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We Will Have Lessons

Summary:

Colin Bridgerton has a lot of things going for him. He's over six feet tall, has silky, chestnut brown hair that curls naturally in a most fashionable way, and a smile that's been known to make women ages 2 to 92 swoon. Beyond the surface-level things, he's also smart and interesting and treats others with kindness and respect regardless of how he knows them and what walk of life they're from. Objectively, he's an absolute catch. Any girl would be lucky to be his, even just for one night. So, why then, at 26 years old and with all that going for him, is Colin Bridgerton still a virgin?

--

Or, the one where Penelope platonically takes her best friend Colin's virginity and helps him through his sexual awakening.

Notes:

Hi! Back to modern Polin again! I've explored the idea of Pen being a virgin well into her 20s before (We Found Wonderland) and have been thinking lately about how the dynamic might play out in reverse. So, that's how we find ourselves here :)

Please note that this story (and this first chapter specifically) involves Colin reflecting on his struggles with sex and labeling himself. He doesn't think or talk about himself very kindly in some ways, but of course there's nothing abnormal or shameful about what he's going through. Sex and all the hoopla around it is complicated for lots of people. I tried to treat it sensitively while at the same time letting this chapter reflect what I think might be realistic thoughts or feelings someone like Colin might have. Luckily, he has a Penelope to help him through this and affirm that he's perfectly normal and that everything's going to be OK.

I'm envisioning six chapters with alternating POVs, but per usual the chapter count is subject to change :P

Hope you enjoy! Happy St. Patrick's Day!

xoxo

Chapter 1: Colin

Chapter Text

It's a pretty unremarkable Tuesday night that eventually leads Colin Bridgerton to one of the most remarkable conversations he's ever had in his 26 years of life. He's at a pub with his best friend Penelope Featherington, known affectionately to him (and her other best friend who just so happens to be his sister) as Pen. She goes out for happy hour drinks on Tuesdays with her work colleagues, and since he's staying in the spare room of her flat at the moment, she invited him to come down and join them.

Colin's a pretty affable guy. He gets along naturally and easily with people. Talking is second nature to him, but he's also just as comfortable sitting in a relaxed silence sometimes too. It's why he didn't have any hesitations coming down to the pub and entering the mix of Danbury Publishing junior editors. About half an hour into the experience, though, Pen is not so subtly pushing him into the one kind of social interaction that gives him pause.

The young woman's name is Vera. She's a 24-year-old fellow junior editor on Pen's team, and she just so happens to be, as Pen herself made a point to mention in her special introduction, very interested in his travel social media channel and a big fan of his. Vera is also tall and slender and dark-haired and objectively quite lovely. It's an attempted romantic set-up if there ever was one, and unfortunately it's not the first time Colin's endured this sort of thing. It is, however, the first time he's endured it from Pen herself.

You see, Colin doesn't really flirt ever, which is because he doesn't really date ever. It's one aspect (and admittedly a very big one) of the young adult social experience that he just can't seem to engage in successfully. He's tried plenty and with lots of different types of women, but he's never found anything remotely resembling success save for a short-lived relationship in his teenage years that ended in complete and total disaster.

At the behest of his sister Daphne (the most determined of his siblings to set him up with someone) and his brother Benedict (the most sexually fluid and open-minded of his siblings), Colin has also previously considered the possibility that his struggles with dating and romance are specific to that of the female gender. After several failed attempts at flirting with men, a couple failed attempts at going on a date with a man, and one failed attempt at kissing a man, he felt confident in his assertion that his struggles with women were not because he's secretly been attracted to men. In fact, he felt confident after having those experiences that it was really the opposite for him.

Though he's never allowed himself to delve too far into researching whether there are other people like him out there in the world for fear of what he might find, Colin has Googled the terms asexual and demisexual before too. He can identify with some aspects of the two and definitely more of the demisexual characteristics, but they ultimately feel like two more labels that don't seem to quite fit him. It's not that he's not at all attracted to people, and he also hasn't found that his feelings of sexual attraction or arousal are only prompted by deep, emotional connection. He has the feelings pretty frequently. It's acting on them that he struggles with most, he thinks.

