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“I fucked her…”
Mickey and Ian watched as Lip lit up his cigarette and sat down on the porch.
“Who’d you fuck? Spell it out Nancy Drew.” Mickey stated as he started to puff out some smoke.
“The maid of honor.“ Lip sighed.
“So isn’t that like normal….a tradition?”
Lip glared over at his brother. “She…she said it was her first time.”
“Oh so you fucked the virgin right out of her.” Mickey chuckled.
At that moment Lip knew he was screwed.
~A few hours earlier~
Lip had no problem being Brad’s best man even if he sucked at tying his tie. Sure any other wedding back in the day would have been a way to get wasted but now that he was sober Lip wasn’t sure what to do.
Then came in Y/N, the maid of honor, and Cami’s sister. Lip had only met Y/N once the week prior in passing as he helped get the rental tables. But there she was short packed into a big pink fluffy bridesmaids dress dancing with her sister and their twin nieces.
At least someone in the bridal party was enjoying themselves.
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Lip walked out to grab a smoke smacking on his pack before the nicotine stick slammed out.
“Those things kill you know?” Y/N stated as Lip glared at her mumbling something under his breathe which sounded a lot like fuck you.
“Gimme.” Y/N grabbed the stick out of Lip’s mouth, him giving her a death glare, as she plucked it into her own.
Lip gave her a look as she coughed after her first inhale. “Don’t smoke?”
She shook her head. “Never tried one,” Lip gave her a quizal look, “My dad smokes like five packs a day, never tried one cause of that.”
“So you decide tonight to try one? With me?”
“Well Lip… what kind of name is that?”
“Short for Philip.”
“Hm strange anyways Philip.” She popped the p at the end. “Since Brad can’t handle his liquor and my sister is up his ass I gotta do something adventurous at this wedding.”
Lip looked at her wondering if he should be insulted about the alcoholic comment about his friend instead he shook his head.
“So smoking with the best man is the best you came up with?”
“Well nothing else has come to mind.” Y/N handed Lip back the cigarette. “And I’m pretty sure you are one of Brad’s sober buddies so I’m guessing you don’t have anything on you.”
“Afraid not.” Lip placed the stick back in his mouth not before seeing the pink lipstick stain on it. “You drink a lot?”
“If the day ends in Y…” She chuckled; her back leaning on the stone building. “No more of a social drinker, you know birthday parties, girls night out, when a boss fires you because you won’t suck his dick and oh at weddings I do.”
Y/N moved off the wall now standing right in front of Lip. “Like I said no booze so you got any ideas for me hotshot?”
Lip blew the smoke into her face as he flicked his bud out, throwing it onto the ground. “Hm, maybe one.”
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They had made it to a broom closet without anyone noticing which they were both surprised about. Lip had her up against the wall crashing his mouth into hers. She tasted like mint gum with a hint of nicotine. She was hot and wanted an adventure. It was the least he could do, right?
Hands were roaming freely; hers leading idly by his belt buckle. Lips' hands found a place caressing her breasts as Y/N’s stopped before she could undo his pants. She pulled away just enough to bite his bottom lip making him moan.
“I have never done this before.” Her eyes twinkled looking up at Lip.
Lip gave her a look. “Want me to stop?”
Y/N shook her head no and that was good enough for Lip.
His hands fumbled under the fluffy dress trying to find her panties to push them to the side. Finally he thrust into her making her moan, Lip hoping it was out of pleasure.
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A couple days later Lip couldn't rush out of the house fast enough, Mickey kept the jokes coming. “I bet she said your dick was the biggest she's ever seen. Bet you got a four incher. Hey if you sucked at it she wouldn't know. You were the best she ever had.”
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“Did you have a good time at the wedding?” Brad asked as they worked on the new bike that just came in.
“Ugh yeah you could say that.” Lip grabbed the wrench before he looked back to his friend. “Have you ever fucked a virgin?”
“Yeah, Becky Keller, we lost our virginity together.” Brad chuckled. “Why have you?”
Lip looked at him and down to the floor. “Happened at the wedding.”
