
The thing is, Sam loved women. No, he did. They, like, fascinated him. He'd grown up with no close female relatives or real friends, save for Dean's skank'o'the months and they were just so... Soft and mysterious and they smelled good and their laughter made his knees weak. He liked that girls buried their heads in his shoulder during scary movies and complimented him on his dexterous hands with flushed cheeks and desperate moans. He liked talking with them and making them laugh almost as much as he enjoyed fucking them and making them moan his name. Sam adored all women, of all shapes and colors and sizes... it didn't matter. He loved them all. A lot.
It's a big part of who Sam was at Stanford, the campus flirt, the cute loner who was smart and funny and willing to help anyone out with their course work. He had girls falling all over him within weeks of showing up at school, baking him cookies, flirting, wanting to do his laundry, asking for help with this or that... Practically ripping his pants off the moment they got him alone.
Not like he'd minded. He'd spent years watching Dean flirt and kiss and... other things with girls and it wasn't like he was a virgin when he got to school but. He definitely wasn't experienced. But with each girl, he picked up something. Technique, ideas, confidence. Kinks he never thought he'd have, kinks he never thought he'd ever try let alone like.
But college was all about broadening your horizons.
See, ok, Sam loved Jess. Loved her, was gonna marry her, have babies with her, picket fence, the whole nine yards. He knows Dean knows this. But what Dean doesn't know is that Jess isn't the only girl Sam has ever loved.
So one night, when he and Dean have been on the road for what seems like forever and there is nothing to hunt, they buy some booze and hole up in the room to get drunk off their asses. They were laying on their own beds and Dean was flipping through the channels aimlessly, grunting with displeasure when he discerned there was nothing on. He frowned and turned the TV off, rolled his head on his pillow to look at Sam.
"'m bored, Sammy," he slurred, eyes glassy in the lamp light.
Sam giggled and covered his mouth. "Dude, you're drunk."
Dean flipped him off, then started to whine. "Amuse me, Sammy. I'm BORED."
Sam took another sip of beer and thought for a minute. "What do you want me to do about it?"
Dean sighed. "I need laid," he mumbled out of the blue. "I need a woman, man. With like, huge tits and fucking legs that go on for miles, ya know? Mouth like a Hoover would be nice, too"
Sam smirked at Dean's change of topic. "Or... the real flexible ones, can fucking bend them any way you want and they just love it," Sam breathed, caught up in a memory of his sophomore year and a spunky Southern girl with dark eyes and a sarcastic wit.
Dean turned to look at Sam. "Dude. You're willingly going to talk with me about sex? Quick. Check outside for the Four Horsemen!" Dean snickered at his own wit and Sam laughed a little, too.
"Shut up, man. Just because I don't talk about it constantly doesn't mean I'm not into it," Sam sat up straighter, setting his bottle of PBR down on the stand between the beds. "Actually, I think you'd be quite proud of me and my reputation at school."
Dean squinted at Sam. "Whaddaya mean?"
Sam snickered to himself. "I got around at school, man. The girls there? Fucking loved me. Within the first two weeks, I had fifteen phone numbers and at least ten offers to get my dick sucked. Girls fucking dug the whole sweet, sensitive loner guy." Sam closed his eyes, face wistful, and leaned his head back against the headboard. "Man, Dean, I had so much sex my first two years at school... Good sex, too. Damn, Stanford had some talented coeds."
Dean sat up, face incredulous, clearly disbelieving that his little brother had been a man whore at college. He leaned on his elbow and stared intently at Sam. "Gimme a ball park figure here, man. How many a month, average?"
Sam opened his eyes and smiled wickedly at Dean. "Depended on the month and what I had going on - exams, papers, whatever. On average, two or three a month, though." He winked at Dean. "I didn't count by quantity, Dean. It was all quality."
Dean laid back, chuckling. "That's my boy!" He said, raising his bottle and taking a sip.
Sam took another pull himself and closed his eyes. "My first semester, there was Ang. From Florida, was majoring in Communications. She had such a perverted sense of humor and, damn, what we got up to in bed. She had this thing for, like, whips and leather. Then there was Diana from Pennsylvania. Journalism major, working for the Chicago Tribune now. She was hilarious. Gave good head, too. Then Kate, from New York, History major - she was real fucking firecracker man." Sam opened an eye to look at Dean. "I mean that literally, too. Fucked me with a strap on a few times. Fucking hot."
Dean about choked on his beer. "A strap on??? Jesus, Sam!" Dean sputtered out.
Sam continued on, not acknowledging Dean's outburst, clearly caught up in memories. "Then there was Julie. Man, she had awesome tits. Nice legs, too. I think I was with her almost two months. She had this blow up doll, man. God, she was freaky." Sam sat up straighter suddenly as he remembered and turned to face Dean, smiling brightly. "Oh yeah! She got me into my first threesome! Fucking hot, dude."
That time, Dean did choke on his beer. "First threesome, Sam? Holy fuck," he muttered.
Sam just laughed and sat back, smile soft and eyes closed as he reminisced about some of his favorite women in silence, not wanting to freak Dean out any more than he already had.
About ten minutes later, he heard Dean clear his throat. He opened his eyes and looked at his brother. Dean was half smiling. "Was just thinking, Sammy... Maybe I should've gone to college, too."
Sam snorted out a laugh and tossed a pillow at Dean.