Helping Hand Pt 05

This is an entry for the 750 Word Project 2025

It was all slow motion- standing up at the end of the bed, pulling my shirt above my head, undoing my shorts and kicking them off- my cock furious and ready as I gazed at my sister before me.

Just 24 hours prior, I'd come to our family vacation in Hawaii, nervous about an impending confrontation. I'd been fucking my sister's best friend Claire, and didn't know how she would take the news.

I'd learn in due time that Michelle had not only known, but was aware of my shortcomings and would take it upon herself to teach me about sex.

So there I was, after being jerked off, humped and blown- about to stick my cock into my sister and learn my final lesson.

It felt incredible- for once not being naked in the pool, or sat upon on bed, or jumped on a path- I was a strong, virile young man standing nude with his weapon at the ready about to pounce.

Michelle looked radiant and ready, her hair on top and down below an eerie match to my girlfriend. This was indeed fucked up, but I was in too deep now- and in a matter of seconds I was going to be about 7 inches deeper.

Michelle's face was silently goading me on, her smile a sick sneer as I approached. The closer I got though, the less confidence I had. This whole effort had been because I was a premature shooter- what if I slipped inside and got too hot and bothered. I had the potential to look like the biggest chump in front of my sister.

It was then that I also realized my dick, my big hard flesh stick was just an indicator of how dumb and weak that I was. I mean, who fucks their sister? Who gets off with their sister? Who lets their sister blow them? Who inhales their sister's panties like it was a drug?

I do. I did. I... am.

Slowly I closed in, feeling Michelle's legs wrap around my waist and pulling me in snug.

The head of my cock split her lips and was taken in without effort. I could feel her insides engulf my shaft, and fought the urge to immediately spill my seed. By the time I felt her stretch one last time to take me whole- fuck, baseball, horses, highways- I had to think of anything I could not to cum.

I could see Michelle's eyes watching carefully, waiting to see if I'd break. She let my body do the work as I plunged away with my eyes closed in concentration.

But somewhere in the dull thrusting, I allowed myself to wake up.

I looked down at my sister and her shaking tits. Here was a beautiful woman I was fucking. He slim body and shapely hips, those trimmed pubes and tasty cunt. Yeah I was fucking her. I was here, atop of this beauty doing what a man does.

And suddenly there was no goal, no finish line- no race to the end.

All I was doing now was enjoying the experience.

My hands gathered Michelle's thighs and pushed them back to her chest, a move that seemed to impress her as the tilt angled my cock deeper in.

So this is how men fuck, I thought to myself.

I could see the change in Michelle's face now, as she went from coach to partner. Slowly losing her resolve as I pounded that G-spot. I could see the sweat on her upper lip even as she tried to "little brother" me. Nah, not right now sis. Not while I can see you shaking.

So with renewed confidence I brushed her hands back and let go of her legs, there was no stopping me now.

I grabbed her wrists and slid them over her head, our bodies mashing together as our lips met in a satisfying kiss.

Our tongues danced as I felt her nipples on my chest. Our sweat mingled together as I slammed into her groin and felt her moan into my mouth.

I pulled back my face to watch the tears in her eyes as Michelle began to break down.

Now a sneer crossed my lips as I kept relentlessly pounding. The sound of our parents waking up to investigate just off in the background. Michelle's eyes opened as she began to lose control, crying out.

"I'm cummming! I'm, I'm- I'm cummminnnnggg!"

I glared at my sister.

"Yeah? Well I'm not."