Hindsight

I did my damnedest not to jump up and down, "Sure, I don't have anything going on tonight. I can come over—what time?"

He looked surprised, "Um, six? I'll get us a pizza for dinner—what kind do you like?" He was smiling now.

I couldn't help but return the grin as I watched him write down his address and phone number on a piece of paper, "I'll eat whatever."

"Cool," he said.

He kept stealing glances at me throughout the rest of the class. Occasionally I'd lean over and erase a word off of his homework when he used the wrong one. He was frustrated—but at himself because each time I did it, he smiled at me.

By the time the bell rang, I was counting down the seconds until 6 pm. I didn't see Jacob anywhere after school, so I packed up my bag and walked to the bus stop. Half way there, Brandon and Derek caught up to me. It was weird, but we started talking like we were old friends; they even sat by me on the bus. A few stops before they got off, Derek shifted awkwardly in his seat.

"Hey, can I have your phone number?" He blurted out, looking surprised afterwards like he didn't really think he'd do it.

"Um, sure?" I pulled a pen out of my bag and grabbed his arm, writing the number of my teen line on the back. He grinned like an idiot and they both waved before getting off of the bus.

It was almost four by the time I got home; Mom wouldn't be home for another hour and a half. I ran up to my room and dumped by bag by the door before kicking off my shoes and shutting my door. Two hours was a long time, but I knew exactly how I was going to pass it.

I stood in front of the mirror while I stripped, watching myself curiously as if I were watching a stranger, which I pretty much was because this body was amazing. When I slid my panties off, I turned and looked at my ass, bending over in half and glancing back at the exposed pussy in the mirror. I was glistening, wet from a day imagining my night with Timothy. I threw some pillows on the floor and laid back on them, watching the curious reflection spread her legs and bare it all to me. My skin was so smooth, so firm and these tits—god, they were heaven.

I watched myself run my hands over them, cupping and squeezing their weight. When I flicked my nipples, they started to harden. As soon as they were perked up, I rolled them in between my fingers, sending a shudder through the youthful body. With a light touch, I traced a path down my flat stomach and let my fingers run through the neatly trimmed bush.

Spreading my lower lips wide, I gazed at my cunt in the mirror, truly appreciating the beauty of the untouched flesh between my legs. I tilted my hips up some more, pressing my tip toes into the ground so I could spread my ass cheeks and see the tight pucker between them—yes, that part of me was still a virgin too. Well, in this eighteen year old body at least...it would be a few years before I took my first cock up the ass and oh god, how much I loved that when it was done right. Took a certain kind of man, though, a patient one who made sure to rub my clit at the same time so I enjoyed it, instead of just stuffing his dick in there without preparing me.

My fingers easily slipped through the wet lips; I used my left hand to splay them open, exposing the view of my clit. Biting down at my bottom lip in excitement, I teased myself, rubbing it slowly at first along the edges. I had to force my eyes to stay open, focused on the spectacle of watching this long forgotten body as if I were a voyeur watching a stranger. When my fingers started closing in on that bit of tender flesh, my breathing got heavy. I rubbed firmly in a circle, my ass clenching shut tight, my legs tensing—fuck, I wanted a cock bad. I moved my left hand down and slid a finger inside of my wet hole which actually caused me to wince—right, I was a virgin. Normally, by the time I was this ready to go I'd stuff three fingers in there and start fucking myself but right now, one would have to do. I slid it in and out, my other hand still working that tiny little clit faster and faster. I felt the build up, it was different from what I was used to. Working my body over, I sucked in a breath and held it until my legs started shaking and the orgasm hit me. My hips bucked upwards, grinding into my hands and I moaned out loud and low before crumpling down onto the carpet; my entire body was shaking and I could feel my cunt pulsing, the high of cumming rippling through me. Fuck, it was stronger than usual—when it occurred to me why, I laughed. Thirty eight year old me knocked one out solo every night before bed; in a way, I had built up an immunity to it. But this body, this young, svelte body didn't have much experience with masturbation. I know I tried it a few times but never actually got anywhere. Kinda hard to know what goal you're aiming for if you've never reached it before.

I laid on the floor for a long time, floating on that wave of bliss, trying to remain conscious because I knew I should go shower before Mom got home. Finally, when the phone rang, I forced myself to my feet and walked over to it while glancing at the time—it was almost five. The caller ID said Adams, Philip. God, he wasn't going to give up, was he?

