A Long Prom Night Pt. 01

This is a true story about my date to the senior prom. Everyone involved in the story was over 18 at the time.

I had been dating Kass for a few months, but we were pretty serious right away. We both had a lot of things in common: music, TV shows, similar upbringings. To put it plainly, we were very attracted to each other. She had red velvet hair, a large chest and round ass.

Now, something that you should know is that Kass and I were both raised Catholic. Neither of our families were very strict or anything but in terms of intimacy, Kass and I were waiting for... marriage? a proposal? financial security in case we end up pregnant? I can't remember. But regardless, our attraction to each other often tested our will to wait.

We made small concessions as time went on. First, hand-stuff. We needed a way to make each other cum, and its not like we didn't masturbate! So what's so wrong with having my loving partner do, what I would already be doing myself?! And it was incredible. She was pretty inexperienced when it came to sex. We both were, but I had two partners before Kass and I got together. Which means not only did I feel like a Sex God when I would to be able to find her gspot and feel her pulsating around my fingers, but also she learned to pleasure me, from me. She loved turning me on, and doing everything to push my buttons.

So then came the mouth-stuff. Kass prided herself on swallowing cum. She loved to push her limits, cause she knew how much it turned me on. She loved to open her throat and want me to use her mouth as any other hole. Looking back, I think its because she knew she wanted me to fuck her, and this was as close as we got. She loved to look up at me while deepthroating my, don't mean to brag but-, rather impressive cock. This would obviously cause me to cum my brains out and then she'd swallow again.

But prom was gonna be different.

After all our extremely frequent blowing, licking, handjobs and finger blasts, we were gonna take the next logical step...anal.

Like I said, we were half Catholic and so we thought, we are still technically following the "rules".

Our first time wasn't after Prom however. Still, I can remember it clear as day in my mind. No, the first time was on my bed some weekend afternoon. We were spooning and her perfect ass was rubbing against my corduroy erection. I reached my hand into her blue jeans, sliding beneath the button fly to her cotton panties. I circled her clit through the fabric, this caused her to push her ass further against my swollen pillar. She moaned. I grunted. She knew exactly what she was doing, revving me up again.

She whispered "I want you inside me". I almost snuck my fingers under her panties to slide inside her wet tight pussy. I don't know what came over me though, maybe all the animalistic grinding and growling, but I instead brought my hand around to the back. My hand and outspread fingers were cradling the middle of her ass. My middle finger was settled in the crack, only leaving a piece of cloth between my finger and her virgin asshole.

"Is this ok?" I asked. I then softly applied pressure to her hole with my finger. She seemed baffled, truthfully I don't she had ever considered it. She backed up against me again, escalating the contact between us.

Eventually, I slid my hand down the back of her panties and made true contact with the tight hole. I massaged it, and eventually, bit by bit, penetrated her ass. She moaned, I was in awe. Was this really happening?

Soon, she was on her back and I was licking her pussy and using my pointer finger to find her spot, like we usually do. This time though, I also slid my middle finger back to it's forbidden home. She moaned and bit a pillow. She grasped the bedsheets. I could feel her pulsating around my pointer finger, and feeling her hips push back to continue getting assfucked by middle finger.

After a brief intermission where we got some supplies from the store, Kath and I were back at it. This time slowly adding more fingers to her ass, she always liked the challenge. She wanted to use her ass like she assumed the other girls used their pussies.

I was harder then concrete, and given my size, I knew even with our effort it would be hard work. She was bent over my bed, light blue panties around one ankle. Her beautiful ass was presented to my hungry cock. I grabbed her left hip with one hand, and my dick with the other.

Slowly, I pressed the tip of my penis against the soft tissue of her asshole. At this point, we had worked her ass open a little, but it still seemed rather tight. As I pushed gently into her, I could see her toes curl into the carpet.

"Relax. Just let me know if you need me to stop or slow down"

"It feels so big" She said incredulously. "Go slow"

I softly thrust a little deeper into her anus and then pull back a little. She would take a breath. I pushed my cock a little deeper, slide back a bit, breathe. Centimeter by centimeter my large cock excavated her asshole. She gripped the bed and the arched her back into me, forcing my cock deeper inside her ass. I moaned. It felt incredible, like the tightest, warmest, handjob mixed with the dirtiest fantasy you've ever had.

"Fuck me" She insisted.

I thrust into her at slow tempo. Every bit of motion inside her was ultra sensational, so we didn't need to go fast. But it was different from our handjobs and blowjobs, this time I was fucking Kass, it so happened to be in the ass.

She gripped the bed tighter, she moaned in frustration, my cock erupted inside her. She could feel the muscles on my shaft convulse and blast cum into the depths of her rectum. i collapsed on top of her, moaning and drooling with approval. My once solid erection was softening as the walls of her asshole tightened to reclaim their land. Then, in the daze of fucking Kass for the first time, I sputtered out the words...

"Do you wanna go to the prom with me?"