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Mature

12

Jared and Jennifer, Part 2

There relationship goes to the next level, and they never look back

My mind was racing. Did that really happen? Did Jared really kiss me? Why would he do that? And why did I kiss him back so passionately? I wasn't falling for this kid was I? I was. As I drove home I started to put things together in my head. When we had our first tutoring session, I was in a bad place. My life was falling apart and I didn't even want to be a teacher anymore. Jared...Read On

26

Jared and Jennifer, Part 1

All he wanted was good grades, he got so much more

I wanted to get straight A's my senior year of high school. I knew I'd need help so I signed up for my high schools tutoring program. Little did I know I'd be leaving high school with more than good grades. You might call it fate when I ran into Mrs. Brooks that day at the supermarket. My mom needed some things to make dinner and I offered to get them for her. As I was walking passed...Read On

9

Office sex

wife visits her hubsand at work

We backed toward my desk. She unbuttoned my shirt and I stuck one hand up underneath her dress, stroking the folds of her pussy gently. Alora rarely wore panties, and today was no exception. She was incredibly wet. I felt her spread her legs, so I obligingly inserted two fingers into her dripping sex, making her moan with pleasure and melt against my bare chest as I pumped her slowly. My...Read On

15

What A Massage

A massage never to be forgotten

So I answered the ad in the “Body Rubs” section of an online trade forum. The price was about twice the going rate for a therapeutic massage, so it sounded like it might be quite more enjoyable as well. When I arrived at the appointed time at the nondescript suburban home I went to the side door and rang the bell as requested. The lady who answered was good looking and about my age,...Read On

22

Years of wasted marriage then...

Two mature professionals meet and go wild for the first time

After becoming single at fifty and my children having flown the nest, I finally went online and met a lovely lady. This is the story of our sexual voyage together. Our first meeting was at a dog walk in the woods, she was attractive, bright, but a little reserved and I feared 'boring' as the talk was all about the difficult men she'd met. I didn't expect to see her again but I wanted to. ...Read On

36
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Natural Beauty Part 2 - The Date

Ellen’s date with Bob does not go quite as planned...

After a few months of chatting online with Bob, Ellen had agreed to meet him for dinner, followed by a night out. Not having dated since her husband, Ken, passed away, she was rather nervous about it and had used just about every beauty tip in the book to get herself looking good... **** Ellen caught herself admiring the tight little ass of the young Italian waiter, as she followed...Read On

23

His Mother's Best Friend

On the day of his mother's funeral, a young man spends some quality time with her best friend.

“You’re only 29, gotta lot to learn. But when your Mommy dies, she will not return.” The Sex Pistols, 1977 On the day Daniel Congress buried his mother, it rained like hell. Absolute buckets. The morning had broken bright and clear, but by early afternoon the sky was ashen and the wind had picked up. As the funeral cortege turned into the Colma cemetery the rain began to...Read On

13

The Curmudgeon's Nurse's Aide

Senor Citizen, hospitalized with a broken leg, is helped to recover by a beautiful nurse's aide

I've been living alone for the past ten years. I had a few live-in ladies during that time but now I‘m on my own. I mostly visit Senior Centers, scouting for those lonely ladies that hang out at such places. There were a couple of hot ones; I guess they figured it might be the last fucking they were going to get so they give it their all. Their pussies aren't as tight as they once were,...Read On

76

Cheating On My Husband

If He Won't Have Me, The Other Will.

I think, any woman who enters her forties can say that they like their ego rubbed once in a while. When you’ve had two children, and your husband no longer looks at you in the same way he used to, it’s always nice when someone else does. Even if it happens to be your twenty year old neighbor. I’m by no means unfit, I need to keep in shape to chase my kids around all day. I’m a...Read On

24

The Circle of Life

Old friends and their losses

My wife died suddenly. The little hospital waiting room, apparently reserved for those who will get bad news. Empty except for me. I dreaded the door opening, but it finally did. “Mr. Rogers? I am so sorry. Your wife never regained consciousness.” Her death was also unexpected. That morning I had wakened first. She was sleeping with her back to me, her shoulder bare. I put my hand on...Read On

16

Surprise Waiting, ch. 3

Amie has yet one more surprise.

