grandmother sex stories – Page 5

Gardening with my Mother in Law

Rate this story

My mother-in-law is sixty-three classy and very sexy with 34D breasts. She is also head of the HR department at her employer. She was divorced about a year after my marriage and her boyfriend passed about 5 years ago. We have always had good natured flirting between us, but as of late it has become more interesting. I was helping her redo the landscaping on her new house when I noticed every time she bent forward, her breasts were very exposed through the collar opening of her polo shirt. I just quietly enjoyed the view. When my wife and her...

Dear Diary

Rate this story

May 17th Today, Mom walked in on me while I was masturbating. That's the word she used. The guys at school call it whacking your wiener, but Mom says that's crude. Now that I'm eleven, Mom says I'm old enough to stay by myself after school. I usually get home about 3:30, and Mom's usually home from work by 4:00, so it's not that big of a deal, but today, school got out early, so I was home at 2:00. I didn't know she was getting off work early. When I know I'm going to have some privacy, I like...

Breakfast In Bed

Rate this story

One morning, I knew that my mother and father were both at work, and I could smell breakfast being cooked. I lay there in bed, toying with my morning hard-on, thinking of my grandmother. Grandma had big tits, that's all there was to it. At times, I had noticed that she wore no bra, and I could see the impression of her nipples on the blouse she was wearing. At 13 I noticed all female tits, especially my mom's and Grands. I got up and took a piss, then pulled off my undies and put on some shorts, just as...

READ MORE

Tags: big-breasts, grandma, grandmother, grandson, granny, huge-tits

Brighton Bed and Breakfast

Rate this story

I don't know if any of you have visited a seaside bed n breakfast in the UK before, but they're pretty grim affairs. I spent some time traveling around the south coast of England a few years back, so I saw a lot of them, spent a lot of time staying in them, and I know whereof I speak. Your typical English coastal B&B is a narrow three to five storey Victorian building within one or two blocks of the beach. They tend to be crammed together in rows, with no gaps between the buildings. Formerly houses for the rich,...

READ MORE

Tags: grandma, grandmother, grandson, granny, nightgown, older-woman

Caught by Aunt

Rate this story

Let me start off with the fantasy and I will bring it back in the story. It wasn't so much of a fantasy as a mental image I have held onto for many years. When I was about 8 years old I was staying with my grandmother and my aunt was also there. I was asleep on the couch in the living room when I was awoken by her walking through the kitchen to go do some laundry. When she was standing at the washer she had her pants unzipped because she was about the throw them in. The image...

Caught by Grandmom

Rate this story

I have been an avid reader of this site for many years. I like the stories about males being caught by female family members. Back when I was 18, I was home studying in my room. My grandmother who was 70 at the time had come over to visit and help around the house. Keeping clothes etc. Getting bored with my studies, I reached for a playboy. This was pre-internet days, and before I could go into a video store. A friend had given me the playboy. I opened it and and pulled down my jeans to my ankles taking...

READ MORE

Tags: grandma, grandmother, grandson, granny

Caught by Grandmother

Rate this story

I was about twelve or thirteen and I spent a lot of time at my grandparent's apartment. My mother and I had lived with them when I was a baby while my father was in the Army so I kind of became their favorite grandchild. I had become very curious about girdles (this was the early 60's) and had always seen my grandmothers on the chair in her bathroom. One night I finally got up the nerve to examine it and discovered the thrill of a lifetime. It had some stains in it and was very moist to my touch....

READ MORE

Tags: grandma, grandmother, grandson, granny, nightgown, spank, spanking

Becoming an Exhibitionist

5/5 - (1 vote)

The following began when I was 15 years old and continued until I was almost 18. My grandmother lived nearby and I frequently spent the night with her. I decided she was something of an exhibitionist and in a way trained me to be one too. She would put on a gown at night with nothing on underneath. I knew this because she would bend over my bed to adjust the covers and I could see all the way down the inside of her gown, her aged but ample breasts swaying in front of me. In the summer she would...

READ MORE

Tags: anal, anus, grandma, grandmother, grandson, granny, rectal, rectum, spank, spanking

Bathing with Grandma

Rate this story

I had just graduated from college three months ago. I moved in with my grandmother because she had an extra room and lived in the city. So I thought it would be convenient for job interviews. I got all my stuff moved in and was straightening up my room when she came in and asked me if I wanted to go swimming. I was shocked at how good she looked in her bikini. At 55, she was still attractive. She had short curly brown hair and her face didn't have any mark of wrinkles. Her breasts were large and pert,...

READ MORE

Tags: anal, anus, grandma, grandmother, grandson, granny, rectal, rectum

Aunty Sue

Rate this story

My name is Colin, I'm fourteen years old, I've always been tall for my age, my mother told me once that when I was born I was in three to six months old clothes even though I was only eight pounds when i was born. Now that I am fourteen I'm six foot tall, thirteen stone (182Lbs). Blond shoulder length hair, electric blue eyes and every muscle in my body was totally defined, stomach was a typical six-pack. I had been approached several times to be a model in Birmingham but I only had one plan for my future, Football!...

