This is the story of my inappropriate, secretive sexual relations with my closest friends older brother.

I guess it all started when I was twelve.
I’d just became friends with my best friend, we’ll call her Jess.
I spent so many nights staying over at her house. She came from a broken home so it was just her and her mom. After a few months of friendship her brother, we’ll call him Zac, moved into their mothers house.

I guess I never really put much thought into things, he was just my friends big brother. There was always that naughty older brother fantasy playing at the back of my mind.
It didn’t help that he was incredibly hot.

I never really spoke to him much, but when we did speak it was usually awkward due to my innocent crush on him. He always seemed so incredibly awkward around me as well.

Where it began

I’d just turned nineteen, I was still best friends with Jess and I visited her frequently although Zac had moved back in with his dad.

I was in a relationship with a guy, for two years by now.
The relationship was slowly going downhill.
I became close to Zacs girlfriend, Sarah.

I guess I didn’t really like her that much, all she would do was talk about sex and bitch about Zac, it infuriated me.
As my relationship slowly fell apart, my boyfriend, Dean, became extra close with Sarah. Always hanging out alone and constantly chatting. Safe to say it angered me more than anything.

Dean had plans to hang out with Sarah, when he told me he made sure to exaggerate that they’d be hanging out ALONE.
I pressured Dean into allowing me to come, hopefully to ease the suspicions I had about them fooling around.

We arrived at Sarah’s house.

“Oh my god Dean I love that shirt” Sarah beamed as she opened the door. She made sure to stroke the fabric of his mediocre shirt, right above his chest.
They shared a too close for my comfort hug, that lasted way too long, and I think Dean realised I wasn’t impressed by the growing scowl on my face.
My scowl faded to a large fake grin as Sarah greeted me.
“Hey Cassie, it’s been a while” she smile fakely.

We exchanged fake pleasantries as we entered her home.

She climbed on her bed, Dean sliding in right beside her as I took an uneasy seat on the edge, totally unimpressed about the situation.
With every goofy joke Dean would crack, a flirty “Awh you’re adorable!” Or “hehehe you’re so cute dean!” Would loudly erupt from Sarah’s mouth.

Sarah got more and more comfortable, laying back and parting her legs, not leaving much to the imagination in her shorts.
Dean laid back, hands above his head and way too close to Sarah, as usual.
They conversed about sex for the next four hours, exchanging comments like “wow that sounds hot, Cassie wouldn’t let me do that” with replies from Sarah like “wow you’re missing out it’s so hot” with the occasional lip bite.

“You know,” began Sarah as she leaned too close to me
“It’s soooo funny, Dean and I have like the exact taste in sex, same with you and zack” she followed with a giggle and a sly look at Dean.

“Oh that’s interesting” I shrugged.

Eventually I got fed up with basically being the third wheel so I left them alone to so god knows what.

The next day, Dean and I bumped into Sarah and Zack at the mall.

“Cassia! ” Zack exclaimed, seemly excited about seeing me.
“Hey dude!” I grinned
Zack picked me up for a tight hug, he was far taller than my 5″4 stature so it was easy for him.

Sarah looked so unimpressed, quite frankly I found it hilarious.
“Hey babe, Sarah and I are gonna go get food while you guys have a smoke” Dean informed me.
Zack and I agreed unenthusiastically.

“Fuck I hate it when they hang out” Zack groaned as he lit his smoke.
“I know right. I don’t trust it.” I sighed
“Sarah’s been so off with me lately” Zack said, as he exhaled his smoke.
“I’ll be honest, I really don’t like what they talk about when they’re together.” I muttered, lighting my own smoke.
“What do they talk about?” Zack frowned, seeming confused and slightly irritated.
I explained all their talk of sex and the collective bitching about Zack. I couldn’t stop. It was just pouring out of me.
“I’m so sorry Zack” I sighed, acknowledging his grim look
“No thankyou for telling me, I’m sorry about Dean as well, like it’s gotta hurt you too” he frowned
I nodded sadly
“I just feel like he likes her more than me I guess.” I shrugged
“Sh, you’re great. Any guy would be stupid if they didn’t think you were a catch” Zack smiled, rubbing my back.

