Senior Year Memories Ch. 01

"Oh, fuck, come one!" she said, throwing her hands up in the air and walking back to her backpack. I was glad I held firm, glad that I saw through her act, but beginning to wonder if it wouldn't just be easier to talk to Mrs. Lynn about what a pain Kaitlyn was being and finding another student I could tutor.

I was about to tell Kaitlyn as much when she turned around and gave me an offer I didn't see coming.

"Fine, would you sign the form for a handjob?"

If it was impossible to pick my jaw off the floor, it was only because it hit with enough force to break through to the basement.

"What?" I asked.

"Look, I know you look at me like all the other boys do, so this has gotta be some kind of sick nerdy fantasy for you, right? Sign the form, and right here, right now, I'll give you a handjob," she said. Impressively, she was able to hide whatever disgust she might've had for jacking me off. She wasn't exactly enthusiastic, but I knew she was 100% serious.

I considered how much my morals meant to me and weighed that against this being the closest I'd ever been to losing my virginity, and in the end, the choice was clear.

"Handjob first," I said.

Disgruntled, but seeing an in, she said, "Fine."

"And can we at least go to my bedroom? I don't want my dad wandering in and catching us," I said.

"Sure," Kaitlyn said, leading the way back to my room as if it hadn't been years since she'd been here. She took a quick look around my room, at the movie and game posters, my shelves full of books, comics and figures, nodding softly as if this is exactly the sort of room she expected.

While she did this, I was doing everything in my power to convince myself this was actually happening, up to and including pinching myself to make sure I wasn't dreaming. I knew I wasn't, but, still, it was so fucking surreal I had to be sure. My swelling cock told me that it was real, though, and I was as ready to follow its instructions as ever.

I closed the door behind us turned to Kaitlyn, doing everything I could to keep my heart from jumping into my throat.

"So, uh, do I take my pants off here, or there, or which side do you want me to sit on?" I asked nervously.

"So you're a virgin, right?" she said.

"That obvious?" I asked.

"More obvious than that, actually. Just sit down here, unzip your pants and let's get this over with," Kaitlyn said, patting the bed beside her. Looking around, she quickly grabbed the box of tissues on my desk.

Nervously, I sat beside her, unbuckling my belt and unzipping my jeans, my briefs the only thing covering my now rock hard cock. I'd never been naked around a girl before, didn't know how she'd react when she finally saw, well, me.

Urgently, she pulled at the elastic of my underwear, pulling it down. "One great thing about virgins, at least, you don't usually last- HOLY SHIT!"

Now remember earlier when I said I had one thing that might've made me noteworthy if anybody knew about it? Yeah, I was talking about my cock. While I knew I wasn't much to look at, I knew I had a pretty impressive cock. Ten inches and almost as thick as a soda can, I was proud of it.

And now every inch of it was pointed up at Kaitlyn Pruitt, a bead of precum already formed on the tip.

She was at a clear lack of words as she looked at it. "I, uh... wow. Fuck, that's... wow. How is it exactly you've never, uh, had sex before?"

"Because I'd have to get a date first," I said.

"You don't need to go on a date to have sex," she said.

"No, but it helps to get to this step," I said.

"Huh," she said. "Makes sense."

Confidently, she reached out and took the head in her hand, rubbing it back and forth and smearing precum around. I groaned softly, my cock twitching at her touch.

"Fuck, I can't even get my hand all the way around it," she said, slowly jacking it up and down, taking agonizingly long to get from the head to the base. Her other hand cups my balls. "Fuck, even these are huge. I just can't believe it."

"Believe what?" I could barely ask as she started to pick up her pace, jacking me with one hand while her other fondled my balls.

"That this cock has gone completely untouched-"

"Not completely."

"Well, that I've never seen it. I mean, I like to think I'm a pretty accomplished slut, but I've never seen a cock this fucking big before," she said, jacking me even harder. I was in heaven as she used her "accomplished slut" skills to jack me better than I'd ever jacked myself before, twisting her hand delicately and applying just the right amount of pressure. I might've just come then and there at having one of the school's hottest and sluttiest cheerleaders jacking me off, if she hadn't kept talking.

"You know you could've gotten all the dates you wanted just waving this around at school, right? I mean, Regan Hills High is pretty much fucking slut central," Kaitlyn continued.

"It's... not... that... easy..." I croaked.

