Dipper and Wendy's four first times that went not the way they planned, and one that ended rather splendidly, which is coincidentally the one you wanted to read the most.
Their lips met for the first time when Dipper was fourteen. Unfortunately, Dipper could not remember it very well.
Dipper remembered floating on a mattress in a swimming pool. It must have been evening, or night, as it has been getting colder and darker every minute he spent in. He was desperate to find Wendy, or whoever else for the matter, but the borders of the pool were getting farther and farther away, the more he moved his arms. At some point he dived in, and then he needed to cough.
The cold water burned trough his lungs when Dipper finally got it out of his system. He heard his name spoken by at least three concerned voices, each of them calling his name in a different tone.
- Dipper, dude, are you there? - the first deep voice spoke, although it was clear it was far away, doing something else while calling him at the same time.
- Dipper, speak to us! - second disturbed voice rang in his ear, much closer and with much more grief and worry.
And finally, there was another voice, calm and steady but still filled with care and concern.
- Come on, Dipper, don't give up.
His eyes started to adapt to the dark place he was in and the blurry image became clearer and clearer. Dipper saw how a huge red blob turned into Wendy's hair and a radiant smile started forming on her face.
- You're alive!
The next thing he felt were two pair of arms tightening around his neck. He was still trying to catch his breath, as his memories were slowly going back.
Soos, Mabel and Wendy were sitting around crackling campfire, three pairs of eyes looking with relief at him.
- Guys... what happened? - he whispered, before noticing how cold he was. His clothes were drying near the fire, and with that, his memories started coming back.
He remembered an underground cave, a river, a glowing rune door, an enormous three-headed white kitty chasing them, a waterfall, Wendy's scream when he-
Wait.
His brain refused to process the amount of information, and Dipper collapsed for the second time.
When he awoke again, this time in the Shack, he was given full explanation on how they found an entrance to the legendary Purrgatory and how they had to escape its ferocious feline guardian. Mabel then told him how she came up with an idea to tie their ropes to make a ball of yarn, (which distracted it), and how Dipper fell into the river and had to be rescued by Wendy. The lumberjack's cheeks turned pink in response to Dipper's getting burning red.
- Dude, not the first, not the last time...
A few hours later, Dipper's head was still slightly spinning, and he kept asking Mabel about the details of the day whilst lying in his bed. There was something on his mind, as if a blank page that needed filling...
- Wait, Mabel, has something else happened in that cave?
His sister stopped reading her novel and smiled at him knowingly.
- Well... you know what happens when someone falls into the water, and has his lung full of it, and then needs to start breathing again...
- She did what? - he gasped, almost chocked on the tea he was drinking.
- Oh, Dipper, watch out, or we will have to call Wendy again! Or is this your plan all along...? - Mabel teased him, giggling under her nose.
He couldn't remember it. He tried, just like he did with all the other parts, but couldn't. The one thing he kept dreaming about for years has happened today, and he had no memory of it.
- Ma-Ma-Mabel, does that mean that we.. you know, kissed?
He turned around to meet his sister snickering and puckering her lips.
- "Oh, no, Mabel, I'm over Wendy, I moved on, I keep telling you". - she mocked him.
- Come on, Mabel, I'm serious. I mean, her lips were on mine, and mine were on hers, so, doesn't that technically mean-
Mabel shook her head, leafing through the pages of a massive sticker-filled book that found its way to her hands.
- According to the official Rulebook of Smooching - no. Unless you are a "princess, who has put herself in a thousand years sleep predicament through improper usage of sewing equipment".
Her brother looked at her agape, trying to collect his thoughts.
- Mabel, do you keep that book all the time? Wait, where do you keep it? Where did you get it? And for the matter, how come that there IS a smooching rulebook?
She let out a loud, almost ridiculing laughter, sat on his bed and put her arm around her brother's shoulders.
- Silly Dipper, you still have to learn so much about women.
Dipper was fifteen when he and Wendy went to their first date, although rather unknowingly.
Dating was the last thing on Dipper's mind when he was rushing through the rocky paths of the vast Gravity Falls forest. Not wanting to risk meeting with the ground at the astonishing speed they were riding, he clutched to the only material available, Wendy's shirt.
- You alright, there?
