Chapter 1

I had never thought the day I broke up with my girlfriend would be the day I was going to ask her to prom. Ashley and I, we were a perfect fit for each other. We both laughed at the same things, enjoyed the same food, and listened the same music. Even though she was a year older, we shared a bond like no other couple, always going out of our ways to cheer the other up or bring them little gifts just because. Some of my favorite times were seeing her face light up when I baked her cookies after a long week, or when I was waiting at school for her with a coffee in hand when she didn’t have time to get her morning fix.

Of course, there were the physical aspects too. Ashley was a beautiful, tall blonde. Her straight hair fell halfway down her back and her perfect smile, thanks to a few years of braces, lit up any room she walked into. And that’s not even the best part. Her eyes were chocolaty brown, and they always crinkled up in the cutest way when she laughed, which was often. But, Ashley looked even better undressed. Her ass wasn’t too big, and neither were her breasts, but that was just the way I liked it. They were a nice handful and her ass was perky and spankable. Her pussy was always shaved bare, dripping wet and waiting for my hard cock to slide into her moist depths. Sex with her was amazing; we were both each other’s firsts and it got better every time since. We both loved it. Or so I thought.

When she went off to college and I was stuck as a senior in high school, we promised each other we would try and see each other every other week, as her school wasn’t too far away. It was hard at first, but we established a routine, and everything seemed fine. Our sex life stayed pretty healthy, especially with Skype calls every few nights. When her roommate was out, Ashley would Skype me completely naked, her long slender legs stretched out on either side of her, showing her hot, sexy slit. I would reciprocate, leaving my cock in full view. A few minutes into the call, neither of us would be able to handle it, and she would slowly slide her hands down her body toward her pussy. Starting off with one finger, she would toy with her clit, moving it in slight circles as she started to moan and play with her erect nipple with the other hand. As my cock hardened, I would grasp it in my right hand and jerk my shaft with long, hard strokes. Ashley would progress to sliding two fingers into her dripping pussy and thrusting them in and out as her moans turned to screams that she had to muffle, or else her floormates would hear her through the thin walls. Her slickness would offer no resistance to her fingers, which would fly in and out at lightning speed. She would push them as deep as possible until she could reach her g-spot. Once she orgasmed, she would slide her sticky fingers out and give me the sexiest look possible. Only then would she bring her two fingers to her mouth and lick her juices off of them. Yes, Ashley was damn kinky.

I’ll always remember the last time we had sex. We were in her dorm, and I was pounding her from behind as she bent over her desk. She had been on birth control for a few months, so we were able to do it bareback. I thrust in and out of her velvety pussy, shoving my cock in as deep as it could go. At six and a half inches, I wasn’t huge, but I was more than enough to fill her tight hole to the brim. She especially liked it when I spanked her and sometimes, when I felt adventurous, I even slid a finger up her virgin anus (we hadn’t yet tried the back door) to give her extra pleasure. She thrust back against me, telling me to fuck her harder, and I could feel the familiar sensation building up that signaled I was about to blow, hard.

“I’m gonna cum, baby,” I grunted and grabbed her hips, slapping my groin against her ass cheeks.

“Me too,” she gasped. “Fuck me so hard.” I thrust faster and faster. My cock was a blur as it slid in and out of her hole at record speed. Ashley turned to me. “Fill me up, Derek.” The look of pure lust on her face was overbearing. With a long groan, I pulled her hips towards me and shoved my cock in as far as it could go as it spurt burst after burst of hot cum inside her. I felt Ashley tremble and her pussy tighten as she reached orgasm at the same time.

That was the last time we fucked. Two weeks after, I was hiding in her dorm room closet, waiting to jump out with balloons and a poster that said, “Prom?”. That’s when I heard the keys jingling, and a man’s voice outside. The door opened and two people burst it. From the slits in the closet door, I surveyed the scene with horror.

Ashley slammed the door closed and leapt on top of a huge, muscular guy who looked to be a few years older than her. He looked Italian, with close-cropped hair and a tattoo on his left bicep.

“Fuck my ass, Leo,” Ashley commanded, tearing off her yoga pants and black thong.

Fuck her what? My heart was pounding. I wanted to tear this guy to pieces, but something inside me made me stay put, wanting to see how far this was going to go.

Leo, if that was his name, shucked his pants in an instant. I expected to see a monster cock, but in fact it was pretty close to my own size. Leo picked Ashley up and placed her over her desk. She was bent over, exactly in the same position as she was during our final fuckfest.

Leo spread Ashley’s cheeks wide and dove in with obvious glee. The room was filled with sounds of him slurping at her asshole like a dog at a water bowl. Ashley started moaning.

“Oh yes, lick my dirty ass. You wanna fuck this ass, don’t you?” Leo said something, but an asshole on one’s tongue tends to hinder speech a bit and I couldn’t make out the exact words. If I had to guess, it was probably something like, “Yes, I want to fuck your cheating, whoring ass,” but of course without the cheating and whoring part.

Leo stood up and wiped his lips. Grabbing his cock, he lined it up with her asshole and slid in with no resistance. They had obviously done this before. I started shaking with fury from inside the closet. Anal wasn’t my biggest fantasy in the first place, so I wasn’t too disappointed that Ashley had expressed displeasure about the idea from the beginning. Looking at her now, who would’ve guessed? Leo was pounding her ass and reached around her to finger her clit. Ashley’s moans grew louder.

I had had enough. Quietly, I slid open the closet door and crept up behind the fucking couple. I waited a few seconds for the opportune moment and then, with all my might, kicked Leo in the balls.

You should have heard him howl. He leapt away from Ashley and shrieked, whipping his head around. Ashley turned just as quickly. Her hand flew to her mouth as she saw me standing there. Leo started rolling around on the floor, obviously in immense pain, but Ashley ignored him and stared at me, paralyzed in fear, waiting for me to say something.

I realized I was still holding the prom poster in my hand. “I would tell you to shove this up your ass,” I said. “But it looks like you’d enjoy it.” I eyed her gaping asshole.

Ashley unfroze and her eyes melted from ones of shock to ones of sorrow. “Baby, I’m sorry,” she moved over to me. “It was only this one time, I swear.” Leo was still rolling around on the floor.

Bullshit, I thought. Ashley took my hand.

“How can I make it up to you, baby?” She grabbed my cock through my pants and started to massage it. Unsurprisingly, I wasn’t really in the mood.

“Fuck you, Ashley,” I said, and walked out of the room, making sure to step on Leo as I exited.

On my way out of the building, I tossed the prom materials in the dumpster. No need for those anymore. As I drove home, thousands of thoughts raced through my head. It finally sunk it that that was it, it was over. Me and Ashley were through.

I pulled over to the shoulder of the highway. It was late, and no one else was around. Something inside me snapped I slammed my hand on the horn just for the hell of it.

“FUCK!” I yelled.

I pulled back onto the highway, but something had changed. I was overcome with emotion. No, I didn’t want revenge. That would come later. I wanted something more. Something that wasn’t Ashley.

I thought of all the girls (and even some guys) who had thrown themselves at me during the past ten months Ashley and I had been dating, but I rejected all of them because I wanted to stay faithful. Billions of wants and desires were now running through my mind, some that I didn’t even think were possible for me to want. I wasn’t the same person anymore, but I didn’t want to be. I wanted to be different.

This should be fun, I thought with a grin. And I headed home, to a new me, to a new life.

I was moving on.

To Be Continued…

**************

~The Doctor