It’s a funny feeling seeing everything go right all the ways it went wrong before. The night of 2014’s Winter Ball with Vanille (and her brother) was absolutely magical. We laughed, had fun, traded pokemon cards, even danced to the fun songs, all without feeling the need to take it further or create undue expectations. The experience itself was enough for me, and the little peck on the lips I got from Vanille as Viol pretended not to see for a moment sealed the deal.
 
It felt like ages since then, the whole time going in a big happy blur. There was nothing sexual about our relationship, just playing games and learning about each other. Viol slowly warmed up to me, permitted handholding and occasional kisses in the many activities he chaperoned (and took part in, of course). /d/ and /y/ kept saying he wanted in on it too, but he always denied it loudly and stormed off. I was just in my room drawing up some adventure plans for the Pokemon Tabletop Adventures game I was running for the Pallet twins, though I was getting ready to wind down for the night. I needed to come up with a better set of pokemon for their rivals because especially Viol would just completely obliterate them with his min-maxed poke-crew.
 
Well, I WAS winding down, until I got a knock at the door. “Come in.” I figured /co/nrad or /d/emona would want me to go to the bar with them and /ck/ or e/mlp/, so I kept at it, intent to stay focused while I turned them down.
 
“Hey Teej~” That wasn’t /co/ or /d/, that was…
 
“Vanille!” I hastily hid the paper’s I was drawing on and closed the game documents I had up on the screen. A little suspicious in retrospect, but she’s still precocious at her age, so I don’t want to give them a bigger advantage than they already have. “Didn’t think you’d be up this late.”
 
“Watcha’ do’n?” I could hear the door close behind her and light footfalls as Vanille moved up behind me.
 
“Aaaaah, nothing really, working on your adven-” I closed one of the documents and exposed an email from /d/ I forgot I had up: a big, high-res picture of some anthropomorphic pokemon getting getting tentaclefucked. Big fucking ahegao all over the screen. “-ture…” Just as quickly as it had come up, I closed it out, cussing under my breath. I dreaded turning around, but slowly I did, only to almost fall out of my chair.
 
“Oh my~” Vanille stood there, face somewhere between smug and aroused, fingers at her lips. “So you’re into that sort of thing. I guess I should have taken /d/emona’s jokes more seriously.” It took me longer than usual to absolve myself by blaming /d/, but Vanille was standing there in nothing but a skimpy pink silk teddy slip, these little low-leg string panties with (what else) a Teddiursa head printed on the front peeking out underneath, and of course, the usual pink thigh-high socks. Vanille picked up on my stare pretty fast. “W-what’s with the s-stares, Teej, you’re making me self-conscious~”
 
A thousand things rushed through my head faster than I could properly process them, complements, confusion, arousal, fear, desire I thought I bottled up, Willpower check to prevent heart attack roll… Pass. ‘Okay, /tg/, relax. You knew this day might come. Say something.’ Diplomacy check...  “Wow” I blurted. Smooth. Reeeeeaaaalll smooth. Least it wasn’t a crit failure.
 
Vanille grasped her cheeks with her hands and looked away bashfully. “C’mon, Teej, what’d I say about feeling self-conscious. You know what kinda courage I had to build up for tonight?” Physically, she hadn’t changed much since the ball way back then, still petite with a rather flat chest. Viol hasn’t fared much better, being the smallest kid his age on the block. Still, the teddy fell on some curves and she didn’t totally look like a kid in a sexy outfit (though why the hell did she choose those panties?).
 
Finally, words formed in my mouth and I was able to speak. “S-sorry, I’m just surprised is all. W-what’s the occasion?” Wasn’t an anniversary as far as I could tell, and Valentines day was months ago.
 
“Don’t tell me you forgot, you big dummy!” Uh-oh “T-to-today’s the day the 8th Generation pokemon games come out.” Shit, MORE pokemon names to remember? “S-so I’m… I’m 18 today.” Vanille’s eyes shifted from side to side and nervously intertwined her fingers. “S-so I thought, you might… might like to… be my f-first and j-j-jam it in!”
 
