Chapter Text
Jeff knocked on the door, rainwater dripping off him as he caught his breath. As it opened, he began to speak, "Don't say anything until I've said what I gotta say. I've known you for almost two years now, and I've never taken you as seriously as I should have. You are the strangest, coolest, most genuine person I've ever met, and the thing that scares me about you is how good you make me wish I was."
Annie looked at Jeff, her arms crossed in front of her chest. "Jesus, Jeff, get inside." As Jeff stepped inside her studio apartment, Annie stuck her head into the hallway and quickly looked around before shutting the door and locking it. "What are you doing here, Jeff?"
"I thought about what you said in the men’s room, and when I heard you asked out Rich, I guess I just realized that I don’t want things to be complicated." Jeff stood for a moment, a puddle forming at his feet as he began to shiver. "Before we get into this, can I use your shower? And do you have a dryer or something I can use for my clothes?"
"Seriously? Fine! There’s a hairdryer in the top drawer you can use to try and dry them off with. Let me grab you a towel." Annie walked over to the closet and grabbed a lilac bath towel out.
Jeff took the towel and went into the bathroom, stripped off his soaked clothing, and turned on the shower. As he waited for the water to warm up, he began to look for the hairdryer. Jeff opened the top drawer, noting how neatly organized the various toiletries were. Conspicuously absent, however, was a hairdryer. Jeff, hoping to not have to put on wet clothes back on, and against his better judgment, opened the next drawer, finding it full of feminine hygiene products that were just as neatly organized as the items in the top drawer. Frustrated, Jeff pulled open the bottom drawer, finding a first aid kit and, sitting next to it, a bright purple vibrator. Shocked, Jeff slammed the drawer shut and hopped in the shower.
As Jeff showered, Annie worked on tidying up her apartment a bit. Though it wasn’t particularly messy, she still hadn’t been expecting company and wanted to put a few things away here and there. As she finished straightening up her vanity, she noticed that her hairdryer was sitting on the corner of the dressing table. She grabbed it and walked over to the bathroom door, knocking. "Jeff?"
"Yeah?" Jeff’s voice was higher pitched than normal.
"I have my hairdryer. I guess I forgot to put it away," Annie called through the door. "Do you still want it?"
"Yeah. Sure." Jeff’s voice had almost begun to sound strained. "Just put it on the counter."
Annie opened the door and covered her eyes with one hand. As she set the hairdryer down on the counter, she peeked through her fingers, hoping to catch a glimpse of Jeff’s body. Though the shower curtain was pulled shut and steam filled the room, she could still see his silhouette as he leaned under the running water, one hand against the wall, and couldn’t help but notice the protrusion coming from Jeff’s crotch. "Find everything okay?" Her voice took on a similarly strained and high-pitched tone.
"What? No! I mean, yes! I mean, I didn’t look for anything!" Jeff replied almost panicked.
As Annie remembered the vibrator she kept in the bottom drawer, the color fled from her face. She quickly turned and left the bathroom, shutting the door behind her. Freaked out at the prospect of Jeff having seen her sex toy, Annie did her best to compose herself by finishing up her tidying. Once she was finished, she took a seat on the couch, her hands clasped in front of her nervously.
As the bathroom door shut behind Annie, Jeff felt his heart pound in his chest. Though he was still freezing from the rain, Jeff turned the shower from hot to cold, hoping to suppress his arousal. Despite his own assertion that they tried not to sexualize Annie, Jeff hadn’t been able to keep the thought of her using the vibrator from his head. As the frigid water hit him, he angled the showerhead downwards towards his groin, hoping to quell his erection. Although the idea of jerking off had crossed his mind, he was worried that doing so might cause Annie to question why he was taking so long.
Once the swelling had subsided, Jeff turned off the water and grabbed the towel Annie had given him, wrapping it around his waist after drying himself off. He wrung out each item of clothing thoroughly before plugging in the hairdryer and turning it on. Though his boxer-briefs, tank top, and socks dried out rather easily, his pants and button-down proved much more difficult, becoming, at best, warm, but still very damp. Hanging his pants and the towel on the towel rack and his shirt on the hook on the back of the door, Jeff slipped on his underwear and tank top. Jeff poked his head out of the bathroom. "Annie, I hate to ask, but do you have a pair of sweatpants or something I could borrow? My jeans aren’t drying off quickly enough."