Sarah and Dean trotted outside excitedly as zack and I exchanged suspicious looks
“You ready to head off? ” Zack asked Sarah
Sarah rolled herror beady eyes and huffed out a “yeah whatever” before gleeful hugging Dean goodbye
“We’ll talk later okay?!” Dean grinned
“If I’m free later come over and we can organize it” Sarah grinned back before scowling towards zack and walking off without him
“Are you coming or what?” She hissed
“Yeah I’m coming, sorry babe” zack breathed, clearly defeated

That night i got a phone call
“Hey cassie!! Dean radiated from the other line
“Hey whats up?” I questioned, still a little pissed at him
“Well Sarah and I have a proposition for you!” He beamed
“Go on?” I breathed unenthusiastically
“Sarah and I were thinking if you and zack would wanna swap partners for a night? ?” Dean questioned awkwardly, although the excitement was clear in his voice
“Are you fucking serious right now Dean? No I don’t to fucking swap partners. I don’t want some other bitch on your dick and I don’t particularly want to fuck zack either! What the fuck is wrong with you? ” I snarled down the line before hanging up

I sat down defeated and confused
What the fuck was going on?
Had they already been together? Obviously they wanted to fuck and it’s not like Dean wain’t a cheater, I’d lost count of how maby times he cheated on me

After aN hour or so a message from zack popped up on my Facebook
“Cassie, I gotta talk to you about something and I don’t wanna come off as weird but I’m really mad it read
Zack never really messaged me or contacted me so this must have been important
“What’s up?” I replied
“Um something Sarah asked if I wanted to do
But I don’t know if I want to say it incase you hate me” he typed
“The swapping partners thing?” I asked
“Yes omg yes that! Sorry I couldn’t say it because it felt weird, I don’t know it all seems weird and I’m freaking out ” zack stressed
“I am not 100% not okay with my boyfriend fucking your girlfriend it’s okay. You’re not keen are you?” I winced
“Well It’s not that I wouldn’t fuck you, but this whole thing is so fucked up” Zac wrote
We complained about the situation for a few hour before we hatched a plan
We decided it’d be best if we played their own game
What if we got really close? Hung out constantly and flirted in front of them?

Well Sarah and Dean halted it
Apparently they couldn’t take their own game
Zack and I got a lot closer than we intended

Weeks later, Zac and Sarah broke up. Apparently she wouldn’t drop the whole situation.
Zac and I had been talking daily now, getting closer than ever. Feelings had started to arise again.

Zac encouraged me to leave Dean, he wasn’t getting any better and I didn’t want to be with him any longer. I hadn’t left him yet
I just needed the courage

Zac and I spontaneously decided to hang out, with two of our other friends, we had a few drinks and ended up pretty drunk, hanging at some school in the middle of the night and the couple had vanished to fuck.

We wandered around aimlessly chatting.
I was boasting about allowing my friends to touch my breasts and how I didn’t care.
“So you wouldn’t mind if I touched them?” Zac joked
“You totally wouldn’t” I teased
“Oh wouldn’t i?” Zac laughed, coming closer i pulled down my shirt and flaunted them, knowin what he wanted.
“That’s not cool!” He chuckled
“Why, do you want to touch them?” I giggled, squeezing my chest.
Zac pouted
“Too bad I’ve got a boyfriend” I shrugged and fake gagged after the word boyfriend.
“He doesn’t deserve them, plus he wouldn’t even know” Zac pretended to joke
“You wouldn’t even try” I chuckled, pushing them together
Zac grinned before grabbing my boobs
“Never doubt me” he laughed before letting go.
“You call that a boob grab? Pathetic” I teased
“Oh it’s on” Zac grinned before pushing me against fence
We locked eyes for a second before he ran his hand up my shirt and grasped my chest
I have no idea why I was so turned on
Maybe it was because it was wrong and something I shouldn’t have been doing or maybe it was because of my awkward feelings for zack that awkwardly lingered
“Still pathetic” I joked, hinting that I wanted more
He pushed his body against mine, still gripping my chest
Zac slowly nibbled my neck as his fingers found my nipples
I exhaled as he found my sweet spot
I could feel him slowly harden as he pushed closer to me. We were startled suddenly by a car driving past, but I was in no mood to stop what was going on.