"No, it really is," she said. My cock was slick with precum now, and I knew I wouldn't last much longer.

Kaitlyn, her mouth watering, seemed to have other plans.

"Fuck it, I need this in my mouth, right now," she said, bobbing her head and taking the head of my cock in her mouth. I might've yelped with surprise, but she didn't let on that she cared, looking up into my eyes as her mouth stretched obscenely around the head of my cock.

Then, with practiced motion, she slid nearly half of its length into her mouth with one bob, then on the next getting it all the way down her throat. If I thought that her handjob skills were excellent, they had nothing on her blowjobs. Kaitlyn was a fucking blowjob artist, sliding up and down my shaft with a practiced grace. Coming up for air at one point, her her face was a mask of pure obscenity, tears streaking her makeup down her face, thick strands of saliva and precum connecting her perfect cocksucking lips to the head of my dick. Steadfastly, she caught her breath and then went back to swallowing my cock. I put my hand on the back of her head, running it through her hair and guiding her, and for once, she didn't have a bitchy response, groaning in kind as she went faster.

Coming up for air again, she said, "Tell me when you're gonna cum, alright?"

"Soon," I moaned, pulling her by her hair back to my cock. She took it back into her mouth, sucking harder and harder, slurping her tongue around the head.

I bucked my hips, grabbing her hair tight, "I'm cumming, I'm cumming, I'M CUMMING, FUCK!"

I thought she wanted to know so she could get out of its way, but she didn't, only sucking harder as I fired shot after shot of thick cum deep down her throat. I don't think I'd ever cum this much in my life before, and I don't think she was ready for it either, because after the first few heavy spurts, she gave up on swallowing and lifted her head from my cock. I wasn't done cumming, though, not by a long shot as more shots blasted across her lips, her face, her neck and even down onto her shirt. She continued to jack me, aiming as much as she could into her mouth, before I was finally spent.

I collapsed onto the bed, feeling like I'd just run a marathon. A marathon that ended with the biggest fucking orgasm I'd ever had instead of with me tired from running, but one that had me spent all the same.

I just had my very first blowjob. From Kaitlyn fucking Pruitt! And it was amazing.

On my back, staring at the ceiling, I started laughing at the insanity of it all.

"Fuck, that's a lot of cum," she said, running her fingers through the splashes on her face, collecting some of it up on her fingers and putting it into her mouth, sucking deeply. Her eyes lidded over as she swallowed more and more cum, her hand shaking with anticipation as she took each new drop. "God your cum tastes good. So thick..."

"Thanks?" I said.

"Yeah, you're fucking welcome. God, this cock is amazing. And I'm a fucking mess. Fuck, my shirt!" she exclaimed, finally looking down and seeing the mess I'd made across her tits.

"Sorry," I said, still beyond single words.

Kaitlyn got up from the bed, going for the door. "You guys haven't moved the laundry room, have you?"

"No," I said.

"Good, I need to clean this shit off before it sets in," she said. She disappeared down the hall, leaving me with my deflating cock lying back on the bed, staring at the ceiling and still wondering this was real. There was every chance that even if it was, that there was a cruel joke whose punchline had yet to be sprung, but right now, I was still bathing in the afterglow of having my cock sucked. No, of having my cock sucked by Kaitlyn Pruitt.

I told myself that this didn't make up for her years of cruelty, that deep down she was still the bitch she always was to me, but it was difficult not cutting her a little slack since, after all, that was a pretty fucking great blowjob. Fuck, even thinking about it started getting me hard again, my cock bobbing to life slowly. I'd have to sign her form since she more than held up her end of the bargain, but-

"No fucking way. You're hard, again?" Kaitlyn asked.

I got up on my elbows enough to see Kaitlyn standing in the doorway, missing her shirt and jacket and standing in front of me with only a black bra covering her massive tits. She'd cleaned her face, and... was it possible she's smiling?

"Is that something I say sorry for?" I asked.

"No. No it isn't. God, every guy I've been with is fucking useless after he cums. Jocks and players and every guy who thinks he's a piece of hot shit," she said, closing the door behind her. Steadily, she kicked off her boots.

"But you?" she continued. "A skinny little nerd, packing the biggest fucking cock I've ever seen, and it won't fucking go down? You're a miracle. You got a gift there that needs to be shared with the world. Before that, though, take off your shirt. "

"Why?" I asked.