Her voice was barely audible, as the wind was wheezing around them. He was about to lie "Yes" to her, but then their ride had to bounce, making Dipper's stomach perform a move it was never supposed to do.
- Woah, easy there, buddy!
The mountain lion underneath them groaned in annoyance, but a quick poke of Wendy's boots to its sides brought it back under her control.
Dipper kept thinking if that was going to be the last day of their lives. True, the shopping basket tied around cougar's jaws provided some level of protection, but its claws were still formidable enough to make Dipper's hairs stand on his back. And there was, of course, the problem of ending their nightmarish, adrenaline-filled ride. At some point, the beast underneath them WILL have to get tired, presumably because of hunger. And preferable some time before that, they will have to-
- Dipper, we have to jump!
The fifteen year old boy registered a few images before landing on the ground. The first was that the vast forest has suddenly became much clearer, and his vision was no longer obscured by the multicoloured trees. He also recorded that the forest path they were running through suddenly became a mountainous one, leading towards the river's canyon. And the third thing was Wendy's voice, counting from "three" to "one" (skipping "two"), before they jumped from the lion, giving it enough boost to overdo the jump and fall into the water.
Wendy and Dipper leaned carefully, looking down the chasm, seeing how the big cat, soaked and freed from his makeshift harness was slowly and miserably walking towards its cave. They looked at each other briefly, before jumping in each other's arms, cheering loudly.
- Wendy, that was amazing!
- I know, right? Best date ever! Come on, let's find where we dropped the picnic basket.
The red-head was already on her legs, rushing down the road when Dipper fully understood the meaning of her words.
Dipper was sixteen when Wendy first admitted her love for him.
Dipper's laughter filled Wendy's room, even though he was sitting on his bed in Piedmont, miles away. Her new webcam happily transmitted her face to her friend, and Wendy soon joined Dipper, as they both remembered another adventure they shared no more than two weeks ago. His voice was much deeper than she remembered from the last year, but then again, most things about him have changed. He was noticeably taller, wearing slightly different clothes, and when he stepped out of the bus this year he was wearing some form of facial hair that could only be described as "Lost bet".
- Told you that we'll be laughing from it.
- Yeah, you were right, I was pretty silly.
He really wasn't, Wendy thought. His mind would naturally think about her first, it was a knee-jerk reaction. She saw him first as well, and as a result they were both ended up in trouble.
- So, what are you gonna do now?
- I dunno, read? - he answered. - I could start ploughing through the books...
- Dude, the first week's always free, it's normal. Relax. Now I got that sweet controller, I can actually kick your ass over the internet.
The brown-haired boy laughed nervously, politely refusing any fighting game sessions in the nearest future. His thumbs were still aching. The two spent the next few minutes or so joking and teasing, before Wendy finally broke it.
- Dipper... I want to thank you.
- For what?
"For being, you stupid dork."
- Everything, man! Every time you come here, something new always happens. You better be free on Halloween this year. I've got awesome ideas, it's gonna be amazing.
- Wouldn't be amazing without you.
Their connection was already lost when Wendy whispered "I love you" into her microphone. Then she had to sadly reply "no" to both Mabel and Melody, who worked overtime this summer to give her enough courage to admit that there was something more between her and Dipper. It would seem that this cruel twist of fate was too difficult even for Mabel, the matchmaker extraordinare.
Fortunately, later this week Wendy found out that shouting "I love you, Dipper!" is much easier if your virtual avatar is spewing fireballs at the person you are admitting love to. It also helps distracting your opponent enough to win more than a match.
Dipper was seventeen when he and Wendy landed in bed together.
Their movie night turned into a kissing galore as soon as they heard Manly Dan starting the family car. Wendy's father and brothers were leaving for a family reunion on the opposite part of the state, leaving Wendy behind, and as they thought - alone. The TV was still turned on, although their noises were easily muting the speakers.
Just a few weeks ago Dipper received permission to have his hands roam her back freely while kissing, and he was happily executing this right. Their tongues were locked and tangled, while their arms tightened around each other's bodies, following the wave of their heads movements. They never made out while lying on a bed, and Dipper tried to remain as restrained as possible, despite the fact that their legs started forming a complicated knot, trapping Dipper between hers. Immersed into each other, their heated bodies dug deeper into the sheets with each turn, closing the distance between the two.
