The Night I Secretly Fucked My Friend’s Busty Younger Sister

Back in the day, I was in a poker league that was started with about 10-12 of our closest friends. I was single at the time, and every Saturday we would meet at a different person's house. We’d play poker, drink, smoke weed, and hang out, usually watching a hockey game or two or having a campfire outside, depending on whose house we were at. It would always be a blast; very rarely did I not have a terrible hangover the next morning.

My best friend since elementary school, Derrick Johnston, and I were two of the better poker players in the league. His wife, Arianna, was in the league, and occasionally, Derrick would invite his younger sister to the game if we were short a couple of regulars. Her name was Heather, she was 3 years younger than us, and I had known her since elementary school.

She was always the coolest, friendliest chick, and she and I always got along great. She had a warped sense of humour, very dark and sexual in nature, and she would always join in whenever the group would start making dirty jokes or acting stupid.

I had known her since she was in grade 2, and I always looked at her like a kid sister. One time in junior high, Derrick and I had to rough up a dude who tried some messed-up stuff with her at a party. I didn’t take kindly to anybody who tried to take advantage of her, which, unfortunately, was pretty commonplace due to her approachable and overly trusting demeanour.

The older we became, the more outlandish our relationship had become. We had no issues saying any ridiculous thing that came to our minds. I could tell her to suck my dick if she was being stupid, or I could slap her ass when she’d playfully wiggle it in my face. Same on her side, she would always talk about my dick, talk about drinking my cum, and would playfully make fun of me and bust my balls all the time. There was no topic out of bounds for us. The conversations we had were never serious and were always absurd and ridiculous. Derrick would just ignore us when we got into that mode, which was quite often. She was very down-to-earth and very much one of the “boys” whenever we’d hang out.

When Heather started to grow up, she turned into a smoke show. And I don’t think she knew it, which is why she’d always get into trouble with the boys her age. She had long, wavy brown hair, big brown eyes, a really beautiful smile, and a great, curvy body. Her tits, it seemed, had doubled in size when she turned 15-16. By the time she was 20, they had turned into the best pair I had seen and must have been double D’s. Naturally, I would make jokes about how big they were, especially when she would say something ditzy or stupid. “Heather, it’s a good thing you have big tits,” or “Are your boobs cutting off circulation to your brain?” She would always laugh, as she had fun playing into the ditzy card just for the laugh.

She had recently been dating a new guy named Simon. He was a harmless, somewhat boring guy that I was surprised Heather would want to be with, but I think it’s because he was so vanilla that she enjoyed being the “alpha” in the relationship, which she most definitely was. She would still flirt and make inappropriate jokes with all of us, and Simon wouldn’t say shit. I remember thinking, if I had a girlfriend and somebody said the type of shit we all said to Heather to her, I’d have a BIG issue with it. Simon would just smile and sit there.

The night when I got myself into trouble started as a normal poker night, as any. Simon wasn’t there, and we had a good 10 people playing. When Heather arrived, we were pouring drinks in the kitchen, and I asked Heather where Simon was.

“Where’s your dude tonight?”

“He’s at a friend's house.”

“Oh, good, so I have you all to myself tonight.”

“Oh, baby. You sure do!”

“Let's get you nice and liquored up tonight, so you can make some bad decisions.”

“Mmm! Yes, Daddy!”

We laughed. It was a typical back and forth for us; little did I know that it would actually come true this time.

We started the game, and after several bad beats and bad bluffs, I was on tilt. Heather’s stack was doing even worse than mine, and we found ourselves head-to-head in a hand. I had a King and a 10 of spades, and the flop hit 10,7,3, rainbow. I bet into her to see where she stood. She gave me a typical “fuck off” look with her big brown eyes.

“Come on, Luke, you have to play nice with me.”

“I am being nice. You don’t want annnnyyy part of this hand, my love.”

She laughed and deviantly called my bet. The turn came, and it was a 2 of spades. I bet even more into the bet and chirped her some more, giving her a smirk.

“Get outta here, H-Jo, this will cause you nothing but pain.”

She winked at me. “Maybe I like a little pain.”

She raised me. She was wearing a very low-cut blue shirt and tugged her shirt down a bit, purposefully putting her massive cleavage on display for me and gave me a seductive smirk. I knew what she was up to.