Annie rolled her eyes. "I’ll see if I can find you something." She got up from the couch and went over to her dresser, looking through her sweats. She briefly contemplated offering Jeff a pair of pink sweatpants she’d had since middle school, but decided against it, grabbing a pair of plaid flannel pants instead. She walked over to the bathroom door and opened the door enough to stick her hand in. "Try these."
"Thanks." Jeff took the pants from Annie and pulled them on. Though they fit him around the waist just fine, they were a bit tight in the crotch and close to a foot too short on him. Taking a quick look in the mirror, Jeff did his best to style his hair a bit before exiting the bathroom. As he stepped back into the main room, Annie stifled a laugh at his awkward outfit. "Yeah, yeah, laugh it up. Don’t you have anything bigger?"
"No, Jeff, I don’t," Annie replied curtly from the couch. "You see, I don’t just have clothes for men that are a foot taller than me lying around, typically. And if I did, well, you probably wouldn’t have to ask about it, if you were here at all, would you?"
"Fair enough. It's not like you have a boyfriend." Jeff looked around Annie’s apartment as he tried to force the image of the purple plastic phallus he'd seen from his head. "Nice place you got here…"
"Cut the crap, Jeff. You said you came here because you wanted things to not be complicated. Does that mean you’re going to stop screwing around and be honest about what you want?"
Jeff sat down next to Annie. "I guess so."
Annie laughed harshly, rolling her eyes. "You guess so? Come on, Jeff. Don’t try and act all aloof with me. Do you want me or not?" Annie crossed her arms as she turned to look at him.
Jeff swallowed nervously. "Yes. I want you."
"See, that wasn't so hard, was it?" Annie's face broke into a devilish grin. "Did you have a nice shower?"
"Uh, yeah. It was good. I hope I didn't use up all your hot water though."
"So you enjoyed yourself?"
Jeff looked at Annie, a bit confused. "I guess? I mean, as much as one…does…" He trailed off as he realized what she was getting at. "I'm sure you've had some great showers yourself."
"Oh, you have no idea." Annie leaned in towards Jeff. "I'm sure you'd love to know all about my showers, wouldn't you, Jeff?"
Jeff gulped as his erection returned, a result of both how close Annie was getting to him and the thought of just exactly what it was she did in the shower. Even worse, the pants Annie had loaned him were far too tight to allow him to hide his hard-on except by tucking it up into the waistband, and with her right next to him, there was no way he'd be able to manage that without her noticing. "Uhh…" Jeff was at a loss for thoughts, let alone words, likely a result of his body redistributing blood that normally went to his brain a bit lower down.
"Am I flustering you, Jeff?" He could now feel her breath on his neck and shoulder, even if just barely.
Doing his best to think of unsexy things, like the stench from the inside of Pierce's casts, Jeff fixed his eyes straight ahead and focused his rapidly waning willpower. "I'm fine. Maybe I should check and see if my clothes are dry yet." The pitch of Jeff's voice rose again and the tempo increased, his words almost blending together.
"I'm sure they're still soaking wet." Annie had leaned in so far that she'd had to put one of her hands on the couch to hold herself up and as she did, the tips of her fingers brushed Jeff's thigh. "You don't want to put on wet pants, do you?"
A part of Jeff's brain briefly sparked, the comment about wet pants almost giving rational thought back control before the feeling of Annie's warm breath on his neck and her fingers brushing against his thigh took it out back and shot it. Turning to face Annie, he found his face almost touching hers, and without hesitation, kissed her. Grabbing her by the waist, Jeff pulled Annie onto his lap.
Annie let out a gasp as he did, shocked at the suddenness of the act, but glad she hadn't been forced to kiss Jeff first this time. As they kissed, she felt his hard-on press between her legs and almost instinctively began to grind herself against it.
As he felt Annie's hips begin to rock under his hands, Jeff pulled her in tighter, one hand moving to the small of her back as he used the other to remove his pants.
When she felt Jeff pull his pants off, Annie put her hands on Jeff's chest and broke their kiss. "I'm not having sex with you tonight, Jeff."
Jeff shook his head, trying to break through the fog of arousal. "Right. Of course." He leaned forward to pull the pants back on.
