Prompt: I don't particularly care about the details, all I know is that I want Jess to a) find out about Sam's never-acted-upon feelings for his older brother, and b)surprise him by giving him an earful of "want your big brother to fuck you open"-style dirty talk while she fingers him
Notes: Fill for Supernatural Kink Community and Sam/ Jessica Moore of spnpairingbingo.
Disclaimer: Supernatural belongs to Eric Kripke and WB. This was just written for entertainment
Jess always knew that Sam didn't have a normal relationship with his family. He didn't have any contact with them and didn't talk about them at all. The only person he ever talked about from his past was Dean. And even that was not often. Jessica knew that Sam loved Dean. He never told her openly but the message was clear. Perhaps Sam never said anything to the other guy, perhaps Dean had reacted badly to his friend telling him he was sexually interested in him, perhaps they had a relationship that ended for some reason. Jess didn't know the answer but she knew that her boyfriend was still in love with this other guy. And a part of him always would.
At the same time she was absolutely secure in his love for her. Nobody was as steadfast in his love as Sam Winchester. He had more than enough for two people at the same time.
The revelation that Sam was bisexual gave her the idea to include a few of her toys in their sex life, faster than she would have brought it up otherwise.
For the way they acted it was surprising how repressed and vanilla a lot of guys were. She had had to stop relationships before because her boyfriends weren't willing to see beyond standard missionary position and while they enjoyed a blow job, were not willing to reciprocate.
Sam on the other hand was perfect. He trusted her not to hurt him, or at least not to hurt him in a way he wouldn't enjoy and was always willing to experiment with her. The first time she fingered him he exploded within seconds, he trusted her about the plug and the strap-on got noises out of him she never heard before. God, she really should tape that the next time for their personal collection...
She saw the dog-eared photo due to an accident. It fell out of one of Sams book, the picture side down. She picked it up and read the backside: Sam & Dean, April 2001.
Just a short time before Sam had left for Stanford. She didn't even think before she turned the picture around. She never expected this opportunity, a little info in Sams past.
Well, when it came to men her boyfriend had the same great taste as with women. Tall, but not as tall as Sam, classical good looks, an open smile and a nice body under the jeans and Henley. She put the photo back in the book. She would have to ask him somehow what happened with him and Dean, they had looked happy in that picture.
Sam would have never expected to find somebody he could love as much as Dean. When Brady introduced him to Jessica, Sam saw the nice and pure girl and fell in love – and her dirty, open minded and downright bossy nature and easy laugh kept him interested and on his toes. Yes, he had a type.
He was laid out on their bed, his hands in cuffs and his body stretched. Jess had played with his body, massaged him with warm spicy oil, his skin tingled all over. He felt one of Jessica's fingers playing with his anus, circling the rim. Her other hot little hand pinched his nipples just the way he liked, stopping most of his higher brain functions.
"Tell me of Dean," "What about my brother?"
Brother. Dean was his brother.
So many things Jess never understood about Sam suddenly made sense. She could lie to herself and think that Sams love for his brother was the normal love one had for a sibling, that she had for hers, but she knew better. Sam had deeply incestuous feelings for his brother. Given that fact she couldn't imagine that he ever told Dean about this; How would you even begin such a discussion?
She knew she should react differently, should either feel disgusted by him or even pity for the situation. You didn't chose who you fell in love with after all.
But no, this turned her on! The visual alone was an intriguing idea and while it was a fucked up situation and emotionally unhealthy it wasn't that bad: who would they have hurt? It wasn't as if they had been in danger of producing webbed-fingered off-spring!
Of course, she had no idea how Dean would have reacted had he known. But she loved Sam and wanted to show him that this didn't matter to her.
She curled her finger and his reaction was immediate. A second finger circled the rim and pushed the warm oil in.
"You like that, don't you? Me opening you up like that?" Sam arched his back deliciously, a soft groan rumbled in his chest.
"How would you like a real cock there, Sammy? Not my finger or some piece of plastic, real hard flesh." Her hands were both busy, doing everything to bring him off. "Can you picture it, your big brothers hard cock opening you up, taking you hard and fast, the way you like it? Dean doing with you whatever he wants and you having to take it?"
His mind went blank. He shuddered through his massive orgasm and his consciousness needed a few seconds to reboot. She couldn't really have said what he thought she said. Sam opened his eyes fearfully, sure to see her disgust. How could she have known about his perverted nature, had he somehow let it slip?
He only saw understanding and curiosity, nothing discouraging. How had he been so lucky to find such a perfect girlfriend? "You aren't, disgusted?"
A small smile and he was sure that it wasn't a problem for her. A part of him wanted to introduce Jess and his brother, to have the two most important people in his world at his side, safe and sound and happy with him.
But the world didn't work like that and he knew he would never be able to have that.