Disclaimer: I don't own Community, yo
Written for the lovely lux_beata who asked me to write a fic with the following criteria:
- Annie's never had an orgasm and Britta spills the beans. Jeff decides to step in.
- Should happen in a bed, and be sweet and romantic.
- 'O' moment should be described from Annie's perspective.
Let Me
Jeff entered the study room to find only his female friends present, and Britta in mid-rant. He slid into his seat and cast a questioning look at Annie, while simultaneously trying to catch up on Britta's most recent cause du jour.
"...because this is what I do!" Britta exclaimed, gesturing wildly toward Troy's empty chair. "I push people away who want to take care of me and treat me with respect. I've done it with literally every nice guy I've ever met, and now I've done it to Troy too!"
"Hold up," Jeff interjected. "What happened with Troy? I thought things were going well."
"They were! They were going great, and then I had to go and ruin it by telling him that I didn't get the appeal of Blade Runner, and he just froze up, like I killed his puppy or something."
"Okay, I still don't understand. How is your not liking Blade Runner equal to you pushing him away?" Annie asked. Britta sighed deeply.
"Because I know Troy loves Blade Runner. I think I was subconsciously trying to create friction because things were going too well." She dropped her head in her hands.
"I don't think you have to worry Britta. It's okay for couples to have different tastes. Look at me and Andre. I love Cold Case Files and he likes Family Guy, so we record and watch them both together," Shirley attempted. Britta dropped her head onto the table with a groan.
"Shirley's right, Britta. I doubt Troy even cares that you don't like Blade Runner," said Jeff. Britta raised her head and levelled him with a glare.
"Oh, great, relationship advice from the king of commitment issues." Jeff rolled his eyes.
"If you didn't want my opinion why did you bring your relationship problems to me?"
"I didn't bring them to you, narcissist. I brought them to Annie and Shirley—which, really, I should have known better. I mean, look at us. I haven't had a healthy relationship since Blade, Shirley's re-married to the same guy who she divorced two years ago, Annie's never even had an orgasm..."
Annie let out a high-pitched squeak and Britta stopped short, suddenly realizing what she's said. She looked up at Annie, wide-eyed.
"Britta!" she exclaimed.
"Annie... I'm so sorry, I didn't mean to say that." Annie dropped her head in her hands, but not before Jeff could see the crimson blush taking over her features.
"Annie, it's not that bad... it's just us girls," said Shirley. "And... Jeff," she looked over at him, giving him the 'don't you get any ideas, heretic,' look. Jeff responded with a look of innocence, but only to try and veil the explosions going off in his brain.
Annie's never had an orgasm?
Holy crap!
Jeff looked over at Annie and found her face crimson red as she quickly packed her things in her school bag, despite the complaints of Britta and Shirley. With a withering glance in Jeff's direction, she bolted from her seat and raced out of the study room, leaving the group in her wake.
Jeff left the study room shortly after Annie did. He decided he needed to talk to her to help assuage her embarrassment at the word getting out about her... situation. Of course, he probably wasn't the best person to handle this—he was still blown away by this new knowledge, and didn't quite know what to make of it.
He found her laying on the couch in the student lounge, a pillow over her face. He sat down by her feet and caught her eye briefly as she peeked out to see who was there, before she pulled the cushion back down over her eyes.
"Go ahead," Annie mumbled from beneath the cushion.
"Go ahead and do what?" Jeff questioned. He grabbed the cushion and pulled it away, revealing her frowning face, still slightly tinged with a red flush.
"Go ahead and make fun of me. Just get it out of your system." His brow furrowed.
"Why would I make fun of you?" Annie pushed herself up into a seated position on the couch and tucked her legs underneath her.
"Oh, ha ha, Annie the unicorn has never had an orgasm. Laugh it up." Jeff bit back a small grin at her dismay.
"I wasn't going to make fun of you," he assured her.
"Oh great, so now I'm too pathetic to make fun of."
"No, it's just not funny." She fixed him with a glare. "Annie, it's not that big a deal. There are plenty of women who haven't... you know."
"Well, you would know," she teased. "With all of the women you sleep with, you've probably gathered enough evidence to run your own study on the subject." Jeff put up both of his hands.
