*Or how I woke up on New Year’s Day with a thumping headache and my ex-girlfriend’s naked little sister asleep on my chest.*
I broke up with Hannah about a year ago after being together for two years. She was the oldest [F27] of three sisters. At a New Year’s Eve party a couple of months ago I ran into her youngest sister, Chloe [F23].
Chloe (5’3″ with long dark brown hair and gym-honed curves) is a typical annoying younger sibling. She can be immature and manipulative but she is also undeniably the hottest of the three girls, something I tried not to acknowledge while I was with Hannah. Mostly I tried to ignore her because she was annoying and sometimes a bit of a bitch but she also has this mischievous smile that can make your cock stand on end.
It was after midnight and I was quite drunk. Chloe seemed happy to see me. She insisted that I dance with her so I did, drunkenly holding on to her hips to keep myself upright, which she found hilarious. She was wearing a very slutty red sparkly dress that showed off her tits and thighs. I was in a drunken trance, swaying from side to side and staring at her breasts.
”Are you pleased to see me?” she asked and shot me one of those grins.
”Erm, I guess so” I slurred.
”Let‘s see” she said as she grabbed at my cock through my pants, which took me completely by surprise. At this point I had a pretty good semi, which was impressive given the amount of alcohol I’d consumed. She must have liked what she found because the next thing I knew she had her tongue in my mouth and her hands holding onto the back of my head pulling me down to her level.
Sober me knew this was a bad idea. Drunk horny me was happy to follow her lead. My hands were still on her hips as I pulled her up against me but soon started to wander, feeling up her ass and tits while we made out. I discovered at this point that Chloe is a biter. She kept playfully nibbling my lips, ears, neck and anything else she could get her mouth on. Not something I thought I’d be into but it was surprisingly hot.
We must have carried on like this for 5 minutes or so, kissing, touching and grinding on each other, until she pulled away and asked ”so when are we going back to your place?”
My brain briefly tried to wrest back control: “I’m not sure that’s a good idea…”
“Yes it is” Chloe over-ruled and led me outside by the hand. We flagged down a passing cab and spent the 10 minute ride kissing and touching each other in the back seat. She had her hand on my thigh and kept trying to touch my cock but I kept pulling her away – I didn’t want to cum in a taxi.
As soon as we got through my door she unzipped me and pulled out my cock. She got down on her knees and took me in her mouth. Hannah was never keen on blowjobs so I never insisted, but her slutty little sister couldn’t get enough of it. She looked so cute as she stared up at me while sucking and slurping enthusiastically and within no time I was ready to burst. “Slow down!” I begged as I pushed her away from me. She flashed me another of those dirty smiles.
Chloe had been to my place before, although in entirely different circumstances along with Hannah, so she knew the layout. She took me by the hand again and dragged me to the bedroom. I still had my pants around my ankles and was unsteady from the drink so inevitably I tripped and fell on the bed, which set her off in hysterics.
I laid on my back and Chloe removed my pants. She then made me take my shirt off so I was completely naked, on my back with my cock standing to attention. She was still fully clothed (well as much as she had been all night). She stood on the foot on my bed, towering above me, and slipped her panties off – a tiny little red thong to match her dress – and then through some impressive contortions removed her bra, also red, without taking her dress off.
“You want more?”
I nodded eagerly.
As I mentioned before, Chloe could be devious, she liked to play games and manipulate people. “Beg for it” she demanded.
“Huh?”
“If you want the dress to come off you have to ask nicely.”
“Please Chloe, please take your dress off.”
She just looked at me.
“Please Chloe!” I pleaded pathetically.
A wicked little smile crept onto her lips – “OK” – and she slipped the straps off her shoulders and pulled the dress to her feet in one movement.
Holy fuck! I knew Chloe had a sexy body – I’d studied every one of her Insta gym photos in some detail – yoga pants, sporty crop tops and all – but this was something else. She had the best tits I’d ever seen, c-cup I’d guess with perfect hard little nipples, and her pussy trimmed with the cutest little landing strip. She was visibly wet which turned me on even more.
“So you want to fuck your ex-girlfriend’s innocent little sister, do you?”
