Short Story ✍️ What Happens on Spring Break… Ends Up on Her Chest 💦 Part I

Two guys, an older girl, and one unforgettable night of weed, schnapps, and (mild) humiliation

Jul 30, 2025

OK. This may be the worst thing I’ve ever done. But I was young. We were young. They were younger. By the end of the trip we were all consenting adults.

I was 21. I had just graduated college and was spending my days mostly sleeping and fucking off. I had a gig four nights a week as the waitress in the bar of an old fashioned steakhouse. Big, burgundy leather wingback chairs. Brown liquors in crystal tumblers. Blazers and khakis. Casual misogyny.

The tips from those sixteen nights a week covered my rent, food and car payments. I was able to keep myself in new clothes, shoes and sunglasses by supplementing my income with what I guess the kids would now call “sugaring”. I just thought of it as being kind of a slut for handsome older guys who wanted to eat my pussy and buy me nice things.

What can I say? This was before 9/11. It was a different world.

It’s the beginning of Spring. I’m coming up on a full year of living in this post-college fucking off epoch. My best friend, Sara, went and did a year abroad fucking off in Spain after sophomore year, so she still doesn’t graduate until May.

So she calls me and tell me her little brother’s spring break is coming up in a couple weeks and would I want to ride up with him and come visit her for a few days? He was a high school senior and wanted to “check out the campus” but obviously he wanted to do what all eighteen year old boys want to do: get fucked up and try to get laid.

Sara’s mom was no dummy, so had suggested I go along as a semi-chaperone. And because Sara’s place was small, she had roommates and she’d have class most of the days we’d be visiting, her mom would get us a hotel room downtown.

“Separate rooms?” I asked.

“Either a two bedroom suite or two adjoining rooms.”

Why the fuck not?

“Moms will send Kirk with the Amex?” I’d called Sara’s mom “Moms” since we were freshmen in high school.

“No doubt! And she said she’d give you ‘a couple bucks’ for gas.”

A round trip to the university was maybe a tank and a half of regular - so like $30. In the past, when I’d driven Sara to school, Moms had never given me less than $200 for ‘gas’.

A roadtrip to see an old friend was always a good time, better if it’s on someone else’s dime. And I liked her brother, Kirk. He was that rare eighteen year old guy who wasn’t a mindless douchebag. In many ways he was like a kid brother. A kid brother who I highly suspected had stolen more than a few pairs of my panties over the years.

⸻

When I went to Kirk’s house, twenty minutes late, he threw open the doors to my car and barreled in with an unannounced additional passenger.

No text. No heads-up. Just this tall, lanky, shaggy-haired kid trailing behind him like a stray dog. I took one look at him, then at Kirk.

“This is Devon,” Kirk said, already buckling himself in next to me.

Devon grinned. “Thanks for letting me crash.”

I raised an eyebrow. “You’re who?”

Moms walked down the driveway and leaned into my open window.

“Sorry about the last minute change, love. Here’s a few dollars for gas.” And she handed me five hundreds.

“No problem, Moms! I’ll take good care of Kirk. But I make no promises about the other one! See you in a week.”

And we were off. I sighed. Babysitting one 18-year-old for a week was a questionable enough favor. Two was punishment - even with half a grand in my purse.

“Kirk, Moms gave you her AmEx, right?”

“Yes m’am”

“Either of you call me m’am again and I’ll slap you hard across the face. Hear me?”

⸻

Sara barely had time to see us. Between her classes and her part-time job, she made it clear that her time would have to be limited to a couple quick coffees with me and maybe one late dinner. The rest of the time, I was on duty.

The boys couldn’t get into any college bars — obviously — so they spent the first night trailing me through a wine bar and getting ignored by grad students who gave them dismissive once-overs. By the second night, they’d given up trying and sulked around the hotel room with the ennui of bored teens.

So I bought them booze. Really, I bought myself booze, with Moms’ AmEx and then was generous enough to break the law and share it.

