The Older Whore
by Tony Tiger
Copyright© 2020 by Tony Tiger
Erotica Sex Story: An older woman still likes sex but mostly when she gives it away instead of selling it like she has done much of her life. She reminisces about fun times in the past while enjoying them in the present. Currently a small group of teen boys were in her "stable" but she showed compassion for a needy older man as well.
Caution: This Erotica Sex Story contains strong sexual content, including Mult Teenagers Tear Jerker Sharing Gang Bang Prostitution .
Mary never did get married but she had a hellava lot more sex than any wife she’d known. Besides fucking for fun she’d sold her body at various times to support herself. She made some college tuition money doing fraternity parties and later supplemented a low-paying job by escorting on weekends. Her boyfriends rarely knew about those “side” pieces. A couple of live-ins that didn’t last long convinced her that cohabitation wasn’t meant for her.
Her body was average and her face nice to look at but neither beautiful or homely. She kept her dark brown hair cut pixie style. Playing tennis several times a week made her body trim and in good shape. Her personality let her blend in too.
Sex usually happened when you got her clothes off, something that got easier and easier to do as time distanced itself from that age of fifteen and a half when the first man to visit her vagina showed her how enjoyable it could be. That steady babysitting job for the single father gave lots of opportunities for her to learn what it was all about, including birth control.
As the saying goes, “Once the door is opened...”, her sex life blossomed. Being smart enough to be discreet still allowed for plenty of experience. By the time she was twenty-five, with the help of lovers and johns, she’d tried just about everything that could be done and had decided that good ole friendly copulation with the appropriate foreplay and some relaxing closeness afterwards was the best, but most other kinds were worth doing too.
That brings her to now. With the half-century mark not far away, Mary took stock of her life, best done when an interesting man wasn’t naked or physically connected with her. Those situations tended to take her focus away from philosophical thoughts.
“Hmmm,” she mused, “I’ve had an awful lot of ‘Mister Hards’ but no ‘Mister Right’. A few have been good friends and a lot more were good lovers but I’m doing ok the way I am. I’ve been thinking about those crazy high school days lately. Maybe I ought to be thinking about a special birthday party for myself.”
She was renting a small cottage by a lake and had a local high school boy taking care of the lawn and other miscellaneous maintenance. When her regular lovers dropped off to a single weekend date-and-fuck she was quite horny, as you might expect with her history. She never wore much in the warm weather and began deliberately being barely covered when Brad was around. She noticed his looks and she managed some cleavage and up-the-loose-shorts shots. His bulge looked interesting and when his shirt came off she could see that he was athletic.
Over some iced tea after a workout when he was quite sweaty she made her move. “Brad, do you play sports?”
“I’m on the JV football team and some track events. Why do you ask?”
“You are pretty well built. I was wondering if girls go for the jocks like they did when I was in school.”
“Yes, they seem to.”
“Does that include sex too? Was pretty common as I remember.”
Now he looked a bit embarrassed, “Sometimes” was all he said.
She pushed her point, “Do you get any and if so how do you like it?”
He bolded up a bit, “I’ve had a few but it isn’t like I’ve read about.”
“How is that?” she asked smiling.
“Well, first of all we have to find a private place and then it’s rather quick and a one-time thing, like I’m getting added to a scorecard. The girls I date don’t seem willing to do it, just the groupies, I think you call them.”
“I do understand what you mean and feel. I’ve had a lot of sex in my life and it can sure vary a lot. I only have one boyfriend now who I see on weekends and that’s not enough for me. I really like you and would love to show you what good sex is like.” She stopped and watched him closely.
“Did I just hear what I thought I did? You’d have sex with a kid like me?”
Mary smiled and reached for his hand. Holding it gently, she replied, “I guess you don’t know that enjoying a young hunk like you is supposed to be every older woman’s fantasy. Hell yes I’m interested. Wanna see the playing field?”
He nodded vigorously and she stood up to make a little dance of removing the few items she was wearing. “Now let’s see the other player’s equipment!”
He was hard already as she expected. Very respectable organ with nice hairy balls dangling below. She knelt in front of him and gently cupped his scrotum as her mouth explored his very upright young shaft with a big mushroom head. Brad gasped, “Oh God that feels good. You are lovely!”
They were both sweaty but neither cared as they lay on the porch rug. He grasped her tits and she guided him to be gentler as well as what else to do to make them feel good. Her hand pointed his tool below her furry patch. Oral sex would have to wait until they were cleaner.
Her hands on his hips set the pace and he moaned and groaned with each stroke. The internal rush of hot cock fluid happened about as quickly as she expected for a young and eager man. “Keep moving and give me more,” got excellent cooperation and she came twice before his second. They finally kissed as he lay carefully on top of her.
“Damn, that was good! Can we do it again?” he asked.
“Sure! Women don’t have the limitations you men do.”
He was curious, “So how many times have you done it in a row?”
She was thoughtful, “I lost count, being kind of busy, but the guy that took me to the fraternity party said he thought eighteen times in a row, but some of the men took seconds. Then he did me too. I think I could have done more but they wore out.”
Brad got hard hearing that and began moving again without withdrawing, “You are sooo sexy. I want to hear about other stuff you did too.”
That was a great compliment she thought, “OK, stud. We’ll work on your skills as we talk, OK?” He pounded out another one which took a nice long time and included a position change. He was well drained and she was quite slippery so the fun lasted. Then they showered and he had to get home.
He was naked with her every other day and she still had her weekend guy for a bonus fuck or two. That was more like it. Brad soaked up her teaching and became quite good especially with the energy of youth. Once he got through the biggest part of the exploratory phase she asked if he had any friends who were “sexually deprived”. That made him laugh, “Most of them!”
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