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I’ll Be Awake And I’ll Be With You

Summary:

“I really don’t want to fuck this up. I… I’ve had a lot of experience. And I’m into some things that are a little too advanced for a virgin. The last thing I want to do is rush into sex with you and scare you, or God forbid, even hurt you.”

“W-well at this rate, I’m going to b-be a virgin until- until I-I’m eighty. I can’t learn if you w-won’t teach m-me.”

Notes:

I finally got around to finishing part 2 of this series. I was overwhelmed by how well received the first part was. This is the last part I had planned for this story, but if you have requests, I’d be glad to add more.

Please don’t take any sex advice from this fic. I’m sure it’s all sorts of problematic and truth be told, I’m divorced and even when I was married, the sex wasn’t good because he turned out to be gay. This is as fictional as it gets. Anyways, enjoy!

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

Work Text:

After several months of dating filled with cuddles, kisses, making out, and occasional over the clothes groping, Steve was beginning to feel sexually frustrated. Eddie is the first person (or guy) he’s done anything with besides kissing. But, for some reason, whenever things get a little heated, Eddie tended to be the one to back off and let things cool down. 

Steve doesn’t want to push. He loves his boyfriend (they’d said those magical three words after just a few months) and wants them both to enjoy their time together. He just doesn’t understand why Eddie won’t fuck him already. It seems apparent that their sexual chemistry is great and Steve thinks he’s made his position on the topic clear.

So, he makes a plan to ask Eddie about it. Steve decides he is going to cook them dinner tonight at his trailer and finally find out the reason. His mom is out of town dealing with family stuff and they’ll have the place to themselves. Steve even bought lube and condoms in case this conversation goes the way he hopes it will. He couldn’t look Joyce Byers in the eye at the pharmacy checkout, but it will be worth it if he succeeds.

Which leads to Eddie sitting on his kitchen counter while Steve stirs a pot of pasta. Steve had insisted Eddie could watch tv while he cooked (Eddie insisted that the view of Steve’s ass was enough entertainment for him).

“You’re so cute when you play housewife, sunshine,” Eddie croons from his perch next to the stove. Steve picks up a dish rag and twists it quickly, smacking it at the older boy.

“D-don’t distract the cook.” The timer on the oven goes off and Steve goes to remove garlic bread. He bends over to reach inside and instantly feels his boyfriend’s gaze on his backside. “Not if you v-value your life, Munson,” he threatens lightly.

“Me? Mess around near hot things? Never, my dear. I’m just… admiring the view.”

Steve mutters something that sounds suspiciously like “perverted asshole,” which pulls a boisterous laugh out of Eddie.

Steve finds himself with a dopey smile on his face as he finishes cooking and sets the table for two. Eddie and him sit next to each other at the small round table, so close they’re practically touching at all times. Steve would probably gag if he saw anyone else as sappy as they are.

Eddie begins to eat and Steve waits, gauging his boyfriend’s reaction to the food. “How is it?” Steve means for the question to be casual, but Eddie can see right through him.

“It’s great, love. Everything you make turns out great.” Steve smiles at him and squeezes his hand once before starting to eat.  “So… what’s the special occasion? It’s not either of our birthdays and our six month anniversary isn’t until next month.”

Steve feigns his innocence. “Oh- uh, n-nothing really. Just felt like- like cooking for you, I guess.” He thinks he pulls it off.

“Mhmmm. Yeah, alright. Then why are you so nervous, baby?” Shit. Eddie is looking directly at him with piercing eyes searching his own for deception.

“I-I’m n-not n-nervous.” Despite it usually being better around Eddie, Steve’s stutter gives him away when he’s anxious or lying.

He didn’t even realize Eddie had scooched his chair even closer to Steve’s until the older boy gently grabs his jaw with his ringed hand, forcing him to meet Eddie’s gaze. Steve barely stops himself from moaning at the feeling of the cold jewelry on his heated skin.

“What are you hiding, beautiful? You just wanted to make a meal because you love me? Sure, okay. But you’re practically fucking panting at me like a bitch in heat right now.”

That finally does it. Steve lets out a moan that fills the whole kitchen. “Please, d-daddy,” he whines, unsure what he’s asking for. And only slightly mortified by the name that slipped out.

Eddie’s eyes widen slightly before narrowing into a calculating look. “Christ, Stevie, you’re gonna be the death of me. Why don’t we finish our dinner and then we can... talk about whatever it is you’re trying to do tonight.”

Steve protests as Eddie lets go of him. “N-no. You keep- keep doing this to me. Don’t pacify me, Eds. I-I wanna d-do more with you. Stop treating me l-like I’m fragile.”

