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You and Dewey have been friends since high school.
Even though you could go weeks, or sometimes even months without talking or seeing each other in person, once you finally did, both of you slipped back into that easy and relaxed friendship, and suddenly it felt like almost no time had passed since you last spoke. Neither of you purposefully lose touch, it’s just the natural result of being adults living in New York City. You have your career, and… Dewey is doing whatever he does all day.
You’re at Dewey and Ned’s apartment, having a night in, watching a movie on the couch and enjoying a few drinks. Ned is out with a new girlfriend, you can’t remember her name, but Dewey had mentioned in passing that his friend had seemed pretty serious about this one.
The movie hasn’t really captured your interest, so once you notice you’ve finished your drink, you move aside the covers and stand, before turning so you’re facing Dewey, asking, “Hey, you want another, too?”
He isn’t too engaged in the movie either, apparently, because his gaze immediately finds yours, and despite having an entire half of his current bottle to go, he responds with an enthusiastic, “Hell yeah!”
You retrieve a couple of bottles from the refrigerator, but once you return, you notice Dewey is suddenly watching the movie with rapt attention. You’re getting comfortable, wrapping the blankets around you again, once you finally realize why.
The actors on screen are having sex.
You give Dewey a side glance, and he seems just as enthralled as before, even as you give him the beer, he barely even seems to notice. You raise an eyebrow, and say, “Come on, Dewey, this can’t really be getting you hot and bothered, can it?”
That seemed to break him from his trance, and he looked at you, visibly flustered.
“I mean really,” you continued, “how long has it been, for you to be having a reaction like that?” Dewey looked even more embarrassed, and you were enjoying his reaction immensely, until he bit his lip and mumbled something you couldn’t quite hear.
You gave an exaggerated “Hm…?” Before grinning and saying, “I didn’t catch that, Dewey.”
He glanced at you tentatively, and quietly admitted, “Um, never.”
Your smirk fell immediately, and you stared at him in shock. You couldn’t help but ask, “Really?”
Dewey nodded, and you felt a bit guilty now. “Sorry…” you started. “I didn't realize… I wouldn’t have teased you like that had I been aware.”
He shrugged, and his face twisted a little painfully, but he eventually said, “It’s… fine.”
There were several moments of silence after that. You could hear the movie still playing in the background, although it was obvious neither of you were focused on watching it.
You broke the silence first, asking simply, “Why?”
Dewey gave you a side glance, and shrugged again, before replying, “Are you really that surprised? Look… I’m only going to admit this once. I might be stupid, but I’m not an idiot, and I’m capable of introspection, on some occasions. I’m well aware I’m a… bit of a loser.”
You bit your lip. Dewey had to be feeling pretty emotionally vulnerable to be admitting that. He usually just projected, and while you had observed that he probably didn’t have as grandiose a sense of self as he often pretended, you certainly hadn’t expected him to ever come out and say it.
“Listen, Dewey… don’t think you’re a loser.” You murmured softly in protest, but he just gave you a pointed look. “Fine.” you amended. “You should probably give Ned some money for rent, at the very least. This is New York City, Dew, and it ain’t cheap!”
“Yeah…” he said, looking a bit guilty himself now. “That’s probably true.” You nodded, and repeated, “You aren’t even close to being a loser, okay?” You looked him directly in the eyes for several moments to emphasize your point.
Eventually, Dewey nodded, and you tried reassuring him, saying, “Hey, I’m sure that was difficult to admit. Do you want a hug?” Dewey tensed, and replied, “Er… That probably isn’t the best idea right now…”
You were confused, until you looked at his crotch and realized there was a bulge starting to form. Dewey had sweatpants on, which didn’t help conceal his indecency either.
“Oh!” You gasped in surprise. You looked back at his face, and he appeared completely humiliated. “I’m sorry… it’s just, you were being so nice to me, and -” he apparently was too embarrassed to finish that particular thought, and instead he finished, “I’ll just… go. I’m sorry for making things awkward.”
“What? Dewey, this is your apartment, where exactly would you go, even?” You asked.
He shrugged. As you both sat on the couch, staring at each other, you thought for several moments.
You hadn’t ever thought of Dewey like that before. Although you did find him attractive, he’d always been strictly your friend, but the more you thought about it, the more you realized you weren’t opposed.
Before you could even think about it, you blurted, “Let’s have sex.”
Dewey gave you an incredulous look, and said, “What?”
“You can trust me, Dewey. I’ll make it good for you.”