And then Dipper's hips jerked forward.
An unexpected pressure in an area Dipper hasn't visited yet jolted her body, making Wendy loose the grip on his shoulders. Dipper immediately opened his eyes only to find Wendy's equally wide. Breaking the kiss, he jumped back and scooted clumsily to the other side of the bed, apologising profusely.
- We-Wendy, I'm sorry, I-I didn't want to-
- Relax, man. - she said calmly, though still surprised by Dipper's hungry and rapid move. - It's... it's normal.
He saw her eyes dart for a split of a second between his spread legs, showing clear evidence of his actions. Dipper turned around and did his best put his arousal under control. He sat on the edge of the bed, trying to catch breath after his accident. He was mentally preparing himself to stop calling Wendy his girlfriend after that, when he heard her again.
- Do you... wanna go on?
Her calm and slightly charming voice rang in his ears for another moment or two. He expected getting a punch in a face, or at least some verbal reprimand.
- I... I guess. If you want to. - was his only word he managed to stutter.
Her smile gave him enough confidence to continue, and soon the two teenagers entwined their bodies again and resumed the kissing session. Wendy tried being more cautious with her legs, as so was Dipper. If Wendy was careful, then Dipper was barely moving at all, tightening his muscles whenever he felt their bodies were too close to each other.
And then Dipper's stiffness touched her again, and Wendy decided not to lose him this time.
Their kiss broke soon and she heard a barely audible gasp escaping Dipper's lips when her leg wrapped around his bottom and her arms brought his weight on top of her. Her other leg swiftly jump-started Dipper's movements he was so valiantly trying to suppress. All she cared was to taste the alluring flavour of tightness and friction that escaped her a minute ago.
Dipper's breathing was erratic, to say the least. Trying to put some control in his actions, he managed to move his arms to support his body instead of falling on her chest. Some time ago he read lots of random sex-related do's and don't's on-line, and he remembered this one, as being particularly expected of him. Not that it mattered, as Wendy was much stronger than him, and soon his arms gave up.
Truth to be told, Dipper wasn't sure what he was doing, but he must have been been hitting every note perfectly, as parts of his name were constantly spilling from Wendy's mouth. He tried to react to her legs kicking and jolting by jerking his hips further and further. A spine-chilling moan escaped Wendy's mouth and gave Dipper enough courage to advance his frenzied moves. Their two bodies were moving clumsily in unison, making Dipper wish it could last forever.
It lasted about fifteen seconds, until Wendy tightened her legs around his waist even more forcefully and muffled her scream into Dipper's neck, giving him a sample of her jaw's strength. Air escaped his lungs in an erotic cry once more when she started shaking and writhing underneath him, as if she was having a fever. Her fingers grasped his shirt, and her leg kept kicking his involuntarily, as Wendy rocked him back and forth a couple of times.
The next minute Wendy started calming down and fell to the pillow beneath him, dragging Dipper with him. Her chest was rising and falling every second, but Dipper was more drawn to her reddened and heated face, brimming with joy he hasn't experienced yet.
- We-Wendy? Did you...
Dipper couldn't finish his question, as her arms and legs clamped around him again and made his lips join hers. Dipper not only could feel her heavy breathing but also hear her heart beating underneath him..
- Does that answer it?
Her seductive whisper was all he needed before he dived bravely in between her breasts, much to Wendy's excitement. They started tracing each other's body looking for buttons and zippers, while still hungrily mashing their lips together whenever possible. They had to stop briefly to take Dipper's shirt and once more when he put his hands under Wendy's bottom to grasp her jeans. She shrieked with delight when the sudden change in balance toppled her and made her fall into the pillows behind her, but quickly helped his boyfriend in getting rid of the piece of attire that burned her the most.
Dipper intended to take off her trousers with her panties in one go (as he saw in some other materials he remembered), but managed to only get rid of her jeans, leaving her legs spread wide open; her otherwise pristine white knickers had a distinctive wetter spot in the middle.
- Like what you did?