“Oh, get outta here with those. What are you trying to say, that you’ve hit a pair?”

“A huge pair,” she giggled and jiggled her boobs ever so slightly.

“Hahaha, so I see!”

She then proceeded with some psychological warfare.

“Don’t be a pussy now, you wanted to be a big man pushing me around! So be a man!”

I really had no idea what she could have that could beat me. Maybe a high pocket pair?

“...what do you have, pocket queens? Kings? What could you possibly have?”

“Come on, Luke! Don’t be a bitch! Stop staring at my boobs and hurry up!” as she jiggled them back and forth even more to distract me while the entire table laughed.

The house we were at belonged to a couple, Jason and Shirley, and Shirley was already out of the game. These two girls constantly teased the lesbian card with us all the time, sometimes making out and would always grope each other. Right on cue, Shirley went behind Heather and grabbed her tits, squeezing them and making them jiggle even more feverishly. Heather just laughed.

“What’s the matter, Luke, can’t focus?” Shirley asked me. The two girls cackled like hyenas. I was trying not to give them what they wanted, but truth be told, I was really enjoying the show, so much that I could feel my cock begin to grow in my jeans. I think those 2 especially liked to tease me with these types of shenanigans because I was single.

“I don’t think you have shit! All in!”

The table all erupted. Heather smirked and reluctantly called, as she had nothing to lose with such a low stack of chips. I flipped my King-Ten onto the table, showing a high pair. Heather sheepishly flipped over her cards, and she had Queen Ace. She needed a queen or an Ace on the river to beat me. Our dealer, Ryan, was about to drop the last card.

“C’mon, Ryan! I will suck your dick for an Ace or a Queen!”

Everybody was cheering for Heather, which I couldn’t blame them for. Ryan slowly flipped over the last card dramatically. A lovely 7 of hearts card, giving me the win! Heather was out, and we shook hands.

“Sorry, hun, I told you that hand was not for you!”

She playfully retorted. “I hope you choke on these chips!”, as she slid them across the table. “Well, time to go get fucked up! Let's get drunk, Shirley!”

Shirley and Heather poured some new drinks and sat on the couch while the rest of us continued playing.

Eventually, I got bled out of my remaining chips and lost in another head-to-head against Derrick, of all people, who was the chip leader after finishing me off. I went and poured a fresh drink and noticed Heather was sitting outside by the fire by herself, so I poured us a couple shots and headed outside.

She was looking gorgeous in her low-cut blue shirt and tight jean shorts as she was smoking a joint. She saw me come out and made a sad face.

“Ohhhh noooo, baby. What happened?”

“Your piece of shit brother took me out!”

“That bastard. He has both of our chips now.”

“That he does. But look, I brought you a shot!”

“You son of a bitch. Stop taking advantage of me!”

“Never.”

We cheers’d and downed the shots and shared some of her joint back and forth. The night continued with more people joining us at the fire. I started to get really fucked up, more than I had planned. I was originally planning on driving home, but Shirley kept feeding us shot after shot. It became apparent that I was going to have to crash there for the night in their spare room, which was fairly typical.

Derrick won the poker game, and the night wore on with eventually only myself, lol Shirley, Jason, Heather, Derrick and Arianna left sitting at the fire. We were waiting for Simon to come pick up Heather, but she received a text at around midnight.

Apparently, Simon got too hammered himself and wasn’t able to drive either. Heather told him to take an Uber home, and she would do the same, before getting more shots for us all. Heather sat right on my lap and force-fed the shot to me before returning to her chair. We flirted all night, like usual.

Derrick and Arianna already had a room for the night, and Shirley and Jason only had the one extra room in their house that I assumed I would use. Jason eventually had enough and went to bed around 1, and Arianna did the same a few minutes later, leaving just Shirley, Derrick, Heather, and me as the final four of the night. We were often the final four at these poker nights.

Shirley was the type of girl who never wanted the night to end and suddenly jumped to her feet.

“Oh fuck! I forgot all about something!” She ran inside and then shortly returned with edible weed cookies.

I was already way too fucked up and attempted to pussy out. “I don’t think I can, I’m already way plenty fucked up.”