He blushed fiercely, but sobered before saying, “Are you really okay with this? You don’t have to… do it because you feel… obligated to, or something. It sucks being a 29 year old virgin, but still…!”
You nodded and said, “Dewey, I haven’t really ever thought of you sexually before tonight, but I’m completely okay with this, really.”
He didn’t respond verbally, but instead closed his eyes and leaned forward. You did the same, and then your lips were chastely pressed together.
Dewey’s lips were incredibly soft, and you relished the feeling, before giving his bottom lip a gentle lick. He got the hint and opened his mouth, and you began to kiss him more passionately, enjoying the lewd noises your make out produced.
Eventually, you broke the kiss to catch your breath. As your faces were pressed close together and you were both staring at each other, panting, you asked, “You have kissed before, right, Dewey?”
He scowled, and said, “Come on, my amazing skills didn’t convince you? I’ll have to show you again.” Dewey leaned in, and you waited for him, but he breathed onto your lips and murmured, “Of course I have,” sounding a bit indignant, before finally kissing you again.
After several moments, Dewey broke the kiss, and tentatively asked, “Can I…”
You noticed Dewey’s hand twitch, and you could guess what he wanted, so you grabbed his wrist, and guided his trembling hand to your chest.
Dewey’s hand rested on your bosom for several moments before you leaned in to initiate another kiss. Once you were making out again, Dewey apparently felt confident enough to start groping your chest, albeit gently. You moaned into his mouth at his touch, and this seemed to spur him on, because he brought his other hand to your breasts as well, and gave them a firm squeeze. Oh, you liked that, so much so that you leaned back and tossed your shirt over your head. You fumbled with your bra for a couple seconds before it finally unclasped, and let it drop onto the living room floor.
Dewey was staring at your chest, mesmerized. You leaned in again, but instead of going for his lips, you instead opted to lick and suck at his neck. You made sure your bare chest brushed against his clothed one, just so you could tease him a little. Dewey had a hoodie and graphic tee on, and you began to remove his layers. He seemed to be eager to remove his clothes too, and he shrugged off his red hoodie before disposing of his shirt.
You returned to your ministrations on his neck, and brought your chests together. He moaned, but whether it was at the feeling of your bare chest against his or the hickies you were leaving on his neck that caused his reaction, you weren’t entirely sure. Dewey began to move his large hands all over your chest and torso, fondling everything in his reach. You liked how firm his fingertips were, probably from all those years of being a musician.
As you glanced towards his crotch again, you observed how the bulge you’d noticed earlier had become a lot more prominent, straining against his sweatpants. You imagined Dewey had to be painfully hard by this point, and you decided it was time you did something about it.
You crawled onto his lap, and nudged him gently. He seemed confused, so you whispered sensually, “Lie back.” Dewey obliged immediately, and he was looking at you in anticipation, desperate to figure out what you’d do next. You tugged at his sweatpants, and he readjusted so you could remove them. Finally, you had Dewey in just his briefs, and you realized there was a wet spot on the front of them. You looked at Dewey and smirked, before reaching under the waistband and releasing his cock.
Dewey was a bit larger than average, but the girth of his member was also incredible. You almost couldn’t believe he was a virgin, girls would be falling all over him if they were aware of the monster between his legs. You wanted Dewey to be aware of how spectacular you thought his cock was, so you gripped the base, leaned in and gave it a few licks, before kissing the very tip of his dick, which had precum leaking from it, and saying, “Dewey, your cock is amazing.”
He gave you an incredulous look, and didn’t seem convinced. “Why are you talking like you’re in a shitty porno?” He asked, before scrunching his face and saying, “You don’t have to lie on my account just because it’s my first time, or whatever.”
You moved back to give him a sharp glare, wiping some precum off the side of your lips with the back of your hand before replying, “Come on, Dewey, you really think I’d do that? I said that because I mean it.” You leaned over and scruffed a hand through his soft head of hair, before returning your hand to his cock.
“Ah…” he gasped. You brought his dick to your mouth, and began to hum as you took him in further. Dewey groaned at that, and he bucked into your mouth. Your tongue licked the underside of his cock from inside your mouth, and finally you felt the back of your throat come into contact with his dick.
You stayed there for a moment, getting reacquainted with the sensation, before going a little further, attempting to fit all of him. Your face came into contact with his curly pubic hair, and you hummed again.
