It was the fall of their 13th year when Kyle's "summer freckles" seemed to stop being summer freckles, Stan noticed in the locker room before their first P.E class of the semester how Kyle's chest and back still had a few freckles spread out across them, he didn't say anything and Kyle didn't seem to have noticed at all. When they had been playing video games in Stan's room Stan had noticed a few freckles behind Kyle's ear and a few on his neck, he still didn't mention it.

Kenny also had freckles during summer, just a few spread across his nose Stan noticed the summer of the year they turned 14 but for some reason Kyle's freckles were different there was even more of them after that summer and Stan was sure that Kyle must have noticed by now. Stan wasn't exactly sure why but Kyle's freckles seemed more interesting now than they had been when they were only "summer freckles" like Kenny's still were. Early fall that year when the school had a small camping trip arranged for the students and Stan had been unable to fall asleep he had turned to Kyle who was on his left, Stan had stared at his face for a moment before he thought that, maybe if he counted the freckles it could help him fall asleep. He had been forced to lean a little closer to his super best friend to see the freckles in the dark. Kyle only had 13 freckles on his face; Stan continued to count the ones who ran down his neck. The next morning Stan had woken up with his face pressed against Kyle's chest; he had quickly pulled away and turned away so he couldn't see Kyle anymore. Instead he had turned to Kenny who was already clearly awake and wiggled his eyebrows at him, Stan had slapped his shoulder.

In November after Stan turned 15 he had cried when he told Kyle that he was gay, Kyle had firmly told him that he didn't care and then proceed to pull him into a hug. With his forehead pressed against Kyle's neck Stan had noticed that on Kyle's collarbone there was a freckle that was formed like a heart. When Stan joined the football team in high school Kyle was there for every one of his practices and Kyle always had Stan's extra asthma inhaler with him where ever he went.

The summer after Kyle turned 16 had been the summer when he had most freckles, his entire face, chest, back and pretty much his entire body had been filled with them and the entire summer Cartman made fun of him saying something about how Kyle finally had turned fully ginger. Most of the freckles didn't disappear during fall and Stan found himself ridiculously happy that they didn't.
8 days before Stan's 16th birthday he noticed that Tweek and freckles too. Only a few over his temples and his cheeks but just like with Kenny it just wasn't the same. Kyle's freckles were different somehow.

When they were 17 Kyle caught Stan counting his freckles while they were watching a movie in Stan's basement with Kenny and Butters who both had fallen asleep at that point leaning heavily against each other. When Stan had told him that he actually was counting them Kyle had blushed and asked if he did that often, Stan had simply shrugged and said that he did sometimes at that he wasn't really keeping track of himself doing so. Kyle had given him a nod and then turned back to the TV still blushing.

On the first day of the year they turned 18 Stan woke up with the worst hangover and his face pressed to Kyle's shirtless chest, other than their shirts they were still fully clothed and Kenny later laughed and told them that Stan had spent the majority of the night talking about how much he loved Kyle's freckles. Stan had shoved him lightly and then refused to speak to him for a week which only lasted for about 3 hours.
On Kyle's 18th birthday they had shared their first kiss; neither of them seemed to have noticed at first, it had just been a quick peck good bye when Stan left. Stan didn't realize they had kissed until he was at home. They talked on the phone throughout the night about just about everything, when they said goodbye at 3 am they both said I love you without thinking twice and when Stan came to school that morning tired as hell, his stomach flipped when he saw Kyle smile at him and they shared a chaste kiss before running off to class. No one seemed to notice the development of their friendship, probably because the entire school already thought they were a couple.
The night after they graduated that year Stan kissed every freckle he could find on Kyle's body.

They went to different colleges after that but they made the long distance relationship thing seem so easy according to Wendy. When they saw each other the summer after their first year of college Stan felt like his heart was about to explode.
Stan asked Kyle to marry him the summer of the year they turned 21. Kyle had barely gotten the ring on his finger before Stan grabbed him and kissed him all over his freckled face. 20 seconds later Kenny had tackled them into the pool, laughing and telling them he expected to be the best man, jokingly of course, but he ended up best man anyway.