Hindsight

I felt the shit eating grin cross my face again, "Well, first I'd like to give you a blowjob...then after you've recovered from that, maybe we can go to your room?" When I looked over, he was excited—of course he was excited, I mean, what eighteen year old guy would say no to putting his dick in a chick's mouth?

He started unbuttoning his jeans until I reached out and took his hands, stopping him, "Why don't you stand up?"

He eagerly got up and stood in front of me; he wiped his hands on his shirt. I tipped up onto my knees and looked into his eyes when I unbuttoned his pants. I hooked my fingers between the elastic of his boxers and his waist and slowly tugged them and his jeans down. When my gaze fell on his hard dick, I couldn't help but lick my lips—this was what I wanted. It wasn't bad, a little small like maybe six inches and not terribly thick; when I reached up and wrapped my tiny hand around it, I could circle it with my thumb and middle finger. But that's okay—I could work with this, as the adage goes, size doesn't matter it's what you do with it. That's true—well, for the most part, because sometimes you just want to have your cunt stretched by a nice fat cock or have a long one bottom out and poke your ovaries until you shoot eggs like a fish. At least with Timothy's cock, I could take it all in my mouth while still being upright.

I opened my lips and glanced up at him, maintaining eye contact when I took him into my mouth—the look on his face, let me tell you, was sheer awe. In one long, slow motion I took the entire thing in and felt the tip hit the back of my throat.

"Oh fuck!" He said, eyes wide with a huge grin on his face.

I closed my lips down on his shaft and pulled back, letting my tongue wiggle against the bottom before circling the tip. By the time I worked my way back down again, he was panting. I decided to give my signature move a whirl and left his entire cock in my mouth; then I started suckling, squeezing my lips in time with my tongue moving back and forth along the bottom. It was a good thing I was holding my breath because he came, hard. His hips bucked forward while he tried to shove his cock deeper into my mouth and his face crinkled up before he threw his head back. I reached up and grabbed his thighs to hold him still and keep him from pulling out because I didn't want cum all over my clothes. I choked it down—not my favorite thing to do, but in a pinch you just gotta swallow it.

When he finally started shaking and I thought his knees were going to buckle, I stopped sucking as hard and instead was gentle with his softening cock, lazily running my tongue over it while I pulled back until it finally popped out of my mouth. Timothy staggered backward a few steps and fell into the arm chair, staring intently at me.

"Holy shit, where did you learn how to do that?" He managed to get out in a complete sentence.

I tried not to laugh—I mean, that whole blow job took like maybe a minute—I figured teenage boys wouldn't have much lasting power but shit, was I glad I didn't waste my virginity to a zero to sixty seconds attempt at sex. "I ah," fuck, what was I going to say? I couldn't tell him the truth—that I had given many, many blow jobs over the twenty years since I graduated high school, "I read about it on the internet?"

"Wow," was all he managed to say.

I licked my lips and grinned at him as he pulled his boxers and pants up while still sitting, "So maybe in a little bit we can go to your room?"

"Whatever you want, Cat," he grinned at me.

I wanted it right then—I was dripping and ready to go, but I figured even a teenage boy would need like ten minutes to recover. I laid on my stomach on the floor, pulling my Spanish book up in front of me and raising my feet up into the air. I knew it looked sexy as hell and from his position he could see right down my shirt to my black bra. With a flirty gaze, I quizzed him on some more verbs. We barely made it to ten minutes before I could see his cock straining in his pants.

I shut my book and stood up, "Want to show me your room?"

He almost leapt out of the chair and led me downstairs to the basement; his room was a typical boy room, decked out in dark green and blue, plaid comforter, shit everywhere like a tornado went through it.

"Sorry," he mumbled, kicking clothes into a pile, "I didn't think we'd end up in here so it is a mess."

"I don't care," I said after taking my chucks off; standing before him, I started to unbutton my shirt which immediately got his attention. When I pulled it off and exposed my lacy black bra, his eyes were glued to my tits. I undid my pants and swayed my hips from side to side while I wiggled out of them, bending in half to pull them off and stood in front of him.

I intended to undress him but he was in such a hurry his shirt was ripped off over his head and his pants and boxers were gone and in a pile before I had a chance to make a move towards him—he was just as eager as I was. He came at me and reached up to touch my tits—but stopped. I saw the doubt in his eyes.

Without hesitation I swung my right hand up my back and unclasped the bra, letting it fall from my arms. I took his hands into mine and I brought them up to my breasts, guiding his fingers to cup them. He was almost giddy about it. After breaking the ice, I let him explore the mounds on his own; he fumbled with it, squeezing too hard, pressing them together, jiggling them slightly. It was kind of a turn off.

I realized then, that what I had imagined my first time being with Timothy was something more akin to a harlequin romance novel—that a handsome, rugged, buff, experienced man would sweep me off my feet and make love to me all throughout the night, the pain of my lost maidenhood soon forgotten in the throes of bliss. But this—this was not that. No, this was going to be some horny, inexperienced teenage boy blindly jabbing his dick around until it ended up in something close to a hole only to thrust three times and cum.