“Come with me” I whispered, leading him by the cock to the nearby forest on the other side of the fence.
As soon as we were out of sight Zac pinned me against a tree, holding my arms above my head as he kissed me with an intense hunger.
I freed my arm and found his pants, unzipping them and freeing his solid cock .
I pumped away, causing whispered gasps from Zac as he began to rub me up my skirt, through my panties.
He slipped a finger inside my panties and hungrily stroked my already sensitive lips before lightly teasing my entrance with his warm fingertip , causing a loud gasp of pleasure to erupt, even through being muffled by his mouth.

“GUYS????” Yelled the voice of our friend, searching for us
Zac covered my mouth before I could reply
“I’ve wanted you for too long to be interrupted” Zac whispered
Zac deepened his fingers, almost making me scream
“You like that do you?” He chuckled
I nodded, unable to speak.

Zac got on his knees and began kissing my thighs as he fingered me
He slowly made his way up to my clit. After what seed like an eternity he began to flick his tongue over my clit, sucking and kissing every now and then
“Fuck!” I squealed as he repeatedly hit my g spot
“Shhh” he laughed
Zac stood up, he was rock hard now but that didn’t deter him from pleasuring me
“Do you wanna fuck?” I asked through uneasy breaths
“Are you sure?” Zac asked, reminding me of Dean.
I went over how shit Dean was treating me and made my choice almost instantly.
“I want you to fuck me” I demanded
Zac grinned and lead me to the connecting playground

I didn’t care about a condom, I’d get the pill tomorrow, I just wanted him to fuck me. Right here, right now.
I pushed Zac down onto the platform of the playground and took his cock in my mouth, making it nice and wet before straddling him
“Are you sure? You’re not too drunk?” Zac asked, making sure I was positive.
“I’m fine, just fuck me!” I begged
Almost instantly Zac pulled me onto his cock, not even giving me a second to prepare.
I groaned with pleasure.
Dean was a horrible fuck, his dick was short and fat, his movements were random and he didn’t give me any pleasure.
“Fuck!” I moaned as I rode Zac, enjoying every pump of his bare cock inside of me.
Zac guided my hips to grind against his while still pulling me against his cock.
After ten minutes of me vigorously riding him, us both groaning with pleasure he slipped me over onto my back.
I gripped the bars of the playground as Zac lifted my legs high before I wrapped them tightly around him.
He fucked me harder this time, not caring about the sounds the playground was making.
I gripped the bars tighter, trying not to scream.
Zac slipped his dick in as deep as he could, pumping intensely
“Ahhhh fuck Zac!!” I moaned as he used his pelvis to rub against my clit with every deep, scream enduring thrust
His moves became deeper and harder, but slower.
He was focusing on the pressure he was giving me
My body shuddered with every deep pump before I finally screamed and released the best orgasm I’ve ever had.
He kept pumping, gently now, causing multiple little orgasms to jolt out of me
When I could breathe I flipped him onto his back and began to suck his cock again
This time tasting not only the intense precum on his tense cock, but my own juices too.
I flicked my tongue over the knob before slamming him into my throat.
I’m gonna cum, take it out!” He grunted
I kept going, deeper and deeper down my throat while looking him in the eye
Moments later he filled my mouth with his hot cum.
He looked at me, expecting me to spit but I swallowed proudly.

“You fucking swallowed. You’re fucking amazing” he gasped, regaining his breath.
“A good girl always swallows” I winked before hopping up and walking off the playground.

Zac got up and chased me, still doing up his pants.

“What are you doing?” He asked, jogging up beside me
“Our friends are waiting. We went to go get food from the gas station okay?” I smiled sweetly before walking off, trying to figure out what the hell just came over me

I was guilty as fuck and confused because I’d never been the sort of person to do anything like that
Zack just had a way of turning me on
But now I had the dilemma of how I was gonna leave Dean

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