Well, by this point, my erection was threatening to tear my jeans, so I just got up and pulled her into a hug. Vanille gave off a small squeal of surprise as I brought her close and said “I’d be honored, my lady, to be granted such a privilage.” Slowly I pulled away and dropped to a knee, kissing the back her soft girly hand. “But are you sure you’ll have me?”
 
The swoon was so thick you could cut it with a d10 axe of Mood Cleaving. “Of course, Teej. All this time, playing and learning and hanging out, I really love you, ya know.” Vanille leaned down to where I kneeled and brought her lips to mine. Not the usual peck that Viol often carefully watched over (red as a beet, from jealousy or embarrassment I don’t know), but something longer and with tongue. For what felt like an eternity, we stood there, locked at the face, giving up the facade of platonics that we usually put up between each other. It was for the best. Yes, for the best, but now it doesn’t matter anymore, I no longer have to hold back.
 
One of us came up for air. I don’t remember which, but we stay there looking into each other’s eyes, and then back to it. I stood up, and a quick grapple check swept Vanille off her feet and brought us to the bed, tongues still intertwined. As I lay her down on the mattress, I began kissing down her body, in the nape of her neck normally covered by that scarf, down her chest, down the pokeball brooch of the slip, down her stomach, until I reached the matching low-leg lingerie that covered her slit, just every so slightly damp. I carefully peeled it away and found it all rather clean, a near imperceptible bit of stubble fit the edges. Seemed she cleaned up. “You’re getting wet already from this?” I teased a bit. The edges of her labia were starting to poke out from being engorged.
 
“I, *uhhh* I can’t help it. I was wearing this thing forever, *ahh* under my normal clothes,” Vanille tried explaining as I opened up her lips and began licking. “Ahh, I had to wait for Viol to, *uhhm* leave before  *ah* we could get some alone time. *ha*” Her moans and squeals escaped cutely as I focused on what I remembered from the last time I did this. Emprah, it’s been years.
 
“Just tell me whether or not you like what I’m doing,” I said as I tepidly inserted a finger into her hole to a slight squeal. It was wet, tight, and pulsing inside, practically sucking my finger in. My mouth moved up to Vanille’s clitorus, which was slowly poking out of its hood and her breathing grew heavier.
 
“Y-yes, *ah* y-y-*ha*-yes, there.” I wasn’t sure if it was working the clit or the finger that was getting sucked on by her hungry vagina, so I kept up with both. I could feel the edges of her hymen with my finger and was careful not to force it in there, though with how strong the walls of her pussy were contracting, that was easier said than done. She was probably coming close to climax, so I upped the ante and focused on her clit, her moans and gasps becoming more and more distinct, “It’s close, it’s close! *ah* *ha* *ha*” Gently, I chewed on her engorged clitorus and Vanille gave the most shuttering gasp yet and let it get caught in her throat as she spasmed. “*gasp* *ha*ha* It was *ha*ah* S-super*ah* effective”. and she went limp, breathing heavily, tongue hanging out of an open mouth.
 
“Y-you okay, Vanille? Vanille?” Did she faint? And I didn’t even finish? Well, I guess at least she had some fun. I can pop that cherry… as I thought to myself, her brooch rolled off and hit the floor, opening up her teddy and exposing her cute breasts. “Emprah on the Throne, why does she have to be so damned vulnerable right now,” I mumbled looking at her, and then at the uncompromising bulge in my boxers. “Well, only one way to take care of this now…” I got down and reached under my bed for the box that held all the usual monstergirl porn, or would have, if I didn’t notice that brooch had expanded and opened up as a pokeball.
 
I was now face to face with Tentaquil. Expecting, as had happened earlier on when Viol was still “testing” me, a face-full of blood puke, he just squawked, waddled over to Vanille, shoved a little leaf on her lolled out tongue, and hopped back into its pokeball. Before it was all over, Vanille popped right back up. “Oooo, bitter!” and then over to confused me and raging boner. “Oh, I didn’t faint did I?” She sheepishly sat up and felt herself up a little. “Man Teej, that really felt good. I’m sorry I passed out on you” She looked so cute like that, all disheveled and turned on, her teddy open and hanging limp at the sides. My boner grew three sizes that day, but it didn’t override my tact.
 
