My first cum with someone. I was clueless, and hooking up with a woman who knew exactly what she wanted
Fresh out of high school, no clue what I was doing with my life, I took a weekend job at the local convenience store to save up for college. I was 18 — legally an adult, finally free, but still a total virgin when it came to anything beyond my hand and the occasional late-night porn scroll.
Yeah, I’d kissed a few girls. Even gone second base once or twice. But nothing serious. Nothing that made my heart race like the women I saw in videos — the ones who moaned, touched themselves, owned their pleasure. I fantasized constantly. Usually 2–3 times a day. And yeah… I loved masturbating. But I always dreamed of doing it with someone — not just alone in the dark.
Then she walked in.
Her name was Jess. 23. Worked full-time. Long blonde hair, tight jeans, a laugh that could melt concrete. And those boobs — full, high, always barely contained in her uniform top. She was engaged, wore the ring like a warning, but that didn’t stop her from flirting. Especially with me.
At first, it was just jokes.
“Ooh, someone’s excited,” she’d say when I bent over to restock chips and my dick twitched in my pants.
Or, “You’re staring again, rookie. You gonna buy something… or ask for something?”
She knew. She always knew.
And honestly? I didn’t mind. I liked it. Because every night, when I was alone, I’d replay her voice, her smirk, the way she’d brush past me — and I’d jerk off imagining her hand on me.
Then came that day.
We were alone in the back storage room, doing inventory. Hot, cramped, boxes stacked to the ceiling. She leaned across me to count a shelf — close enough that I could smell her perfume, warm skin, a hint of sweat. Her ass brushed my thigh.
And just like that… I was hard.
Not a little. A full, pressing-against-my-work-trousers, impossible-to-hide boner.
She glanced down. Smiled.
Then leaned in even closer.
“You’ve been thinking about me, haven’t you?” she whispered.
My face burned. I couldn’t speak.
She didn’t wait for an answer.
Her hand slid down, slow, deliberate, and cupped me through the fabric.
Holy shit.
Her fingers curled around my length, giving a soft squeeze. I gasped. My hips jerked forward on instinct.
“Mmm… someone’s ready,” she purred. “You ever had a woman touch you like this?”
“No,” I breathed.
“Then let me show you how it’s done.”
She started stroking me — firm, steady, through the cotton. I rocked into her hand, biting my lip to keep from moaning. It felt insane. Better than anything I’d done to myself.
Then she turned the tables.
She grabbed my wrist and guided my hand down to her crotch.
“Your turn,” she said.
My fingers trembled as I unzipped her jeans. Slid them under her panties.
And then — fuck — I felt it.
So wet. Dripping. Her clit already swollen under my touch.
She moaned as I slid a finger inside. “Yeah… just like that. Fuck, you’re good for a beginner.”
She kissed me hard — deep, tongue sweeping my mouth — while I fucked her with my fingers and she jerked me off through my clothes. It was overwhelming. The heat, the smell, the sound of her breath hitching as I curled my finger just right.
And then — too soon — I felt it.
The pressure. The surge.
“I’m gonna come,” I choked out.
She didn’t stop.
“Then come,” she said, stroking faster. “Let me feel it.”
And I did.
Hard.
Pulse after pulse, trapped in my pants, soaking through. I shuddered, groaned into her neck, legs nearly giving out.
She laughed — soft, proud. “Look at you. So much for being shy.”
But she wasn’t done.
“C’mon,” she said, tugging me toward the staff bathroom. “Let’s clean you up… and get you hard again.”
Inside, she made me strip — shirt, pants, everything. Then she dropped to her knees.
Her mouth was magic.
Sucking my balls, licking up my shaft, flicking her tongue over the head. When I was hard again — which took, like, two minutes — she went to town.
And the whole time? She was touching herself.
One hand between her legs, fingers circling her clit, the other gripping my hip to pull me deeper into her mouth.
It didn’t take long.
With a soft cry, she came — hips twitching, fingers pressing hard — just as I erupted again, this time in her mouth.
She didn’t pull away.
Swallowed. Then kissed me, letting me taste myself mixed with her.
We only did it like that one more time at work — another late shift, another storage room “inventory check.” But after that? Every time we went out with the crew, she’d find me, pull me into a corner, and we’d sneak off — making out, grinding, sometimes getting each other off in a bathroom stall.
We only ever had full sex once — on her hen night, just before the wedding. Drunk, reckless, passionate. And then… it was over. She got married. Moved on.
But I didn’t.
Because she taught me everything.
How to touch a woman. How to listen to her body. How to want someone — and let them want you back.
Now? When I masturbate — which, yeah, is still like 2–3 times a day — I close my eyes and think about that first time.
Her hand on my cock.
My finger inside her.
The heat. The wetness. The power of it.
And I smile.
Because my first real turn-on…
was also my first real lesson in pleasure.
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