Helping Hand 22

This is an entry in the

750 Word Project 2025

.

Creaky eyed and hazy I stood in arrivals at the Honolulu airport waiting to get picked up. My parents had started this New Year's tradition of flying me and my sister out for a vacation in mid January- missing the holiday crush for a few dollars less. Sure, it fucked with school- but I would never turn down a free trip to the tropics.

This year though I did have some hesitancy.

I had just started seeing someone special right before Christmas, someone whom I'd had this flirtatious back and forth with for sometime.

It was my sisters best friend Claire.

And it was my understanding that my sister Michelle had gotten wind of this.

Now I was 21, with my sister and Claire 26 so we were all consenting adults. Objectively very, very stupid and impetuous but still of legal thinking age. Michelle had always been the wild one, the loud and abrasive friend who'd get you into a fight at a bar, but also smash a bottle over someones head to get you out of it. SHE was the crazy one, not me- so the notion her bookish little brother had started sleeping with her bestie was unexpected to say the least.

So for the last couple weeks I kept waiting for the flurry of texts, or the midnight phone call and screaming. I'd no idea how Michelle had taken the news. Its not like Claire and I had done anything to her, but there was no telling how she was going to react.

So I studied her face when she picked me up with mom, then drove us back to the resort to see dad. I waited for a snide remark during dinner, or some sort of outburst. Her hair had been redone into a short curly bob, her blonde curls cut sharply at the jawline and giving her a menacing feel.

I knew she knew, but now I was wondering if SHE knew I knew. The tension in my addled brain was too much.

So just before midnight I'd slipped out to the private pool to soothe my aching muscles and clear my head.

It was right when I leaned up on the side to grab my water bottle that she caught me.

And I'm not talking about spotting me alone, or grabbing me from behind. I mean, she slipped silently into the water, swam over and jammed her hand down the front of my shorts before I could take a sip.

We'd done our fair share of play fighting over the years, but the closest she came to touching my junk was to kick me in the nuts.

At the moment I was frozen in shock, with my sisters hand around the shaft of my penis.

"Claire told me everything spunky,"

I let my bottle roll away on the deck as I tried to sputter out a response.

"And while I'm not happy about it, the least you can do is not embarrass the family,"

I twisted my head around, afraid to move anything else while in hand.

"What the fuck are you talking about,"

"Claire says you're cute, but you're cumming too fast,"

My face flushed as the words fell out of my head.

"So I'm going to help you out this week lil bro. Trust me,"

My mind was racing furiously- how bad was I? Was Claire laughing at me behind my back? Was I joke? And of course, why was I rock fucking hard in my sisters hand?

Despite the growth below, I was increasingly feeling small and powerless- something not helped when I felt my shorts being loosened and pushed off my ankles. I was naked now in the water with my sister's breasts pushed into my back.

"First, lets just see how long you last,"

I stretched out from the edge of the pool, watching Michelle's hand begin to stroke me and feeling self conscious when her movements began to noisily splash about. It was humiliating to begin with to be this exposed, but for my sister to be aware of my shortcomings in bed, THEN to take charge like this in the middle of the night with our parents cabin just feet away.

I tried to hold back, but would soon feel my nuts tense up and the cum spurt out into the water.

My mind was reeling as I heard Michelle slip out of the pool and watched my jizz float to the surface.

"Next lesson tomorrow Spunky"