First Time (San)
content warning: friends to lovers; softie sex; slow burn; handjob; fingering; virgins; aftercare
Masterlist
Minors DNI 🔞
word count: 4042
"Good morning" you yawned as your eyes fluttered open for the day. Behind you, San was cuddly and snoring lightly despite needing to wake up for class.
You turned to face him, which proved difficult because of how tight his hold was on you, but you finally ended up face-to-face after an exhorbant amount of effort.
"If you wake up now, I'll make pancakes while you're in the shower," you bargained as you traced the lines on his face.
San groaned because he couldn't resist the offer even if more sleep was what he really wanted. "With blueberries?" he asked, his voice deeper than usual since he'd just woken up.
"With blueberries," you agreed.
San's eyes flashed open, and he squeezed you tight with a hum before removing himself from the bed. You immediately missed his warmth but knew he had a presentation today. You didn't want to be the reason he missed it.
You crawled out of bed and shivered from the chill in the air. Your shorts and tank top combo was doing little to help, so you stole San's hoodie from his gaming chair before making your way to the kitchen.
Mornings like this had become routine. At the beginning of the year, you'd been randomly assigned a roommate by the college's welcoming committee, and she had a habit of bringing random guys to the dorm every night. You'd known San from high school and knew nobody else, so you'd asked to crash with him once...then twice...then a third time... Before you knew it, you’d gradually moved all of your things into his off-campus apartment.
He had no roommate or second bedroom, so you slept with him every night. Everyone at school thought you were dating, which neither of you minded. You weren't interested in anyone and neither was he.
"We're almost out of body wash," San told you when he walked into the kitchen with wet hair in his favorite jeans and plain black t-shirt look.
"Is there enough for me?" you fretted as you wrote it down on the magnetic shopping list on the fridge.
"Of course," he promised as he piled some of the pancakes onto a plate. "These look great, by the way."
You thanked him and took your seat at the table. Mornings were often quiet as San liked to read the news and you liked to read your fantasy books. He'd look up and smile now and then and even collected the dishes to clean once you were both done.
"I got asked to pick up a shift at the writing center tonight, so I won't be home until 7," you told him.
"I'll take care of dinner then," he said before kissing your cheek and shrugging on his backpack. "Have a good day."
He was out the door just as you reached the bedroom to change for your class in an hour. None of your clothes looked appealing, though, so you tugged on some leggings and walked out of the apartment in San's old hoodie.
————————————————————————————
"Do you think we're weird?" you suddenly asked. San was cuddled behind you with his arm pressed against your waist, and you were facing the dark void of the room. Nothing was out of the ordinary except a hushed conversation you'd overheard earlier.
"I swear they're not dating," someone had said.
"Then they're fucking a lot," another voice teased.
"Or they’re just like Dawson and Joey in that old 90s show," someone spoke up, trying to defend you from the others.
"And Dawson and Joey were weird, too. Would you share a bed every night with some guy you weren't dating?"
"How do you know they're sharing a bed?"
"Some of my friends lived in that building last year. They only have one bedrooms on that floor."
"Maybe they are dating," they mumbled back, sounding disappointed.
"Or maybe they're just weird," someone laughed again. This time the others joined in.
San shrugged. "I don't know. Does it matter?"
You sighed and moved closer to him. You always sought him out when you felt off center. "I guess not."
"You can tell people we're dating if you want," San offered. "It's not like I'm planning to ask anyone else out anytime soon."
"No," you frowned. "That's okay. I'll just try to ignore them." You didn't want to stop San from finding a girlfriend just because you'd taken over his apartment as your own.
"Okay. But if you ever need to...you can," he reminded you.
"Thanks Sannie," you answered with a yawn before letting your eyes fall shut.
————————————————————————————
You awoke to a moan.
It took a few seconds for you to realize it had come from you and that in his sleep, San's hand had ended up on your chest. You tried to move it down, but (like always) San thought you were trying to escape and pulled you closer. His hand pressed on your chest and another whine escaped, this one causing him to wake up.
"Did you just..." he trailed off.
"Your hand," you complained. "It's on my chest."
"Shit," he hissed before pulling away and throwing his arm over his eyes. "Sorry."
You knew what that meant and turned to see him breathing deeply as he tried to make the tent in his pants go down. You laid your head on his chest and listened patiently to his heart until he'd calmed down enough to stroke his hand up and down your back.
"I didn't mean to touch you there," he apologized again.
You could feel your cheeks blush pink at the reminder of how it felt. His firm touch and large hands, holding you close... "I think I liked it," you confessed.
That night, when he held you, you guided his hand to rest on your chest. You didn’t hold back your pleasured whimper when you felt his thumb shamelessly brush your nipple through the fabric.
