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t’s not that often that Gabriel got a mission in his head, something that he wanted to figure out.
Rarely is that thing also truly productive.
And this mission might collect the most useless data ever.
He was going to do some travelling in time and visit each Winchester male- Henry, John, Dean, Sam, and Adam- in order to see who had the largest cock, and whether being well-endowed as a family trait.
He’s not entirely sure of what brought this idea on. Maybe as a way to prevent horny!him from going back to toxic relationships. Maybe it was morbid curiosity. Maybe it was him trying to quell his size kink tendencies.
Or maybe it’s because he’s had to listen to every lover that a Winchester male has had since Henry was 16 call out for God to help them take a Winchester’s big dick, and he was starting to tire of it.
So, Gabriel decided to do his own research.
You know. For Science.
He carefully plotted when to visit each Winchester, at what age and point in their (sadly) short lives and figured out how to approach them, as well as decide on criteria for penile size. He ultimately decided on length, girth, if they were a grower or a show-er, and whether or not they were circumcised.
First up was Henry Winchester at the very handsome age of 20. Gabriel knew that this was during the time that Henry was experimenting, before he had decided to marry Millie. Too young to have been drafted into World War II, and Gabriel knew that he was soon going to find a deferment from Korea.
They shared a few drinks in a bar, laughing and talking before they went to a hotel room for a tryst.
Henry was a little longer than average length, but where he made up for it was in the girth. He was, as the youth would eventually say, ‘thicc’. Gabriel was quite impressed that he was starting out so strong for his experiment. And the uncircumcised cock seemed to increase the thickness and length of Henry’s cock. Or it felt like it, in any case.
And the stamina of Henry Winchester was one to die for. Even when he was going hard and fast, he didn’t give in to the overwhelming desire to just spill into his lover du noir, plus he was able to go all night- and they did. They left the next morning from the hotel to depart and went their separate ways with a kiss, never to cross paths again in any timeline, but perhaps another life.
Henry Winchester. Average length, but very girthy. Stamina through the roof. Uncircumcised. Grower. Excellent fuck.
Next up was a bright eyed, battle hardened John Winchester. With him having enlisted a week after his 17th birthday, John was 18 when Gabriel visited him and he was quickly rising through the ranks.
He caught John in one of his encampments on a night watch. A night that was calm, the calm before a storm. John was feeling lonely, in need of some sort of company, and Gabriel, a soldier from a different platoon (or so John thought) was more than willing to help. You know, just to relieve stress and tension.
John didn’t exactly inherit his father’s girth, but he more than made up for it in length. Gabriel wasn’t saying that John wasn’t thick, but he had to admit that it was like comparing a beer cheese filled brat to ring bologna. Thick, but could be thicker.
But damn, did John Winchester possess a long, circumcised cock.
Gabriel also learned very quickly that just because John didn’t inherit a thick cock from his father, it didn’t mean that the stamina wasn’t inherited, because it was.
Apparently, John’s idea of a ‘quickie’ wasn’t a few minutes. It was a few hours. Gabriel’s fairly certain that they could have gone on all night, but John did have an important job to do, and it wouldn’t do for Gabriel to accidentally get him killed, so once they finished, he left.
John Winchester. More than average length, just above average girth. Stamina through the roof. Circumcised. Show-er. Excellent fuck.
Two down, three to go.
It was difficult to pinpoint a time to visit the raging bisexual that was Dean Winchester. he seemed to have been at his sexual peak since he was sixteen. He chose a 26 year old Dean, one that was just about to fetch Sam from Stanford.
Much like he did with Dean’s grandfather, Gabriel met Dean at the local bar that he found him at. He challenged Dean to a game of pool, to which he allowed Dean to win (although a true pool match, with neither of them holding back, would definitely give them a match to remember) and after that, Dean invited Gabriel back to his hotel room.
It was as if with each Winchester male being born, the cocks were getting bigger. Dean’s cock was the most formidable one yet. It was long like John’s, falling about an inch or so short of his father’s, but it was thick like Henry’s was. Maybe thicker, if Gabriel was being honest. He was circumcised, but he took delight in Gabriel’s uncircumcised one. Dean filled him up better than John or Henry, and the patent Winchester stamina held true for Dean.
Dean was also the first Winchester who had decided to also bottom for him, and Gabriel wasn’t a small man himself- in fact, his own cock was one that men would sell their souls to have.
Dean also was the first one to give him a souvenir from their time together: a pair of soft pink silk panties with a white lace bow on the front.
Dean Winchester. More than average length and girth. High stamina. Top and bottom. Circumcised. Souvenir acquired. Excellent fuck.
Gabriel would never admit this, but Sam was the Winchester that he was the most eager to fuck. Did the human moose- a humoose, if you will- have the cock of a moose? It didn’t help his case that he was mostly attracted to Sam out of all of the Winchesters (although all of the Winchester men were extremely attractive).