"Whoa!" Annie giggled. "I said I wasn't going to have sex with you. I didn't say you had to put your pants back on." Before Jeff could answer, Annie began to kiss him again, her hand sliding down his body.
Jeff let out a small gasp as he felt Annie's hand wrap around his manhood. As she began to stroke him through his underwear, he rolled to the side, laying her down on the couch, their mouths never parting.
Jeff's hand that had previously been on Annie's back slid around and found its way under her skirt and between her legs. Though she was still wearing her tights, Jeff could easily feel the heat emanating from Annie's crotch. Gently but firmly, he began to rub his fingers in a tight circle.
Annie moaned softly as Jeff began to tease her. Though Britta had liked to talk about the fact that Jeff had been a poor sexual partner, Annie was, as of yet, quite pleased with his performance. Hoping Jeff would feel the same way, Annie slipped her hand through the fly of Jeff's boxer-briefs and wrapped her fingers around his penis, stroking him a bit more aggressively.
Jeff tensed up slightly as he felt Annie's hand on his bare skin. Not wanting to be seen as selfish, Jeff moved his hand and slipped it into her tights. As his hand slid back between her thighs, he felt how wet Annie had become. He pulled her panties to one side and slowly slid his middle finger inside her. He hooked it slightly to draw the tip against the front wall of Annie’s vagina.
It was Annie’s turn to tense up. Her grip tightened in both hands, one on the nape of Jeff’s neck, the other around his penis. As the pleasure built, she broke away from their kiss and pulled Jeff in tighter.
Jeff started to kiss Annie’s neck, moving from her collarbone to her jaw and back. After a while, he felt himself approach orgasm, his breath quickening and his muscles tensing. "Oh, fuck!" he grunted as he came. As his orgasm abated, Jeff redoubled his focus on Annie, alternating between stroking his finger inside her and rubbing her clit in a small circle with his thumb.
Annie arched her back, pushing her hips off the couch. It’d been quite a while since she’d had someone else make her feel this good, and though her vibrator got the job done, it had begun to feel clinical. Between Jeff’s fingers, the feeling of his stubble against her neck, and the subtle scent of his cologne that, despite having showered, still lingered on him, Annie was enraptured. "Jeff!" Annie moaned. "Jeff! I’m-! I’m-!" Before she could finish the sentence, Annie orgasmed, her thigh muscles tensing as her vagina convulsed.
After a few moments, her body relaxed. As she did, Jeff collapsed on top of her. Both of them took a moment to catch their breath. As they lay on the couch panting, their bodies against each other, Annie began to laugh.
Jeff freed his hand from Annie’s tights and pushed himself up, looking at her. "What’s so funny?"
"I was just thinking about how you should have done that at the end of last year. Then we would have had all summer together." Annie pulled her hand from his underwear and started to wriggle her way off the couch. She got up and went over to her dresser, grabbing the box of tissues sitting on top of it. Taking one to clean her hand off, she offered the box to Jeff, who had transitioned to a seated position. "You might wanna…" She nodded her head towards his crotch.
Jeff looked down at the wet spot that had shown up. "Oh, yeah." He laughed awkwardly, taking a few tissues from the box. Pulling his boxer-briefs down a bit, he began to wipe up the mess.
As he cleaned himself up, Annie couldn’t help but peek at Jeff’s crotch. Although she’d technically caught a glimpse of it during the infamous pool game with Coach Bogner, this was the first time she’d actually gotten a good look. Though it was only the second real dick she’d seen, she thought it was a pretty good-looking tumb in a turtleneck. Plus, unlike Vaughn, Jeff waxed.
When he finished wiping up, Jeff noticed Annie looking at his dick. "Like what you're seeing?" He grinned at her.
Annie bit the corner of her lip and quickly looked away, blushing. "Yeah," she replied sheepishly.
"You're a bit of a pervert, aren't you?" Jeff stood up, pulling his underwear up.
Annie gasped in mock offense. "I was just admiring the view. I didn't think you'd mind."
"Oh, I don't. But I also know this isn't the first time you've gotten a peek."
"I have no idea what you mean," Annie replied coyly.
"So you're telling me you didn't sneak a peek during my naked pool game last year? Or last semester during the ‘bottle episode’, as Abed likes to call it?"
"Okay, I may have snuck a peek a few times. But this is the first time I’ve gotten a good look.”