So, Colin's just always viewed himself and his sexuality and his need for human intimacy as different than any other frames of reference he has in his life. He likes women, yes, and certainly appreciates a beautiful or a charming or a mentally stimulating one. But he can never seem to get comfortable enough with anyone for more than a little kissing, which he spends the whole time in his head about and wondering if he's doing it right anyway. And that is why, at 26 years old, Colin Bridgerton is still a virgin.

It's his secret shame—the thing he's never divulged to anyone ever. Not even Daphne when she's tried to get him to go on the apps or set him up with her friends. Not even Benedict with all his open-mindedness and unique brand of brotherly sensitivity. Not even Pen with their warm, close, and easy bond.

Colin also doesn't really think anyone in his life suspects he's still a virgin too. He does a pretty good job of talking around the subject in front of friends and his brothers. He's also sort of cultivated the idea that he's just really private about this sort of thing. That he doesn't like to openly discuss his relationships and dalliances with women openly.

So, the attempted set-up with Vera might not be entirely foreign, but it does make his stomach ache in a way that goes beyond just his usual discomfort with this sort of thing. He thinks it's because it's Pen's doing. She's never tried anything like this before, and he feels weirdly and probably unfairly hurt that she's doing it now.

Eventually, after Colin excuses himself to use the restroom and takes a long time to come back, Vera seems to have caught on to his lack of interest in the thing she seems interested in with him. He finds her further down the bar and talking to someone else at that point, and he therefore breathes a sigh of relief.

Unsurprisingly, Pen soon sidles up to him and when he's in the process of closing out his tab.

"You're leaving? I just got you another beer."

He looks down at the freshly poured Guinness in the glass she's just slid in front of him. He really doesn't feel like sticking around with all her co-workers and frankly even her, though. At the same time, refusing the drink she's specifically gotten him seems a bit dramatic too.

"Thanks," he says quietly before he lifts up the glass and takes a short sip. "I'll head home after."

She quirks her lips to the side and scans him over for a moment. "Are you cross with me? For introducing you to Vera?"

Colin opens his mouth and closes it, a little surprised at her immediate assessment of his current state when he probably shouldn't be considering how well she does know him after all. He doesn't even end up replying, though. She has her answer just by the expression on his face, it seems.

"She's nice and pretty and was excited you'd be coming," Pen explains with her brow furrowed. "I didn't think there was any harm in linking you two up. I'm sorry if it was awkward or she's not your type or whatever."

He sighs once and takes another sip of his beer. "It's fine, Pen. I just… I hate being set up."

"Why?"

"Just because," he answers dismissively. "Let's just move on, yeah?"

Pen frowns at him for several long seconds, and he knows quite clearly that she's not pleased at his attempt at shutting her down. Thankfully, though, she goes along with it and takes a sip of her own cocktail and nods.

Half an hour later, however, when the pub clears of Danbury Publishing junior editors and it's just the two of them left, she brings it back up.

"I'm sorry. I know you didn't want to talk about it before, but I'm just so curious. Why are you so opposed to being set up?"

Colin huffs and shakes his head once. "Pen."

"Please?" she whines and juts out her lower lip in a way that always affects him. "I want to understand. Daphne's mentioned before that you've gotten mad at her too for this kind of thing."

He rubs his face. "It's just… I'm not really into dating at the moment. I'm trying to figure my life out, remember?"

"Yeah, but… you've been like this for a while. Years, in fact. So, why don't you just have another sip of that beer and tell me the truth?"

Colin frowns at her. "What truth?"

"That maybe… possibly… you're… gay?"

He laughs at that and shakes his head. "No, I'm not."