"Because I'm gonna sit on your face, and it might get a little messy. I sucked your cock, and you better return the favor," she said, unbuckling her belt and sliding down her pants. She stood before me in only her bra and matching panties, the hottest woman I'd ever seen, and though I hadn't thought much about ever eating a girl's pussy, for her, I was eager to find out what it was like.

I listened to her, taking off my shirt. Nodding and biting her lip through a smile, Kaitlyn slid her panties to the floor. Her pussy, shaved bare and glistening with moisture, looked like the juiciest pussy I'd ever seen, way better than anything online.

Giggling, Kaitlyn pushed me back on the bed, climbing up next to me. On her knees beside my head, I got to see her throbbing pussy up close and personal, its lips engorged and parting slightly with anticipation. She was practically dripping and looked utterly delicious. I caught her scent, the musky, enticing odor, and I suddenly understood the appeal. I wanted my mouth on her pussy, and Kaitlyn was happy to deliver.

She straddled my head, kneeling onto my face as I tentatively stuck my tongue upward, licking at her dripping folds. If anything, the taste was even better than I imagined, sweet and tangy. I dove in, wrapping my arms around her thighs and pulling her onto my face, sticking my tongue deep into her as I ran it back and forth along her slit.

"Fuck, yes, eat that fucking cunt, eat it you little... fuck! Right there, forward more, find that clit, yeah, like that, like that, fucking fuck, devour my fucking cunt! Yes, yes, right there" she cried out, her voice getting progressively higher as I continued to dive in. Her thighs, weakening, started to give out, forcing more of her weight onto my face. I was starting to lose my breath, but she shifted her position just enough to let me breath, fully digging into her sopping cunt with my lips and tongue.

"You still got a lot to learn, but you've... OH FUCK, you've got enthusiasm, god, oh god, oh god, right there, yeah, god you've got enthusiasm, not like any of the guys here, god, I'm sorry I treated you like shit all these years, I'm sorry I tried to make you cheat, I'm sorry for everything I ever said to you, just, oh fuck, keep eating my tight little pussy, MAKE ME CUM YOU MOTHERFUCKER!" she screamed, grinding her cunt into my face.

I took her challenge and dove in with more ferocity, licking up and down, back and forth, forcing my tongue as deep into her as I could and rocking back and forth, fucking her with my tongue as she bucked and moaned. At one point, she rocked her hips so that her pussy was completely away from my mouth, and instead I was staring at her glorious ass, her cheeks spread apart, her tight little asshole winking at me as she flexed. On instinct, I dove in and started licking her asshole. It was a different taste, but not bad at all.

Her body went rigid, and she moaned even deeper, rocking her hips so I was able to really dig into her ass.

"Oh, fuck, you're dirty, aren't you, Ryan? Fuck, I never knew you were so dirty, I never knew, I wish I knew, fuck, fuck, fuck...

She looked over down at me, smiling and repositioning her pussy over my mouth. I returned to eating her out, licking wherever got the best reactions, whatever made her tense, or shudder, or coo and curse. After a while, she was beyond words, just grunting and groaning and growling like a beast, forcing her pussy onto my mouth until she finally screamed.

"FUCKING FUCK!"

A torrent of pussy juice gushed all over my face and mouth as she screamed, and with one great lurch her body started to shake. Her orgasm went on for what felt like hours from down here, but must have only been about a minute before she collapsed onto me.

We lay like this for a while, her face down on me upside down, licking, kissing my cock while I lazily lapped at her pussy. Finally regaining some of her strength, she rolled off of me, wobbling to her feet and pulling off my pants. From my vantage point, I wasn't in the mood to argue with her.

"You're just, fuck, you're, wow, I mean... wow... you still got some stuff to learn, but, wow. Thank you for rimming my ass; not a lot of guys will do that," Kaitlyn said as she bent over and grabbed my pants.

"Well, I'm not like other guys?" I said, trying to sound mysterious and cool and probably failing at sounding like either.

"No, you're not," she said, standing up, smiling broadly and carrying something.

"That my phone?" I asked.

"Yeah," she replied, tapping its screen a number of times.

"What's that for?" I asked.

"I thought a picture would be best to commemorate such an important occasion," she said, climbing back onto the bed beside me.

"What's the occasion?" I asked.

