****Things start to take a turn here for the darker, so we'll have a lot of ups and downs from here on out. TW: for SA and violence.*****
A few weeks passed as they spent time together, going on dates and getting to know each other, while also exploring the sexual side of things. Jeremy took Jimmy on some official dates, like taking him out to eat at different restaurants, and going to the movies in Kent where there were comfortable seats that reclined and they always had good deals on tickets.
Jeremy didn't really try to show off with his wealth. He tended to pay for the dates, but it was usually because he was the one who suggested where they went, and he grabbed the bill before Jimmy had a chance to. Of course, when they went to the movies, he agreed to split it up between the ticket prices and concession, and Jeremy usually won when it came to taking the more expensive price.
Jeremy had also eventually shown Jimmy how to use the butt plugs, starting with the smallest one. He took his time with it, wanting to make sure it didn't hurt him at all. He started with his tongue, softening Jimmy's hole while also making Jimmy moan and writhe at the unexpected pleasure that brought. Using one of his own tubes of lube, Jeremy slowly worked in a finger, starting slowly to get him used to the sensation.
Once he could feel Jimmy loosen up, he added more lube and added a second finger, curling them along inside Jimmy until he ran across Jimmy's prostate. He was gratified by the deep groan Jimmy let out into the pillow he was laying his head on, and Jeremy could see that he was leaking precum everywhere.
It wasn't until he could comfortably work three fingers into Jimmy that he finally moved onto the plug. Any time it hurt, Jeremy would pull it out a little and swirl it around just before where it hurt until Jimmy relaxed and then moved forward, though every once in a while he would take it out completely to add more lube. When he came back with it, Jimmy could take it easier and finally the plug kind of got sucked into place.
It was a foreign feeling for Jimmy, but it wasn't unpleasant, and it was definitely eye opening, both into what sex was like with a guy and also the type of gentleness Jeremy could have in the bedroom. Despite the fact that they hadn't had penetrative sex yet completely, he could tell Jeremy was an amazing lover.
Jeremy watched him for a moment as he moved on the bed so he could sit down, and the look on Jimmy's face told him that he could feel the plug hitting places inside that he could easily beg Jeremy to pound eventually.
"That's gonna be distracting," Jimmy said through a moan.
Jeremy grinned at that and moved to nuzzle his face into Jimmy's neck where he kissed and licked at the skin there. "I sure hope so. Don't wear it constantly, but I would love to drive you crazy with it the day we decide to move forward with me fucking you."
Jimmy couldn't respond out loud other than to give a soft moan. Jeremy reached down to tap on the plug, sending vibrations through it, which only increased the volume of the moan Jimmy let out. Jeremy looked down to see just how hard his boyfriend was.
"I better do something about this," Jeremy purred into Jimmy's ear before moving down the bed so he could settle between Jimmy's legs. He was told just how turned on Jimmy was with the groan he let out as Jeremy took him in his mouth, licking up that wonderful precum he'd been leaking this entire time before really working Jimmy over to get that load out of him.
Thanks to the rimming, fingering, and now the plug, it didn't take long for Jeremy's mouth to push Jimmy over the edge into ecstasy. Jeremy moaned around Jimmy's pulsing cock as he felt both of Jimmy's hands gripping his hair tightly as his cum flooded Jeremy's mouth.
"How is that so good?" Jimmy asked.
"Because I'm good at it, and I read your signals," Jeremy replied with a smile and then moved up to curl his body up against Jimmy where they slowly and gently kissed each other for a while.
Sometimes the trio of friends would go and watch the football team practice when they didn't have classes or homework, which the coach allowed so long as they didn't disturb practice. Ethan and Jeremy were having fun making fun of Chloe for her interest in Wayne. She was standing by the railing, looking down at where he and Jimmy were giving directions as they ran drills and plays, looking wistfully at the man who had caught her attention.
"There are only two options here," Ethan said one day when they were sitting in the stands, vaguely working on homework together. "Otherwise the guy doesn't know she's alive and has no interest, or he's playing hard to get because he realizes the exact type of slut she is."
"Excuse you," Chloe complained. "There is nothing wrong with enjoying a good dick, alright? Ask Jeremy."
"Jeremy hasn't found a good dick until now," Ethan pointed out.
"Hey now," Jeremy grumbled. "It's not like I had a ton of great options. I can't speak to Wayne though. I don't understand the minds of straight men, and straight black men at that. That's what we have you for, Ethan."
"Five hundred bucks says he never gives her the time of day," Ethan said to Jeremy, making Chloe turn from where she had been standing just watching the guys play with a glare.
"A thousand says he snags her for a long term thing eventually," Jeremy replied.
"Excuse you both, my sex life is not one of your damn bets," she groaned.
"Deal," Ethan said, ignoring Chloe completely and shaking hands with Jeremy.
"I hate you both," she grumbled and looked back at the field. "We have class, Asshole. Jeremy, don't do anything I wouldn't do."
"That doesn't leave very much," Jeremy said with a grin, and she stuck her tongue out at him before walking down the stairs toward the pathway out.
"Go sportsball!" Ethan called to the team as they walked out, and Chloe shoved him.
Meanwhile, during a lull in practice, Jimmy spotted Wayne watching Chloe leave and offered a penny for his thoughts. "Just trying to figure your new friends out, Sparks." Wayne said.
"The cute chick likes you, you know," Jimmy suggested.
"I am aware. I'm just not sure if she's done playing the field. I've done a lot of whoring around in my day and I dunno. I kinda want to whore around with just one person for a bit. Y'know?" Wayne mused.