"No?" she questions with wide, eager eyes. "Are you sure? It's totally okay if you are or you aren't, you know. Or if you're still figuring it out! We're all a little gay at least, right?"

Colin's eyebrows raise. "Are you?"

She shrugs. "I don't know. Just a little, maybe. I dabbled for a brief moment in time at uni…"

He's got a lot more questions he wants to ask about that, but she's barreling ahead with her own line of questioning instead.

"It's just… Vera's pretty and cool and smart, and yet it looked a little like you were in pain trying to talk to her. What's that about, Colin? Why is it that you're always like that when a woman's trying to flirt with you?"

"It's not because I'm gay, Pen," he says tightly, growing annoyed that she's pushing this narrative further. "I know I'm not, okay?"

"Okay, okay," she answers in a rush and raises her hands. A beat of silence passes between them, though, and her expression grows soft and her eyes are full of warmth and concern. "I just… I don't understand and I'd really like to."

"I can't have sex."

Pen's eyes immediately widen, and acid starts churning and bubbling in his stomach. He can't believe he just said that. Why the fuck did he just say that? What was it about that simple comment, that look she gave him, that made him crack? Why did he just spill out the truth he's been holding in for so long?

"Oh my God…" she whispers, her eyes flitting over his face and her cheeks going pink. "Oh my God. Do you… Do you have a disorder or something?"

Colin opens his mouth to answer, but this moment is so supremely mortifying that nothing comes out and Pen keeps right on going.

"Oh God. I'm so sorry. I didn't mean to push you. God, you must hate me. I'm so sorry."

He clears his throat roughly and finally manages to shake his head and speak. "N-no. It's… I don't think it's like that. I don't think it's totally… physical at least."

Her expression goes from outright distraught to something a little more wary. "What do you mean?"

Colin catches the eye of the bartender standing a few paces away and very clearly eavesdropping despite her gaze being on the wine glasses she's drying and stacking on a rack above her head.

"I'm not talking about this here."

Pen lets out a sigh before lifting his beer, which only has about two sips left, and holding it up for him. "Then I think it's time to go home."

He protests the whole way back to her flat, which in actuality is only a single block, but she's insistent. She makes a comment that she can sense they're on the precipice of something important—that there's nothing he can tell her that's going to scare her off or make it so she doesn't want to be his friend.

Colin tells himself that last bit over and over again while they go inside her flat, take turns in the bathroom, and he waits for her to pour them two glasses of whiskey for while they sit on the sofa in the living room.

"I don't want to talk about this," he tries one more time, swirling the amber liquid in the glass and watching it spin and create a little whirlpool.

"I kind of feel like you secretly do, though," Pen argues but keeps her tone pretty gentle at the same time. "I know I was pushing a little bit before, but you did just… kind of put it out there."

She has him there. "Fine."

Pen looks at him somewhat expectantly for a few moments before she nods at him slowly. "So… Talk to me."

"I don't know," he tells her tightly. "I don't know what you want me to say."

"Do you want me to ask you questions instead?"

Part of him wants to say no, but he nods. "Yeah."

"Okay," Pen says before she straightens in her seat on the other end of the sofa. "So… You said you don't think it's physical in nature. Or at least not totally physical. Why you can't have sex… Yeah?"

Colin nods.

"What does that mean?" she starts before changing course after she seemingly correctly interprets that question as being too open-ended for him to want to answer. "Do you… ever feel aroused? At least sometimes? Sexually, that is?"

He nods a second time. "Sometimes, yes."

"And you can get an erection?"

He can't help the blush that spreads over his cheeks the third time he nods.

"And you ejaculate too?"

Colin scowls at her then. "Jesus. I feel like I'm at the doctor."

"Sorry," she admits with a laugh and a blush of her own. "I'll use less medical terminology… Do you come?"

"Yes," he says through a huff. "I can come."

"When you mas—" she cuts herself off before continuing. "When you jerk off?"

When he nods yet again, Pen seems to frown a bit. "And how often is that?"