“Totally okay, seems you thought of everything anyway” I leaned in and kissed her while standing next to the bed, and I felt a couple of hands on my chest push me back. Surprised, I fell into my desk chair. Vanille hopped off the bed with a mischievous smile on her face.
 
“Well, since I fainted on you, I need to make it up, don’t I?” She got down on her knees and finally pulled my Hyperweapon from its sheath. Actually being confronted with my rock-hard cock seems like it put Vanille at a loss, but only for a second. Soon, a tepid hand reached over and started to caress it a little, waves of pleasure shooting up my spine from the touch. “Ah, it’s just as I thought…” Despite the moment of shock, she seems strangely familiar with it.
 
“So, uh, j-just how do you know what it looks like?”
 
Vanille suddenly got a bit defensive and looked away “Hehe, w-well, I’ve s-seen my b-brother’s, of… of course and I kinda, uh, *mumblemumblemumblemumble*”
 
“Sorry, what?”
 
“I asked my Sableye to take pictures of your dick while you slept.” She seems really embarassed to admit it, and while a certain level of terrifying, it was kinda cute to see her flustered. At least it sort of disturbingly explained all the wet dreams the last few weeks. Probably thinking I was a bit creeped out, Vanille grasped my shaft and looked up with pleading eyes, “I-I’m really sorry, Teej, I mean it, I-I was just scared that I wouldn’t be any good, since… you know, you have, uh, some real experience…”
 
I couldn’t help but laugh, “Haha, is that really all?” She looked up at me like I was making fun of her. I was, kind of, since it was just so hilariously innocent for a girl who’s all too fascinated with Pokemon mating. “I’m sure you’ll do great, Vanille. Just look how hard it got for you already.” I put my hand on her head and mussed up the loose strands a bit, and damn if you could blast away the thickest fog in CoC with that beaming.
 
She was also really good for a first time, or I was just so blueballed I forgot what good head felt like. Maybe she got those tips from /d/emona too. Didn’t matter too much, because I was enjoying it thoroughly, even if she wasn’t doing that thing with her tongue that… Nevermind. “Sho, hao an ai doin?” She peered straight up at me.
 
“P-pretty damn good if it’s your first time.”
 
She pulled off my cock for a moment, continuing to stroke it. “I-it is!” Vanille said earnestly. Clearing that up, “It’s, it’s not all that different than pokemon cocks. Sometimes I get a little wet thinking about what my pokemon are doing, see if a Ditto could turn into a, well, person, but I’m glad I didn’t try anything before you. It means a lot doing it with the person you love.”
 
That innocent, honest attitude is really what brought me to her too. “T-thanks, Vanille.” She went back to licking, now my balls as her hand went up and down my shaft already slick with her saliva. “I-I’m getting to the edge. k-keep it up.”
 
“No, not yet!” Vanille grabbed the base of my cock and clamped. “It would be a waste if…” She got up and back on the bed, lifting her legs and opening up her much damper pussy. “... we didn’t finish here.” She must have been playing with herself while she was sucking me off, the little succubus.
 
I got up and moved over to Vanille, open teddy now barely hanging on anymore, lining up my Hyperweapon into her fresh sheath. “You sure about this? No going back after this.”
 
She nodded nervously “I’ve never been more sure about anything Teej. I… I love you…”
 
“I… I love you too, Vanille.” Slowly, I guided myself in. Vanille squirmed a bit as she tried to relax herself so it was easier, but as I came up to her hymen and slowly pushed through, I felt the shivers run down her spine and her eyes water up. “A-are you okay? Do you want me to stop?”
 
“Hngn-No!” Vanille gasped. A small trickle of blood had begun leaking out. “K-keep going, I’ll be okay.” Easier said than done. She was tight as an Inquisitor’s asshole; it felt as though my dick was going to get crushed.
 