My life had changed so dramatically since that day the voice on the phone said simply, “Hi.” Prior to that I knew I loved Amie, but the age difference was likely to get in the way of any lasting relationship. Or so I had thought. That day changed everything. After Amie and I made love for the first time--literal first time for her--I discovered how real her love for me really was. I asked...Read On

18

Meeting for the First Time

On line friends meet for the first time

We had been chatting on line for a few weeks now, and the conversations which had started as getting to know each other had begun to turn sexual. Annie was married with children but unhappy and knew life was meant to be better than this, and I was the same. Both of us were nervous but we decided to meet for a drink to see if we hit it off. Annie arrived in the pub we chose wearing a button...Read On

19
cooldaddy
online

Remembrance

The musings of an elderly gentleman

I remember what a woman’s flesh felt like. The soft warmth, the gentle curves, the swell of a breast, the ample fullness of the buttocks. I remember the feel of her body against mine, how we fitted together in sleep, my protective arm over her, my hand cupping her breast. I remember the impulsiveness of our youth, when we didn’t sleep, when the hunger of our bodies required an urgent...Read On

24

Probation Frustration

I met her while I was in a rehab program.

I was twenty seven and had been in a rehabilitation program for two years. It was an experimental program, and we had people in the field visit us to see what we were doing and how we did it. We had Judges, parole and probation officers, and even people from other programs. I was the public relations person for the foundation. One day, my boss introduced me to a probation officer from...Read On

11

Vintage Women III: Lust Will Find a Way

Broken bones are not going to spoil this woman's holiday

The story so far: a 42-year-old man calling himself Richie Benaud (although he isn’t) has found himself in the midst of a very sexy group of older women on a Saga holiday in the Mediterranean. With the women calling the shots – and also using celebrity names - he has had encounters with two of them, separately, and has been told that there is more to come . Gigi was out of commission with...Read On

21

Vintage Women II: The Substitute

The morning after the night before - and there's a new face

Waking up in Gloria Swanson’s hotel bed was a little strange. The first thing I remembered was the names business: she and her friend and I had adopted celebrity identities when we had met the day before. So I was cricket commentator Richie Benaud, Hetty was Gloria Swanson and Millicent was the 1990s tennis player Gigi Fernandez. Gloria and Gigi were much older than me, making a...Read On

15

Under Construction

She came.

"I expect you to be at my house around 9:30 tonight then," shouted Jason as I half walked half jogged to my truck. Seeing that it was already 6:54 I had hustle. My job as a construction site foreman was taking me out of town again. This time Jason, the owner, Richard, head foreman, Mike, the warehouse manager and myself were all going to take this trip. I decided to sleep over at Jason's...Read On

30

Vintage women

There they were again. A group of women the wrong side of middle age, traipsing around the town in this Mediterranean resort. I had seen them first in the museum, asking questions like good, polite visitors, speaking slowly and simply to help the staff, whose grasp of English was probably better on paper and in a classroom than in this live situation. Then I had seen the ladies in a...Read On

23

A run to remember part 2

After stumbling onto a cougars private beach on a run. Jake gets invited back to her home.

I just smiled and nodded my head. I followed Debbie back towards her house. My cock was throbbing at this point. Debbie's walk alone could make heads turn. Her beautiful heart shape ass swayed with each step. It looked so firm. I could not remove my eyes.  "I see you have got a little more comfortable looking at me Jake," Debbie said with a smile while she shook her ass a little. I...Read On

26

The Gift

An old man is shown that age doesn't really matter.

I don't know what I did. I was in my store and turned around and the next thing I knew I was here, in the hospital. When I woke up there was a nurse in the room with me and when she saw my eyes open she smiled and stood up. She took a washcloth out of a basin, wrung it out and sponged my face with it. I hadn't realized how hot I was. I looked up at her and she was beautiful. Black hair tied up,...Read On

25

School's Out for Summer

I met this older school teacher at a restaurant I worked at.

