Older Guy Stories

179,968 results
Orientation
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Infinite Scroll

Legal Research/Hot Sex - Who Knew?! Ch. 02

by Yourstohave on Sep 16, 2017
Novels and Novellas

She couldn't quite believe that she had landed the Paralegal Level I position. The paralegal program coordinator had encouraged her to apply for a job even though she still had two classes left to complete in the program. She applied at the coordinator's insistence, but never really thought the whole thing would go anywhere. When she received a call for th...

Busted

by Kozmic Kowboy on Dec 12, 2018
Non-Erotic

Authors note: After my first story was published, I got to thinking about what would happen if the woman I based the female character on read the story and recognized herself. That thought was the genesis for this story. Reading Old Folk's Boogie before this will make some of the references clear. ***** After what seemed like endless false starts and bouts...

Two Brothers and a Vibe

by SlutProblems on Oct 8, 2019
Group Sex

"Do you trust me?" Mason asked. We had been dating for almost a year and Ioved him with all of my heart. He held himself up above me as we made love, our naked bodies glistening with sweat. He was the hottest guy I had ever dated, his short, black hair slightly curling around his ears and his warm smile beaming at me. He was tall, dark, and handsome, just th...

What do You Want Me to Do? Ch. 04

by foxtrot99 on Oct 29, 2018
Anal

As time went by, and Jane came to accept my instructions without question - I stretched my imagination, and made her available in increasingly erotic situations. For some reason I enjoyed having her provide sex to old men - sometimes ugly and overweight, or Asian waiters - or lorry drivers in their cabs. She baulked occasionally at my choices, but, after...

Hot for Teacher

by j_bakergal on Mar 25, 2019
Erotic Couplings

I'd re-read my message dozens of times. Still I was shaking, and couldn't bring myself to hit SEND. "Thanks for coming to my party! Sorry we didn't get to chat more...now that I'm graduated, does that mean we can finally hang out? :-)" I needed to be flirty & suggestive, but not desperate or inappropriate. Basically, I needed to not sound like a high schoo...

Black Cuckold Academy

by Samuelx on Apr 9, 2019
Interracial Love

"Black cuckolding is definitely a growing trend," Twyla Jackson said to herself, after reading some truly freaky stories online. The six-foot-tall, curvaceous young Black woman got up from her chair and went to look out the window. The suburb of Kanata, Ontario, sprawled before her, and Twyla allowed herself a smile. Things are getting interesting, Twyla tho...

The First

by Alittlechaos on May 13, 2020
Loving Wives

So this event goes way back to when my ex wife Laura and I had only been dating for 5 months. I had had a number of open relationships in the past and I have always been up front with potential partners with my preference towards non-monogamy. This was something my ex wife Laura had been intrigued with, and we had discussed various scenarios she and I woul...

Elisa

by icarusthewriter on May 12, 2020
Romance

Elisa and I had been friends since we were both 11-years-old. She was your stereotypical Tomboy; played baseball, never wore dresses, got into fights with boys and so on. When she came out, it was no big shock to me, but there was a massive disappointment among the many guys that wanted to ask her out. Elisa and I remained friends all through middle school...

The Parking Lot Ch. 02

by LatexSolarBeef on Jul 13, 2020
Transgender & Crossdressers

I thought of Val when I went home and the next day. I felt bad that she had to express her sexuality by blowing horny young landscapers in the parking lot of a bar. The Jersey Shore is a beautiful place, but family-oriented and traditional. It's a summer resort area. Once you go over the bridge from the barrier island, it is small towns and becomes quite ru...

Caught in the Wheatfield

by BluDawg15 on Oct 5, 2020
Exhibitionist & Voyeur

All people in this story were 18 or older, some elements of the story are true, all names have been changed. It's Monday around 10:30 a.m. and I am bored. My wife Jane is at her Monday classes on campus, she won't be home until later in the afternoon. I work a Tuesday through Saturday schedule thus on Monday's I am off and alone most of the day. Being bo...