"Woah, woah,woah. I didn't say the women I sleep with haven't had orgasms—of course they have. That's the Winger Guarantee." Annie rolled her eyes.
"Please. Some of them had to be faking it."
"Hey, I take offense to that. I may not put effort into anything else in my life, but I am no slouch in the bedroom. I work hard, and I make sure everyone leaves satisfied."
"Until the next day when they expect a phone call," she shot back, although her tone now belied her amusement. Despite her own humiliation at Britta's slip, it was always good fun to drive Jeff nuts. He just smirked back at her.
"Yea, well, my services are kind of a limited time offer. Besides, it's not my relationship skills coming under fire here."
"That's because you have no relationship skills to speak of." Jeff shifted uncomfortably in his seat.
"Hey, weren't we talking about your inability to get off?"
"Nice deflection."
"It's a knack," he threw back. He watched her shift around in her seat, clearly uncomfortable with him redirecting the conversation back to her. He would have felt bad, but she questioned his sexual aptitude, and for that he was happy to make her suffer just a little more. "So, you haven't... you know. Does that mean you're a virgin?" Annie groaned.
"Ugh, I do not want to talk about this with you." He smirked and nudged her.
"Hey, there's no shame in that. Sure, it means you're virtually untouchable by anyone who isn't a fetishist creep, but you're cute, so I'm sure you could find one to help you take the plunge." Annie glared at him.
"Not that it's any of your business, but I'm not a virgin. I just haven't been able to get there with anyone."
"Not Vaughan?" he asked, almost genuinely curious. Annie crossed her arms over her chest.
"I never slept with Vaughan. Whenever I tried to move things forward he called me a precious mountain flower and started singing self-penned folk songs about me." Jeff couldn't help but laugh out loud that that visual. Annie tried to be mad at him for it, but not even she could deny the inherent comedy of her relationship with Vaughan. "Shush, you," she said, giggling. "Has anyone ever called you a mountain flower and compared you to pure spring showers?" This just caused them both to laugh harder.
Once they both came down a little, Annie was feeling better. Somehow discussing this with Jeff was less embarrassing than it had been with Britta (who suggested various sex toys that Annie wasn't at all interested in sampling).
"Okay, okay, so if you didn't sleep with Vaughan, who did you sleep with?" Jeff asked after a little while. Annie told him the story of her first time with her high school boyfriend, doing it in his closet to the sounds of Madonna's Erotica. Jeff couldn't help a pang of sympathy for the poor woman who had clearly never been given a proper shot at an orgasm by anyone.
"Alright, but you know you don't have to actually sleep with somebody to get there... haven't you tried, you know... taking care of it yourself?" Annie's eyes widened.
"Jeff, are you asking me if I... masturbate?" she asked, saying the word 'masturbate' so low that Jeff wasn't even sure he heard her correctly. His cock, though, was quite sure—and it twitched when she said the word.
"Well, I mean... I'm just curious. You know a lot of women can't get off during sex, but they can in other ways." Annie bit the inside of her lip, contemplating whether or not to tell him. He didn't seem to be judging her too harshly for her inexperience, so she decided to throw caution to the wind and just talk to him about it. If there was anything Jeff could legitimately be called an expert in, the subject of sex would be it.
"I've tried it," she said timidly. "But I haven't been able to get there. Honestly, I'm starting to think it's just not going to happen for me." Jeff frowned.
"No way, you're definitely capable. You just haven't had the right motivation." Annie raised an eyebrow.
"And what motivation is it that you think I need?"
"Annie, look, there are lots of women who need a little extra work to get to that point. You need to try it with someone who is going to put in the effort to make sure you get there; someone who will jump through hoops to take you over the edge."
"Oh, is that all?" she asked. "And exactly who do you think would go to all of that effort for me?"
"I would," Jeff said quickly, obviously before thinking about his words. Annie looked at him, wide-eyed, her expression mirroring his own.
"Umm..."
"I mean, uh... geez. I didn't mean..."
"Jeff..."
"...well, I did, but I don't..."
"Jeff..."
