Nancy was 18 years older than me.
An unhappily married woman, with long wavy red hair, 5'5" tall, average breast size (C cups) and with a nice curvy ass to hold on to. The two of us were introduced by my parents of all people, at the local watering hole we all hang out at. Quite often we would sing karaoke together, put down shots at the bar, dance and occasionally go out dancing to other places.
Nancy's marriage was dead. While there was a time she loved her husband to death, their marriage over time just weakened. The two of them stopped having sex years ago and don't even sit down at the dinner table together. He's not a bad guy. I met him a time or two. A pretty good looking guy for his age, a hard worker and very friendly.
He wasn't at all a controlling person and pretty much let her do whatever she wanted and on his dime.
I certainly didn't appear as a threat to him given how young I was compared to her and also because he just didn't seem to be at all concerned with who she hangs around with. Over the years she prayed for a divorce but she didn't want to initiate the divorce herself fearing that she would be financially ruined because he was the person bringing home the bacon.
As good as the two of us got along I never had any intentions of being anything more than friends with her, simply for the main fact that she is married. Happy marriage or not, I just don't 'Do' married women because I have in the past and it would only lead to problems down the road. Sure there was a 'Chemistry' between us and people have mentioned it but in the same breath they never encouraged it and rightfully so.
When we would dance it was difficult for that spontaneous erection not to pop up on the dance floor. Even though I know she could feel it brushing against her, she never mentioned it.
There was just something 'Taboo' about dancing with an attractive, untouchable married woman who is much older than me. I also knew she showed an interest in me sexually but maintained discipline because of her marriage and my age. Until the time we spent the night at the Casino. For a few years we talked about going on a casino trip together, strictly as friends.
She called it her favorite place on earth and had a lot of 'Rewards Perks' which included free meals and rooms.
We were able to schedule our casino trip because it fell on a weekend where neither of us had to work. I met her at the casino lobby that day and she brought me to her room. She had already spent the night with her (Lady) best friend who left earlier in the day before I arrived.
I went up to the room, dropped off my stuff, we showered and went gambling. I had a surprisingly good stroke of luck at a particular penny slot that I played for not even ten minutes before I hit $1000 and had to discipline myself to stop gambling for the night.
I watched her gamble away a fortune before we had dinner, grabbed a few drinks at a night club that was inside the casino before going back to the hotel room. We both were feeling mildly tipsy by the time we got back to the room and a little tired. We poured ourselves another glass of wine from a box we had and put on the clothes we were going to sleep in. I wore white boxers and a t-shirt, she had a one piece night gown that screamed 'Grandma' as I almost forgot that she was so much older than I was.
Not exactly an outfit that appealed to my libido. We had separate beds and I was lying on mine, sipping my wine, watching TV as she laid on her stomach facing the end of her bed and was fidgeting with her tablet. We engaged in light conversation at first. Then we began to discuss our sex lives, I was seeing a girl that was an on again, off again friends with benefits type deal.
She discussed her broken marriage and voiced her total unhappiness with the lack of a sex life. Even though she was a woman in her mid to upper 50's, she wasn't dead and longed to have somewhat of a resemblance of a man who could please her.
While we were talking, I got up with my glass of wine and made my way over to the end of the bed where she was laying on her stomach. I actually had really got up out of my bed to walk to the window to look at the beautiful view but since her bed was so close I stopped right where she was. Amongst our conversation I sprung a hard on that was impossible to hide in my short white boxers.
"Someone's excited!" she yelled pointing at my crotch with a coy smile. "Shit! How'd that happen?" I said jokingly. "Do you know I could see the outline of your thingy through your white boxers?" she said. "Really?
Oh shit! I'm sorry. Does this make you uncomfortable?" I asked her.
"It should but I can't help but stare" she said back. "Well, I can't just make it go away" I said laughing. "Well, I have a confession to make, maybe it's because of the wine we're drinking and the fact your hard on is staring at me through those boxers and the fact that I haven't been fucked for years but you know when we dance?" She said as she began to slur her words.
"Yeah" I replied. "Well I could feel that thing poking me on the dance floor" she said. "Yeah, well I kind of figured you could" I said as I began to move closer to her. I moved close enough where my erection was practically hitting her in the face and I saw her pupils begin to grow larger.
"Oh man! I can't believe I'm actually gawking.
You're young enough to be my son" she said as she stared intently at my cock. I then took a huge risk trying to call her bluff and lowered the top of my boxers so that my stiff cock popped out and almost hit her in the face. She sat up, turned around and positioned herself where I was at the end of the bed. "You want to touch it?" I asked her trying to see how far I could take things. She began to lightly stroke my cock with both hands while looking in my eyes.
"You know I'm going to hell for this. If you tell anyone about this I'll fucking kill you" she said in a semi-serious tone. "You can kiss it if you want to" I said to her continuing to push the envelope.
She then slowly began to administer tiny pecks up, down and all over my cock. "I can't believe I'm kissing your cock" she said to me as her tiny pecks turned into bigger smooches.
"Go ahead. Stick it in your mouth" I slyly said to her as if she was waiting on my order. She wasted no time and began to slowly move back and forth with my cock in her mouth. I could feel her tongue slide slowly back and forth across my shaft.
She moved slowly as if she was savoring every square inch. After a few strokes of her tongue she stood up and removed her night gown.
Her tits weren't as saggy as I thought they would be for her age. They weren't so small that I couldn't get a handful, her nipples were tiny and hard. Her pussy was well groomed and the rest of her body was inviting enough. She took me by the hand without saying a word and escorted me to the other side of the bed.
She rolled down the blankets and we both crawled in. I let her crawl down between my legs and she sucked my cock slowly for a good ten minutes.
Normally I enjoy it when a woman sucks fast and sloppy but for some reason this felt incredible and I was hardly able to contain not busting a nut in her mouth but I held out in anticipation of what was to come. She then made her way back up between my legs, leaned over and kissed me before carefully taking my cock and slowly inserting it into her extremely wet cunt. She rode me on top for a long time.
She started really slow and picked up the pace. She soon was riding me so hard she had to grip the headboard and the bed was shaking as if it was going to break! "Oh my fucking god!" she screamed as I could feel her cum more than once as I let her have her way with me. I then sat up, leaned her on her back and buried my face in her succulent warm pussy. It didn't take long before her hips were shaking uncontrollably. After a few minutes I leaned up and stuck my cock in her as she laid on her back.
"Thank You" she whispered as I looked in her eyes while thrusting my cock in and out. I fucked her good and hard. I wanted to give her what she wanted. What she didn't have for years.
I must have fucked her for a good 15 minutes before she told me she wanted me to cum inside her. After I left my load inside her she just laid there quaking for a few minutes trying to catch her breath. I laid next to her trying to catch mine. A few minutes later the two of us passed out.
The next morning we woke up in each other's arms and she began to get worried and feel guilty about what we did. I assured her that nobody would know about any of this as I crawled my way down her body and buried my head between her legs eating her pussy for one last time.
She came good and hard and once again thanked me for all that I had done for her.
We got up, showered and went about the rest of our day.