#alternateuniverse!wincest

[cherrycocoacola]

Professor! Dean x Student! Sam

Dean Winchester, an American History professor at Stanford, was a southern boy with enough charm to knock you on your feet.

That's what happened with Sam Singer, a student at Stanford. He sat working on his research paper, day dreaming of his teacher pounding into him on the big oak desk.

He snapped out of it when Dean called on him.

"Mr. Singer? Can you answer what party Benito Mussolini was?"

"Oh... Uh... The Republican Fascist Party. "

Dean looked at the small boy. Smart kid even though he swore Sam wasn't paying any attention.

"See me after class." Dean told him

Sam nodded, swallowing hard.

After class, Sam remained in his seat, packing away his things. He stood up and walked over to big oak desk.

"Were you paying attention to my lecture, Mr. Singer?"

"N-... No, sir.. " Sam answered honestly. "I did the paperwork though. "

"Interesting."

Dean stood in a pinstripe button down with dress pants and nice dress shoes. He knew how to dress.

"Just turn the paper in when the rest of the class does. I think I'm going to have to punish you for not paying attention though. "

Sam swallowed hard again. Now he was nervous. Would this go against him in a chance to go to Harvard? This was only a minor class... Can he do this..?

"What punishment, sir.? "

Before he could give any other thought, his professor had lifted him up and sat him on the oak desk. His face grew a heavy red.

"M-... Mr. Winchester... This... This is wrong.." He knows it was wrong, yet somehow he daydreamed this too often..

"I know, but... I can't stop looking at you, listening to your voice... I want you.. I need you."

Sam's face couldn't get any redder. He did relax in the older man's arms.

"You can have me...But please... Be gen-.. " Sam was cut off.

"You've never had your cherry popped, Sammy?" Dean asks.

"N-.. No.. " Sam shook his head.

"I want you to have a good, comfortable first time. Not this."

He thought Dean was sweet, hearing him say he should be have a comfortable first time.

"Would you like to come home with me?"

"I don't want you to get into trouble with your wife, sir.." Sam laughed sheepishly.

"I'm not married." Dean lifted his large hands to cup Sam's gentle face in his hands.

"Oh.. I'm sorry I didn't mean to assume.... I'll come home with you.. My roommate is home anyways.. "

With that, Sam went home with his professor.

*Le time skip*

Dean had just prepared Sam's virgin hole then pushed into him slowly.

Sam's moans were whines at first. It took time to get used to a cock as big as Dean's.

Two hours worth of skin hitting skin, choked moans, pants, and gasps as well as masculine groans pass by.

Sam lay under the covers of the bed and in the large muscled arms of his professor.

"This isn't right.. " Sam was hit by a huge ping of guilt

"It's okay, babyboy. It's gonna be okay."

"You're my professor... You could lose your job or worse... Go to jail... I'd get kicked out.. "

"Then I'll quit. I don't want to lose you."

Tears filled Sam's hazel eyes, shoulders shaking, lip quivering.

"Hey, baby what's the matter...?" Dean asked soothingly and sat up lifting the boy into his arms.

"I-I-I... I don't deserve this... " Sam sobbed.

"Shhh.. You deserve the world, Sammy."

Dean pet Sam's long, brown locks. He cradled him til he couldn't cry any longer.

"You deserve all the stars in the sky.. Whoever hurt you before... If they come across me... My fists are meeting their faces.. "

Sam laughed softly.

Dean did later quit the job and joined the police force. He wasn't loosing someone who's been hurt so many times. He wanted to care for Sam.

He supported Sam in the fact Sam loved skirts and dresses, makeup, and doing his hair. Dean always thought it was cute how good Sam was at makeup.

"My face is a canvas and I like to paint it with makeup. " Is Sam's signature catchphrase.

When he thought it was the right time, Officer Dean Winchester proposed to Samuel Singer.

Sam was extremely happy especially when they finally married a few months later.

Dean came home from a night of road violation tickets and checking card, when Sam walked.

Dean couldn't believe what he saw on the little stick you used to see if you were pregnant.

Fin.

Edit:

Parts two

Much time passed and Sam had had to twins. Two boys. Harper Leigh and Jeremiah Michael Winchester.

Sam was the most proud momma and wife to Dean Winchester.

One morning, Bobby Singer, Sam's father and the boys' grandpa, had arrived to their home in Kansas from South Carolina.

The boys ran over and hugged the trucker styled man. "Hey boys. Been good for your momma?"

They nod. "Yep!" Jeremiah smiled.

The boys weren't identical twins. Jeremiah looked so much like Sam and Harper looked so much like Dean. Though Harper was the shy one and Jeremiah was the eccentric one.

Bobby played with the boys and their blocks and action figures til they went for their naps. Sam talked with his dad up until his husband started a conversation on cars and Bobby talked as well. He let then have fun, glad they could get along.

Sam made both men coffee though it was noon. The conversation then went to Dean being an officer. "Does Sam stay home? "

"Yeah. I work customer service from home so I can stay with the boys."

Sam set up a room for his dad that night.

Dean and Sam fooled around, managing to stay quiet.

San rode Dean cock. With much experience, he stayed quiet, but Sam moaned.

Skin hit skin and he could feel droplets of sweat drip from his forehead and eyebrows.

"I've needed this, Dee.. " He panted.

"Fuck... Me too, Sammy. God, princess."

After hours more of intense teasing and Sam theoretically riding Dean, Sam came and felt Dean shoot into him.

Sam collapsed next to his husband and passed out from exertion.

It was amazing.

Many weeks later, Sam and Dean knew their routine. Sam loved taking care of his family.

It was one amazing family.

@say-yes-to-hole @libraryofdimpledbottoms

[cherrycocoacola]

AU! Edits I made

Gatsby! Dean x Daisy Buchanan! Sam

WW2 Soldier! Dean x 40's Reporter! Sam

[cherrycocoacola]

Ask meh.

Feel free to ask me for a wincest/weecest/alternateuniverse! wincest fic ideas.