Dean Winchester Stories

3,878 results
Orientation
Length
Source
Infinite Scroll

Together—You and Me

by rwsteward on Sep 12, 2017
Romance

Dean scanned the directory beside the elevator as he ran his finger ran down the listings. There it was on the fourth floor; family court, that's where he needed to be. The elevator doors opened, and he stepped in. Although Dean had never stepped foot into the county court building, it was exactly the way he had envisioned it. The ceramic floor had long ago...

Dean and the Tgirl

by M.MartineMatheson on Sep 16, 2017
Transsexuals & Crossdressers

"Hi, it's Kelly," the sexy transgendered girl cooed when Dean picked up his hotel room phone. "Just get in?" Dean asked. "How was the drive." "It was quick -- I made good time." "Bet your thirsty," Dean said. "Meet me in the lounge down there for a drink?" "Would love to," Kelly said. "I'll see ya in a few." Dean took a final look at himself in the mirr...

Bi-male Party Night

by motmanri on Sep 26, 2017
Group Sex

This is based on a true story but names and places have been changed. Everyone in the story is over the age of 21. Thanks I hope you like it. Please feel free to PM me or email me. –Motmanri. First a little information, Dean and Jennifer are a married couple who have a great sex life. They always experiment and hold nothing back. They are open with their fa...

Dean and the MILF

by SupervillainX on Sep 17, 2017
Mature

Dean was muttering to himself as peak-hour traffic crawled through town. The sky was bleak, and Dean knew he'd be caught in a storm before he got home. "At least I'm luckier than those suckers," he said under his breath as he drew slowly up to a bus-stop and halted. The first fat drops of rain hit his windshield and he thanked his lucky stars he didn't ha...

A Different Thing Entirely

by magmaman on Sep 18, 2017
Loving Wives

Dean and Kay finished first, he lay back against the pillows on the huge couch, sweat creating a sheen on his upper body. She lay there partially over his body, her eyes closed as her breathing slowly returned to normal. It had been fantastic, yet Dean never would have even dreamed that something like this could ever happen. He glanced through the doorway...

Born Into Darkness Ch. 04

by wingedangel324 on Sep 19, 2017
NonHuman

Note to My Readers: Sorry for the mistakes this chapter isn't edited, I just didn't want you guys to wait any longer. Other than that enjoy, vote and comment. Love you guys ♥ * Dean kept his eyes down as he walked back to his seat. Their waiter Tony placed down their meal and a bottle of wine, leaving without a word. Breathing in and out trying to contr...

A Night to Remember

by WomynUvYrDreemz on Dec 2, 2019
Group Sex

Hello, everyone. I decided to try something a little different with this story, sort of coming out of my comfort zone by switching perspective. This is a story more fantasy than truth (though there are some true elements still), so I thought that was appropriate. I hope you agree. It's also a bit longer than my usual offerings. Please let me know in the comm...

Crime & Punishment Ch. 01

by Lady Jayne on Sep 14, 2017
Erotic Couplings

It was a sultry Friday afternoon in August. Two couples were having a picnic lunch in a secluded section of the park. "Hey guys," Ashleigh said, "Shane and I are going for a walk." The tall brunette took the hand offered to her by her boyfriend, Shane. She stood up and looked down at her friends still sitting on the blanket. "Have fun," Samantha said smil...

Born Into Darkness Ch. 03

by wingedangel324 on Sep 19, 2017
NonHuman

Note to My Readers: Sorry for the mistakes this chapter isn't edited, I just didn't want you guys to wait any longer and it's longer!!! Other than that enjoy, vote and comment. Love you guys ♥ Chapter 3 "Of course Sonny I'll marry you." Sophie said as accepted the candy Ring Pop from the twelve year old boy. He broke his arm pretty badly needed surgery; h...

My Hot Girlfriend Pt. 01

by Simondove on May 1, 2018
Loving Wives

It was all set up nicely for my girlfriend Amy's birthday party. It was a lovely sunny day, warm with a nice breeze. The party was held at my parents large home with outdoor kitchen, which my Dad was in charge of on the day. Not too many people were invited, some of her friends, my parents and my buddy Dean. Her parents happened to be on a round the world cr...