I took Timothy's hands off of my tits and turned him towards the bed, pushing him down onto it. I slid out of my panties and laid down next to him; he immediately rolled his body over mine, putting his knee between my legs to spread them. When his mouth came down on mine, I suffered through a few minutes of kissing until I felt him prodding his dick near my cunt; I pulled back and stopped him, "Timothy..."

The excitement on his face drained, "You...changed your mind...?"

"No," I said, "I want to be on top."

"Oh, okay," he quickly flopped over onto his back, his grin returned.

You bet your ass I wasn't going to let him top me—I wanted to cum and if he had control I'd blink and it would be over. I swung my leg over his waist and reached between us to take a hold of his dick; I swirled the tip of it against my wet cunt and I actually heard him moan. I positioned it in the opening and slowly pressed backwards. It was tight and I felt a burn of pain, but nothing like the first time I lost my virginity—I was so wet now, I was so fucking horny that by the time I impaled myself on him the pain was long forgotten.

I sat there on his dick and savored the moment I always wanted. Finally, I leaned forward, placed my hands on his bare chest for balance before I started to lift my ass up and drop it back down slowly. Timothy's hands found my hips and he squeezed the flesh gently; I gazed down into his eyes with a smirk. Half a dozen strokes and he said, "Fuck, Cat, I'm so close." I stopped immediately and he groaned, "Cat."

I reached back and grabbed his balls and pulled them downward gently; he gaped at me when I did that, "Yeah, well I'm not close. You're just here for the ride, remember?"

"Wh—what?"

I slowly started rocking again, "I've wanted this for a long time Timothy—don't screw it up for me. I am going to fuck you until I cum on your dick, then you can do whatever you want. Got it?"

The mixture of shock and need on his face didn't allow for him to respond, so he just laid there and took it. I continued moving, my tight pussy wrapped around that young hard dick; I felt the yearning building up inside of my core and I knew that it wouldn't take me much time but I drug it out as long as I could. I had to stop at least two more times and tug on his balls to keep him from cumming. My pace increased and I felt my breath get stuck in my lungs, my entire body tensed while I ground down on his cock; then, I felt that built up tension explode inside of me—it hit with such force I twitched and fell forward onto his chest. I closed my eyes and let the warm bliss permeate my body. I felt my cunt convulsing around his hot dick, grabbing it and kneading it.

Timothy's arms wrapped around my back and he held me, not moving while I laid there, panting against his neck. I knew he was waiting; I tilted up my head and whispered into his ear, "Fuck me. Hard."

He didn't hesitate; he kept his grip around my back but started pounding his cock into me, his hips raising both of us out of the bed. I groaned and grasped onto his shoulders when my second orgasm hit—not long after, I heard him moaning and he jammed his cock into me as far as he could, his body quaking when he came.

"Fuck," he said softly, "that was...amazing."

I laid on his chest, listening to his rapidly beating heart, "Yes, it was." I closed my eyes, my entire body pulsing with ecstasy.

...

When I opened my eyes, I saw it raining outside and I realized I was sitting on my porch. Ah fuck, I did really pass out and have a hangover dream. Son of a bitch!

I grabbed my phone and got up, walking through the front door of my house and froze. What the actual hell—everything was different. The furniture was expensive looking and not the old crap my mom had bought almost thirty years ago, the house itself looked like it had been remodeled and was decked to the nines.

I jumped when my phone rang, lifting it up I saw the caller ID, John Werner. Who the fuck is that, and how did his number get into my phone?

"Hello?" I answered, skeptically.

"O-M-G Cat! I just read the last five chapters and they are gold," he said that last word in a sing-song sort of way, his voice was slightly effeminate, "I know you are busy this weekend, but do you think you could get the next five to me by Wednesday? I am so excited! We're almost done!"

I had no clue what he was talking about; I closed my eyes and memories came pouring into my head—I graduated, Mom beat cancer, I went to college and holy fuck I was a writer! This dude was my agent! "Sure thing John, I can do that."

"You are such a peach, Cat. I gotta go—I'll talk to you Wednesday. Bye!"

I clicked the end call button on my phone; when I looked down, expecting to see the frumpy fat pants I usually wore, I saw a slim pair of leggings. Oh my god—I literally ran into the bathroom and started stripping to gawk at my naked self. My tits were big and perky, my stomach was flat, my ass had a nice curve to it and my legs were toned—I kept the body I had in high school. Touching my stomach I instantly remembered hours and hours spent at the gym, shopping at the organic grocery store, eating salads for dinner like a fucking adult.

A huge smile grew on my face; I grabbed my phone and tapped my way to the event invite: Yes...No...Maybe. Yes, definitely yes.

...

