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What Could've Been...

He's in a different relationship now, but he can't help but wonder what his last one could have been
All through my senior year of high school, I dated a girl in the junior class. Sue was 5' 4" and I am 6' 2". I was still a virgin then and so was she. We swapped sexy nudes, sexted about our desires, you know, the works. But despite numerous occasions where I would find a dark back road towards the end of a date night, unbutton her top, unsnap her bra and feel up her nice C-cup breasts and small, perky nipples, and slip a hand down her panties and make her squirm, she never did put out.

Shortly after leaving for college, I broke off that relationship in favor of one with a much hotter girl. Rachel had perfect 38DD tits, a dirty mind, and a tight pussy. We fucked like rabbits in heat, with our record being eight times in ten hours. She's on the patch, which makes everything better; I can cum unprotected in her pussy all day long and never get her pregnant.

All of the above is true. Here's where it becomes fantasy.

Two weeks after coming home for summer break, I was lazing around the house, filling out scholarship applications for the next year and eating. I hadn't had any sex since the girlfriend went back to her home state, so each day consisted of typically two jack-off sessions.

That was when the text came in.

From Sue.

"Hey."

I wasn't sure what to say back, so I simply responded, "Hey" back.

"I have a question... but idk how to ask it..." the text read.

"Well," I replied, "just ask, I probably have an answer"

A few minutes went by before the next text came in: "do you still... think about me? ..."

"What do you mean?" I was confused.

Another few-minute pause. "u know... sexually?..."

I wasn't sure what to say. I loved Rachel to death, but to be honest, I had wondered from time to time how good Sue's lips would have felt around my cockhead, or how tight her then-virgin cunt would have been around my thick 7.5" shaft. I decided to play it kinda safe, but keep playing the game to see where it would go. "...sometimes..." was my response.

There was a ten minute break in between my reply and the next text Sue sent. It read, "...I think about u all the time."

Wow. I didn't know. How could I have known? I pondered on what she could possibly be thinking about, seeing as how she had never physically seen my cock, but then I remembered all the times that she had wrapped her petite little hand around the bulge in my Wranglers while we were making out, and all the nudes we had sent to each other. I texted back, "is that so?" and just before I hit send, I added, "...like what?"

She was fairly quick to reply, "I think about how big ur dick is and how good it would feel inside me... Brad, I want too fuck u..."

I was stunned. Here was this girl who, a year ago, refused to do anything more than let me touch her. Now, she's begging for my dick! I knew I shouldn't, but I couldn't help myself. "I want to fuck you too. What r you doin tonight?"

"After I get off work at 10, you."

Straight to the point. God, this is so wrong, but I let my curiosity and pure lust get the best of me. "You got it. I'll pick u up." Send. My brain had officially turned over control to my rock-hard dick.

The rest of the afternoon was filled with me talking to Sue, telling her I had to run to town to take care of a few things and grab a few groceries, that I'd be back later and I'd call her when I got home. At 9:30, I got into my truck and made my way into town, parking outside of her job, next to her truck. Around five after, she came walking out, noticed my truck, walked over and climbed in. We just kinda sat there for a moment, unsure of what to say to each other - what do you say in that situation? - until she finally turned to me and said, "Take us out to that old back road again."

That was all the motivation I needed. Letting my dick do the thinking again, I hit the key, dropped the truck into reverse, and backed out of the parking lot.

Minutes later, I pulled up to our old spot, miles out of town on an old dirt road that hardly anybody ever drove down. I killed the lights and shut off the truck. I turned my body and looked at her in the dim glow from the radio.

As I watched, she slowly reached down to her waist, grabbed hold of the hem of her t-shirt, and eased it up over her head. God, I had forgotten how petite yet perfect her little body was. She kicked off her shoes and let them fall to the floorboard as she scooted in and leaned towards me.

I did the same, leaning in and kissing her. The first kiss was just a brush of our lips, nervous and awkward; the next one, she locked her lips onto mine. Slightly startled, I jerked backwards a bit, but she stayed attached to my lips. I leaned backwards with my back against the door, and moved my right leg up til it was running along the back of the bench seat, and she was in between my thighs, lips still on mine.