“And?” Jeff cocked an eyebrow.
Annie couldn’t help smiling as she shook her head. “It looks very nice, Jeff. Now, why don’t you get dressed? I’ll give you a ride home.”
“Sure you don’t want me to stay the night?” Jeff smirked.
“Oh, you think it’s that easy, huh? You show up, we make out a little, and then you just get to spend the night?” Annie gave Jeff a wryly inquisitive look.
“Well, for starters, we did a little more than just make out.” Jeff held up his hand, his thumb and index finger about an inch apart as he walked over to the bathroom door. “And second, you live in a really bad neighborhood, I figured you might like having a little company. Plus, my clothes are still soaked.”
“Is Jeff Winger being chivalrous? I might faint.” Annie rolled her eyes.
“You know I worry about you, Annie. I can’t help it,” Jeff replied. “But, if you’re sure you don’t want me to stay, I can walk back to campus. I don’t want you to come back home by yourself this late.” He began to pull on his damp jeans.
“Wait, Jeff. You can stay overnight. I’ll drive you back to campus in the morning.” Jeff grinned and let his pants fall to the floor. “But, you’re sleeping on the couch. I was serious when I said I wasn’t having sex with you tonight.”
Jeff smiled. “Fair enough.” Jeff walked back over to the couch and picked up the sweats he’d been wearing, pulling them on before sitting down. “So, wanna order a pizza and watch a movie or something?”
“Jeff Winger being willing to have a nice little night in with a girl he just made out with? Okay, now I really might faint.” Annie laughed. “Pizza does sound nice.”
“What, I can’t have pizza and watch a movie with a good friend? Abed, Troy, and I had movie nights all the time last year.”
“Uh-huh. And did you make out with Troy and Abed first?” Annie snarked.
“Okay, Michelle and I would watch movies together all the time too.”
“Using your ex-girlfriend as an example doesn’t really help your argument, Jeff.”
“Okay, Annie,” Jeff replied defensively. “Maybe, I want to spend time with you. And maybe, I was hoping that if we watched a movie together, we might make out again later. Is that what you wanted to hear?”
Annie smiled. “Yep! Now, I’ll order the pizza if you want to pick out a movie!” She pulled out her phone and began dialing
“Fine.” Jeff went over to Annie’s DVD shelf and began to look through the selection. “Annie, do you have anything that doesn’t have Zac Efron in it?”
Annie put her hand over the mic of her phone. “I think I have a Clint Eastwood movie.”
“Annie, The Bridges of Madison County does not count as a Clint Eastwood movie.” Jeff continued looking through her DVDs, finally pulling out Indiana Jones and the Temple of Doom. “I would've preferred Raiders of the Lost Ark , but this'll do.” Jeff popped the disk out of the case and put it into the player. He and Annie sat down on the couch next to each other, and as the movie began, Annie snuggled in close to him.
About twenty minutes later, they heard a knock at the door. Annie hopped up and went to grab her purse, pulling out a few bills before heading to the door. She checked the peephole before opening the door, handing the pizza guy, a stoned-looking man with long, greasy hair, and a braided, mustacheless beard, the money. She took the pizza from him and quickly shut the door.
“That pizza guy was really creepy.” Annie set the pizza box down on the kitchen counter and opened the cupboard to get out plates.
“So you're saying he's a pizza guy?” Jeff laughed to himself. “Maybe we should introduce him to Britta.”
Annie walked back to the couch and handed Jeff a plate with a single slice of pizza on it. “Jeff!”
“Kidding! I'm kidding!” Jeff restarted the movie and began to eat his slice, picking the toppings off bit by bit. Once he'd finished, he set his plate on the floor and lay back on the couch, Annie leaning up against him. Not long after, Annie began to drift off, her head resting against his chest.
Once the movie finished, Jeff turned off the TV and carefully picked Annie up, carrying her over to the bed. He briefly debated trying to change her into some pajamas but worried about that being too far. Plus, he had no idea where her pajamas were, and didn't think it was a good idea to go rooting through her drawers again, lest he find another surprise. He tucked Annie in, and then double-checked the locks on the door before turning off the light and heading back to the couch. As he drifted off to sleep, Jeff wondered what would've happened if he'd gone to Rich's apartment instead of Annie's, as he’d originally planned.