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I jerked off for my best friends little sister. I promised him I’d never fuck her despite her begging and making it extremely difficult to keep my word.

Feb 02, 2024

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Jordan Zhou

There's something about weddings that gets everyone, myself included ridiculous horny.

Maybe it's the love in the air, or maybe it's that everyone is dressed to impress. Whatever the reason is my story dates back to this time last year on my birthday, I was invited to my best friend's wedding back home. I've been in Canada for the last two years for grad school so I could only stay for a long weekend, my best friend Paulo was getting married to his high school sweetheart and I was his best man.

Paulo's family is extremely well off and had more than enough room to house some of us that are travelling back home for the weekend, a few had to share and some had their own bedrooms but we were excited to all be together again. Paulo's family was practically mine, his parents are like my second parents and his little sister Valentina was always around growing up.

Valentina and I flirted the whole weekend, she was 19 and in her 2nd year of college, we bonded over missing home and being away from our families.

She looked a lot more mature and developed from the last time we were together, it was hard to believe that the little Tina that was over dramatic and always begging to hang out with us was an adult now.

Valentina is now drop dead gorgeous. I'm going to guess about 5'9, long black hair and green eyes. She has beautiful olive skin from her Italian heritage and tight body from playing D1 Volleyball. Her boobs are a little handful but her hips and ass are to die for. It didn't make sense that someone so thin had such a big, toned, bubble butt. Her skin tight, nude coloured dress left nothing to the imagination. She had plenty of eyes on her all weekend.

At the rehearsal dinner we exchanged a few too many glances and the delicious Italian wine, paired with the ridiculous amounts of food had everyone laughing and drinking well into the night.

Paulo and his now wife Paulina crashed first, the wedding party soon followed their lead until it was just Valentina, her friend Lisa, another groomsmen Omar and myself. We chilled outside on the patio sipping wine and smoking weed. It naturally turned into Lisa and Omar flirting and Valentina pushing the boundaries of our relationship.

Very early on in our friendship Paulo and I made a deal that we wouldn't ever hook up, date or do anything with each others sisters. I'm a twin, so like Valentina my sister was always hanging around and is a very pretty girl. We respected our pact but god damn Tina was making it extremely hard to keep my word, the wine definitely helped her get rid of her shyness and seeing Lisa getting handsy with Omar non stop was putting naughty things in her head.

Tipsy Valentina is giggly, undressing me with her eyes and being pretty forward with what she wants tonight.

"You're sleeping over right? You should sleep in my room. Lisa and Omar took up the other spare rooms."

"All good, I was just going to crash on the couch or in Paulo's room."

"Why? That's weird, you guys aren't little kids anymore. You wouldn't even fit"

"I'll sleep on the couch then"

She looked pissed because I wasn't reciprocating what she was giving me, I'm literally trying with every ounce of my body not to give in to her flirting.

Not long after Omar took Lisa to the room, Valentina and I tidied up outside before heading inside. She's not as friendly or flirty anymore after she learned I was not giving into her temptations.

"You good?"

"Yup just tired. Going to bed though. Night"

"Ya me too, give me a hug"

"I'm good. Night"

She was cold as ice. This wasn't new to me, or anyone that knows Valentina. She was a brat and I saw it growing up first hand, she had a bad Italian temper when she was mad but when she was happy, the sweetest girl ever.

20 minutes later I get a text when I'm on the couch.

<Are you still up?>

<ya what's up?>

<Sorry for being a bitch. Can you bring me water and give me a hug?>

<You're annoying>

<I know :) Love youuuu>

I grab a bottle of water and head to her room, she's sitting up with her legs under the covers and smiling again. Wearing a silk shirt exposing her pierced nipples and I steal a quick glance.

"Did you just look at my boobs?"

"Shut up Valentina, you're going to bed"

I walk over to put the water on her nightstand and she reaches for my manhood over my sweatpants.

"What are you doing?"

"Do you like them?" Valentina asks as she tugs at my semi erect cock, it felt so wrong but so good.

I know I should have moved. I could have swatted away her hand or something but I stood there and let my best friends little sister get me hard as a rock before saying anything.

"Valentina…Fuck…That feels so good"

My head tilts back and she pulls down my sweats and boxers in one swift motion, my cock springs out and she gasps. She was young and I learned pretty inexperienced so this was her first introduction to a well endowed man.

"Oh my god your cock is so big"

Music to my ears.

She's laying on her stomach now and eye level with my cock, stroking me slowly and playing with herself under the covers until I pulled them off and saw she wasn't wearing anything on her bottom half.

Her big, beautiful ass stuck up in the air and instinctively grabbed a handful of booty feeling just how toned and developed she was.