"That I have a wank?" Colin asks incredulously. "I don't know. Like… almost every day in the shower."

Her eyes go wide at that, which has him immediately second guessing himself. "Is that a lot?"

"I mean, no," she rushes to apparently reassure him. "I don't know. Maybe for someone who is claiming they can't have sex… I'm not an expert here, though."

"I'm not claiming it, Pen," he reminds her tiredly, rubbing a hand roughly over his eyes. "I've tried to get there with people, and I just… can't."

She's quiet for a few moments, her teeth digging into her bottom lip while she looks him over and thinks. He knows that she said there was nothing he could tell her that was going to make it so she didn't want to be his friend anymore, but he feels pretty low right now. He feels like a freak and broken and damaged in a way that he really doesn't think he's gone through anything that makes him worthy of being so damaged. And all while these thoughts and emotions are flooding through him, Pen is apparently figuring him out and putting together the pieces of the puzzle he's been trying to hide from everyone in his life since he was a teenager.

"Colin," she says softly. "Are you saying you're a virgin?"

For one brief, horrifying moment, he thinks he's about to cry. It's a sudden, bursting sort of sensation that shoots through him, though, at being so completely seen. Even Daphne and Benedict, two of the closest people in his life and who have gotten into at the least the surface-level of all this shit with him before, never pieced that together.

Thankfully, though, Colin doesn't cry. He manages to swallow down the lump of emotion rising in this throat and forces a bitter smile on his face instead.

"Embarrassing as fuck, huh?" he quips. "I told you I wasn't normal."

"No," Pen urges, scooting close to him on the sofa and putting a hand on top of his own that squeezes gently. "Don't do that. You're normal. You're the best. I'm just sorry that I've… pushed you on this if you really didn't want to talk about it. I just didn't know."

"Well," he says slowly. "Now you do."

"I'm sorry I assumed otherwise," she continues. "I just always thought… Marina at least…"

Colin snorts at the memory of his first real girlfriend. "We fooled around a little, but we never ended up… She was… Well, you know exactly what happened there. Everyone does. I don't have to rehash it."

"No. You don't," she answers quietly. "Is that when you started feeling like this, though? After that experience with dating and breaking up with her?"

He frowns at that. "I… I don't know. I never really tried to have sex with anyone before her. I don't have a pre-Marina experience to compare to in this regard."

"Yeah, but… I think I understand a little bit," she answers after a beat. "Or at least, I have an idea."

"What?"

"It's a trust thing," Pen suggests gently. "You've built up a wall that's impossibly high after she betrayed you in such a… vulnerable way, and now no one can ever get over it."

He frowns at that even if it does really resonate with how he's always felt but always been afraid to examine too closely. "I hope that's not the case. That no one can ever get over the wall, I mean."

She tilts her head to the side in question. "You want to have sex?"

"I…" Colin trails off while he bites his lip and gathers his thoughts. "I want to want to. I want to be normal."

"You are normal. You—"

"Don't," he interrupts, though. "This isn't normal, Pen. I'm a 26-year-old guy who's too… too… too afraid to put his dick inside a girl. Don't tell me that's normal."

"This isn't about fear," Pen says in a rush and so earnestly. "It's about trust, Colin. It's about getting to know someone and building that trust over time. One night stands might not be for you or a fling here and there—that's fine. They're not really my style either. But building trust and comfort before you try… That sounds so much more attainable, doesn't it?"

Colin takes a big sip of his whiskey before he shakes his head once. "I did try that once. After uni…"

"What do you mean?"

"I mean… I dated a girl and tried taking it really, really slow. I didn't kiss her for like over a month. It was months and months after that before we tried anything else."

"Angelica, right?" She pauses for him to nod and then purses her lips. "What happened?"

"Once we started fooling around, I… I made her come, but she couldn't make me come." Colin winces and rushes to correct himself. "That's not fair actually. I couldn't come. It wasn't her fault."

"What was she doing to you?"