"Because that would be..."
"Jeff!" Jeff stopped short. Annie offered him a slightly amused, slightly embarrassed smile in return. "Slip of the tongue. I get it. You didn't mean it." Jeff's brow furrowed.
"Yes I did." Her brow furrowed. "I mean, I didn't really meanto say it... but I definitely meant it."
"You did?" she asked, eyes wide and searching for signs of denial, or, you know, a stroke. Jeff squared his shoulders, thinking more about this.
"Yea, I mean... why wouldn't I? You're my friend. You're smart and beautiful and, you know... you're my friend."
"You said that already," she teased, trying to ease some of the tension, meanwhile feeling her heart fluttering incessantly in her chest.
"I did... and it's true. You're my friend, and I would do that for you. If you wanted. You don't have to want to. I understand if you..."
"I'll do it," Annie interrupted. Jeff stopped rambling and looked at her, surprised.
"You'll..."
"Do it," she repeated. "If you're offering—like really offering."
"I am," he said quickly. "I think."
"You can't think, you have to know. This isn't something you get to be unsure about." Jeff smirked.
"Isn't that what I'm supposed to be saying to you?" Annie chuckled.
"Yea, well, I'm not the one who's having a stroke here." He rolled his eyes.
"I am sure. I am... it's just a lot of pressure, you know?" She raised an eyebrow.
"I thought you had a 100% success rate—that's the Winger Guarantee." He glared at her, though a hint of amusement was present behind his eyes.
"I do have a 100% success rate. This is just a slightly different situation. You're my friend, not some random chick from a bar." Annie bit back a smirk.
"Don't tell me I make you nervous." He decided it was time to turn the tables back on her. She had gotten the upper hand way too easily. He plastered on his Winger smirk and leaned in a little closer.
"You make me feel lots of things, Annie Edison. But nervous is not one of them." He swooped forward and dropped a lingering kiss on her cheek before disappearing from the sofa, leaving a slightly stunned Annie in his wake.
She was going to sleep with Jeff Winger.
Holy crap.
Annie stood outside the door of Jeff's apartment. She'd raised and lowered her hand half a dozen times, never actually working up the nerve to knock. What would happen on the other side of that door? Would Jeff take her roughly, right there in the entryway? Would he nervously titter around and assure her that this was a one time thing and that it in no way entitled her to an actual relationship with him? Maybe he would fail to actually bring her to that ever-elusive climax and become weird and withdrawn around her for the rest of their time at Greendale.
Or maybe they would just have great sex, she would get off, and they would go on being friends, like always.
It was with that thought that she finally let her knuckles connect with the door, giving it three firm taps. Jeff was at the door within seconds, ushering her inside.
It was the first time she'd actually been inside Jeff's apartment. She looked around nervously. There was a broken lamp next to the door, a single sofa and a flat screen television. The walls were devoid of any real art, save for one piece that was so abstract not even Annie could pull meaning out of it. The walls were gray, and the floor was hardwood.
In short, it was as emotionally barren as Jeff pretended to be. What a perfect fit.
"How's it going?" Jeff asked, breaking the silence.
"Great!" Annie said, a little louder and faker than she'd rehearsed it. "How 'bout you?"
"Good, good," he responded. His hand rubbed the back of his neck nervously.
"We don't have to..." "You want to..."
They both chuckled nervously.
"This is silly. It's just us," Jeff said, dropping his hand from his neck. Annie nodded.
"Right, silly. Stupid even," she stumbled. She played with the sleeve of her jacket just to do something to ease her discomfort.
"Did you want some water or wine or something?" Jeff asked.
"I'm good," she responded. She and Jeff watched each other for a brief moment, before Jeff seemed to come to some sort of internal decision. In a swift movement, he stepped into her, flushing their bodies together and offering a small, genuine smile. He ran his hands down her arms, grabbing each of her hands and bringing them up with bended elbows, lacing their fingers together. Annie watched him intently as he guided their movements, curious about where this would lead.
"I'm glad you're here," he said softly. She smiled back a little shakily, unused to being so close to him. His body was long and hard against hers, and she felt small and fragile against him. His hands were so much larger than hers, and yet they held hers so delicately. She was taken aback by the tenderness in his eyes as he met her gaze.