Heather chimed in. “Oh come on, you pussy, you HAVE to! It’s cookies! It’s yummy!”

She came and sat on my lap again, this time with her huge boobs rubbing against my arm, and force-fed me the cookie. The others are there’s and, as expected, got even more fucked up in the next half hour or so. Laughing and guffawing at the dumbest shit.

We had all finally hit a wall and decided to go inside to bed.

Shirley piped up, “Heather, it’s way too late to call an Uber, just stay the night. We can drive you home tomorrow morning.”

“I think you’re right, I’ll crash on the couch. Luke, can you drive me home tomorrow?”

“Of course. But you can have the bed, little lady, I’ll sleep on the couch.” So chivalrous, I thought to myself.

“No, no, you can have the bed. You called dibs first.”

“I really don’t mind, I’m gonna pass out immediately anyway, the couch will be fine for me.”

“No way, if you sleep on the couch, I’ll sleep on the loveseat. Fair is fair.”

Shirley interjected with another idea. “Just share the bed, it's big enough. You’ll both literally be asleep in seconds.”

Not going to lie. My cock piqued its interest at the sound of those words. I looked at Heather.

“Well, it’s true, I’ll be down immediately.”

To my surprise, it took no further convincing for Heather.

“Ok, that’ll work. I’ll sleep above the sheets, so you can’t grab up on me.”

“Perfect, I’ll need that. And that’ll help keep my dick away from your butt as well.”

“I’ll probably have to sleep way over on my side to avoid your MASSIVE dick.”

“Oh, 100%. You’ll have to sleep right on the edge, in fact, you may get pushed off the bed.”

“Hahah in your dreams, buddy. I’ll text Simon and let him know not to expect me tonight.”

We laughed, put out the fire and went inside. I was shocked at how wobbly I was from being so fucked up. Shirley went and got us some more sheets and pillows, and we stumbled into the spare room. Derrick headed down the hall and gave me, what I thought at the time, was just a playful warning.

“Alright, no funny business tonight, you two!”

Heather responded. “We’ll try and keep the passionate screams to a minimum.”

Derrick just shook his head in disgust and went to his room to bed. The room was spinning, so I was really happy to be going to bed. I wasn’t sure of the etiquette, so I kept all my clothes on as I went under the sheets. Heather jumped into bed over the sheets and lay beside me and hugged me.

“Are you as fucked up as I am right now?” She asked.

“More.”

Shirley came in and lay with us for a second.

“See!! So much room on this bed! I could sleep in here, too!”

“If you did that, we’d DEFINITELY be knee deep in each other's juices!”

Shirley laughed. “Do you guys need anything? Condoms?”

I responded, “Nope, we’re good. I prefer to bare-back it.”

The girls laughed, and Shirley made her exit. If I weren’t so fucked up, I would have felt weird lying beside Heather, but we were both very close to passing out. I suddenly had a sobering thought and had to double-check with Heather.

“Simon gonna be pissed at this?”

“Nah, it won’t even make the news.”

We laid in the dark there for a bit and passed out. I woke up in the middle of the night, hot as hell. I wasn’t used to wearing full clothes to bed, as I usually slept buck naked. Heather was asleep beside me, so I took a chance and removed my shirt and pants, but left my boxers on. It helped immediately, and I fell back asleep.

I was awakened to Heather squirming. She could tell I was awake and whispered to me.

“Sorry, I’m fucking freezing. I’m coming into the sheets.”

“Oh ok. I’m just in my boxers right now. I was fucking hot as hell under here.”

“That’s ok, I don’t care. Share some warmth.”

She got under the covers, and she slid her feet over to mine, and she wasn’t lying, she was fucking frozen.

“Jesus Christ, you ARE freezing.”

I was still drunk and didn't think to stop her small-spooning into me. I wasn’t sure where to put my arm, but she made the call, grabbing my right arm and positioning it, hugging her, resting on her arms, which were on her big tits. She pushed her ass right into my lower section, and it was pretty obvious that she would be able to feel my cock underneath my boxers, even if it was pressed against her jean shorts.

“Warm me up, please, please. Once I’m warm, I’ll spread back to my side.”

“It’s ok, I don’t mind warming you up.”

