Drunk anal with a friend’s sister [MF] (Long)

TL:DR – Got an amazing blowjob and had drunk anal sex with a friend’s sister in college, leading to regular hookups for awhile.

So this was years ago when I (28m) was in college.

I’d gone over to a friend’s house, let’s say her name is Violet, to drink and blow off some steam after a particularly rough round of midterms. We’d do this on a fairly regular basis with a whole group of friends and roommates, getting absolutely trashed and going over our classes and tests since we were in the same major.

Now, Violet and I never had a thing despite her being absolutely gorgeous. Petite blonde, nice body, funny, but I just never had any desire to have sex with her. Besides, she had a long-term boyfriend (now husband) who is an awesome dude to hang out with. Violet’s sister Pink, on the other hand…

Tall, curvy, brunette, just a great body, very open, and one of the biggest flirts I’ve ever met. She was a year below us in college and was always present for our drunken escapades since she was living with her sister. I swear basically all the men that were ever over or in the group wanted to be with her at one point or another, and frankly, several of us succeeded.

It was a standard night, blaring music too loud, drinking, smoking, having an absolute blast after a stressful week preparing papers and projects. Violet got TRASHED and had to be carried to her room for a toilet nap and a drunk tuck in, the others started drifting away pretty quickly as midnight approached. I was still up drinking, plenty drunk myself, and ended up on the couch with a drunk Pink.

She gets cuddly when she’s drunk, so she’s leaning on me and picking new music to play on the TV, all pretty standard stuff at this point. The last person leaves while we’re talking and laughing, I pull her in close and just fall over with her. We lay there for a while. I was getting close to nodding off as she pressed up to me and cuddled up close when she turned her head and whispered to me.

“Hey, Orion?”

“Hmm?”

“I have a room with a bed, you know,” she said simply, pulling my arm to make me hold her tighter.

“You ready to call it a night then?,” I asked drunk and stupid.

“I mean, you could join me if you want. It’s more comfy than the couch,” she said, rubbing my knuckles with her thumb.

“Sure, I’m not driving anywhere tonight,” I said, my heart starting to beat harder.

She slid off the couch, standing and stretching with a yawn before grabbing my hand and pulling me up to lead me to her room across the hall from her sister. I sat down and got my shoes off, stripping off my socks and jacket while she went to the bathroom to change for bed. The bed was definitely more comfortable, so I flopped back and rested my head against the mountain of pillows.

She comes out of the bathroom in an overlong shirt and panties, her hair put up in a messy bun with a smile, face that bright drunk kind of red.

“I hope this is okay, I normally sleep naked but with you here…” she said with a shrug as she flipped off the overhead light.

I feel her climb into the bed, barely illuminated by the moonlight outside her window as she crawls over the top of me back into the cuddle we’d been sharing. I wrap my arm around her tight, I pulled her in and against me, turning her head with my chin so my face was against her ear and not buried in her wild hair. She starts pressing her ass into me and sighs slightly, her eyes closing as she grinds on me lightly.

“Hey, Orion?” she said, turning around so we were face to face in the moonlight.

“Yeah?”

“Is this alright?”

“I certainly hope so, you invited me. Though it might be a bit awkward if anyone finds out,” I said, inches from her face.

“Yeah, it might be. But I mean, you haven’t made a move yet. Do you not think I’m attractive or something?”

“I… I didn’t know… You’re Violet’s sister and… I just don’t want to ruin anything,” I stammered, eyes focused on hers, hand on her stomach.

“So maybe we don’t let anyone know,” she said as she inched her face closer, taking my hand and guiding it under her shirt.

“Maybe we don’t,” I said as I leaned in close and kissed her, tasting and teasing her with my tongue as my hand trailed up her stomach. She started kissing me roughly, nibbling on my lips as her hand brought mine quickly to her tits.

We made out for a few minutes before she sat up and immediately threw her shirt off, raising her arms and showing off her perky C-cup tits before straddling me. I leaned forward, my own shirt coming off before licking and teasing her nipples with my teeth. Moaning, she scratched her arms down my back and pushed me down to the bed, grinding hard and nibbling on my neck.

“I’m on my period, so we can’t fuck. But I have an idea for that,” she whispered in my ear before starting to kiss down my chest. After struggling with my belt for a minute, my pants were off, and my dick was rock hard.

Smiling, she kissed down my stomach and pulled my boxers down, stroking me slowly as she held my eyes before trailing her tongue lazily up my shaft. I shuddered and let out a small sigh as she started teasing me with her tongue, leaning down to suck my balls without ever breaking eye contact. Then she got serious.

She swallowed my dick in one swift motion, hand playing with my balls as she lapped and deep throated my dick. She is easily still one of the best blowjob givers I’ve ever met, her tongue never stopped working my balls or cock as she gave me one of the wettest, most enthusiastic blowjobs I’ve ever had.

“Fuck Pink!” I half whispered as I watched her swallow me over and over, only coming up briefly to breathe before doing her best to break her nose against my pelvis again. My drinking made it almost impossible for me to cum, but it felt incredible to have her take my whole cock so easily.

Eventually I had her turn around, showing me her nice firm ass as she continued to fuck me with her mouth. I started playing with her clit and she somehow went even harder, determined to make me cum down her throat but I just couldn’t.

“Fuck I need a break. My jaw hurts, and you don’t even seem close!” She said as I continued roughly circling her clit, arching her back and showing off her amazing ass.

“Sorry, it’s the drinking. Besides, the way you’re going, I’d think you were a pro, not that your jaw would hurt!” I teased, panting as I played with her pussy.

“I don’t normally take long,” she said before attacking my dick again, eliciting new moans from me.

“Maybe you should let me fuck your ass then,” I said jokingly, brushing my thumb up and pressing lightly on her tight little asshole. Leaning back and taking a deep breath, she started stroking my cock and pressed her ass harder into my thumb.

“I’ve actually never done that before… Fuck it,” she said, throating me again and trailing even more spit on my already soaked cock. Leaning up, she straddled my cock facing away from me and pressed it into her ass, wincing as we slowly moved the head inside her. Moaning softly, I slowly pushed into her, listening to her whimper and then moaning as my head passed into her, and she slowly sank onto me.

“Fuck Orion..” she said, slowly sliding up and down my hard cock, her little asshole stretching around me as I watched her start to ride me in earnest. Barely remembering to try and be quiet, we were both moaning and she started riding me harder, pounding my cock into her as fast as she could manage. I leaned up, groping her tits and playing with her clit until she came riding my cock.

We must’ve gone at it for hours, sweating and panting as she rode me for all she was worth, but as the sun started coming up, she hopped off and told me to take over. I roughly fucked her, listened to her panting and begging for me to spank her, to pull her hair, I just couldn’t cum. Eventually she told me she had to stop, falling face first into her pillows and breathing hard. I collapsed into her shoulder, kissing her neck, barely awake at this point and told her that she owed me one.

I grabbed her by her hair, lifting her up for a rough kiss, and got up to get dressed in the early morning light. Fully sober now, I decided to drive the short way home, downed a ton of water, and passed out. She texted me the next day telling me she didn’t forget she owed me one and to come by that night for what would become a regular hookup.

Source: reddit.com/r/gonewildstories/comments/10fksfl/drunk_anal_with_a_friends_sister_mf_long