older woman sex stories – Page 4

Unnatural Desires

★ ★ ★ ★ ★

0 average (0 rating(s))

--==+==-- Miss Barbra was pleased with herself. She had finagled a whole week off from work and planned on spending the entire time at the beach. This was what her Dennis, her son, had asked for his ninth birthday. She was glad to be able to do it. She had felt guilt in the past for the time she spent on the job and she felt like this was a good start in making up for it. They arrived and checked out their room. She was pleased, it was neat and clean. He was pleased, it was barely fifty feet...

READ MORE

Tags: masturbation, mommy, nightgown, older-woman

Trick or Treat

★ ★ ★ ★ ★

0 average (0 rating(s))

Henry felt like an idiot. Here it was, Halloween. All his friends were out egging people's doors, throwing water balloons at cars, and just generally causing trouble -- exactly what every 14 year-old boy SHOULD be doing on this day in a small town ... exactly what he should be doing. Instead, thanks to his mom, who had to work an extra shift tonight, he got stuck walking his little sister Trish around for trick-or-treat. It just wasn't fair. He loved his sister and all, and she wasn't nearly as much of a pain in the ass as some 8...

Tutor’s Lonely Wife

★ ★ ★ ★ ★

0 average (0 rating(s))

When I was 15, I was struggling with math class and my mom arranged for an accountant she knew from work to tutor me in private lessons at his nearby house. He was apparently a very busy man, because sometimes he would show up and sometimes he wouldn't. However, his wife was always home and was always very friendly, kind and courteous. In fact, I was enamored of her... a typical schoolboy crush for an older, very attractive, more sophisticated woman. Even though I had a girlfriend at the time, I'd hang out with her during aborted lesson times anyway...

READ MORE

Tags: doctor, medical, nurse, older-woman

The Wicked Landlady

★ ★ ★ ★ ★

0 average (0 rating(s))

***Need House to Share:*** ***Woman and teenage son.*** ***Please call 555-1234*** Tommy and his mother Pat had moved in with Mrs. Carol three months ago. Mrs. Carol quickly called Pat after seeing her ad in the paper. When they came over she told Pat the rent was half what she had originally intended to ask. The reason was Tommy. The teenage boy was simply adorable and she wanted him under her roof. Pat jumped at the chance to rent space in her lovely Victorian home, and Mrs. Molly Carol seemed like such a nice, benign older woman. After they moved...

The Woman in Apartment 3B

★ ★ ★ ★ ★

0 average (0 rating(s))

I lived in an apartment building in New Jersey when I was 12 years old. My bedroom window looked across an alley to the bedroom window of apartment 3B which was occupied by an older heavy set woman of about 58. She wasn't anything special but she was the first woman I saw naked, she was also the first woman I saw masturbate and the first woman who ever let me touch and lick her. It all started one night when I woke up in the middle of the night and saw the light on in 3B. I went to...

READ MORE

Tags: bath, bathing, masturbating, masturbation, older-woman

Tommy Has an Owie

★ ★ ★ ★ ★

0 average (0 rating(s))

Tommy has an owie Part 1- 4 Little Tommy Jenkins was, as they say, not the brightest bulb in the box. Although this was due more to his strict, religious upbringing, and overly protective mother, than any mental deficiency. Never the less, he very often gave people the impression that he was much younger than his real age, which was twelve. Lately he'd been having a problem. His body, which was not hampered by any outside influences, was starting to respond in a manner quite common to adolescent boys. To put it in his words, his pee-pee was growing and...

Tommy’s Wicked Stepmother

★ ★ ★ ★ ★

0 average (0 rating(s))

"And I want you to be in punishment position when Miss Caulder arrives Tommy". The boy was mortified upon hearing this over the dinner table. His stepsister Julia looked at him and snickered. What his stepmother was saying was that he would have to be totally nude for the visit from his 7th grade teacher tonight. These punishments began shortly after the death of his father. Whenever his stepmother, Sondra, felt he had misbehaved she would strip off all his clothes and humiliate him somehow. After dinner Sondra said "Julia, be a dear and help Tommy get ready for tonight"....

READ MORE

Tags: anal, anus, bath, bathing, humiliation, older-woman, punishment, rectal, rectum, stockings

Tom Part 1

★ ★ ★ ★ ★

5 average (1 rating(s))

Tom was a happy teenager who lived in a city apartment with his mom and dad. He attended Washington Junior High School, where he would graduate in three months. He was captain of the school baseball and basketball teams as well as the debating team. Tom was handsome, athletic, a very good student and was very mature for his age. Although he was very popular with both the boys and the girls in school, he had no steady girlfriend but did date frequently. One Friday night when Tom was eating supper with his mom and dad his father announced that...

Tracy Has a Pizza Delivered

★ ★ ★ ★ ★

0 average (0 rating(s))

By Slippy Three nights ago Tracy Hunter was out shopping and headed home when she got an idea what to do about dinner. Since John was out of town and she didn't want to go to a lot of fuss, even as hungry as she was, an idea came to her mind that would prove to be one of the best ideas she had in a long time. " PIZZA! That's it," she thought, "I'll have a PIZZA! Humph, maybe I'll get it with extra pepperoni!" Tracy pulled her sporty little convertible into the Pizza Palace and strutted inside. Of...

READ MORE

Tags: bath, bathing, older-woman, punishment, stockings

Travels with Aunt Leigh

★ ★ ★ ★ ★

0 average (0 rating(s))

Part 1 Troy was at that age when a growing boy walks around with a, more or less, perpetual erection. And there’s only one thing on his mind:sex….sex, sex, sex, and more sex! It was driving the kid crazy! And it didn’t help that he lived alone with an attractive “older woman” -- his 40s-something aunt, who also happened to be a good-looking blonde. He remembered when his roommate, Patterson, first met Aunt Leigh, at one of those parents’ days at Hillcrest Academy. Standing at the window of their room, Patterson took a moment to eye up the slender blonde...