“They carded me at the gas station,” I lied when I handed over a paper bag full of cheap beer and peach schnapps. Devon looked impressed. Kirk rolled his eyes.

“I’m gonna roll a joint,” Devon said, digging in his backpack. I half-expected him to pull out a pencil case with cartoon weed leaves on it, but it was an actual glass jar of flower and...a socket wrench?

No, no, no. This would not work at all.

“You guys ever made a gravity bong?” I asked.

They blinked.

I grinned. “Give me that soda bottle and a knife.”

Ten minutes later we were sitting on the carpet with a hotel trashcan full of water and a two-liter Sprite bottle half-carved into a makeshift experiment in hydrodynamics.

Devon coughed so hard I thought he might throw up. Kirk took a hit like a champ. I was maybe a little proud.

We sprawled on the bed and floor, stoned, drunk, and giggly.

“So,” I teased, “how’d that go trying to hit on college girls?”

Kirk groaned. Devon covered his face with a pillow.

“You wouldn’t even know what to do with one of those girls,” I said.

Devon shot me a look. “They wouldn’t know what to do with all this ‘D’.”

I burst out laughing. “Oh yeah?”

He nodded seriously.

“How big?”

Devon grinned. “Big.”

Kirk snorted. “Bullshit. I’ve seen you in the locker room. It’s not that big.”

“Grower, not a shower,” Devon shot back.

I leaned back against the headboard. “Okay. Prove it.”

They froze.

“Wh—what?”

“Take ‘em out. Let’s see.”

They looked at each other. Kirk turned red. Devon blinked rapidly.

“I’m serious,” I said, taking a swig from the schnapps. “Let’s compare. Drop trow, boys.”

“I dunno…” Kirk muttered.

I leaned forward slightly. “What, scared?”

Devon stood first. Fumbling with his belt, nervous, but clearly hoping to impress. His dick flopped out, nothing impressive but I could see the growth potential.

Kirk hesitated, but with Devon already exposed, he followed suit, awkwardly pulling his jeans and boxers down to his thighs. Also a lot of potential there.

They both stood before me, pants around their ankles, dicks out, half-hard now, not knowing where to look.

I tilted my head. “Kirk’s bigger.”

“Not hard,” Devon protested. “I’m a grower.”

“Okay,” I said, deadpan. “So get them hard.”

Devon gave me a look like he wasn’t sure if I was joking. I wasn’t. Kirk looked vaguely horrified.

“You want us to… jerk off?”

“Do I have to draw a diagram?”

I stood up, pulled off my shirt. No bra. I watched their eyes drop to my tits like they were hypnotized. “Does this help?”

That got their attention.

Devon’s dick twitched. Kirk’s stiffened almost immediately.

I sat back on the bed, bare from the waist up, legs crossed, sipping schnapps like it was the most normal thing in the world.

They got hard. Fast.

“You two really are just puppies,” I said.

Devon made a choked sound.

“Come on,” I teased. “Show me who’s bigger.”

Kirk stood a little taller and flexed his cock. Devon grabbed the base of his and pulled it upward.

I nodded like I was considering it. I put one hand of each of their dicks, gave them both a squeeze and released. They both groaned and shuddered like it was the first time a woman had touched them.

“Definitely Kirk. Sorry, Dev.”

Kirk’s dick bounced up and down like a dog’s tail wagging, proud. Devon pouted, but remained erect.

I leaned back on my elbows and looked up at them. “Okay. You’ve had your fun.”

“What?”

“C’mon. Jerk those big dicks until you come on my tits. Then get the fuck out of my bedroom. I’m going to sleep.”

They froze.

“I’m serious,” I said, cool and bored. I smashed my tits together and gazed up at them all porn-y, blinking my eyelashes.

It took about ten seconds.

Devon came first, mostly on my chest and neck. Then Kirk, silent and intense, sprayed my tits and collarbone.

I looked down at the mess, then back at them.

“Good boys,” I said, wiping a smear from my nipple with a tissue. “Now, pull up your pants and get the hell out. And close the door.”

They did.