in reference to my previous stories this is years after my story of myself and coworker Gerry.  And years before my buddy Ed.  Allison is what I consider my only real mistress.  We met in a chatroom and after discovering we lived in the same state thought it would be interesting to meet.  

Our first meeting was at a public place and pretty uneventful, other than me talking her into showing her tits to me and getting a few squeezes in while we were parked in a secluded parking lot.  We chatted more for a month or so, then we were able to set up another meeting.  I drove to her apartment, her husband was out of town.  We spent time in the bedroom and this was my first time to be naked with her.  Allison was a handsome woman.  10 years younger than myself, I was 40 at the time.  She had medium length hair, pretty eyes, strong yet feminine facial features.  Her body was beautiful,  curves in all the right places, big round tits, D cups, nice wide hips, nice round ass, muscular shapely thighs.  Her pussy was completely shaved.  As we got undressed, seeing more of her as she took her clothes off my cock grew and grew until it was bouncing around throbbing.  We cuddled and kissed, my hands exploring all of her body.  She was on her period so we didn't do much more than cuddle and kiss.  She did let me put the head of my cock in her but only for a moment.  Neither one of us came but it was very intimate and we really enjoyed just holding each other.  

Another meeting was scheduled after a few months.  One that would give us a day and night together.  If you ask how a married man could get this much free time, I can only say work and business friends can often present opportunities to those willing to take the chance.  As for her, he traveled a lot, which cast doubts in her mind and opened up the way for an opportunistic SOB like myself.  

The weekend of our meeting arrived and we met at a park.  We talked, kissed and cuddled, killing time to allow for check in time to arrive.  Again, business friends open up lots of opportunities.  So checking in was not an issue.  We got into the room and started taking each other's clothes off, I suckled and kissed Allison's big tits, her nipples were about this size of a dime, surrounded by large areolas, at least 3 inches across.  As I was doing this my hands were rubbing her belly and pussy lips, again shaved smooth.  I myself had trimmed my pubic area and shaved my balls.  This she loved and knelt down and started to kiss, lick and suck my cock and balls.  I pulled her up and led her to the bathroom where got into the shower.  Once there we started to soap each other up, her body felt fantastic in my hands.  Her hands felt fantastic on me.  I turned her around and started rubbing her ass, all around in big circles, on each beautiful cheek, up and down her ass crack.  She bent over and hiked one leg up on the edge of the tub.  I started rubbing deeper between her ass, running the tips of my fingers across her hole.  She was moaning and pushing back farther against my hand. I reached around her waist with my other hand and slipped two fingers into her wet pussy.  She started moaning that she was cumming.  I eased one of my fingers into her little hole and she shook, spastic, as she moaned louder, crying out, "Oh God, I'm cumming so hard!"  I rubbed my fingers a little faster in her pussy, trying to rub her clit at the same time.  As I did this I could feel her little hole squeezing down on my finger, so I kept stroking in and out of it.  She kept moaning, "Oh God, Oh God," until she leaned farther forward to get away from me.  She was on her knees now, I knelt down behind her and ran my arms under hers, squeezing her tits and twirling her nipples in my fingers.  The shower was raining down on us.  I kept on easing her orgasm as I kissed her neck, she was arching back.  I whispered in her ear if she would massage my hole, we had chatted about such things over the months and since I had fingered her, I wondered if she would follow through with me.  She looked surprised, but also eager to do it.  I stood up and turned around, like she had done. I put a foot on the edge of the tub, bent over and spread my legs.  I felt her hands begin to spread my ass apart and felt the tip of her finger against my hole.  She swirled it around the edge and started pressing against it.  The rubbing and swirling felt good, but I have to admit her pressing her finger against my hole felt strange and a little uncomfortable.  But I stayed patient, not wanting to ruin things, cause when I turned to look at her she was really getting into it and it wasn't like she was trying to jam her finger in.  I pushed my ass farther back as she had done and she finally eased her finger into my ass.  The feeling was pleasurable now and I understood why she had squeezed her ass down on my finger.  When I squeezed down as she was stroking her finger in and out the sensation was quite intense and pleasant.  I was really getting into this and one of her pushes went deep enough to press against my prostate.  This was like an instant rush of blood, swelling my cock shaft and head to the max.  I moaned, and she asked if I was OK.  I told her yes, and asked her to keep pressing against the bulge she felt deep in my ass.  As she pressed against it again she asked if that was what I was talking about and I moaned yes and pushed back farther.  She was able to get in really deep so instead of a poking feeling it was a steady constant pressure.  She asked what it was and I said it's my prostate and moaned that keeping the pressure against it was making my cock feel so good.  She kept her steady pressure, massaging up and down on my prostate, she mentioned that my balls looked like they were tightening up.  I moaned, "I'm about to cum baby, if you keep it up I'm going to cum."  Hearing that she pulled her finger out saying, " I want your cum in me, not on the tub." So we went and laid on the bed, still damp from the shower.  She began to position her self for me to fuck her missionary but I grabbed her and rolled her over so her ass was up in the air.  She moaned "mmmm, yes, fuck me from behind" but I surprised her.  Poking her hole earlier and feeling her finger fucking my ass had sparked a desire that had stirred in me for years, one that was always stopped and/or denied at home.  I spread Allison's beautiful ass but instead of mounting her I began to lick her little hole, when she felt my tongue against her ass she bucked and moaned, "Oh God, your making every part of me sooo horny."  I licked up and down her hole, swirling the tip of my tongue all around the edge, then lightly poking at the hole itself.  I could feel her trying to clinch her ass together and she moaned again "God don't stop, I'm cumming again," and she began to shudder and moan deeper and louder until she dove forward to get away from me again.  She turned her head and said, "No one has ever licked my ass, I felt so good."  Our inhibitions were completely and totally relaxed, I laid on top of her and kissed her deeply from behind.  I was grinding my cock hard against her ass, now it was time to sink my cock into her pussy.  So I rolled her back over and put her ankles over my shoulders, the look in her eyes was one of lust and fear, knowing that in this position she was going to be totally under my control.  No cover was put on, I had been snipped a few years earlier.  I positioned the head of my cock over her pussy lips, I glanced at her face and her eyes were fixed on my cock at the edge of her pussy. I lowered my hips and in one slow deep thrust I sank my cock as deep as I could into her pussy.  She gasped, I gasped, her eyes opened wider with surprise and amazement as she watched my cock disappear into her body, her pussy.  I kept my cock buried in her all the way, when she looked at me, I said, "You are so wet."  I then started to fuck Allison with deep deliberate thrusts, our hips slapping together.  She began to raise her hips up to meet my downward thrusts, we were both groaning and grunting, grinding our bodies together.  I started fucking her faster, I straightened my legs and got up on my toes so my angle of penatration would allow me to go deeper into pussy.  Her legs were practically over her head and we were face to face, the wetness of the shower had been replaced with sexual sweat.  Our eyes were fixed on the others, her head was bouncing against the pillow to my thrusts, we were like a sexual machine.  She later told me she had been in a continuous orgasm during this.  I kept driving my cock as deep as I could make it go, both of us moaning low to our rhythm.  As good as this felt I wanted a different angle at her pussy, so I raised off of her and rolled her onto her side.  I was kneeling between her legs and in fact still had one over my left shoulder.  I eased my cock back into her and started pumping my cock in and out of her, slower and more relaxed.  We both got into this position as I was able to now reach down and rub her swollen clit some, then reach up and play and squeeze those big tits.  I stopped sometimes in between so I could rub her belly, all the while steadily stroking her pussy with my cock.  She again started moaning, "Oh God, oh God I'm cumming."  When this orgasm subsided I told her I wanted to get behind her.  She told me, "Not before I taste my pussy on your cock."  I laid back and watched as Allison licked her pussy juices off the shaft of my cock.  It kept bobbing around, she smiled then grabbed it by the base to hold it steady.  She used her tongue to lick the underside of my cock head, right up the crease to my pee hole, then she licked all her pussy juice from under the edge of my cock head.  She gave me one last long lick down the shaft then turned around and put that sweet round ass high in the air.   