Dipper heard a scream trying to escape her throat when his thumb touched the same wetness he caused a moment before. Her hands worked hard to get rid of his undergarments, leaving Dipper in his briefs and with a rather large, clearly visible bulge. He jolted the same way she did before him, when her hand brushed the hardened tip, still hidden under material.
- Wendy, I-I don't think I'm gonna last very long...
- I don't care. - she replied quickly crawling her fingers inside his pants.
Dipper was overjoyed that he already made his girlfriend climax once, as he himself was dangerously close to his release. And he definitely did not want to disappoint her, so having the "orgasm balance" tipped in his favour definitely gave him more courage. At least until her palm found their way to his member, and made Dipper giddily repeat her name in shock.
And then Wendy stopped.
- Do you have a rubber?
For a while, Dipper could only hear his own deep breathing. Of course he didn't. He was prepared to spend evening making out with his girlfriend, but not to lose his virginity with her. His lack of response and a disappointed look of dismay on his face gave Wendy an answer. They started at each other longingly, their hands around each other sexes, ready to start exploring again.
- We... we could just do tha- he continued, but was cut by a kiss and a sharp "No".
- You want it, and I want it too. I've waited long enough. Go. - she answered throwing him his trousers back.
Never in his life Dipper got his jeans on so quickly, stumbling and tripping several times. Wendy was lounging on the bed, trying to get comfortable on an already slightly soaked sheets.
Five minutes later, Dipper rushed through the forest into the streets of Gravity Falls, looking for any nearby pharmacy. The roads were empty, sans a few roaring jeeps that took a sharp turn at the street corner. First two stores were already closed, but Dipper managed to find one open all night. He quickly walked into it, grabbed the tiny package from the shelf and proceeded to the checkout with money already in his hand, only to be greeted by a familiar soft, lisping voice.
- Good evening, Dipper. Having fun tonight?
- Candy? I-I never knew you work here.
The brunette was looking at him through slightly thicker glasses he remembered, but with familiar melody in her voice.
- Only at night, part time. Saw a lot of things there. Lots of medical experience. - she replied, adjusting her glasses - So, as I said, having fun?
He stared at her awkwardly, before finally snapping out.
- Uh, yeah... okay, listen, it's getting weird here. Here's the money, keep the change, that never happened!
Candy looked longingly as his chestnut hair disappeared swiftly into the night, ready to emerge in between Wendy's legs soon, as Candy thought. She ducked behind the counter and opened a bottle of salicylic alcohol.
- Hello, my old friend...
Dipper ran even faster this time, keeping the triple package close to his heart. He rushed to open the front door, only to find it being already open. The lights in the house were lit as well and he could hear much more noises he remembered. Dipper looked around, thinking for a moment he mistook the house, as he saw at least two more cars in front of it. Before he managed to land a single knock on the door, they were swung open by Wendy. However, the sight of his girlfriend, (who must have been awaiting his return) wasn't that strange, compared to what was happening behind her.
The lowest floor of her house was filled with at least fifteen very red-haired people in various age and shape, all wearing almost identical green plad pieces of clothing.
- Oh, hi, Dipper. - she started, trying to sound vaguely surprised by his appearance. - Uh, we... gotta cancel our night, I guess. I've got a family get-together, you see.
- But...
- Yeah, that's the one I told you about. See, funny story - she continued shutting him down and stretching her arms to cover the entrance, so that no one would see his face - We kinda got mixed up about the place, they thought that we were doing the meeting, and we thought they were doing it, and they kinda met half-way through, and...
- But...
- So, yeah, sorry for the mix-up.
She looked around her to see if anyone was listening to them.
- I'm really sorry. - she whispered, leaving her boyfriend agape. Last thing he saw before the door closed for good was discontent Wendy being flung into arms of some elderly woman.
Dipper tucked the condom into his pocket and started marching towards the Shack.
People of Gravity Falls would later tell stories about that frightful evening, saying that they heard soul-piercing howls of a lonely wolf amidst the moonlit night.
Dipper was still seventeen when he and Wendy made love for the first time.
Defeated and dilapidated Dipper Pines was lying arms spread on his bed, collecting his thoughts. Two hours ago he was denied the sweet taste of his girlfriend's sex, being cockblocked by her entire family, in all of their collective courduroyness.
