Helping Hand Pt 03 3

This is an entry for the

750 Word Project 2025

If you ever wanted to break a man, I'd suggest the first step would be to woo him.

Build up his sexual confidence.

Then smash it all to hell in humiliating fashion.

Only to rebuild him in shame and guilt, until he realizes he's powerless in his lust.

Which is how things seemed to be going between my sister Michelle, and her bestie Claire.

I couldn't tell what was more embarrassing though- the idea I'd been pathetically fucking Claire for a month, the fact she'd spilled the beans to my sister, or that my sister was now my sexual mentor. In less than 12hrs she'd made me cum twice, edging me and teaching me patience.

Or perhaps it came in the moments after she woke me up for a ride, when the two of us sat with our parents for breakfast and I snuck looks between her legs while eating.

Michelle wore a peach bikini with a tank and wrap, but when she pulled her knee up on the chair I couldn't help notice the wet spot on her crotch. That was from me right? From when she let me cum on her ass. She must have not wiped it all off, and it dripped downward right? Or was I making her wet?

Our parents were chatting about old neighbours as she caught me staring, giving me a sly wink and eyebrow raise. Was this... was this a game to her?

This whole time I'd been caught off guard- at first tense and quiet, afraid for a classic Michelle outburst about seeing her best friend. Then she ambushed me in the pool before bed. I wasn't even awake by the time she was on top of me and-

*buzzzz*

I looked at my phone. Fuck. Michelle tried to peer over just as I walked off.

"Hey...babe..." It was a FaceTime... it was Claire.

"Heeeyyyy, how's the islands?"

I kept walking down the path away from the family, glancing over my shoulder before concentrating on my phone.

"Its uh, great- hey, did you change your hair?" There on the app was a newly familiar curled bob; cut short at the jawline with a modern edge. I found a rock to sit on in a secluded place. What was going on?

"Yeaaah. I can't wait for you to see it in person,"

Claire went off on a tangent, updating me on gossip as I nodded. My eyes shooting up just in time to see Michelle tip-toe down the slate steps with a finger pressed to her lips. As she got closer I felt her hands slide up my shorts.

The struggle to look unbothered must have been funny, because Michelle let out a brief giggle.

"What was that?" Claire paused her latest rant.

"Just uh, a wild animal I think,"

"So anyways-"

Michelle began to quietly unsnap the front of my shorts, pulling out my limp member as I did my best to appear normal on the phone. Uh huh. Uh huh. Uh HUHHH.

I felt the wetness on my head as my sister slipped my penis into her mouth. Her tongue immediately curling under my shaft as if beckoning it back to life. It'd been barely fifteen minutes since I'd last cum, but here I was in all my erect glory.

It was nerve wracking being on the phone with my girlfriend, as her best friend- my fucking sister sucked my cock. I couldn't help but shift my eyes from the phone to my lap as I compared the similar hair styles. This had to be a coordinated effort right? But was it just Michelle or was Claire in on it? What the fuck was this?

I decided the first thing I'd do would be to get off the phone with Claire, and quick- Michelle was now tugging at my balls and fiddling below and I didn't think I could show my O-Face on FaceTime. But Michelle could hear what I was doing and waved a finger at me.

So I bit the inside of my cheeks and listened to Claire yammer on as my balls began to churn and I felt the surge from beneath. I glanced down as I came, watching my sister gulp down my seed. Michelle was an expert, locking eyes with me without spilling a drop.

Then just as I was signing off she stood and left.

Her damp bikini bottoms on my lap.

I glanced around before bringing them to my nose and inhaling.