First Time Cuckold Stories

351,145 results
Orientation
Length
Source
Infinite Scroll

The Virgin Desires

by Sensitive_Man on Sep 13, 2017
First Time

As she waited, Denise felt anxious yet excited; when the knock finally came to her door, she felt both emotions rise. Brian stood on the other side. She had waited for this day for some time, and now she was faced with it. She couldn't tell which feeling was strongest in her—the excitement or the apprehension, but she felt ready, more ready than she had felt...

MTV Awards Pt. 02

by Phileas123 on Dec 10, 2019
Fetish

The suite is very large, I look around and the first thing I see is the room full of packages and full of people. Then I look better, and there are indeed a lot of packages, but the people are just two. Frizo, with his customary braided white hairs and a woman, forty years old, perhaps. "Hi Jeff, hi Trish. I was waiting for you. This is Anna, my associate,...

How Rob met Annie

by WhiskeyIsGood on Sep 13, 2017
Transsexuals & Crossdressers

Some of you will remember these two, from my series "Jay's Sex Club Adventures." If you have not read that series yet, then I recommend that you go and read it now, before checking this one out...that way you know a bit more about Rob and Annie, as well as the few other characters who appear throughout this story. If you've already read it, then I hope you e...

The Last Time is The Best Time

by mikerol69 on Sep 13, 2017
Erotic Couplings

It was nearly closing time. Hilary didn't even announce herself through the intercom as she easily could have, from the front office, where she held the fort, but knocked at the door, asking if she could come in. The firm was down to three, the two warring partners, and to one person who doubled as girl and boy Friday. Hilary was a bit "born yesterday", even...

My New Client

by SimonSays1 on Sep 13, 2017
Mature

I'd been looking forward to a quiet day in the office, with no meetings and a chance to catch up with the pile of papers that had been gathering dust on my desk over the previous few weeks. The first few weeks of the year are always busy, and this year was no exception. I had spent the last few weeks rushing from one meeting to another, travelling all over t...

Escort Serviced Ch. 01

by chatbug on Sep 16, 2017
BDSM

Hi. My name is Jordan, and this is my story. In a little over a year, I went from a lonely divorcee to a contented woman with a manservant. I had no idea it was possible to enjoy life like this. I guess I should start at the beginning. I'd been divorced for a few months. I was getting a little old for stripping, so I thought I'd try my luck as an escort. I...

Beth Makes Me a Man

by Bakeboss on Aug 18, 2017
First Time

It was the morning after my eighteenth birthday and I was still asleep when my older sister, Libby came bursting into my room to wake me up. "Come on Seth, wakey wakey, I want to hear what happened last night." I groaned and rolled over to look at my sis, "What happened was you abandoned you little brother at the pizza parlor and he had to hitch a ride wi...

The Championship Baseball Game

by BobDogwood on Sep 1, 2017
Exhibitionist & Voyeur

When we weren't in the swimming pool during the summer months, we were usually down at the community recreational center. It was pretty nice. Outside it had a lot of trees that we could loll under out of the heat and some assorted picnic tables. There were some swings, a sliding board, the obligatory basketball court, and, surprisingly, a well cared for base...

Regrets and Consequences

by mabsls on Nov 16, 2020
Loving Wives

My first foray into Loving Wives. Not a BTB, but definitely not a RAAC. I'm hoping it's maybe a more realistic view of a marriage. Not much sex, but again, probably a little more realistic. And yes, I should have submitted it a couple of weeks ago, but sometimes life does get in the way. ********** Friday, October 25, 2019 - the Hansen Realty Company Hallo...

Penny For Your Thoughts

by Web_Spinner on Sep 19, 2017
Romance

I was home on Christmas break after my first semester at college. It was good to see my parents again. I had missed them while I was away. It was my first day back and I was in the den talking to mom about college life. Dad was at work when I got home so I had a warm welcome from my mother. I had only been home an hour when we heard the phone ring and mom we...