Upon returning to the shack, he took a long and cold shower to cool himself down, up to no avail. He then tried solving su-dokus, until he realised that neither "W", "E", "N", "D" or "Y" are numbers. It didn't stop him from finishing the one he started. Sleeping was no option either, as the sheets were burning his skin and any position he tried made him imagine Wendy next to him, usually in various different combinations.
He couldn't even talk with anyone else about it. Mabel was spending this summer abroad, but even if she was sitting on a bed next to his, he couldn't just tell her about what happened. Or rather what didn't. And Dipper had a feeling she could read him so well, she'd known instantly what was going on. Yeah, she probably would. And she would make him wear a "I nearly got laid" sweater the next day.
Tomorrow. They will have chances tomorrow, he thought. It's not like they have two days of free time left. But still, he had almost a primal urge to be with her tonight, to finish what he has started.
He closed his eyes and imagine himself rushing to her house, getting through the plad-covered crowd, punching every single cousin, uncle and aunt in his way until he reached the door to her room, ready to take what's his.
Thump, thump.
He would knock, and she would open her door, her shirt, her buttons, her legs-
Thump, thump.
Dipper sharply opened his eyes. And then he heard her voice outside.
- Wendy?
His shaking girlfriend jumped into his arms the moment he opened Shack's door.
- I had to get out. - she whispered, waltzing with him towards the stairs, still trying to kiss him in between the steps - And I don't want you to sing any song for the next week.
They lost their shirts somewhere on the landing, and when their lips parted, Dipper finally managed to ask her.
- How did you get out?
- I told my great-grandma about it. And she said that if she didn't get laid once, then our house would be fuckin' empty.
Their tongues met again, but this time Dipper almost immediately backed off, feeling sour taste on her lips.
- Wait, are you drunk?
Dipper promised himself he would never do anything with her if she was inebriated. He would much rather spend a night alone, than risking breaking her trust the day after.
- Dipper, it takes more than alcohol to make a Courduroy drunk.
She planted yet another big sloppy kiss on his mouth and grabbed the edges of his shirt again.
- You make me drunk.
"Well, she was about to dry-hump me to death and she was sober", he thought getting back to returning the favour.
Dipper wasn't sure when Wendy lost her bra, but once he saw her ample and firm breasts, it was very easy for her to topple him to the bed. Once there, their hands begun to trace their bodies again, finding the same troublesome places they discovered before. Dipper's arousal became even more difficult to bare with, so he was relieved when Wendy's hands tucked his briefs down, freeing him and letting their wet sexes touch for the first time.
- You never took care of that?
He did, but it didn't help.
- Nah, I knew you're gonna come after me.
His quick reply gave him enough time to turn the situation around and pin Wendy's strong body to the bedsheets. They stared at each other for what seemed like eternity, both admiring their naked bodies. Dipper uttered her name only once, before she gave him a single nod.
Wendy, however, did not expect Dipper to understand her sign as an invitation for him to lift her back and put her legs on his shoulders. The sharp moan Dipper received in return for doing so was nothing compared to the cry that escaped Wendy's mouth when he smudged her lower lips with his tongue, tasting her sex. His nostrils met a new, strong, but not unpleasant smell. When his tongue darted over her glistening hole, it collected more than a few droplets of her fluid, a mix of her natural scent and some fragrant perfume she was wearing.
Dipper had very little idea what to do with Wendy's puffy lips, but it would seem his actions made his girlfriend spasm and grab the sheets of his bed regardless of how he used his tongue. If only he looked behind him, he would see Wendy's legs jittering in the same spastic, toes-curling fashion as before, this time being careful not to bump into his head or the slanted ceiling above them. Dipper could, however, hear her.
A single insistent and electrifying "Please" made Dipper understand her needs.
Soon Wendy's backside landed carefully on an extra pillow, and she made sure to secure her misbehaving boyfriend with her legs, arms and a series of smooches. She then felt a cold and alien feel of rubber touching the same opening Dipper was so glad to explore a minute ago.
Another inviting word whispered into Dipper's ears made him push forward, properly locking him with Wendy for the first time.