He blushes at that. "Giving me a handjob."

"Did it feel good while she was touching you?" she asks quietly. "Even if you didn't come in the end?"

Colin thinks about that before he shrugs his shoulders. "A little? I don't know. I was too in my head, and then it was so embarrassing with how long it went on and I just… couldn't get there. So, yeah. She obviously felt weird about the whole thing, so we broke up."

"You didn't at least try again?"

He shakes his head. "No, definitely not."

Pen hums and sits back against the arm of the couch, pulling her legs up as she rests her whiskey glass on her knee and looks off into space for a second.

"What?" he prompts, curious at her sudden change in demeanor.

"Did you really like her?" she asks in an almost challenging tone of voice. "Like genuinely?"

He takes another second to reflect. It's been a while since he's even thought of that whole debacle with Angelica. Now, though, with time and distance from it all, he thinks maybe he can see the dynamic at play a little more clearly.

"I didn't not like her," Colin answers truthfully. "She was great."

"But…?"

"But," he admits. "I don't think I ever felt… fully connected to her. Just like I've never felt fully connected to anyone romantically. In the end, it didn't matter how slow we took it and how well I got to know her."

"You didn't trust her," Pen states, her eyes full of tenderness and concern.

He shakes his head. "No."

They look at each other in silence for a little while longer, but the conversation has reached a quiet, natural end even if he doesn't feel much like he has a resolution to his problem. Although, that's not really a fair expectation, is it? He's gone his whole life avoiding talking about this stuff with anyone else. Pen's done more in the matter of about an hour to help him than he thinks he's ever even tried to help himself.

They take turns again in the bathroom then before saying a quick goodnight passing each other in the hall. Colin's just gotten into bed in his white t-shirt and boxers and is pulling the covers over himself when he hears a quick knock on the door and it pushes open.

"Hey," he starts. "What's—"

"Do you trust me?"

Colin stares at Pen in confusion. She's standing in the doorway of his room and in her fluffy bathrobe that goes all the way down to her ankles. He thinks it's designed hit somewhere around the upper shin area for people of closer to average height, but she certainly doesn't fall into that category.

"Of course I do."

Her eyes go wide at that, and it takes him another moment to think back to the conversation they'd wrapped up a little while ago in the other room. Suddenly, he understands the true implication of her asking him that question and him offering that response so effortlessly.

"W-wait," he starts and sputters. "What do you mean by that?"

"Would you want to try with me?"

His heart starts to pound in his chest, but he refuses to believe she's actually really asking him this until the words directly leave her lips.

"Try what with you?"

"Would you like to try and sleep with me?" she says with a brightness in her gaze that distracts him temporarily even as he's properly reeling over this question she's posing. "Do you want to see if I can help?"

Colin can't help but inhale once the shock and frankly the outrageousness of this conversation sinks in. "Penelope!"

She blinks at him for a beat before she lets out a bubble of laughter and slaps her hand over her mouth. Before he's even really worked himself up over being annoyed that she's laughing at a time like this, she's looking at him apologetically and rushing to speak first.

"Sorry, sorry! I'm not laughing at you, I swear. It just… surprised me. You never use my full name. That's all."

Colin swallows and shakes his head once. "We can't."

She sits down on the far edge of his bed, way down by his feet thankfully, and frowns. "Why not?"

"Because we're friends," he supplies with an exaggerated shrug of his shoulders. "And friends don't—"

"Help each other through things?" Pen interjects with an arched eyebrow and her lips pursed in a challenging expression.

"Be serious."

She huffs at that. "I am! You've helped me loads of times, you know. My dad's death and the subsequent investigation and fallout and financial ruin… Through going no contact with Mum for a while when I was in uni…" Pen lets her words linger in the air for a few moments before she shakes her head of the reminder of those painful times in her life. "You've helped me through every hard thing I've ever dealt with, Colin. Let me be there for you now."