A Visit to Grandma’s

3/5 - (1 vote)

"Damn it mom I don't want to go!" I shouted through my bedroom door. "I don't care your father and I are going away and you are going to your grandmother's!" my mom yelled at me from downstairs. At this point I was extremely angry, slammed my door, and threw myself onto my bed. I went to my computer and went to a porn site, as I always do when I'm pissed. I started looking at MILF's and Mature porn. They were always my favorite categories. I took off my pants and started stroking myself. After a few minutes of...

Auntie Alice 3

Rate this story

We got Alice home sometime late Sunday, she was now moved into Gladys's house using the bedroom where I used to sleep. Everything went well, except moving her in a car was a real hassle. Her broken leg was in a full cast from her upper thigh to her ankle. Her badly broken right arm, was encased in plaster from her arm pit to her wrist. Her other arm, the cast went from below her elbow to her hand, her thumb was immobilized. She was in a lot of pain and on some pretty strong medication, she slept through the...

Auntie Pleasure

Rate this story

Well I was 15 years old at the time and my grandmother was 58. She had a younger sister who was only 50 and had an incredible body. I discovered this when she came over to my house for the weekend while my parents were gone. She had to come over because her house was being fumigated and she had to stay somewhere close by. The first day she was there she came to the door with a large suit case which I took up stairs. My parents had taken my sister with them so her room was open. There...

READ MORE

Tags: grandma, grandmother, grandson, granny

At What Age Do Boys Start Wearing Panties?

Rate this story

Unless your mother dresses you up in girls clothing at age 3, I would assume about age 11 or 12 years old for most boys . I was probably an exception. I wore my first pair of panties at age 5. I was staying at my grandmother's for the summer. One day, she left to go to a neighbor's house to borrow some flower and chat for a few minutes. At this time I saw my chance to go into her room and look in her undies drawer. Since I'd been think about wearing girls undies for the last several...

READ MORE

Tags: grandma, grandmother, grandson, granny

Aunt Betty Takes Me In

Rate this story

I was 20 years old and had just split up with my long time sweet-heart ofmy teenage years as something told us to move on to better and bigger thingsin life. Not a big deal and I was relieved as personality- wise she wasn't theone for me and we had enough sex to last a life time, or so I thought. It wasthe summer of 82 and you may remember it was a scorcher. Very little rain andexceptionally humid. A strange combination but it lent itself to the story I am about to tell you. I had enrolled in college...

Aunt Betty the Nudist

Rate this story

I was 20 years old and had just split up with my long time sweet-heart of my teenage years as something told us to move on to better and bigger things in life. Not a big deal and I was relieved as personality- wise she wasn't the one for me and we had enough sex to last a life time, or so I thought. It was the summer of 82 and you may remember it was a scorcher. Very little rain and exceptionally humid. A strange combination but it lent itself to the story I am about to tell...

A Three Step Ladder

Rate this story

She answered the door wearing her usual evening attire, an old worn cotton print bathrobe and slippers. Mrs. "B" was busy hanging drapes, and wasn't sure what time Danny, her son would be home. He had gone with his father to a friend's house for a game of cards and pizza. I had stopped by to see if Danny was ready to go. He and I had talked about shooting some hoops at the park and then cruising the local burger joints and hangouts tonight. "While you're here, would you mind giving me a hand with these drapes?" she asked. ...

A Love of Lingerie

Rate this story

Part 1 When I was young, I was playing at a friends house for the afternoon. It was the Summer in the late 1970's. My friend was playing outside. I was inside reading a comic on the sofa, when my friends Mum had a group of two or three others Mums come to the front door. They had been out shopping for lingerie. I think it was M+S as I remember the green and gold carrier bags. They drew the curtains and two of them began undressing. I watched them unbutton their blouses and unzip and slip off their skirts....

A Loving Grandmother

Rate this story

I was 18 when my Grandfather on my Mothers side passed away. They were not well off by any means, neither was my family. My dad went to help out after the funeral making arrangements to sell her trailer and car, Gramma wouldn't need them since she was now going to move in with us. We lived in a 3-bedroom house, Mom and Dad's room on the far side from my bedroom and my 2 sisters' in the middle. Well, I was concerned about the sleeping arrangements now, knowing math I did the numbers and I was odd man out...

A Boy Helps His Grandmother Install a New Hot Tub in Her Backyard

Rate this story

My grandfather died when I was teen, and my grandmother never remarried. I had always wondered why, and sometimes I wondered if she dated. She would come over, and I used to wonder what she looked like naked, if her body was still in good enough shape for a man to be interested. She wasn’t bad looking at all. She had dark, jet-black hair, and I figured the color came from a bottle. Hell, I didn’t care. A person of 59 has to do what they have to do in order to look good, I figured. She had good-sized tits,...

READ MORE

Tags: grandma, grandmother, grandson, granny