"Me too," she choked out, her voice betraying her.
"You okay?" She nodded rapidly.
"I am, yeah. I'm just a little nervous."
"We don't have to do this if you don't want to," he reassured her. She shook her head.
"No, no, I want to. Can we just... can we take it slow?" Jeff placed a kiss on the back of one of her hands.
"We can go as slow as you want." He then leaned in and pressed his lips gently against hers—more gently than she was expecting. He pulled away after just a brief moment.
"Can you kiss me like that again?" Her voice sounded breathless to her own ears, which embarrassed her slightly. That embarrassment waned as Jeff smiled down at her and unthreaded their fingers, moving them to cup her face. She rested hers on his upper arms as he leaned in and kissed her softly once again. She held on a little tighter as her body began to react to the kiss. It was so much sweeter, so much purer than the others they'd shared. She almost wasn't sure what to do with it.
Jeff threaded one of his hands in her hair, gently holding her mouth to his while his other arm snaked around her waist. He opened his mouth and teased her lower lip with his tongue, barely dipping it inside as she opened for him. Annie sighed into him and relaxed against his body for the first time. It was mesmerizing, being held so gently by this mammoth man. She could feel each of her limbs responding one-by-one to the way he kissed her and moved with her. His large hand was splayed across her lower back, and her stomach was flush against his, and her breasts were pressed against him, and her hands were still grasping his arms, and his other hand was still gently cupping her head and guiding their kiss.
Annie realized at that moment that this was incredibly easy. Being lost in this moment was what she wanted, and it was almost impossible not to be.
She relaxed her grip on his arms and with open palms caressed his chest before looping her arms around his waist and pulling him closer. She felt no urgency, and was perfectly content to just live inside this kiss, this moment, for as long as she possibly could.
Jeff's tongue found Annie's and traced around the tip and underneath it, meeting it's smoothness with his own. She pressed back, tonguing the inside of his mouth and flicking along the roof, behind his teeth, learning his taste. They went back and forth like this for a few moments, all the while standing in the entryway. Idly, Annie wondered what would happen if they ever made it to the couch, or the bedroom for that matter. If he could drop her with a simple kiss at the door, what else was this man capable of doing to her?
Jeff moaned into Annie's mouth and brought her back to the present and the purpose for her visit. She could feel him hardening where she was pressed against him and was relieved to know that she wasn't alone in being affected by this kiss. She felt a surge of sexual power at feeling him hard against her, and decided it was time to up the ante.
Annie pulled away from the kiss and dipped her head forward, placing her lips against Jeff's shirt-covered chest. He allowed his fingers to brush through her hair a few times, still holding her tightly against him and not wanting to let go of her body heat.
She placed another kiss over his heart and turned her face up, meeting his gaze.
"Take me to bed?" she asked quietly, unwilling to disturb the heavy silence in the room. She noted that Jeff swallowed particularly hard before responding.
"Are you absolutely sure about this?" he asked again. She pulled away slightly and shrugged her jacket off, tossing it aside and slipping out of her flats.
"If you are." He hesitated another moment, before giving a nod that signalled some finality. He reached a hand out to her, which she accepted and allowed him to pull her into the depths of his apartment.
Jeff left her by the door of his bedroom as he wound his way around the bed to flick on the lamp beside it, casting a dull glow around the room. She waited patiently as he dug around in the drawer of his bedside table for something, and she was surprised when he pulled out two small candles and a condom, dropping each item on the table's surface. He pulled a lighter from the drawer and flicked on the flame, lighting both wicks before turning the lamp off again.
He turned back to Annie then, and she felt her breathing become a little heavier. With the room bathed in flickering candlelight, it made the whole scene feel oddly unreal to her. The angles of Jeff's face were well-pronounced beneath the orange hue, and she could see an ounce of hesitation as he hung back by the bed. Annie pushed the door closed behind her and leaned back against it, the sound of the latch the only noise in the room besides their breathing.