The Tests 10-2

★ ★ ★ ★ ★

0 average (0 rating(s))

The week following Gladys' party Felicia called Sally. She wanted to have coffee and talk so Sally arranged a meeting at the usual coffee shop next to the interstate. It was Felicia's day off so they met when Sally was on the way home from work. Felicia arrived first and Sally met her at a table in the back. They made small talk for a while and got to know each other better. "It seems like you had something specific on your mind, Felicia," said Sally. "Yes, I really do," replied Felicia. "I feel I can talk to you honestly...

READ MORE

Tags: bath, bathing, older-woman, satin, stockings

The Truth, The Whole Truth & Nothing But The Truth

★ ★ ★ ★ ★

0 average (0 rating(s))

This is a true story, although it happened many years ago, I remember it as though it was yesterday. Only minor details have been changed to protect identities. It happened to me when I was 21. I was still living at home with my parents at the time. My sister (Kelly) who is 3 years older than me, left home and got married (to Eddie) at the age of 17. Kelly had a gorgeous little girl called Amy who was 4 years old. I often visited my sister on a Saturday afternoon to see my niece and play with her,...

The Unexpected Physical

★ ★ ★ ★ ★

0 average (0 rating(s))

By the time Jason climbed off his bike and walked it over to the rack, he was sweating like crazy and could barely feel his legs. It had taken him nearly an hour to pedal up the hill to the high school -- in August heat, no less. But with both his parents at work and no friends who drove, it was the only way to get to his sports physical. He couldn't wait until next year, when he'd be 16 ... old enough to get a permit and start driving himself places. Jason leaned his bike against the rack,...

The Week That Changed My Life

★ ★ ★ ★ ★

0 average (0 rating(s))

Prologue- This is the story of a young boy, his neighbor and his sister. The memories of that young boy's experiences live in me still, but I cannot tell this story from his perspective, I can only tell this story from the perspective of the man, forty years his senior, that I am today. The time of this story is 1962, the place is Southern California, the 'Greater Los Angeles Area', as it was known. For the sake of those involved I won't specify the location any more closely than that. This was a time before the Internet and the...

The Shooter

★ ★ ★ ★ ★

0 average (0 rating(s))

First of all, I am not some super-endowed stud who can perform sexual feats of porn-star proportions. I am fairly normal in size, but maybe thicker and with a large penis head. This attribute has lead some partners that I have been with to say that I am well-endowed, something that 5 minutes of viewing adult video proves to be false. However, if there has been one part of my physical sexuality that has intriqued some women in the past, is the intensity, volume, and distance of my ejaculations. Thus, since I live in a small town and have had...

READ MORE

Tags: older-woman

The Strict Aunt

★ ★ ★ ★ ★

0 average (0 rating(s))

Aunt Cecilia had lived alone until the day her sister died in 1955 she was forced to take in her sixteen year old nephew. She enjoyed living alone and was not offended by the term old maid or spinster, she enjoyed her job as a librarian and thought a good book and a hot coffee an enjoyable evening. At 43 she was still quite attractive but considered plain due to her glasses and the way she wore her hair tightly bunched up in a bun and also for her penchant for tweed skirts and sensible shoes. No freedom was given...

The Surprise Blizzard

★ ★ ★ ★ ★

0 average (0 rating(s))

We open the scene in the early morning of a non-descript February weekday, in a house 90 minutes outside of Boston Time was just 6am. James and Wendy were in the kitchen, The Television was on the local new show the hosts were asking the weather guy about today "A picture perfect day ahead folks details at 17 minutes after the hour." Wendy was dressed for the day. So Wendy was organizing the kids things for school, She was so busy that she didn't notice that James Sr. was wearing a long Tee shirt and Jockey shorts as he was...

The Scavenger Hunt

★ ★ ★ ★ ★

3 average (1 rating(s))

*** A young man overcomes his lack of confidence by using a scavenger hunt ploy to introduce himself to widowed mature women. (Fm-teen, inc, 1st, anal) *** From the Journal of Damon Wentworth as Augmented by Katrina Ruza Prologue The events of the year 1992 culminated with a birthday party for Damon Wentworth at my home. In addition to celebrating his 19th birthday that evening we were marking the end of a one- year pact we three mature women had with Damon. The pact came about through an ingenious naughty mission this young man through a very clever scavenger hunt....

The Seduction of Aunt Jodi

★ ★ ★ ★ ★

5 average (1 rating(s))

John just turned eighteen and it being the start of summer he was home reading the want ads cause he still didn't have a summer job. His mom and dad both just left for work and he was sitting at the kitchen table wearing only his jockey shorts. His tanned fit body had matured quite a bit since puberty and he worked out all the time. John liked the looks he got from all the females at the beach or the gym where he spent most of his time. He always was able to seduce some young fox into sharing...

The Older Woman Next Door

★ ★ ★ ★ ★

0 average (0 rating(s))

This story begins when I was a Senior in school. I was your typical 18 year old . I loved to go to parties and like every kid my age, I tried to get laid. I never was successful, so I had to resort to looking at dirty pictures in a magazine and jacking off. Life was unfair, but when our new neighbor's moved in, my life was about to change. The family consisted of Mom and Dad and one little guy of 3. Mom's name was Barbra and as I learned later, she was 41. Her hair was long...