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Author’s Note: This, along with the other stories I will be posting are what-if scenarios with women that I could’ve had something with at some point, had I made different decisions.

Names have been changed to protect my own identity, and the identity of the young women portrayed here. This is a work of FICTION, and has not, and will never occur. Ever. As much as I would enjoy the opportunity, I know it is not my place to do so.

Enjoy :)

Xxx
It was a hot, scorching summer in the year of 2004. I was a fairly average high school graduate, with average friends, an average physique, and an average interest in the fairer sex.
I was fortunate, all things considered; had successful relationships, been in love, and thankfully was able to lose the V-card before graduation. Thankfully without the over-the-top shenanigans or erogenous use of pie.
As of late however, I had reconnected with an old family friend named Madison.

She lived with her mom, a single parent in a small apartment/townhouse complex not far from my own home. I knew her since she was a toddler, being babysat by my neighbors when we moved into the upper class neighborhood north of Chicago. She was just starting to mature into a beautiful young woman, one that had begun to catch my eye.

She had sparkling green-hazel eyes, medium length brunette hair; she was average height, a very slim yet athletic build. The budding development of firm A-cup sized breasts were just starting to form, I knew from seeing her as a young girl in the local pool that her areolas were small, with a neutral beige color and equally small nipples. I couldn’t help but feel a pinch of attraction to her physique, along with her tomboy persona. Both simply made her into a phenomenal young woman.

Now I was by no means a pedophile, I appreciated beauty, I knew that something’s just shouldn’t happen, and I rarely looked at young women like meat, even at the young age of 18. I knew in my heart that children shouldn’t be exposed to all the parts of an adult’s life, particularly sexual ones.
Madison seemed different, as I learned earlier that day.

I was out jogging with a friend of mine during the morning as part of my summer work-out routine, the one that I had been trained with while still in high school. I saw a biker coming down the path, I turned to my friend motioned him to take the grass on one side, while I took the other. As the rider came closer I felt vaguely off, almost like something was about to happen. As the biker got closer I saw Madison aboard, followed by her face lighting up as she started to wave.

I brought up my hand to wave back, but immediately saw something directly in her path. A coyote suddenly darted out in front of Madison, and stood frozen light a deer in headlights, completely unnoticed by Madison as she closed in.

In an instant I felt a blast of adrenaline surge through me as I sprinted, faster than I had ever done so before. Everything seemed to fade out of reality as my attention was focused on the two living beings ahead of me. At that moment Madison realized something was amiss and as she looked down she slammed into the eighty pound canine and was thrown clear off her bike.

Time seemed to slow down, much like in those Hollywood action movies as I closed on Madison’s now flying body.

20 feet

10 feet

5 feet

In the last second I threw myself airborne feet first and caught her in my arms. As my feet began to brush the ground I cradled her head in my arms and braced for impact. Said impact was far harder then I was expecting as I felt the wind get knocked out of me as both of us crashed into the ground and skidded briefly before stopping.

I shook my head to clear my disorientation to find Madison curled up in my arms, wimpering slightly. I ignored the now throbbing pain in my back and shoulders to run my fingers through her hair. She became silent instantly as she stirred, and looked up to find my smiling face mere inches from her own. Her face instantly reddened as I cupped her face with my right hand, “Are you okay Madison?”

“I-I-I-I t-t-think s-so Jeff,” she meekly replied. “Are you alright?”

I smiled, ignoring the pain, “Yeah, I’m doing just fine sweetheart.”

My friend’s footsteps loudly announced his arrival, “Are you okay man?! Those were some sick moves you pulled off back there!”

I smirked, “Put on a show didn’t I?”

“Dude, you nearly caused a traffic accident!”

I chuckled lightly, and turned to find Madison still on top of me, blushing furiously.

“I think it’s time to get up Madison.”

“Ah, yes!” She stumbled back onto her feet, still dizzy. I immediately got back up and steadied her with an arm around her shoulders.

I turned to my friend, “Head on home, I’ve got to get Madison back to her house.”

He nodded, “Take care man, I’ll text you later!”

As he walked away, Madison seemed to melt into my arms as she looked up at me, her eyes seemingly
glossed over.

Both of us walked for a few minutes in silence before Madison turned back to me, blushing madly, “I’m really glad you were there for me Jeff. I don’t know what I would’ve done if you hadn’t saved me.”

I looked down on the brunette, who was holding her arms slightly in front of her, poking her two index fingers together in a nervous fashion. I genuinely smiled, “I’m just glad you’re okay Madison.”

We continued in silence until we reached her townhouse, I was about to separate, but was shocked to find her arms wrapped around my waist.

“Madison, what’s wrong?”

The little girl’s eyes began to water, “I’m just really shaken up from earlier, you are alright, aren’t you Jeff?”
An in instant, I saw Madison not as a family friend, but as a woman. She was beautiful, and my cock began to instantly twitch in anticipation.

“Jeff?”

“What? Of course I’m fine Madison, couldn’t be better!” I mentally scolded myself for losing my focus and making an awkward situation even worse.

She giggled and very nearly sent my heart tumbling in my chest, “I’m glad to hear that Jeff, even if it took ten minutes to get that out of you. I’ll talk to you later, okay?”

I nod and smile, “Of course sweetheart. Bye!”

Xxx

As soon as I got home, I ran straight upstairs into my room, not stopping to talk to my parents for a second before closing my door, locking it, and stripping myself of all my clothing.

To say Madison had an effect on me was putting it quite mildly. As soon as my boxers came off my cock was at full mast, nearly seven inches long and three inches in diameter my tool was pulsating angrily, demanding attention. I went into my drawer where I keep my toys and pulled out my Fleshlight with a smirk, along with premium lube. I coated my still full sized cock and the fuck tunnel with the lube before ramming myself in to the hilt.

I grunt with exertion as a small spurt escaped my dick, likely waiting for the first chance to escape from me. I continued to stroke, attaching the Fleshlight with my purpose built missionary mount as I began to mechanically ram into the device. As my balls began to burn with an equal amount of fury and lust I began to lose control.

“God Madison,” I managed to gasp out as more and more spunk filled the base of my cock, “So tight!”
I could hear her in my thoughts, ‘Pump it all inside me Jeff! Fill me!’
At that moment I lost control and began to cum explosively, each stream not that different from a burst from a pressure washer. Each stream was nearly painful, it felt like my balls were being crushed as each impact filled more and more space within the Fleshlight.

My eyes exploded into stars as I fall over limp, my cock still spurting small streams as I briefly lost consciousness.

About two minutes later I pulled myself out and laid on top of the mount, gasping for air. After making sure I could still stand, I looked down and saw spunk easily pouring out of the Fleshlight’s pussy entrance, spoonfuls at a time. I carefully pulled the Fleshlight from the mount and quickly took it to the bathroom.

As I opened the bottom cap, a steady flow of spunk came from within, flowing into the toilet. At that final moment I realized that my previously nigh-unnoticeable balls were easily the size of baseballs now, along with cock with was nearly at full length, even though I was completely flaccid.

‘I’ll never be able to wear a condom again now, there ain’t a rubber in the world that could hold all this cum.’
Xxx

After cleaning up in the shower I sat down in my computer chair and pulled up my instant messenger, only to be surprised by a message from LoveKilla23

I can’t help but smirk, “Madison.”
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