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Just Keep Trying

Summary:

“How do I tell Mike it was bad, without hurting his feelings?” Will asked Jonathan very candidly one spring morning in 1987.

The pair were in their kitchen eating breakfast. Hopper made scrambled eggs before he left for the station and Jonathan microwaved some bacon.

Jonathan chuckled, taking a bite of eggs. “What do you mean, bad?”

Nervously, Will bit his lip. “Like, I thought sex with your soulmate was supposed to be mind blowing. And honestly, it didn’t even feel very good.”

OR

Their first time doesn't go as expected and Will goes to Jonathan for advice.

Notes:

CW: Adolescent sexuality, conversations about sex, no smut.

Mike and Will talk about sex. Nothing too graphic but if that's not your thing, feel free to skip.

(See the end of the work for more notes.)

Work Text:

“How do I tell Mike it was bad, without hurting his feelings?” Will asked Jonathan very candidly one spring morning in 1987.

The pair were in their kitchen eating breakfast. Hopper made scrambled eggs before he left for the station and Jonathan microwaved some bacon.

Jonathan chuckled, taking a bite of eggs. “What do you mean, bad?”

Nervously, Will bit his lip. “Like, I thought sex with your soulmate was supposed to be mind blowing. And honestly, it didn’t even feel very good.”

“Did he, you know, prep you?” Jonathan asked.

“Bold of you to assume he would be the one prepping me,” Will teased. “But, yes. That part was great. It wasn’t the first time we had done that, so he very much knew what he was doing.”

Jonathan smirked.

“Get your mind out of the gutter,” Will shoved his shoulder.

“We’re quite literally talking about your sex life,” Jonathan reminded him. “Sorry for assuming you wanted to enjoy it.”

Will rolled his eyes. “You’re not helping!”

“Fine,” Jonathan breathed. “What do you want me to do? Tell him his dick doesn’t work? Because, he’d start sobbing immediately and get flowers from every shop in town to try to win you back.”

Will shook his head. “No. You’re not going to tell him we had this conversation. I love him so much, and I never want to be with anyone else. But, if we never had sex again I wouldn’t think twice about it. Besides, his dick works just fine.”

“That bad?” Jonathan raised a brow.

Will just shrugged. “I mean, it seemed like it would be pretty straightforward.”

“Or gay forward,” Jonathan joked.

Will ignored him and continued. “Emotionally, everything was where it needed to be. I was obviously nervous, but I felt so loved and appreciated. But, when it came down to the physical parts… I mean you know he isn’t very athletic.”

“Maybe you should top,” Jonathan suggested. “We both know you have more stamina than him.”

“I don’t know if he wants to do that,” Will breathed. “We’ve never talked about it.”

“Would you want to?” Jonathan asked.

Will nodded. “I totally would. I would be with him however he wanted. I guess we just have a default mode. I don’t know.”

“Do you really never want to have sex again?” Jonathan looked at him.

Will took a deep breath. “Of course, I do. I just don’t want to waste my time if it’s gonna be bad.”

“Did Mike think it was bad?” Jonathan wanted to know.

“He didn’t say anything after,” Will said. “He cleaned himself up and went to sleep.”

Jonathan’s eyes widened. “You’re saying he didn’t smother you with attention afterwards?”

Will shook his head. “No. I had to big spoon so we could still cuddle.”

“It sounds to me like it was a mutually subpar experience,” Jonathan concluded. “He probably didn’t know how to bring it up, either. He wouldn’t give you breathing room unless there was something wrong. You both are inexperienced. You can’t just be amazing the first time out. It’s gonna take a few tries to learn what you both like.”

Will nodded. “I guess.”

“He loves you,” Jonathan reminded him. “It’s all going to work out, and you’ll be going at it like rabbits in no time.”

Will stood up with a disgusted look on his face. “Now, I’m leaving.”

The second Will got to the front door, he saw a very familiar head of black hair standing outside of it.

“What are you doing?” Will asked, opening the door.

“I wanted to talk to you,” Mike kissed his cheek.

“Funny,” he let him in and closed the door behind him. “I was just about to go talk to you.”

Will let Mike into his room and shut the door behind them. “I assume we’re going to talk about the same thing?”

“Last night?” Mike asked, taking a seat on Will’s bed.

Will nodded and joined his boyfriend. “I’m sorry.”

Mike shook his head, and reached out for Will’s hand. “Don’t be. It was our first time. It has to get better from there.”

“You want to try again?” Will couldn’t believe it.

Mike nodded. “Why wouldn’t I? You know I love you. And, in case you haven’t noticed, I’m very turned on by you.”

Will blushed. “Ditto.”

“I’m glad I’m not the only one who thought it was bad,” Mike breathed.

“Only parts of it were bad,” Will corrected. “The things we’ve done before were great.”

Mike had a silent moment of victory. “Glad to know I can at least satisfy some of your needs, baby.”

Will rolled his eyes and climbed into Mike’s lap. “I love you. You satisfy everything.”

“Not everything, everything,” Mike said.

“But, you can,” Will said. “I’m willing to keep trying until we both enjoy everything.”

Mike felt a jolt of electricity shoot through his body. “Yeah?”

Will nodded. “Maybe we should just vocalize things we both want.”

“I want you,” Mike said.

Will rolled his eyes. “I got that part. But, is there anything you want me to do or you want to do that we haven’t done?”

Mike shrugged. “I was thinking we’d get into the kinky stuff later.”

“You’re so annoying,” Will groaned. “You know what I’m asking.”

“Well, there’s lots of things we didn’t get to do,” Mike said. “Lots of things I wanted to say to you that I didn’t because I thought it would turn you off.”

Will’s eyes widened. “Nothing you could say would turn me off.”

Mike smirked. “What if I asked you to beg?”

“Then, I’d beg,” Will said, confidentally. “It’s not like I don’t want it. I’ve been silently begging since my first erection.”

Mike laughed. “What if I wanted to spank you?”

Will started to feel warm. “I think I’d be very okay with that.”

“Yeah?” Mike smiled. “What about edging?”

Will nodded. “I promise, as long as it’s not feet or piss or something disgusting then I’m okay with it. I’ll safeword if I need to and if you’re unsure about anything you can just ask me. Even though you’re topping, I’m still in control. It just doesn’t seem like it.”

Mike, in one swift motion, laid Will down on his back and hovered over him. “Then, I better get to work.”

Will laughed. “I’d like that.”

Notes:

If you made it this far, thank you for reading!! I'm a little nervous about this one because of how taboo sex is in this fandom, especially between these two. And while I'll never write smut on here, I'd like to think that these two are very sexually active and it is a small part of their relationship.

Let me know your thoughts!

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