Vacation Cuckold Stories

28,460 results
Orientation
Length
Source
Infinite Scroll

My Sister's Boyfriend

by KinkyPotato on Sep 13, 2017
Transsexuals & Crossdressers

I never considered myself to be gay or anything like that, but my first time was with my sister's boyfriend. It happened a week ago now. I was at home alone, parents away on vacation, and my sister gone on business. These times were fairly common, so I would use them to indulge in a little habit I had. I liked to crossdress in my sister's clothes. Nothing se...

My Story Ch. 01

by Fluidity on Sep 13, 2017
BDSM

I arrive in NY, thankful to have a week’s vacation alone in a Manhattan hotel room alone. I am also excited to meet you who’ve I talked to for so many a night. I know you have a quite a night planned for me, and I can’t wait until it begins. I drop my bags off at home before heading out to get my first waxing... I want to make sure I'm completely bare and sm...

Co-eds on Vacation Ch. 03

by bigcanuck on Sep 15, 2017
Group Sex

Author's note: Although I am not allowing public comments, I do appreciate feedback, positive or negative... I just got sick of people who post anonymous comments about how a story violates their moral code. If you like it or have some advice on how to make it better, let me know. ********** "Are you ready for your turn?" Cam said to Katie. He and Aaron ha...

Vacation Getaway Ch. 04

by meraena on Sep 13, 2017
Group Sex

Meanwhile a few doors down, Papi was still involved in his orgy with the young eager sluts. He had already cum two times only to be brought back to hardness again by the mouths of his teenage whores, who were unwilling to let this thing come to closure until their appetites were sated. Papi knew he only had one more orgasm left and made the most of it by hav...

The Window Ch. 04

by catmanhunting on Sep 16, 2017
Novels and Novellas

Everyone is still over 18. * Jen woke in the morning and stretched lazily. As she rolled over she felt the dildo still inside her. Feeling full was wonderful, but she had some aches and knew that a trip to the bathroom was in order. After doing her business she grabbed a quick shower and went down for breakfast. Breakfast was light, her typical mix of frui...

A Trip To Remember Ch. 06

by staninalone on Sep 14, 2017
Erotic Couplings

Matt met me at the airport. I was surprised to see him standing with a bag slung over his shoulder. "Hi how are you?" I reached up and gave him a kiss. "Good, ready to go?" "Sure I can’t wait to get home." "Oh yea about that. We aren’t going home. I booked us a week on a little island called Aros. I rented a villa on the water with our own private beach...

D & J's First Time Bi

by oddessy2 on Sep 12, 2017
Group Sex

Here's the story about David and my first bisexual encounter. I've exaggerated some, but it's basically true. We were with couple named Rick and Jennifer. They had invited us over to Rick's parent's house who were gone on vacation. We had been camping with Rick and Jen a couple of times and had always found a secluded place to go skinny-dipping which David...

My Beautiful Wife Jennifer

by dannymike on Sep 12, 2017
Exhibitionist & Voyeur

My name is Michael. I have been married to my wife Jennifer, Jen, for about 10 years. Jen is 5"10", slender, red hair, green eyes, 36DD, with the longest legs you have ever seen. Men stare at her constantly which is fine with me. I am very proud of my beautiful wife and appreciate the attention she gets. Jennifer always seems oblivious to it, not really cons...

Meeting My First Gusher

by Shotgun59 on Sep 14, 2017
Fetish

It was nearing dark when I pulled out of the office parking lot. The commute to my condominium was only a twenty-minute drive from the heart of the city. I stopped off at a corner pub to have a few spirits to take the edge off the day. I stepped up to the bar and took a stool. I looked around familiarizing myself to my surroundings as my eyes adjusted to the...

Seducing the Virgin Ch. 02

by NoggintheNog on Sep 12, 2017
Celebrities & Fan Fiction

The Tuesday passed uneventfully. Two Jehovah's Witnesses came to the door. I opened it in the nude. I think that the younger woman was interested, but her friend quickly took her away. The girl came back during the evening, and we screwed around, I hope I haven't corrupted her too much. The following, day was Wednesday, and the virgin, Ben,that Phillip knew...