“To hell with dinner,” Eddie mutters, pulling them both up from the table and over to the couch. “Steve, are you… horny?”

The younger boy nods, his cheeks glowing pink at the admission. “Yes, Eddie. I w-want to have s-sex with you so bad. W-why won’t you fuck me? Do you n-not love me?”

Eddie’s eyes turn soft and he pulls his boyfriend onto his lap, making Steve straddle his waist. “Of course I do, gorgeous. But I really don’t want to fuck this up. I… I’ve had a lot of experience. And I’m into some things that are a little too advanced for a virgin. The last thing I want to do is rush into sex with you and scare you, or God forbid, even hurt you.”

“W-well at this rate, I’m going to b-be a virgin until- until I-I’m eighty. I can’t learn if you w-won’t teach m-me.” Steve’s eyes are earnest and he’s practically begging at this point. Eddie is having a hard time keeping his resolve.

“…Okay.”

“Okay…?” Steve clarifies.

“Yes, okay. We can have sex. But there will be rules to this, baby. My priority isn’t to get my dick wet, it’s to keep you safe. Understand?” Eddie gives him a serious look and Steve holds back any jokes he might want to make. He simply nods in agreement.

“And there’s rule number one. I need verbal confirmation when I ask you a question, Steve. Consent is key and I don’t play with gray area. Make sense?” Eddie makes sure to keep eye contact with Steve.

This conversation is shorting out his brain so much that Steve almost answers with another nod. “Yes, sir.”

Eddie lets out a low growl at that. “Good boy. Do you know what a safeword is, honey?”

“I d-don’t think so.” Steve feels like every bit the virgin he is when he answers his boyfriend.

“That’s okay, sweetheart. A safeword is something we use during sex to check-in with each other. We can use the stoplight system for now. Green means you’re good and we can keep going. Yellow means we pause and talk. Red means stop immediately.”

Steve thinks for a moment before responding. “Can I n-not just say ‘stop’ w-when I want to stop?”

Eddie kisses his forehead affectionately and Steve melts into the action. “Of course you can, darling. But sometimes your brain gets a little muddled during sex and safe words are a good communication tool, especially if we get a little rough… We’re not going to be doing anything crazy today, but it’s still good to know.”

That makes Steve feel a little bit better. He’s definitely open to trying things with Eddie, but right now he’s just worried about the basics.

“O-okay. So green is good, yellow is s-slow down and talk, r-red is stop?” Eddie looks proud of him, causing Steve to blush.

“You’re so smart, love. The last rule is more for afterwards… and you don’t get to fight me on this one. When we’re done, I get to take care of you. I know you like to mother everyone, but it’s my turn to spoil you.” His blush deepens, Steve can’t imagine needing someone to take care of him after sex, but if Eddie insists.

“W-well you just said there’s no p-point in arguing about it, so- so I guess you know m-my answer.” Steve receives a boop on the nose for his snark.

“Sassy little shit,” Eddie mutters under his breath fondly. “Alright, I think that’s it as far as ground rules. But if you have questions, please don’t hesitate to ask. I want your first time to be great, angel. I love you and I’m honored that you trust me enough to do this with you.”

“I-I love you, too, Eddie.” Eddie smiles wide before swooping in to kiss Steve deeply.

Steve’s arms quickly loop behind Eddie’s head, pulling him even closer. He lets out a soft moan when Eddie begins to lick at his lips. Steve concedes to him right away and Eddie’s tongue plunges into his mouth. He tastes like the few bites of dinner they got through before they got carried away. Steve would laugh if he wasn’t so turned on.

One of Eddie’s hands makes its way under the hem of Steve’s shirt, brushing across his soft belly to reach his nipple. He moans into Eddie’s mouth when the hand begins to gently pinch and pull at his skin. “God, your little tits are so cute, sweetie.”

Steve’s hips cant at the statement, unable to hide how much he likes Eddie’s words. “Oh, you like that baby? You like when daddy plays with your tits?” Steve lets out a shameful whine, pushing his dick against Eddie’s thigh to get some friction. “Words, princess.” He reminds him with a gentle tone that contrasts with the hard pinch he gives to Steve’s nipple before moving to the other one.

“O-ow! Yes, I like it d-daddy. Like when you touch m-my boobs.”

“Good girl.” Steve feels a single tear fall down his cheek, he’s never been this horny in his life and Eddie toying with him is almost too much. “Color, Steve?” Eddie’s hand pauses as he uses his free hand to wipe away the tear.

“Green. It’s just- just a lot, Eds.” Eddie nods sympathetically, removing his hand from under Steve’s shirt.