As much as he can appreciate her earnestness and the beauty of the sentiment she's trying to convey, it doesn't help him feel at all better about his situation or any more like taking her up on this absurd offer.

"This is different and you know it."

"Why?" she bemoans. "Because it's sex?"

"Yes!"

She frowns severely and bites her lip for a second before answering. "I really think part of what's got you all twisted up is that you're building it all up in your head. It's been so much time that you've made sex this big, insurmountable feat when really it's just… natural. It's human nature. It doesn't have to be scary, Colin. I promise I'll try everything I can not to make it scary with me."

Colin swallows as he processes yet another truth about his psyche she's surmised for herself this evening. There's still a part of him that's worried she's wrong and that there is something deeply wrong with him—that he's incapable of ever being fully intimate with someone. But it does seem a bit ridiculous to never test the theory and potentially commit himself to a life of celibacy at 26 years old when really it might not be necessary.

He also is struck by a unique notion somewhere in the tangled up mess his thoughts are in tonight. He does feel like he actually wants to say yes and try. He's been interested in the idea of having sex with someone before, but he's never genuinely wanted to say yes or pursue it when the real thing was a real possibility in front of him like this. Not since he was a teenager and thought himself in love with a girl who was using him and lying to him and ultimately left him humiliated and brokenhearted.

Pen pulls him from his swirling, spiraling mind after a little while, her hand resting atop his foot over the covers of the bed. "I'll take care of you, Colin. If you'll let me…"

He's struck by that same feeling that he didn't recognize in himself from earlier at the pub. It's just like the one he was overtaken by when she told him she wanted to understand him and looked at him with all that vulnerability and openness and kindness in her eyes too. He'd opened his mouth and blurted something out to her he swore he'd never tell a soul in his life, and now here he is doing something similar the second time he's struck by the feeling too.

"O-okay. We can try."

Pen doesn't look shocked by what he blurts out this time. Instead, she looks rather thrilled as a pretty, bright grin spreads across her face and she gives his foot a squeeze. He feels stupid about it, but that affectionate and surely innocent squeeze makes him jolt like she'd done something much more intense and his stomach starts to swirl with rising anxiety again.

"Not tonight," Colin says in a rush and with his fingers clenching at his sides. "I… Yeah. Not tonight."

"That's probably smart," she answers sweetly and easily. "We've been drinking a bit, and those aren't ideal conditions for something like this. I want you clearheaded."

He tries not to focus on her phrasing—that she "wants" him in any state—and instead takes a deep breath and lets it out slow. "When then?"

Pen shrugs. "Tomorrow?"

Colin blinks at her and frowns. "I'm going to look at flats with Mum tomorrow."

She gives him a slightly teasing smile, but it's teasing in a friendly, comfortable way. "People are allowed to have sex after they look at real estate, you know."

"Right," he answers, chuckling at himself and running a hand through his hair. "So, tomorrow then…"

"Tomorrow," Pen agrees a nod and her smile remaining plastered on her face. "I'll make dinner after I get home from work, and we'll go from there."

There's not anything more discussed then. She leaves him with one last rub of his foot, a move that sends a spark shooting up his leg. The feeling pools in his belly and even makes his cock give the tiniest of little twitches in his boxers. Thankfully, she can't see any indication of that, and she doesn't seem at all fazed by the stunned, overwhelmed expression he's sure he's got on his face as she wishes him goodnight and slips out of his room again.

Colin lets his head thunk against the headboard once Pen's gone, and he closes his eyes. This night was already bizarre enough with her trying to set him up with her co-worker and then her accidentally pushing him into revealing his deepest, darkest secret. Now, though, he is confident he can say that this night is without a doubt the strangest one he will ever have. Because it's the night he agreed to do what he's terrified is impossible with his best friend. And all he can pray for is not that even that he'll be successful and somehow Penelope Featherington is going to cure his problem with sex and divest him of his virginity. All he can really pray for is that he won't lose her in the process of attempting all that.