Somehow, I managed to get it in. “How you doing”
 
“I-I’m fine. It doesn’t hurt nearly as much anymore.” She said through some deep breathing.
 
“Alright, I’m going to move now, is that alright?” She nodded hastily, though not certainly. Carefully, very carefully, I began to pull out and could feel her shudder, and not necessarily from pain, and then back in again. It wasn’t very difficult to pace myself. Normally, I’d be worried after that oral I’d be done the moment I put it in, but Vanille was so tight it was even a bit uncomfortable for me. I continued to move, and as I did, she loosened up a little and started even having small squeals and moans of her own. Nothing near where it was when eating her out, but Vanille seemed to be getting used to it.
 
“Y-you can *ha* go a little *ha* faster if you like.” Vanille’s small breasts bounced with every thrust and I upped my pace. I leaned into her and began nuzzling the nape of her neck. Vanille responded by wrapping her arms around me. “I-it’s not *ah*ha* all gone, b-b-but I’m definitely f-feeling *uha* someth-thing,” she gasped into my ear. “K-keep going *ahn* Keep going”
 
I upped my pace as I brought my face out of Vanille’s nape to look her right in the face. When her eyes locked into mine, all the pain seemed to fade away, and I saw all the small subtleties of Vanille’s ecstasy. She took one of her hands from holding onto my back and brought it over to grasp one of mine, fingers intertwining. “*Hah* Intertwined? You’re such a *Hah* lewd girl, Vanille.”
 
“Just *ahn*ha* Just for y-you *uhn*, Teej *ha*ha*” I leaned in to kiss her, the sounds of our macking almost louder the the lewd sounds echoing from our nethers. After a series of light spasms within Vanille’s halls, I finally felt myself close to climax, and I think Vanille was too, though perhaps not as violent as the first one tonight. Before I could do anything I felt her legs lock around my waist, so what happened next I had nothing to do with. Deeply I came as the her vaginal walls contracted and fed greedily. I came up for air and we both gasped, feeling our mutual pleasures.
 
Vanille went limp again, but not fainted, so I pulled out and rolled onto the bed next to her, pulling her close. Viscous white liquid leaked out of her pussy and mixed with the modest amount of blood from the broken hymen. We lay there side by side, breathing heavily and naked, just enjoying the warmth of the other. After what felt like forever, Vanille slowly pried herself from my arms and started to crawl over to my lower half to start cleaning me up. “You know, not that I’m going to object to a round two, but I kinda don’t want a certain twin brother to burst in here and shank me.” Or worse, want to join in and stick it up my pooper. “Where did he go?”
 
“Oh that?” Vanille got me about halfway up and stopped. “I got /d/emona and a few of her NWS board friends to take him out for a midnight launch party.” Stone. Fucking. Cold.
 
Well, no use worrying about Viol’s chastity at this point. I lay back and put my arm over my eyes, grinning from ear to ear. “So I guess I’m not getting any sleep tonight, huh?”
 
A huskier voice than Vanille responded “Sableye?”
 
I woke with a start, and took my arm off from over my eyes. 4:08am, Wednesday October 29th, 2014. A cool breeze covers my nethers, as though I’m rocking out with my cock out. My eyes slowly adjust to the dim light. Two jem-like eyes and sharp white teeth hover over my half erect cock. Some foul beast is hanging over my junk with a...
 
A bright flash. Is that a Camera? Okay, whatever, this is not cool.
 
“AAAAAAAAAAAAAAAAAAAAAAAAAAAHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH"
 
I woke with a start, and took my arm off from over my eyes. 4:12am, Wednesday October 29th, 2014. Completely covered in my comfy wizard jammies wrapped up in my d20 sheet set. I see a form at the bottom of the bed… It’s just my Commander Fuklaw plush. I kick it off and hear it give its line (“DRIVE ME CLOSER, I WANT TO HIT IT WITH MY SWORD”).
 
“Fuck, this tension is really getting to me.”