“Okay, babylove. Why don’t we take this to your bedroom before we ruin the couch and your mother kills us?” Steve begins trying to get up when he’s surprised by Eddie hoisting them both up, carrying Steve easily. He tucks his face into his boyfriend’s neck on the walk to the bedroom, unbelievably turned on by Eddie’s caveman show of strength.

He’s jolted back into the present when Eddie throws him in the middle of the bed on his back. “Shirt and pants off, doll.” Eddie orders him while he himself begins peeling his clothes off. Steve scrambles to sit up and obey the command. He has his shirt off and pants around his ankles when Eddie sits on the bed in only his boxers, helping Steve finish pulling his pants off and chucking them somewhere in the otherwise spotless bedroom.

Once he’s stripped down to only his tight black briefs, Steve feels a bit self conscious. He attempts to reposition himself to cover a bit of skin, but Eddie won’t have it. “Uh-uh cutie, lay down so daddy can see you.” He pushes Steve flat on his back so he’s laying against the pillows. And then he gives his boyfriend a salacious up-and-down, licking his lips. “Goddamn, you’re fucking beautiful.”

Before Steve can shirk away from the attention, Eddie starts kissing his neck. They start soft and progress quickly to wet and messy. Eventually, Eddie isn’t even pretending to kiss his neck, just nipping at the sensitive skin there. It pulls little whimpers out of Steve that Eddie eats up.

Eddie slowly trails the hand not holding him above Steve down his chest. He stops to tweak a sore nipple again as he gives a sharp nip to the boy’s neck. Steve gives a soft squeak of noise that makes Eddie’s dick jump in his boxers.

His hand continues down Steve’s stomach, stroking softly over the soft skin there to make Steve squirm a bit. When he starts to let his fingers dip teasingly under the edge of Steve’s underwear, the younger boy finally speaks up. “P-please, daddy. Need it so b-bad.”

Eddie hums, “What do you need, princess?” His hand drifts over Steve’s briefs to just barely brush over his groin. This causes Steve to thrust up, seeking more contact. “Be good, slut. If you want me to do something, you need to ask politely.”

“N-not a slut. I’m y-your g-g-good boy.” Steve whines sadly, Eddie notices his eyes are a little teary.

“Shhhhh, you’re not a slut, sweetheart,” Eddie corrects himself, not wanting to actually upset his boyfriend. “Always my good boy, yeah? But you need to tell me what you want like a good boy.” He continues stroking over Steve’s lower belly, not brushing against his cock again.

“I-I want you to- to touch m-me. Please,” Steve practically begs him. Eddie has half a mind to be mean and tell Steve he was already being touched, but he takes mercy on his innocent lover.

Eddie pulls away for a moment to tug Steve’s underwear off in one good pull. Steve’s legs land with his knees bent on either side of Eddie.

The older boy kisses Steve’s knee gently and begins moving his mouth sloppily upwards on his thigh. Steve shivers at the contact, his fists gripping the sheets below him tightly in anticipation. Eddie finally reaches his goal and licks a long stripe from the base of Steve’s dick to the head.

Steve lets out a high pitched whine that encourages Eddie to pull the head of his cock into his mouth. He begins to attempt to suck Steve’s brain out, causing the younger to try to thrust his hips up. Eddie simply places a firm hand on Steve’s hips to hold him down.

He pulls off for a moment to tell him, “Keep still, precious, or I stop. I’m not into choking on dick… You, however, are welcome to choke on my dick anytime.” Eddie smirks as he returns his attention to Steve’s sensitive prick.

Steve moans loudly, whether at the action or Eddie’s words, he’s not sure. Eddie hasn’t sucked anyone’s dick in a while, but he thinks it’s kind of like riding a bicycle. He takes Steve deeper into his throat, swallowing easily.

Eddie can see Steve’s knuckles white from clenching the sheets and he takes mercy on the younger. He gently pulls his boyfriend’s hand away from the bed and places it in his own hair. Steve takes the hint and threads his fingers into Eddie’s hair, not tugging, just holding on.

He slowly pulls off Steve’s dick, giving it a few more teasing licks before sitting up a bit to look at his boyfriend’s flushed face as Steve pants to catch his breath. “Doing okay, honey? What’s your color?”

Steve swallows hard. “Green. S-so fucking green.” Eddie smiles devilishly at him, pleased at the effect he has on his cute love.

“That’s what I like to hear… Hey, Steve?”

“Y-yeah?” Still panting a bit as he responds.

“You ever heard of rimming, sweetness?” He asks innocently.

Steve shakes his head before recalling Eddie’s rule. “No, I d-don’t think so.”