“Don’t tell me you fucked Cami’s cousin Caroline? She may look twenty-one but she's only sixteen.” God Cami’s going to kill me, you and then me again.”
“Fuck no.” Lip shook his head. “It was Y/N.”
“Y/N..Y/N? Cami’s sister Y/N?”
“Yeah the maid of honor.”
“Or dishonor at the sound of it. Wait, she said she was a virgin?”
“Yeah basically kept asking me for ideas for an adventure and well we ended up landing on fucking.” Lip ran his head threw his hair as Brad laughed. “Not funny Cami’s going to kill me. It's kind of weird right? She's what? My age and a virgin? How does that even happen?”
“Trust me she’s no virgin.”
“You know for sure?”
“Walked in on her and some guy once or twice. Plus she tells Cami everything. Hard not to overhear.”
“What the fuck.” Lip stood up and started walking out of the shop. “Where does she work again?”
“Coffee shop. East 18th street.”
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It didn't take long for Lip to find the coffee shop. He was pissed; for starters he had never taken anyone's virginity let alone be lied to about it. It wasn’t that Lip didn’t enjoy the sex—that at least was great— it was the fact that Y/N lied .
He walked in and saw her. Her long hair flowed as the wind blew into the door. She was behind the counter looking at an order; the tip of her tongue sticking out of her mouth. She looked up; her eyes meeting his.
“Hey there Philip, are you stalking me?”
“The name’s Lip.” He really did want to go off on her right now but thought maybe not with a room full of customers. “Can we talk?”
“Sure, let me get you a coffee and we can sit outside.”
Lip sat at the table and watched as Y/N came out with two coffees in hand.
“Here I made you a normal cup of Joe with a splash of milk. Figured you weren’t a flavor kind of guy.”
Y/N on the other hand had an iced coffee with Caramel drizzle in it. “So what’s up stalker?”
“You lied.” Lip eyed her up and down. “Said you were a virgin.”
“When did I say that?”
“Right before I put my dick in you.” Lip stated; matter of factly, as if that was a normal sentence he said on the regular.
“Never said that.” She took a big sip of her coffee. “I said that I have never done that before, not the same thing.”
“Yeah it is. That’s the same thing!”
“How so?” She took another sip. “Cause how I see it I said I never have done that before…”
“See you just admitted to it.”
“If you let me finish, Philip.” Her eyes glared into his. “I meant that I had never had sex at a wedding let alone with the best man.”
Lip nodded. “Guess that makes sense.”
Y/N chuckled. “Says the guy who came down here to yell at a newly ex virgin. Did you even think of how my newly sexified soul would feel after her deflowerer starts yelling at her?”
“You weren’t a virgin so it’s all good.”
“Some feminist you are.”
“I took a critical theory class once if that counts.”
“How did that work out for you?”
“Slept with the professor so not great.”
Y/N laughed at his comment as Lip proceeded to tell her the story of Philip Gallagher and by chance maybe he would get to know her story too.
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Lip walked home not really sure how they left things at the coffee shop. Something on the lines of that one or the other would call to set up another—“date”— or fuck session.
Lip opened the door seeing Ian and Mickey on the couch watching some crap ass teenage drama which everyone knew was Mickey's favorite show but let him play along as if it were Ian’s.
He sat down in the arm chair; feet resting on the coffee table. “Turns out she wasn’t a virgin.”
Ian nodded, not looking away from the tv. “Who the fuck lies about that?”
“The chick who fucked your brother.” Mickey chuckled at himself.
“Haha, so funny asshole.” Lip rolled his eyes at Mickey.
“It’s probably her kink.” Mickey glared at Lip. “Fuck you if you didn’t figure that out genius.”
Ian rolled his eyes. “So you gonna fuck her again?”
“Thinking about it.”
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It has been a week and Lip hadn’t figured out how to send a text message to Y/N that didn’t start off with wanna fuck so he just avoided the situation. It wasn’t like she was texting him either.
He was drinking a cup of coffee bull shitting with Brad at the shop when Y/N walked in. From their last conversation Lip had learned that Y/N managed a coffee shop, which made sense as Lip got the hint that she was addicted to the stuff, that she was close to her sister and that she liked to be a tease.
