A Descent into Despair

Fbailey story number 816


Fifty Year Old Girlfriend


I was devastated when I lost my wife. It might not have been so bad if she had just up and died, but no! She fucking divorced me. For a God Damned eighteen-year-old girl. Can you believe that? After sticking my cock, my tongue, and all of my fingers into her pussy for over thirty years she decides that she likes having a girl’s tongue stuck in there instead.

I must admit that the divorce was simply and quick. The eighteen-year-old’s father was a judge. My wife didn’t want anything and didn’t take anything except her clothes and other personal items.

None of my divorced friends could believe that I got out of it that easy.

So anyway I had people coming out of the woodwork trying to set me up with women that they knew.

I let them and I took each and ever one out on a date. A real date with dinner, drinking, and dancing.

I actually found out that I had a lot of money left over without a wife to feed, buy clothes for, or to give money too all of the time.

I had a Friday night and a Saturday night date for about ten weeks.

I got to know a wide variety of women that some other guy had gotten tired of fucking and had divorced. Just some other guy’s hand me down.

Not all twenty women were losers but they certainly were promiscuous. They all let me feel them up and seventeen of them let me fuck them on the first date. The other five sucked my cock claiming to have been on the rag or something.

Interestingly six of my Saturday dates stayed overnight and serviced me on Sunday morning too. By saying that they serviced me is to say that those women fucked my brains out…literally. My cock was sore for a day or two afterwards.

Some of those women were really strange. Some were depressed, most were angry, and yet others were just fucking crazy.

Then I met a woman that my sister of all people set me up with.

Jewell was a very sweet lady and certainly lived up to her name. She was a loan officer in a big bank in town. She was tall for a woman at five feet nine inches and wore three in heels to make her an even six feet. She was thin with B-cup breasts, and long brown hair to her waist. As I found out later she had short trimmed pubic hair and pierced nipples.

She was intelligent and could carry on a conversation during dinner. She was funny too. She had on a real silk blouse. It was white and her white bra showed through it nicely. Her black skirt was made of some elastic material and clung to her body. It was fairly short too. I noticed that Jewell did not adjust constantly, like other women did when they wore short skirts.

I took her to Red Lobster for their Endless Shrimp. She could eat and didn’t mind using her fingers either. When she sucked her butter covered fingers it looked like something very seductive, like out of some video. Her lips looked luscious and the way she used her tongue excited the hell out of me. Then there were her eyes. Her lashes were long and her eyes were green. They were probably tinted contacts but who to hell cares? They were gorgeous.

Jewell liked her rum and had three Margaritas during dinner and two more when I took her dancing. That babe could line dance with the best of them. She said that if she had known where I would be taking her that she would have dressed more appropriately. I bet she looked great in tight jeans, boots, and a cowboy hat…but she looked fantastic in what she was wearing.

By the time that we were ready to leave that skirt of hers had risen to the point that men everywhere were getting hard…including me.

Jewell said, “Your bed or mine?”

I looked at her in that outfit and said, “Your bed” because I wanted to see what else she would wear for me.

As I drove her to her house I asked her to put on a fashion show for me. She said that she had the perfect items in mind.

It turned out that she had quite a selection of sexy negligees. And I do mean sexy. She thought nothing of being naked in front of me and dressing just to undress again and again. She was teasing me until I couldn’t take it any more.

Then she just melted in my arms as I lay on her bed. She had ridiculously high count Egyptian cotton sheets. That woman certainly knew how to live well. Her bed was made of hand carved mahogany. It had four posts with silk drapes that were tied to the posts. There were shelves and drawers built into the headboard. The top of the bed was a mirror that filled the space between the posts.

Jewell saw me looking up and said, “When I get on top you will really like the view…from below…and from above. I know that I always do!”

Then she kissed me, held my cock in her small gentle hand, and kissed me again. She cupped my balls and kissed my cock before straddling me. Then the most extraordinary feeling came over me as she sank down onto my standing penis with her totally wonderful pussy. I had never in my life felt a pussy that marvelous. It felt something like an old washboard, a ringer washing machine, and riding your bike down the railroad tracks all rolled into one. The ripples, the squeezing, and the vibration were way too much for me.

She smiled down at me and said, “Let it go baby. Give it to me. I’ll get it up again for you.”

I looked up at her beautiful breasts and face and I looked past her into the mirror at her nice firm ass as I let the first load fly.

Oh my fucking God!

In all those years of marriage I had never once enjoyed sex more than I was at that moment.

Jewell and I never got dressed the rest of that weekend. We didn’t leave her house until Monday morning when we had to go to work. Neither one of us could wait to be together again.

I was in love…

Explore my other stories

THE END