“Excellent. You trust me, yeah? And you remember how to stop me if you don’t like something?” Eddie confirms, eager to further unravel his virginal boyfriend.

“Y-yeah. I trust you. And I know m-my safewords.” As soon as Eddie gets an adequate response, he sits back and hauls Steve’s legs onto his shoulders, ducking his head between the younger’s legs.

Steve lets out a small, surprised breath of air. Eddie can practically hear his confusion and it encourages him to quickly spread Steve’s cheeks and dive in tongue-first.

“O-oh that’s- oh. Eddie, oh my- oh my God!” Steve squirms a bit at the sensation. It’s foreign and his brain is a bit disgusted by the idea, but it makes his toes curl.

Eddie finally pulls back to lick around Steve’s rim, encouraged by the breathless noises Steve is making. He has to press one of his hands onto his own dick for a moment to relieve some pressure. “Do you happen to have lube, angel?” Steve is surprised Eddie took this long to ask, but he had been a bit preoccupied thus far.

Steve can’t catch his breath enough to answer verbally, grabbing the bottle from where he stashed it under a nearby pillow and tossing it in Eddie’s direction. The older boy chuckles at his antics, finding Steve incredibly cute when he’s eager.

Eddie pulls his rings off and sets them on the bedside table before popping the lid of the lube open. He makes sure to thoroughly coat his fingers in the substance, not wanting to risk hurting Steve in any way.

“Have you fingered yourself before, pumpkin?” Eddie asks as he starts to rub the tip of his pointer finger around Steve’s tight pucker.

“N-not really.” Steve squeaks out, still trying to adjust to someone touching him in such an intimate place.

“Not really?” Eddie questions with a chuckle. “It’s kind of a ‘yes’ or ‘no’ question, darling.” He begins to press his finger forward, getting the tip in up to the first knuckle. Eddie wiggles it around a bit, attempting to loosen up the clenched boy beneath him.

“I-I tried to, once. B-but it didn’t f-feel good. Just felt weird.” Steve feels the finger in him advance a little more and he focuses on the feeling.

“Hmmm. Well, your hands are kind of small. You don’t have the big, long guitarist fingers that I have. They’re great for making music and making cute boys moan.” Eddie smiles to himself, getting his pointer all the way in Steve’s hole.

He thrusts his finger in and out of Steve a few times before sliding a second one in with little resistance. “Such a pretty little hole, baby. You should see the way you open for me, it’s gorgeous.” Eddie licks around Steve’s rim while he continues the push and pull of his fingers, starting to scissor them apart to stretch his boyfriend.

Another long, drawn out moan from Steve. “Eddie you can’t just s-say things like- like that. It’s n-nasty.” Steve doesn’t sound very convincing, but he covers his face with both of his hands, attempting to hide as much as he can in such a compromising position.

“Oh, babygirl, I know you’re not getting shy on me when I literally have my fingers in your cunt.” Eddie gets a whimper in response and he grins at his bullseye. He had a feeling Steve was into feminization, whether the poor boy even realized it or not.

Eddie’s fingers face almost no resistance, so he joins a third one into his boyfriend’s virginal ass with little issue. Steve tightens up for half a second before relaxing into the sensation again. Eddie knows when he finally finds what he was looking for because Steve bucks up into the feeling, another breathless moan wretched from his lips.

“That’s it, sweetie. Almost done getting you ready for my big cock. You’re practically cumming on my fingers, I can feel how excited you are for me. Your cute dick is dripping all over the place, princess.”

With every thrust of Eddie’s fingers, Steve lets out little gasping “huh” noises. The sound is enough to almost drive Eddie over the edge. He carefully removes his fingers, enjoying Steve’s whine at being left empty.

Eddie pulls back to take his boxers off finally, his hard dick slapping against his stomach. Steve’s eyes go wide as he takes in the sight. “Holy shit, you’re huge. Is that gonna f-fit?”

He smirks at Steve’s dramatics, although he thinks the younger is genuinely concerned. “One inch at a time, darling.” Eddie looks around for a second for something. “Condoms?”

Steve’s blush worsens. “I h-have some if you want… But I’m obviously clean if- if you are?”

Eddie wants to eat him up. “Yeah, babe. I got tested after we met. There’s been nobody since the minute I set my eyes on you.” Eddie begins to slick his cock with lube, being generous again with how much he uses.

Steve gives him a soft look and just says, “I love you, Eds.”

The older boy adjusts Steve’s legs onto his shoulders and leans down to pull Steve into a deep, distracting kiss. His free hand positions his dick at Steve’s entrance, rubbing around the pucker of the tight hole. “I love you so much, Stevie.”