Then came their cries. And his apologies. And her kisses. And more of his apologies, followed by a single "Shut up, just do me!", and more kisses. More than enough to make Dipper buck forward, giving her more of him each time. Neither he nor Wendy were exactly comfortable with Dipper ramming through her with a condom on, but they would rather put up with the thin layer of latex being the only border between them, instead of making their house full too soon.
It would be difficult to understand what the two lovers were saying. They both kept repeating various syllables of each other's name, shortened, extended or distorted by their moans. Dipper was profusely asking Wendy if she was okay, always getting a soft confirmation and a kiss as an answer. Soon their fears and resistances were completely gone, and their combined voices sounded very much like different parts of a phrase "I love you", adjusted accordingly to the current combination of their entwined bodies.
With both of their bodies being already heated to the point of no return, it was no surprise that their love-making session came to an end as abruptly as it started. Dipper felt her body twitch and writhe at the same time when he felt his was showing a clear sign of incoming release. Ditching completely his gallant behaviour, Dipper grabbed Wendy's thighs and burrowed himself deeper and deeper, venting all of his urges, wishing for a moment there was nothing in between them so that he could fill her to the brim. The climax hit him earlier than hers, though it may have as well happened simultaneously; Dipper made sure to look into his girlfriend's wide open green eyes, before his spent, twitching body collapsed on top of her waving chest.
Neither of them knew how long they lasted. They both felt they finished too fast, but they were too tired, aching and groaning from their orgasms to complain. Dipper was (again) the first to start apologising for his sudden release, while Wendy was (again) comforting him, reminding that she was guilty of being ravenous as well.
Their sweated bodies kept flexing and convulsing for a few more minutes; Dipper's body jerked forward once or twice before he fully filled his condom. Wendy was adjusting hers to the young man towering over her, once more supporting his body on his arms next to hers. This time, their kisses were slow, savouring the moment and the taste of their victory against the obstacles life threw at them.
And that made Dipper even more perplexed when their lips parted and he heard Wendy laugh.
- W-Wendy? What's wrong? Did I do something wrong?
In response, she gave him one more kiss, after she stopped giggling.
- No, it's just... I've never seen a guy... You know, coming. And you looked...
- How? How did I look?
- Just like I imagined you would. - she whispered.
Dipper took another few breaths, before he replied, recovering from her arousing confession.
- You are not gonna laugh if your dad chops my head off for deflowering his little princess.
- Yeah, I'm gonna miss the tongue.
Wendy had very little time to defend herself when her boyfriend dived in between her breasts again, using his mouth exactly the way she wanted him to do. Sometime after that, a used condom fell to the ground, and a sharp sound of a plastic cover being ripped apart could be heard, but it quickly drowned in the wave of passionate moans of the two lovers and the constant creaking of their shared bed.
The clock on his bed-stand displayed one in the morning when now-eighteen year old Dipper Pines finally fell asleep next to his equally tired and content girlfriend.
Dipper woke up to the sound of water being flushed in the room down the corridor. The next thing that hit him was a wave of fresh air, dragging the heavy, warm and musky mixed scents of their lovemaking away, waking him up for good. The door were open, and Wendy was quite happily parading around his room in his red shirt that still looked comically oversized, even for her fit body. He noticed that the various pieces of clothing they lost last night were all dumped in one place on the ground, their messy state roughly corresponding to the way they probably looked like yesterday.
- Hi.
- Hi, honey. - Dipper replied before their shared a long and appetising kiss.
- "Honey?". I never noticed that we were married for twenty years. Or maybe we're in a sitcom?
- That would explain you wearing my shirt - Dipper replied, moving aside - It's like rule for a woman to wear guy's shirt after having sex, right?
- Well, I got your hat, so I thought I might start collecting a whole set. - she flirted, straddling him and planting another kiss, this time on his neck.
The sight of Wendy scattering a trail of kissed down his chest filled Dipper's heart with wicked sense of pride, so much so he had to control his breathing in order not to emit an embarrassing yelp in front of her. He couldn't restrain himself and discretely grabbed his phone from the table to take a picture of this most private moment.
But instead of Wendy's portrait he set as a background, he was greeted with a new Happy Birthday photo from his sister, showing a huge red sweater with words "I got laid" embroidered in ornament, green letters. And when Wendy finally closed her lips on him, Dipper was praying it was just a coincidence.