“Oh my God, I don’t think I’m going to last much longer.” Dewey warned. Despite that, you continued to deep throat him. You started to gag a little more as time went on, it wasn’t exactly the most comfortable feeling, especially for your jaw, but looking at Dewey’s face of pure bliss as his cock was sucked for the first time was very much so worth the momentary pain.
Only a few moments later, he began to jerk wildly into your mouth, grabbing your head and grinding it against his crotch. Under your lips you felt his balls tighten before cum began to spurt in your throat. He continued to hold your head in place for several more seconds, before finally releasing you, looking completely spent.
You leaned back and wiped your mouth with the back of your hand, panting heavily to catch your breath. You noticed that Dewey was still looking intently at your breasts as they rose and fell due to your intense breathing.
“So, I’m getting the impression that you’re a boobs guy?” You teased, and it was pretty funny to watch his gaze snap to your face. He even looked a little guilty, which you found adorable.
“It’s okay, I want you to look.” You said. His dick twitched at your promiscuous words, and you decided to stand and finally remove your pants.
You looked directly at Dewey as you did so, and made a show of removing your panties as well. He watched, eyes lidded incredulously at the sight of you.
“Can I touch you again, or are you still too sensitive?” You asked. Dewey blushed at your blunt question, but responded, “Um, it’s probably okay.”
You were still holding your panties in your dominant hand, and you reached out towards his cock, and began stroking it. His breath hitched at the feeling of the fabric and your hand against his already hardening member, and you enjoyed the look of pleasure on his face immensely.
“How often do you masturbate?” You asked casually.
His eyes blinked open, and he grunted before saying, “A lot. It depends on the day, but sometimes it can be at least 3 or 4 times.”
You smiled at his surprisingly honesty, and decided to ask, “Have you ever thought about me?”
Dewey tensed a little, and looked around the room as you continued to pump his dick. “It’s alright, you can admit it, Dewey.” You coaxed him sweetly.
He looked embarrassed, but eventually he nodded.
You grinned at him and said, “I want you to be thinking of me next time you masturbate.” He moaned, and you gripped the base of his cock tightly, before finally throwing your panties aside.
Dewey watched, fascination evident on his face, as you crouched over him, and hovered just above his dick. “Alright, you can kiss being a 29 year old virgin goodbye, Dewey.” You announced, before proceeding to lower yourself enough so that his aching tip was brushing against your folds. You grabbed his dick, and held it as you continued, plunging the head of his cock inside of you.
As you did so, you looked directly at him, and he closed his eyes before groaning. Dewey reached over and grabbed your right breast, and you continued taking in his entire length.
“You’re so beautiful.” Dewey said, his voice husky, and your toes curled at his tone. You moaned, and said, “Ah… Dewey… I love your voice, talk more, please!” You were on the verge of begging.
Dewey seemed a bit surprised by your admission, but he continued without question, saying, “I can’t believe you’re letting me do this…” he panted heavily, sweat dripping on his forehead, before continuing, “It feels so amazing being inside, better than I ever thought it could be…”
You finally began to move, enjoying the sensation of his dick rubbing against your clit at every thrust. Dewey’s hands moved to your hips, and he began to buck into you, although each of your rhythms were slightly off from each other. You began to roll your hips as Dewey continued his thrusts, and he gasped at the feeling.
“Shit, I’m getting close!” He said. Although the very thought of him cumming inside was tempting, your more rational side decided it probably wasn’t the best decision ever, so you lifted yourself off his cock, and tried ignoring how empty you felt as you stroked him to completion, his cum getting all over your stomach.
You continued sitting on top of Dewey, enjoying the display laid out below you, as you began to circle your clit. Your pace had started off as leisurely, but as the minutes passed you were starting to get more and more desperate for release. Actually, you were so focused that you didn’t even realize Dewey had apparently regained coherency, and was intently watching you masturbate.
“Um, can I help?” Dewey offered, before continuing, “I mean, obviously I’ve never…” You opened your eyes and paused, enjoying his embarrassment and uncertainty. “I’ve never… you know, but. I’m more than willing to learn!”
“Alright.” You eventually agreed, dropping your hand from your crotch, and using his stomach to steady yourself, before falling back onto the couch, propped against the pillows. You spread your legs and explained, “It’ll be easier for you to see from this angle.”
Dewey’s seemingly ever present blush had returned, and he seemed a bit flustered, so you took initiative, grabbing his wrist and yanking it towards your nether regions. He fiddled your clit with his thumb for a moment, although he didn’t seem very confident in his actions, eventually asking, “Can… Can I lick you? Is that something you like?” He asked.