Encased in the small, dim room with Jeff, it finally, and for the first time, actually hit Annie that this was about the happen. No matter the reason or the motivation, she was about to sleep with Jeff Winger, and even though she wasn't 100% confident that she would actually experience her first real orgasm with him, she had to admit to herself that there was a definite possibility of that happening. She was already incredibly wet, and he'd only kissed her.
"Want to..." Annie gestured toward the bed, although her own body felt magnetically linked to the door. Jeff looked at the bed and then back at her, before crossing the room and meeting her by the door. This time, his kiss was far more hurried, far more passionate, far more like what Annie had expected the first time. She wrapped her arms tightly around his neck and pulled him down to her as far as she could while still maintaining as much body contact with him as possible.
Jeff pushed her back against the door and dipped his head down to her neck, ravishing it with attention. Annie clung to the back of his neck as he did so, dropping her head back and closing her eyes so she could fully appreciate the feeling of Jeff's mouth on her body.
This time, Jeff's hands didn't stay confined to PG areas. He allowed himself to feel her body in earnest, ghosting over each curve and crevice and taking full inventory of her shape. Annie moaned and did what she could to grind against him as his hands palmed her backside over her skirt. He pulled her toward him and allowed her to feel the full extent of the power she had over him, hard against her stomach. She pulled his mouth from her neck and devoured it with a hard kiss, desperate to have him in a way she'd never really experienced.
Jeff took this opportunity to unclasp the single button on her cardigan and push it off her shoulders. He moaned into her mouth as he caressed the bare skin of her arms, and once again reached down, grabbing both of her hands and bringing them up. This time, instead of gently threading their fingers together, he pinned her wrists to the door over her head and returned his lips to her neck, then her collarbone as she writhed against him.
"Too many clothes," he mumbled against her skin. Annie kept her arms raised over her head as his hands trailed down the silky skin of her arms, then down her sides, ghosting over her ribs before reaching the hemline of her shirt. He quickly pulled it over her head and deposited it on the ground with her cardigan, before stepping back to admire her fully in only her bra and skirt.
"Jesus, Annie," he groaned. "You're so beautiful." Annie's eyes met his, and she realized that he wasn't looking at her breasts or naked skin as he said this, he was watching her face. This new knowledge made her feel impossibly wet. She reached forward and took hold of the hem of his shirt and dispatched it as he had hers.
Jeff turned them around and walked Annie backward toward the bed. She climbed onto it and shimmied up to the top as he followed her on his hands and knees, hovering over her prone form once she had settled against the pillows. Annie allowed herself a moment to truly appreciate everything that Jeff was in that moment, with his defined torso made even more-so by the flickering light of the candles. She reached up tentatively and placed her palm over his chest, feeling his skin for the first time. Jeff gave her space to explore, watching her attentively as she become accustomed to his chest and abdomen. She didn't dare go lower, still hesitant and nervous to lead them to the next stage.
After a moment, Jeff settled down over her, resting on his forearms as he claimed her lips once again. He kissed her only briefly before heading downward, tracing his lips over her neck and collarbone, and then dipping lower to the swell of her breasts above the seam on her bra. Annie bit her lip and watched him as his lips danced lower and lower on her body, tongue tracing her nipples over her bra, before dipping down to her belly button and drawing a circle around it. She giggled at the way it tickled, and Jeff peeked up with a small grin.
"Ticklish?" he asked. She shook her head, but couldn't wipe the small smile off her face. He gave raised an eyebrow and dipped back down, circling her belly button again and making her laugh. "You're a liar," he mumbled against her skin. She laughed a little louder, feeling what was left of the tension in the room alleviate.
Jeff grinned against her skin and placed a small kiss over her belly button before continuing his journey south.
When he reached the waistband of her skirt, he bypassed the area entirely, much to Annie's chagrin. Instead, he skipped all the way down to her feet. He grabbed one leg and pressed his lips to her instep, causing her to giggle again. He sat back on his heels and rested her foot on his shoulder as he kissed the inside of her ankle, and then a little higher on her calf. He knelt down a little lower and pressed his lips to the inside of her knee, and then slightly higher on her thigh, before he had reached the hem of her skirt. He looked up and Annie met his gaze, offering a small smile.