Your hips squirmed from the new feeling building at your core and San kissed your neck before whispering a hushed, “Goodnight."
"Night Sannie," you breathed.
————————————————————————————
Two nights later, San climbed into bed without a shirt. This wasn't uncommon, but you found yourself curious how it would feel to be shirtless with him.
"San, you're a feminist right?" you checked even though you already knew the answer.
"Yeah," he laughed curiously. The question had come out of nowhere.
"So if I took my shirt off, that would just be equality right? It wouldn't mean anything, would it?"
San's eyes grew a little wide, and he swallowed in surprise before stuttering, "You can sleep however you want."
With that, you tore your shirt off and watched his eyes go straight to your breasts. He'd never seen them before and seemed fixed on them until you hurriedly turned to lie down, your face red. You’d never shown a man your chest before and hadn’t hadn't expected to find him looking at you like that...like he was dangerously close to ruining your friendship.
"Aren't you going to hold me?" you asked. He'd yet to lie down, and you were eager to feel his skin on yours.
"Always," he promised. He took his time trailing his touch from your hip to your chest to touch your breast lightly. You gasped in surprise, body craving more. “Sweet dreams,” he cooed as he pulled you in. His warmth enveloped you, and you breathed him in deeply before letting sleep take you.
————————————————————————————
He was hard when you woke up. His cock was probing your ass, and you were certain it had to do with you being half-naked.
"Sannie," you murmured as you turned around.
He grumbled and hugged you to his chest, squeezing your tits against his abs and your face to his heart.
"Sannie," you rasped again. "You're hard."
"Fuck," he groaned and laid on his back with his arm over his eyes like always. You laid on his chest as usual and waited for him to calm down. Several minutes later, though, he was still hard.
"Does it hurt?" you asked curiously. You'd never seen a dick...especially an erect one... but it didn't seem to be a pleasant experience.
"Not too bad," he answered.
You frowned when he spoke. You didn't know he was in pain whenever he got hard and forced himself to make it soft again. "Can I see?"
San chuckled and took his arm away. "Why?"
You shrugged. "I've never seen one before."
San took a deep breath and pulled his pants and boxers down to show you his cock. It clearly wasn't getting softer, and you found yourself wanting to help him.
"Can I touch it?"
"If you want," he permitted.
You poked it at first, watching it wobble back and forth. San seemed amused by your method of touching him, but when you wrapped your hand around his length, his laughter died down to breathless whimpers.
Your shocked gaze looked up to meet his. His lips were parted as he stared at you intently, his chest rapidly rising and falling.
You drove your hand up and watched as his head fell back with a moan. It was perhaps the prettiest sound you'd ever heard. You rode your hand up and down his length repeatedly, earning more pretty sounds that had you growing noticeably wet between your thighs. You realized the tip of his cock had a slit and found yourself wondering if he would like you to touch there too.
The next time you moved down his cock, you glided your thumb over his slit, and watched in shock as his dick twitched and shot his release straight into the air. You'd never seen something erupt like that before and found it amusing and even a little fun.
His cum fell onto your wrist and his stomach, and he apologized between gasps for not warning you. His eyes were pinched shut guiltily when you glanced at him, and you found yourself laughing uncontrollably at the sight of his mess.
San snapped his eyes open, looking a little hurt and vulnerable, but you crawled up his torso and kissed his cheek to calm him down. "I want to do that again,” you grinned.
He smiled and shook his head in disbelief before getting up to clean everything.
————————————————————————————
The next few mornings, you woke up San the same way. Sometimes, you even got him off at night. It was becoming one of your favorite things to watch him get turned on and to see the shock in his face when he came. His whimpers echoed in your ears when he left the apartment, and you found yourself distracted all day wishing you could be in bed with him.
"(Y/N)," someone called from behind you.
You turned to see one of the writing center fellows hurrying after you as if he’d been shouting your name for a while.
"Hey!" you grinned, trying to hide the thoughts you’d been having about San behind a polite smile. "Is everything okay? Did you need me to cover for you again?"
"No, umm, actually, I was wondering if you were free tomorrow night," he asked nervously as he fidgeted with the hem of his jacket. "There's a cool new restaurant opening up, and I was hoping to take you."
"Oh! Like to hang out or..."
"As a date," he interjected.
You'd never been asked out before and could feel your heart pounding and the bile rising in your throat. There was absolutely nothing wrong with the guy in front of you, but even being asked on a date was making you anxious. "I can't," you told him definitively, the words falling from your lips before you even thought them.
"Maybe another day then?" he suggested. "I'm free on Saturday, too."
"Because I have a boyfriend," you lied, finding that it felt natural coming out of your mouth.