"Hello?"

"Hello kitten," he said. "If you apologize, I'll take you back."

"Why the fuck would I want that, Colton?"

"Excuse me?"

I sighed, "Look, we had some fun but I'm not interested in you anymore. There are plenty of other fish in the sea, you're bound to find someone else."

"I can't fucking believe you, Cat. We were going to go to prom together, remember? That's next week. I already rented my tux and had it matched to your dress."

Oh, prom, right, "To my dress? My black dress, I'm assuming? Well, I'm sure you can find someone else to go with."

"I know I can," he said arrogantly, "it's you I'm worried about. You don't have any friends, remember?"

What the hell was I thinking dating this ass hat? "Please stop calling me, Colton. Good bye." I hung up the phone. Rolling my eyes, I hopped into the shower, ignoring the ringing when he called back four more times in the process of me getting ready.

In my closet, I looked at the black prom dress I had picked out—it was slutty. Slim fitting, thin straps, slit up the side, in fact I'm not sure why my Mom would let me walk out of the house in it. When I noticed the smaller bag near the bottom, I remembered the lace panties and matching bra that I had bought to go with it—prom was when I had decided I would lose my virginity to Colton. Of course, I didn't know at the time that he'd take me down a gravel road a week before, make out in the back seat and then grind against me until he was hard. He blamed me for it and said it was my responsibility to fix it because blue balls were painful. And stupid, desperate to meet someone's approval, eighteen year old me wiggled out of my black pants, stuck my ass up in the air like a dog and let him fuck me in the back seat of his shitty car. God, it was painful too, I was dry and not in the mood but I didn't want to disappoint him.

Sighing, I wiped the frown off of my face—not this time. Pulling out the lacy underwear, I slid it on my body and pranced in front of the mirror. Tonight, I was going to lose my virginity to Timothy Dane and I was going to fucking enjoy it. I put on my slim jeans, finding a dark blue, long sleeve button up shirt, which I left unbuttoned just enough so that my bra could almost be seen. Digging through my jewelry box I wasn't too thrilled about what I saw; I put some small studs in my ears, skipped a necklace and put a cheap copper ring on. I slipped on my chucks and grabbed my backpack when I heard the garage door open up downstairs.

Mom was standing in the kitchen when I got down there, "Hi Mom!"

"Hey sweetie," she said, giving me a hug.

When I pulled back I looked at her, "Did you—"

"Yes," she smiled, "I called and the doctor was able to see me today. They ran some tests and I'll know next week."

I was so happy, I started tearing up; when she saw me, she cupped my cheek before pulling me close, "Aw, honey, don't cry. I'm still here. You look nice—are you going out with Colton tonight?"

"Ugh," I said when I pulled back, "no I dumped him today. I'm actually going over to a friend's house to study Spanish—can I borrow the car?"

"Of course," she tossed me the keys before heading upstairs to change, "Be home by midnight, Catarina. I love you!"

"Love you too Mom!" I called up to her before I went into the garage and hopped into the car. I backed out of the drive way carefully and started towards Timothy Dane's house...yeah yeah, I didn't need to look at the address he wrote down because you bet I damn well knew where he lived. Maybe I casually walked by it a few times a week, maybe I didn't. Don't judge me.

When I pulled up to his house, I noticed two cars in the driveway—and realized that his parents were home. I was definitely disappointed, to say the least because I guarantee you that I wouldn't be quiet while losing my virgin and with adults in the house that meant it was a no go. A little deflated, I buttoned up my shirt to hide my bra and grabbed a light cotton jacket out of my bag. Swinging the backpack over my shoulder after locking the car, I walked up to the front door and rang the bell.

Mr. Dane opened the door—he looked surprised to see anyone, let alone me, not that he knew me, "Can I help you?"

"Hi, is Timothy home?"

He raised a brow and turned his head to call over his shoulder, "Timothy!" He stepped back and held the door open, motioning for me to come in.

When I did, I saw Mrs. Dane and she was dressed rather nicely—long red dress, high heels, diamond earrings and the like. I glanced at Mr. Dane and he was wearing a suit—they must be on their way out for the night. Woo!

"I'll be up in a minute!" Timothy called from downstairs.

"I don't believe we've met?" Mrs. Dane said, walking to me.