Jeff reached up and tucked his fingers into the waistband of her skirt. She lifted her hips to allow him to pull it off of her, discarding it on the floor. He sat back and appraised her body, now clad only in her underwear (her matching, black, lacy underwear—a set she'd never had a reason to wear before). Annie felt herself flush at his appraisal, feeling wholly exposed laid out like this on his bed. He moved back to hover over her and kissed her gently.
"Absolutely beautiful," he mumbled against her lips. Annie breathed into the kiss, feeling a sense of relief wash over her. It wasn't that she was uncomfortable with her body, but it still felt good to have him compliment her. Especially him. Jeff had seen plenty of naked women in his time, so the fact that he would point out her beauty was more than a little flattering.
She tried to put all of those other women out of her head and focus on him as he once again kissed his way down her body. Once he was back on his knees, he reached out and grabbed her hand, pulling her up to meet him. As he kissed her, he unlatched her bra and pulled it away from her before guiding her back down to the pillows. Annie sighed into his mouth as he laid flush against her, feeling the skin of his chest against her naked breasts. It felt incredible.
Jeff pulled away again, and in a flash removed his jeans, leaving them on the floor with their ever-growing collection of discarded clothes. Annie could see his bulge beneath his tight, black boxer-briefs, and felt a surge of arousal course through her body. Believing he wanted her and actually seeing it were two different things. She was so distracted, in fact, by his partially revealed erection that she barely noticed him pulling her panties away. She felt the draft before she was consciously aware of being completely bare before him.
With one insistent hand on each knee, Jeff spread Annie's legs, fully revealing her to him. She felt herself grow warm in the candlelight, knowing there was no going back from this. She took a deep breath and let him open her up to him. She knew she could trust him to take care of her. He was Jeff. He was her friend.
Jeff offered her a small smile.
"How you feeling?" he asked.
"Good," she whispered. He knelt between her legs and rubbed her thighs with each hand.
"Good."
"How 'bout you?" she asked. He smiled widely and offered some version of the Winger smirk.
"Gorgeous, naked woman in my bed? Not feeling too terrible." Annie giggled and reached out for him to come to her, which he did willingly, reclaiming her lips in a soft, but needing kiss. Her legs wrapped around his waist as he ground his underwear-clad erection into her soaked centre, creating an entirely welcome friction. She silently thanked whatever manufacturer created the cotton-soy blend that made his underwear so soft and non-abrasive.
Jeff groaned into Annie's mouth before pulling away and retaking his now familiar journey down her body. He stopped to lavish each breast with ample attention, swirling his tongue around the small raised nubs and sucking lightly. Annie moaned at the feeling and ground up against his abdomen, now in line with her core.
This time, his journey took him to the place Annie wanted him most. Jeff settled himself in between her legs and offered a tentative flick of his tongue over her sensitive clit. Annie's eyes shot open at the new sensation and she gasped out loud. Jeff peeked up.
"Something new?" he questioned. Annie nodded and gasped again as he licked her once more.
"Ung, what is that?" she asked. Jeff leaned forward and put his mouth over her clit, sucking lightly. Annie's hands flew to her breasts and she dropped her legs open wide.
"Clit," Jeff responded, pulling away. He peeked up again. "Geez, no wonder you've never gotten off." He returned to the small nub and went about giving it the best attention he knew how, alternating between sucking, flicking, and long, languid strokes with the flat of his tongue. Annie wasn't aware that she could make the kinds of noises that were emitting from deep within her as he lavished her with attention.
She cried out as he brought his fingers into the mix. First one, buried deep inside of her, and then a second. Jeff combined his work on her clit with a come hither movement with his fingers, knowingly hitting both of the most potent spots within her. Annie's breaths came heavy as he went down on her, and she felt an unfamiliar tension growing and growing inside of her.
"Ung, Jeff," his name left her lips as a prayer, muttered over and over again: Jeff, Jeff, Jeff. She was so close, and even though she'd never experienced something like this before, she knew she was close.
Jeff decided it was well past time for Annie to finally go over the edge that had eluded her for so long. He redoubled his efforts and drew out her climax.