“So should I ask if you are stalking me now?” Lip chuckled, shaking his head.
“Maybe or just maybe my sister is making me drop off lunch for my brother in law.”
“Aw and here I thought I left an impression.”
“I’m going back into the office to work.” Brad started heading into the office before turning back around. “For the love of god please don’t fuck in the storage room.”
Y/N smiled. “I think that’s a challenge.”
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A couple months had passed and Lip had finally invited Y/N over for dinner, let’s be honest, it was for sex because he knew well enough that’s what it would lead to.
They had been going at it like jack rabbits that’s what Mickey named Lip’s escapades with Y/N. Lip wasn’t one to share all the details about his sex life but he told Ian and Mickey enough that they knew he was buying condoms on the regular.
Sex at the bike shop (much to Brad’s disgust), sex in Y/N’s car (the back seat must be broken by now), sex at the coffee shop (late at night when she’s supposed to be locking up), sex at her apartment (her roommates liked the show), sex on the L (which would be never done again), sex in bathroom stalls (it grossed them both out), sex at North Avenue Beach (okay maybe they did like fucking in public).
Either way it was about time Y/N be introduced to his bed.
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“You know we could just sneak in the upstairs window. You don’t have to meet my family. I told you what they are like.” Lip groaned as he led Y/N up to the back door.
“Oh ashamed to be seen with me Philip?” Y/N chuckled as Lip’s hand went to the door. “I’ll show mine if you show me yours? You met mine so now it's your turn.”
Lip shook his head as he opened the door. “A deals a deal.”
To his surprise not everyone was crowding around as they walked into the kitchen; Ian and Mickey looked up.
Lip nodded, “Ian…Mick this is Y/N.”
“Hey nice to meet you finally. I’m Ian.”
“You’re letting his fucker fuck you?” MIckey stated as he pointed to Lip. “He must be a good lay like his brother.”
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Dinner was mostly normal. Ian and Fiona kept up the conversation asking Y/N about herself, Debbie was being Debbie but managed to let Y/N at least hold Franny, Mickey stated facts about virgins making Y/N laugh, Y/N listened to Liam as he talked about his science fair project and Carl gave a “sup” as he walked out of the house to do God knows what. Overall Lip thought the dinner was okay especially since it didn’t end in disaster.
After they ate, the family started dispersing from the kitchen table, Fiona heading to Patsy’s, MIckey and Ian to the couch, Debbie left without Franny and Liam went up to bed.
Lip got up from his chair about to make his way up the stairs. “You coming?” Y/N nodded as she followed him up.
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It was a strange feeling to Lip as he led a girl up to his room. Before it was usually just Karen or Mandy dropping by, never him leading someone up to his personal space. He wasn’t worried what Y/N would think of the house; she knew enough about him to figure out about how he lived. It was just a momentary shock in what he was leading her to.
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Y/N looked at the walls seeing some older posters, a few random knick knacks and an ashtray. Lip walked close to Y/N wrapping his arms around her, kissing the top of her head as he breathed in her scent; cinnamon with a hint of his nicotine.
“So did my family live up to the hype?”
Y/N chuckled. “I like them, never a boring moment at shay Gallagher.”
Y/N’s lips grazed his ever so slightly, Lip’s hands found her waist roaming the skin under her shirt.
Lip pulled out of the kiss. “You know I have never done this before?”
“Are you trying to do my line?” Y/N laughed. “We both know you aren’t a virgin.” Her fingers made small circles on the back of his neck.
“No.” Lip shook his head. “I’m not implying that.”
“Hm then what are you implying?”
“I just…” He looked to the ground then back to her. “I just never purposefully invited a girl over to meet my family.”
“Oh so this was your first time?”
“Yeah I guess it was.”
“So I popped your cherry?”
Y/N laughed as Lip smacked her ass. “Come here let me show you something else I can pop.”
Y/N’s laughter filled the room, at this moment Lip Gallagher knew what he was doing for the first time, falling in love.