Reaching behind her back, she unclasped her bra, dropping it to the bed and revealing her tits to me for the first time. I'd imagined for a long time what they'd look like, and they did not disappoint, every bit as large and round and firm as I'd imagined, though my DD estimate was definitely on the low end. Her nipples had large brown areolas, all focusing on the firm nipples that pointed out at me like bullets. I knew what was going to happen, but even so, it was nice to hear.

"Today's the day I make a fucking man out of you," Kaitlyn said, straddling my hips so that her pussy was inches away from my cock. She rocked her hips teasingly, rolling the pussy lips against my shaft, coating me with her juices. She rested her cunt up against my cockhead, still teasing, rocking and rotating around, letting me feel her warmth and wetness but never letting me in.

"So, are you ready, Ryan? Are you ready to lose your virginity? Ready to see if that big, fat cock of yours'll fit in my tight little cunt? Think you're man enough to be a man?" she taunted, grinding her cunt up against me. The pleasure was agonizing, but I knew my answer.

The moment my cockhead pierced her lips again, I grabbed her hips and said, "Yes."

I pulled her, squealing, against me, forcing the head inside.

"Holy fuck!" I said, watching as my cock was now at least partially inside someone else. I'd done it, I was no longer a virgin. Her pussy was hot, wet, and so, so fucking tight. I knew she'd been around a lot, so I'd kinda thought she'd be loose, but, fuck, whatever cheerleading exercises she did must've made her so tight it almost hurt.

Almost. It felt like my cock was being squeezed by the most exquisite glove, her slight gyrations sending pulses of pleasure through the head.

There was the click of a camera as Kaitlyn took a selfie. Then, with sudden speed, she dropped down, burying my entire ten inches inside of her. If I thought I was in heaven with just the head in, then I must've been on some higher plane beyond heaven like this.

"FUUUUUUUUUUCK!" we both groaned out as we settled together. Then, once both of our heads cleared for a moment, we laughed at using the same word.

"Fuck, you're tight," I said.

"Fuck, you're big!" she said, raising her arm to take another picture of my cock now buried completely in her before she tossed my phone back on the floor. We stayed conjoined like that for a moment, both of us trying to figure out what exactly got us to this point, I think, before Kaitlyn silently began to move up and down. Her strokes were slow at first, taking only a few inches of me at a time, causing her to moan and whimper softly with every time my cock invaded her cunt.

She bent over, offering her nipples to me, and so lost in the moment of having sex with her, I didn't do anything at first. She swung her boobs back and forth, practically smacking me in the face with them before I remembered that, oh yeah, her tits I'd fantasized about for all these years were right in front of me, and opening my mouth, I took in one of her nipples. I sucked on it, nibbling slightly, licking at it, making her moan. I gave the same attention to her other breast, suckling at it like my life depended on it.

"You've got hands, too, you know," she said, grabbing mine and putting them on her ass. I squeezed and pulled at her, getting a good grip on her and forcing her down onto my cock as she bounced upward, our pace quickening as she started taking almost my entire cock with every bounce. I started fucking up into her, trying to match her pace, and though it took a little getting used to, I think I picked it up quickly enough.

"Yeah, fuck, you like fucking, huh, you take to it quick, really quick, fuck," Kaitlyn moaned.

"Thanks, oh god, I always, fuck, I always wanted to..."

"Everything you expected?" she asked, looking down at me with that arrogance I always hated, making my blood boil.

"Better," I grunted, grabbing her hips and flipping her over so I was now on top. She squealed as I found my rhythm, pounding into her harder and harder, her tight pussy gripping me tightly with each stroke.

"Fuck yeah! Fuck me, Ryan, fuck me with your giant fucking nerd cock, fuck me, fuck me harder, god yes, keep, FUUUUUCK!" she yelled.

If I fucked her any harder I was going to pass out from the pleasure and lack of breath, but I was so lost at that moment I was happy to risk it. Fucking Kaitlyn, letting out all my rage and frustration with her and letting it transform into pleasure, looking down at her as she moaned and groaned, getting pleasure like she'd never had before from a guy she'd shit on for so many years, it was a feeling of power I loved, and definitely didn't expect. It felt good to let go of that anger and just be lost in the moment, joined to her cock to cunt, just the two of us getting off together, lost in a see of sex and pleasure and loving every second of it.

Her eyes looking up at me don't show hate or disgust, but a real, genuine person lost in the moment, her smile a real smile. Without thinking, I kiss her, and she's kissing me back passionately, our tongues intertwined as we make out.

I start laughing as we kiss, and she stops. "What?"