When it finally hit her, Annie's eyes slammed shut and her legs drew up to her chest, begging Jeff to get closer, harder, to fill her completely. Her cries came from the back of her throat in small puffs of air, which she gasped to reclaim. Her head hit the back of the pillow and her back arched, while her left hand fisted in the bed sheets and her right roughly grasped her breast. Jeff's hands sped within her, milking each contraction out of her.
As she came down from the height, her ears were ringing, and she could feel Jeff's smooth tongue dipping into her, lapping up everything she'd released.
When she opened her eyes, Jeff pulled away from her core and placed a soft kiss to the inside of one of her thighs, before moving back up to her. He wasn't sure if he should kiss her, knowing she'd probably never tasted herself before. His decision was made for him when Annie grabbed him by the back of the neck and attached her mouth to his, exploring his tongue and her taste. Jeff groaned against her, unable to stop from grinding into her spent core, desperate for his own release now that he'd successfully given her her own.
"Jeff," she mumbled against his mouth. He pulled back and created a small space between them. She focused her eyes on his and smiled. "Thanks," she said softly, a small blush creeping up onto her cheeks. Jeff grinned and leaned down to give her a peck on the lips.
"It was my pleasure." She smiled and kissed him again, and again, unable to stop now that she'd started.
"Will you do one more thing for me?" she asked after a moment. He grabbed hold of one of her hands and held it between them, stroking the back of it with his thumb.
"What's that?" She raised her eyes to his, a new wave of butterflies rising up in her gut.
"Make love to me?" Jeff hovered over her a moment longer, before a small smile formed on his lips. Without a word, he pulled himself away from her and pulled off his underwear before grabbing the condom from his bedside table and rolling it on. Annie watched, intrigued, as he went about doing so, not having actually seen a condom being put on before.
He returned to her quickly, settling himself between her legs and situating his tip against her slick opening.
"Ready?" he asked. Annie smiled at his never-ending concern for her. It was wholly unexpected, and incredibly charming. She nodded with a confident smile on her face, and wrapped her legs around his waist.
Without fanfare, Jeff pushed forward, filling her in one stroke. Annie bit her lip, and he allowed her a moment to adjust to his size within her, while also taking a second to keep from coming too quickly inside her tight warmth. He grabbed hold of her hand and threaded their fingers together again, resting it against the pillow next to her head as he began to move inside of her. He dipped his head into the crook of her neck and kissed the skin he found there as he finally made love to her the way he'd wanted to for so long.
The only sounds to be heard in the room were those of their breathing and the small slaps of skin as he filled her to the hilt with each downward stroke. It wasn't long before Annie felt that now familiar heat building inside of her, and hazily made note of the fact that she was about to experience her second orgasm on the very heels of her first. She wrapped her free hand around Jeff, palming his shoulder as he increased his speed inside of her. Between his thrusts and his heavy, staggered breathing in her ear, Annie couldn't help but fall as she was once again pushed over the edge.
Jeff pulled his face away from her neck as he felt her contracting around him, unwilling to miss the look of ecstasy on her features for a second time that night. He was painfully close to coming himself, but it was worth it to put it off and recite baseball statistics so he could view her beautiful release once again. Once she was gone, she watched him with heavy lids as he began to lose his composure and his pace became erratic. His eyes closed tightly as he flew over the edge, thrusting hard into her several times as he came with her name on his lips.
Unwilling to crush her petite frame beneath him, Jeff pulled himself to the side, discarding the condom into the waste bin he kept beside his bed. They each manoeuvred around the blankets, which Jeff pulled over them before they settled on their sides, facing each other with their hands clasped between them. Annie looked down at their entwined fingers before finding his face once again, smiling back at her.
"How are you feeling?" he asked softly. She smiled.
"Good," she responded. "Really good. Your record is safe." He chuckled and brought her hand to his lips, kissing it lightly.
"Thank God for that," he joked. They allowed themselves a moment of peace as they watched each other in the dim candlelight. The way the light bounced across his features made him seem almost unreal, and if she hadn't been touching him, Annie wasn't sure she'd believe any of this had actually happened.