I waved awkwardly like I figured an eighteen year old girl would, "Hi, I'm Cat Fletcher. I go to school with Timothy—we are going to practice Spanish tonight."

"You're his study buddy?" Mr. Dane said, looking me over. It took me a second to realize what was happening—they were heading out the door for a date and Timothy told them a friend was coming over to study Spanish, but probably neglected to mention that I was an eighteen year old hottie who definitely wanted some dick from their son. Fuck—it was written all over Mr. Dane's face, I could tell, he was worried about leaving me alone with his son.

"Yup," I offered and shrugged my shoulders, "Timothy said if I helped him practice Spanish he'd teach me how to throw a football. It's the flag football unit in P.E. and I throw really bad. Like a girl, bad." I frowned before popping a smile back onto my face and casually slipping my hands into my pockets.

That seemed to ease his worries a little bit but I could see the hesitation in Mrs. Dane's face—certainly they didn't think I was the issue, maybe they didn't trust Timothy? I wracked my brain until I pulled up the memory—oh god, how could I forget...there was a rumor going around school that he and Angela fucked a month ago! I almost started laughing really hard too—I remember the next day she came to school she was limping around like someone shoved a car up her twat or something. I bit my lip, wondering if it was just failed sex, or if Timothy was hung...

"Maybe we should cancel," Mr. Dane said quietly to Mrs. Dane. I eyed them both.

"Why would you cancel your date? We're just going to be studying, you have nothing to worry about." When they looked at me, I let the smile fade off of my face, "Oh—you think—oh no, you think that...?" My eyes went wide. With my hand in my pocket I slipped the copper ring onto my ring finger before pulling it out and pointing at it, "I made a pledge to God, Mr. Dane. I will remain pure so that I can offer my future husband the ultimate gift on our wedding night." Right then Timothy came up the stairs and froze when he saw me.

Mr. and Mrs. Dane looked shocked. I could feel my face turning red in embarrassment which was just as well because it sold my story. Awkwardly I stuffed my hands back into my pants pockets and turned to Timothy, speaking in Spanish, "Hello Timothy, are you ready to study?"

"Ah, sure," he said glancing at his parents.

Mrs. Dane smiled and elbowed her husband before grabbing her coat and walking out the garage door, "Have a good time you two—nice to meet you Cat."

"You too Mrs. Dane!" I called after her.

Mr. Dane pulled some cash out of his wallet and walked over to his son. He handed it to him and said something stern before walking out as well. I watched their car pull out of the drive way before I breathed a sigh of relief and glanced at Timothy—he was staring at me skeptically.

"What?" I said.

"Nothing—I, ah, I didn't realize you were...you know, religious." He walked over to the couch and flopped down.

I unbuttoned the top three buttons of my shirt when his back was turned and followed him; I dropped my bag on the floor and sat down beside him, "I'm not."

"What? You told my parents—"

I laughed, "Yeah, they seemed to think that you would be studying with a guy."

He looked at me coyly, "I might have neglected to tell them you were a chick. They were going out tonight and I didn't think they'd be comfortable leaving me alone with a girl."

"Jesus," I said, "because you fucked Angela?" Angela and her eyebrows, that is.

He went wide eyed, "I didn't—I mean yeah, but—how do you? Did she tell you?"

"Do I look like I'm friends with her?" It came out more disgusted than I intended it, so I back peddled, "She was walking around like a cowboy for a few days, it was pretty obvious."

"Fuck," he said. His face started turning red and he stammered out the rest, "It was an accident."

"You...accidentally stuck your dick into her? Like, you tripped and fell and it just popped in?" I was trying really hard not to laugh at him; when he saw my face he started laughing too.

He ran his hand over his short hair, "Ugh, we were dry humping and it just kinda went in so we, you know."

I blinked a few times, "You know you're supposed to dry hump with your clothes on, right?"

"Well I do now," he shrugged.

Fuck, teenage boys are stupid. "Well there are going to be no accidents tonight," I said in smooth Spanish, "I'm going to fuck you until you can't see straight." When he stared blankly at me, I felt myself getting wet. God, he was hot. I lied in English, "I said let's go over the test materials first."

"Right, Spanish," he said very unenthusiastically. We grabbed our books and started studying; I quizzed him on a few things and discovered his main issue was with conjugating verbs. Yeah, I know you don't know what that is, because you read shit, not write it—be quiet and let me finish.