I was thirty-one and had recently relocated to Alaska. My first job was working at a small restaurant whose client base was construction workers who were building in the area. The restaurant was family owned. The woman owner was a large black woman in her fifties. One afternoon the owner came in with a short, petite, homely looking blond woman who was in her late forties. The owner...Read On

14

A younger man for Lansette

look around while next time in dvd store

For Lansette everything was happening very fast. She was busy looking in the local video store for something to watch late at night. When she looked up, she gazed into golden brown eyes that stared back into her green ones. She had seen him shopping in here before but never so close-up. On many of those occasions she would have had an imaginary conversation with him, but this time she was at...Read On

16

Strangest Encounter

I read her ad in the paper's personals column.

I was thirty nine and was and still living in Alaska. I was working for an advertising firm. One Sunday I was reading the ads and this one caught my eye. "I'm a seventy-three year old professional woman. Reddish hair, green eyes with slim build. Seeking companionship while in town on business trips." I knew I had to answer that ad. I found a photo of my uncle and I. I took scissors and cut...Read On

16

Who's the Boss?

She was V.P. /owner of a large travel agency.

I was thirty two and working for a large travel company that had nineteen offices across the state. Working there was like leaving a child alone in a candy store. But that's another story. Actually, several other stories. I was in the advertising department and one of my projects was designing and writing our news letter for corporate clients. My editor was an attractive fifty-seven year...Read On

16

China Doll

She walked in the bar about 9:30AM.

It was the morning after Halloween. I was visiting a friend in another town and I had gone to a party the night before. When I awoke, I decided I needed the "hair of the dog." I walked to the neighborhood bar about 9:00 AM. The joint was empty except for one old guy at the end of the bar, and the bar tender, and now, me. I ordered a bourbon and water. I drank the first one fairly fast,...Read On

18

Senior Nurse

Saw an ad in the Personals

At the age of thirty-five I had been seeing a much older woman weekly. Now that was over, I had a second encounter with an even older woman. That was over the same night it happened. I was yearning for another encounter when I saw an ad in the personals of the local paper. A woman in her late fifties would dress like a nurse and role play for a price. This got my attention. I called the...Read On

18

Encounter On The Bus

I saw a very large, older woman on the bus and knew I had to have her!!

I was 36 at the time. I worked swing shift and rode public transport. I'd catch the midnight bus. One afternoon I was on the bus and I noticed a homely, very large woman in her fifty's. She had a small female child on her lap. As I watched, she kissed the child's face several times. I became aroused and hard. I thought to myself, "I'd love to have her kiss my face like that." I decided I...Read On

39

Mature Landlady

True story about my experience with a mature BBW landlady I rented from

The name of the town I was living in was Washington, Indiana. The job I worked on was in Edwardsport, IN right outside of Bicknell. These were very small towns and very rural areas. My company was paying me per diem so if I found a room to rent I could pocket the rest of the money. I was getting $120 per day for food and hotel. Because of the rural areas the hotel choices were slim and way...Read On

22

The Halloween Party

A teacher and her former student reconnect at a Halloween party.

I had always loved dressing up for Halloween as a child and wearing fancy and colorful costumes and pretending to be someone else, even if only for a few hours. I truly looked forward to it all year, and getting to go to school dressed up and show off our costumes. The class parties where the teachers would bring in usually homemade treats, or the male teachers would bring in treats their...Read On

22

Old Alaskan Widow

At 33 years of age I met a 62 year old widow.

I was 33 years old at the time. I had a friend who had a service for dating. One night she called and needed a favor. She only had women in her stable and had been contacted by a 62 year old widow for some company. I had never done anything like that, but it was a Friday night about 10:00PM and I was home with nothing to do but watch the tube. I told her I'd call the woman. I phoned the...Read On