You simply nodded. If that made Dewey more comfortable, well, you didn’t care, provided you got to come, and hopefully soon.
Dewey brought his face to your crotch, and you could feel every inhale and exhale he made against your inner thighs. He looked for several moments before finally giving your vaginal opening a lick. He continued upwards, stimulating your clit with his tongue.
He leaned back and looked up at you, whispering, “You taste really good.”
Dewey began to lick your slit again, his left hand gripping your leg while his right moved to work your clit. He was actually surprisingly good at this. You let out a moan, and that only further motivated him to continue, you felt his tongue speed up, and he pushed it deeper, while continuing to circle your clit with the perfect amount of pressure.
“Oh, God, Dewey!” You cried. It wasn’t going to be much longer if he continued like this. You looked at the beautiful man below you, taking in his tousled hair, passionate facial expression, his adorable nose that was currently pressed against your thigh as he sloppily licked, kissed, and sucked you…
“Come for me, baby.” Dewey said in a gruff voice, and even though his dirty talk needed some work - he clearly felt and sounded awkward saying that - it still brought you over the edge, just because it was so Dewey.
He continued to press his face against your opening as you rode out your orgasm, although he was lapping simply at your folds now, as compared to his more fervent movements earlier. Dewey leaned back and murmured, “Delicious…” before flipping the both of you so that his back was on the couch and your stomach was pressed against his chest.
You closed your eyes and enjoyed the feeling of yours and Dewey’s chests rising and falling rapidly against each other. You were feeling especially soft at the moment, and opening your eyes, you brought your dominant hand to Dewey’s curly head of hair and carded through it gently. Dewey’s eyes were closed, but his expression was that of bliss, and he even leaned into your touch, obviously enjoying himself.
Dewey squeezed you close, and you spent the next couple of minutes cuddling with him. You could tell he was starting to get restless, and his thoughts were probably racing a mile a minute. He finally opened his eyes, broke the silence, and simply asked, “What now?”
You opened your eyes too. While you didn’t really want to do this right now, you probably had to, but… that didn’t stop you from teasing him a little. “Come on Dewey. You can’t just enjoy the fact that you just lost your virginity? You already have to ask the hard questions?” Your tone was light, but you meant your words.
He gave you a fake pout, but continued looking at you, waiting for a response. You contemplated this for a moment.
“Dewey…” You start, “can I think on it for a bit? I really didn’t come here expecting to get laid tonight, so… it’s a lot to process.”
He let out a scoff, but seemed to accept that answer, replying, “You and me both.”
You’re just freshening up in the bathroom once Ned arrives home, so while you can’t verbally communicate what you’d really like to say at the moment if only you were in private again, you opt for a pointed glance as you say your goodbyes.
Dewey seems to get the message.
-
It’s chilly out the next time you come around. You wrap your scarf tighter around your neck as you climb the stairs towards Dewey and Ned’s apartment. The building is over a hundred years old, it relies on radiant heat and has a single elevator that’s broken more often than it’s working.
Ned opens the door to let you in, and you notice that Dewey’s Converse are nicely organized for once, instead of being sprawled around the foyer like usual.
As you follow Ned into the living room, where he and his girlfriend - Patty, you learn - are watching a movie and eating pizza on that same couch, he announces to you, “Hey, you won’t believe this - Dewey actually paid his share of the rent for once - and it actually seems like he might continue to going forward!” Behind him, Patty makes a face, clearly unimpressed, but… well, it’s a start.
Ned also tells you Dewey’s in the shower and that he should be done soon. You round the corner towards his room and find it shockingly tidy for once.
He really has been making a concerted effort… You think fondly to yourself.
Dewey enters the room a few minutes later with just a towel wrapped around his waist, clearly surprised to see you sitting at the edge of his bed. You give him a smile and murmur, “Dewey, I’m proud of you.” He seems incredibly pleased that you’ve recognized his efforts, and settles next to you on his bed. You continue, “I-I’d be happy to be your girlfriend, provided you continue making changes like these.”
Dewey gives you a goofy smile, and replies, “It’s a lot easier to avoid being a screw up with you around, baby.”
Honestly, despite those words, you weren’t convinced Dewey wouldn’t slip back into his old habits eventually, but the seasons changed and then he formed School of Rock, and both his personal and professional life seemed better than ever before.
Eventually, you stopped waiting for the other shoe to drop, and realized that Dewey Finn was truly a changed man, and you were beginning to love this self assured, fulfilled, happy version of him so much.