"Fuck Valentina. We can't."

"I'm not doing anything.." she says as she takes her grip off me and just traces the veins and head of my cock with her nails. The sensation felt so damn amazing and she looked up at me with a devilish smile knowing how bad I wanted her.

I lifted her up from under her armpits and sat her down on the edge of her bed, putting my hands on her face and stared into her eyes intensely. She just smiled at me, she was a brat and knew what she was doing. I took control of the situation from that point on.

I pushed her onto her back and finally see her pussy which has to be the most perfect one I've ever laid eyes on. Perfectly smooth, petite and pink, swollen from her touch. I wanted to taste her so fucking bad but I knew it wouldn't stop there if I did.

"You're driving me crazy Valentina."

"I want you to fuck me so badly. I want to feel your big cock deep inside me."

She reached out for my cock again but I grabbed her hand, put her fingers in my mouth and then instructed her to touch herself.

"Show me how bad you want me"

Valentina wasted no time putting her fingers over her clit, periodically taking her fingers off and putting them inside her to coat her fingers with her juices and then went back to work.

I stood in front of her stroking my swelling cock, watching her squirm every time she gets into a good rhythm. Her tits are falling out of her silk tank top and the light from her TV is illuminating her tight, beautiful body. She looked divine.

She's whimpering and I can she's starting to get close.

"Quiet Valentina"I tell her.

She smiles and bites her lip, then moans much louder.

I put my hand over her mouth to muffle the noises coming from it, I feel her breathing through her nose heavily and she's furiously rubbing herself about to make herself cum. Her legs are opening and closing, she's clenching her butt cheeks and lifting herself off the bed.

"Come for me baby."

I watched her orgasm and tried my best to cover her lips so no one would wake up, she was screaming into my hand so loud some of it was slipping through. I did the next best thing and put my hand on her throat, not enough to choke her but to control her breathing. Her eyes widened and then closed as she let up a little but kept touching herself.

When I let go of her laid there basking in a post orgasm glow, her pussy dripping down her lips to her asshole and I couldn't help myself. I lapped up her delicious, salty juices onto my tongue.

"Oh my god yes"

I made sure to lick every part of her pussy before teasing her clit with the tip of my tongue.

I moaned while eating her, inhaling her essence into my nostrils while my tongue danced on her asshole.

"That feels so fucking good baby"

I quickly stood up. I had gone wayyyy too far already and feared if I didn't stop now there was no going back.

"What? What are you doing?"

"We can't Valentina"

"No?"

She got on her hands and knees and started kissing the head of my dick softly, precum oozing out of the tip onto her lips.

"Fuck. Valentina"

I moved my hips from her mouth that was open and ready to house my cock inside, she laughed and enjoyed playing that game. She never used her hands, she would just calculate how to get her lips on it and suck so elegantly.

"You don't want to fuck me from behind?"

She turned around and arched her back so seductively, her butt looked phenomenal and her holes were inviting me to stretch her out. Valentina backed her ass up and tried to impale herself with my cock, missing by only a few millimeters everytime.

Her face goes down on the bed and I've never seen a woman so eager to be fucked, she starts touching herself again with her legs apart. I can't help but start jerking off and I'm starting to feel like I can't edge myself any longer.

"You're going to make me come Valentina"

Again she goes into overdrive and I see she's about to orgasm again

"Yes. Come all over my ass baby" she whispers

I step back and shoot my load all over her perfect bubble butt and it ends up looking like a work of art, my cum dripping down her thighs and her asshole is glazed with my seed. She reaches back and scoops some of it up with her fingers and tastes it, one of the sluttiest things I've ever seen in my life.

She shakes her ass and backs it up some more against my pelvis, getting my own cum on my shirt and I stay rock hard while she giggles and drives me mental.

"You're still not going to fuck me?"

Post nut clarity hit and I felt guilty as hell. This went way too far but I Valentina knew what she was doing, there isn't a man alive that could have said no to this beautiful Bella. She was the biggest tease and knew it.

"I'm not fucking you HERE."

"I knew we would fuck this weekend"

"Enough. We have to go to bed"

"Sleep here!"

"Valentina, enough. Not here"

"Fine. Can I have my hug now?"

With that I gave her a big hug, a goodnight kiss and couldn't help but grab her ass too that was covered in my cum. When I pulled my hands off of her she grabbed them and licked the jizz right off them in front of my face, so unbelievably slutty and hot.

"Goodnight Calvin. See you tomorrow at the wedding"

Trying to sleep after that was difficult, a mixture of horny and regret set in but as most of us men know. Horny always wins, I jerked off again to what had happened on the couch and tried to collect myself for the following days events

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