"What now?" Jeff asked after a long moment. His smile was gone, replaced with a look of concentration. Annie shrugged, not wanting him to think she expected more than this.
"I don't know," she answered honestly. "This was just a one-time thing, right? A favour between friends?" Jeff raised an eyebrow.
"Is that all?" She bit the inside of her lip.
"Jeff, you know how I feel about you. Whatever this is, it will be up to you to define." He nodded.
"Then let's define it." Her brow furrowed. "Be with me, Annie. I want you, and I'm tired of pretending I don't." He pressed his lips to her hand once again, letting them linger there as he waited for a response. Slowly, a smile crept onto Annie's features.
"Are you sure?" she asked softly. He pulled his lips from her hand and settled them on hers.
"If you are," he said once they broke apart, mimicking her response from earlier in the evening. Annie smiled brilliantly and nodded. Jeff grinned and reached for her, pulling her into him and holding her tightly. Together, they fell asleep exhausted, spent, and entirely content.
When the group reconvened on Monday morning, Britta greeted Jeff and Annie with a smile.
"Well, Jeff. You were unprecedentedly right about me and Troy. Turns out he doesn't even care that I don't like Blade Runner—he was crying because someone tweeted a picture of a kitten and a puppy with a dialogue balloon that said, 'Best Friends.'"
"Hey, those were manly tears," Troy defended. Jeff struggled not to laugh at the younger, slightly overly emotional man.
"Well, I'm glad to hear you've finally accepted that I know more about everything than you do," he teased. Britta rolled her eyes.
"Whatever. Anyway, I wanted to thank you, and you too, Annie and Shirley. I appreciate you guys helping me down off that ledge... even if I did accidentally embarrass you in the process." She offered Annie an apologetic look. Annie waved it off.
"It's no problem, Britta. Actually, your little slip ended up working out in my favour," she said, smiling at Jeff. The pair had decided to be open with the group about their relationship, opting to get the hard part out of the way so they could enjoy each other fully. The five remaining study group members fixed the pair with confused looks.
"...what are you talking about?" Britta tentatively asked. Jeff looked between the Annie and the blond, gathering his nerves.
"Actually, Annie and I did some talking over the weekend, and we decided to give us a shot." He reached across the table and put his hand over Annie's. "We're together."
A chorus erupted around the table.
"Lord have mercy."
"Gay."
"Sweet, we can double date!"
"Cool. Cool, cool, cool."
"Really?"
Jeff focused on the last one. He turned to Britta.
"Really. We just... we like each other. We have for a while, and we want to be together." Britta looked between them hesitantly, landing on Annie.
"Annie?" she asked. Annie smiled encouragingly and nodded.
"He's been really good to me, Britta. You would be proud."
"C'mon, Britta. It'll be nice to have another couple in the group," Troy encouraged. Annie and Jeff both smiled at their friend before turning back to the blond. She hesitated a moment longer before finally resigning with a roll of her eyes.
"Alright, fine. Maybe you're kind of cute. Maybe." Annie squealed and jumped out of her seat, racing to Britta and encompassing her in a hug. "Okay, okay," Britta mumbled from beneath the other woman. "Still need to breathe, here." Annie grinned widely and extracted herself, but lingered next to Jeff with a hand on his shoulder. He wrapped one arm around her waist and met Britta's gaze.
"Just... you know. Treat her right, or else," she said to Jeff. He grinned.
"I will." He looked up at Annie and met her grin, both sighing with relief. With Britta on board, they both knew they could count on the rest of the group to take this well.
"Well, I supposed if Britta's alright with it," Shirley said, still eyeing the couple suspiciously.
"Shirley, you're the only one who really knows me," Jeff said, pointedly. "Trust me? Please?" Shirley rolled her eyes, but quirked a small smile.
"Alright, Winger. But you do anything to my girl here and Big Cheddar will come out to play." Jeff shuddered slightly.
"Scouts honour."
"Great!" Annie said from beside him. "So we're all cool?" she looked around the room.
"Hey, don't I get a vote?" Pierce chimed in.
"No!" six voices filled the small study room.
End
This was far longer than I planned, lol. Hope you liked it. Let me know!