"Oh! I thought you and San were just friends," he frowned. "My bad."
You felt sorry for how upset he looked, but your body was immediately at ease knowing nobody could claim you since you'd decided to announce yourself as San's. "It's okay. We don't really tell people unless they ask. Thanks for the offer though," you answered.
He headed off then, and you rushed to make it home. San was already in bed when you arrived but was sitting up with crossed arms as he waited for you.
"It's kinda early for bed," you teased him as you pulled your shirt off and climbed into the sheets.
"You know, you won't be able to sleep with me anymore once you get a boyfriend," he warned.
You spun around in surprise at his words. "Where did that coming from?"
"I heard you got asked out today by that guy you work with...the cute one. When is your date?"
His jaw was tense as he spoke and deep inside you were sure he was a little jealous for some reason.
"I turned him down," you answered with your hands settled against his chest. You could see the relief in his features...could feel it in the way his heartbeat slowed.
"You did?"
"I told him I had a boyfriend already. I hope that's okay. I know you gave me permission to say that a few days ago, but..."
San's lips pressed to yours before you even realized what was happening. It was as if he couldn't stop himself. You'd never kissed him before and pulled back in instinct to his guilt-stricken face.
"I shouldn't have done that," he realized.
You hated the way his words sounded on your ears. You didn't want him to apologize for kissing you...in fact, you wanted him to kiss you.
"I just wasn't ready," you breathed, still trying to catch up to the reality of it. "Try again."
San's entire face lit up, and he cupped your cheeks this time before gently brushing his thumbs over your flushed skin. He closed the gap slowly, giving you plenty of time to change your mind. You didn't...
When his lips met yours it was like everything snapped into place. You were San's and he was yours. His lips were only against yours for the smallest of moments, but just like his body heat in the morning, you missed them the second they were gone.
"I don't know what this means," you murmured as you cuddled against him.
"Me either," he sighed with a kiss to your temple.
You laughed a little before turning to lie the way you always did. "It's a little weird for us to kiss when we're not dating, isn't it?"
He shrugged and pressed his hand to your stomach before kissing your shoulder. "I'd rather be weird with you than normal with someone else " he hummed.
You could feel him growing harder against your backside, could feel his lips littering your skin with kisses.
"Do you want help with that?" you offered as you tried to snake your hand back to his cock.
"No," he answered. "Let me try to make you feel good tonight," he pleaded.
"Me? As in you want to..."
San's fingers danced along the waist of your shorts. The tingling feeling alone made you whine and ease into him.
"I want to make you feel as good as you've made me," he rasped as he dipped his hand into your panties.
Your heart thudded in your chest in anticipation, and the second you felt a hot finger drag through your slick, your thighs constricted around his hand.
He kissed the back of your neck and instructed, "Put this foot behind my thighs. It'll keep you open for me."
You listened even though it felt a little embarrassing, but that shame faded away when you felt his fingers slide through you again. You gasped and looped one arm behind his neck as the other squeezed your pillow. You couldn't understand how you'd gone this long without letting him try this.
"Fuck I should've done this days ago," San groaned as he dipped the first finger into you.
It was an entirely different feeling having him inside you...having him stretch you open and curl his finger to hit that spot inside of you that few men even knew existed.
"I thought you were a virgin," you teased breathlessly. He was entirely too good at this for someone so inexperienced.
"I am," he promised. "I just know you," he grinned against your neck before inserting a second finger and watching you writhe against him.
"Sannie," you cried out. There was an unfamiliar pressure building, and you didn't know how to stop it or control it.
"Fuck your throbbing around my fingers, baby. Deep breaths. Just relax," he guided just as he let his thumb circle your clit.
You couldn't stop the overwhelming sensation from spilling out. Your hips jerked forward and back from the euphoria coursing through you, and San stopped touching your clit to curl his fingers as you rode out your very first orgasm.
Your breaths were heavy and your body spent when he finally pulled his hand away and urged you to face him. "Are you okay?" he asked as he examined you.
You smiled sleepily and leaned into his chest. "Never better."
————————————————————————————
The next few days became a string of orgasms and heated make-out sessions. If you weren't getting San off, he was getting you off. You often fell asleep naked now and didn't feel weird about that at all. It felt natural being with him...as natural as breathing.
Just like every other morning, he was hard when you woke up. This time, though, his cock was dangerously close to slipping through your folds.
"Good morning," he breathed as his hand snaked down your torso to settle on your clit.
You gasped and rolled your hips back and forth, riding your cunt up the length of his cock as he worked to get you off.
"Fuck baby," San moaned. "That feels so good."
You knew sex was a natural next step in your strange relationship. You turned around just before cumming and kissed him, catching him by surprise.
