I must confess, I once had a strange affair with an older woman.
To make a long story short: I was in a long distance relationship. My fiance was finishing her master's degree overseas and we hadn't been together for years. I always made the effort to come stay with her for a month or so at a time, but by the end of her degree, she was just taking out all of her frustration on me. One day, she told me that we were over. I knew we'd eventually make up. We always do. I always apologize for something trivial that is no where near as horrible as she has been to me, she always reluctantly accepts and never brings up the other things we've fought over, and then that's it.
At the time, I had a penpal that I knew lived near me. We'll call her Jane, as I know she watches porn from time to time, and I don't know how she'd feel about me writing this out. I was still in my mid-twenties. She was an older lady I had met through a mutual friend in an MMO game, and we enjoyed writing to each other. She was married, had three grown kids, and some were starting to have kids of their own. She often gave me advice about my relationship and had always been good to me. When she found out I was single, she started to console me. I told her about how sexually frustrated I had been, since it was a long distance relationship, and how there was so much I wanted to do and try, but that my lady hadn't been interested in anything other than missionary, and even giving a hand-job was just "too much effort."
One thing led to another, and we started talking about our fantasies. She told me how her husband hadn't touched her in over seven years. Then we started talking about what we "would" do. Then we started cyber sexing. Then, since I knew she lived just one town away from me, we decided to meet.
The days leading up to our meeting, I couldn't help but feel wrong. I knew I'd get back together with my lady. I just avoided calling her, so our fight would stretch out. It's stupid, but I felt I could justify it because I was "single." But Jane had a family, kids, soon to have grandchildren. I can't imagine how she must have felt.
The day came. I got off work early and made sure everything was ready. She told me what car she would drive, and I told her what apartment complex to come to. I even bought her a set of anal beads as a gift, because it was something she had wanted to try.
I saw the car pull up, and a woman stepped out. She was very lovely. From all the stories she told me, I knew she had kids who were older than me. But she easily could have passed for being in her mid-thirties. She looked around, trying to find mine. I came to the door and called her in.
It was strange at first. We both knew why she was there, but we sat and had something cold to drink. We both seemed to be studying each other, wondering who would make the first move. At first we started talking about that stupid game we both played, and it helped us feel more comfortable. After a while we started sitting closer, and talked about what we wanted to do that day. She told me she had some kinks that she was hoping to iron out, and that one of them involved fucking a young boy. She started rubbing my thigh.
I took a deep breath and went for the tits. They were huge. She pulled them out of her buttoned shirt and told me to suck on them. She also asked me to call her mommy.
At first it was weird. I had this huge tit in my mouth. I was greedily sucking on it, like milk really would come out. She had me sit on her lap, facing her. She held me and bounced me. Then she slowly unzipped my fly and pulled my cock out. She went to the bathroom with me and put down a towel. Then she shaved me, and started calling it a weewee instead.
It felt strange being on the floor, but having my penis shaved felt so good. It was smooth and soft. She started licking my balls and gently stroking it. She stood above me and played with it like it was a cute little toy, though most women before had complimented me on my size. In some ways, it was emasculating, but it also felt good just to have a tender loving woman caring for me.
She kept me completely undressed and brought me back to my couch. She turned me over and started spanking my bottom. She told me I was a bad boy for wanting to play nakey.
After a while, we moved on to the next event. She let me pull down her panties and stockings. She lift her skirt and showed me her dark hairy muff. I dove in, face first, looking for her pussy under all that hair. It was pungent, but somehow the smell just turned me on. She was already soaking wet, and it just poured into my mouth. I loved every drop.
We laid down on my bed and I started fucking her. She had wide, motherly hips and her tits were like pillows to bury my face in. She kept holding my ass cheeks and patting them lightly to keep a good tempo. I hadn't been wearing a condom, as she told me not to. It had been so long since I'd had sex, even the most vanilla of it felt great.
We eventually tried everything on our lists. She got her age play in, and I licked her asshole. (I have a thing about giving ladies oral. I just like to lick holes, front or back). She gave me a tit-job with those giant pillows. I tied her up and shoved her new buttplug in. She sucked my cock and stroked my balls all day. She let me watch her piss, and she let me lick her clean.
Towards the end, there was one last thing she wanted to do. She had never taken the plug out of her ass, and said it felt great. She laid me down and tied me up. She made sure I could still see and that I was comfortable, but that I couldn't get out. Then she started licking my asshole. Then she put some KY on it, and slid her finger inside. I didn't fight it, but I hadn't been expecting it. She started licking my nuts and slurping on them, sliding in and out of my ass. She laughed a little and kept teasing me about how my asshole was tightening around her, and my penis was twitching.
She started going faster and pressing harder. I could feel the pressure building up inside of my ass. She started sucking on the tip of my penis and tickling the rest of my penis with her free hand. I felt the finger in my ass wriggling around faster and faster. It built up to the most intense orgasm of my life.
I watched her cheeks fill up as my penis pumped cum into her mouth. Her eyes jumped open, and she had to pull away. A few drops fell on my lap. She looked at my cock and then back up to me. She opened her mouth and showed it to me. Her tongue was swimming in a thick pool of cum. She started trying to gargle it, and then swallowed. Then she licked up the rest of the cum on my lap.
After that, we got cleaned, dressed. We went to lunch together. She kept the butt plug in the whole time. I wanted to keep her panties, but I didn't ask. I figured they were too nice to just suddenly go missing. She gave me a kiss, thanked me for a wonderful day, and went on her way.
For a few months, we kept in touch. But I did eventually make up with my lady. We're still together.
But rarely, on the few occasions that we do have sad, boring, routine sex. I think about that day.