I got behind her, not on my knees but straddling her ass in a wide squatting stance.  I eased my cock into her, I was so close to cumming that any faster I knew I would cum.  She again started moaning, "Oh God, oh God, you are so deep in me".  My balls were against her pussy, I eased back out but kept the head in her.  I remembered from our chats how she liked being grabbed by her hips when getting fucked doggystyle.  So I grabbed her by the waist and grabbed hold of her tight, squeezing her hip bones.  I couldn't help myself and began to give her wild hip thrusts, she was bucking back and could feel my cock begin to swell.  "I can feel you about to cum," she moaned, "cum in me, shoot your cum in my pussy."  I bucked a few more times and started cumming, with each downward stroke I could feel my cock and balls pulsing, shooting my cum deep into her.  She kept moaning, "Cum, cum baby, oh God keep shooting your cum in me."  I pounded her pussy with some deep hard thrusts and was spent, I backed out of her and collapsed on the bed.  She turned around and again started cleaning my cock with her mouth, sucking our juice off my cock, it had begun to get soft but feeling her sucking it got me hard again.  She kept sucking until I was completely soft, but her mouth felt so good.  She crawled up to me and we just laid there, sweaty, holding each other.  I kissed her deeply and rolled her on top of me, we laid like that for a while.  She rolled off to my left side and snuggled under my arm.  I rolled over a bit so we were facing each other, we kissed slowly and deeply again and again.  I moved down to suckle her tits again and again.  I rolled her over so that I was behind her again.  Just holding her, Allison holding my arms tight, we fell asleep that way, not waking up for an hour or so.  It was still the afternoon and yes there was more love making later that night and the next morning.  I can write about those experiences in other stories later.