He met Sam in Stanford’s library, when Sam was 20. On a rebound from his break up with Brady, before he had the courage to start dating Jess. He passed himself off as a world religions major and managed to persuade Sam to go back to Sam’s dorm room for a different kind of study date.
Sam Winchester was hung. Like a horse (and Gabriel would know that information). He had quite a bit of Henry’s girth, but the length was even more impressive than John’s. The second uncircumcised Winchester kept up the patent stamina of his family, and Gabriel soon discovered that Sam was the kinkiest Winchester of them all. He supposed that that having a couple of different demon lovers (even unknowingly) and combining that with the demon blood in his veins would do that to a man.
When he left Sam’s dorm room the next afternoon, he was definitely limping and he made sure that Brady saw him, like the proud hedonistic archangel/trickster he was.
Sam Winchester. Above average girth, way above average length. Excessive amounts of stamina. Uncircumcised. Gold fucking star fuck.
Only one more Winchester left, and his research was complete.
Adam Milligan was going to be arguably the hardest Winchester to obtain. While Henry and John weren’t the members of the LGBTQ community that Dean (bi) and Sam (pan) were, they both had understood the need for experimenting and using sex as a release and nothing more.
Adam was the more close-minded of the bunch, and so to test Adam, Gabriel used his Grace to turn into a woman. Not that he minded that- it had been a moment since he experienced sex as a woman, but it was not the way he would’ve preferred to test him.
Adam was 19, a year before the Apocalypse started, six months before he started dating his girlfriend, and four months before he was attacked by the ghouls. He acted as a nursing major that had just transferred to his college and coyly allowed Adam into his dorm room for a ‘study date’.
Like his paternal grandfather, Adam had a short but fat cock that stretched Gabriel open and made his toes curl. The stamina was there, but certainly lower than his relatives. Gabriel was able to chalk that up to inexperience, as Adam didn’t have the time that his family had. Nevertheless, he did his best to keep up with Gabriel. And, he did fulfill morning sex before Gabriel left.
Adam Milligan. Average length, above average girth. High stamina. Circumcised. Had to be a woman in order to sleep with him. Very good fuck.
And now, it was time to compare results. His initial reports didn’t have sizes, but he had to change that.
Henry. 6 inches. Girthy. Uncircumcised. Grower. Stamina was a nine out of ten. Not particularly long enough. Would fuck again. Overall: 37/50
John. 9 inches. Average girth. Circumcised. Show-er. Stamina was a nine out of ten. Needed more girth. Would fuck again. Overall: 39/50
Dean. 8 inches. Girthy. Circumcised. Grower. Stamina was a nine out of ten. Perfect size. Excellent bottom. Would definitely fuck again. Overall: 41/50.
Sam: 9 inches. Girthy as fuck. Uncircumcised. Grower. Stamina was a ten out of ten. Kinky. Would absolutely love to fuck again. Overall: 47/50
Adam. 7 inches. Girthy. Circumcised. Grower. Stamina was an eight out of ten. Inexperienced; had to fuck him as a woman. Would fuck again to teach him some things. Overall: 35/50.
Looking over his notes, Gabriel smiled to himself.
He had his winner. Sam.
And then Sam and Dean found his notes (not the Official Scientific Ones, thankfully).
“Did you sleep with our entire family?” was Sam’s logical question.
Dean’s was “Are you telling me that I ended up having my grandfather’s and father’s sloppy seconds?”
“Yes, Sam, and Dean, it should be known that you’re the only one who bottomed for me and gave me a souvenir,” Gabriel smirked. “This was all done in the name of science.”
“And all I’m seeing is vague descriptions of my family’s cocks,” Dean said, brandishing the paper that Gabriel had used to take his brief notes on.
“Yep,” Gabriel hummed, popping the p. “I was seeing who possessed the biggest cock in your family. I gotta say, I’m not disappointed, not in the least bit.”
“What, do you have a size kink or something?” Sam asked.
“I do,” Gabriel admitted without shame. “I mean, I know that it also depends on the motion of the ocean, but hey, I gotta say. I like big dicks and I cannot lie.”
Dean nodded in agreement, flushing brightly as Sam looked at him. “What?” he asked. “The sensation of being full is amazing. I’m surprised you don’t agree with that, with the stick up your ass and all.”
Gabriel snorted.
“I’m a top, Dean, I don’t take it, I give it,” Sam said bluntly and without shame.
“Controlling bastard,” Dean said with a grin. “Hey, at least you know what you like.”
“I do,” Sam agreed, rolling his eyes affectionately. “Jerk.”
“Bitch. Anyways,” Dean turned to look at Gabriel. “So?”
“So what?” Gabriel asked innocently.
“Which Winchester has the biggest cock?” Dean asked.
Sam’s eyes burned with curiosity, and Gabriel smiled a Trickster smile.
He couldn’t help but fuck with them.
“Mary.”