It took a while for everything to come back to me, but somehow I knew it all—my old life and my second chance. I finally made something of myself, I finished college, I was a fucking award winning author—I even called Mom and talked to her for almost an hour; she got remarried and moved down to Florida to retire.

I found this amazing black dress in my closet and a pair of sexy black high heels. I felt great when I left home, but the closer I got to the reunion I started to have doubts. I sat in my car outside the huge hotel that it was in. I was so fucking excited to go in there and strut my stuff, but now? I don't know, it is hard to explain it. My life was amazing and yet—I was still single. I never really found that one person I was meant to be with; I thumbed through the list of confirmed attendees and clicked on a few of their profiles—they were all still married with kids, stupidly posed family photos and tons of pictures out with friends. Yet mine—my profile was full of exotic landscapes from my travels, photos of me at book signings and posts promoting my newest novels. Not a single picture of me on a date or hanging out with friends or living a life outside of my career. I felt like I missed out on something both times I lived my life.

I got out of my car and put the keys in my clutch before walking inside. Somehow I almost felt more insecure now than I did in high school the first time. The conference room was converted into a makeshift club, the lights were low and a huge bar was set up on one side. I checked in at the table and got my name tag before deciding I would need a drink to get through this—then, I caught his gaze. Timothy flashed me that million dollar smile when I walked up to the bar.

"Tequila sour," I said to the bartender. While he mixed my drink, Timothy scooted over, resting with one arm on the bar.

"Catarina Fletcher, you're a sight for sore eyes."

I glanced over at him with a smirk, "Timothy Dane. How are you?"

"Better, now that you're here," he said, sliding into the seat.

I shook my head and sat down as well, "Aren't you here with your wife?"

He rolled his eyes, "Angela? Yeah, she's over with her group of has beens."

"Has beens," I laughed, "what's the matter, Timothy? Your life isn't the way you thought it'd be?"

He knocked back his whisky shot—I wondered how many he already had before he got here. His voice was low, quiet, "That's the understatement of the fucking year." Shooting me a sideways glance, he added, "You, on the other hand, have done quite well for yourself. And you've still got that banging body you had back in high school."

I thought back on it, sifting through the memories—yes, we fucked and he took my virginity and that was that, just as I thought it would be. Nothing ever became of Jacob and I, we went to prom together as friends but he moved east for college and never came back. Every now and then we'd email each other, but there hasn't been word from him in years. In fact, while I can recall many good relationships, none of them ever stuck. "Well," I shrugged, sipping my drink, "we'll always have Spanish class."

Timothy turned to me, lust in his eyes, "You know, you were the best I ever had, Cat. Wanna slip out for a bit? I can get us a room upstairs."

Fuck—seriously? Yes, I wanted to grind myself on that cock again. I wanted to leave him with another memory of what he missed out on during the past twenty years with Angela's eyebrows. But, somehow, I knew that one fleeting night of passion with him would only make me feel even more lonely in the end. I huffed a laugh, leaned forward and kissed him on the cheek, "Not in the cards, Timothy. Have a good night."

Rising, I got out of my seat; I could feel his eyes on my ass, on the way it swayed when I walked in heels. Good, I thought—always leave them wanting more. I walked out the door and into the somewhat quiet hallway—what was I doing here? I mean, sure, I had a great life now, I had my dream job, my Mom was still alive, I had a great body and wanted for almost nothing, but why was I here? To rub it into the faces of these sheeple? It occurred to me that I was doing the exact same thing they would have done to the old me—show up to the twentieth reunion so they could see how much of a failure their classmates' lives turned out to be, just to make themselves feel better. I sipped my drink and stood there, looking through the doors to the pulsing dance floor, seeing middle aged adults desperately cling onto what they once were instead of rejoicing in who they had become. No, if I learned one thing, it was that I stopped trying to make everyone else happy a long time ago. I knocked back my drink and set the empty glass on a table before turning around to leave.

"Hello, Cat." It was a voice I hadn't heard in a long time.

Just as I turned, my eyes fell on him—he was tall and slender, though not scrawny, not anymore. His light brown hair was swept back at an angle and his bright green eyes twinkled out from behind thick black glasses frames. He had the beginnings of a beard, more like scruff if a man didn't shave for a week. His hands were tucked into the pants of his navy three piece suit and when he walked towards me it was like a moving GQ cover. Fuck, he was drop dead gorgeous.

"Jacob?" I said it as a question, but I knew exactly who he was. Who would have thought?

His confident, gliding steps brought him forward. When his hands came out of his pockets, they immediately slid around my hips. He pulled me towards him and leaned down, never breaking his gaze. When his lips met mine I melted into his mouth, my entire body relaxing against him, against this handsome man who was once my friend. When he finally pulled away, I was breathless.

"I should have done that twenty years ago," he panted out, his eyes wandering over my face, his desire, his need for me finally as clear as day.

I knew, right then, that he was the one I missed out on, "Hindsight is a bitch, isn't it?"