“....I think I can feel you….not minding in.” She wiggled her ass against my dick.

“Sorry about that. Hey, I’m just trying to help.”

“Appreciate it, kind sir.”

She then squeezed my hand underneath her arm and against her big breasts, and we cuddled for several minutes. My hand touching her titties did nothing to calm my dick down, but she fell back asleep very fast. The problem was that I was now very wide awake and very aware that my cock was still pushing hard against her ass.

My boner seemed to be getting bigger, and I didn’t want to wake her up, so I slid my arm back away from her and laid on my back, with my cock pointing directly to the ceiling. Thankfully, it eventually settled down, and I managed to fall asleep again.

I was awakened again when I felt her reposition herself, turning over to sleep on her stomach, and her left arm went across my chest as she cuddled up on me again. It was kind of weird, even though I was sure she was still asleep. I let it happen, but felt my cock growing again. I covertly slid my cock under the top of my boxers to keep it at bay.

Heather must have woken up a minute later and realized she wasn’t laying with Simon, as she suddenly removed her arm, but in doing so, it brushed against the top of my cock, which was peaking through the top of my boxers.

To my surprise, she put her hand back gently onto my stomach, and her fingers were gently tapping my belly, like typing on a keyboard, mere inches from the tip of my cock. I took my left arm and put it around behind her neck as we lay there for a few moments until she broke the ice.

“Be honest. Are you horny right now?” she whispered.

I was taken aback by the question, but still drunk/high enough to answer honestly and not really give a shit.

“Um, yeah…quite a bit actually. Are you?”

“Mmmhmm… weed always makes me horny.”

“Me too.”

Her fingers went from tapping my belly to gently scratching it. She alternated between tapping and scratching, and I noticed the tapping started to get lower, slowly tapping down my abdomen, until she started tapping the top of my cock, right on the tip. I didn’t stop her or say anything.

She gave a guttural “mmmm” sound as I pulled her closer with my left arm, pretty tightly wound at that point as she continued to tap her fingers on the top of my cock.

The taps stopped, and her fingers went lower, until she was full-on rubbing my shaft, top to bottom, all the way down to my balls. She rubbed it up and down for a few moments, and she started giggling.

“What the fuck, dude? Why aren’t you stopping me?” she whispered.

“Because I’m fast asleep.”

She giggled. “You’re actually, like….pretty big.”

“You sound surprised?”

“No, I just thought you were all talk, like most guys.”

She continued massaging my cock and balls with her left hand, and I became fully hard. I decided I was in my right to start feeling her up as well, so I reached my right hand under her shirt and started squeezing her breast.

She feigned outrage. “Hey. How dare you?” but began to stroke my cock more feverishly. She then lifted her face close to mine, and we started to make out.

I couldn't believe I was making out with my buddy's sister and a girl I had known since we were kids. It started to get more hot and heavy when she got out of the covers and lifted her blue shirt over her head, revealing the sexiest blue and pink bra, barely containing her massive titties.

“Jesus. You should take your bra off, too, though.” I demanded, brazenly.

“....Yes, Daddy.”

She reached behind and slowly took it off; her massive tits were on full display. She played a little shy and kept her arms on them with the cutest, coy smile I had ever seen. I took control, removing her hands and started squeezing and groping them. This apparently was the trigger for full-on go-time as she got off the bed, ran to the door, locked it and came running back to the bed.

I started playing with her boobs again, as she shoved them in my face, smothering me with them. She then grabbed my middle finger and started sucking on it. I knew what she really wanted.

I got out of the covers and laid there while she went down and pulled off my boxers. My cock snapped out, and she didn’t waste a single second and started sucking on me. Up and down she went while I enjoyed the view. She used lots of saliva and would swirl the tip of her tongue around the tip of my cock, getting me all wet and then would jerk me off tightly with the saliva. She knew what she was doing.

I grabbed the side of her head and started fucking her face. We started getting a bit too loud, and she motioned for me to be quiet. I looked over at the clock, and it was 4:30 in the morning. She gagged on my cock and slobbered all over me.

She stood up and removed her jean shorts and panties, revealing to me all her splendour. I shoved my index and middle fingers into her hot pussy a few times, and then she backed up and started riding my cock up and down reverse cowgirl while I squeezed and handled her plump ass.

