Older Guy Stories

179,968 results
Orientation
Length
Source
Infinite Scroll

One Time Ch. 01

by Rigid1 on Apr 3, 2018
Loving Wives

Debbie and I have been married almost 8 years and while we have talked about having children, we have not gotten serious about trying yet. Debbie is 31 years old and I am 36. She is very petite, dishwater blond hair. She works out regularly and maintains herself in great shape. She is just a little over 5'0" tall, and weighs in at a mere 96 lbs. She is well...

Possession Process

by Fayd1 on May 27, 2020
Fetish

Intro + Characters John - 18, an average high school boy, who you play as, Does not stand out particularly, It is September, John just got home from a day at school, he plops himself on the couch, feeling exhausted, his sister Becca walking down from her room wearing her pajamas "Go shower John, you smell like shit" she says with some obvious disgu...

Open in Reader

My First Time

by xtcnymphette on Sep 12, 2017
First Time

My defloration happened shortly after I had just turned 18. I had had many opportunities to have penetrative sex before but for some reason I had never gone 'all the way' as my parents generation might have said. I don't think it was because of my catholic upbringing. I am sure my mother's feminist determination to show her daughters what a clitoris was and...

21st Birthday Party

by funguy696969 on Sep 12, 2017
Loving Wives

This story is a real life event that happened to me a few years ago. My name is Dave and I was 23 at the time and my girlfriend was 21. Its something that stays with me always and my mind wanders back to that night very regularly. The night in question was the night of my girlfriends 21st birthday party. She had organised a party for friends and family in...

The Hidden Island

by flashgordon562006 on Jul 31, 2019
Fetish

This is a story as told to me by my friend Jeff. We both hope you enjoy it. ****** I was out one evening with a friend of mine, having a drink. We were, as usual, chatting about sex, discussing what sort of sexual things we liked. Both of us at around 35-40 years and unmarried and both bisexual, our imagination centered around both sexes. How we wound up...

A Much Older Man Comes on to Me

by KDLeon on Nov 26, 2018
First Time

I was 22 years old and working as a technician for a new car dealership located in a small town in PA. I had been working on cars since age 15 and working in car dealerships for a few years. I was engaged to a beautiful 18 year-old girl who was going to college. She lived at school and I was living with her parents. My fiancee's parents liked me and offered...

Eat the Seed Pt. 02

by Digger66 on Sep 25, 2017
Exhibitionist & Voyeur

Please read part 1 first. ***** The next day was sunny and hot. The four of us took a long mountain bike ride through the surrounding hills. Mountain biking does not lend itself to conversations thus we did not discuss what happened the night before. On the way back to the motel, we spotted a thrift store. Jill insisted we stop in. She convinced Emma to g...

My Cousin, My First Time, and More

by ChiLisa on Sep 1, 2017
First Time

We live just outside of Chicago - I have been married for 7 years and have a beautiful 4 year old daughter. My friends and I were talking about our "first time" over the weekend for some reason, and I always tell the story of my boyfriend and what it was like. What they don't know, and only my husband knows, was that I lost my virginity to my cousin. I was 1...

Junior Year Abroad Pt. 10

by JBEdwards on Apr 14, 2020
Mature

This is Part 10 of the Survivor Revival Challenge, organized by Tara Cox. This is the story of Jim & Marybeth, and eventually others, of course. You can expect daily installments. *************** Jerome has seen the pictures of Marybeth. He picks her up. **************** Finally! Marybeth was alone. She could relax. Marybeth had shared the taxi Eric...

Nude Beach Adventures

by rockhard231 on Jul 4, 2018
Exhibitionist & Voyeur

I just finished packing my bags and I was ready to go. I was a bit nervous, but excited at the same time. All I had to pack was a towel, sunscreen, and water. All I was wearing was a sundress and sunglasses. Today was the day I take my nudity public. I had enjoyed the feeling of being naked as far back as I remember. The softness of the bedsheets as I slept...