He melted into it and laid you back against the bed as he settled between your legs. His cock sat against your thigh, and you became heated imagining it inside you.
"Sannie?" you asked, pulling back with lips swollen from all of the kisses you'd received this week.
"Yes?"
"Can we have sex?" you asked bluntly.
San looked taken aback, so you continued before he could turn you down. "I've just never done it before, and I don't think I'll meet anyone I love as much as you."
"You love me?" he asked in surprise, his eyes softening.
"Yeah?" you replied as if it were obvious. "Don't you love me?"
"Of course," he answered. "But like...you love me how?"
You shrugged. "I don't know. I like being around you. And I like our routine, and I miss you when you leave the bed. I can't imagine leaving you anytime soon."
San smiled stupidly as you spoke. "You love-love me?" he realized.
"I don't know..." you replied shyly. You'd never put much thought into it.
"Ten years from now, where do you want to be?" he asked. If he was questioning your plans, he must've already had some of his own.
"Right here," you confessed.
"Me too," he grinned as he kissed you deeply, his body heating yours up until you were more desperate for him than before. "So of course we can have sex," he finally conceded.
"I wonder if it will feel good too," you pondered as he set his tip against you.
"Everything else has," he reminded you. "I think our bodies knew we were made for each other before we did."
"When did you know?" you asked. He seemed to be less surprised by all of this than you were.
"That day you were asked out," he admitted shamelessly. "I didn't want anyone else to have you."
Your eyes lit up in amusement as you recalled finding him in bed with his arms crossed and a pout on his face. "I knew you were jealous."
"I think deep down I always loved you," he confessed, his voice soft. "It's always felt so easy."
You felt warm at his words and kissed him again. "Me too. So it only feels right to lose it to you.”
“I feel the same,” he hummed just as he pressed into you.
You clutched his shoulder tightly as he eased in, focused on the feeling of warmth in your core and the way your body pulsed around his. San’s jaw was slack, a breathy sigh leaving his lips as he watched you bloom beneath him with rosy cheeks and mindless glances.
“Sannie,” you whimpered once he was settled completely inside you.
“I know, baby,” he rasped, his forehead settled against yours. “I know.”
Before you could stop it, tears began to fall down your cheeks. You wiped them away with a confused laugh and looked up at San who seemed concerned.
“Are you okay?”
“I think so,” you answered. “Just feels…big.”
He smirked and thrust in and out, “Sorry about that.”
“Not that!” you gasped playfully. “I mean it is…But I meant this feels big. Us.”
“I think so too,” he smiled as he captured your lips with his, groaning with every insertion, hips rolling to hit that perfect part of you. Every noise from your lips was involuntary and honest, and San looked proud to have as much control over your pleasure as you did his.
When you felt closer, he began to twitch inside you. It would’ve been scary to let anyone else see you so thoughtless, but San was yours…
He fell apart just as you came, releases mixing inside you between gasps and whimpers and trembling hips. You held your face against his neck and kissed the skin until it was purple.
Eventually, the moans turned to breaths, exhaled heavily against sweat-coated skin.
San pulled back just a little to watch himself pull out of you. You whimpered again and felt shy when he bit his lip and met your tear-stained cheeks. “Come here,” he rasped as he pulled you into his chest and stroked his hand up and down your back.
You hadn’t realized how much you wanted this with him…this moment after the moment where everything was still.
“I’m sorry I cried,” you confessed as a few more tears fell. “I’ve just never felt like that before.”
San pulled you closer and you tilted your head to look up at his protective and possessive gaze. “You don’t have to apologize, baby. You were being vulnerable with someone for the very first time.”
“So were you…” you reminded him. “And you didn’t cry.”
San let out a breathy laugh and kissed your forehead. “And different bodies react differently. As long as you enjoyed it, that’s all that matters.”
You settled close, only for San to pull away a little. “You did enjoy it, right?”
You lit up and kissed him with as much passion as you could muster on such little energy. “Of course I did.”
“Good,” he sighed in relief. “Me too.”
“I know,” you laughed. “It’s dripping down my thighs.”
San chuckled and went to get off the bed, “Let me get you a towel.”
You frowned and tugged him back to you. “In a minute. I’m not ready for the moment to be over.”
He kissed your cheek and happily wrapped himself around you. His deep breaths were like a metronome in the silence. You eventually fell asleep and awoke to his gentle hands guiding a towel between your legs.
“Go back to bed, baby, I’ve got it,” he promised.
With a sleepy smile, you turned to lie on your normal side. “I love when you call me that,” you admitted in a dazed whisper.
“Then I promise to never stop,” he vowed quietly just as you drifted off again.