There was absolutely nothing innocent about this little sister.
“Yes please”
“You have to ask nicer than that” she instructed.
“Please can I fuck you Chloe?”
She was loving this.
“Maybe I should tell Hannah how you begged for my pussy?
Oh! The thought crossed my mind that this was all one big mindfuck, another one of Chole’s games, a way to get one over her big sister. It wouldn’t be beyond her but I was too drunk to care.
Chloe lowered herself to her knees, one either side of my stomach and leant down for kiss, biting my bottom lip and then flicking my tongue with hers. I helped myself to two handfuls of her perfect tits and fondled them in awe.
“You wanna suck ’em?”
I absolutely did. I wasn’t sure if I was still supposed to be begging so I played it safe.
“Please can I suck on your tits Chloe?”
She laughed and guided her breast to my mouth. I latched on like a new born baby getting its first feed. I sucked contentedly for a while, alternating between breasts as Chloe gently stroked my cock. My head was spinning but I was in heaven. I’d have happily spent the rest of the night like that but Chloe had other ideas. She grabbed my hand and guided it to her pussy. I slid my finger along her slit and felt how wet she was. My finger easily slipped inside. She moaned and then pulled my hand away.
“I don’t wanna fuck your hand”.
She shifted backwards and positioned herself over my erection and teased me, rubbing her pussy against the tip. Then she bit her lip, closed her eyes and carefully lowered herself onto me. She felt incredible and when she flashed that smile again I wondered if I’d spent two years fucking the wrong sister.
Cowgirl was a good choice because I was too inebriated to do anything that required any more coordination on my part. I let Chloe lead the way, mesmerised by her tits bouncing above me as she rode my cock. I tried to buck my hips up into her, but she didn’t want that so I laid there and let her ride me at her own pace. Hannah had always been quite quiet and reserved in bed but her sister was the opposite. She knew how to have fun and wasn’t afraid to show it. The sounds of Chloe enjoying herself, laughing and moaning as she got herself off on my cock, pushed me close to the edge.
God bless alcohol because I wouldn’t have lasted 30 seconds without it. I think I got to a slightly more respectable 3 minutes or so before I let her know “Chloe, I’m gonna cum”.
“Me too!” was her breathless response. And she did, loudly, just before I unleashed a torrent inside her.
I was starting to sober up a little at this point as the post-nut clarity momentarily kicked in to remind me “that’s Hannah’s little sister, what the fuck are you doing?” but I pushed the thought to one side as Chloe collapsed on top of me giggling.
“Was I better than Hannah?”
I didn’t say anything but I gave her the answer she was looking for with a nod and a smile and her face lit up. She kissed and bit me and we made out for several minutes with my cock still inside her. All the while she kept expertly massaging my balls and before long I was hard again.
Chloe sat herself upright on my cock once more. “Fuck me again”.
I did as I was told. I had to work harder to cum a second time, which meant I could be more aggressive. I think she enjoyed that. This time she let me thrust into her and we found a rhythm that worked for both of us. She came again before I gave her the last of what I had left in my tired balls and we fell asleep.
I woke up about 8am, sober now but with a splitting headache. Chloe was fast asleep on top of me until I tried to sit up. Only one of us seemed to be hungover. A quick conversation ensued in which we agreed there was no need for Hannah to find out about this and that this would just be a one-time thing (if I was just about the sex I would have fucked Chloe every single day but I can’t deal with her immaturity and the drama and games). I called Chloe a cab while she took a shower and then she was on her way and we haven’t spoken since.
Source: reddit.com/r/gonewildstories/comments/11sxcus/mf_i_had_a_drunken_onenight_stand_with_my_exs
Love this! A shame you didn’t fuck her again
Bravo! Very hot that y’all went at it raw. Now you need to track down the middle sister
The only reason I find this story hard to believe is because you got a cab that easily on NYE.
Good man. You’ve got a line in the sand you only cross when inebriated – like the rest of us.
You’re a better man than I to have kept it to a one-time thing.
Sounds awesome. Good job man, you are living the dream.
great story
Hot story 🥵
If this wasn’t your ex’s sister, this story would be half as hot.
I would have no remorse and would want to bang her again.