Steve moans into the next kiss and Eddie takes it as his cue to start pushing forward. He gets little more than the head in before Steve starts tensing up. Eddie pauses his movement and begins kissing sweetly down Steve’s neck. “Relax, baby.”

A single tear slips down Steve’s cheek and he gasps out, “H-hurts, daddy.” Eddie’s heart breaks for his lover. It’s been a long time since he popped someone’s cherry and even longer since Eddie had gotten fucked by anyone, but Steve means more to him than anybody else in the world.

“I know, baby, I know. Take a deep breath for me?” Steve trusts Eddie enough to immediately comply, forcing himself to inhale deeply. “Okay, go ahead and let it out slowly.” When Steve exhales, Eddie pushes forward, getting almost fully seated before Steve is done with the breath.

He freezes to assess how Steve is doing. “Color?”

“Y-yellow. I just need a m-minute.” Steve whimpers.

Eddie kisses his forehead gently, attempting to convey his love for the younger boy. “Do you want me to pull out?”

Steve shakes his head before he can get words out. “N-no. Can you just t-touch me? W-wanna feel good.” Eddie immediately complies, snaking a hand between them to grip Steve’s flagging erection.

He still has lube on his hand, so it glides easily over the younger boy’s cock. Eddie doesn’t bother to tease him, Steve has earned some pleasure. He pumps Steve’s dick in his hand, his erection returning quickly. It only takes a minute to have him making noises of awe again. “Y-you can move, Eds. B-but keep touching me, p-please?”

Eddie obeys, beginning to slowly pull back a few inches before pressing in again. Steve is much more relaxed now as Eddie continues to move his hand on Steve’s dick.

After a few careful thrusts, he can start to pull back further before going balls-deep in the younger. He knows when he finds Steve’s prostate again because the boy thrusts his hips against Eddie’s grip, whining for more. Eddie angles himself to hit the spot everytime, quickly driving Steve crazy with pleasure.

Eddie can feel himself getting close to finishing, Steve’s tight hole squeezing him hard. He can tell Steve’s getting close too by the way he’s breathing heavily, eyes squeezed shut, arms wrapped around Eddie’s neck to keep him close.

“Babydoll? Where do you want me to…?” Eddie’s having a hard time getting words out and keeping a steady rhythm with his thrusts.

He loses his rhythm at Steve’s answer. “In-inside, daddy. Want you to f-fill up my pussy… ‘m s-so close.” Eddie thrusts become less smooth and more erratic as he attempts to make Steve cum.

It only takes a few more strokes for Steve to lose it. He lets out a loud scream of pleasure, his dick shooting all over Eddie’s hand, some of it spilling over onto his stomach. Eddie takes the soiled hand and licks it clean as he continues to fuck into Steve.

Steve whines a little in overstimulation as Eddie keeps going. Eddie has just enough brain left to ask Steve, “You okay, honey? I’m almost there.” Steve gives a shaky nod and Eddie doesn’t bother to correct him about answering nonverbally. The boy looks fucked out of his mind.

A few jerky thrusts later, Eddie spills deep inside of him. Eddie pulls Steve into a sloppy kiss, more spit than lip contact as he comes down from his high.

He waits a moment before carefully pulling out of Steve. The younger winces regardless of the gentle motion. Eddie’s dick twitches at the sight of his seed spilling out onto the sheets. “Fuck, that’s hot,” Eddie mutters.

Steve’s eyes are closed and he’s completely out of it, so Eddie gets up to find a washcloth and clean sheets. He returns to find Steve still blissed out.

Eddie gently starts to clean him, starting with the cum on his stomach and working his way down between his legs. Steve whines a bit at the feeling in such a sensitive area, but Eddie shushes him soothingly. “Gotta clean you up, pretty baby. Let me take care of you.”

Steve settles down enough for Eddie to finish cleaning him up. When he’s satisfied, Eddie slips clean boxers and his own discarded T-shirt onto Steve. Eddie sits him at the desk with a glass of water to drink so he can change the bedding. He makes quick work of the task and guides Steve back into the bed to lay on his side.

Eddie slips in behind him, wrapping his arms around the smaller boy in a tight hold and kissing his neck gently. “You back with me, sweetness?” Steve hums in response. “You did so good for me, angel. I love you so much, Stevie.”

“Love you too, Eddie.” Steve falls asleep with a pleased smile on his face. His plan was a success.

Notes:

I’ve been writing this since I published the first part, but I stalled out a bit when I started my new WIP fic “Your Biggest Fan.” Anyways, my mom ended up in the ER with COVID yesterday and now I’m keeping her company at home (from 10 feet away with a mask on), so I have plenty of time to write.

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