Her left hand was on my right cheek, and her right hand made its way slowly up my thigh towards my rapidly hardening cock, until her little fingers had found the bulge in my jeans again. When her hand found it, she broke the kiss and let out a slight moan. She pulled back a bit and whispered, "Take off your shirt."

I did as I was told, pulling it over my head. Her right hand made its way up from my bulging jeans to run her fingertips over my abs.

"I forgot about these," she gasped, staring at their outline in the dim light.

She seemed to snap out of a trance after a moment. Looking back up at my face, she reached behind her and unclasped her bra and slowly slid the straps off of her shoulders, letting those perky C-cups loose. I watched as her nipples reacted to the cool night air, puffing up and getting hard.

All of a sudden, she leaned forward again and next thing I knew, my fly was unzipped and she was trying to pull my jeans down. I raised myself up a bit and she got my jeans down past my thighs. I kicked my boots off and they landed next to her shoes on the floorboard, followed quickly by my jeans and belt.

She paused just before she pulled my boxer briefs down, and as she pulled, my dick came with them. When it finally pulled free from the underwear, it slapped back hard against my abs, and her jaw dropped open. She stared at my hard dick for what seemed like a good couple minutes. Finally, she gently wrapped her hand around my shaft; she couldn't get her fingers all the way around. She moved her hand up and down a little before cautiously moving her head down to meet her hand.

She tenderly kissed my dick tip, and I let out a low moan. This must have given her a little more courage, as she took a little more of me into her mouth. Slowly, gradually, she eased her hot, wet, tight lips down around my thick cock. She could only take a little over half of it at a time, but she definitely made the best of what she had to work with.

After a few minutes of her mind-blowing blowjob, she pulled away with a loud pop. She unbuttoned her tight jean shorts, pushing both them and her panties down at the same time and kicking them off, letting them join the pile on the floorboard.

"Move down," she said, wanting me to position myself more towards the middle of the bench seat. I complied, positioning my cock in the middle of the bench.

She straddled me, with her right foot on the floor helping her prop herself up so that her pussy, which I could see dripping juices in the dim glow, was centered above my cock which she held in place with her right hand.

She looked me in the eye and said, "This is something I've been wanting to do for a long, long time..."

With that, she impaled her petite frame on my dick. She let out a moan of slight pain mixed with pure pleasure. Her pussy was so tight, it gripped my cock and didn't want to let go.

I grabbed hold of her waist and started to move her up and down, and she moaned louder. I let her go, allowing her to pick her own pace, and she started riding my cock.

"Fuck," she moaned, "you're even bigger than I ever imagined."

I just grinned and said, "you might want to hold on to something."

I grabbed her waist again and slammed my cock home inside her. Her eyes bugged out of her head and she let out a yelp of pleasure. I started pounding her pussy from underneath her, and she was moaning uncontrollably.

"I'm gonna cum!!!" she screamed, and I felt her cunt squeeze me harder than ever, but I just kept fucking her.

Her eyes rolled back in her head and she reveled in the orgasm I had just given her, but I wasn't done yet. I slammed myself home inside of her again, and shifted us around until she was underneath me on her back. I continued to relentlessly pound her tight little pussy as she clawed her surroundings, trying to grasp something. After another five or ten minutes of fucking her, I felt my balls start to swell.

"Fuck, I'm close," I grunted in between thrusts.

"Cum inside me! Cum in my tight pussy! Do it!" she screamed, and that was all it took. I unleashed rope after rope of my hot cum inside of her as she climaxed at the same time.

It took her a few minutes to regain enough composure to say anything.

"Th-th-that was... amazing..." she breathed... "You're so big, and you know just how to use it"

After another ten minutes, she finally got it together enough to get her clothes back on, and I took her back to her truck. "You know we're gonna have to do this again, right?" were her parting words.

I may regret it in the morning, but as of right now, I just had sex.

Thanks for reading! Hope you enjoyed it!
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