After several minutes, the bed was making too much noise, so she got off and started sucking my off again from the side. I played with her big boobs while she blew me. I wanted to fuck her tits so bad, and she noticed.

“You wanna go in here?” she asked quietly. I nodded quietly.

She crawled up to me, I grabbed her tits, spat between them and started fucking them silly. She let me do whatever I wanted to them for several minutes; it was an amazing view. I was very close to busting my load all over them, but managed to compose myself.

After fucking her tits, she got up and started fucking me cowgirl, bouncing up and down on my rock-hard dick. She went to town on me, grinding hard and started moaning really loud. This time, I told her to be quiet.

She was soaking wet when I pulled her off, put her on all fours and started fucking her hard doggy style. We were being pretty loud at this point, as the sound of our flesh slapping into one another sounded deafening, but neither of us could slow down now, and it became an acceptable risk of waking the house. I stuffed her pussy as deep as I could go and rammed her over and over from behind.

When I had my fill, I flipped her over and started fucking her in missionary position, as I wanted to see those titties bouncing. I couldn’t believe all the times we joked about fucking, we were actually doing it. Her pussy was so warm and tight, I couldn’t get enough. I continued thrusting her, as she played with her clit, her tits bouncing out of control, hitting her in her chin. She grabbed her own tit and started licking her own nipple while I fucked her, which was the last straw for me.

I whispered as quietly as I could, “I’m gonna cum.”

She got up and pushed me onto my back and started sucking me off again, very violently, at the same pace I was fucking her pussy. I knew the unspoken assignment was to cum in her mouth, so I thrusted a few more times and then started exploding cum into her mouth. She tried to swallow it all, but it was a massive amount, and several gooey strands came out of her mouth and landed on my cock and balls.

She swallowed and then wiped the cum off me and swallowed that too. She smiled at me and said “Yum”, which drove me crazy. What a good little slut.

There wasn’t much cleanup thanks to her efforts, although there were some wet spots on the bed, which we just chose to lie in as we went back to sleep, this time naked and side by side.

We both woke up around 8ish when we heard people in the kitchen. My head was pounding, and Heather looked like a mess, too. We both looked at each other.

“Man, I had the weirdest dream last night,” I said with a smirk.

“Yeah? Me too.”

“Unrelated, but where the hell are my clothes?”

“Umm…mine are missing too. What the hell?”

“Aliens, you figure?”

“It’s the only answer.”

I kissed her on the lips and felt up her tits for good measure.

“So, I assume we’ll have to keep last night quiet.”

“Uhhh, yeah, I think so. ‘Till the day we die.”

She reached down under the cover and grabbed my dick, which was hard again.

“Why the fuck do you still have a boner?”

“Oh, I dunno, because it’s morning? Because you're naked? Pick one.”

“Let me help you with that real quick.”

I wasn’t about to say no, and she went under the covers and started giving me a bonus morning blowjob. I already knew the door was locked, so I went with it. I stood up on the bed, and she went on her knees and sucked me off again. I looked down at her beautiful eyes, looking up. She let me titty fuck once last time, and before I was close, I stuck my cock back in her mouth to feed her more cum.

She must have felt me getting close, as she looked up at me, with my cock fucking her mouth, and nodded, giving me the green light. As silently as I could be, I started to cum in her mouth again, not as much as the previous night, but it was a miracle that anything came out after the previous night emptied my balls. The good girl swallowed and cleaned me up with her tongue again.

We got cleaned up and dressed and gave each other a pep talk before we left the room to join the others in the kitchen. Everybody was having breakfast and looked a little worse for wear.

“Morning, love birds.” Said Shirley.

Heather went and gave her a big hug. I felt enormous guilt when I went over to Derrick and gave him a fist bump and said good morning.

Heather risked it. “So, hopefully we weren’t too loud last night?”

I gave a nervous laugh, but everybody else laughed it off, with nobody the wiser that something actually happened. We all ate breakfast, and afterwards I drove Heather home to her unsuspecting boyfriend, Simon. I gave him a guilty wave from my car, then went home and laid in bed, thinking about the crazy night I just had.