After about an hour he was getting a handle on the stuff he failed. He paused for a bit and I went to the bathroom while he ordered us pizza. When I was washing up, I kept staring at myself in the mirror, "You're really going to go through with this," I whispered to my reflection, "you're going to lose your virginity to Timothy Dane...fuck, he's hot, but...is this weird? I mean, you're like, thirty eight so...you're a cougar technically." I glanced down at my shirt and undid another button, starring at the perky tits alluded to by the cleavage, "Naw, this body is definitely not thirty eight."

When I got back out to the living room, Timothy was eyeing me while I sat down. I picked up my Spanish book and turned to him, "So should we go over this week's stuff?"

"Yeah," he said, tearing his gaze away from me, only to look back again, "You know, Cat, you are really easy to hang out with."

"Thanks?" I smirked.

"I mean, you are different than I thought you'd be. Before you were all quiet and I could never really figure out if you were scared or angry but now you're—you're like one of the guys, but you're not a guy, you're really...hot." I stared at him for a long time until he finally looked away, "I'm sorry, I shouldn't have said that."

I laughed, "You know I've had a crush on you since second grade, so..."

He looked surprised, "Really? No, I didn't...why didn't you ever say anything?"

I shrugged, "I wasn't very good at talking to anyone, let alone the hottest, most popular jock in school."

"So, what changed?" He seemed flattered by the compliment. I noticed that he, ever so slightly, started to lean closer to me.

"Hindsight," I said, my gaze locked on his delicious looking lips, "I finally realized that in twenty years, I didn't want to look back at this time in my life with regret."

He smiled, "Well, hopefully you won't regret tutoring me."

"I will if you fail," I snipped and closed the gap between us. My heart was pounding a million miles an hour when his lips touched mine—the self conscious part of me feared he would pull away...but he didn't. I rested my hand on his chest though honestly, I wanted to grab his cock right then. I parted my lips when his tongue prodded at me and let him into my mouth. The kiss was...it was...sigh, it was fucking awful. He was a horrible kisser, there was so much spit coming out of him and instead of teasing me with his tongue he shoved the whole thing in there and just left it because obviously he didn't have a fucking clue what to do with it either.

Thankfully, the door bell rang. He pulled back and sheepishly looked away before he paused, I noticed his cheeks getting red. He got up and walked to the front door and I wiped the pint of slobber off of my face. Well, that was a disappointment but it doesn't matter, because I want his cock and not his mouth, remember?

I followed him into the kitchen and he handed me a plate, "Do you want a soda?" He asked, though he still couldn't make eye contact.

"Sure," I shrugged and grabbed a few slices and put some on his plate for him.

We walked out into the living room and sat on the floor next to each other in pure fucking silence. Like, silence so thick that you could cut that shit with a dull plastic knife. Maybe even a spork. We were both on our second slices before he said, "I have a girlfriend."

"I realize that," I replied.

"I don't plan on breaking up with her," he mumbled to his piece of pizza.

Those eyebrows must have been plucked with dark magic, because for some reason that twig bitch had her claws hooked into him—whatever, I wasn't looking for a boyfriend. "So, you said I'm like one of the guys, right? That means I should just bluntly say whatever is on my mind?" I set my slice down on the plate and looked at him.

He looked nervous when he met my gaze—oh fuck, he probably thought I was one of those clingy girls. I suppose that makes sense because he was hella gorgeous so he always had chicks fawning over him. "Yeah," he replied.

All right, here goes nothing, "I'm not looking for a boyfriend, Timothy. I'm looking for...one night."

He blinked, "One night?"

OMFG teenage boys—how the hell did any of us lose our virginity to them? Seriously! "One night of sex. With you." His eyes got wide and his mouth dropped open. My resolve was starting to wane and I was beginning to lose my confidence, "Don't make this weird or anything, Timothy, I just want to lose my virginity to you, then we can go our separate ways."

I sat back and stared off at the wall—maybe I screwed this up, maybe I read him wrong and he really loved arched eyebrows. I was starting to get nervous and contemplated going to the drug store to buy some tweezers when he shifted awkwardly.

"I've only done it once before," he said nervously, "but...if you want to..."

"I do," I replied, oh fuck did I want to.

"Okay, so...how do you want to do this?" He set his plate down and turned his entire body to me.