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Older woman Stories

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My First Time

I was eighteen and she was a grown woman

Back in 1995, I had my first sexual experience. I was eighteen at the time. She was a grown woman, about ten to fifteen years older than me. Where do I begin? Right after graduating high school, I delivered newspapers first thing in the morning. I mostly took the job as an opportunity to work out on my bike. I had another, better-paying job later on in the day, but the extra money was good and I was keeping in shape. Star...

Classic Ride

A Milf in a classic ride offers him a completely different kind of ride.

It was a beautiful, late summer night. There was a bit of a chill in the air, but nothing a light jacket and jeans couldn’t remedy. The moon was full, so I kept the fire low – barely more than the coals I’d used to cook dinner earlier. I’d finally earned a week of vacation at my first real job, and I was indulging a long-denied need to get out of doors for more than a night. All my friends either were off to college or co...

Harriet And The Book Club

Sordid events late at night in the library.

Harriet's heels clicked against the polished floor as she walked between the rows of bookshelves, her hips swaying naturally with each stride. Sunlight streamed through the windows, illuminating her silky raven hair and the graceful lines of her body beneath her fitted blouse and midi skirt. The supple curve of her waist flared into round, lush hips, her skirt hugging every delectable inch. Oblivious to the appreciative g...

Cum On My Glasses! Chapters 4 & 5

College student finds himself torn between two very different lovers

I was tied up with school work for the next few days, but before long Friday rolled around, and my dinner date with Mary Sue Henderson. We had decided to go to Rocco's Tacos. I waited for her in the dorm lobby, which connects the men's and women's towers. The elevator dinged, opened, and there she was, right on time at 5:30, wearing a blue fuzzy sweater and jeans. Her long blonde hair was in a ponytail and her fingernails...

Cum On My Glasses! Chapters 2 & 3

College student finds himself torn between two very different lovers.

The next morning, I woke up an hour early for class. Stuart was still snoring in his bed. I was fully awake and alert, firing on all cylinders, and full of energy! The encounter with Professor Milford had certainly given me a boost in my self-confidence that was sticking around. I got to class early, got a good seat, and followed the lecture with rapt attention. I even raised my hand and answered a few questions. My other...

The Enveloping Requirement: Part 6

The disciplinary weekend draws to a close, but will it end there?

“Yes, Christopher. You flirting around my female staff members is something I take seriously. I can not have that in my corporate facility. I need you to be concentrated on doing what I require from you, that is one hundred percent efficiency,” Miss Lexington said loudly, as she grabbed his face and forced him to look at her. Chris was feeling very nervous now as he didn’t think it was that bad that he had touched her hee...

Cum On My Glasses! Chapter 1

College student finds himself torn between two very different lovers.

My cock was jutting out longer and harder than it ever had in my life. Professor Milford, kneeling before me, reached out and grabbed the shaft from underneath. Her fingers were smooth and cool, and I sucked in my breath at her touch. Her red fingernails stood out in stark contrast to the smooth pink skin of my shaft. She began slowly stroking it, forward and backwards. She looked me dead in the eyes. "I want you to cum a...

The Better Man, Chapter 6

Jack learns his place (with some help from Mona) and learns that he loves it!

I drove while they canoodled in the back seat. I could hear Anna slurping on Mason’s cock. When I parked the car, they straightened their clothes and hurried into the house ahead of me and went straight to the bedroom. I entered just in time to see Anna pull him by his cock onto the bed with her and guide it into her pussy. She lay on her back with her legs around him as he fucked her vigorously while I stood and watched....

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The Enveloping Requirement: Part 5

Christopher Robertson lands himself in further bother during his disciplinary weekend with his boss lady, at her pristine home.

The lights had been out in Miss Lexington’s bedroom for around ten minutes. Chris had been lying awake, thinking over the last day and a half, here at Miss Lexington's immaculate home. He wanted to know, what was it about the Sunday Telegraph that Miss Lexington was looking forward to. He thought it was best to get to sleep and see it play out in the morning. Just as he was starting to drift off, he suddenly remembered th...

Once I walk into the kitchen, I look at the time and see it's now ten after six. That means Janice has fifty minutes to get here. If she doesn't, I will just have to drive over to her house and remind her we are both consenting adults with a sexual desire for each other. She needs to admit her sexual desire, and attraction for me is not a bad thing, it can be a satisfying thing and so much fun for both of us. "Hey, Roman,...

The Enveloping Requirement: Part 4

A day and a half into his disciplinary with his older, female boss at her pristine home, Christopher Robertson is going to find it getting a little warmer as he inquires about her methods.

Back in the bedroom with the door closed, the female opera music was playing louder than usual. Miss Lexington was pouring the champagne into the two glasses. She handed one to Chris and told him to sip and swirl it around his mouth before drinking the whole glass. She then told him to undress and bend over the bed. Being totally obedient to her demands, he did as he was told. Miss Lexington watched him whilst sipping her...

The Enveloping Requirement: Part 2

After being summoned to attend his older, female boss’ home, Christopher Robertson has found himself in a disciplinary procedure that is most unusual.

Walking up the stairs, Chris followed as Miss Lexington led the way, returning to the pristine, main bedroom. The room was lit, with ambient light from lamps in each corner of the room with brighter, warm-white LEDs above the headboard wall. Female opera melodies were playing out around the room. Miss Lexington pointed to the bed. “Lay out the pages, and cover the bed in the same manner I had them. Be sure to wrap the pil...

Elagabalus

In Ancient Rome, an emperor may not be who he seems.

The harvest had been bad that year, and there had been outbreaks of plague in the city. The streets of Rome were even less safe than usual as gangs of hungry bandits roamed around, looking for anyone with gold. Also consider the alleged madness of Elagabalus, the boy king, for so they still called him, though he had come of age in the fourth year of his reign. Factor in the increasingly frail hold the old Gods still had o...

Four Years

After four years together, a young man must say goodbye to his college admissions officer.

Six in the morning—such was my body clock. Four hours earlier, I was grateful that Marc had turned down my offer to suck him hard yet again. Seconds before that, for the third time that long night, his voluminous fluids had mixed with mine. “Just a little nap first,” he said then. “A nap?” I pouted. I scowled. I wasn’t about to admit that I was done as well—very well done. “Well, you’re not napping on top of me,” I snappe...

Under New Management

She doesn't realise it, but Maggy takes her first step toward becoming the workplace slut.

She wasn't sure who, if anyone, was to blame. Did she start it, that day in the changing room? Or was it him and the way he looked at her? It wasn't really important in the grand scheme of things, but people seemed to be interested. Margaret had worked there for almost twenty years. The hours suited her when the kids were small. The extra money was nice when they were older and she could do more hours. Now, after the divo...